CN101627068A - Aqueous polyurethane based resin composition and the coating composition that uses it - Google Patents
Aqueous polyurethane based resin composition and the coating composition that uses it Download PDFInfo
- Publication number
- CN101627068A CN101627068A CN200880006932A CN200880006932A CN101627068A CN 101627068 A CN101627068 A CN 101627068A CN 200880006932 A CN200880006932 A CN 200880006932A CN 200880006932 A CN200880006932 A CN 200880006932A CN 101627068 A CN101627068 A CN 101627068A
- Authority
- CN
- China
- Prior art keywords
- composition
- aqueous polyurethane
- based resin
- liquid shape
- polyisocyanate compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000004814 polyurethane Substances 0.000 title claims abstract description 78
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 75
- 239000011342 resin composition Substances 0.000 title claims abstract description 56
- 239000008199 coating composition Substances 0.000 title claims abstract description 24
- 239000000203 mixture Substances 0.000 claims abstract description 115
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 72
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 72
- -1 succinate class sulfonate Chemical class 0.000 claims abstract description 72
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 61
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 56
- 239000007788 liquid Substances 0.000 claims abstract description 49
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- 239000002904 solvent Substances 0.000 claims abstract description 33
- 238000009835 boiling Methods 0.000 claims abstract description 30
- 239000002253 acid Substances 0.000 claims abstract description 28
- 229920005862 polyol Polymers 0.000 claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 claims abstract description 25
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 21
- 150000002632 lipids Chemical class 0.000 claims abstract description 19
- 230000003472 neutralizing effect Effects 0.000 claims abstract description 18
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims abstract description 15
- 238000006276 transfer reaction Methods 0.000 claims abstract description 15
- 239000000654 additive Substances 0.000 claims description 40
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 38
- 230000000996 additive effect Effects 0.000 claims description 36
- 239000011248 coating agent Substances 0.000 claims description 26
- 238000000576 coating method Methods 0.000 claims description 20
- 229920005749 polyurethane resin Polymers 0.000 claims description 20
- 239000000463 material Substances 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- 239000011734 sodium Substances 0.000 claims description 17
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 16
- 229910052708 sodium Inorganic materials 0.000 claims description 16
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 15
- 239000006185 dispersion Substances 0.000 claims description 15
- 229920000515 polycarbonate Polymers 0.000 claims description 12
- 239000004417 polycarbonate Substances 0.000 claims description 12
- 229920005989 resin Polymers 0.000 claims description 12
- 239000011347 resin Substances 0.000 claims description 12
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 8
- 229920000570 polyether Polymers 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000002009 diols Chemical class 0.000 claims description 5
- 229920000728 polyester Polymers 0.000 claims description 5
- 238000005829 trimerization reaction Methods 0.000 claims description 5
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 claims description 5
- 239000000839 emulsion Substances 0.000 abstract description 8
- 239000003431 cross linking reagent Substances 0.000 abstract description 5
- 238000010790 dilution Methods 0.000 abstract description 5
- 239000012895 dilution Substances 0.000 abstract description 5
- 239000000243 solution Substances 0.000 abstract description 3
- 230000000052 comparative effect Effects 0.000 description 31
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical group O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 25
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 20
- 125000000129 anionic group Chemical group 0.000 description 20
- 238000002156 mixing Methods 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 13
- 238000012986 modification Methods 0.000 description 12
- 230000004048 modification Effects 0.000 description 12
- 238000003860 storage Methods 0.000 description 12
- 239000003513 alkali Substances 0.000 description 10
- 150000003077 polyols Chemical class 0.000 description 9
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 9
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
- 238000010276 construction Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 7
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000470 constituent Substances 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 229920000768 polyamine Polymers 0.000 description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 229920005906 polyester polyol Polymers 0.000 description 5
- 229960004063 propylene glycol Drugs 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 239000004202 carbamide Substances 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
- 235000013772 propylene glycol Nutrition 0.000 description 4
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 3
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 238000013038 hand mixing Methods 0.000 description 3
- 229940051250 hexylene glycol Drugs 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002596 lactones Chemical class 0.000 description 3
- CZRKJHRIILZWRC-UHFFFAOYSA-N methyl acetate;propane-1,2-diol Chemical class COC(C)=O.CC(O)CO CZRKJHRIILZWRC-UHFFFAOYSA-N 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- HIFVAOIJYDXIJG-UHFFFAOYSA-N benzylbenzene;isocyanic acid Chemical class N=C=O.N=C=O.C=1C=CC=CC=1CC1=CC=CC=C1 HIFVAOIJYDXIJG-UHFFFAOYSA-N 0.000 description 2
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 2
- LDUOHXCVIFQGBK-UHFFFAOYSA-N carbonisocyanatidic acid Chemical group OC(=O)N=C=O LDUOHXCVIFQGBK-UHFFFAOYSA-N 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 230000000994 depressogenic effect Effects 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000004945 emulsification Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- JBFHTYHTHYHCDJ-UHFFFAOYSA-N gamma-caprolactone Chemical compound CCC1CCC(=O)O1 JBFHTYHTHYHCDJ-UHFFFAOYSA-N 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920001195 polyisoprene Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- PFYHYHZGDNWFIF-UHFFFAOYSA-N (+)-DMDP Natural products OCC1NC(CO)C(O)C1O PFYHYHZGDNWFIF-UHFFFAOYSA-N 0.000 description 1
- BJZYYSAMLOBSDY-QMMMGPOBSA-N (2s)-2-butoxybutan-1-ol Chemical compound CCCCO[C@@H](CC)CO BJZYYSAMLOBSDY-QMMMGPOBSA-N 0.000 description 1
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 description 1
- MNAHQWDCXOHBHK-UHFFFAOYSA-N 1-phenylpropane-1,1-diol Chemical compound CCC(O)(O)C1=CC=CC=C1 MNAHQWDCXOHBHK-UHFFFAOYSA-N 0.000 description 1
- PFYHYHZGDNWFIF-KVTDHHQDSA-N 2,5-bis(hydroxymethyl)-3,4-dihydroxypyrrolidine Chemical compound OC[C@H]1N[C@H](CO)[C@@H](O)[C@@H]1O PFYHYHZGDNWFIF-KVTDHHQDSA-N 0.000 description 1
- LKMJVFRMDSNFRT-UHFFFAOYSA-N 2-(methoxymethyl)oxirane Chemical compound COCC1CO1 LKMJVFRMDSNFRT-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 1
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 1
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 1
- PFYHYHZGDNWFIF-OMMKOOBNSA-N 2R,5R-Dihydroxymethyl-3R,4R-dihydroxy-pyrrolidine Natural products OC[C@@H]1N[C@@H](CO)[C@H](O)[C@@H]1O PFYHYHZGDNWFIF-OMMKOOBNSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical class C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 238000006957 Michael reaction Methods 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- AYDQIZKZTQHYIY-UHFFFAOYSA-N OC(=O)C1(C)CC(C(O)=O)=CC=C1 Chemical compound OC(=O)C1(C)CC(C(O)=O)=CC=C1 AYDQIZKZTQHYIY-UHFFFAOYSA-N 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 238000012644 addition polymerization Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 239000012874 anionic emulsifier Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- PGEAEAYLSCKCCO-UHFFFAOYSA-N benzene;n-methylmethanamine Chemical compound CNC.C1=CC=CC=C1 PGEAEAYLSCKCCO-UHFFFAOYSA-N 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 238000007596 consolidation process Methods 0.000 description 1
- 239000011258 core-shell material Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- 150000007520 diprotic acids Chemical class 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- MPVXINJRXRIDDB-VCDGYCQFSA-N dodecanoic acid;(2r,3r,4r,5s)-hexane-1,2,3,4,5,6-hexol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CCCCCCCCCCCC(O)=O MPVXINJRXRIDDB-VCDGYCQFSA-N 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- HCPOCMMGKBZWSJ-UHFFFAOYSA-N ethyl 3-hydrazinyl-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)NN HCPOCMMGKBZWSJ-UHFFFAOYSA-N 0.000 description 1
- 229960005082 etohexadiol Drugs 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 239000006115 industrial coating Substances 0.000 description 1
- 239000012770 industrial material Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000006224 matting agent Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-N methyl undecanoic acid Natural products CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical class C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229940059574 pentaerithrityl Drugs 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- GCCVBRCGRJWMDX-UHFFFAOYSA-N phenoxybenzene;sodium Chemical compound [Na].C=1C=CC=CC=1OC1=CC=CC=C1 GCCVBRCGRJWMDX-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 230000000176 photostabilization Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N tolylenediamine group Chemical group CC1=C(C=C(C=C1)N)N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/36—Hydroxylated esters of higher fatty acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
- C08G18/348—Hydroxycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/44—Polycarbonates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6633—Compounds of group C08G18/42
- C08G18/6659—Compounds of group C08G18/42 with compounds of group C08G18/34
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/758—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing two or more cycloaliphatic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/7806—Nitrogen containing -N-C=0 groups
- C08G18/7818—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups
- C08G18/7837—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups containing allophanate groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/41—Compounds containing sulfur bound to oxygen
- C08K5/42—Sulfonic acids; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Problem of the present invention is, in water-based polyurethane cold coating composition, use internal crosslinking agent and outside linking agent, thereby further improve the binary liquid shape composition of the hardness of filming, and using high boiling solvent to make the glossiness that raising is filmed under the outside linking agent dilution dispersive situation for the Combination of improving outside linking agent and host emulsion.The scheme of its solution is a kind of binary liquid shape aqueous polyurethane based resin composition, it is characterized in that, contain as (A) composition: make (a) diisocyanate cpd and (b) have the lipid acid of active hydrogen group and (c) cooperating polyfunctional group polyisocyanate compound and succinate class sulfonate in the polyurethane prepolymer that polyol compound reaction obtains, carry out the aqueous polyurethane resinoid that transfer reaction obtains after the neutralizing treatment, contain: can be scattered in the polyfunctional group polyisocyanate compound in (A) composition as (B) composition.
Description
Technical field
[0001] the present invention relates to aqueous polyurethane based resin composition and as the coating composition of its excellent purposes, specifically, relate to water-based polyurethane cold coating composition and manufacture method thereof, this water-based polyurethane cold coating composition is the succinate class sulfonate that cooperates in binary liquid shape aqueous polyurethane based resin composition as particular emulsifier, the hardness of film of ambient cure and glossiness improve, the water-based polyurethane cold coating composition that storage stability is also excellent.
Background technology
[0002] because the rerum natura of the various excellences of polyurethane resin composition, multifunction etc., it is widely used in coating, tackiness agent or printing-ink, various Industrial materials formed materials etc.
Wherein, as coating agent; especially the polyurethane resin composition as coating composition is mainly used in coating of automotive material, building materials etc.; but with regard to considerations such as environment protection, operational securities; expectation is with an organic solvent water-based (water system) composition not; for with an organic solvent and economically not favourable aqueous urethane resin composition,, improve research in order to obtain various rerum naturas such as the water tolerance same, solvent resistance with the organic solvent based composition always.
[0003] as exemplary, the water-based that discloses the application's applicant applies the manufacture method of agent with polyaminoester emulsion, this method is to improve the tunicle outward appearance and the water tolerance of waterborne polyurethane resin coating agent, the improving technology of various rerum naturas such as solvent resistance, comprise following content: make organic diisocyanate and macromolecule polyol and contain the reaction of carboxyl low-molecular-weight diol, manufacturing contains the terminal polyurethane prepolymer (A) of carboxyl isocyanate group, with it with the hydrophobicity polyisocyanates or contain nonionic polar group polyisocyanates (B) and mix, utilize then in the neutralizing agent (C) and system in carboxyl after, in water, make it emulsification, carry out transfer reaction.(with reference to patent documentation 1 and patent documentation 2)
The application's applicant constantly carries out described water-based and applies the research of agent with polyaminoester emulsion and manufacture method improvement and application, example as its a series of improving technology, a large amount of related development technique have been proposed in first to file, for example: proposed a kind of aqueous urethane resin composition (PCT/JP2006/306156), this aqueous urethane resin composition is to prolong gelation time etc. for the reactivity of controlling isocyanate group, it is characterized in that, contain as (A) composition: make (a) diisocyanate cpd and (b) have terminal hydroxyl and have the compound of the carbonyl adjacent with carbon-to-carbon unsaturated bond, (c) have the lipid acid of active hydrogen group and (d) polyol compound reaction obtain, the water system polyamines resin that comprises the residual amino that produces by reaction of the urea after the neutralizing treatment and Michael reaction, and conduct (B) composition contains: can be scattered in the polyisocyanate compound in (A) composition; Proposed in addition, in order to improve water dispersible, storage stability etc., in same ester-polyurethane resin emulsion, blocked isocyanate forms the emulsion compositions that contains blocked isocyanate (Japanese Patent Application 2006-223683) etc. of the emulsion particle of fine core shell structure.
[0004] and, the application's applicant is in order further to develop improvement described water system (water-based) polyurethane resin composition, when making waterborne polyurethane resin, in polyurethane prepolymer, cooperate the polyfunctional group polyisocyanates and improve the internal crosslinking degree, and make aqueous urethane resin composition become binary liquid shape (second-component system) with polyfunctional group polyisocyanate compound solidifying agent, make form variation as coating composition (coating composition) from a liquid type.
But, when using inner high crosslinked low hydroxyl waterborne polyurethane resin, for the binary liquid shape composition, in order to reduce polyfunctional group polyisocyanate compound viscosity, improve Combination, and the film-forming properties that improves composition, utilize the high boiling solvent dilution to disperse the polyfunctional group polyisocyanate compound, but produce following problem this moment: coating binary liquid shape composition and the gloss of filming that obtains significantly reduces.
[0005] in addition, as the method for the lining coating film gloss of the waterborne polyurethane resin coating composition that improves second-component system, known have: the method (with reference to patent documentation 3) that cooperates polyvalent alcohol additives such as ethylene glycol, neopentyl glycol in the waterborne polyurethane resin dispersion liquid; Use has the method (with reference to patent documentation 4) of the water dispersible polyisocyanate curing agent of the polyether chain that contains ethylene oxide unit etc., even if but glossiness improves, and the storage stability of hardness of film, coating composition etc. can not be thought enough satisfaction.
[0006] patent documentation 1: TOHKEMY 2005-194375 communique (summary)
Patent documentation 2: TOHKEMY 2005-247897 communique (summary)
Patent documentation 3: Japanese kokai publication hei 4-233983 communique (summary, 0044～0045 section)
Patent documentation 4: TOHKEMY 2000-34439 communique (summary)
Summary of the invention
The problem that invention will solve
[0007] in water system (water-based) polyurethane resin composition of 0004～0005 section record, use inner high crosslinked low hydroxyl waterborne polyurethane resin and when further improving hardness of film, for the binary liquid shape composition, utilize the high boiling solvent dilution to disperse the polyfunctional group polyisocyanate compound for the Combination that improves polyfunctional group polyisocyanate compound and host emulsion, but, being coated with the gloss of filming that the binary liquid shape composition forms this moment significantly reduces, therefore, the present invention's problem that should solve is the glossiness that improves under the described situation.
The scheme that is used to deal with problems
[0008] the present inventor is in order to solve above-mentioned problem, by the crosslinked hardness of film that improves in outside, in order to improve the coating film gloss under the aqueous polyurethane based resin composition that binary liquid shape (second-component system) promptly used the crosslinked low hydroxyl waterborne polyurethane resin of inner height, for described aqueous polyurethane based resin composition, consider to have studied each composition raw material modification, change or append the new constituent material, cooperate new additive etc., and carry out test repeatedly.In this process, can find: select additive and add the anionic emulsifier-succinate class sulfonate of cooperation as special additive, especially add when cooperating the dialkyl group Sodium succisulfosuccinate, waterborne polyurethane resin host improves with the Combination of the polyisocyanate curing agent that utilizes the high boiling solvent dilution, dispersiveness improves, the gloss that lining is filmed significantly improves, thereby has finished the invention.
[0009] its basic comprising is a kind of binary liquid shape aqueous polyurethane based resin composition, it contains: making diisocyanate cpd obtain cooperating in the polyurethane prepolymer polyfunctional group polyisocyanate compound and succinate class sulfonate with lipid acid with active hydrogen group and polyol compound reaction, carry out the aqueous polyurethane resinoid that transfer reaction obtains after neutralizing treatment; And contain: can be scattered in the polyfunctional group polyisocyanate compound in the aqueous polyurethane resinoid as other composition.As other schemes, be at described binary liquid shape aqueous polyurethane based resin composition, in the polyfunctional group polyisocyanate compound of other compositions, cooperate succinate class sulfonate.
[0010] more particularly, as the additional embodiment of ideal, succinate class sulfonate is the dialkyl group Sodium succisulfosuccinate, with respect to 100 mass parts water-based polyurethane resin dispersions, cooperate 0.3～3.5 mass parts, diisocyanate cpd is the aliphatic diisocyanate compound, lipid acid with active hydrogen group is dihydroxymethyl lipid acid, polyol compound is that number-average molecular weight is 800～6000 polyester glycol or polycarbonate diol or polyether glycol, polyfunctional group polyisocyanate compound as solidifying agent is HDI trimerization build polyisocyanates or HDI allophanate type polyisocyanates, and transfer reaction utilizes water or amine to carry out.
In addition, other compositions dilute by high boiling solvent, solidify making under the aqueous resin composition normal temperature under the form of coating agent, and binary liquid shape aqueous polyurethane based resin composition is to contain the binary liquid shape water-based polyurethane cold coating composition of coating with additive.Further, coating composition is that two components as the polyfunctional group polyisocyanate compound of solidifying agent of the aqueous polyurethane resinoid of host composition and other compositions become cover material, when using as coating, coating composition is the water-based polyurethane cold coating composition that mixes two components.
[0011] as the manufacture method of aqueous polyurethane based resin composition of the present invention, by making the aqueous polyurethane resinoid and becoming composition set manufacturing as the polyfunctional group polyisocyanate compound that can be scattered in the aqueous polyurethane resinoid of other compositions, the following formation of wherein said aqueous polyurethane resinoid: make diisocyanate cpd, lipid acid and polyol compound reaction with active hydrogen group, form polyurethane prepolymer, cooperate polyfunctional group polyisocyanate compound and succinate class sulfonate, utilize neutralizing agent to carry out carrying out transfer reaction after the neutralizing treatment, form the aqueous polyurethane resinoid.
[0012] in the present invention who forms by above basic comprising and embodiment; enumerate following feature; it is special function; (i) the polyurethanes resin combination of water system, therefore it basically not with an organic solvent do not solved problems such as environment protection, operational security; economy also improves; can not damage the storage stability of resin combination, the glossiness that lining is filmed improves, and can also further improve the hardness that lining is filmed.(ii) original, if mismatch polyfunctional group polyisocyanates, even the gloss excellence of filming as other compositions, water tolerance, alkali resistance are also low, if cooperate polyfunctional group polyisocyanates as other compositions, the gloss excellence of filming, water tolerance, alkali resistance are also high.(iii) the polyurethanes resin combination of water system is a binary liquid shape, therefore mix in the time of can being coated with construction at the use scene, thereby storage-stable can be guaranteed construction, utilize even do not use mixing and blending machine hand mixing just mix can be easily with the high boiling solvent dispersion polyfunctional group polyisocyanates of other compositions equably dispersing and mixing in host, owing to be normal temperature cured type, need not heating unit when therefore constructing at the scene.(iv) Yi Qian MPEG modification nonionic solidifying agent does not need high boiling solvent, dispersed very poor in host, and in the present invention with the host excellent dispersion, and also have the function of film coalescence aid as the high boiling solvent of the viscosity depressant of polyfunctional group polyisocyanates composition.(v) the additive as main component of the present invention is not special, expensive starting material, but the emulsifying agent of the anionic property as the dialkyl group Sodium succisulfosuccinate is the common raw material of selling on the market, can be more cheaply, obtain easily.
[0013] yet, no matter at each patent documentation of 0006 section record as prior art, still further check other patent documentations, the glossiness of filming for the lining that improves binary liquid shape aqueous polyurethane based resin composition, can't see at all and cooperate the technical characterictic that adds the such anionic emulsifier of dialkyl group Sodium succisulfosuccinate, also can't see possess above-mentioned (i)～(v) the technical scheme of described characteristic can not at all be showed These characteristics.
[0014] creation process of the present invention and peculiar technical characterictic of the present invention and special feature have been summarized more than, thereby the integral body of scanning this invention constitutes and when putting down in writing clearly, the present invention is made of following invention unit group, to invent [1] as invention substantially, invention below it is other modes of basic invention, or as the invention unit of embodiment.(the invention group all is referred to as " the present invention ".)
[0015] [1] a kind of binary liquid shape aqueous polyurethane based resin composition, it is characterized in that, contain as (A) composition: make (a) diisocyanate cpd and (b) have the lipid acid of active hydrogen group and (c) cooperating polyfunctional group polyisocyanate compound and succinate class sulfonate in the polyurethane prepolymer that polyol compound reaction obtains, carry out the aqueous polyurethane resinoid that transfer reaction obtains after the neutralizing treatment, contain: can be scattered in the polyfunctional group polyisocyanate compound in (A) composition as (B) composition.
[2] a kind of binary liquid shape aqueous polyurethane based resin composition, it is characterized in that, contain as (A) composition: make (a) diisocyanate cpd and (b) have the lipid acid of active hydrogen group and (c) cooperating the polyfunctional group polyisocyanate compound in the polyurethane prepolymer that polyol compound reaction obtains, carry out the polyurethanes resin that transfer reaction obtains after the neutralizing treatment, contain: can be scattered in polyfunctional group polyisocyanate compound and succinate class sulfonate in (A) composition as (B) composition.
As [1] or [2] described binary liquid shape aqueous polyurethane based resin composition, it is characterized in that [3] succinate class sulfonate is the dialkyl group Sodium succisulfosuccinate, and the carbonatoms of alkyl is 6～30.
[4] as [1] or [3] described binary liquid shape aqueous polyurethane based resin composition, it is characterized in that,, cooperate 0.3～3.5 mass parts succinate class sulfonate with respect to water-based polyurethane resin dispersion 100 mass parts of (A) composition.
[5] as each described binary liquid shape aqueous polyurethane based resin composition of [1]～[4], it is characterized in that, (a) diisocyanate cpd is the aliphatic diisocyanate compound, (b) lipid acid with active hydrogen group is dihydroxymethyl lipid acid, (c) polyol compound is that number-average molecular weight is 800～6000 polyester glycol or polycarbonate diol or polyether glycol, the polyfunctional group polyisocyanate compound is HDI trimerization build polyisocyanates or HDI allophanate type polyisocyanates, and transfer reaction utilizes water or amine to carry out.
[6] as each described binary liquid shape aqueous polyurethane based resin composition of [1]～[5], it is characterized in that (B) composition dilutes by high boiling solvent, under the form of coating agent, make the aqueous resin composition ambient cure.
[7] a kind of binary liquid shape water-based polyurethane cold coating composition is characterized in that, each described binary liquid shape aqueous polyurethane based resin composition of [1]～[6] contains the coating additive.
[8] as [7] described water-based polyurethane cold coating composition, it is characterized in that, coating composition be the aqueous polyurethane resinoid of (A) composition and (B) two components as the polyfunctional group polyisocyanate compound of solidifying agent of composition become cover material, when using, two components are mixed as coating.
[9] as the manufacture method of [1] or [3] described binary liquid shape aqueous polyurethane based resin composition, it is characterized in that, make (A) composition and the polyfunctional group polyisocyanate compound that can be scattered in (A) composition of conduct (B) composition become composition set, wherein said (A) composition is to make (a) diisocyanate cpd, (b) have the lipid acid of active hydrogen group and (c) polyol compound reaction, form polyurethane prepolymer, cooperate polyfunctional group polyisocyanate compound and succinate class sulfonate, utilize neutralizing agent to carry out carrying out transfer reaction after the neutralizing treatment, form the aqueous polyurethane resinoid and be used as (A) composition.
The invention effect
[0016] the present invention is the aqueous polyurethane based resin composition; it is not basically not with an organic solvent; therefore environment protection, operational security etc. are no problem, and Financial cost also improves, and the glossiness that lining is filmed improves; in addition; owing in host and other compositions, all cooperate the polyfunctional group polyisocyanate compound, therefore, can further improve the hardness that lining is filmed; on the other hand, do not damage the storage stability of resin combination yet.
In addition, the aqueous polyurethane based resin composition is a binary liquid shape, therefore, mix in the time of can being coated with construction at the use scene, thereby storage-stable can be guaranteed construction, do not use mixing and blending machine and utilize hand mixing just mix can be easily with the high boiling solvent of other compositions disperse the polyfunctional group polyisocyanates equably dispersing and mixing in host, owing to be normal temperature cured type, so need not heating unit when constructing at the scene.
Embodiment
[0017] as the scheme that solves problem of the present invention, above is described, below explains aforesaid of the present invention group embodiment according to basic comprising of the present invention.
[0018] the 1. starting material of aqueous urethane resin composition
(1) diisocyanate cpd
Use the organic diisocyanate compound as the vulcabond composition that the present invention uses, wherein, can use common material, do not have special stipulation as the urethane resin starting material.In addition, for fear of applying tunicle owing to UV-induced xanthochromia, aliphatics or alicyclic diisocyanate are than aromatic diisocyanate more preferably.
[0019] can enumerate tetramethylene diisocyanate particularly, hexamethylene diisocyanate, lysinediisocyanate, 2-methylpentane-1, the 5-vulcabond, 3-methylpentane-1, the 5-vulcabond, 2,2,4-tri-methyl hexamethylene-1, the 6-vulcabond, 2,4,4-tri-methyl hexamethylene-1, aliphatic diisocyanates such as 6-vulcabond can also be enumerated isophorone diisocyanate, cyclohexyl diisocyanate, the hydrogenation eylylene diisocyanate, hydrogenated diphenyl methane diisocyanate, alicyclic diisocyanates such as hydrogenation trimethylammonium eylylene diisocyanate.These vulcabond can use separately to mix more than a kind or 2 kinds and use.As aromatic diisocyanate, can enumerate 2,4 toluene diisocyanate, 2,6-tolylene diisocyanate, dimethylbenzene-1,4-vulcabond, dimethylbenzene-1,3-vulcabond, 4,4 '-diphenylmethanediisocyanate, 2,4 '-diphenylmethanediisocyanate, 4,4 '-diphenyl ether vulcabond, 2,2 '-diphenyl propane-4,4 '-vulcabond, metaphenylene vulcabond, to phenylene vulcabond, naphthylidene-1,4-vulcabond etc.
In addition, can also use the allophanate-modified polyisocyanates that makes with monohydroxy-alcohol to be these adducts modification bodies of representative, carbodiimide modified body, allophanate-modified body, biuret modified body, urea diketone (Uretdione) modification body, uretonimine-modified body, isocyanurate-modified body etc. by hexamethylene diisocyanate and carbonatoms 1～6.
[0020] (2) have the lipid acid of active hydrogen group
This lipid acid has active hydrogen group, for example active hydrogen group of two ends and isocyanic ester radical reaction and embed the main chain of prepolymer, and the free carboxyl is hydrophilic, thereby plays the effect that improves the prepolymer water dispersible.
As fatty acid cpds with active hydrogen group, can enumerate dimethylol propionic acid with two terminal hydroxyls, dimethylolpropionic acid as typical example, other can also enumerate the reactant of polyamines and acid anhydrides, are lactone affixture of initiator etc. with dimethylol propionic acid, dimethylolpropionic acid etc.
As this lipid acid, preferred dimethylol propionic acid and dimethylolpropionic acid.
[0021] (3) polyol compound
Polyol compound of the present invention is diol compound and three alkylol cpds etc., polyhydroxy reactant as the present invention's use, main polyester polyol, polycarbonate polyol or the polyether glycol etc. of using, wherein can use raw-material ordinary matter, not special regulation as urethane resin.
Preferred number average molecular weight is 800～6000 material, enumerates glycol polypropylene (PPG), polytetramethylene ether diol (PTMG) etc. typically.Moreover the mensuration of number-average molecular weight is by carrying out as the GPC method of standard with polystyrene as usual way.
[0022] more particularly, as polyester polyol, can use phthalic acid, m-phthalic acid, terephthalic acid, naphthalene dicarboxylic acids, succsinic acid, tartrate, propanedioic acid, oxalic acid, pentanedioic acid, hexanodioic acid, pimelic acid, nonane diacid, 1, the 4-cyclohexyl dicarboxylic acid, α-hydromuconic acid (Hydromuconic Acid), β-hydromuconic acid, α, β-diethyl succsinic acid, toxilic acid, fumaric acid, other diprotic acid etc. are more than a kind or 2 kinds and ethylene glycol, 1, the 2-propylene glycol, 1, ammediol, 1, the 2-butyleneglycol, 1, the 3-butyleneglycol, 1, the 4-butyleneglycol, 1, the 5-pentanediol, 1, the 6-hexylene glycol, 1, the 8-ethohexadiol, 1, the 9-nonanediol, the 3-methyl isophthalic acid, the 5-pentanediol, 3,3-dihydroxymethyl heptane, Diethylene Glycol, dipropylene glycol, neopentyl glycol, hexanaphthene-1, the 4-glycol, hexanaphthene-1, the 4-dimethanol, the oxyethane of dihydroxyphenyl propane, affixtures such as propylene oxide, two (beta-hydroxyethyl) benzene, xylyl alcohol, other glycol or glycerine, TriMethylolPropane(TMP), the polyester polyol that the polycondensation of polyalcohols such as tetramethylolmethane obtains.
[0023] in addition, can also enumerate 6-caprolactone, alkyl and replace the polyester polyol that 6-caprolactone, δ-Wu Neizhi, alkyl replace the lactone that cyclic ester monomeric ring-opening polymerizations such as (lactones) such as δ-Wu Neizhi obtain, can also use a part with low molecular polylol to become the polyesteramide polyvalent alcohol etc. of low molecule amine such as hexamethylene-diamine, isophorone diamine, monoethanolamine, low molecule amino alcohol.
[0024] as polyether glycol, can use with as 0022 section described glycols, polyalcohols or they and quadrol, propylene diamine, tolylene diamine, mphenylenediamine, the ditan diamines, amines such as benzene dimethylamine have more than 2 like that, the compound of preferred 2～3 active hydrogen groups is as initiator, and addition polymerization is oxyethane more than a kind or 2 kinds, propylene oxide, alkylene oxides such as butylene oxide ring, methyl glycidyl ether, alkyl or aryl Racemic glycidol ethers such as phenyl glycidyl ether, the polyether glycol that ring-type ethers monomers such as tetrahydrofuran (THF) etc. obtain.
[0025], can use the polycarbonate polyol that obtains by reaction as low-molecular-weight diol class, low molecule triol and ethylene carbonate (Ethylene carbonate), diethyl carbonate, diphenyl carbonate etc. as described in 0022 section as polycarbonate polyol.In addition, the polyvalent alcohol that can also suitably use the transesterify by polycarbonate polyol and polyester polyol to generate.
[0026] other can also use the polyol that made by polyether glycol and omega-dicarboxylic acids and by the polyester ether polylol that the reaction of polyester, polycarbonate and epoxide, cyclic ether obtains, and can also use to have polyolefin polyhydric alcohol 2 above hydroxyls, polyhutadiene, hydrogenated butadiene polymer, polyisoprene, hydrogenated polyisoprene etc.
[0027] (4) succinate class sulfonate
Succinate class sulfonate is main component of the present invention, confirms by the contrast with each embodiment described later and each comparative example: can improve the gloss that the lining of aqueous polyurethane based resin composition is filmed significantly.
As succinate class sulfonate, specifically, can suitably use the dialkyl group Sodium succisulfosuccinate.
By this additive, high boiling solvent disperses the dispersiveness of the relative host composition of multifunctional polyisocyanate compound to improve, and the particle diameter of this compound also diminishes, and the gloss that lining is filmed increases.
[0028] water-based polyurethane resin dispersion 100 mass parts of relative (A) composition cooperate 0.3～3.5 mass parts succinate class sulfonate, preferably cooperate 0.5～3.0 mass parts.If be lower than 0.3 mass parts, the effect that gloss improves will be low excessively, if surpass 3.5 mass parts, the effect that gloss improves can not increase, and other rerum naturas such as the water tolerance of filming, alkali resistance can reduce.These facts are confirmed by the contrast of each embodiment described later and each comparative example.
In addition, table 1 described later, 2 additive are the mixtures of 70% additive, 15% propylene glycol and 15% water, and the digital actual effect of the use level of the additive in the table accounts for 7 one-tenth (* 0.7).
[0029] if not the sulfonate of succinate class sulfonate, but alkoxyl group PEG sulfonate sodium, polyoxyethylene in each comparative example described later encircle the phenyl ether sulfonate sodium more, as shown in Table 2, and the effect that the gloss that almost can not obtaining is covered films improves.
Additive of the present invention is not special, expensive raw material, and the dialkyl group Sodium succisulfosuccinate is the common raw materials of selling as emulsifying agent, obtains relatively cheaply and easily.Wherein, the carbonatoms of alkyl is 6～30, is suitable for 8～24 (commercially available products etc.).
The dialkyl group Sodium succisulfosuccinate is commodity Newcol 291-PG by name for example, sell the mixture that it is made up of 70% dialkyl group Sodium succisulfosuccinate (carbonatoms of alkyl is 8～24 mixture), 15% propylene glycol and 15% water by Japanese emulsifying agent Co., Ltd..
[0030] chemical formula as the dioctyl Sodium succisulfosuccinate of the typical example of dialkyl group Sodium succisulfosuccinate is H
17C
8OOC-CH (SO
3Na) CH
2-COOC
8H
17, structural formula is:
[Chemical formula 1]
[0031] (5) high boiling solvent
High boiling solvent of the present invention is the viscosity for the polyfunctional group polyisocyanates gradation composition of other composition solidifying agent that reduce binary liquid shape, and improve the film-forming properties of filming that is covered and use, because high boiling solvent has reduced the dispersing and mixing when the polyfunctional group polyisocyanates gradation composition interpolation of other compositions of binary liquid shape is mixed in the host composition.By adding succinate class sulfonate additive, stoped the decline of this dispersing and mixing, improved dispersing and mixing on the contrary, form principal character of the present invention and effect.
High boiling solvent is preferably to have and is higher than toluene (boiling point: the organic solvent of boiling point 110 ℃ of normal pressures), NMP (N-Methyl pyrrolidone), polyoxyethylene glycol kind solvent are suitable.As the typical example of polyoxyethylene glycol kind solvent, can enumerate PMA (propyleneglycol monomethyl acetates).
[0032] (6) chain propagation agent
Diamines or polyamine compounds are compared as chain propagation agent with diol compound as the chain propagation agent of prepolymer, and easier generation is high crosslinked, and therefore, physical properties excellent such as water tolerance, solvent resistance and stain resistance also can be water as chain propagation agent.
As with the reaction host of diisocyanate cpd reaction, if use diamines or triamine compound to substitute glycol because therefore the hyperergy of these amine compound can not form prepolymer, thereby, with the chain propagation agent of these amine compound as prepolymer.
For the object lesson of these amine compound, diamines can be enumerated quadrol (EDA), isophorone diamine (IPDA) etc., and polyamines can be enumerated with H
2N-(C
2H
4NH)
n-C
2H
4NH
2The diethylenetriamine (DETA) of (n=1～8) expression, Triethylenetetramine (TETA), tetren, penten etc.
[0033] (7) curing catalysts
Use the resinifying catalyzer (urethane catalyzer) of curing catalysts (polymerizing catalyst) as required as urethane reaction, can use such metal species catalyzer of dibutyl tin laurate, zinc naphthenate or Triethylene Diamine, the such common curing catalysts such as amines catalyst of N-methylmorpholine, can increase speed of response, reduce temperature of reaction.
[0034] (8) solidifying agent
As the solidifying agent that makes curable urethane resin, the present invention can use the liquid of polyfunctional group polyisocyanate compound as solidifying agent in the host composition and two liquid system (composition of binary liquid shape).Owing to use in two kinds of components, therefore, the bridging property of filming is higher, and rerum natura improves.
Can enumerate urethane modification body, urea modification body, allophanate-modified body, biuret modified body, urea diketone modification body, isocyanurate-modified body of organic diisocyanate class etc. particularly.For the solidifying agent of the isocyanurate-modified body type that is derived from hexamethylene diisocyanate (HDI), the mol ratio of the NH of the NCO/ host of preferred consolidation agent is 2.5～4.5 material.
More particularly, the polyfunctional group polyisocyanate compound is HDI trimerization build polyisocyanates or HDI allophanate type polyisocyanates, use NCO base in 1 molecule be derived from hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI) be more than 3 tripolymer, add zoarium.
[0035] (9) other auxiliary agents
In the present invention, except 0032 section described polyamine compounds, as required, can also use the chain propagation agent in the common polyaddition reaction.
As chain propagation agent, can also use common low molecular compound with 2 above active hydrogen groups, can make spent glycol, propylene glycol, 1 particularly, 4-butyleneglycol, 1, the allophanate-modified body of the isocyanurate-modified body of 5-pentanediol, neopentyl glycol, diethanolamine, trolamine and HDI, vulcabond etc.
[0036] in addition, in order further to improve rerum natura, and increase various rerum naturas, as various additives, especially the coating additive can also use fire retardant, softening agent, antioxidant, UV light absorber, dyestuff, pigment, weighting agent, internal mold release, supporting material, matting agent, electroconductibility imparting agent, charged control agent, static inhibitor, lubricant and other processing aids.
[0037] 2, aqueous polyurethane based resin composition
(1) host and solidifying agent
Aqueous urethane resin composition of the present invention is the basic binary liquid shape that is made of (B) composition of host (A) composition and curing agent component (multifunctional polyisocyanate compound), can also cooperate solidifying agent in host, further forms high crosslinked.
(A) composition of host, be to make (a) diisocyanate cpd and (b) have the lipid acid of active hydrogen group and (c) is cooperating polyfunctional group polyisocyanate compound and succinate class sulfonate in the prepolymer that polyol compound reaction generates, after neutralizing treatment, carrying out the aqueous polyurethane resinoid of transfer reaction generation.
In addition, as the aqueous polyurethane resinoid,, can also use and with such other of acrylic resin, olefine kind resin resinous principle and mix the material that obtains arbitrarily according to purposes.
As (B) composition, be can be scattered in (A) composition contain solidifying agent, the high boiling solvent dispersion.(B) composition of solidifying agent, be can be scattered in (A) composition, with the aforementioned HDI tripolymer polyfunctional group polyisocyanate compound that is representative.In addition, succinate class sulfonate can also be matched with in (B) composition.Storage stability reduces slightly in the case.
Proportion of composing is preferably: roughly with respect to 100 mass parts (A) composition, cooperate (B) composition about 20 mass parts, make that are solidifying agent about in one's duty 16 mass parts of this 20 quality, are high boiling solvents about 4 mass parts, but are not particularly limited.
[0038] (2) are as the form of composition
Aqueous polyurethane based resin composition of the present invention is as mentioned above by as (A) composition of host and (B) two liquid system that constitute of the solidifying agent of composition, as the form of using is that two components such as binary liquid shape coating composition become cover material, during as coating etc., two components are mixed, utilize the polyfunctional group NCO compound of solidifying agent to carry out three-dimensional curing.
The aqueous polyurethane based resin composition is a binary liquid shape, therefore mix in the time of can being coated with construction at the use scene, thereby storage-stable can be guaranteed construction, do not use mixing and blending machine and utilize hand mixing just mix can be easily with as the high boiling solvent dispersion polyfunctional group polyisocyanates of other compositions equably dispersing and mixing in host, owing to be normal temperature cured type, need not heating unit when therefore constructing at the scene.
In general, the meaning of coating composition is not unique, in the present invention, is not to be pre-mixed the composition that whole compositions obtain, but makes the composition that two components become cover material.
[0039] the 3. manufacture method of aqueous polyurethane based resin composition
The manufacturing of aqueous polyurethane based resin composition of the present invention is undertaken by following steps: in order to form (A) composition, make (a) diisocyanate cpd that forms the polyurethane prepolymer main chain, (b) that be used to give the water dispersible composition has the lipid acid of active hydrogen group, and (c) polyol compound reaction that forms the polyurethane prepolymer main chain, generate the terminal isocyanate prepolymer, then, cooperation is as the polyfunctional group polyisocyanate compound and the succinate class sulfonate that is used to improve coating film gloss of solidifying agent, utilize neutralizing agents such as tertiary amine that the carboxyl of lipid acid is carried out neutralizing treatment then, make it to be scattered in the aqueous solution with chain propagation agents such as polyamines and become water-based, after neutralizing treatment, carry out transfer reaction, form the aqueous polyurethane resinoid, at last with (B) composition that can be scattered in (A) composition, promptly form composition set together as the such polyfunctional group polyisocyanate compound of HDI tripolymer that is scattered in the solidifying agent of high boiling solvent.
In addition, when in (B) composition, cooperating succinate class sulfonate, in above-mentioned polyurethane-reinforcement reaction, do not add cooperation, and in (B) composition, cooperate.
[0040] the 4. purposes of aqueous polyurethane based resin composition
As the purposes of aqueous polyurethane based resin composition of the present invention, can be used as coating agent, especially be suitable as coating.
It is suitable using base material, timber as covering with paint, also can use metal, plastic material or inorganic materials etc.Especially be suitable for woodworks such as a material, glossiness, hardness and excellent in abrasion resistance were compared with former acrylic coating, and the elastic performance of urethanes is good, if use polycarbonate-based polyvalent alcohol as polyhydroxy reactant, photostabilization also improves.
Embodiment
[0041] utilize embodiment and comparative example to compare below, more detailed, represent the present invention particularly, make formation of the present invention more clear, confirm the reasonableness, importance of each technical characterictic that the present invention constitutes and for the distinguishing feature of prior art.
[0042] [synthesizing of host 3: the manufacturing of aqueous polyurethane emulsion]
In the reactor of the capacity 1000ml that stirrer, thermometer, nitrogen-sealed pipe and condenser are installed, add 348.4g polyvalent alcohol 2 (annotating *), 25.8g2,2-dimethylol propionic acid (DMPA), 118g dipropylene glycol dme (DMDPG) were 90 ℃ of following heating for dissolving 10 minutes.After being cooled to 60 ℃, add 256.6g hydrogenated diphenyl methane diisocyanate (HMDI), 0.04g two lauric acid dioctyl tins (DOTDL), reaction is 2 hours under 80 ℃, makes to contain the terminal pre-polymer solution of carboxyl isocyanate group.The isocyanate content of this pre-polymer solution is 3.07%, and the carboxylic acid import volume in the prepolymer is 0.75mmol/g.
Then, add 39.4gHDI class tripolymer, 11.8g dialkyl group succinate sodium sulfonate (R=8～24), mix equably, add 38.1g triethylamine (TEA) then, in and carboxyl after, add 875g water while stirring, carry out emulsification, under 30 ℃, utilize water to carry out 12 hours transfer reaction.In reaction, confirm to have produced carbon dioxide.
When utilizing FT-IR to confirm that isocyanate group does not exist, finish reaction, make the aqueous polyurethane resin dispersion of host 3.The solids component of host 3 is 35%.
[0043] in addition, be meant by 1 (*) that the number-average molecular weight that 6-hexylene glycol and diethyl carbonate make is 2000 polycarbonate polyol.This host 3 is equivalent to the B of the aqueous polyurethane resin dispersion of embodiment 3 in the table 1.
With the synthetic embodiment 1 of synthetic table 1 similarly of above-mentioned host 3 and host 1 and the host 4 (A and the C that are equivalent to the aqueous polyurethane resin dispersion of table 1) of embodiment 4.Host 1 is used by 1, and the number-average molecular weight that 6-hexylene glycol and diethyl carbonate make is 1000 polycarbonate polyol, and host 4 is used the polycarbonate polyol identical with host 3.
[0044] [embodiment 3: the manufacturing of aqueous polyurethane based resin composition]
With respect to the above-mentioned host 3 of 101.5 mass parts, (polyisocyanates B in the table 1 (HDI allophanate type polyisocyanates trade(brand)name: ア Network ア ネ-ト 130)) and 5 mass parts are as the high boiling solvent C (propyleneglycol monomethyl acetates (PMA)) of viscosity depressant to mix 15 mass parts solidifying agent 3, add 20 mass parts water to the gained mixture, in the 500ml beaker, utilize glass stick to stir.
Estimate Combination, on the lauan glued board, carry out 2 coating brushings, placed at normal temperatures 7 days, make the evaluation sample, carry out evaluation test.Be displayed in Table 1 evaluation result etc.
Under table 1 condition, carry out embodiment 1,2,4～7 similarly to Example 3.These evaluation results also are shown in table 1.
In addition, under table 2 and table 3 condition, compare example 1～13 similarly to Example 3.These evaluation results also are shown in table 2 and table 3.
[0045] [measuring method of film performance]
(i) gloss (60 °)
Use the reflection mist degree tester (manufacturing of BYK-Gardner company) of the built-in glossy meter of angular, measure the reflectivity of film coated surface under input angle 60 degree, reflection angle 60 degree.
(ii) pencil hardness
Measure according to the artificial method of drawing that the pencil cut value of JIS K5400 is tested.
(iii) water tolerance
After film coated surface drips a tap water, at room temperature carries out drying, estimate the outward appearance of film coated surface.
(iv) alkali resistance
After film coated surface drips one 5% aqueous sodium carbonate, at room temperature carries out drying, estimate the outward appearance of film coated surface.
(v) alcohol resistance
After film coated surface drips one 50% ethanol liquid, at room temperature carries out drying, estimate the outward appearance of film coated surface.
In addition, (iii)～(metewand of each measurement result v) is as follows.
◎: do not change zero: change, but dry back disappearance △: change, still have after the drying vestige residual *: the dissolving of filming
[0046] [table 1-1]
| Embodiment 1 | Embodiment 2 | Embodiment 3 | Embodiment 4 | Embodiment 5 | Embodiment 6 | Embodiment 7 | |
| [host] | |||||||
| Water system PU resin dispersion A | ?100 | ?100 | ?100 | ?100 | ??100 | ||
| ??????????????????B | ??100 | ||||||
| ??????????????????C | ??100 | ||||||
| (internal crosslinking agent) | |||||||
| A:HDI class tripolymer | ?7 | ?7 | ??8 | ?5 | ?5 | ??5 | |
| B: modification HDI | ??5 | ||||||
| Nonvolatile component (%) | ?35 | ?35 | ??35 | ??35 | ?35 | ?35 | ??35 |
| (anionic property additive (*)) | |||||||
| ??Newcol-291PG | ?1 | ?2 | ??1.5 | ??0.5 | ?2 | ??1.5 | |
| [solidifying agent] | |||||||
| Polyisocyanates A | ?20 | ?20 | ?10 | ??10 | |||
| ????????????B | ?20 | ??15 | ??15 | ||||
| (high boiling solvent) | |||||||
| ??DEDG | ?5 | ??5 | ?5 | ||||
| ??DMDPG | ?5 | ||||||
| ??PMA | ??5 | ?5 | |||||
| ??NMP | ??5 | ||||||
| (anionic property additive) | |||||||
| ??Newcol-291PG | ?1 |
[table 1-2]
| Storage stability | ??○ | ??○ | ??○ | ??○ | ??△ | ??○ | ??○ |
| Combination (the artificial mixing) | ??○ | ??○ | ??○ | ??○ | ??○ | ??○ | ??○ |
| [film performance] | |||||||
| Gloss (60 °) | ??72.3 | ??70.5 | ??77.5 | ??75.0 | ??60.5 | ??65.5 | ??60.0 |
| Pencil hardness | ??F-H | ??H | ??F-H | ??F-H | ??H | ??H | ??H |
| Water tolerance | ??◎ | ??◎ | ??◎ | ??◎ | ??◎ | ??◎ | ??◎ |
| Alkali resistance | ??◎ | ??◎ | ??◎ | ??○ | ??◎ | ??○ | ??○ |
| Alcohol resistance | ??◎ | ??◎ | ??◎ | ??○ | ??◎ | ??○ | ??○ |
[0047] in addition, the label symbol in the table is represented following content.
Modification HDI:MPEG modification HDI class tripolymer, (*): the mixture of 70% anionic property additive and 15% propylene glycol and 15% water, Newcol-291PG: dialkyl group succinate sodium sulfonate (the Japanese emulsifying agents in R=8～24 (strain) manufacturing), Newcol-1305SN: alkoxyl group PEG sodium sulfonate (Japanese emulsifying agent (strain) manufacturing), Newcol-707SF: polyoxyethylene encircles phenyl ether sodium sulfonate (Japanese emulsifying agent (strain) manufacturing) more, polyisocyanates A:HDI class trimerization build polyisocyanates (trade(brand)name ア Network ア ネ-ト 100), polyisocyanates B:HDI class allophanate type polyisocyanates (trade(brand)name ア Network ア ネ-ト 130), DEDG: diethylene glycol diethyl ether, DMDP G: dipropylene glycol dme, PMA: propyleneglycol monomethyl acetates, NMP:N-methyl-2-pyrrolidone
[0048] [table 2-1]
| Comparative example 1 | Comparative example 2 | Comparative example 3 | Comparative example 4 | Comparative example 5 | Comparative example 6 | Comparative example 7 | Comparative example 8 | Comparative example 9 | |
| [host] | |||||||||
| Water system PU resin dispersion A | ??100 | ??100 | ??100 | ??100 | ??100 | ??100 | |||
| ??????????????????B | ??100 | ??100 | |||||||
| ??????????????????C | ??100 | ||||||||
| (internal crosslinking agent) | |||||||||
| A:HDI class tripolymer | ??7 | ??7 | ??8 | ??7 | ??5 | ??8 | ??8 | ??8 | |
| B: modification HDI | ??5 | ||||||||
| Nonvolatile component (%) | ??35 | ??35 | ??35 | ??35 | ??35 | ??35 | ??35 | ??35 | ??35 |
| (anionic property additive) | |||||||||
| ??Newcol-291PG | ??0.2 | ??5 | |||||||
| ??Newcol-1305SN | ??1 | ||||||||
| ??Newcol-707SF | ??1 | ||||||||
| [solidifying agent] | |||||||||
| Polyisocyanates A | ??20 | ??20 | ??20 | ||||||
| ????????????B | ??20 | ??20 | ??20 | ??20 | |||||
| (high boiling solvent) | |||||||||
| ??DEDG | ??5 | ??5 | |||||||
| ??DMDPG | ??5 | ||||||||
| ??PMA | ??5 | ||||||||
| ??NMP | ??5 | ??5 | |||||||
| The anionic property additive | |||||||||
| ??Newcol-291PG | ??2 |
[table 2-2]
| Storage stability | ??○ | ??○ | ??- | ??- | ??× | ??○ | ??○ | ??○ | ??○ |
| Combination (the artificial mixing) | ??○ | ??○ | ??- | ??- | ??- | ??× | ??○ | ??○ | ??○ |
| [film performance] | |||||||||
| Gloss (60 °) | ??30.0 | ??78.0 | ??77.0 | ??76.0 | ??- | ??65.0 | ??38.0 | ??35.5 | ??25.5 |
| Pencil hardness | ??F | ??HB-F | ??H | ??F-H | ??- | ??F | ??F | ??F | ??F |
| Water tolerance | ??◎ | ??△ | ??△ | ??× | ??- | ??○ | ??◎ | ??◎ | ??◎ |
| Alkali resistance | ??○ | ??△ | ??△ | ??× | ??- | ??△ | ??○ | ??○ | ??○ |
| Alcohol resistance | ??○ | ??△ | ??△ | ??× | ??- | ??△ | ??○ | ??○ | ??△ |
[0049] [table 3-1]
| Comparative example 10 | Comparative example 11 | Comparative example 12 | Comparative example 13 | |
| [host] | ||||
| Water system PU resin dispersion A | ??100 | ??100 | ??100 | ??100 |
| ??????????????????B | ||||
| ??????????????????C | ||||
| (internal crosslinking agent) | ||||
| A:HDI class tripolymer | ??8 | ??8 | ??8 | ??8 |
| B: modification HDI | ||||
| Nonvolatile component (%) | ??35 | ??35 | ??35 | ??35 |
| (anionic property additive) | ||||
| ??Newcol-293 ＊1 | ??1 | |||
| ??Newcol-220L ＊2 | ??1 | |||
| (nonionic additive) | ||||
| ??Newcol-170 ＊3 | ??1 | |||
| ??Newcol-20F ＊4 | ??1 | |||
| [solidifying agent] | ||||
| Polyisocyanates A | ||||
| ????????????B | ??20 | ??20 | ??20 | ??20 |
| (high boiling solvent) | ||||
| ??DEDG | ||||
| ??DMDPG | ??5 | ??5 | ??5 | ??5 |
| ??PMA | ||||
| ??NMP | ||||
| (anionic property additive) | ||||
| ??Newcol-291PG |
[table 3-2]
| Storage stability | ??○ | ??○ | ??○ | ??○ |
| Combination (the artificial mixing) | ??○ | ??○ | ??○ | ??× |
| [film performance] | ||||
| Gloss (60 °) | ??10.4 | ??15.5 | ??5.4 | ??36.0 |
| Pencil hardness | ??F | ??F | ??F | ??HB-F |
| Water tolerance | ??○ | ??◎ | ??◎ | ??◎ |
| Alkali resistance | ??△ | ??◎ | ??◎ | ??◎ |
| Alcohol resistance | ??△ | ??○ | ??○ | ??○ |
[0050] in addition, in table 1,
*1: monoalkyl succinate class disodium sulfonate effective constituent 40%
*2: Sodium dodecylbenzene sulfonate effective constituent 65%
*3: polyoxyethylene oleic acid ester effective constituent 99%
*4: polyoxyethylene anhydrous sorbitol laurate effective constituent 99%
[0051] [outcome research of embodiment and comparative example]
By contrasting above each embodiment and each comparative example, clear and definite following aspect content.In the present invention, all satisfy formation technical characterictic of the present invention, in binary liquid shape aqueous polyurethane based resin composition, use the outside linking agent of the internal crosslinking agent of host composition and other compositions and degree of crosslinking is uprised, therefore, the hardness of film according to pencil hardness as film performance is good, and water tolerance, alkali resistance and alcohol resistance etc. are all very excellent.Utilize high boiling solvent to dilute outside linking agent, therefore, Combination (the artificial mixing) is excellent naturally, on the other hand, owing to carry out the high boiling solvent dilution, also use the dialkyl group Sodium succisulfosuccinate as the anionic property additive, therefore, the gloss as film performance significantly improves.
In addition, in embodiment 5, do not have host, aspect other compositions, cooperate the anionic property additive, therefore, compare with other embodiment, storage stability reduces slightly, and for all embodiment, each film performance is all very outstanding, and storage stability does not reduce yet.
[0052] in each comparative example, do not satisfy formation technical characterictic of the present invention fully, therefore to compare with each embodiment, coating property, film performance be variation all.
In comparative example 1, use inside and outside linking agent, so hardness of film etc. is functional, still, the use level of anionic property additive is not enough, and therefore, the gloss of filming does not improve.In comparative example 2, the use level of anionic property additive is excessive, and therefore the gloss of filming improves, and still, because additive is excessive, causes water tolerance, alkali resistance and alcohol resistance to reduce.In comparative example 3,4, do not use outside linking agent, the gloss of filming naturally can not reduce, still, the film performance variation of water tolerance, alkali resistance and alcohol resistance and so on.In comparative example 5, aspect other compositions, add the anionic property additive, use level is also many slightly, and therefore, the storage stability of the solidifying agent of binary liquid shape is damaged.In comparative example 6, do not use high boiling solvent, natural gloss is good, still, the Combination variation.In comparative example 7,8, use inside and outside linking agent, hardness of film etc. are functional, still, as the anionic property additive, do not use sulphosuccinates and use other additives, and therefore the gloss as film performance does not improve.In comparative example 9, use inside and outside linking agent, so performance such as hardness of film there is not variation, still, and owing to do not use the anionic property additive, the therefore gloss of the filming non-constant that becomes.
Therefore [0053] in comparative example 10, use inside and outside linking agent, functional as hardness of film, but, effective constituent amount as the sulphosuccinates of anionic property additive is few, so the gloss of film performance is very low, and the chemical proofing of filming is also low.In comparative example 11, use inside and outside linking agent, so film performance is good, still,, do not use sulphosuccinates and use other additives as the anionic property additive, therefore very low as the gloss of film performance.In comparative example 12, use inside and outside linking agent, film performance is good, still, as the anionic property additive, does not use sulphosuccinates and uses the nonionic additive, and is therefore, very low as the gloss of film performance.In comparative example 13, use inside and outside linking agent, film performance is good, still, as the anionic property additive, does not use sulphosuccinates and uses the nonionic additive, and therefore, Combination is poor, and is low as the gloss of film performance.
[0054] studies by above data results and contrast thereof, can confirm the reasonableness and the validity of formation technical characterictic of the present invention, can think that the present invention compared with prior art, has significant advantage.
Utilizability on the industry
[0055] the present invention is the aqueous polyurethane based resin composition; basically not with an organic solvent; therefore environmental protection, operational security etc. are no problem; financial cost also improves; the glossiness that coating is filmed improves, and in addition, can further improve the hardness that coating is filmed; on the other hand, do not damage the storage-stable of resin combination yet.
Further, the aqueous polyurethane based resin composition is two-liquid type, therefore, mix in the time of can being coated with at the use scene construction, thereby storage-stable can be protected and guarantee construction, do not use mixing and blending machine and utilize just manually to mix and can be easily disperse the polyfunctional group polyisocyanates to disperse equably to be mixed in the host high boiling solvent of other compositions, owing to be normal temperature cured type, need not heater when therefore constructing at the scene.
Therefore, aqueous polyurethane based resin composition of the present invention especially can be at industrial coating material as lining material, especially site operation in the various technical fields.
Claims (9)
1. binary liquid shape aqueous polyurethane based resin composition, it is characterized in that, contain as (A) composition: make (a) diisocyanate cpd and (b) have the lipid acid of active hydrogen group and (c) cooperating polyfunctional group polyisocyanate compound and succinate class sulfonate in the polyurethane prepolymer that polyol compound reaction obtains, carry out the aqueous polyurethane resinoid that transfer reaction obtains after the neutralizing treatment, contain: can be scattered in the polyfunctional group polyisocyanate compound in (A) composition as (B) composition.
2. binary liquid shape aqueous polyurethane based resin composition, it is characterized in that, contain as (A) composition: make (a) diisocyanate cpd and (b) have the lipid acid of active hydrogen group and (c) cooperating the polyfunctional group polyisocyanate compound in the polyurethane prepolymer that polyol compound reaction obtains, carry out the polyurethanes resin that transfer reaction obtains after the neutralizing treatment, contain: can be scattered in polyfunctional group polyisocyanate compound and succinate class sulfonate in (A) composition as (B) composition.
3. binary liquid shape aqueous polyurethane based resin composition according to claim 1 and 2 is characterized in that succinate class sulfonate is the dialkyl group Sodium succisulfosuccinate, and the carbonatoms of alkyl is 6～30.
4. according to claim 1 or 3 described binary liquid shape aqueous polyurethane based resin compositions, it is characterized in that,, cooperate 0.3～3.5 mass parts succinate class sulfonate with respect to water-based polyurethane resin dispersion 100 mass parts of (A) composition.
5. according to each described binary liquid shape aqueous polyurethane based resin composition of claim 1～4, it is characterized in that, (a) diisocyanate cpd is the aliphatic diisocyanate compound, (b) lipid acid with active hydrogen group is dihydroxymethyl lipid acid, (c) polyol compound is that number-average molecular weight is 800～6000 polyester glycol or polycarbonate diol or polyether glycol, and the polyfunctional group polyisocyanate compound is HDI trimerization build polyisocyanates or HDI allophanate type polyisocyanates.
6. according to each described binary liquid shape aqueous polyurethane based resin composition of claim 1～5, it is characterized in that (B) composition dilutes by high boiling solvent, under the form of coating agent, make the aqueous resin composition ambient cure.
7. a binary liquid shape water-based polyurethane cold coating composition is characterized in that, each described binary liquid shape aqueous polyurethane based resin composition of claim 1～6 contains the coating additive.
8. water-based polyurethane cold coating composition according to claim 7, it is characterized in that, coating composition be the aqueous polyurethane resinoid of (A) composition and (B) two components as the polyfunctional group polyisocyanate compound of solidifying agent of composition become cover material, when using, two components are mixed as coating.
9. the manufacture method of claim 1 or 3 described binary liquid shape aqueous polyurethane based resin compositions, it is characterized in that, make (A) composition and the polyfunctional group polyisocyanate compound that can be scattered in (A) composition of conduct (B) composition become composition set, wherein said (A) composition is to make (a) diisocyanate cpd, (b) have the lipid acid of active hydrogen group and (c) polyol compound reaction, form polyurethane prepolymer, cooperate polyfunctional group polyisocyanate compound and succinate class sulfonate, utilize neutralizing agent to carry out carrying out transfer reaction after the neutralizing treatment, form the aqueous polyurethane resinoid and be used as (A) composition.
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| PCT/JP2008/053795 WO2008108346A1 (en) | 2007-03-02 | 2008-03-03 | Water-based polyurethane resin composition and coating composition comprising the same |
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| CN107615224A (en) * | 2015-06-09 | 2018-01-19 | 旭化成株式会社 | The manufacture method and touch panel display device of touch panel aqueous resin composition, transfer film and solidifying film layer stack and resin pattern |
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| JP5912588B2 (en) * | 2012-01-31 | 2016-04-27 | 第一工業製薬株式会社 | Method for producing aqueous polyurethane resin composition |
| EP3015486B1 (en) * | 2013-06-27 | 2018-11-07 | Asahi Kasei Kabushiki Kaisha | Polyisocyanate composition and method for production thereof, block polyisocyanate composition and method for production thereof, resin composition, curable resin composition, and cured article |
| KR101714740B1 (en) * | 2016-05-17 | 2017-03-09 | 주식회사 노루알앤씨 | Aqueous peelable paint composition including polyurethane water-dispersion |
| KR102109975B1 (en) | 2018-11-16 | 2020-05-28 | (주)진주에스이씨 | Water-base Urethane resin emulsion composion for Pollution prevention |
| KR102172886B1 (en) * | 2019-06-07 | 2020-11-02 | 애경특수도료 주식회사 | Paint against scattering glass |
| CN110776817A (en) * | 2019-10-29 | 2020-02-11 | 河北晨阳工贸集团有限公司 | Water-based color-changing heat-insulating glass paint and preparation method thereof |
| KR102420431B1 (en) | 2022-03-17 | 2022-07-14 | 한서포리머주식회사 | Water-soluble top-coating composition of two-component type |
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| DE10152294A1 (en) | 2001-10-26 | 2003-05-08 | Solutia Austria Gmbh Werndorf | High molecular weight polyurethane dispersions |
| JP4173317B2 (en) * | 2002-01-29 | 2008-10-29 | アキレス株式会社 | Two-component water-based urethane resin adhesive for dry lamination |
| JP4360205B2 (en) * | 2004-01-07 | 2009-11-11 | 日本ポリウレタン工業株式会社 | Method for producing polyurethane emulsion for aqueous one-component coating agent |
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| CN101627068B (en) | 2012-05-23 |
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