JP2022508013A - 2成分ポリウレタン組成物 - Google Patents
2成分ポリウレタン組成物 Download PDFInfo
- Publication number
- JP2022508013A JP2022508013A JP2021511589A JP2021511589A JP2022508013A JP 2022508013 A JP2022508013 A JP 2022508013A JP 2021511589 A JP2021511589 A JP 2021511589A JP 2021511589 A JP2021511589 A JP 2021511589A JP 2022508013 A JP2022508013 A JP 2022508013A
- Authority
- JP
- Japan
- Prior art keywords
- polyurethane composition
- emulsion polymer
- weight
- structural unit
- acrylate
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 108
- 239000004814 polyurethane Substances 0.000 title claims abstract description 52
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 52
- 239000000178 monomer Substances 0.000 claims abstract description 81
- 239000004908 Emulsion polymer Substances 0.000 claims abstract description 65
- 239000004094 surface-active agent Substances 0.000 claims abstract description 38
- 239000006185 dispersion Substances 0.000 claims abstract description 32
- 239000002253 acid Substances 0.000 claims abstract description 28
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 25
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 25
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 18
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 16
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 11
- 239000011574 phosphorus Substances 0.000 claims abstract description 11
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims abstract description 8
- -1 ethoxy, propoxy Chemical group 0.000 claims description 46
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 12
- 239000002245 particle Substances 0.000 claims description 12
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 9
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 8
- 239000000049 pigment Substances 0.000 claims description 8
- 238000007720 emulsion polymerization reaction Methods 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 150000007942 carboxylates Chemical group 0.000 claims description 5
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical group CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 claims description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 5
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 4
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 3
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 3
- 239000012986 chain transfer agent Substances 0.000 claims description 3
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 3
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 claims description 3
- 230000009477 glass transition Effects 0.000 claims description 3
- 235000021317 phosphate Nutrition 0.000 claims description 3
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 claims description 2
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 239000012190 activator Substances 0.000 claims description 2
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 2
- ORTRWBYBJVGVQC-UHFFFAOYSA-N hexadecane-1-thiol Chemical compound CCCCCCCCCCCCCCCCS ORTRWBYBJVGVQC-UHFFFAOYSA-N 0.000 claims description 2
- PMBXCGGQNSVESQ-UHFFFAOYSA-N 1-Hexanethiol Chemical compound CCCCCCS PMBXCGGQNSVESQ-UHFFFAOYSA-N 0.000 claims 2
- VTXVGVNLYGSIAR-UHFFFAOYSA-N decane-1-thiol Chemical compound CCCCCCCCCCS VTXVGVNLYGSIAR-UHFFFAOYSA-N 0.000 claims 1
- QJAOYSPHSNGHNC-UHFFFAOYSA-N octadecane-1-thiol Chemical compound CCCCCCCCCCCCCCCCCCS QJAOYSPHSNGHNC-UHFFFAOYSA-N 0.000 claims 1
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 claims 1
- NBZANZVJRKXVBH-GYDPHNCVSA-N alpha-Cryptoxanthin Natural products O[C@H]1CC(C)(C)C(/C=C/C(=C\C=C\C(=C/C=C/C=C(\C=C\C=C(/C=C/[C@H]2C(C)=CCCC2(C)C)\C)/C)\C)/C)=C(C)C1 NBZANZVJRKXVBH-GYDPHNCVSA-N 0.000 abstract 1
- 238000010586 diagram Methods 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
- 229920005862 polyol Polymers 0.000 description 29
- 150000003077 polyols Chemical class 0.000 description 28
- 238000000576 coating method Methods 0.000 description 27
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 21
- 239000003973 paint Substances 0.000 description 20
- 150000002009 diols Chemical class 0.000 description 19
- 239000000126 substance Substances 0.000 description 19
- 239000011248 coating agent Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000003054 catalyst Substances 0.000 description 14
- 238000006116 polymerization reaction Methods 0.000 description 12
- 238000009472 formulation Methods 0.000 description 11
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 239000000839 emulsion Substances 0.000 description 10
- 238000003860 storage Methods 0.000 description 10
- 125000001931 aliphatic group Chemical group 0.000 description 8
- 230000014759 maintenance of location Effects 0.000 description 8
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- 239000011230 binding agent Substances 0.000 description 7
- 238000005227 gel permeation chromatography Methods 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000010998 test method Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- CIWBSHSKHKDKBQ-DUZGATOHSA-N D-isoascorbic acid Chemical compound OC[C@@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-DUZGATOHSA-N 0.000 description 5
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 235000010350 erythorbic acid Nutrition 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 5
- 229940026239 isoascorbic acid Drugs 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000002736 nonionic surfactant Substances 0.000 description 5
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000004067 bulking agent Substances 0.000 description 4
- 238000000113 differential scanning calorimetry Methods 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 4
- 239000011527 polyurethane coating Substances 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000000919 ceramic Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000008199 coating composition Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000000539 dimer Substances 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 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 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 3
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 3
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 3
- 239000012855 volatile organic compound Substances 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- CRQWZKDIVBSAJD-UHFFFAOYSA-N 1-dodecoxydodecane;sodium Chemical compound [Na].CCCCCCCCCCCCOCCCCCCCCCCCC CRQWZKDIVBSAJD-UHFFFAOYSA-N 0.000 description 2
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- IBDVWXAVKPRHCU-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCOC(=O)C(C)=C IBDVWXAVKPRHCU-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- DETXZQGDWUJKMO-UHFFFAOYSA-N 2-hydroxymethanesulfonic acid Chemical compound OCS(O)(=O)=O DETXZQGDWUJKMO-UHFFFAOYSA-N 0.000 description 2
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 2
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 2
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 2
- 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 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- WIVTXBIFTLNVCZ-UHFFFAOYSA-N CC(=C)C(=O)OCCP(=O)=O Chemical compound CC(=C)C(=O)OCCP(=O)=O WIVTXBIFTLNVCZ-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-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
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- 229920002125 Sokalan® Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000003044 adaptive effect Effects 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 229940077388 benzenesulfonate Drugs 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000004815 dispersion polymer Substances 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 239000001023 inorganic pigment Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
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- 238000005829 trimerization reaction Methods 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- YFHICDDUDORKJB-UHFFFAOYSA-N trimethylene carbonate Chemical compound O=C1OCCCO1 YFHICDDUDORKJB-UHFFFAOYSA-N 0.000 description 1
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- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
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- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- C08G18/67—Unsaturated compounds having active hydrogen
-
- 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
- C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
- C09D175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
-
- 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
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/675—Low-molecular-weight compounds
- C08G18/677—Low-molecular-weight compounds containing heteroatoms other than oxygen and the nitrogen of primary or secondary amino groups
- C08G18/6785—Low-molecular-weight compounds containing heteroatoms other than oxygen and the nitrogen of primary or secondary amino groups containing phosphorus
-
- 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
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Abstract
Description
(A)エマルジョンポリマーと、スルフェート界面活性剤、カルボキシル基またはカルボキシレート基を含有しないスルホネート界面活性剤、またはそれらの混合物からなる群から選択される界面活性剤と、を含む水性分散液であって、70,000g/mol以下の重量平均分子量を有するそのエマルジョンポリマーは、そのエマルジョンポリマーの重量に基づく重量基準で、
リン含有酸モノマーおよび/またはその塩の構造単位を0.25%超、ヒドロキシ官能性アルキル(メタ)アクリレートの構造単位、モノエチレン性不飽和非イオン性モノマーの構造単位を15%超、および追加の酸モノマーおよび/またはその塩の構造単位を0~10%含む、水性分散液、ならびに
(B)水分散性ポリイソシアネート、を含む2成分ポリウレタン組成物である。
(i)70,000g/mol以下の重量平均分子量を有するエマルジョンポリマーと、スルフェート界面活性剤、カルボキシル基またはカルボキシレート基を含有しないスルホネート界面活性剤、またはそれらの混合物からなる群から選択される界面活性剤と、を含む水性分散液を提供することであって、連鎖移動剤の存在下でのエマルジョン重合によって調製されたエマルジョンポリマーは、エマルジョンポリマーの重量に基づく重量基準で、
リン含有酸モノマーおよび/またはその塩の構造単位を0.25%超、ヒドロキシ官能性アルキル(メタ)アクリレートの構造単位、モノエチレン性不飽和非イオン性モノマーの構造単位を15%超、および追加の酸モノマーおよび/またはその塩の構造単位を0~10%含む、水性分散液を提供することと、
(ii)ステップ(i)からの水性分散液を、水分散性ポリイソシアネートと混合することと、を含む。
ここで、点線は、構造単位のポリマー骨格への結合点を表す。
OAは、エトキシ、プロポキシ、またはブトキシ基、あるいはそれらの組み合わせを表し、好ましくはエトキシ基を表し、
X+およびM+は、各々独立して、アンモニウムイオン、またはアルカリ金属イオン、例えば、ナトリウムイオンおよびカリウムイオン、好ましくはナトリウムイオンであり、
mは、0~60の範囲であり、
nは、0、または1である。
DISPERBYK-190(BYK 190)分散剤は、BYK Additives & Instrumentsから入手可能である。
水性分散液中のポリマー粒子の粒径は、光子相関分光法(試料粒子の光散乱)の技術を用いるBrookhaven BI-90 Plus Particle Size Analyzerを使用して測定した。この方法では、試験される2滴の水性分散液を、20mLの0.01M塩化ナトリウム(NaCl)溶液で希釈し、さらに、得られた混合物を試料キュベットにおいて希釈して、所望の計数率(K)を達成した(例えば、Kは、10~300nmの範囲の直径に関して250~500カウント/秒の範囲である)。次いで、水性ポリマー分散液の粒径を、測定し、強度に基づくZ平均直径として報告した。
TgはDSCで測定した。5~10ミリグラム(mg)の試料を、窒素雰囲気下でオートサンプラーを取り付けたTA Instrument DSC Q2000上の密閉アルミニウムパンにおいて分析した。DSCによるTg測定は、-40~180℃、10℃/分(第1のサイクル、次いで5分間保持して試料の熱履歴を消去する)、180~-40℃、10℃/分(第2のサイクル)、および-40~180℃、10℃/分(第3のサイクル)を含む3つのサイクルを用いた。Tgは、熱流対温度遷移における中点をTg値とすることによって、第3のサイクルから取得した。
GPC分析は、一般的に、Agilent1200により実行した。試料を2mg/mLの濃度のテトラヒドロフラン(THF)/ギ酸(FA)(5%)に溶解し、次いでGPC分析の前に0.45μmのポリテトラフルオロエチレン(PTFE)フィルターで濾過した。GPC分析は、次の条件を使用して実行された。
カラム:1つのPLgel GUARDカラム(10μm、50ミリメートル(mm)×7.5mm)、2つの混合Bカラム(7.8mm×300mm)直列、カラム温度:40℃;移動相:THF/FA(5%);流量:1.0mL/分;注入体積:100μL;検出器:Agilent屈折率検出器、40℃;および検量線:三次多項式適合度(polynom 3 fitness)を用いる2329000~580g/molの範囲の分子量を有するPLポリスチレンI狭標準。
光沢測定は、ASTM D523(1999)に従って、BYK GardenerマイクロTRI光沢計(BYK-Gardner USA,Columbia,Md.)を使用して所定の角度(60°)で行った。
メチルエチルケトン(MEK)の二重耐摩擦性を使用して、コーティングフィルムの耐薬品性を試験した。それは、ASTM D5402(1999)に従って実施した。2成分ポリウレタン組成物は、150μmの湿潤厚さで、アルミニウムパネル(Q-パネルA-46)上に引き降ろした。室温で20分間乾燥させた後、パネルをさらに60℃で40分間乾燥させ、続いて室温で7日間さらに乾燥させた。得られたコーティングされたパネルは、MEK二重耐摩擦性試験に使用した。Atlasクロックメーターを使用して二重摩擦を実行し、チーズクロスを使用して十分なMEK溶液を保持した。各コーティングフィルムに関して800回の二重摩擦を実施し、コーティングフィルムの最初の突破が発生するのにかかった二重摩擦の数を記録した。各コーティングフィルムについて2回の測定を行った。
鉛筆硬度試験は、鋼基材(Q-パネルR-46)上でASTM D3363(2011)に従って行った。2成分ポリウレタン組成物は、150μmの湿潤厚さで、アルミニウムパネル(Q-パネルA-46)上に引き降ろした。室温で20分間乾燥させた後、パネルをさらに60℃で40分間乾燥させ、続いて室温で7日間さらに乾燥させ、そのコーティングされたパネルを、鉛筆硬度試験に使用した。鉛筆がフィルムに切り込みを入れたり、削ったりしなかったときの鉛筆の芯の硬度を記録した。H以上の硬度が許容可能である。
モノマーエマルジョンの安定性は、モノマーエマルジョンを室温で撹拌せずに30分間放置することによって得られた液体の状態を視覚的に観察することによって評価した。層が分離していない場合は、安定したモノマーエマルジョンを示唆しており、そうでない場合、すなわち、層が分離している場合は、安定性が低いモノマーエマルジョンを示唆している。
安定なモノマーエマルジョンは、318グラム(g)の脱イオン(DI)水、23gのDISPONIL Fes 993界面活性剤(30%)、173gのMMA、306gのST、204gのEHA、304gのHEMA、16gのMAA、16gのPEM、および21gのn-DDMを混合することによって調製した。
表1に示したモノマー組成物に基づいて、上記の実施例1の水性分散液を調製するための上記と同じ手順に従って、実施例2~5の水性分散液をそれぞれ調製した。各水性ポリマー分散液を調製するために使用したモノマーエマルジョンは、良好な安定性を示した。
表1に示したように、モノマー組成物および界面活性剤の種類に基づいて、上記の実施例1の水性分散液を調製するために、上記と同じ手順に従って、これらの水性分散液をそれぞれ調製した。比較例AおよびBの水性ポリマー分散液を調製するとき、固体重量で同じ量の、それぞれRS-710(25%活性)およびA-102(30%活性)を使用して、すべてのステップにおいて、Fes 993(30%活性)界面活性剤を置き換えた。得られた水性分散液の特性を表2に示す。これらのポリマー分散液は、以下で調製された塗料配合物のバインダーとして使用した。
塗料配合物(すなわち、コーティング組成物)および比較(Comp)塗料配合物を、それぞれ表3および表4に示した配合物に基づいて調製した。各塗料配合物中のNCO基対OH基のモル比は1.2:1であった。粉砕段階における配合成分を、高速カウルズ分散機を使用して、毎分1,500回転(rpm)で30分間混合した。次いで、希釈段階(letdown stage)における配合成分を従来の実験室ミキサーを使用して添加して、パートAを得た。各塗料配合物のパートAを一晩置き、次いで高速カウルズ分散機を使用してパートBをパートAに加え、600rpmで10分間塗料配合物を形成した。得られた塗料配合物を、上記の試験法に従って特性について測定し、結果を表5に示す。
Claims (15)
- 2成分ポリウレタン組成物であって、
(A)エマルジョンポリマーと、スルフェート界面活性剤、カルボキシル基またはカルボキシレート基を含有しないスルホネート界面活性剤、またはそれらの混合物からなる群から選択される界面活性剤と、を含む水性分散液であって、70,000g/mol以下の重量平均分子量を有する前記エマルジョンポリマーは、前記エマルジョンポリマーの重量に基づく重量基準で、
リン含有酸モノマーおよび/またはその塩の構造単位を0.25%超、ヒドロキシ官能性アルキル(メタ)アクリレートの構造単位、モノエチレン性不飽和非イオン性モノマーの構造単位を15%超、および追加の酸モノマーおよび/またはその塩の構造単位を0~10%含む、水性分散液、ならびに
(B)水分散性ポリイソシアネート、を含む2成分ポリウレタン組成物。 - 式(I)において、mが、4~60の範囲にあり、nが、1である、請求項2に記載のポリウレタン組成物。
- 前記エマルジョンポリマーが、10,000~50,000g/molの平均重量分子量を有する、請求項1~3のいずれか一項に記載のポリウレタン組成物。
- 前記エマルジョンポリマーが、前記エマルジョンポリマーの重量に基づく重量基準で、ヒドロキシ官能性アルキル(メタ)アクリレートの構造単位を16%~40%含む、請求項1~4のいずれか一項に記載のポリウレタン組成物。
- 前記リン含有酸モノマーおよびその塩が、ホスホエチル(メタ)アクリレート、ホスホプロピル(メタ)アクリレート、ホスホブチル(メタ)アクリレート、アリルエーテルホスフェート、それらの塩、またはそれらの混合物からなる群から選択される、請求項1~5のいずれか一項に記載のポリウレタン組成物。
- 前記ヒドロキシ官能性アルキル(メタ)アクリレートが、2-ヒドロキシエチルアクリレート、2-ヒドロキシエチルメタクリレート、2-ヒドロキシプロピルアクリレート、2-ヒドロキシプロピルメタクリレート、またはそれらの混合物からなる群から選択される、請求項1~6のいずれか一項に記載のポリウレタン組成物。
- 前記エマルジョンポリマーが、0~100℃の測定されたガラス転移温度を有する、請求項1~7のいずれか一項に記載のポリウレタン組成物。
- 前記水性分散液が、前記エマルジョンポリマーの重量に基づく重量基準で、0.1%~10%の界面活性剤を含む、請求項1~8のいずれか一項に記載のポリウレタン組成物。
- 前記ポリイソシアネート中のイソシアネート基当量の総数の、前記水性分散液中のヒドロキシル基当量の総数に対する当量比が、3.0:1.0~0.8:1.0の範囲である、請求項1~9のいずれか一項に記載のポリウレタン組成物。
- 前記エマルジョンポリマーが、50~100nmの粒径を有する、請求項1~10のいずれか一項に記載のポリウレタン組成物。
- 前記エマルジョンポリマーが、前記エマルジョンポリマーの重量に基づく重量基準で、
前記リン含有酸モノマーおよび/またはその塩の構造単位を1%~3%と、
前記ヒドロキシ官能性アルキル(メタ)アクリレートの構造単位を20%~35%と、
スチレン、メチルメタクリレート、シクロヘキシルメタクリレート、ブチルアクリレート、2-エチルヘキシルアクリレート、またはそれらの混合物から選択される前記モノエチレン性不飽和非イオン性モノマーの構造単位を55%~75%と、
前記追加の酸モノマーおよび/またはその塩の構造単位を0~5%と、を含む、請求項1~11のいずれか一項に記載のポリウレタン組成物。 - 顔料をさらに含む、請求項1~12のいずれか一項に記載のポリウレタン組成物。
- 2成分ポリウレタン組成物を調製するプロセスであって、
(i)70,000g/mol以下の重量平均分子量を有するエマルジョンポリマーと、スルフェート界面活性剤、カルボキシル基またはカルボキシレート基を含有しないスルホネート界面活性剤、またはそれらの混合物からなる群から選択される界面活性剤と、を含む水性分散液を提供することであって、連鎖移動剤の存在下でのエマルジョン重合によって調製された前記エマルジョンポリマーは、前記エマルジョンポリマーの重量に基づく重量基準で、
リン含有酸モノマーおよび/またはその塩の構造単位を0.25%超、ヒドロキシ官能性アルキル(メタ)アクリレートの構造単位、モノエチレン性不飽和非イオン性モノマーの構造単位を15%超、および追加の酸モノマーおよび/またはその塩の構造単位を0~10%含む、水性分散液を提供することと、
(ii)ステップ(i)からの前記水性分散液を、水分散性ポリイソシアネートと混合することと、を含む、プロセス。 - 前記連鎖移動剤が、n-ドデシルメルカプタン、セチルメルカプタン、オクタデカンチオール、オクチルメルカプタン、ヘキサンチオール、デカンチオール、またはそれらの混合物である、請求項14に記載のプロセス。
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JP3811406B2 (ja) | 2001-08-02 | 2006-08-23 | デュプロ精工株式会社 | 孔版印刷の製版方法および製版装置ならびに孔版印刷機 |
JP3811046B2 (ja) | 2001-10-15 | 2006-08-16 | 株式会社日本触媒 | 水性硬化性樹脂組成物 |
DE10237576A1 (de) | 2002-08-16 | 2004-02-26 | Bayer Ag | Wässrige Bindemittel-Dispersionen als Überzugsmittel |
EP1599526B1 (en) | 2003-02-28 | 2012-06-13 | Dow Global Technologies LLC | Preparation of isocyanurate group containing polyisocyanate mixtures |
CN1557892A (zh) * | 2004-01-18 | 2004-12-29 | 西北师范大学 | 一种水性双组分聚氨酯涂料及其制备方法 |
CN100363421C (zh) * | 2005-02-05 | 2008-01-23 | 广州慧谷化学有限公司 | 一种热固性丙烯酸乳液及其制备方法以及含有该乳液的涂料 |
EP2021393A1 (en) * | 2006-05-16 | 2009-02-11 | Dow Global Technologies Inc. | Aqueous non-ionic hydrophilic polyurethane dispersions, and a continuous process of making the same |
US20090298989A1 (en) * | 2008-05-28 | 2009-12-03 | Funston Sr Randall A | 2K Waterborne Polyurethane Coating System and Methods Thereof |
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CN107057545B (zh) * | 2016-12-28 | 2019-08-02 | 中国海洋石油总公司 | 水性双组分丙烯酸聚氨酯中涂及其制备方法 |
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