CN103773210A - Bi-component waterborne polyurethane coating composition - Google Patents
Bi-component waterborne polyurethane coating composition Download PDFInfo
- Publication number
- CN103773210A CN103773210A CN201210452211.XA CN201210452211A CN103773210A CN 103773210 A CN103773210 A CN 103773210A CN 201210452211 A CN201210452211 A CN 201210452211A CN 103773210 A CN103773210 A CN 103773210A
- Authority
- CN
- China
- Prior art keywords
- waterborne
- coating composition
- component
- polyurethane coating
- component polyurethane
- 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 72
- 239000011527 polyurethane coating Substances 0.000 title claims abstract description 65
- 229920000642 polymer Polymers 0.000 claims abstract description 66
- 239000006185 dispersion Substances 0.000 claims abstract description 50
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical class CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims abstract description 40
- 239000007787 solid Substances 0.000 claims abstract description 16
- 239000000839 emulsion Substances 0.000 claims abstract description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 11
- 238000002360 preparation method Methods 0.000 claims description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 45
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 38
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 30
- 239000003112 inhibitor Substances 0.000 claims description 19
- 230000003647 oxidation Effects 0.000 claims description 19
- 238000007254 oxidation reaction Methods 0.000 claims description 19
- 230000000051 modifying effect Effects 0.000 claims description 18
- 239000000758 substrate Substances 0.000 claims description 16
- 238000012986 modification Methods 0.000 claims description 12
- 230000004048 modification Effects 0.000 claims description 12
- 229920005906 polyester polyol Polymers 0.000 claims description 11
- 239000003963 antioxidant agent Substances 0.000 claims description 6
- 230000003078 antioxidant effect Effects 0.000 claims description 6
- 150000002989 phenols Chemical class 0.000 claims description 6
- 229920003009 polyurethane dispersion Polymers 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 5
- 229920000728 polyester Polymers 0.000 claims description 5
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 claims description 4
- 238000005259 measurement Methods 0.000 claims description 2
- 150000008301 phosphite esters Chemical class 0.000 claims description 2
- 238000004383 yellowing Methods 0.000 abstract description 34
- 229920005862 polyol Polymers 0.000 abstract description 28
- 239000011248 coating agent Substances 0.000 abstract description 27
- 238000000576 coating method Methods 0.000 abstract description 27
- 150000003077 polyols Chemical class 0.000 abstract description 27
- 239000008199 coating composition Substances 0.000 abstract description 19
- 238000012360 testing method Methods 0.000 description 37
- 238000003756 stirring Methods 0.000 description 29
- 238000000034 method Methods 0.000 description 26
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 24
- 239000003795 chemical substances by application Substances 0.000 description 24
- 239000000049 pigment Substances 0.000 description 24
- 230000000052 comparative effect Effects 0.000 description 16
- -1 polytetramethylene Polymers 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 238000001914 filtration Methods 0.000 description 13
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 11
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical group O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 11
- 238000003801 milling Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 239000004576 sand Substances 0.000 description 11
- 239000012752 auxiliary agent Substances 0.000 description 9
- 239000008367 deionised water Substances 0.000 description 9
- 229910021641 deionized water Inorganic materials 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- 238000002203 pretreatment Methods 0.000 description 9
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 238000010907 mechanical stirring Methods 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 238000010790 dilution Methods 0.000 description 7
- 239000012895 dilution Substances 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 239000003973 paint Substances 0.000 description 7
- 229920002635 polyurethane Polymers 0.000 description 7
- 239000004814 polyurethane Substances 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 229920000570 polyether Polymers 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- 239000005056 polyisocyanate Substances 0.000 description 5
- 229920001228 polyisocyanate Polymers 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 239000006184 cosolvent Substances 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000004408 titanium dioxide Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 229930182556 Polyacetal Natural products 0.000 description 3
- 229920002396 Polyurea Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- 229920006324 polyoxymethylene Polymers 0.000 description 3
- 229920006295 polythiol Polymers 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- DAFHKNAQFPVRKR-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylpropanoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)C DAFHKNAQFPVRKR-UHFFFAOYSA-N 0.000 description 2
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 2
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-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
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-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
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 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
- 239000002253 acid Substances 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- 125000000129 anionic 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
- 238000009835 boiling Methods 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 239000013530 defoamer Substances 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- 229940051250 hexylene glycol Drugs 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- 239000010445 mica Substances 0.000 description 2
- 229910052618 mica group Inorganic materials 0.000 description 2
- 238000002715 modification method Methods 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- MBAUOPQYSQVYJV-UHFFFAOYSA-N octyl 3-[4-hydroxy-3,5-di(propan-2-yl)phenyl]propanoate Chemical compound OC1=C(C=C(C=C1C(C)C)CCC(=O)OCCCCCCCC)C(C)C MBAUOPQYSQVYJV-UHFFFAOYSA-N 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 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
- 239000000843 powder Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical group CCC1CO1 RBACIKXCRWGCBB-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
- CMQUQOHNANGDOR-UHFFFAOYSA-N 2,3-dibromo-4-(2,4-dibromo-5-hydroxyphenyl)phenol Chemical compound BrC1=C(Br)C(O)=CC=C1C1=CC(O)=C(Br)C=C1Br CMQUQOHNANGDOR-UHFFFAOYSA-N 0.000 description 1
- PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical group CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 description 1
- FANGQVKSFHFPBY-UHFFFAOYSA-N 2-(3,5-ditert-butyl-4-hydroxyphenyl)propanoic acid Chemical compound OC(=O)C(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FANGQVKSFHFPBY-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- AIDLAEPHWROGFI-UHFFFAOYSA-N 2-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=C(C(O)=O)C=CC=C1C(O)=O AIDLAEPHWROGFI-UHFFFAOYSA-N 0.000 description 1
- CCTFMNIEFHGTDU-UHFFFAOYSA-N 3-methoxypropyl acetate Chemical compound COCCCOC(C)=O CCTFMNIEFHGTDU-UHFFFAOYSA-N 0.000 description 1
- PNWSHHILERSSLF-UHFFFAOYSA-N 4-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=CC=C(C(O)=O)C=C1C(O)=O PNWSHHILERSSLF-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
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- 238000006957 Michael reaction Methods 0.000 description 1
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 1
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- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
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- 229910000831 Steel Inorganic materials 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
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- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- PZZYQPZGQPZBDN-UHFFFAOYSA-N aluminium silicate Chemical compound O=[Al]O[Si](=O)O[Al]=O PZZYQPZGQPZBDN-UHFFFAOYSA-N 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001409 amidines Chemical group 0.000 description 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 229940043232 butyl acetate Drugs 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000003618 dip coating Methods 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
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001033 ether group Chemical group 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
- 239000004744 fabric Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- JBFHTYHTHYHCDJ-UHFFFAOYSA-N gamma-caprolactone Chemical compound CCC1CCC(=O)O1 JBFHTYHTHYHCDJ-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical class CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000003010 ionic group Chemical group 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000001034 iron oxide pigment Substances 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 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
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 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
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940100573 methylpropanediol Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 239000000123 paper 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
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920003226 polyurethane urea Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical compound C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000000007 visual effect Effects 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
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/625—Polymers of alpha-beta ethylenically unsaturated carboxylic acids; hydrolyzed polymers of esters of these acids
- C08G18/6254—Polymers of alpha-beta ethylenically unsaturated carboxylic acids and of esters of these acids containing hydroxy groups
-
- 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
- C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
- C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
- C08G18/0828—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing sulfonate groups or groups forming them
-
- 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
- C08G18/28—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
-
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
- C08G18/6225—Polymers of esters of acrylic or methacrylic acid
- C08G18/6229—Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols
-
- 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
- C08G18/703—Isocyanates or isothiocyanates transformed in a latent form by physical means
- C08G18/705—Dispersions of isocyanates or isothiocyanates in a liquid medium
- C08G18/706—Dispersions of isocyanates or isothiocyanates in a liquid medium the liquid medium being water
-
- 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
- C08G18/775—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur sulfur
-
- 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
- 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
- C09D175/06—Polyurethanes from polyesters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Dispersion Chemistry (AREA)
- Manufacturing & Machinery (AREA)
- Paints Or Removers (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention relates to a bi-component waterborne polyurethane coating composition. The bi-component waterborne polyurethane coating composition comprises a component (a) and a component (b), wherein the component (a) comprises one or more polyol waterborne dispersions or waterborne emulsion, the content of hydroxy in the polyol is 0.5-5.5 wt.% based on the situation that the weight of the polyol is weighted by 100 wt.%, and the solid content of the polyol waterborne dispersion or the waterborne emulsion is 10-70 wt.% based on the situation that the total weight of the polyol waterborne dispersion or the waterborne emulsion is weighted by 100 wt.%; the component (b) comprises one or more hydrophilic modified isophorone diisocyanate polymers or prepolymers; due to the contents of the component (a) and the component (b), the equivalence ratio of an NCO group to the hydroxy in the bi-component waterborne polyurethane coating composition is 0.2:1 to 5:1. The bi-component waterborne polyurethane coating composition has high temperature yellowing resistance, and the chromatism value of a coating film prepared from the coating composition is less than 3.0 after the coating film is baked at the temperature of 150 DEG C for 1 day.
Description
Technical field
The present invention relates to a kind of waterborne two-component polyurethane coating composition, relate to particularly a kind of aqueous polyurethane coating composition that comprises isophorone diisocyanate polymer or performed polymer.
Background technology
Bicomponent polyurethane coating is generally made up of the curing agent component that contains isocyanate functional group and the paint vehicle component that contains hydroxyl or amidine functional group.Bicomponent polyurethane coating can be divided into solvent borne polyurethane coating and aqueous polyurethane coating conventionally.Aqueous polyurethane coating, particularly waterborne two-component polyurethane coating, owing to not only having retained the premium properties of solvent borne polyurethane coating, also have good environment friendly simultaneously, has broad application prospects.
Waterborne two-component polyurethane coating, under hot environment, because its film, under long-term (>=the 24h) of high temperature (>=150 ℃) baking, Yellowing easily occurs, has limited its application in hot environment.More existing researchs in recent years attempt to improve the capable of resisting high-temperature yellowing performance of polyurethane coating.CN101397475 has disclosed a kind of preparation method of polyurethane high temperature resistant long acting anti-corrosive paint, but it belongs to solvent borne polyurethane system, and does not relate to capable of resisting high-temperature yellowing performance in the performance of its assessment; CN1629234 has disclosed a kind of high-gloss and high temperature resistant silicon-acrylic polyurethane paint and preparation method thereof, but selected resin is organic-silicon-modified acrylic resin, and solidifying agent is HDI, and does not relate to the concrete measure of capable of resisting high-temperature yellowing.For another example CN101481578A has disclosed capacitor coating of a kind of deep drawing resistant performance and high temperature yellowing resistance and preparation method thereof, but it belongs to solvent borne polyurethane system, and select the polymeric polyisocyanate of sealing as solidifying agent, belong to the scope of baking vanish, at room temperature film-forming.
Therefore not yet there is up to now the report of the waterborne two-component polyurethane coating to thering is capable of resisting high-temperature yellowing performance.
Summary of the invention
One aspect of the present invention provides a kind of waterborne two-component polyurethane coating with capable of resisting high-temperature yellowing, and described waterborne two-component polyurethane coating composition comprises:
(a) one or more polyvalent alcohol aqueous dispersion or water-based emulsions, the hydroxy radical content of wherein said polyvalent alcohol is 0.5-5.5wt.%, weight based on described polyvalent alcohol is by 100wt.%, the solid content of described polyvalent alcohol aqueous dispersion or water-based emulsion is 10-70wt.%, and the gross weight based on described polyvalent alcohol aqueous dispersion or water-based emulsion is by 100wt.%;
(b) isophorone diisocyanate polymer or the performed polymer of one or more hydrophilic modifyings;
It is 0.2: 1 to 5: 1 that wherein said component (a) and content (b) make the equivalence ratio of NCO group and hydroxyl in described waterborne two-component polyurethane coating composition.In a preferred embodiment, to make the equivalence ratio of NCO group and hydroxyl in described waterborne two-component polyurethane coating composition be 1.2: 1 to 1.5: 1 for described component (a) and content (b).
In one embodiment of the invention, the isophorone diisocyanate polymer of described hydrophilic modifying or the NCO content of performed polymer are 10-14wt.%, and the isophorone diisocyanate polymer based on described hydrophilic modifying or the weight of performed polymer are by 100wt.%.
In another embodiment, the isophorone diisocyanate polymer of described hydrophilic modifying or performed polymer are selected from polyether-modified isophorone diisocyanate performed polymer, isophorone diisocyanate polymer and the combination thereof of sulfamate modification.
In another embodiment of the present invention, described polyvalent alcohol is selected from acrylate polyvalent alcohol, polyester polyol and the combination thereof of polyester modification.
Go back in an embodiment in the present invention, described composition also comprises: (c) oxidation inhibitor.Preferably, described oxidation inhibitor is selected from Hinered phenols antioxidant, organophosphite oxidation inhibitor or its combination.Preferably, the content of described oxidation inhibitor is 0.01-5wt.%, and the total weight of solids based on described waterborne two-component polyurethane coating composition is by 100wt.%.
Go back in an embodiment in the present invention, described waterborne two-component polyurethane coating composition also comprises: (d) aqueous polyurethane dispersion.
The present invention relates to a kind of coated products on the other hand, and described coated products comprises substrate and be coated in described suprabasil film, and described film is prepared according to above-mentioned waterborne two-component polyurethane coating composition.Preferably, the value of chromatism that film toasts after 1 day at 150 ℃ is less than 3.0, and described value of chromatism is according to GB11186.2 and GB11186.3 Measurement and Computation respectively.
Embodiment
I.
waterborne two-component polyurethane coating composition
In one embodiment of the invention, a kind of waterborne two-component polyurethane coating composition is provided, described waterborne two-component polyurethane coating composition comprises:
(a) one or more polyvalent alcohol aqueous dispersion or water-based emulsions, the hydroxy radical content of wherein said polyvalent alcohol is 0.5-5.5wt.%, weight based on described polyvalent alcohol is by 100wt.%, the solid content of described polyvalent alcohol aqueous dispersion or water-based emulsion is 10-70wt.%, and the gross weight based on described polyvalent alcohol aqueous dispersion or water-based emulsion is by 100wt.%;
(b) isophorone diisocyanate polymer or the performed polymer of one or more hydrophilic modifyings;
It is 0.2: 1 to 5: 1 that wherein said component (a) and content (b) make the equivalence ratio of NCO group and hydroxyl in described waterborne two-component polyurethane coating composition.In a preferred embodiment, to make the equivalence ratio of NCO group and hydroxyl in described waterborne two-component polyurethane coating composition be 1.2: 1 to 1.5: 1 for described component (a) and content (b).
When for time of the present invention, " polyurethane coating " has meaning well-known to those skilled in the art.Waterborne two-component polyurethane coating above-mentioned except comprising (a) and (b) component, can also comprise the components such as the conventional color stuffing in this area, solvent, catalyzer and auxiliary agent.
(a) polyvalent alcohol
Being suitable for polyvalent alcohol of the present invention can be to be usually used in polyvalent alcohol in aqueous polyurethane coating field, and it comprises molecular weight (M
n) for 400-6000, be preferably the polyvalent alcohol of 400-3000.Described polyvalent alcohol uses with the form of aqueous dispersion or water-based emulsion, preferably uses with the form of aqueous dispersion.The aqueous dispersion of polyol component or water-based emulsion can be by the method preparations of letex polymerization in water, the method is known to those skilled in the art, for example, at B.Vollmert, " GrundrissderMakromolekularen Chemie ", the first roll, below 181 pages, Vollmert Verlag1988, Karlsruhe, or H.G.Elias, " Makromolek ü le ", volume Two, below 93 pages, H ü thig & Wepf Verlag Basel, Heidelberg, the explanation in New York1992.
The example of described polyvalent alcohol includes, but are not limited to:
1) polyester polyol, described polyester polyol is made by di-carboxylic acid or dicarboxylic acid anhydride and polyol reaction.Described di-carboxylic acid, preferably but be not limited to the aliphatic carboxylic acid containing 2-12 carbon atom, the described aliphatic carboxylic acid containing 2-12 carbon atom, preferred but be not limited to succinic acid, propanedioic acid, pentanedioic acid, hexanodioic acid, suberic acid, nonane diacid, sebacic acid, dodecyl carboxylic acid, maleic acid, FUMARIC ACID TECH GRADE, phthalic acid, m-phthalic acid, terephthalic acid or their mixture.Described dicarboxylic acid anhydride, preferably but be not limited to Tetra hydro Phthalic anhydride, tetrachlorophthalic anhydride, maleic anhydride or their mixture.Described polyvalent alcohol, preferably but be not limited to ethylene glycol, glycol ether, 1,2-propylene glycol, 1, ammediol, dipropylene glycol, 1,3-methyl propanediol, BDO, 1,5-PD, 1,6-hexylene glycol, neopentyl glycol, decamethylene-glycol, glycerol, TriMethylolPropane(TMP) or their mixture.Described polyester polyol, also comprises the polyester polyol of being prepared by lactone.The described polyester polyol of being prepared by lactone, preferably but be not limited to 6-caprolactone.
2) polycarbonate polyol, described polycarbonate is to obtain with reacting of dibasic alcohol by carbonic acid derivatives, the example of carbonic acid derivatives includes but not limited to diphenyl carbonate, methylcarbonate or carbonyl chloride.The suitable example of dibasic alcohol includes but not limited to ethylene glycol, 1,2-and 1,3-PD, 1,3-and 1,4-butyleneglycol, 1,6-hexylene glycol, 1,8-ethohexadiol, neopentyl glycol, Isosorbide-5-Nitrae-bis-methylol hexanaphthenes, 2-methyl isophthalic acid, ammediol, 2,2,4-trimethylammonium penta-1,3-glycol, dipropylene glycol, polypropylene glycol, dibutylene glycol, polytetramethylene glycol, dihydroxyphenyl propane, tetrabromo-bisphenol and interior ester modified dibasic alcohol.Dibasic alcohol preferably contains the hexylene glycol of 40-100wt.%, and preferably 1,6-hexylene glycol and/or hexane diol derivatives, particularly preferably they also contain ether or ester group except terminal hydroxy group.Preferably line style of polycarbonate polyol, but it can suitably mix multifunctional component, particularly low molecular weight polyols, and there is the low degree of branching.The examples of compounds that is suitable for this object includes but not limited to glycerol, TriMethylolPropane(TMP), 1,2,6-hexanetriol, 1,2,4-trihydroxybutane, TriMethylolPropane(TMP), tetramethylolmethane, quinite, N.F,USP MANNITOL and Sorbitol Powder, methyl are joined sugar or 1,3,4,6-, bis-dewatering hexitols.
3) polyether glycol, described polyether glycol can be reacted and make in the time that catalyzer exists with initiator by alkene oxide.Described catalyzer, preferably but be not limited to alkaline hydrated oxide, alkaline alkoxide, antimony pentachloride, boron fluoride and close ether or their mixture.Described alkene oxide, preferably but be not limited to tetrahydrofuran (THF), oxyethane, 1,2 epoxy prapane, 1,2-butylene oxide ring, 2,3-butylene oxide ring, Styrene oxide 98min. or their mixture.Described initiator, preferably but be not limited to polyol, described polyol, preferably but be not limited to water, ethylene glycol, 1,2-PD, 1,3-PD, glycol ether, TriMethylolPropane(TMP) or their mixture.The polyether glycol of vinyl polymer modification also can be for the present invention, and this series products can polymerization under polyethers exists make (United States Patent (USP) the 3rd, 383,351,3,304,273,3,523,095 and 3,110, No. 695 by for example vinylbenzene and vinyl cyanide; German Patent the 1st, 152, No. 536).
4) polythioether, for example, react by thiodiglycol self condensation and/or with other glycol, dicarboxylic acid, formaldehyde, aminocarboxylic acid or amino alcohol the condensation product making.This product is ether (polythio-mixed ether), polythioether ester or the polythioether esteramides that poly-sulfo-mixes, and specifically depends on the component of common use.
5) polyacetal, comprises by above-mentioned polyvalent alcohol, particularly glycol ether, triglycol, 4,4 '-dioxy base oxethyl-phenylbenzene dimethylene, 1, the polyacetal that 6-hexylene glycol and formaldehyde obtain.Being applicable to polyacetal of the present invention can also make by the polymerization of ring acetal.
6) polyether ester containing isocyanic ester-reactive group as known in the art.
7) polyesteramide and polymeric amide, comprises or unsaturated carboxylic acid or their acid anhydrides saturated by multivalence and multivalence is saturated or the condenses of basic straight chain prepared by unsaturated amino alcohols, diamines, polyamines or their mixture.
In one embodiment of the invention, polyvalent alcohol is selected from polyester modification acrylate polyvalent alcohol, polyester polyol or its combination, and preferably uses with the form of aqueous dispersion.
The solids content that can be used for polyester modification acrylate polyvalent alcohol aqueous dispersion of the present invention can be 30wt.-60wt.%, can also be 38wt.-45wt.%, and the gross weight based on described dispersion is by 100wt.%; Its hydroxy radical content can be 0.5wt.-5.5wt.%, can also be 3.5wt.%-4.5wt.%, and the solids content based on described dispersion is by 100wt.%.The example that can be used for the acrylate polyvalent alcohol of polyester modification of the present invention includes but not limited to: purchased from Bayhydrol A2227/1 and the Bayhydrol A2058 of Bayer Materials Co., Ltd.
The solids content that can be used for polyester polyol aqueous dispersion of the present invention can be 10wt.-70wt.%, can also be 35wt.-45wt.%, and the gross weight based on described dispersion is by 100wt.%; Its hydroxy radical content can be 0.5wt.-5.5wt.%, can also be 1.5wt.%-4.6wt.%, and the solids content based on described dispersion is by 100wt.%.The example that can be used for polyester polyol of the present invention includes but not limited to: Bayhydrol U XP2766 and Bayhydrol U XP2755.
(b) isophorone diisocyanate polymer or the performed polymer of hydrophilic modifying
When for time of the present invention, " isophorone diisocyanate (IPDI) polymer " refers to nonocclusive IPDI polyisocyanates self-aggregate, and it can be the mixture with the self-aggregate of the isophorone diisocyanate of different polymerization degree.Preferably, IPDI polymer is IPDI tripolymer.
Isophorone diisocyanate performed polymer also can be for the present invention.Isophorone diisocyanate performed polymer refer to isophorone diisocyanate and co-reactant react in advance gained take urethane segment as skeleton, with the polymkeric substance of the intermediate molecular weight of NCO group end capping.Suitable co-reactant comprises polyamines and polyvalent alcohol.The example of suitable polyamines include but not limited to primary amine and secondary amine, and composition thereof, can also use the polyureas of amine end-blocking.The amine that comprises tertiary amine functional group also can be for the present invention, and condition is that this amine also comprises at least two primary aminos and/or secondary amino group.The example of suitable polyvalent alcohol includes but not limited to polyether glycol, polyester polyol, polyurea polylol (for example michael reaction product of amino-functional polyureas and hydroxyl-functional (methyl) acrylate), polycaprolactone polyol, polycarbonate polyol, polyurethane polyol, polyvinyl alcohol, has the unsaturated monomer of branched hydroxy group the addition polymer of (for example containing (methyl) acrylate, vinyl carbinol of hydroxyl-functional and composition thereof).The example that can be used as isophorone diisocyanate performed polymer of the present invention includes but not limited to
401-70.
Can be used for isophorone diisocyanate polymer or performed polymer that isophorone diisocyanate polymer of the present invention or performed polymer are hydrophilic modifying.Those skilled in the art know the hydrophilic modification method of polyisocyanates polymer or performed polymer, for example " hydrophilically modified polyisocyanates (Zhang Faai etc., chemistry circular,, the 67th volume, w002 in 2004) ".
Isophorone diisocyanate polymer or performed polymer can be by nonionic and/or the preparations of anionic hydrophilic method of modifying.Wherein nonionic hydrophilic modification method can carry out according to EP-A0540985 and the disclosed method of EP-A0959087.Anionic hydrophilic modification can utilize phosphoric acid ester, sulfuric ester or sulfonate ester group to carry out.In this article, preferably use sulfonate groups, particularly preferably use thionamic acid salt groups to carry out modification, these groups are present in polyisocyanates with the form of chemical bond.
In the present invention, isophorone diisocyanate polymer or performed polymer can also mix hydrophilic modifying according to the disclosed method of EP-A0510438, use nonionic polyoxyalkylene group and negatively charged ion or potential ionic group to carry out hydrophilic modifying simultaneously.
In preferred embodiment of the present invention, the IPDI polymer of hydrophilic modifying is selected from the IPDI polymer of sulfamate modification, and the IPDI performed polymer of hydrophilic modifying is selected from polyether-modified IPDI performed polymer.
Described polyether-modified IPDI performed polymer, its solids content preferably but be not limited to 60-100wt.%, particularly preferably 68-72wt.%.Its NCO content preferably but be not limited to 10-20%, particularly preferably 13-14%.Described sulfamate modification IPDI polymer, its solids content preferably but be not limited to 60-100wt.%, particularly preferably 68-72%.Its NCO content preferably but be not limited to 10-20%, particularly preferably 10-12%.
(c) aqueous polyurethane dispersion
When for time of the present invention, belong to " aqueous polyurethane dispersion " and refer to that containing at least one is scattered in urethane in aqueous medium or the composition of polyurethaneurea polymer or multipolymer, wherein such as water of aqueous medium, comprises deionized water.This term also comprises the above-mentioned composition through super-dry.
In one embodiment of the invention, the solids content of described polyurethane aqueous dispersions is 30-70wt.%, is preferably 55-65wt.%, and the gross weight based on polyurethane aqueous dispersions is by 100wt.%.
(d) oxidation inhibitor
In one embodiment of the invention, waterborne two-component polyurethane coating composition also comprises oxidation inhibitor.Applicant is surprised to find that, in the time that described coating comprises oxidation inhibitor, gained coating has better capable of resisting high-temperature yellowing.Oxidation inhibitor can be any conventional oxidation inhibitor in paint field, and preferably, described oxidation inhibitor is selected from Hinered phenols antioxidant, organic phosphites oxidation inhibitor or its combination.Exemplary Hinered phenols antioxidant is the different monooctyl ester of 3,5-di-t-butyl-4-hydroxy phenylpropionic acid, for example Ciba Irganox1135.Exemplary organic phosphites oxidation inhibitor is, for example Ciba IRGAFOS168.
Those skilled in the art can according to predetermined purposes and the actual content that need to determine oxidation inhibitor, for example, be 0.01-5wt.%, and the total weight of solids based on described waterborne two-component polyurethane coating composition is by 100wt.%.
(e) pigment and filler
According to the intended purpose of coating composition, coating composition can be transparent (not comprising pigment), translucent or containing pigment.Therefore coating composition can contain transparent filler and give the pigment of coating composition color and/or effect.The pigment of giving color and/or effect can be selected from organic and mineral dye, tint permanence pigment, fillibility pigment, rheology control pigment, visual effect pigments, conductive pigment, magnetic shielding pigment and high-visibility pigment, metallic pigment or metal-powder, organic and inorganic filler, transparent or opacifying property weighting agent and nanoparticle pigment.The example of giving the inorganic or pigment dyestuff of color includes but not limited to titanium dioxide, micronized titanium dioxide, iron oxide pigment, carbon black, azo pigment, phthalocyanine pigment, quinacridone or pyrrolopyrrole pigment.The example of giving the pigment of effect includes but not limited to the special effect pigments of metallic pigment, coated interference pigment (for example metal oxide coated metallic pigment, for example titanium dioxide-coated or mixed oxide coating aluminium), coated mica (for example titanium dioxide-coated mica) and similar graphite effect.The example of filler includes but not limited to hibbsite, silicon-dioxide, pure aluminium silicate, barium sulfate, calcium carbonate and talcum.
Those skilled in the art can determine according to predetermined purposes and actual needs the consumption of pigment and filler, for example 0-200wt.%, and the gross weight of coating based composition is by 100wt.%.
(f) solvent
Coating composition of the present invention contains the water as liquid diluent, and optionally it can also contain organic cosolvent.The amount of organic cosolvent remains on bottom line.
Water for coating composition of the present invention is preferably deionized water, and its content can be 1-90wt.%, is preferably 30-70wt.%, and the gross weight of coating based composition is by 100wt.%.
The example that may reside in the organic cosolvent in water includes but not limited to glycol ether ester, for example acetic acid ethyl glycol ester, acetic acid butyldiglycol ester, acetic acid methoxy-propyl ester; Ester, for example Texacar PC (4-methyl isophthalic acid, 3-dioxolan-2-one), ethyl acetate, butylacetate, isobutyl acetate, pentyl acetate; Ketone, for example methyl ethyl ketone, methyl propyl ketone, methyl isopropyl Ketone, methyl iso-butyl ketone (MIBK), diisobutyl ketone, Methyl amyl ketone, pimelinketone, isophorone; Aromatic hydrocarbons, for example toluene, dimethylbenzene, Solvesso100 (boiling range is the aromatic hydrocarbons mixture of 155-185 ℃), Solvesso150 (boiling range is the aromatic hydrocarbons mixture of 182-202 ℃) and aliphatic hydrocarbon.Organic cosolvent content can be 0-15wt.%, is preferably 0-5wt.%, and the gross weight of coating based composition is by 100wt.%.
(g) other auxiliary agent
Except said components (c) oxidation inhibitor, coating composition of the present invention can also contain at least one auxiliary agent.This auxiliary agent can be selected from auxiliary agent conventional in this area, for example wetting dispersing agent, base material wetting agent, auxiliary rheological agents, softening agent, flow agent, defoamer and catalyzer.Above-mentioned term all has the implication known to those skilled in the art.
Auxiliary agent can, before coating composition mixes, add in process or afterwards, or can be first after with above-mentioned (a) polyol component or (b) isocyanate component mixes, and gained mixture mixes with other component again.
Those skilled in the art can determine according to predetermined purposes and actual needs kind and the consumption of required auxiliary agent, the consumption of for example wetting dispersing agent can be 0-5wt.%, the consumption of flow agent can be 0-4.5wt.%, the consumption of base material wetting agent can be 0-3wt.%, the consumption of defoamer can be 0-2.2wt.%, the consumption of auxiliary rheological agents can be 0-4wt.%, and the gross weight of the solid of the equal coating based composition of above consumption is by 100wt.%.
Coating composition of the present invention can make as follows: in aqueous medium, for example, mix also each above-mentioned component of dispersion paints composition by high-speed mixer, dissolver or online dissolver (In-Line-Dissolver).
II.
coated products
The present invention also provides a kind of coated products on the other hand, and this coated products comprises substrate and be coated in described suprabasil film, and described film is prepared according to above-mentioned waterborne two-component polyurethane coating composition.Waterborne two-component polyurethane coating composition can be by preparing coated products provided by the invention well known to a person skilled in the art that method is administered in substrate, and these methods include but not limited to that blade coating, excellent painting, spraying, roller coating, brushing, flow coat, cutter are coated with and dip-coating.In one embodiment of the invention, the mode that described coating composition is coated with by blade coating or rod is administered in substrate.In one embodiment of the invention, before being administered in substrate, thereby first each component of coating composition of the present invention being mixed and formed coating composition of the present invention in single container.Also each component of coating composition of the present invention can be fed to respectively in two-pack or plural component spray equipment, thus each component in spray gun, mix, then be sprayed on and in substrate, form film, thereby prepare coated products of the present invention.
Particularly, for individual layer film, it can be 1-500 μ m, is preferably 3-150 μ m.The final coat-thickness of multilayer film can be predefined for 10-2000 μ m, is preferably 50-1000 μ m, and can form with the increment that sprays 10-150 μ m at every turn according to intended purpose.
The coating of coating composition of the present invention can at room temperature or at the temperature higher or lower than room temperature be carried out.Before at high temperature starting to solidify, can exist of short duration sudden strain of a muscle to do the stage, but this stage is not essential.Solidification value can change in 5-200 ℃, can in 20-150 ℃, change especially, most preferably is 100-150 ℃.Set time can be for example 5 minutes to 24 hours.Preferably, coating composition of the present invention is cross-linked 24 hours at the temperature of 20-35 ℃, or is cross-linked 30-60 minute at the temperature of 80-150 ℃.
Curing film can sand milling and/or polishing to obtain the smooth surface of desired thickness.Base material or the goods of coating can cut into desired shape.The film of coated products provided by the invention not only has good mechanical property, there is good capable of resisting high-temperature yellowing simultaneously, the value of chromatism that described film toasts after 1 day at 150 ℃ is less than 3.0, and described value of chromatism is tested according to " GB11186.2 " measuring method of film color " second section (color measuring) ", calculated according to " GB11186.3 " measuring method of film color " Part III (Colorimetry) ".
Waterborne two-component polyurethane coating composition provided by the invention can be applied in any substrate, and the example of described substrate includes but not limited to: timber, plastics, paper, fabric, leather, glass, pottery, gypsum, masonry, concrete, metal (for example iron, steel and aluminium) or film.Described film can be the film that coating composition of the present invention forms afterwards in coating, can be also the film forming after other coating composition coating.
The present invention also relates in one aspect to the purposes of above-mentioned waterborne two-component polyurethane coating composition for the preparation of above-mentioned coated products.
Explain in more detail the present invention by means of Preparation Example below.
Embodiment
Further set forth the present invention below in conjunction with specific embodiment.But it should be understood that these embodiment only do not form limitation of the scope of the invention for the present invention is described.The test method of unreceipted actual conditions in the following example, conventionally according to normal condition, or the condition of advising according to manufacturer is carried out.Except as otherwise noted, all per-cent and umber are by weight.
Mentioned raw material is as shown in the table in this article.
In each embodiment of the present invention, test capable of resisting high-temperature yellowing and other performance of the film being made by coating composition of the present invention, as shown in table 1 below.In table 1, list the selection of each test event and corresponding testing standard or method, corresponding ground and the preparation method of pre-treatment and corresponding test sample, wherein value of chromatism (Δ E) obtains the capable of resisting high-temperature yellowing of coating for weight.
Table 1: the preparation method of the selection of each test event and testing standard or method, ground and pre-treatment, test sample
Component A is the component preparing based on water-based polyol dispersions or emulsion, and B component is the curing agent component based on containing isocyanate groups.
comparative example C1
The comparative example of C1 series has selected hexamethylene diisocyanate (HDI) polymer of 9 kinds of different water-based polyol dispersions and hydrophilic modifying as coating film forming matter.
Take C1-1 as example, the preparation method of formula is described below.C1-2 to C1-9 is with the difference of C1-1: in formulation for coating material, used different types of water-based polyol dispersions instead, but in formula, the preparation method of selected solidifying agent, auxiliary agent and formula is all identical with C1-1.
The preparation of component A
In agitator vessel, drop into 50.00g Bayhydrol A145, under the rotating speed of 1200rpm, stir, slowly drop into successively 0.10g Borchi-Gel PW25,0.20g BYK024,0.70g TEGODispers752W, 13.8g R960,5.45g deionized water, improves mixing speed subsequently to 3000rpm, and keep this rotating speed to disperse 25 minutes, now check fineness, if fineness≤15 μ m stops high speed dispersion; If fineness > is 15 μ m, should proceed high speed dispersion, until fineness≤15 μ m.When after the μ m of fineness≤15, reduce stirring velocity to 1000rpm, slowly drop into 0.6g BYK348, and keep this rotating speed to stir 5 minutes, complete the preparation of component A.
Component A is first with 400 object strainer filterings before use, and in sealed vessel, stores 24 hours.
The preparation of B component
B component is Bayhydur2655, with MPA with solidifying agent: MPA=3: 1 dilution proportion.
Sample preparation and test
According to the formula shown in following table 2, by component A and B component in mass ratio 70.85/17.30 accurately weigh, mechanical stirring makes component A and B component evenly mix for 5 minutes, obtains waterborne two-component polyurethane coating.Carry out sample preparation according to the listed ground of table 1, pre-treatment of substrate method and method for making sample, then measure the value of chromatism of sample, test result is as shown in table 3 below.
The formula of table 2 comparative example C1-1 to C1-9
The capable of resisting high-temperature yellowing test result of table 3 comparative example C1 series
From the test result of table 3, the film that adopts hexamethylene diisocyanate (HDI) polymer of various water-based polyol dispersions and hydrophilic modifying to make as coating film forming matter, after 150 ℃ of high bake 24h, there is obvious Yellowing, its value of chromatism Δ E is all greater than 3, is difficult to realize excellent capable of resisting high-temperature yellowing.Applicant finds simultaneously, different water-based polyol dispersions, and its capable of resisting high-temperature yellowing is also not quite similar, and wherein Bayhydrol A2227/1 and Bayhydrol U XP2766, in comparative example C1 series formula, demonstrate capable of resisting high-temperature yellowing relatively preferably.
comparative example C2 series
The comparative example of C2 series has selected Bayhydrol A2227/1 as water-based polyol dispersions, has selected different types of hexamethylene diisocyanate that can use in aqueous polyurethane coating with bi component (HDI) polymer as coating curing agent.
Take C2-1 as example, the preparation method of formula is described below.C2-2 to C2-6 is with the difference of C2-1: in formulation for coating material, used different types of different types of hexamethylene diisocyanate (HDI) polymer of having used instead instead in formulation for coating material, but in formula, the preparation method of the selected dispersion of water-based polyvalent alcohol, auxiliary agent and formula is all identical with C2-1.
The preparation of component A
In agitator vessel, drop into 50.00Bayhydrol A2227/1, under the rotating speed of 1200rpm, stir, slowly drop into successively 0.10g Borchi-Gel PW25,0.2g BYK024,0.7g TEGODispers752W, 13.8g R960,5.45g deionized water, improves mixing speed subsequently to 3000rpm, and keep this rotating speed to disperse 25 minutes, now check fineness, if fineness≤15 μ m stops high speed dispersion; If fineness > is 15 μ m, should proceed high speed dispersion, until fineness≤15 μ n.When after the μ m of fineness≤15, reduce stirring velocity to 1000rpm, slowly drop into 0.6g BYK348, and keep this rotating speed to stir 5 minutes, complete the preparation of component A.
Component A is first with 400 object strainer filterings before use, and in sealed vessel, stores 24 hours.
The preparation of B component
B component is Bayhydur3100, with MPA with solidifying agent: MPA=3: 1 dilution proportion.
Sample preparation and test
By component A and B component in mass ratio 70.85/22.67 accurately weigh, adopt mechanical stirring to mix, stir 5 minutes, component A and B component are fully mixed.With using after 400 object strainer filterings.
According to the formula shown in following table 4, by component A and B component in mass ratio 70.85/17.30 accurately weigh, mechanical stirring makes component A and B component evenly mix for 5 minutes, obtains waterborne two-component polyurethane coating.Carry out sample preparation according to the listed ground of table 1, pre-treatment of substrate method and method for making sample, then measure the value of chromatism of sample, test result is as shown in table 5 below.
The formula of table 4 comparative example C2-1 to C2-6
Table 5: the capable of resisting high-temperature yellowing test result of comparative example C2 series
From the test result of table 5, adopted preferred water-based polyol dispersions and various can in water, disperse the film that makes as coating film forming matter of hexamethylene diisocyanate (HDI) polymer, after 150 ℃ of high bake 24h, there is obvious Yellowing, its value of chromatism Δ E is all greater than 3, is difficult to realize excellent capable of resisting high-temperature yellowing.
embodiment E 1
The preparation of component A
In agitator vessel, drop into 50.00g Baydrol A2227/1, under the rotating speed of 1200rpm, stir, slowly drop into successively 0.10g Borchi-Gel PW25,0.2g BYK024,0.7g TEGO Dispers752W, 13.8g R960,5.45g deionized water, improves mixing speed subsequently to 3000rpm, and keep this rotating speed to disperse 25 minutes, now check fineness, if fineness≤15 μ m stops high speed dispersion; If fineness > is 15 μ m, should proceed high speed dispersion, until fineness≤15 μ m.When after the μ m of fineness≤15, reduce stirring velocity to 1000rpm, slowly drop into 0.6g BYK348, and keep this rotating speed to stir 5 minutes, complete the preparation of component A.
Component A is first with 400 object strainer filterings before use, and in sealed vessel, stores 24 hours.
The preparation of B component
B component is Bayhydur XP2759, is sulfamate modified isophorone diisocyanate (IPDI) polymer, with MPA with solidifying agent: MPA=3: 1 dilution proportion.
Sample preparation and test
By component A and B component in mass ratio 70.85/51.21 accurately weigh, adopt mechanical stirring to mix, stir 5 minutes, component A and B component are fully mixed.With using after 400 object strainer filterings.
Carry out sample preparation according to the listed ground of table 1, pre-treatment of substrate method and method for making sample, then measure the value of chromatism of sample, test result is as shown in table 6 below.
The capable of resisting high-temperature yellowing test result of table 6 embodiment E 1
In the present embodiment, use sulfamate modified isophorone diisocyanate (IPDI) polymer Bayhydur XP2759 as solidifying agent, its film making is after 150 ℃ of high bake 24h, there is not obvious Yellowing, its value of chromatism △ E is all less than 3, is obviously better than comparative example C1 series and C2 series.
embodiment E 2
The preparation of component A
In agitator vessel, drop into 50.00g Baydrol A2227/1, under the rotating speed of 1200rpm, stir, slowly drop into successively 0.10g Borchi-Gel PW25,0.2g BYK024,0.7g TEGODispers752W, 13.8g R960,5.45g deionized water, improves mixing speed subsequently to 3000rpm, and keep this rotating speed to disperse 25 minutes, now check fineness, if fineness≤15 μ m stops high speed dispersion; If fineness > is 15 μ m, should proceed high speed dispersion, until fineness≤15 μ m.When after the μ m of fineness≤15, reduce stirring velocity to 1000rpm, slowly drop into 0.6g BYK348, and keep this rotating speed to stir 5 minutes, complete the preparation of component A.
Component A is first with 400 object strainer filterings before use, and in sealed vessel, stores 24 hours.
The preparation of B component
B component is Bayhydur XP401-70, is polyether-modified isophorone diisocyanate (IPDI) polymer, uses MPA with solidifying agent/MPA=3/1 dilution.
Sample preparation and test
By component A and B component in mass ratio 70.85/33.52 accurately weigh, adopt mechanical stirring to mix, stir 5 minutes, component A and B component are fully mixed.With using after 400 object strainer filterings.
The project that need to test according to the present embodiment, carries out sample preparation according to the listed ground of table 1, pre-treatment of substrate method and method for making sample.Embodiment E 2 is after high temperature (150 ℃) baking, and the test result of value of chromatism is listed in table 8.
The capable of resisting high-temperature yellowing test result of table 8 embodiment E 2
Therefore, embodiment E 2 is according to the test result of comparative example C1 series, preferably Bayhydrol A2227/1 as water-based polyol dispersions, use separately polyether-modified isophorone diisocyanate (IPDI) polymer Bayhydur XP401-70 as solidifying agent, its film making is after 150 ℃ of high bake 24h, obvious Yellowing does not occur, and its value of chromatism △ E is all less than 3, is obviously better than comparative example C1 series and C2 series.Visible independent use sulfamate modified isophorone diisocyanate (IPDI) polymer Bayhydur XP401-70 has played vital effect as solidifying agent to the capable of resisting high-temperature yellowing that improves waterborne two-component polyurethane coating.
embodiment E 3
The preparation of component A
In agitator vessel, drop into 50.00g Baydrol U XP2766, under the rotating speed of 1200rpm, stir, slowly drop into successively 0.10g Borchi-Gel PW25,0.2g BYK024,0.7g TEGODispers752W, 13.8g R960,5.45g deionized water, improves mixing speed subsequently to 3000rpm, and keep this rotating speed to disperse 25 minutes, now check fineness, if fineness≤15 μ m stops high speed dispersion; If fineness > is 15 μ m, should proceed high speed dispersion, until fineness≤15 μ m.When after the μ m of fineness≤15, reduce stirring velocity to 1000rpm, slowly drop into 0.6g BYK348, and keep this rotating speed to stir 5 minutes, complete the preparation of component A.
Component A is first with 400 object strainer filterings before use, and in sealed vessel, stores 24 hours.
The preparation of B component
B component is Bayhydur XP401-70, is polyether-modified isophorone diisocyanate (IPDI) polymer, uses MPA with solidifying agent/MPA=3/1 dilution.
Sample preparation and test
By component A and B component in mass ratio 70.85/33.7 accurately weigh, adopt mechanical stirring to mix, stir 5 minutes, component A and B component are fully mixed.With using after 400 object strainer filterings.The project that need to test according to the present embodiment, carries out sample preparation according to the listed ground of table 1, pre-treatment of substrate method and method for making sample.Embodiment E 3 is after high temperature (150 ℃) baking, and the test result of value of chromatism is listed in table 9.
Table 9: the capable of resisting high-temperature yellowing test result of embodiment E 3
Therefore, embodiment E 3 is according to the test result of comparative example C1 series, preferably Bayhydrol U XP2766 as water-based polyol dispersions, use separately polyether-modified isophorone diisocyanate (IPDI) polymer Bayhydur XP401-70 as solidifying agent, its film making is after 150 ℃ of high bake 24h, obvious Yellowing does not occur, and its value of chromatism △ E is all less than 3, is obviously better than comparative example C1 series and C2 series.Visible independent use sulfamate modified isophorone diisocyanate (IPDI) polymer Bayhydur XP401-70 has played vital effect as solidifying agent to the capable of resisting high-temperature yellowing that improves waterborne two-component polyurethane coating.
embodiment E 4
The preparation of component A
In agitator vessel, drop into 40.70g Baydrol A2227/1, under the rotating speed of 1200rpm, stir, slowly drop into successively 0.10g Borchi-Gel PW25,0.2g BYK024,0.7g TEGODispers752W, 13.8g R960,5.45g deionized water, improve subsequently mixing speed to 3500rpm, and keep this rotating speed to disperse 25 minutes.Disc type dispersion impeller is replaced by sand milling Special dispersing head, under middle low speed (about 800rpm) stirs, drops into about 60g sand milling pearl, improve mixing speed to 3000rpm, and keep this rotating speed sand milling 60 minutes, now check fineness, if fineness≤15 μ m, stops sand milling; If fineness > is 15 μ m, should continue sand milling, until fineness≤15 μ m.
Use 100-200 object filter screen that above material is filtered, reduce stirring velocity to 1000rpm, slowly drop into 0.6g BYK348,1g Ciba Irganox1135,3.6g Texanol, adds 0.50gBorchi-Gel PW25, and keep this rotating speed to stir 5 minutes, complete the preparation of component A.
Component A is first with 400 object strainer filterings before use, and in sealed vessel, stores 24 hours.
The preparation of B component
B component is Bayhydur XP2759, is sulfamate modified isophorone diisocyanate (IPDI) polymer, uses MPA with solidifying agent/MPA=3/1 dilution.
Sample preparation and test
By component A and B component in mass ratio 66.15/33.30 accurately weigh, adopt mechanical stirring to mix, stir 5 minutes, component A and B component are fully mixed.With using after 400 object strainer filterings.The project that need to test according to the present embodiment, carries out sample preparation according to the listed ground of table 1, pre-treatment of substrate method and method for making sample.Embodiment E 4 is after high temperature (150 ℃) baking, and the test result of value of chromatism is listed in table 10.
The capable of resisting high-temperature yellowing test result of table 10 embodiment E 4
Therefore, embodiment E 4 is according to the test result of comparative example C1 series, preferably Bayhydrol A2227/1 as water-based polyol dispersions, use separately sulfamate modified isophorone diisocyanate (IPDI) polymer Bayhydur XP2759 as solidifying agent, and in formula, add Hinered phenols antioxidant Irganox1135, its film making is after 150 ℃ of high bake 96h, there is not obvious Yellowing, its value of chromatism △ E is less than 3, not only obviously be better than comparative example C1 series and C2 series, and be better than embodiment E 1.The visible Hinered phenols antioxidant that adds in formula has played certain effect to the capable of resisting high-temperature yellowing that improves waterborne two-component polyurethane coating.
embodiment E 5
The preparation of component A
In agitator vessel, drop into 35.06g Baydrol A2227/1,10.52g Impranil LP RSC1537, under the rotating speed of 1200rpm, stir, slowly drop into successively 0.13g Borchi-Gel PW25,0.2gBYK024,0.7g TEGO Dispers752W, 14.45g R960,5.02g deionized water, improves mixing speed subsequently to 3500rpm, and keeps this rotating speed to disperse 25 minutes.Disc type dispersion impeller is replaced by sand milling Special dispersing head, under middle low speed (about 800rpm) stirs, drops into about 60g sand milling pearl, improve mixing speed to 3000rpm, and keep this rotating speed sand milling 60 minutes, now check fineness, if fineness≤15 μ m, stops sand milling; If fineness > is 15 μ m, should continue sand milling, until fineness≤15 μ m.
Use 100-200 object filter screen that above material is filtered, reduce stirring velocity to 1000rpm, slowly drop into 0.6g BYK348,1g Ciba Irganox1135,3.39g Texanol, and keep this rotating speed to stir 5 minutes, complete the preparation of component A.
Component A is first with 400 object strainer filterings before use, and in sealed vessel, stores 24 hours.
The preparation of B component
B component is Bayhydur2759, uses MPA with solidifying agent/MPA=3/1 dilution.
Sample preparation and test
By component A and B component in mass ratio 71.28/28.73 accurately weigh, adopt mechanical stirring to mix, stir 5 minutes, component A and B component are fully mixed.With using after 400 object strainer filterings.The project that need to test according to the present embodiment, carries out sample preparation according to the listed ground of table 1, pre-treatment of substrate method and method for making sample.Take the 100 degree bakings condition of cure of 1 hour to solidify.Embodiment E 5 is listed in table 11 with test event and the result contrast of embodiment E 1.
Table 11 embodiment E 5 contrasts with test event and the result of embodiment E 1
Compared with the formula of embodiment E 1, embodiment E 5 by water-based polyol dispersions Bayhydrol A2227/1 and aqueous polyurethane dispersion Impranil LP RSC1537 with 7/3 ratio (solids content) Mixed Pinyin.From table 11, guaranteeing that under the prerequisite of the not obvious decline of capable of resisting high-temperature yellowing, the snappiness of paint film after high bake obtained significant raising.
In sum, the present invention selects water soluble acrylic acid polyol dispersions and poly-isophorone diisocyanate polymer or the performed polymer film forming matter as coating, for the preparation of the resistant to elevated temperatures aqueous polyurethane coating of two-pack, can greatly improve the capable of resisting high-temperature yellowing of waterborne two-component polyurethane coating.In formula, add oxidation inhibitor, can further improve the capable of resisting high-temperature yellowing of waterborne two-component polyurethane coating.Simultaneously adding of aqueous polyurethane dispersion, effectively improved the snappiness of this coating system, not only xanthochromia is little after high bake to make paint film, and snappiness is good.In addition, this coating has longer usage period, time of drying, good hardness and excellent chemical-resistant faster.
Claims (12)
1. a waterborne two-component polyurethane coating composition, described waterborne two-component polyurethane coating composition comprises:
(a) one or more polyvalent alcohol aqueous dispersion or water-based emulsions, the hydroxy radical content of wherein said polyvalent alcohol is 0.5-5.5wt.%, weight based on described polyvalent alcohol is by 100wt.%, the solid content of described polyvalent alcohol aqueous dispersion or water-based emulsion is 10-70wt.%, and the gross weight based on described polyvalent alcohol aqueous dispersion or water-based emulsion is by 100wt.%;
(b) isophorone diisocyanate polymer or the performed polymer of one or more hydrophilic modifyings;
It is 0.2: 1 to 5: 1 that wherein said component (a) and content (b) make the equivalence ratio of NCO group and hydroxyl in described waterborne two-component polyurethane coating composition.
2. waterborne two-component polyurethane coating composition according to claim 1, the isophorone diisocyanate polymer of wherein said hydrophilic modifying or the NCO content of performed polymer are 10-14wt.%, and the isophorone diisocyanate polymer based on described hydrophilic modifying or the weight of performed polymer are by 100wt.%.
3. waterborne two-component polyurethane coating composition according to claim 1 and 2, the isophorone diisocyanate polymer of wherein said hydrophilic modifying or performed polymer are selected from polyether-modified isophorone diisocyanate performed polymer, isophorone diisocyanate polymer and the combination thereof of sulfamate modification.
4. waterborne two-component polyurethane coating composition according to claim 1, wherein said polyvalent alcohol is selected from acrylate polyvalent alcohol, polyester polyol and the combination thereof of polyester modification.
5. waterborne two-component polyurethane coating composition according to claim 1, wherein said waterborne two-component polyurethane coating composition also comprises: (c) oxidation inhibitor.
6. waterborne two-component polyurethane coating composition according to claim 5, wherein said oxidation inhibitor is selected from Hinered phenols antioxidant, organophosphite oxidation inhibitor or its combination.
7. waterborne two-component polyurethane coating composition according to claim 5, the content of wherein said oxidation inhibitor is 0.01-5wt.%, the total weight of solids based on described waterborne two-component polyurethane coating composition is by 100wt.%.
8. waterborne two-component polyurethane coating composition according to claim 1, it is 1.2: 1 to 1.5: 1 that described component (a) and content (b) make the equivalence ratio of NCO group and hydroxyl in described waterborne two-component polyurethane coating composition.
9. according to the waterborne two-component polyurethane coating composition described in any one in claim 1-8, wherein said waterborne two-component polyurethane coating composition also comprises: (d) aqueous polyurethane dispersion.
10. a coated products, comprises substrate and is coated in described suprabasil film, and described film is according to the waterborne two-component polyurethane coating composition preparation described in any one in claim 1-9.
11. coated productss according to claim 10, the value of chromatism that described film toasts after 1 day at 150 ℃ is less than 3.0, and described value of chromatism is according to GB11186.2 and GB11186.3 Measurement and Computation respectively.
12. according to the waterborne two-component polyurethane coating composition described in any one in claim 1-9 for the preparation of according to the purposes of the coated products described in claim 10 or 11.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210452211.XA CN103773210B (en) | 2012-10-22 | 2012-10-22 | Waterborne two-component polyurethane coating composition |
| PCT/EP2013/071942 WO2014064035A2 (en) | 2012-10-22 | 2013-10-21 | Two-component waterborne polyurethane coating composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN201210452211.XA CN103773210B (en) | 2012-10-22 | 2012-10-22 | Waterborne two-component polyurethane coating composition |
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| CN103773210A true CN103773210A (en) | 2014-05-07 |
| CN103773210B CN103773210B (en) | 2018-10-16 |
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| CN201210452211.XA Expired - Fee Related CN103773210B (en) | 2012-10-22 | 2012-10-22 | Waterborne two-component polyurethane coating composition |
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| CN (1) | CN103773210B (en) |
| WO (1) | WO2014064035A2 (en) |
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| CN103980811A (en) * | 2014-05-19 | 2014-08-13 | 上海维度化工科技有限公司 | Efficient antibacterial waterborne polyurethane floor coating and preparation method thereof |
| CN106280000A (en) * | 2016-08-30 | 2017-01-04 | 贝内克-长顺汽车内饰材料（张家港）有限公司 | A kind of automotive interior material with pearlescent appearance being adapted to vacuum forming |
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| CN110857329A (en) * | 2018-08-24 | 2020-03-03 | 科思创德国股份有限公司 | Polyurethane composition and preparation method and application thereof |
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| CN114133503A (en) * | 2021-12-13 | 2022-03-04 | 西安交通大学 | High-temperature yellowing-resistant nonionic waterborne polyurethane and preparation method thereof |
| CN114292579A (en) * | 2021-12-10 | 2022-04-08 | 浙江亚欣包装材料有限公司 | Coating method of composite film |
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| CN103980811A (en) * | 2014-05-19 | 2014-08-13 | 上海维度化工科技有限公司 | Efficient antibacterial waterborne polyurethane floor coating and preparation method thereof |
| CN103980811B (en) * | 2014-05-19 | 2017-06-16 | 上海维度化工科技有限公司 | A kind of high-efficiency antimicrobial aqueous polyurethane floor coatings and preparation method thereof |
| CN106280000A (en) * | 2016-08-30 | 2017-01-04 | 贝内克-长顺汽车内饰材料（张家港）有限公司 | A kind of automotive interior material with pearlescent appearance being adapted to vacuum forming |
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| CN108250930A (en) * | 2018-01-30 | 2018-07-06 | 河北晨阳工贸集团有限公司 | A kind of agricultural machinery environment protecting water-based paint and preparation method |
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| CN110857329A (en) * | 2018-08-24 | 2020-03-03 | 科思创德国股份有限公司 | Polyurethane composition and preparation method and application thereof |
| CN112839973A (en) * | 2018-08-24 | 2021-05-25 | 科思创知识产权两合公司 | Composition, preparation method and application thereof |
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| CN113289045A (en) * | 2021-05-18 | 2021-08-24 | 长春工业大学 | Preparation of super-hydrophilic medical polyurethane foam dressing |
| CN113289045B (en) * | 2021-05-18 | 2022-07-08 | 长春工业大学 | Preparation of super-hydrophilic medical polyurethane foam dressing |
| CN114292579A (en) * | 2021-12-10 | 2022-04-08 | 浙江亚欣包装材料有限公司 | Coating method of composite film |
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Also Published As
| Publication number | Publication date |
|---|---|
| WO2014064035A2 (en) | 2014-05-01 |
| WO2014064035A3 (en) | 2014-07-03 |
| CN103773210B (en) | 2018-10-16 |
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