CN115210314A - 含氟共聚物组合物 - Google Patents
含氟共聚物组合物 Download PDFInfo
- Publication number
- CN115210314A CN115210314A CN202180016797.2A CN202180016797A CN115210314A CN 115210314 A CN115210314 A CN 115210314A CN 202180016797 A CN202180016797 A CN 202180016797A CN 115210314 A CN115210314 A CN 115210314A
- Authority
- CN
- China
- Prior art keywords
- group
- coating
- coater
- composition
- fluorocopolymer
- 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.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 48
- 229920001577 copolymer Polymers 0.000 title claims abstract description 31
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 23
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 239000011737 fluorine Substances 0.000 title claims abstract description 22
- 238000000576 coating method Methods 0.000 claims abstract description 60
- -1 amine compound Chemical class 0.000 claims abstract description 52
- 239000011248 coating agent Substances 0.000 claims abstract description 48
- 239000002966 varnish Substances 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 19
- 150000003961 organosilicon compounds Chemical class 0.000 claims abstract description 16
- 239000002904 solvent Substances 0.000 claims abstract description 15
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 11
- 238000010528 free radical solution polymerization reaction Methods 0.000 claims abstract description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 229910003849 O-Si Inorganic materials 0.000 claims description 12
- 229910003872 O—Si Inorganic materials 0.000 claims description 12
- 239000003973 paint Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 8
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 8
- 238000005507 spraying Methods 0.000 claims description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 5
- 238000007334 copolymerization reaction Methods 0.000 claims description 5
- 229920001567 vinyl ester resin Polymers 0.000 claims description 5
- 239000008096 xylene Substances 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- 238000010022 rotary screen printing Methods 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 125000001033 ether group Chemical group 0.000 claims description 3
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 230000007774 longterm Effects 0.000 abstract description 7
- 239000003795 chemical substances by application Substances 0.000 description 13
- 238000003860 storage Methods 0.000 description 11
- 239000000178 monomer Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 229920002545 silicone oil Polymers 0.000 description 9
- 239000000243 solution Substances 0.000 description 7
- 239000003381 stabilizer Substances 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 5
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 5
- 229920001807 Urea-formaldehyde Polymers 0.000 description 5
- HMBNQNDUEFFFNZ-UHFFFAOYSA-N 4-ethenoxybutan-1-ol Chemical compound OCCCCOC=C HMBNQNDUEFFFNZ-UHFFFAOYSA-N 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000005056 polyisocyanate Substances 0.000 description 4
- 229920001228 polyisocyanate Polymers 0.000 description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 230000001681 protective effect Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- SKYXLDSRLNRAPS-UHFFFAOYSA-N 1,2,4-trifluoro-5-methoxybenzene Chemical compound COC1=CC(F)=C(F)C=C1F SKYXLDSRLNRAPS-UHFFFAOYSA-N 0.000 description 3
- WULAHPYSGCVQHM-UHFFFAOYSA-N 2-(2-ethenoxyethoxy)ethanol Chemical compound OCCOCCOC=C WULAHPYSGCVQHM-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 3
- 150000007974 melamines Chemical class 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 3
- DQNSRQYYCSXZDF-UHFFFAOYSA-N 1,4-bis(ethenoxymethyl)cyclohexane Chemical compound C=COCC1CCC(COC=C)CC1 DQNSRQYYCSXZDF-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- IIFFFBSAXDNJHX-UHFFFAOYSA-N 2-methyl-n,n-bis(2-methylpropyl)propan-1-amine Chemical compound CC(C)CN(CC(C)C)CC(C)C IIFFFBSAXDNJHX-UHFFFAOYSA-N 0.000 description 2
- GCYHRYNSUGLLMA-UHFFFAOYSA-N 2-prop-2-enoxyethanol Chemical compound OCCOCC=C GCYHRYNSUGLLMA-UHFFFAOYSA-N 0.000 description 2
- PAKCOSURAUIXFG-UHFFFAOYSA-N 3-prop-2-enoxypropane-1,2-diol Chemical compound OCC(O)COCC=C PAKCOSURAUIXFG-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 239000005871 repellent Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 125000005270 trialkylamine group Chemical group 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- AYMDJPGTQFHDSA-UHFFFAOYSA-N 1-(2-ethenoxyethoxy)-2-ethoxyethane Chemical compound CCOCCOCCOC=C AYMDJPGTQFHDSA-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- IBTLFDCPAJLATQ-UHFFFAOYSA-N 1-prop-2-enoxybutane Chemical compound CCCCOCC=C IBTLFDCPAJLATQ-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- XRBWKWGATZNBFW-UHFFFAOYSA-N 2-[2-(2-ethenoxyethoxy)ethoxy]ethanol Chemical compound OCCOCCOCCOC=C XRBWKWGATZNBFW-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
- NJRHMGPRPPEGQL-UHFFFAOYSA-N 2-hydroxybutyl prop-2-enoate Chemical compound CCC(O)COC(=O)C=C NJRHMGPRPPEGQL-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 1
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 1
- ZSSHYFYMKALHQS-UHFFFAOYSA-N 20-ethenoxyicosan-1-ol Chemical compound C(=C)OCCCCCCCCCCCCCCCCCCCCO ZSSHYFYMKALHQS-UHFFFAOYSA-N 0.000 description 1
- TYNRPOFACABVSI-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,6-nonafluorohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC(F)(F)C(F)(F)C(F)(F)C(F)(F)F TYNRPOFACABVSI-UHFFFAOYSA-N 0.000 description 1
- GYUPEJSTJSFVRR-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,6-nonafluorohexyl prop-2-enoate Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)CCOC(=O)C=C GYUPEJSTJSFVRR-UHFFFAOYSA-N 0.000 description 1
- CDXFIRXEAJABAZ-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F CDXFIRXEAJABAZ-UHFFFAOYSA-N 0.000 description 1
- VPKQPPJQTZJZDB-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl prop-2-enoate Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCOC(=O)C=C VPKQPPJQTZJZDB-UHFFFAOYSA-N 0.000 description 1
- ITNADJKYRCCJNX-UHFFFAOYSA-N 3-(2,3-diaminophenyl)sulfonylbenzene-1,2-diamine Chemical compound NC1=CC=CC(S(=O)(=O)C=2C(=C(N)C=CC=2)N)=C1N ITNADJKYRCCJNX-UHFFFAOYSA-N 0.000 description 1
- HBOYQHJSMXAOKY-UHFFFAOYSA-N 3-[methyl-bis(trimethylsilyloxy)silyl]propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](C)(O[Si](C)(C)C)O[Si](C)(C)C HBOYQHJSMXAOKY-UHFFFAOYSA-N 0.000 description 1
- YQFQCQOGRMUSGZ-UHFFFAOYSA-N 3-[methyl-bis(trimethylsilyloxy)silyl]propyl prop-2-enoate Chemical compound C[Si](C)(C)O[Si](C)(O[Si](C)(C)C)CCCOC(=O)C=C YQFQCQOGRMUSGZ-UHFFFAOYSA-N 0.000 description 1
- OJPSFJLSZZTSDF-UHFFFAOYSA-N 3-ethoxyprop-1-ene Chemical compound CCOCC=C OJPSFJLSZZTSDF-UHFFFAOYSA-N 0.000 description 1
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 1
- ZVYGIPWYVVJFRW-UHFFFAOYSA-N 3-methylbutyl prop-2-enoate Chemical compound CC(C)CCOC(=O)C=C ZVYGIPWYVVJFRW-UHFFFAOYSA-N 0.000 description 1
- BESKSSIEODQWBP-UHFFFAOYSA-N 3-tris(trimethylsilyloxy)silylpropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](C)(C)C BESKSSIEODQWBP-UHFFFAOYSA-N 0.000 description 1
- PPBAWVJOPQUAMY-UHFFFAOYSA-N 3-tris(trimethylsilyloxy)silylpropyl prop-2-enoate Chemical compound C[Si](C)(C)O[Si](O[Si](C)(C)C)(O[Si](C)(C)C)CCCOC(=O)C=C PPBAWVJOPQUAMY-UHFFFAOYSA-N 0.000 description 1
- XLLBDKNJKVBVEZ-UHFFFAOYSA-N 4-ethenoxycyclohexan-1-ol Chemical compound OC1CCC(OC=C)CC1 XLLBDKNJKVBVEZ-UHFFFAOYSA-N 0.000 description 1
- YKXAYLPDMSGWEV-UHFFFAOYSA-N 4-hydroxybutyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCO YKXAYLPDMSGWEV-UHFFFAOYSA-N 0.000 description 1
- CJPSFIYLTINNQG-UHFFFAOYSA-N 8-ethenoxy-1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluorooctane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCOC=C CJPSFIYLTINNQG-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- 238000009841 combustion method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
- GTBGXKPAKVYEKJ-UHFFFAOYSA-N decyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C(C)=C GTBGXKPAKVYEKJ-UHFFFAOYSA-N 0.000 description 1
- FWLDHHJLVGRRHD-UHFFFAOYSA-N decyl prop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C=C FWLDHHJLVGRRHD-UHFFFAOYSA-N 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- UBHZUDXTHNMNLD-UHFFFAOYSA-N dimethylsilane Chemical compound C[SiH2]C UBHZUDXTHNMNLD-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229920006334 epoxy coating Polymers 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- WNMORWGTPVWAIB-UHFFFAOYSA-N ethenyl 2-methylpropanoate Chemical compound CC(C)C(=O)OC=C WNMORWGTPVWAIB-UHFFFAOYSA-N 0.000 description 1
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 1
- CMDXMIHZUJPRHG-UHFFFAOYSA-N ethenyl decanoate Chemical compound CCCCCCCCCC(=O)OC=C CMDXMIHZUJPRHG-UHFFFAOYSA-N 0.000 description 1
- GLVVKKSPKXTQRB-UHFFFAOYSA-N ethenyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC=C GLVVKKSPKXTQRB-UHFFFAOYSA-N 0.000 description 1
- UJRIYYLGNDXVTA-UHFFFAOYSA-N ethenyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OC=C UJRIYYLGNDXVTA-UHFFFAOYSA-N 0.000 description 1
- LZWYWAIOTBEZFN-UHFFFAOYSA-N ethenyl hexanoate Chemical compound CCCCCC(=O)OC=C LZWYWAIOTBEZFN-UHFFFAOYSA-N 0.000 description 1
- AFSIMBWBBOJPJG-UHFFFAOYSA-N ethenyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC=C AFSIMBWBBOJPJG-UHFFFAOYSA-N 0.000 description 1
- QBDADGJLZNIRFQ-UHFFFAOYSA-N ethenyl octanoate Chemical compound CCCCCCCC(=O)OC=C QBDADGJLZNIRFQ-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- ZQZUENMXBZVXIZ-UHFFFAOYSA-N ethenyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OC=C ZQZUENMXBZVXIZ-UHFFFAOYSA-N 0.000 description 1
- HBWGDHDXAMFADB-UHFFFAOYSA-N ethenyl(triethyl)silane Chemical compound CC[Si](CC)(CC)C=C HBWGDHDXAMFADB-UHFFFAOYSA-N 0.000 description 1
- GCSJLQSCSDMKTP-UHFFFAOYSA-N ethenyl(trimethyl)silane Chemical compound C[Si](C)(C)C=C GCSJLQSCSDMKTP-UHFFFAOYSA-N 0.000 description 1
- BAVNDESSHRPRRF-UHFFFAOYSA-N ethenyl-diethyl-methylsilane Chemical compound CC[Si](C)(CC)C=C BAVNDESSHRPRRF-UHFFFAOYSA-N 0.000 description 1
- FHHHXDQAWOUGAT-UHFFFAOYSA-N ethenyl-dimethyl-(trifluoromethyl)silane Chemical compound C=C[Si](C)(C)C(F)(F)F FHHHXDQAWOUGAT-UHFFFAOYSA-N 0.000 description 1
- QDEZCOQKJSRQNN-UHFFFAOYSA-N ethenyl-dimethyl-phenylsilane Chemical compound C=C[Si](C)(C)C1=CC=CC=C1 QDEZCOQKJSRQNN-UHFFFAOYSA-N 0.000 description 1
- MRRXLWNSVYPSRB-UHFFFAOYSA-N ethenyl-dimethyl-trimethylsilyloxysilane Chemical compound C[Si](C)(C)O[Si](C)(C)C=C MRRXLWNSVYPSRB-UHFFFAOYSA-N 0.000 description 1
- CHEFFAKKAFRMHG-UHFFFAOYSA-N ethenyl-tris(trimethylsilyloxy)silane Chemical compound C[Si](C)(C)O[Si](O[Si](C)(C)C)(O[Si](C)(C)C)C=C CHEFFAKKAFRMHG-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- HYUPPKVFCGIMDB-UHFFFAOYSA-N ethyl 2-(4-hydroxyphenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(O)C=C1 HYUPPKVFCGIMDB-UHFFFAOYSA-N 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- ZWEDFBKLJILTMC-UHFFFAOYSA-N ethyl 4,4,4-trifluoro-3-hydroxybutanoate Chemical compound CCOC(=O)CC(O)C(F)(F)F ZWEDFBKLJILTMC-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000002828 fuel tank Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- PAIQEFSJYGYULU-UHFFFAOYSA-N heptadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCOC(=O)C(C)=C PAIQEFSJYGYULU-UHFFFAOYSA-N 0.000 description 1
- ZNAOFAIBVOMLPV-UHFFFAOYSA-N hexadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)C(C)=C ZNAOFAIBVOMLPV-UHFFFAOYSA-N 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 description 1
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- CFBXDFZIDLWOSO-UHFFFAOYSA-N icosyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCCCOC(=O)C(C)=C CFBXDFZIDLWOSO-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- DOULWWSSZVEPIN-UHFFFAOYSA-N isoproturon-monodemethyl Chemical compound CNC(=O)NC1=CC=C(C(C)C)C=C1 DOULWWSSZVEPIN-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- YGPZXPHFJSYIKP-UHFFFAOYSA-N nonadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCCOC(=O)C(C)=C YGPZXPHFJSYIKP-UHFFFAOYSA-N 0.000 description 1
- LKEDKQWWISEKSW-UHFFFAOYSA-N nonyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCOC(=O)C(C)=C LKEDKQWWISEKSW-UHFFFAOYSA-N 0.000 description 1
- MDYPDLBFDATSCF-UHFFFAOYSA-N nonyl prop-2-enoate Chemical compound CCCCCCCCCOC(=O)C=C MDYPDLBFDATSCF-UHFFFAOYSA-N 0.000 description 1
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 1
- NZIDBRBFGPQCRY-UHFFFAOYSA-N octyl 2-methylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C(C)=C NZIDBRBFGPQCRY-UHFFFAOYSA-N 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- PFPYHYZFFJJQFD-UHFFFAOYSA-N oxalic anhydride Chemical compound O=C1OC1=O PFPYHYZFFJJQFD-UHFFFAOYSA-N 0.000 description 1
- YOTGRUGZMVCBLS-UHFFFAOYSA-N pentadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCOC(=O)C(C)=C YOTGRUGZMVCBLS-UHFFFAOYSA-N 0.000 description 1
- ULDDEWDFUNBUCM-UHFFFAOYSA-N pentyl prop-2-enoate Chemical compound CCCCCOC(=O)C=C ULDDEWDFUNBUCM-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000005634 peroxydicarbonate group Chemical group 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- CDXZRBLOGJXGTN-UHFFFAOYSA-N prop-2-enoxycyclohexane Chemical compound C=CCOC1CCCCC1 CDXZRBLOGJXGTN-UHFFFAOYSA-N 0.000 description 1
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- YPVDWEHVCUBACK-UHFFFAOYSA-N propoxycarbonyloxy propyl carbonate Chemical compound CCCOC(=O)OOC(=O)OCCC YPVDWEHVCUBACK-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- QIFZBTPXXULUNF-UHFFFAOYSA-N tert-butyl-ethenyl-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)C=C QIFZBTPXXULUNF-UHFFFAOYSA-N 0.000 description 1
- ATZHWSYYKQKSSY-UHFFFAOYSA-N tetradecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCOC(=O)C(C)=C ATZHWSYYKQKSSY-UHFFFAOYSA-N 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- KEROTHRUZYBWCY-UHFFFAOYSA-N tridecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C(C)=C KEROTHRUZYBWCY-UHFFFAOYSA-N 0.000 description 1
- VJUIXFPWWBZVIL-UHFFFAOYSA-N trimethyl-[prop-2-enyl(trimethylsilyloxy)silyl]oxysilane Chemical compound C[Si](C)(C)O[SiH](CC=C)O[Si](C)(C)C VJUIXFPWWBZVIL-UHFFFAOYSA-N 0.000 description 1
- VGOXVARSERTCRY-UHFFFAOYSA-N trimethylsilylmethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC[Si](C)(C)C VGOXVARSERTCRY-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- RRLMGCBZYFFRED-UHFFFAOYSA-N undecyl prop-2-enoate Chemical compound CCCCCCCCCCCOC(=O)C=C RRLMGCBZYFFRED-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
- C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
- C08F230/085—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F214/18—Monomers containing fluorine
- C08F214/22—Vinylidene fluoride
- C08F214/225—Vinylidene fluoride with non-fluorinated comonomers
-
- 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
- C09D127/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers
- C09D127/02—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment
- C09D127/12—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
- C09D127/18—Homopolymers or copolymers of tetrafluoroethene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F214/18—Monomers containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F214/18—Monomers containing fluorine
- C08F214/26—Tetrafluoroethene
- C08F214/262—Tetrafluoroethene with fluorinated vinyl ethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F214/18—Monomers containing fluorine
- C08F214/26—Tetrafluoroethene
- C08F214/265—Tetrafluoroethene with non-fluorinated comonomers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/068—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
-
- 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
- C09D127/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers
- C09D127/02—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment
- C09D127/12—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
-
- 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
- C09D127/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers
- C09D127/02—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment
- C09D127/12—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
- C09D127/16—Homopolymers or copolymers of vinylidene fluoride
-
- 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
- C09D143/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing boron, silicon, phosphorus, selenium, tellurium, or a metal; Coating compositions based on derivatives of such polymers
- C09D143/04—Homopolymers or copolymers of monomers containing silicon
-
- 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
- C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
- C09D151/08—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C09D151/085—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds on to polysiloxanes
-
- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/63—Additives non-macromolecular organic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Paints Or Removers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
提供:具有长期稳定性的含氟共聚物组合物、以及使用该组合物的氟树脂涂料或清漆。一种组合物,其包含:含氟共聚物、溶剂和胺化合物,上述含氟共聚物是通过溶液聚合法使相对于氟代烯烃聚合单元5~85摩尔%为特定的乙烯系不饱和有机硅化合物聚合单元0.001~50摩尔%共聚而合成的;以及使用该组合物的氟树脂涂料或清漆;以及上述含氟共聚物组合物的制造方法。
Description
技术领域
本发明涉及一种拒水拒油性优异、具有作为氟树脂的特征的耐化学药品性、耐候性等优异特征、且与丙烯酸类树脂的相溶性优异的含氟共聚物;以及以其作为主成分的氟树脂涂料、清漆。
背景技术
溶剂可溶型的氟树脂涂料一般是将羟烷基乙烯基醚和氟代烯烃、以及根据需要的烷基乙烯基醚、烷基乙烯基酯等共聚而得到的。以该含氟共聚物为基础的涂料包含40%以上的烃单体,以获得对一般有机溶剂的溶解性。因此,氟树脂中的含氟量降低,不能充分得到含氟树脂所要求的拒水拒油性、耐污染性等涂膜特性。另一方面,通过在该含氟共聚物中混合少量的硅油等有机硅化合物,从而拒水拒油性提高。但是,难以维持长期的拒水拒油特性。另外,根据用途的不同,硅油会从涂膜表面渗出,因而也存在不能使用硅油的情况。另外,作为拒水拒油剂,对具有全氟基的含氟单体与含有甲硅烷基的单体的共聚物进行了研究,但由于共聚物的主骨架不具有氟原子,因此无法得到充分的耐候性。
申请人虽然提供了解决上述问题的溶剂可溶型的氟树脂涂料或清漆(专利文献1),但仍需要进一步改善稳定性。具体而言,在本领域,制造后需要长期保管(3个月以上)。包含含氟共聚物的溶液遇光时,溶液存在逐渐凝胶化的倾向。因此,若将氟树脂涂料或清漆放入容器中并静置,则经过6个月以上时存在粘度上升的倾向。
现有技术文献
专利文献
专利文献1:日本专利第4298117号公报
发明内容
发明要解决的问题
本发明的目的在于,提供一种具有长期稳定性的含氟共聚物组合物、以及使用该组合物的氟树脂涂料或清漆。
用于解决问题的方案
本发明提供以下内容。
[1]
一种组合物,其包含:
含氟共聚物,其包含5~85摩尔%的氟代烯烃、0.001~50摩尔%的选自通式(1)、(2)、(3)、(4)、(5)和(6)中的1种以上有机硅化合物作为聚合单元而构成;
溶剂;以及
胺化合物。
(其中,R1、R2和R3分别表示氢原子、甲基、乙基、丁基、苯基、-CF3、-C2H4CF3、-C(CH3)3或-OSi(CH3)3。R1、R2和R3任选彼此相同或不同。)
CH2=CR4-R5-(CH2)n-Si(CH3)2--〔O-Si(CH3)2〕m-OSi(CH3)2R6 (2)
CH2=CR4-COO-(CH2)n-Si(CH3)2--〔O-Si(CH3)2〕m-OSi(CH3)2R6 (3)
(其中,R4表示氢原子或甲基,R5表示醚基,R6表示氢原子或碳数1~6的烷基,n表示0~10,m表示0~420。)
(其中,R7表示氢原子或甲基,R8、R9和R10分别表示氢原子、甲基、乙基、丁基或-OSi(CH3)3。R8、R9和R10可以彼此相同或不同。p表示0~10。)
R11-〔Si(CH3)2-O〕q-Si(CH3)2-R12 (5)
(其中,R11表示碳数1~6的烷基或-(CH2)r-OOC(CH3)C=CH2或-(CH2)r-OOC-HC=CH2或-CH=CH2,R12表示-(CH2)r-OOC(CH3)C=CH2或-(CH2)r-OOC-HC=CH2或-CH=CH2,q表示1~420,r表示1~6。)
R12-Si〔OSi(CH3)3〕3 (6)
(其中,R12如前述定义。)
[2]
根据[1]所述的组合物,其特征在于,前述含氟共聚物还包含选自烷基乙烯基醚、烷基烯丙基醚、乙烯基酯、甲基丙烯酸酯和丙烯酸酯中的1种以上聚合单元而构成。
[3]
根据[1]或[2]所述的组合物,其中,每100重量份前述含氟共聚物,包含0.005~10重量份的前述胺化合物。
[4]
根据[3]所述的组合物,其中,每100重量份含氟共聚物,包含25~1900重量份的溶剂。
更详细而言,根据[1]或[2]所述的组合物,其中,
每100重量份含氟共聚物,包含:
溶剂25~1900重量份、优选43~900重量份、更优选67~400重量份;以及
胺化合物0.005~10重量份、优选0.05~10重量份、更优选0.05~5重量份。
[5]
根据[1]~[4]中任一项所述的组合物的制造方法,其包括工序(a):利用溶液聚合法使前述聚合单元共聚而生成包含含氟共聚物的溶液。
[6]
根据[5]所述的方法,其中,还包括工序(b):在工序(a)得到的包含含氟共聚物的溶液中加入胺化合物。
[7]
根据[5]或[6]所述的方法,其中,使用选自由乙酸乙酯、乙酸丁酯、二甲苯、甲苯和甲乙酮组成的组中的至少1种作为溶剂进行工序(a)的共聚。
[8]
—种清漆或涂料,其由[1]~[4]中任一项所述的组合物形成。
[9]
一种方法,其中,将由[1]~[4]中任一项所述的组合物形成的清漆或涂料用于选自由照相凹版涂布机、旋转涂布机、浸渍(Dip)涂覆、辊涂布机、逆转辊涂布机、逗号涂布机、刮刀涂布机、棒涂机、辊舐涂布机、淋幕式涂布机、辊涂覆、喷雾涂覆、静电喷雾涂覆、轮转丝网印刷、喷墨涂覆和刷毛涂布组成的组中的涂布方法。
[10]
一种涂膜,其利用[9]所述的清漆或涂料与涂布方法而形成。
发明的效果
根据本发明,提供具有长期稳定性的含氟共聚物组合物、以及使用该组合物的氟树脂涂料或清漆。根据本发明,还提供上述含氟共聚物组合物的制造方法。根据本发明,进一步提供将上述氟树脂涂料或清漆用于选自由照相凹版涂布机、旋转涂布机、浸渍(Dip)涂覆、辊涂布机、逆转辊涂布机、逗号涂布机、刮刀涂布机、棒涂机、辊舐涂布机、淋幕式涂布机、辊涂覆、喷雾涂覆、静电喷雾涂覆、轮转丝网印刷、喷墨涂覆和刷毛涂布组成的组中的涂布方法中的方法、以及利用上述清漆或涂料与涂布方法而形成的涂膜。
具体实施方式
[作用]
本发明的特征在于,以特定范围的量使用胺化合物作为稳定剂。已知的是,一般在含有硅油等有机硅化合物的反应体系中添加胺化合物时,反应液会黄变。因此,胺化合物一直并未用于含有有机硅化合物的涂料或清漆的稳定剂。对于本发明的含氟共聚物,其聚合单元是有机硅化合物,因而也是高分子量的有机硅化合物,若使用胺化合物作为稳定剂则担心着色等问题。然而,根据本发明人等的研究,预料不到地发现:通过将胺化合物的添加量选择为特定的范围,从而可以将着色程度等抑制为最小限度,并制造出消除了着色等问题的长期稳定性优异的含氟共聚物组合物。由于着色等问题得以消除,因此本发明的含氟共聚物组合物作为涂料或清漆也是有用的。
[含氟共聚物组合物]
本发明的含氟共聚物组合物包含:
含氟共聚物,其包含5~85摩尔%的氟代烯烃、0.001~50摩尔%的选自前述通式(1)、(2)、(3)、(4)、(5)和(6)中的1种以上有机硅化合物作为聚合单元而构成;
溶剂;以及
胺化合物。
[含氟共聚物]
对于选自下述通式(1)、(2)、(3)、(4)、(5)和(6)中的1种以上有机硅化合物与氟代烯烃的共聚物,长期的拒水拒油性、反复的污染去除性、耐化学药品性、耐候性优异,在各种用途中是有用的。本发明还提供一种含氟共聚物,其特征在于,除上述聚合单元以外,还包含选自烷基乙烯基醚、烷基烯丙基醚、乙烯基酯、甲基丙烯酸酯和丙烯酸酯中的1种以上聚合单元而构成。需要说明的是,在本说明书中,“-COO-”或“-OOC-”表示酯键。
(其中,R1、R2和R3分别表示氢原子、甲基、乙基、丁基、苯基、-CF3、-C2H4CF3、-C(CH3)3或-OSi(CH3)3。R1、R2和R3任选彼此相同或不同。)
CH2=CR4-R5-(CH2)n-Si(CH3)2-〔O-Si(CH3)2〕m-OSi(CH3)2R6 (2)
CH2=CR4-COO-(CH2)n-Si(CH3)2-〔O-Si(CH3)2〕m-OSi(CH3)2R6 (3)
(其中,R4表示氢原子或甲基,R5表示醚基(即-O-),R6表示氢原子或碳数1~6的烷基,n表示0~10,m表示0~420、特别表示0~160。)
(其中,R7表示氢原子或甲基,R8、R9和R10分别表示氢原子、甲基、乙基、丁基(例如正丁基、异丁基、叔丁基、仲丁基等)或-OSi(CH3)3。R8、R9和R10可以彼此相同或不同。p表示0~10。)
R11-〔Si(CH3)2-O〕q-Si(CH3)2-R12 (5)
(其中,R11表示碳数1~6的烷基或-(CH2)r-OOC(CH3)C=CH2或-(CH2)r-OOC-HC=CH2或-CH=CH2,R12表示-(CH2)r-OOC(CH3)C=CH2或-(CH2)r-OOC-HC=CH2或-CH=CH2,q表示1~420,r表示1~6。)
R12-Si〔OSI(CH3)3〕3 (6)
(其中,R12如前述定义。)
在本发明的共聚物中,氟代烯烃是分子中具有1个以上氟原子的烯烃,例如偏二氟乙烯、四氟乙烯、氯三氟乙烯、六氟丙烯等是合适的。这些氟代烯烃可以各自单独使用,也可以组合2种以上。
作为通式(1)、(2)、(3)、(4)、(5)和(6)所示的有机硅化合物的具体例,乙烯基五甲基二硅氧烷、乙烯基苯基二甲基硅烷、乙烯基甲基双(三甲基硅氧基)硅烷、乙烯基三乙基硅烷、乙烯基(三氟甲基)二甲基硅烷、乙烯基(3,3,3-三氟丙基)二甲基硅烷、乙烯基三甲基硅烷、乙烯基三(三甲基硅氧基)硅烷、乙烯基叔丁基二甲基硅烷、乙烯基二乙基甲基硅烷、(3-丙烯酰氧基丙基)甲基双(三甲基硅氧基)硅烷、3-甲基丙烯酰氧基丙基双(三甲基硅氧基)甲基硅烷、(3-丙烯酰氧基丙基)三(三甲基硅氧基)硅烷、甲基丙烯酰氧基丙基三(三甲基硅氧基)硅烷、甲基丙烯酰氧基甲基三甲基硅烷、一末端经甲基丙烯酰基改性的反应性硅油、一末端经丙烯酰基改性的反应性硅油、两末端经甲基丙烯酰基改性的反应性硅油、两末端经丙烯酰基改性的反应性硅油、由通式(7)、(8)、(9)和(10)所示的有机硅化合物等是合适的。这些有机硅化合物可以各自单独使用,也可以组合2种以上。这些有机硅化合物的分子量优选为100~30000。
CH2=C(CH3)-COO-C3H6-Si(CH3)2-〔O-Si(CH3)2〕a-R13 (7)
(其中,-C3H6-表示亚丙基,R13表示碳数1~6的烷基,a表示1~250。)
CH2=CH-COO-C3H6-Si(CH3)2-〔O-Si(CH3)2〕a-R13 (8)
(其中,-C3H6-表示亚丙基,R13表示碳数1~6的烷基,a表示1~250。)
R14-C3H6-Si(CH3)2-〔O-Si(CH3)2〕b-C3H6-R14 (9)
(其中,R14表示-OOC(CH3)C=CH2,b表示1~250)。
CH2=C(CH3)COO-C3H6-Si〔OSi(CH3)3〕3 (10)
(其中,-C3H6-表示亚丙基)。
作为烷基乙烯基醚的具体例,可举出:甲基乙烯基醚、乙基乙烯基醚、异丙基乙烯基醚、正丙基乙烯基醚、正丁基乙烯基醚、异丁基乙烯基醚、正戊基乙烯基醚、异戊基乙烯基醚、叔戊基乙烯基醚、正己基乙烯基醚、异己基乙烯基醚、2-乙基己基乙烯基醚、正庚基乙烯基醚、正辛基乙烯基醚、正壬基乙烯基醚、正癸基乙烯基醚、正十一烷基乙烯基醚、正十二烷基乙烯基醚、正十三烷基乙烯基醚、正十四烷基乙烯基醚、正十五烷基乙烯基醚、正十六烷基乙烯基醚、正十七烷基乙烯基醚、正十八烷基乙烯基醚、正十九烷基乙烯基醚、正二十烷基乙烯基醚、环己基乙烯基醚、十八烷基乙烯基醚、缩水甘油基乙烯基醚、缩水甘油基氧基甲基乙烯基醚、缩水甘油基氧基乙基乙烯基醚、缩水甘油基氧基丁基乙烯基醚、缩水甘油基氧基戊基乙烯基醚、缩水甘油基氧基环己基乙烯基醚、羟基甲基乙烯基醚、羟基乙基乙烯基醚、羟基丙基乙烯基醚、羟基丁基乙烯基醚、羟基戊基乙烯基醚、羟基己基乙烯基醚、羟基庚基乙烯基醚、羟基辛基乙烯基醚、羟基壬基乙烯基醚、羟基癸基乙烯基醚、羟基十一烷基乙烯基醚、羟基十二烷基乙烯基醚、羟基十三烷基乙烯基醚、羟基十四烷基乙烯基醚、羟基十五烷基乙烯基醚、羟基十六烷基乙烯基醚、羟基十七烷基乙烯基醚、羟基十八烷基乙烯基醚、羟基十九烷基乙烯基醚、羟基二十烷基乙烯基醚、二乙二醇单乙烯基醚、三乙二醇单乙烯基醚、乙二醇单烯丙基醚、环己基乙烯基醚、4-羟基环己基乙烯基醚等
作为烷基烯丙基醚的具体例,可举出:乙基烯丙基醚、丁基烯丙基醚、环己基烯丙基醚、异丁基烯丙基醚、正丙基烯丙基醚、烯丙基缩水甘油基醚、3-烯丙氧基-1,2-丙二醇、甘油-α-单烯丙基醚、乙二醇单烯丙基醚等。
作为丙烯酸酯的具体例,可举出:丙烯酸甲酯、丙烯酸乙酯、丙烯酸正丁酯、丙烯酸叔丁酯、丙烯酸正丙酯、丙烯酸异丙酯、丙烯酸正丁酯、丙烯酸异丁酯、丙烯酸正戊酯、丙烯酸异戊酯、丙烯酸正己酯、丙烯酸2-乙基己酯、丙烯酸正庚酯、丙烯酸正辛酯、丙烯酸正壬酯、丙烯酸正癸酯、丙烯酸正十一烷基酯、丙烯酸正十二烷基酯、丙烯酸2-羟基乙酯、丙烯酸2-羟基丁酯、丙烯酸2,2,2-三氟乙酯等。
作为甲基丙烯酸酯的具体例,可举出:甲基丙烯酸甲酯、甲基丙烯酸乙酯、甲基丙烯酸正丁酯、甲基丙烯酸叔丁酯、甲基丙烯酸正己酯、甲基丙烯酸2-乙基己酯、甲基丙烯酸正庚酯、甲基丙烯酸正辛酯、甲基丙烯酸正壬酯、甲基丙烯酸正癸酯、甲基丙烯酸正十一烷基酯、甲基丙烯酸正十二烷基酯、甲基丙烯酸正十三烷基酯、甲基丙烯酸正十四烷基酯、甲基丙烯酸正十五烷基酯、甲基丙烯酸正十六烷基酯、甲基丙烯酸正十七烷基酯、甲基丙烯酸正十八烷基酯、甲基丙烯酸正十九烷基酯、甲基丙烯酸正二十烷基酯、甲基丙烯酸缩水甘油酯、甲基丙烯酸环己酯、甲基丙烯酸2-羟基乙酯、甲基丙烯酸2-羟基丙酯、甲基丙烯酸3-羟基丙酯、甲基丙烯酸4-羟基丁酯、甲基丙烯酸2,2,2-三氟乙酯等。
作为乙烯基酯,具体可举出:乙酸乙烯基酯、正丁酸乙烯基酯、异丁酸乙烯基酯、丙酸乙烯基酯、己酸乙烯基酯、辛酸乙烯基酯、癸酸乙烯基酯、月桂酸乙烯基酯、肉豆蔻酸乙烯基酯、棕榈酸乙烯基酯、硬脂酸乙烯基酯等羧酸乙烯基酯类等。
本发明的含氟共聚物可以形成长期的拒水拒油性、反复的污染去除性、耐化学药品性、耐候性优异的涂膜,此外,除了这些单元以外,还可以根据使用目的等在不超过20摩尔%的范围内包含其它的可共聚单体单元。
作为该其它的可共聚单体,例如可举出:乙烯、丙烯等烯烃类;氯乙烯、偏二氯乙烯等卤代烯烃类;2-(全氟己基)乙基乙烯基醚等卤代乙烯基醚类;甲基丙烯酸2-(全氟丁基)乙酯、甲基丙烯酸2-(全氟己基)乙酯等卤代甲基丙烯酸酯类;丙烯酸2-(全氟丁基)乙酯、丙烯酸2-(全氟己基)乙酯等卤代丙烯酸酯类。
在该含氟共聚物中聚合单元氟代烯烃少于5摩尔%时,用作涂料基时无法得到充分的耐污染性,是不优选的。另外在大于85摩尔%时,对各种溶剂的溶解性降低,是不优选的。优选为30~80摩尔%。另外,在选自通式(1)、(2)、(3)、(4)、(5)和(6)中的有机硅化合物的比例少于0.001摩尔%时,无法得到长期的充分拒水拒油性,是不优选的。另外在大于50摩尔%时,无法得到充分的耐化学药品性、耐候性,是不优选的。该有机硅化合物的比例优选为0.005~30摩尔%。
本发明的含氟共聚物可以如下制造:使用聚合引发剂通过溶液聚合法使规定比例的单体混合物进行共聚,从而制造。
作为溶液聚合法中使用的聚合引发剂,例如可使用:过氧化异丁酸叔丁酯、过氧化乙酸叔丁酯等过氧酯型过氧化物;过氧化二碳酸二异丙酯、过氧化二碳酸二正丙酯等过氧化二碳酸二烷基酯;过氧化苯甲酰、偶氮双异丁腈等。聚合引发剂的用量根据其种类、共聚反应条件等适当选择,通常在相对于所使用的聚合单元(单体)总量为0.005~5重量%、优选0.1~2重量%的范围内进行选择。
作为用于通过溶液聚合法得到本发明的含氟共聚物的特别优选的溶剂,例如可举出乙酸乙酯、乙酸丁酯、二甲苯、甲苯、甲乙酮等。
共聚反应中的反应温度通常在0℃~100℃、优选10℃~90℃的范围内进行选择。另外,对于反应压力没有特别限制,通常在0.1~10MPa、优选0.1~5MPa的范围内进行选择。进一步,该共聚反应可以添加适当的链转移剂而进行。
在本发明的含氟共聚物含有羟基作为固化部位的情况下,可以使用多元异氰酸酯类在常温下进行固化。作为该多元异氰酸酯类,例如可优选举出:六亚甲基二异氰酸酯、异佛尔酮二异氰酸酯等无黄变性的二异氰酸酯或其加成物;具有异氰脲酸酯类的多元异氰酸酯,其中,具有异氰脲酸酯类的多元异氰酸酯是特别有效的。在使用异氰酸酯类进行常温固化时,也可以通过添加二月桂酸二丁基锡等公知催化剂来促进固化。
进一步,也可以使用三聚氰胺固化剂、脲树脂固化剂、多元酸固化剂等进行加热固化。作为该三聚氰胺固化剂,例如可举出丁基化三聚氰胺、甲基化三聚氰胺、环氧改性三聚氰胺等,根据用途适当使用各种改性度的固化剂,此外还可以适当选择自缩合度。作为脲树脂固化剂,例如可举出甲基化脲树脂、丁基化脲树脂等,作为多元酸固化剂,例如可举出长链脂肪族二羧酸、芳香族多元羧酸类以及它们的酸酐等。
进一步,封端化多元异氰酸酯类也可以适合地用作固化剂。此外,在使用三聚氰胺固化剂或脲树脂固化剂时,也可以通过添加酸性催化剂而促进固化。
另外,在本发明的含氟共聚物含有环氧基作为固化部位的情况下,可举出通常的固化性环氧涂料中使用的固化剂,例如有二亚乙基三胺、三亚乙基四胺、四亚乙基五胺等这样的脂肪族胺类或其改性物;间苯二胺、p,p'-二氨基二苯基甲烷、二氨基苯基砜等这样的芳香族胺类或其改性物;苯二甲酸酐、马来酸酐、草酸酐、六氢苯二甲酸、庚二酸等多元羧酸或其酸酐等。
[溶剂]
在制造以本发明的含氟共聚物为主成分的氟树脂涂料或清漆、或者固化性氟树脂涂料或清漆时,可使用各种溶剂,例如可举出:二甲苯、甲苯等芳族烃类;乙酸乙酯、乙酸丁酯等乙酸酯类;甲乙酮、甲基异丁基酮等酮类;乙二醇乙醚等二醇醚类;市售的各种稀释剂类等,特别优选乙酸乙酯、乙酸丁酯、二甲苯、甲苯。另外,可根据需要添加丙烯酸类树脂、环氧树脂。优选对含氟共聚物进行调节以使涂料中包含5~80重量%、特别是20~60重量%并使用。
[胺化合物]
在本发明中,使用胺化合物作为稳定剂。作为胺化合物,可举出伯胺、仲胺、叔胺等有机胺。并且,作为叔胺,优选三烷基胺,特别可举出:具有碳数1~4的低级烷基的三烷基胺,例如有三甲胺、三乙胺、三丁胺等。在胺化合物之中,出于作为稳定剂的性能、着色程度、获得容易性等理由,特别优选三乙胺、三丁胺(特别是三异丁胺)。
[含氟共聚物组合物的制造方法]
在用于制造本发明的含氟共聚物组合物的本发明的含氟共聚物与溶剂的混合中,可以使用球磨机、油漆搅拌器、砂磨机、三辊磨机、捏合机等常规涂料化中所使用的各种设备来进行。此时,还可以根据需要添加作为本发明的组合物的必需成分的胺化合物,并进一步添加丙烯酸类树脂、颜料、分散稳定剂、粘度调节剂、流平剂、紫外线吸收剂等任意成分。由于本发明的含氟共聚物通过溶液聚合法来制造,所以聚合后的反应液中包含含氟共聚物和溶剂作为主要成分,在该反应液中加入规定量的胺化合物,可以制成本发明的含氟共聚物组合物。
胺化合物的添加量优选为本发明的含氟共聚物的总重量的0.005~10重量%、更优选为0.05~10重量%、进一步优选为0.05~5重量%。即,胺化合物的添加量优选每100重量份前述含氟共聚物以0.005~10重量份的比例含有、更优选以0.05~10重量份的比例含有、进一步优选以0.05~5重量份的比例含有。在胺化合物的量过少时,存在难以长期防止凝胶化的倾向。另一方面,在胺化合物的量过多时,对于得到相同的稳定化效果来说,造成稳定剂的浪费,存在着色等的程度无法忽视的倾向。
[含氟共聚物组合物的用途]
本发明的含氟共聚物组合物的长期保存稳定性优异,保存3个月之后实质上也不会引起粘度的上升、色相的变化。因此,适于涂料、清漆的用途。具体而言,由本发明的含氟共聚物组合物制备的涂料或清漆适于照相凹版涂布机、旋转涂布机、浸渍(Dip)涂覆、辊涂布机、逆转辊涂布机、逗号涂布机、刮刀涂布机、棒涂机、辊舐涂布机、淋幕式涂布机、辊涂覆、喷雾涂覆、静电喷雾涂覆、轮转丝网印刷、喷墨涂覆、刷毛涂布等涂布方法。
作为涂装物品的用途,可以在例如下述举出的广泛用途中进行利用。作为外饰用途,例如可举出:汽车外饰涂装、汽车外饰涂装膜、汽车涂装保护膜、汽车窗户膜、汽车标记膜等车辆用外饰膜类。具体而言,可以举出汽车车体、保险杠、扰流片、门把手、车前灯、闪光灯、后视镜、发动机散热窗、车轮等汽车外饰和外饰部件类。此外,可以举出摩托车车体、把手、车座、油箱等摩托车外饰和外饰部件类。可以举出其他列车等车辆类的外饰、外饰膜、外饰部件。此外,可以举出汽车、摩托车、列车等车辆中的窗户膜、玻璃表面涂布、标记膜、保护膜、涂装等。此外,作为汽车等车辆中的内饰用途,可以举出汽车内饰片材、把手、仪表面板、控制面板、仪表板、门内饰等用途、和这些用途中的涂料、保护膜、设计性膜等。
作为除这些以外的用途,例如可举出:脱模薄膜或移动电话、智能手机、个人电脑、电视、移动终端(包括游戏机)、打印机等电子设备、电视、空调、微波炉、冰箱、洗衣机、空气净化器、吸尘器、换气扇等家电类、玩具类、架子、书架、床、桌子、椅子、沙发等家具类、换气扇、抽油烟机、厨房面板、不锈钢水槽、浴槽、卫生间等用途、和这些用途中的涂料、保护膜、设计性膜等。此外,可以举出建筑物等中的窗户膜、玻璃表面涂布、室外标记膜、各种物品的保护膜、建材用涂装等。
实施例
接下来通过实施例对本发明进行更详细的说明,但本发明并不限定于这些例子。
(实施例1)
在内容积1L的带不锈钢制搅拌机的高压釜(压力:10MPa)中,在脱气后,加入偏二氟乙烯(以下简称为VDF)4.7g、四氟乙烯(以下简称为TFE)29.6g、下述式:
CH2=C(CH3)-COO-(CH2)3-Si(CH3)2-〔O-Si(CH3)2〕60-OSi(CH3)2-(CH2)3-CH3
所示的有机硅化合物11.4g、羟基丁基乙烯基醚(以下简称为HBVE)42.7g、环己基乙烯基醚(以下简称为CHVE)46.7g、甲基丙烯酸甲酯(以下简称为MMA)136.0g、乙酸丁酯400g、甲乙酮50g及过氧化新戊酸叔丁酯5g,一边搅拌一边将内温升温至60℃。之后,一边搅拌一边继续反应,20小时后停止搅拌,结束反应。刚聚合反应后的反应液的外观为无色透明液体。
通过反应液的气相色谱(GC)分析,聚合物收率(含氟共聚物收率)为236g,单体反应率为87%。在包含所得到的共聚物、乙酸丁酯和甲乙酮的反应液中加入三异丁胺0.71g,得到本发明的含氟共聚物组合物。另行分离得到共聚物,得到的共聚物的利用乙酸酐的乙酰基化法测定的羟值为88mgKOH/g树脂,利用燃烧法测定的氟含量为8.0wt%,通过GPC测定的数均分子量为2.0×104。通过如下方法对所得到的含氟共聚物组合物的特性进行考察。结果示于[表1]。
[涂膜的制作]
在所得到的含氟共聚物组合物中加入CORONATE HX[日本聚氨酯工业(株)制]以使该聚合物(含氟共聚物)的羟基/NCO基为1/1.1,利用乙酸丁酯稀释至固体成分浓度为29%从而对涂剂进行调整,用#40的棒涂机涂布在调整玻璃板上,在80℃下加热处理24小时,从而制作厚度25μm的涂膜,并进行评价。
[保存稳定性]
使用石油产品色度仪OME 2000(日本电色工业株式会社制),对50℃下保存14天后的含氟共聚物组合物的加德纳色度进行测定,并进行评价。作为保存稳定性的促进试验,对50℃下保存14天后的结果进行评价。这是因为,本领域认为50℃下保管14天相当于常温下保管6个月。
[涂膜黄色度(YI)]
利用手持式分光色差计NR 555(日本电色工业株式会社制)测量涂膜的黄色度(YI)。
[雾度(HAZE)]
利用雾度计HM-150L2(株式会社村上色彩技术研究所制)测定涂膜的雾度(HAZE)。
(实施例2~10、比较例1~4)
使用[表1]所示的单体并依照上述实施例1的操作来制造共聚物和共聚物组合物,并同样地对它们的特性进行考察。结果示于[表1]。需要注意的是,比较例1~4是不在本发明范围内的比较例。另外,表1中,胺化合物的量以反应液中的聚合物收率(含氟共聚物收率)设为100重量份时的重量份来表示。
[表1]
(1)氟代烯烃
VDF:偏二氟乙烯
TFE:四氟乙烯
(2)有机硅化合物的结构式:
n=60:
CH2=C(CH3)-COO-(CH2)3-Si(CH3)2-〔O-Si(CH3)2〕60-OSi(CH3)2-(CH2)3-CH3
n=150:
CH2=C(CH3)-COO-(CH2)3-Si(CH3)2-〔O-Si(CH3)2〕150-OSi(CH3)2-(CH2)3-CH3
(3)含羟基(OH基)
DEGMVE:二乙二醇单乙烯基醚
HBVE:羟基丁基乙烯基醚
(4)无羟基(OH基)
CHVE:环己基乙烯基醚
n-BVE:正丁基乙烯基醚
MMA:甲基丙烯酸甲酯
可知,每100重量份含氟共聚物以0.005重量份~10重量份的范围包含胺化合物的本发明的含氟共聚物组合物即便在50℃下保存14天后,加德纳色度也低至1~3,涂膜黄色度(YI)为8.32以下,浊度为41.9以下,几乎不引起变色等。而使用4摩尔%氟代烯烃的比较例1的单体混合物未发生聚合反应,无法得到含氟共聚物。对于使用90摩尔%氟代烯烃的比较例2的含氟共聚物组合物,由于是白浊高粘稠液体,因此未进行后续的评价。不含胺化合物的比较例3和4分别自保管开始起第7天和第5天发生凝胶化。根据表1记载的试验结果可知,通过将胺化合物的添加量选择为特定的范围,从而可以将着色程度等抑制为最小限度,并制造出消除了着色等问题的长期稳定性优异的含氟共聚物组合物。由于着色等问题得以消除,所以本发明的含氟共聚物组合物作为涂料或清漆也是有用的。
Claims (10)
1.一种组合物,其包含:
含氟共聚物,其包含5~85摩尔%的氟代烯烃、0.001~50摩尔%的选自通式(1)、(2)、(3)、(4)、(5)和(6)中的1种以上有机硅化合物作为聚合单元而构成;
溶剂;以及
胺化合物,
其中,R1、R2和R3分别表示氢原子、甲基、乙基、丁基、苯基、-CF3、-C2H4CF3、-C(CH3)3或-OSi(CH3)3,R1、R2和R3任选彼此相同或不同,
CH2=CR4-R5-(CH2)n-Si(CH3)2-
-〔O-Si(CH3)2〕m-OSi(CH3)2R6 (2)
CH2=CR4-COO-(CH2)n-Si(CH3)2-
-〔O-Si(CH3)2〕m-OSi(CH3)2R6 (3)
其中,R4表示氢原子或甲基,R5表示醚基,R6表示氢原子或碳数1~6的烷基,n表示0~10,m表示0~420,
其中,R7表示氢原子或甲基,R8、R9和R10分别表示氢原子、甲基、乙基、丁基或-OSi(CH3)3,R8、R9和R10可以彼此相同或不同,p表示0~10,
R11-〔Si(CH3)2-O〕q-Si(CH3)2-R12 (5)
其中,R11表示碳数1~6的烷基或-(CH2)r-OOC(CH3)C=CH2或-(CH2)r-OOC-HC=CH2或-CH=CH2,R12表示-(CH2)r-OOC(CH3)C=CH2或-(CH2)r-OOC-HC=CH2或-CH=CH2,q表示1~420,r表示1~6,
R12-Si〔OSi(CH3)3〕3 (6)
其中,R12如前述定义。
2.根据权利要求1所述的组合物,其特征在于,所述含氟共聚物还包含选自烷基乙烯基醚、烷基烯丙基醚、乙烯基酯、甲基丙烯酸酯和丙烯酸酯中的1种以上聚合单元而构成。
3.根据权利要求1或2所述的组合物,其中,每100重量份所述含氟共聚物,包含0.005~10重量份的所述胺化合物。
4.根据权利要求3所述的组合物,其中,每100重量份含氟共聚物,包含25~1900重量份的溶剂。
5.根据权利要求1~4中任一项所述的组合物的制造方法,其包括工序(a):利用溶液聚合法使所述聚合单元共聚而生成包含含氟共聚物的溶液。
6.根据权利要求5所述的方法,其还包括工序(b):在工序(a)得到的包含含氟共聚物的溶液中加入胺化合物。
7.根据权利要求5或6所述的方法,其中,使用选自由乙酸乙酯、乙酸丁酯、二甲苯、甲苯和甲乙酮组成的组中的至少1种作为溶剂进行工序(a)的共聚。
8.一种清漆或涂料,其由权利要求1~4中任一项所述的组合物形成。
9.一种方法,其中,将由权利要求1~4中任一项所述的组合物形成的清漆或涂料用于选自由照相凹版涂布机、旋转涂布机、浸渍(Dip)涂覆、辊涂布机、逆转辊涂布机、逗号涂布机、刮刀涂布机、棒涂机、辊舐涂布机、淋幕式涂布机、辊涂覆、喷雾涂覆、静电喷雾涂覆、轮转丝网印刷、喷墨涂覆和刷毛涂布组成的组中的涂布方法。
10.一种涂膜,其利用权利要求9所述的清漆或涂料与涂布方法而形成。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2020-029783 | 2020-02-25 | ||
JP2020029783 | 2020-02-25 | ||
PCT/JP2021/006774 WO2021172322A1 (ja) | 2020-02-25 | 2021-02-24 | 含フッ素共重合体組成物 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN115210314A true CN115210314A (zh) | 2022-10-18 |
Family
ID=77489964
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202180016797.2A Pending CN115210314A (zh) | 2020-02-25 | 2021-02-24 | 含氟共聚物组合物 |
Country Status (6)
Country | Link |
---|---|
US (1) | US20230109353A1 (zh) |
JP (1) | JPWO2021172322A1 (zh) |
KR (1) | KR20220144365A (zh) |
CN (1) | CN115210314A (zh) |
TW (1) | TW202140583A (zh) |
WO (1) | WO2021172322A1 (zh) |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH05271349A (ja) * | 1992-03-30 | 1993-10-19 | Central Glass Co Ltd | 塗料用樹脂の製造法 |
JP2000313725A (ja) * | 1999-03-04 | 2000-11-14 | Kanto Denka Kogyo Co Ltd | 含フッ素共重合体およびその製造方法 |
JP2001206918A (ja) * | 2000-01-28 | 2001-07-31 | Kanto Denka Kogyo Co Ltd | 硬化性含フッ素共重合体およびその製造方法 |
JP2011208043A (ja) * | 2010-03-30 | 2011-10-20 | Daikin Industries Ltd | 溶剤型耐候性塗料組成物 |
CN110461963A (zh) * | 2017-03-29 | 2019-11-15 | 关东电化工业株式会社 | 涂料组合物 |
CN110494459A (zh) * | 2017-04-17 | 2019-11-22 | 关东电化工业株式会社 | 含氟共聚物 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3029323B2 (ja) * | 1990-06-01 | 2000-04-04 | 旭硝子株式会社 | コーティング用含フッ素重合体組成物およびその用途 |
JPH06184243A (ja) * | 1992-12-22 | 1994-07-05 | Daikin Ind Ltd | 含フッ素共重合体 |
JP4306292B2 (ja) * | 2002-06-14 | 2009-07-29 | ダイキン工業株式会社 | 含フッ素共重合体および塗料用組成物 |
JP5212561B1 (ja) * | 2011-03-31 | 2013-06-19 | ダイキン工業株式会社 | 含フッ素共重合体 |
-
2021
- 2021-02-24 JP JP2022503632A patent/JPWO2021172322A1/ja active Pending
- 2021-02-24 KR KR1020227027082A patent/KR20220144365A/ko unknown
- 2021-02-24 US US17/904,520 patent/US20230109353A1/en active Pending
- 2021-02-24 TW TW110106439A patent/TW202140583A/zh unknown
- 2021-02-24 CN CN202180016797.2A patent/CN115210314A/zh active Pending
- 2021-02-24 WO PCT/JP2021/006774 patent/WO2021172322A1/ja active Application Filing
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH05271349A (ja) * | 1992-03-30 | 1993-10-19 | Central Glass Co Ltd | 塗料用樹脂の製造法 |
JP2000313725A (ja) * | 1999-03-04 | 2000-11-14 | Kanto Denka Kogyo Co Ltd | 含フッ素共重合体およびその製造方法 |
JP2001206918A (ja) * | 2000-01-28 | 2001-07-31 | Kanto Denka Kogyo Co Ltd | 硬化性含フッ素共重合体およびその製造方法 |
JP2011208043A (ja) * | 2010-03-30 | 2011-10-20 | Daikin Industries Ltd | 溶剤型耐候性塗料組成物 |
CN110461963A (zh) * | 2017-03-29 | 2019-11-15 | 关东电化工业株式会社 | 涂料组合物 |
CN110494459A (zh) * | 2017-04-17 | 2019-11-22 | 关东电化工业株式会社 | 含氟共聚物 |
Also Published As
Publication number | Publication date |
---|---|
TW202140583A (zh) | 2021-11-01 |
US20230109353A1 (en) | 2023-04-06 |
JPWO2021172322A1 (zh) | 2021-09-02 |
WO2021172322A1 (ja) | 2021-09-02 |
KR20220144365A (ko) | 2022-10-26 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR100494864B1 (ko) | 함불소계중합체수성분산액 | |
US9018306B2 (en) | Curable fluorine-containing polymer composition | |
CN110494459B (zh) | 含氟共聚物 | |
KR20010072787A (ko) | 불소계 공중합체의 수성분산액 및 수성도료용 조성물 | |
US9127114B2 (en) | Curable fluorine-containing polymer composition | |
JP4068786B2 (ja) | 硬化塗膜の形成方法 | |
JP2000313725A (ja) | 含フッ素共重合体およびその製造方法 | |
JP4754546B2 (ja) | 二重結合を含有する含フッ素共重合体硬化塗膜 | |
EP3013876B1 (en) | Moisture-curable composition, method of using, and composite article | |
JP4068782B2 (ja) | 二重結合含有含フッ素共重合体の製造方法 | |
CN115210314A (zh) | 含氟共聚物组合物 | |
JP3093345B2 (ja) | シリル基を有する含フッ素共重合体を含有する塗料用組成物 | |
JP2003192749A (ja) | 二重結合を含有する重合体液状組成物とその製造方法 | |
JP2712584B2 (ja) | 含フッ素共重合体及び塗料用組成物 | |
JP2001206918A (ja) | 硬化性含フッ素共重合体およびその製造方法 | |
JP3638076B2 (ja) | 水性塗料用水性フッ素樹脂組成物 | |
JP4732560B2 (ja) | 樹脂組成物 | |
JP4754545B2 (ja) | 二重結合含有含フッ素共重合体を主成分とするフッ素系ワニス | |
JP4213257B2 (ja) | 含フッ素共重合体及びその製造方法 | |
JP4087030B2 (ja) | 含フッ素共重合体およびその製造方法 | |
JPH08120212A (ja) | フッ素樹脂塗料用組成物 | |
JP2000017022A (ja) | フッ素含有樹脂およびフッ素含有樹脂組成物 | |
JPH08120213A (ja) | フッ素樹脂塗料用組成物 | |
JPH0539326A (ja) | 脂環式エポキシ基含有含フツ素共重合体の製造方法 | |
JPH04164905A (ja) | 含フッ素共重合体および硬化用組成物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
WD01 | Invention patent application deemed withdrawn after publication | ||
WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20221018 |