JPS6333513B2 - - Google Patents
Info
- Publication number
- JPS6333513B2 JPS6333513B2 JP55124661A JP12466180A JPS6333513B2 JP S6333513 B2 JPS6333513 B2 JP S6333513B2 JP 55124661 A JP55124661 A JP 55124661A JP 12466180 A JP12466180 A JP 12466180A JP S6333513 B2 JPS6333513 B2 JP S6333513B2
- Authority
- JP
- Japan
- Prior art keywords
- triphenyltin
- antifouling
- paint
- columnar
- methacrylate
- 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.)
- Expired
Links
- 239000003973 paint Substances 0.000 claims description 46
- 229920001577 copolymer Polymers 0.000 claims description 38
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 claims description 35
- 229940112669 cuprous oxide Drugs 0.000 claims description 35
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 claims description 35
- 230000003373 anti-fouling effect Effects 0.000 claims description 27
- -1 acrylic compound Chemical class 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 9
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 8
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 8
- 239000002519 antifouling agent Substances 0.000 claims description 7
- 239000000178 monomer Substances 0.000 claims description 7
- 150000002894 organic compounds Chemical class 0.000 claims description 7
- SBXWFLISHPUINY-UHFFFAOYSA-N triphenyltin Chemical compound C1=CC=CC=C1[Sn](C=1C=CC=CC=1)C1=CC=CC=C1 SBXWFLISHPUINY-UHFFFAOYSA-N 0.000 claims description 7
- 229920002554 vinyl polymer Polymers 0.000 claims description 7
- 229920000642 polymer Polymers 0.000 claims description 6
- 230000007547 defect Effects 0.000 claims description 5
- 125000000524 functional group Chemical group 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002484 inorganic compounds Chemical class 0.000 claims description 4
- YYNNRJWNBXEQTP-UHFFFAOYSA-N 2-[(4-bromophenyl)sulfonylamino]-3-phenylpropanoic acid Chemical compound C=1C=C(Br)C=CC=1S(=O)(=O)NC(C(=O)O)CC1=CC=CC=C1 YYNNRJWNBXEQTP-UHFFFAOYSA-N 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- 239000010425 asbestos Substances 0.000 claims description 3
- 239000004927 clay Substances 0.000 claims description 3
- NJVOZLGKTAPUTQ-UHFFFAOYSA-M fentin chloride Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 NJVOZLGKTAPUTQ-UHFFFAOYSA-M 0.000 claims description 3
- BFWMWWXRWVJXSE-UHFFFAOYSA-M fentin hydroxide Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(O)C1=CC=CC=C1 BFWMWWXRWVJXSE-UHFFFAOYSA-M 0.000 claims description 3
- 229910052602 gypsum Inorganic materials 0.000 claims description 3
- 239000010440 gypsum Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000010445 mica Substances 0.000 claims description 3
- 229910052618 mica group Inorganic materials 0.000 claims description 3
- 239000000049 pigment Substances 0.000 claims description 3
- 229910052895 riebeckite Inorganic materials 0.000 claims description 3
- 150000003606 tin compounds Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052570 clay Inorganic materials 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- WDQNIWFZKXZFAY-UHFFFAOYSA-M fentin acetate Chemical compound CC([O-])=O.C1=CC=CC=C1[Sn+](C=1C=CC=CC=1)C1=CC=CC=C1 WDQNIWFZKXZFAY-UHFFFAOYSA-M 0.000 claims description 2
- 239000004009 herbicide Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000002917 insecticide Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 239000008199 coating composition Substances 0.000 claims 4
- 230000000844 anti-bacterial effect Effects 0.000 claims 2
- 239000003899 bactericide agent Substances 0.000 claims 2
- 230000002363 herbicidal effect Effects 0.000 claims 1
- 239000001023 inorganic pigment Substances 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 29
- 239000008096 xylene Substances 0.000 description 29
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 16
- LPUCKLOWOWADAC-UHFFFAOYSA-M tributylstannyl 2-methylprop-2-enoate Chemical compound CCCC[Sn](CCCC)(CCCC)OC(=O)C(C)=C LPUCKLOWOWADAC-UHFFFAOYSA-M 0.000 description 13
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 12
- 238000000576 coating method Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 229940049920 malate Drugs 0.000 description 6
- BJEPYKJPYRNKOW-UHFFFAOYSA-L malate(2-) Chemical compound [O-]C(=O)C(O)CC([O-])=O BJEPYKJPYRNKOW-UHFFFAOYSA-L 0.000 description 6
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 6
- YSUXTNDMKYYZPR-UHFFFAOYSA-M tributylstannyl prop-2-enoate Chemical compound CCCC[Sn](CCCC)(CCCC)OC(=O)C=C YSUXTNDMKYYZPR-UHFFFAOYSA-M 0.000 description 6
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 5
- JNRFAGAIHOKUES-UHFFFAOYSA-M triphenylstannyl 2-methylprop-2-enoate Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(OC(=O)C(=C)C)C1=CC=CC=C1 JNRFAGAIHOKUES-UHFFFAOYSA-M 0.000 description 5
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229940018560 citraconate Drugs 0.000 description 4
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- HNEGQIOMVPPMNR-NSCUHMNNSA-L mesaconate(2-) Chemical compound [O-]C(=O)C(/C)=C/C([O-])=O HNEGQIOMVPPMNR-NSCUHMNNSA-L 0.000 description 4
- NHBSOSDSJTVJQC-UHFFFAOYSA-M tricyclohexylstannyl 2-methylprop-2-enoate Chemical compound CC(=C)C([O-])=O.C1CCCCC1[Sn+](C1CCCCC1)C1CCCCC1 NHBSOSDSJTVJQC-UHFFFAOYSA-M 0.000 description 4
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229940065472 octyl acrylate Drugs 0.000 description 3
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 3
- ZBOZYQUPHVWBCE-UHFFFAOYSA-M prop-2-enoate;triphenylstannanylium Chemical compound [O-]C(=O)C=C.C1=CC=CC=C1[Sn+](C=1C=CC=CC=1)C1=CC=CC=C1 ZBOZYQUPHVWBCE-UHFFFAOYSA-M 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- REDSKZBUUUQMSK-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC.CCCC[Sn](CCCC)CCCC REDSKZBUUUQMSK-UHFFFAOYSA-N 0.000 description 3
- RNVJQUPAEIQUTC-UHFFFAOYSA-N tricyclohexyltin Chemical compound C1CCCCC1[Sn](C1CCCCC1)C1CCCCC1 RNVJQUPAEIQUTC-UHFFFAOYSA-N 0.000 description 3
- NAOJTQGBUVHQLM-UHFFFAOYSA-M triethylstannyl 2-methylprop-2-enoate Chemical compound CC[Sn](CC)(CC)OC(=O)C(C)=C NAOJTQGBUVHQLM-UHFFFAOYSA-M 0.000 description 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- LAYAKLSFVAPMEL-UHFFFAOYSA-N 1-ethenoxydodecane Chemical compound CCCCCCCCCCCCOC=C LAYAKLSFVAPMEL-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
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 241000270722 Crocodylidae Species 0.000 description 2
- GXUARMXARIJAFV-UHFFFAOYSA-L barium oxalate Chemical compound [Ba+2].[O-]C(=O)C([O-])=O GXUARMXARIJAFV-UHFFFAOYSA-L 0.000 description 2
- 229940094800 barium oxalate Drugs 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- HVYQSISIEKRMMS-UHFFFAOYSA-M prop-2-enoate;tri(propan-2-yl)stannanylium Chemical compound [O-]C(=O)C=C.CC(C)[Sn+](C(C)C)C(C)C HVYQSISIEKRMMS-UHFFFAOYSA-M 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000003746 surface roughness Effects 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- DFNPRTKVCGZMMC-UHFFFAOYSA-M tributyl(fluoro)stannane Chemical compound CCCC[Sn](F)(CCCC)CCCC DFNPRTKVCGZMMC-UHFFFAOYSA-M 0.000 description 2
- HCQQYCNWRJJRQV-UHFFFAOYSA-M triphenylstannyl n,n-dimethylcarbamodithioate Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(SC(=S)N(C)C)C1=CC=CC=C1 HCQQYCNWRJJRQV-UHFFFAOYSA-M 0.000 description 2
- GSJBKPNSLRKRNR-UHFFFAOYSA-N $l^{2}-stannanylidenetin Chemical compound [Sn].[Sn] GSJBKPNSLRKRNR-UHFFFAOYSA-N 0.000 description 1
- KRYSZTURCOERLC-YRSJTSKRSA-L (e)-but-2-enedioate;tricyclohexylstannanylium Chemical compound [O-]C(=O)\C=C\C([O-])=O.C1CCCCC1[Sn+](C1CCCCC1)C1CCCCC1.C1CCCCC1[Sn+](C1CCCCC1)C1CCCCC1 KRYSZTURCOERLC-YRSJTSKRSA-L 0.000 description 1
- IOMRUDPZPOVCQZ-YRSJTSKRSA-L (e)-but-2-enedioate;triphenylstannanylium Chemical compound [O-]C(=O)\C=C\C([O-])=O.C1=CC=CC=C1[Sn+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[Sn+](C=1C=CC=CC=1)C1=CC=CC=C1 IOMRUDPZPOVCQZ-YRSJTSKRSA-L 0.000 description 1
- YABTYYUIWFCMDW-DYNMZUSMSA-L (z)-but-2-enedioate;tributylstannanylium Chemical compound CCCC[Sn](CCCC)(CCCC)OC(=O)\C=C/C(=O)O[Sn](CCCC)(CCCC)CCCC YABTYYUIWFCMDW-DYNMZUSMSA-L 0.000 description 1
- AKUSHEMSFTWIFN-JRKBNQMXSA-L (z)-but-2-enedioate;trioctylstannanylium Chemical compound [O-]C(=O)\C=C/C([O-])=O.CCCCCCCC[Sn+](CCCCCCCC)CCCCCCCC.CCCCCCCC[Sn+](CCCCCCCC)CCCCCCCC AKUSHEMSFTWIFN-JRKBNQMXSA-L 0.000 description 1
- IOMRUDPZPOVCQZ-JRKBNQMXSA-L (z)-but-2-enedioate;triphenylstannanylium Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(C=1C=CC=CC=1)OC(=O)\C=C/C(=O)O[Sn](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 IOMRUDPZPOVCQZ-JRKBNQMXSA-L 0.000 description 1
- XXCVIFJHBFNFBO-UHFFFAOYSA-N 1-ethenoxyoctane Chemical compound CCCCCCCCOC=C XXCVIFJHBFNFBO-UHFFFAOYSA-N 0.000 description 1
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
- HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 description 1
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-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
- PEDDJMRGCXIRLP-UHFFFAOYSA-K 2-methylprop-2-enoate undecan-6-yltin(3+) Chemical compound C(C(=C)C)(=O)[O-].C(CCCC)C(CCCCC)[Sn+3].C(C(=C)C)(=O)[O-].C(C(=C)C)(=O)[O-] PEDDJMRGCXIRLP-UHFFFAOYSA-K 0.000 description 1
- CJPYOCBPEJUDHN-UHFFFAOYSA-M 2-methylprop-2-enoate;tri(butan-2-yl)stannanylium Chemical compound CC(=C)C([O-])=O.CCC(C)[Sn+](C(C)CC)C(C)CC CJPYOCBPEJUDHN-UHFFFAOYSA-M 0.000 description 1
- WBTDIUKRHWGZOB-UHFFFAOYSA-M 2-methylprop-2-enoate;tri(propan-2-yl)stannanylium Chemical compound CC(=C)C([O-])=O.CC(C)[Sn+](C(C)C)C(C)C WBTDIUKRHWGZOB-UHFFFAOYSA-M 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- SULJDUUNIKTXPP-UHFFFAOYSA-K C(C=C)(=O)[O-].C(CCCC)C(CCCCC)[Sn+3].C(C=C)(=O)[O-].C(C=C)(=O)[O-] Chemical compound C(C=C)(=O)[O-].C(CCCC)C(CCCCC)[Sn+3].C(C=C)(=O)[O-].C(C=C)(=O)[O-] SULJDUUNIKTXPP-UHFFFAOYSA-K 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- KPPOOEFMURTGLE-UHFFFAOYSA-M [diethyl(phenyl)stannyl] 2-methylprop-2-enoate Chemical compound CC(=C)C([O-])=O.CC[Sn+](CC)C1=CC=CC=C1 KPPOOEFMURTGLE-UHFFFAOYSA-M 0.000 description 1
- TTYZFWSAJBXSNR-UHFFFAOYSA-M [diethyl(phenyl)stannyl] prop-2-enoate Chemical compound [O-]C(=O)C=C.CC[Sn+](CC)C1=CC=CC=C1 TTYZFWSAJBXSNR-UHFFFAOYSA-M 0.000 description 1
- KCGZMLQJOMHJHT-UHFFFAOYSA-M [ethyl(diphenyl)stannyl] 2-methylprop-2-enoate Chemical compound CC(=C)C([O-])=O.C=1C=CC=CC=1[Sn+](CC)C1=CC=CC=C1 KCGZMLQJOMHJHT-UHFFFAOYSA-M 0.000 description 1
- HLAZNURWCVDYBK-UHFFFAOYSA-M [octyl(diphenyl)stannyl] 2-methylprop-2-enoate Chemical compound CC(=C)C([O-])=O.C=1C=CC=CC=1[Sn+](CCCCCCCC)C1=CC=CC=C1 HLAZNURWCVDYBK-UHFFFAOYSA-M 0.000 description 1
- VUWGQWXLBXWDMB-UHFFFAOYSA-M [octyl(diphenyl)stannyl] prop-2-enoate Chemical compound [O-]C(=O)C=C.C=1C=CC=CC=1[Sn+](CCCCCCCC)C1=CC=CC=C1 VUWGQWXLBXWDMB-UHFFFAOYSA-M 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- YABTYYUIWFCMDW-SRTAMGJPSA-L bis(tributylstannyl) (e)-but-2-enedioate Chemical compound CCCC[Sn](CCCC)(CCCC)OC(=O)\C=C\C(=O)O[Sn](CCCC)(CCCC)CCCC YABTYYUIWFCMDW-SRTAMGJPSA-L 0.000 description 1
- ZGDZLFHJZBHIQP-UHFFFAOYSA-M butyl(diethyl)stannanylium;2-methylprop-2-enoate Chemical compound CC(=C)C([O-])=O.CCCC[Sn+](CC)CC ZGDZLFHJZBHIQP-UHFFFAOYSA-M 0.000 description 1
- BVLLUWMXDLDEGF-UHFFFAOYSA-M butyl-pentyl-propylstannanylium;2-methylprop-2-enoate Chemical compound CC(=C)C([O-])=O.CCCCC[Sn+](CCC)CCCC BVLLUWMXDLDEGF-UHFFFAOYSA-M 0.000 description 1
- HESQNFGBFRACIQ-UHFFFAOYSA-M butyl-pentyl-propylstannanylium;prop-2-enoate Chemical compound [O-]C(=O)C=C.CCCCC[Sn+](CCC)CCCC HESQNFGBFRACIQ-UHFFFAOYSA-M 0.000 description 1
- DGQLVPJVXFOQEV-JNVSTXMASA-N carminic acid Chemical compound OC1=C2C(=O)C=3C(C)=C(C(O)=O)C(O)=CC=3C(=O)C2=C(O)C(O)=C1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O DGQLVPJVXFOQEV-JNVSTXMASA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000001351 cycling effect Effects 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
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 1
- LNNWVNGFPYWNQE-GMIGKAJZSA-N desomorphine Chemical compound C1C2=CC=C(O)C3=C2[C@]24CCN(C)[C@H]1[C@@H]2CCC[C@@H]4O3 LNNWVNGFPYWNQE-GMIGKAJZSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- QWOHFDVDQIFZLE-UHFFFAOYSA-M diethyl(hexyl)stannanylium;2-methylprop-2-enoate Chemical compound CC(=C)C([O-])=O.CCCCCC[Sn+](CC)CC QWOHFDVDQIFZLE-UHFFFAOYSA-M 0.000 description 1
- PZXXXEYLODTTOT-UHFFFAOYSA-M diethyl(hexyl)stannanylium;prop-2-enoate Chemical compound [O-]C(=O)C=C.CCCCCC[Sn+](CC)CC PZXXXEYLODTTOT-UHFFFAOYSA-M 0.000 description 1
- XBHUUSPJSWENEC-UHFFFAOYSA-M diethyl(octyl)stannanylium;2-methylprop-2-enoate Chemical compound CC(=C)C([O-])=O.CCCCCCCC[Sn+](CC)CC XBHUUSPJSWENEC-UHFFFAOYSA-M 0.000 description 1
- JLUTTWWADVPOCF-UHFFFAOYSA-M diethyl(octyl)stannanylium;prop-2-enoate Chemical compound [O-]C(=O)C=C.CCCCCCCC[Sn+](CC)CC JLUTTWWADVPOCF-UHFFFAOYSA-M 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- VOEYXMAFNDNNED-UHFFFAOYSA-N metolcarb Chemical compound CNC(=O)OC1=CC=CC(C)=C1 VOEYXMAFNDNNED-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- UNMGLSGVXHBBPH-BVHINDLDSA-L nickel(2+) (NE)-N-[(3E)-3-oxidoiminobutan-2-ylidene]hydroxylamine Chemical compound [Ni++].C\C(=N/O)\C(\C)=N\[O-].C\C(=N/O)\C(\C)=N\[O-] UNMGLSGVXHBBPH-BVHINDLDSA-L 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
- 238000010422 painting Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
- RBADKZSHVBXOHI-UHFFFAOYSA-M prop-2-enoate;tri(butan-2-yl)stannanylium Chemical compound [O-]C(=O)C=C.CCC(C)[Sn+](C(C)CC)C(C)CC RBADKZSHVBXOHI-UHFFFAOYSA-M 0.000 description 1
- FXMURJDJENHQHM-UHFFFAOYSA-M prop-2-enoate;tripropylstannanylium Chemical compound [O-]C(=O)C=C.CCC[Sn+](CCC)CCC FXMURJDJENHQHM-UHFFFAOYSA-M 0.000 description 1
- KMQUXWFJALYLAL-UHFFFAOYSA-N pyridine-3-carboxylic acid;triphenyltin Chemical compound OC(=O)C1=CC=CN=C1.C1=CC=CC=C1[Sn](C=1C=CC=CC=1)C1=CC=CC=C1 KMQUXWFJALYLAL-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007665 sagging Methods 0.000 description 1
- KKKDGYXNGYJJRX-UHFFFAOYSA-M silver nitrite Chemical compound [Ag+].[O-]N=O KKKDGYXNGYJJRX-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000001017 thiazole dye Substances 0.000 description 1
- YJGJRYWNNHUESM-UHFFFAOYSA-J triacetyloxystannyl acetate Chemical compound [Sn+4].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O YJGJRYWNNHUESM-UHFFFAOYSA-J 0.000 description 1
- NLTRLQSEZRUEGY-UHFFFAOYSA-M triethylstannyl prop-2-enoate Chemical compound [O-]C(=O)C=C.CC[Sn+](CC)CC NLTRLQSEZRUEGY-UHFFFAOYSA-M 0.000 description 1
- XMHKTINRBAKEDS-UHFFFAOYSA-N trioctyltin Chemical compound CCCCCCCC[Sn](CCCCCCCC)CCCCCCCC XMHKTINRBAKEDS-UHFFFAOYSA-N 0.000 description 1
- MUHFQLVFMFDJOK-UHFFFAOYSA-N triphenyl(triphenylstannyloxy)stannane Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(C=1C=CC=CC=1)O[Sn](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 MUHFQLVFMFDJOK-UHFFFAOYSA-N 0.000 description 1
- GFHQVPZQABAPQR-UHFFFAOYSA-M tripropylstannyl 2-methylprop-2-enoate Chemical compound CCC[Sn](CCC)(CCC)OC(=O)C(C)=C GFHQVPZQABAPQR-UHFFFAOYSA-M 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/16—Antifouling paints; Underwater paints
- C09D5/1606—Antifouling paints; Underwater paints characterised by the anti-fouling agent
- C09D5/1637—Macromolecular compounds
- C09D5/1643—Macromolecular compounds containing tin
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Road Signs Or Road Markings (AREA)
- Hydrogenated Pyridines (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55124661A JPS5749675A (en) | 1980-09-10 | 1980-09-10 | Anti-fouling paint composition |
| NO812903A NO812903L (no) | 1980-09-10 | 1981-08-26 | Begroningshindrende maling. |
| GB8126134A GB2084167B (en) | 1980-09-10 | 1981-08-27 | Antifouling paint compositions |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55124661A JPS5749675A (en) | 1980-09-10 | 1980-09-10 | Anti-fouling paint composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5749675A JPS5749675A (en) | 1982-03-23 |
| JPS6333513B2 true JPS6333513B2 (de) | 1988-07-05 |
Family
ID=14890916
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP55124661A Granted JPS5749675A (en) | 1980-09-10 | 1980-09-10 | Anti-fouling paint composition |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS5749675A (de) |
| GB (1) | GB2084167B (de) |
| NO (1) | NO812903L (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0485516U (de) * | 1990-11-29 | 1992-07-24 |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS594662A (ja) * | 1982-06-30 | 1984-01-11 | Nitto Kasei Kk | 光重合性水中防汚組成物 |
| GB8414675D0 (en) * | 1984-06-08 | 1984-07-11 | Int Paint Plc | Marine antifouling paint |
| JPH06102870B2 (ja) * | 1987-06-16 | 1994-12-14 | 竹本油脂株式会社 | 炭素繊維用サイジング剤 |
| JP2830051B2 (ja) * | 1989-05-18 | 1998-12-02 | 東レ株式会社 | 炭素繊維強化金属複合材料用プリフォームの製造方法 |
| US5427793A (en) * | 1993-04-21 | 1995-06-27 | Minnesota Mining And Manufacturing Company | Tin-acrylate-containing polymers as algicidal agents in building materials |
| WO2000077103A1 (en) * | 1999-06-11 | 2000-12-21 | J.C. Hempel's Skibsfarve-Fabrik A/S | Self-polishing marine antifouling paint composition containing blocked acid functional co-polymers and fibres |
| EP1208167B1 (de) * | 1999-06-11 | 2003-07-30 | J.C. Hempel's Skibsfarve-Fabrik A/S | Selbstpolierende anwuchsverhindernde anstrichfarbe für wasserfahrzeuge - mit silizium enthaltendedn copolymeren und fasern |
| FR2909676B1 (fr) * | 2006-12-11 | 2009-03-20 | Astrium Sas Soc Par Actions Si | Procede pour ameliorer l'adherence de fibres de carbone vis-a-vis d'une matrice organique |
| JP4887323B2 (ja) | 2007-05-22 | 2012-02-29 | 三洋化成工業株式会社 | 繊維用集束剤 |
| JP7368938B2 (ja) * | 2017-12-22 | 2023-10-25 | 関西ペイント株式会社 | 防食性に優れた水性塗料組成物 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4860725A (de) * | 1971-12-02 | 1973-08-25 | ||
| JPS5463136A (en) * | 1977-10-31 | 1979-05-21 | Dainippon Toryo Co Ltd | Antifouling coating composition |
| JPS5575407A (en) * | 1978-12-04 | 1980-06-06 | Kansai Paint Co Ltd | Preparation of high molecular organotin compound |
| JPS5649765A (en) * | 1979-09-25 | 1981-05-06 | Sankyo Yuki Gosei Kk | Antifouling paint |
-
1980
- 1980-09-10 JP JP55124661A patent/JPS5749675A/ja active Granted
-
1981
- 1981-08-26 NO NO812903A patent/NO812903L/no unknown
- 1981-08-27 GB GB8126134A patent/GB2084167B/en not_active Expired
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4860725A (de) * | 1971-12-02 | 1973-08-25 | ||
| JPS5463136A (en) * | 1977-10-31 | 1979-05-21 | Dainippon Toryo Co Ltd | Antifouling coating composition |
| JPS5575407A (en) * | 1978-12-04 | 1980-06-06 | Kansai Paint Co Ltd | Preparation of high molecular organotin compound |
| JPS5649765A (en) * | 1979-09-25 | 1981-05-06 | Sankyo Yuki Gosei Kk | Antifouling paint |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0485516U (de) * | 1990-11-29 | 1992-07-24 |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2084167B (en) | 1984-12-19 |
| GB2084167A (en) | 1982-04-07 |
| JPS5749675A (en) | 1982-03-23 |
| NO812903L (no) | 1982-03-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69402799T2 (de) | Anwuchsverhindernde Überzugszusammensetzung | |
| EP0297505B1 (de) | Anwuchsverhindernde Anstrichfarbe | |
| US9045650B2 (en) | Polymer with salt groups and antifouling coating composition comprising said polymer | |
| US4426464A (en) | Marine paint | |
| JP3474672B2 (ja) | 塗料組成物 | |
| PT1457531E (pt) | Composição de tinta anti-incrustação, películas de tinta anti-incrustação e navios, estruturas submarinas, equipamento de pesca e redes de pesca recobertas com as películas | |
| US4485197A (en) | Resinous composition and antifouling paint | |
| JPS6157350B2 (de) | ||
| JPS6333513B2 (de) | ||
| CN1263810C (zh) | 防污涂料 | |
| JP3451786B2 (ja) | 塗料組成物 | |
| US4098971A (en) | Organotin polymers and antifouling paints containing same | |
| JPS60184513A (ja) | グラフト重合体の製造方法 | |
| EP0091039B1 (de) | Antifoulingmittel | |
| GB1598455A (en) | Formulation and manufacture of antifouling compositions | |
| JPS632311B2 (de) | ||
| JPH08277372A (ja) | 塗料組成物 | |
| EP0218573B1 (de) | Bewuchsverhindernde Anstrichmassen | |
| JPS6114267A (ja) | 撥水撥油性塗料 | |
| JPH0524187B2 (de) | ||
| NO154968B (no) | Begroningshindrende belegg. | |
| US5472993A (en) | Anti-fouling paint | |
| US4939219A (en) | Coating compositions for preventing adhesion of aquatic organisms | |
| JPS6241630B2 (de) | ||
| JPH042632B2 (de) |