JPH0119432B2 - - Google Patents

Info

Publication number: JPH0119432B2
Authority: JP; Japan
Prior art keywords: antifouling; ester; parts; resin; antifouling paint
Prior art date: 1982-04-20
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

Application number

JP6465882A

Other languages

English (en)

Japanese (ja)

Other versions

JPS58183761A (ja

Inventor

Koji Kawase

Takeo Shiba

Eiichi Yamada

Toshiro Matsuo

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

NOF Corp

Original Assignee

Nippon Oil and Fats Co Ltd

Priority date (The priority date 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 date listed.)

1982-04-20

Filing date

1982-04-20

Publication date

1989-04-11

1982-04-20 Application filed by Nippon Oil and Fats Co Ltd filed Critical Nippon Oil and Fats Co Ltd

1982-04-20 Priority to JP6465882A priority Critical patent/JPS58183761A/ja

1983-10-27 Publication of JPS58183761A publication Critical patent/JPS58183761A/ja

1989-04-11 Publication of JPH0119432B2 publication Critical patent/JPH0119432B2/ja

Status Granted legal-status Critical Current

Links

230000003373 anti-fouling effect Effects 0.000 claims description 36
239000003973 paint Substances 0.000 claims description 30
229920001577 copolymer Polymers 0.000 claims description 16
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 12
150000002148 esters Chemical class 0.000 claims description 11
150000001875 compounds Chemical class 0.000 claims description 8
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 7
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 6
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 6
150000007519 polyprotic acids Polymers 0.000 claims description 5
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
239000011976 maleic acid Substances 0.000 claims description 4
125000002947 alkylene group Chemical group 0.000 claims description 3
LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical group COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 claims description 2
125000005156 substituted alkylene group Chemical group 0.000 claims description 2
-1 ester compound Chemical class 0.000 description 29
239000011347 resin Substances 0.000 description 23
229920005989 resin Polymers 0.000 description 23
239000011159 matrix material Substances 0.000 description 16
239000000243 solution Substances 0.000 description 13
239000002519 antifouling agent Substances 0.000 description 12
230000000052 comparative effect Effects 0.000 description 12
229920000642 polymer Polymers 0.000 description 11
239000013535 sea water Substances 0.000 description 10
238000012360 testing method Methods 0.000 description 10
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
239000011248 coating agent Substances 0.000 description 9
238000000576 coating method Methods 0.000 description 9
238000004090 dissolution Methods 0.000 description 9
239000000203 mixture Substances 0.000 description 9
239000008096 xylene Substances 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
238000010828 elution Methods 0.000 description 8
238000000034 method Methods 0.000 description 7
238000003756 stirring Methods 0.000 description 7
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 6
YSEKNCXYRGKTBJ-UHFFFAOYSA-N dimethyl 2-hydroxybutanedioate Chemical compound COC(=O)CC(O)C(=O)OC YSEKNCXYRGKTBJ-UHFFFAOYSA-N 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 6
238000011056 performance test Methods 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
238000010992 reflux Methods 0.000 description 5
125000005907 alkyl ester group Chemical group 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
238000007654 immersion Methods 0.000 description 4
238000005259 measurement Methods 0.000 description 4
239000000178 monomer Substances 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
238000007664 blowing Methods 0.000 description 3
229910052802 copper Inorganic materials 0.000 description 3
239000010949 copper Substances 0.000 description 3
125000004185 ester group Chemical group 0.000 description 3
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
239000011259 mixed solution Substances 0.000 description 3
238000002156 mixing Methods 0.000 description 3
238000003860 storage Methods 0.000 description 3
150000003606 tin compounds Chemical class 0.000 description 3
KDGNCLDCOVTOCS-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy propan-2-yl carbonate Chemical compound CC(C)OC(=O)OOC(C)(C)C KDGNCLDCOVTOCS-UHFFFAOYSA-N 0.000 description 2
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
239000004342 Benzoyl peroxide Substances 0.000 description 2
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
239000005749 Copper compound Substances 0.000 description 2
KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 2
239000002174 Styrene-butadiene Substances 0.000 description 2
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
238000005452 bending Methods 0.000 description 2
235000019400 benzoyl peroxide Nutrition 0.000 description 2
230000007227 biological adhesion Effects 0.000 description 2
MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
150000001880 copper compounds Chemical class 0.000 description 2
230000007423 decrease Effects 0.000 description 2
IEPRKVQEAMIZSS-AATRIKPKSA-N diethyl fumarate Chemical compound CCOC(=O)\C=C\C(=O)OCC IEPRKVQEAMIZSS-AATRIKPKSA-N 0.000 description 2
229920001971 elastomer Polymers 0.000 description 2
239000001530 fumaric acid Substances 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
230000036314 physical performance Effects 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
239000005060 rubber Substances 0.000 description 2
239000011115 styrene butadiene Substances 0.000 description 2
229920003048 styrene butadiene rubber Polymers 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 2
239000002966 varnish Substances 0.000 description 2
NIDNOXCRFUCAKQ-UMRXKNAASA-N (1s,2r,3s,4r)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid Chemical group C1[C@H]2C=C[C@@H]1[C@H](C(=O)O)[C@@H]2C(O)=O NIDNOXCRFUCAKQ-UMRXKNAASA-N 0.000 description 1
XVOUMQNXTGKGMA-OWOJBTEDSA-N (E)-glutaconic acid Chemical compound OC(=O)C\C=C\C(O)=O XVOUMQNXTGKGMA-OWOJBTEDSA-N 0.000 description 1
239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 description 1
AYAUWVRAUCDBFR-ONEGZZNKSA-N (e)-4-oxo-4-propoxybut-2-enoic acid Chemical compound CCCOC(=O)\C=C\C(O)=O AYAUWVRAUCDBFR-ONEGZZNKSA-N 0.000 description 1
YKTNISGZEGZHIS-UHFFFAOYSA-N 2-$l^{1}-oxidanyloxy-2-methylpropane Chemical group CC(C)(C)O[O] YKTNISGZEGZHIS-UHFFFAOYSA-N 0.000 description 1
JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
PSZAEHPBBUYICS-UHFFFAOYSA-N 2-methylidenepropanedioic acid Chemical compound OC(=O)C(=C)C(O)=O PSZAEHPBBUYICS-UHFFFAOYSA-N 0.000 description 1
AHWAAQOJHMFNIV-UHFFFAOYSA-N 2-tert-butylperoxy-2-ethylhexanoic acid Chemical compound CCCCC(CC)(C(O)=O)OOC(C)(C)C AHWAAQOJHMFNIV-UHFFFAOYSA-N 0.000 description 1
GQZXRLWUYONVCP-UHFFFAOYSA-N 3-[1-(dimethylamino)ethyl]phenol Chemical compound CN(C)C(C)C1=CC=CC(O)=C1 GQZXRLWUYONVCP-UHFFFAOYSA-N 0.000 description 1
JDOZUYVDIAKODH-SNAWJCMRSA-N 4-o-ethyl 1-o-methyl (e)-but-2-enedioate Chemical compound CCOC(=O)\C=C\C(=O)OC JDOZUYVDIAKODH-SNAWJCMRSA-N 0.000 description 1
JDOZUYVDIAKODH-PLNGDYQASA-N 4-o-ethyl 1-o-methyl (z)-but-2-enedioate Chemical compound CCOC(=O)\C=C/C(=O)OC JDOZUYVDIAKODH-PLNGDYQASA-N 0.000 description 1
239000004925 Acrylic resin Substances 0.000 description 1
229920000178 Acrylic resin Polymers 0.000 description 1
241000251468 Actinopterygii Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
241000238586 Cirripedia Species 0.000 description 1
IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 1
IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
241000237502 Ostreidae Species 0.000 description 1
241000237503 Pectinidae Species 0.000 description 1
241000206607 Porphyra umbilicalis Species 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
241000251555 Tunicata Species 0.000 description 1
241000196251 Ulva arasakii Species 0.000 description 1
238000005299 abrasion Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229940091181 aconitic acid Drugs 0.000 description 1
239000000654 additive Substances 0.000 description 1
125000003158 alcohol group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
NJYYHBHYDNPAJM-UHFFFAOYSA-N bis(2-methoxyethyl) 2-methylidenebutanedioate Chemical compound COCCOC(=O)CC(=C)C(=O)OCCOC NJYYHBHYDNPAJM-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
GTZCVFVGUGFEME-IWQZZHSRSA-N cis-aconitic acid Chemical compound OC(=O)C\C(C(O)=O)=C\C(O)=O GTZCVFVGUGFEME-IWQZZHSRSA-N 0.000 description 1
HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
229940018557 citraconic acid Drugs 0.000 description 1
BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 1
229940112669 cuprous oxide Drugs 0.000 description 1
IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
VYXGXXYXSAMWBM-ONEGZZNKSA-N dimethyl (e)-2-chlorobut-2-enedioate Chemical compound COC(=O)\C=C(\Cl)C(=O)OC VYXGXXYXSAMWBM-ONEGZZNKSA-N 0.000 description 1
LDCRTTXIJACKKU-ONEGZZNKSA-N dimethyl fumarate Chemical compound COC(=O)\C=C\C(=O)OC LDCRTTXIJACKKU-ONEGZZNKSA-N 0.000 description 1
229960004419 dimethyl fumarate Drugs 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000004945 emulsification Methods 0.000 description 1
238000010556 emulsion polymerization method Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000010528 free radical solution polymerization reaction Methods 0.000 description 1
239000000446 fuel Substances 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
238000001879 gelation Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000012690 ionic polymerization Methods 0.000 description 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007788 liquid Substances 0.000 description 1
230000007774 longterm Effects 0.000 description 1
229940049920 malate Drugs 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
235000020636 oyster Nutrition 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000002685 polymerization catalyst Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
238000010526 radical polymerization reaction Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
235000020637 scallop Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical class CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical class CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 1
SBXWFLISHPUINY-UHFFFAOYSA-N triphenyltin Chemical class C1=CC=CC=C1[Sn](C=1C=CC=CC=1)C1=CC=CC=C1 SBXWFLISHPUINY-UHFFFAOYSA-N 0.000 description 1

Landscapes

Paints Or Removers (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

JP6465882A 1982-04-20 1982-04-20 防汚塗料 Granted JPS58183761A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP6465882A JPS58183761A (ja)	1982-04-20	1982-04-20	防汚塗料

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP6465882A JPS58183761A (ja)	1982-04-20	1982-04-20	防汚塗料

Publications (2)

Publication Number	Publication Date
JPS58183761A JPS58183761A (ja)	1983-10-27
JPH0119432B2 true JPH0119432B2 (fr)	1989-04-11

Family

ID=13264534

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP6465882A Granted JPS58183761A (ja)	1982-04-20	1982-04-20	防汚塗料

Country Status (1)

Country	Link
JP (1)	JPS58183761A (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6149778A (ja) *	1984-08-20	1986-03-11	Hitachi Zosen Corp	自動溶接方法
JPS6186445U (fr) *	1984-11-14	1986-06-06
CN109054608B (zh) *	2018-06-15	2021-03-19	苏州益可泰电子材料有限公司	金属材料及其制备方法
CN109054635B (zh) *	2018-06-15	2021-03-19	苏州益可泰电子材料有限公司	高分子材料及其制备方法

1982
- 1982-04-20 JP JP6465882A patent/JPS58183761A/ja active Granted

Also Published As

Publication number	Publication date
JPS58183761A (ja)	1983-10-27

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US5439512A (en)	1995-08-08	Resin composition and antifouling paint
JPS5919593B2 (ja)	1984-05-07	防汚塗料
KR102528764B1 (ko)	2023-05-08	방오 도료 조성물
KR20140117922A (ko)	2014-10-08	방오도료용 공중합체 바인더, 그 제조방법 및 이를 포함한 방오도료 조성물
JPH0524187B2 (fr)	1993-04-07
JPH0119431B2 (fr)	1989-04-11
JPS638996B2 (fr)	1988-02-25
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JPH0119429B2 (fr)	1989-04-11
JPH042632B2 (fr)	1992-01-20
KR100520794B1 (ko)	2006-02-28	방오도료 조성물