TWI290148B - Acrylic resin and antifouling coating - Google Patents
Acrylic resin and antifouling coating Download PDFInfo
- Publication number
- TWI290148B TWI290148B TW091137244A TW91137244A TWI290148B TW I290148 B TWI290148 B TW I290148B TW 091137244 A TW091137244 A TW 091137244A TW 91137244 A TW91137244 A TW 91137244A TW I290148 B TWI290148 B TW I290148B
- Authority
- TW
- Taiwan
- Prior art keywords
- acid
- acrylic resin
- parts
- resin
- meth
- Prior art date
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- 238000000576 coating method Methods 0.000 title claims abstract description 65
- 239000004925 Acrylic resin Substances 0.000 title claims abstract description 64
- 239000011248 coating agent Substances 0.000 title claims abstract description 62
- 229920000178 Acrylic resin Polymers 0.000 title claims abstract description 61
- 230000003373 anti-fouling effect Effects 0.000 title claims abstract description 58
- 150000007524 organic acids Chemical group 0.000 claims abstract description 18
- 229910052751 metal Inorganic materials 0.000 claims abstract description 14
- 239000002184 metal Substances 0.000 claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- 239000011347 resin Substances 0.000 claims description 56
- 229920005989 resin Polymers 0.000 claims description 56
- -1 cyclic organic acid Chemical class 0.000 claims description 55
- 239000002253 acid Substances 0.000 claims description 52
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 51
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims description 31
- 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 claims description 27
- 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 claims description 27
- 239000000178 monomer Substances 0.000 claims description 23
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 150000002736 metal compounds Chemical class 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 5
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical class CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 claims description 4
- QUUCYKKMFLJLFS-UHFFFAOYSA-N Dehydroabietan Natural products CC1(C)CCCC2(C)C3=CC=C(C(C)C)C=C3CCC21 QUUCYKKMFLJLFS-UHFFFAOYSA-N 0.000 claims description 3
- NFWKVWVWBFBAOV-UHFFFAOYSA-N Dehydroabietic acid Natural products OC(=O)C1(C)CCCC2(C)C3=CC=C(C(C)C)C=C3CCC21 NFWKVWVWBFBAOV-UHFFFAOYSA-N 0.000 claims description 3
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 claims description 3
- NFWKVWVWBFBAOV-MISYRCLQSA-N dehydroabietic acid Chemical compound OC(=O)[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 NFWKVWVWBFBAOV-MISYRCLQSA-N 0.000 claims description 3
- 229940118781 dehydroabietic acid Drugs 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
- 230000007774 longterm Effects 0.000 abstract description 24
- 238000005498 polishing Methods 0.000 abstract description 16
- 150000002430 hydrocarbons Chemical group 0.000 abstract description 11
- 230000007547 defect Effects 0.000 abstract description 5
- 230000001747 exhibiting effect Effects 0.000 abstract description 3
- 229930195733 hydrocarbon Natural products 0.000 abstract description 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 239000002320 enamel (paints) Substances 0.000 description 49
- 238000004519 manufacturing process Methods 0.000 description 41
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 40
- 239000000203 mixture Substances 0.000 description 35
- 210000003298 dental enamel Anatomy 0.000 description 34
- 238000006243 chemical reaction Methods 0.000 description 32
- 239000002519 antifouling agent Substances 0.000 description 25
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 21
- 239000008096 xylene Substances 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- 239000003973 paint Substances 0.000 description 17
- 150000002148 esters Chemical class 0.000 description 13
- 239000002904 solvent Substances 0.000 description 11
- 239000004014 plasticizer Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- 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 8
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 8
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000002966 varnish Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 7
- 229910052712 strontium Inorganic materials 0.000 description 7
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 7
- 239000011230 binding agent Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 239000004922 lacquer Substances 0.000 description 6
- 239000000049 pigment Substances 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 229910052797 bismuth Inorganic materials 0.000 description 4
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- MHVJRKBZMUDEEV-UHFFFAOYSA-N (-)-ent-pimara-8(14),15-dien-19-oic acid Natural products C1CCC(C(O)=O)(C)C2C1(C)C1CCC(C=C)(C)C=C1CC2 MHVJRKBZMUDEEV-UHFFFAOYSA-N 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 3
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 3
- 235000011613 Pinus brutia Nutrition 0.000 description 3
- 241000018646 Pinus brutia Species 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- KWVFUTDPKIKVQW-UHFFFAOYSA-N [Sr].[Na] Chemical compound [Sr].[Na] KWVFUTDPKIKVQW-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 3
- 239000008199 coating composition Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- 239000012188 paraffin wax Substances 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 108090000765 processed proteins & peptides Proteins 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 125000003107 substituted aryl group Chemical group 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
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- MHVJRKBZMUDEEV-APQLOABGSA-N (+)-Pimaric acid Chemical compound [C@H]1([C@](CCC2)(C)C(O)=O)[C@@]2(C)[C@H]2CC[C@](C=C)(C)C=C2CC1 MHVJRKBZMUDEEV-APQLOABGSA-N 0.000 description 2
- NXQMCAOPTPLPRL-UHFFFAOYSA-N 2-(2-benzoyloxyethoxy)ethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCOCCOC(=O)C1=CC=CC=C1 NXQMCAOPTPLPRL-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- PORQOHRXAJJKGK-UHFFFAOYSA-N 4,5-dichloro-2-n-octyl-3(2H)-isothiazolone Chemical compound CCCCCCCCN1SC(Cl)=C(Cl)C1=O PORQOHRXAJJKGK-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- DXVYLFHTJZWTRF-UHFFFAOYSA-N Ethyl isobutyl ketone Chemical compound CCC(=O)CC(C)C DXVYLFHTJZWTRF-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- GJWSUKYXUMVMGX-UHFFFAOYSA-N citronellic acid Chemical compound OC(=O)CC(C)CCC=C(C)C GJWSUKYXUMVMGX-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical compound OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- MXYATHGRPJZBNA-KRFUXDQASA-N isopimaric acid Chemical compound [C@H]1([C@](CCC2)(C)C(O)=O)[C@@]2(C)[C@H]2CC[C@@](C=C)(C)CC2=CC1 MXYATHGRPJZBNA-KRFUXDQASA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- VILGDADBAQFRJE-UHFFFAOYSA-N n,n-bis(1,3-benzothiazol-2-ylsulfanyl)-2-methylpropan-2-amine Chemical compound C1=CC=C2SC(SN(SC=3SC4=CC=CC=C4N=3)C(C)(C)C)=NC2=C1 VILGDADBAQFRJE-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000007665 sagging Methods 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
- 239000004246 zinc acetate Substances 0.000 description 2
- 229940043810 zinc pyrithione Drugs 0.000 description 2
- PICXIOQBANWBIZ-UHFFFAOYSA-N zinc;1-oxidopyridine-2-thione Chemical compound [Zn+2].[O-]N1C=CC=CC1=S.[O-]N1C=CC=CC1=S PICXIOQBANWBIZ-UHFFFAOYSA-N 0.000 description 2
- MFZHYRHWRMLSGC-UHFFFAOYSA-N (4,4,5-trichloro-2-oxo-1,3,2lambda5-dioxaphospholan-2-yl) dihydrogen phosphate Chemical compound OP(O)(=O)OP1(=O)OC(Cl)C(Cl)(Cl)O1 MFZHYRHWRMLSGC-UHFFFAOYSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- GDXHBFHOEYVPED-UHFFFAOYSA-N 1-(2-butoxyethoxy)butane Chemical compound CCCCOCCOCCCC GDXHBFHOEYVPED-UHFFFAOYSA-N 0.000 description 1
- NTINFTOOVNKGIU-UHFFFAOYSA-N 2-(2-hydroxyethoxycarbonyl)benzoic acid Chemical compound OCCOC(=O)C1=CC=CC=C1C(O)=O NTINFTOOVNKGIU-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-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
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- HFCUBKYHMMPGBY-UHFFFAOYSA-N 2-methoxyethyl prop-2-enoate Chemical compound COCCOC(=O)C=C HFCUBKYHMMPGBY-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- ZVPQMESWKIQHGS-UHFFFAOYSA-N 3-(2,3-dichlorophenyl)-1,1-dimethylurea Chemical compound CN(C)C(=O)NC1=CC=CC(Cl)=C1Cl ZVPQMESWKIQHGS-UHFFFAOYSA-N 0.000 description 1
- UZIRFBMYVLTOHJ-UHFFFAOYSA-N 3-(2,4,6-trichlorophenyl)pyrrole-2,5-dione Chemical compound ClC1=CC(Cl)=CC(Cl)=C1C1=CC(=O)NC1=O UZIRFBMYVLTOHJ-UHFFFAOYSA-N 0.000 description 1
- MXYATHGRPJZBNA-UHFFFAOYSA-N 4-epi-isopimaric acid Natural products C1CCC(C(O)=O)(C)C2C1(C)C1CCC(C=C)(C)CC1=CC2 MXYATHGRPJZBNA-UHFFFAOYSA-N 0.000 description 1
- CKNYEUXAXWTAPK-UHFFFAOYSA-N 4-octoxy-4-oxobutanoic acid Chemical compound CCCCCCCCOC(=O)CCC(O)=O CKNYEUXAXWTAPK-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- JNXDCMUUZNIWPQ-UHFFFAOYSA-N trioctyl benzene-1,2,4-tricarboxylate Chemical compound CCCCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCCC)C(C(=O)OCCCCCCCC)=C1 JNXDCMUUZNIWPQ-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 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
-
- 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
- C09D5/1656—Antifouling paints; Underwater paints characterised by the film-forming substance
- C09D5/1662—Synthetic film-forming substance
- C09D5/1668—Vinyl-type polymers
-
- 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
- C08F8/00—Chemical modification by after-treatment
-
- 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
- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
- C08F2800/20—Copolymer characterised by the proportions of the comonomers expressed as weight or mass percentages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Paints Or Removers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001395230 | 2001-12-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200301263A TW200301263A (en) | 2003-07-01 |
| TWI290148B true TWI290148B (en) | 2007-11-21 |
Family
ID=19188947
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW091137244A TWI290148B (en) | 2001-12-26 | 2002-12-25 | Acrylic resin and antifouling coating |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6846878B2 (https=) |
| EP (1) | EP1323745B1 (https=) |
| JP (1) | JP3958681B2 (https=) |
| KR (1) | KR100975322B1 (https=) |
| CN (1) | CN1250586C (https=) |
| AU (1) | AU2002325481B2 (https=) |
| DE (1) | DE60207968T2 (https=) |
| DK (1) | DK1323745T3 (https=) |
| NO (2) | NO328137B1 (https=) |
| SG (1) | SG123546A1 (https=) |
| TW (1) | TWI290148B (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8263684B2 (en) | 2004-05-26 | 2012-09-11 | Nippon Paint Co., Ltd. | Coating composition, coating film, and method of reducing underwater friction |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK1496088T3 (da) * | 2000-03-28 | 2012-01-30 | Nippon Paint Co Ltd | Antifoulingbelægning |
| CN1709925B (zh) * | 2005-04-18 | 2011-10-26 | 中国海洋大学 | 含辣素官能团的丙烯酸锌或铜的树脂及其制备方法和应用 |
| KR100700069B1 (ko) * | 2005-05-23 | 2007-03-28 | (주)체어텍 | 회전되는 등받이가 구비되는 의자 |
| PL2128208T3 (pl) * | 2007-02-27 | 2012-12-31 | Nitto Kasei Co Ltd | Impregnacyjna kompozycja powłokowa, sposób wytwarzania kompozycji, impregnacyjna powłoka powlekająca utworzona z zastosowaniem kompozycji, powleczony powłoką powlekającą przedmiot na jego powierzchni i sposób impregnacyjnego działania dla wytworzenia powłoki powlekającej |
| JPWO2009011332A1 (ja) * | 2007-07-18 | 2010-09-24 | 日本ペイントマリン株式会社 | 防汚塗料組成物、防汚塗膜、ならびに船舶および水中構造物 |
| JP2011026357A (ja) * | 2007-11-21 | 2011-02-10 | Nitto Kasei Co Ltd | 防汚塗料組成物、該組成物の製造方法、該組成物を用いて形成される防汚塗膜、該塗膜を表面に有する塗装物、及び該塗膜を形成する防汚処理方法 |
| AU2009327937B2 (en) * | 2008-12-19 | 2012-04-05 | Nitto Kasei Co., Ltd. | Antifouling coating composition, antifouling coating film formed using the composition, coated object having the coating film on the surface, and method of antifouling treatment by formation of the coating film |
| JP4521589B2 (ja) * | 2008-12-19 | 2010-08-11 | 日東化成株式会社 | 防汚塗料組成物、該組成物を用いて形成される防汚塗膜、該塗膜を表面に有する塗装物、及び該塗膜を形成する防汚処理方法 |
| JP2010150355A (ja) * | 2008-12-25 | 2010-07-08 | Nippon Paint Marine Kk | 防汚塗料組成物、防汚塗膜、ならびに防汚塗膜の加水分解速度の制御方法 |
| EP2489711B1 (en) * | 2009-10-13 | 2016-11-30 | Nippon Paint Marine Coatings Co., Ltd. | Antifouling coating composition, antifouling film, composite film, and in-water structure |
| WO2011046086A1 (ja) * | 2009-10-13 | 2011-04-21 | 日本ペイントマリン株式会社 | 防汚塗料組成物、ならびに防汚塗膜、複合塗膜および水中構造物 |
| EP2348077B1 (en) | 2010-01-26 | 2013-04-03 | Jotun A/S | Antifouling composition |
| JP4934851B2 (ja) | 2010-06-23 | 2012-05-23 | 日本ペイントマリン株式会社 | 防汚塗膜の形成方法 |
| EP2682437B8 (en) * | 2011-02-28 | 2019-10-02 | SANYO COLOR WORKS, Ltd. | Inkjet ink copolymer, inkjet ink pigment dispersing element using same, and inkjet ink |
| EP2708594A1 (en) | 2012-09-18 | 2014-03-19 | Jotun A/S | Cleaning process |
| WO2014064048A1 (en) | 2012-10-23 | 2014-05-01 | Jotun A/S | Antifouling coating composition |
| EP2725073B1 (en) | 2012-10-23 | 2016-08-03 | Jotun A/S | Antifouling coating composition |
| CN102964557B (zh) * | 2012-11-30 | 2015-04-22 | 华南理工大学 | 一种防污用水解降解树脂及其应用 |
| CN102977332B (zh) * | 2012-11-30 | 2015-04-22 | 华南理工大学 | 一种自分泌仿生防污材料及其应用 |
| CN104955828A (zh) | 2012-12-19 | 2015-09-30 | 佐敦集团 | 甲硅烷基酯共聚物 |
| KR20170074925A (ko) * | 2014-10-22 | 2017-06-30 | 닛토 가세이 가부시끼 가이샤 | 방오도료 조성물용 공중합체, 방오도료 조성물, 방오도막 |
| KR20180035832A (ko) | 2015-07-31 | 2018-04-06 | 주고꾸 도료 가부시키가이샤 | 방오 도료 조성물, 방오 도막, 방오 기재, 방오 도료 조성물용의 로진 화합물 및 방오 도료 조성물의 제조방법 |
| JP6472562B1 (ja) | 2018-07-03 | 2019-02-20 | 日本ペイントマリン株式会社 | 防汚塗料組成物用ビヒクル樹脂及びそれを含む防汚塗料組成物 |
| JP7351504B2 (ja) * | 2019-06-06 | 2023-09-27 | 日東化成株式会社 | 防汚塗料組成物 |
| GB2592921B (en) | 2020-03-09 | 2024-04-17 | Jotun As | Hull cleaning robot |
| JP2024514449A (ja) | 2021-03-23 | 2024-04-02 | ヨツン アクティーゼルスカブ | 水中の静止物体の表面の清浄度の監視 |
| GB202107159D0 (en) | 2021-03-23 | 2021-06-30 | Jotun As | Monitoring a vessel |
| WO2026057350A1 (en) | 2024-09-11 | 2026-03-19 | Akzo Nobel Coatings International B.V. | Antifouling coating compositions |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NO170424C (no) * | 1987-03-12 | 1992-10-14 | Nippon Paint Co Ltd | Harpikspartikler av desintegrasjonstypen, deres fremstilling og beleggsmiddel inneholdende slike partikler |
| JP2514217B2 (ja) | 1987-12-04 | 1996-07-10 | 東芝シリコーン株式会社 | 防汚コ―ティング材 |
| JP2775862B2 (ja) | 1989-06-27 | 1998-07-16 | 日本油脂株式会社 | 生物付着防止塗料組成物 |
| GB9008053D0 (en) * | 1990-04-10 | 1990-06-06 | Courtaulds Coatings Ltd | Coating compositions |
| AU636236B2 (en) * | 1990-07-19 | 1993-04-22 | Nippon Paint Co., Ltd. | Antifouling paint compositions |
| JP2956263B2 (ja) | 1991-02-18 | 1999-10-04 | 日本油脂株式会社 | 塗料組成物 |
| GB2257154B (en) * | 1991-06-26 | 1995-09-06 | Yung Chi Paint & Varnish Mfg C | Antifouling coating composition comprising a polymerisable metal soap |
| JP2790021B2 (ja) | 1993-09-30 | 1998-08-27 | 日本油脂株式会社 | 塗料組成物 |
| JP3062917B2 (ja) * | 1994-09-01 | 2000-07-12 | 日本ペイント株式会社 | 加水分解型金属含有樹脂および防汚塗料組成物 |
| TW319791B (https=) * | 1994-11-21 | 1997-11-11 | Nippon Oil Co Ltd | |
| SG60054A1 (en) * | 1996-04-17 | 1999-02-22 | Nof Corp | Coating composition |
| JPH10168350A (ja) * | 1996-12-10 | 1998-06-23 | Mitsubishi Rayon Co Ltd | 防汚性塗料組成物 |
| JP4118356B2 (ja) * | 1996-12-12 | 2008-07-16 | 日本ペイント株式会社 | 防汚塗料組成物 |
| ES2400167T3 (es) * | 1997-05-20 | 2013-04-08 | Mitsubishi Rayon Co. Ltd. | Composición de pintura antiincrustante |
| JP3498563B2 (ja) * | 1998-01-30 | 2004-02-16 | 日本油脂Ｂａｓｆコーティングス株式会社 | 水中防汚被覆剤 |
| PL200670B1 (pl) * | 1998-12-28 | 2009-01-30 | Chugoku Marine Paints | Kopolimer sililo(met)akrylanowy, sposób jego wytwarzania, przeciwporostowa kompozycja do malowania zawierająca kopolimer sililo(met)akrylanowy oraz jej zastosowanie |
| JP3857010B2 (ja) | 2000-02-17 | 2006-12-13 | 日本ペイント株式会社 | 共重合体及び塗料組成物 |
| KR20030025916A (ko) * | 2000-04-24 | 2003-03-29 | 니혼유시비에이에스에프코팅즈 가부시키가이샤 | 방오도료, 방오도막, 침수 구조체 및 방오방법 |
| JP2002256176A (ja) * | 2001-02-27 | 2002-09-11 | Chugoku Marine Paints Ltd | 複合防汚塗膜、該塗膜で被覆された船舶、水中構造物、漁具または漁網および防汚方法 |
-
2002
- 2002-12-23 NO NO20026203A patent/NO328137B1/no not_active IP Right Cessation
- 2002-12-24 EP EP02028942A patent/EP1323745B1/en not_active Expired - Lifetime
- 2002-12-24 JP JP2002372778A patent/JP3958681B2/ja not_active Expired - Lifetime
- 2002-12-24 DK DK02028942T patent/DK1323745T3/da active
- 2002-12-24 KR KR1020020083595A patent/KR100975322B1/ko not_active Expired - Lifetime
- 2002-12-24 AU AU2002325481A patent/AU2002325481B2/en not_active Expired
- 2002-12-24 DE DE60207968T patent/DE60207968T2/de not_active Expired - Lifetime
- 2002-12-25 TW TW091137244A patent/TWI290148B/zh not_active IP Right Cessation
- 2002-12-26 CN CNB021593035A patent/CN1250586C/zh not_active Expired - Lifetime
- 2002-12-26 US US10/329,605 patent/US6846878B2/en not_active Expired - Lifetime
- 2002-12-26 SG SG200207820A patent/SG123546A1/en unknown
-
2008
- 2008-09-15 NO NO20083930A patent/NO339571B1/no not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8263684B2 (en) | 2004-05-26 | 2012-09-11 | Nippon Paint Co., Ltd. | Coating composition, coating film, and method of reducing underwater friction |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1250586C (zh) | 2006-04-12 |
| EP1323745A2 (en) | 2003-07-02 |
| DE60207968T2 (de) | 2006-08-03 |
| EP1323745B1 (en) | 2005-12-14 |
| JP2003252931A (ja) | 2003-09-10 |
| SG123546A1 (en) | 2006-07-26 |
| NO20026203L (no) | 2003-06-27 |
| KR20030055157A (ko) | 2003-07-02 |
| US20030139558A1 (en) | 2003-07-24 |
| DK1323745T3 (da) | 2006-02-06 |
| DE60207968D1 (de) | 2006-01-19 |
| US6846878B2 (en) | 2005-01-25 |
| NO339571B1 (no) | 2017-01-09 |
| NO328137B1 (no) | 2009-12-14 |
| EP1323745A3 (en) | 2003-08-13 |
| JP3958681B2 (ja) | 2007-08-15 |
| AU2002325481B2 (en) | 2008-01-17 |
| KR100975322B1 (ko) | 2010-08-12 |
| CN1432585A (zh) | 2003-07-30 |
| TW200301263A (en) | 2003-07-01 |
| NO20026203D0 (no) | 2002-12-23 |
| NO20083930L (no) | 2003-06-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |