EP3710538A1 - Antifouling composition - Google Patents
Antifouling compositionInfo
- Publication number
- EP3710538A1 EP3710538A1 EP18804577.7A EP18804577A EP3710538A1 EP 3710538 A1 EP3710538 A1 EP 3710538A1 EP 18804577 A EP18804577 A EP 18804577A EP 3710538 A1 EP3710538 A1 EP 3710538A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- coating composition
- antifouling coating
- copolymer
- methyl
- acrylate
- 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
- 230000003373 anti-fouling effect Effects 0.000 title claims abstract description 95
- 239000000203 mixture Substances 0.000 title description 67
- 239000000178 monomer Substances 0.000 claims abstract description 113
- 229920001577 copolymer Polymers 0.000 claims abstract description 90
- 239000008199 coating composition Substances 0.000 claims abstract description 73
- 229920006243 acrylic copolymer Polymers 0.000 claims abstract description 59
- 239000011230 binding agent Substances 0.000 claims abstract description 30
- KNNOZYMZRGTZQM-UHFFFAOYSA-N tri(propan-2-yl)silyl 2-methylprop-2-enoate Chemical compound CC(C)[Si](C(C)C)(C(C)C)OC(=O)C(C)=C KNNOZYMZRGTZQM-UHFFFAOYSA-N 0.000 claims abstract description 24
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims abstract description 22
- XNFIRYXKTXAHAC-UHFFFAOYSA-N tralopyril Chemical compound BrC1=C(C(F)(F)F)NC(C=2C=CC(Cl)=CC=2)=C1C#N XNFIRYXKTXAHAC-UHFFFAOYSA-N 0.000 claims abstract description 19
- 230000009477 glass transition Effects 0.000 claims abstract description 10
- 238000000576 coating method Methods 0.000 claims description 63
- 239000011248 coating agent Substances 0.000 claims description 55
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 46
- 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 37
- 239000003139 biocide Substances 0.000 claims description 34
- 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 31
- 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 31
- 239000007787 solid Substances 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 6
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 claims description 6
- 150000004292 cyclic ethers Chemical group 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 5
- FTALTLPZDVFJSS-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl prop-2-enoate Chemical compound CCOCCOCCOC(=O)C=C FTALTLPZDVFJSS-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 claims description 4
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 3
- WFTWWOCWRSUGAW-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl 2-methylprop-2-enoate Chemical compound CCOCCOCCOC(=O)C(C)=C WFTWWOCWRSUGAW-UHFFFAOYSA-N 0.000 claims description 3
- YXYJVFYWCLAXHO-UHFFFAOYSA-N 2-methoxyethyl 2-methylprop-2-enoate Chemical compound COCCOC(=O)C(C)=C YXYJVFYWCLAXHO-UHFFFAOYSA-N 0.000 claims description 3
- HFCUBKYHMMPGBY-UHFFFAOYSA-N 2-methoxyethyl prop-2-enoate Chemical compound COCCOC(=O)C=C HFCUBKYHMMPGBY-UHFFFAOYSA-N 0.000 claims description 3
- NUXLDNTZFXDNBA-UHFFFAOYSA-N 6-bromo-2-methyl-4h-1,4-benzoxazin-3-one Chemical compound C1=C(Br)C=C2NC(=O)C(C)OC2=C1 NUXLDNTZFXDNBA-UHFFFAOYSA-N 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-UHFFFAOYSA-N 0.000 claims description 3
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 3
- 239000011717 all-trans-retinol Substances 0.000 claims description 3
- 235000019169 all-trans-retinol Nutrition 0.000 claims description 3
- QHNCWVQDOPICKC-UHFFFAOYSA-N copper;1-hydroxypyridine-2-thione Chemical compound [Cu].ON1C=CC=CC1=S.ON1C=CC=CC1=S QHNCWVQDOPICKC-UHFFFAOYSA-N 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 3
- 229940043810 zinc pyrithione Drugs 0.000 claims description 3
- 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 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 2
- 239000005749 Copper compound Substances 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000001880 copper compounds Chemical class 0.000 claims 1
- -1 components (i) Chemical class 0.000 description 54
- 239000000243 solution Substances 0.000 description 37
- 229920000642 polymer Polymers 0.000 description 35
- 239000002253 acid Substances 0.000 description 29
- 238000005498 polishing Methods 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 24
- 239000003973 paint Substances 0.000 description 22
- 239000002904 solvent Substances 0.000 description 21
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 14
- 230000003115 biocidal effect Effects 0.000 description 14
- 239000008096 xylene Substances 0.000 description 14
- 150000007513 acids Chemical class 0.000 description 13
- 229910052802 copper Inorganic materials 0.000 description 12
- 239000010949 copper Substances 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 11
- 238000005259 measurement Methods 0.000 description 11
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-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
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 239000012855 volatile organic compound Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 229940063557 methacrylate Drugs 0.000 description 7
- 239000013535 sea water Substances 0.000 description 7
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 6
- RXGUIWHIADMCFC-UHFFFAOYSA-N 2-Methylpropyl 2-methylpropionate Chemical compound CC(C)COC(=O)C(C)C RXGUIWHIADMCFC-UHFFFAOYSA-N 0.000 description 6
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 6
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 6
- UHZZMRAGKVHANO-UHFFFAOYSA-M chlormequat chloride Chemical compound [Cl-].C[N+](C)(C)CCCl UHZZMRAGKVHANO-UHFFFAOYSA-M 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000003999 initiator Substances 0.000 description 6
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 6
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000004014 plasticizer Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 229910052725 zinc Inorganic materials 0.000 description 6
- 239000011701 zinc Substances 0.000 description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 239000002519 antifouling agent Substances 0.000 description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
- 239000011324 bead Substances 0.000 description 5
- 150000007942 carboxylates Chemical class 0.000 description 5
- 230000015556 catabolic process Effects 0.000 description 5
- 238000005336 cracking Methods 0.000 description 5
- 238000006731 degradation reaction Methods 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000000049 pigment Substances 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 229920000915 polyvinyl chloride Polymers 0.000 description 5
- 239000004800 polyvinyl chloride Substances 0.000 description 5
- 239000006254 rheological additive Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- 239000001993 wax Substances 0.000 description 5
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- 241000238586 Cirripedia Species 0.000 description 4
- 239000004606 Fillers/Extenders Substances 0.000 description 4
- 241000131858 Siboglinidae Species 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000013022 formulation composition Substances 0.000 description 4
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000001023 inorganic pigment Substances 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 4
- 229920005604 random copolymer Polymers 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([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
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 3
- UHOPWFKONJYLCF-UHFFFAOYSA-N 2-(2-sulfanylethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCS)C(=O)C2=C1 UHOPWFKONJYLCF-UHFFFAOYSA-N 0.000 description 3
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 3
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 3
- LXUJDFITFWBMQT-UHFFFAOYSA-M 2-ethylhexyl carbonate Chemical compound CCCCC(CC)COC([O-])=O LXUJDFITFWBMQT-UHFFFAOYSA-M 0.000 description 3
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- 241000237536 Mytilus edulis Species 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- 125000002015 acyclic group Chemical group 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 229940072049 amyl acetate Drugs 0.000 description 3
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 3
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 3
- 235000019445 benzyl alcohol Nutrition 0.000 description 3
- BTMVHUNTONAYDX-UHFFFAOYSA-N butyl propionate Chemical compound CCCCOC(=O)CC BTMVHUNTONAYDX-UHFFFAOYSA-N 0.000 description 3
- 239000002274 desiccant Substances 0.000 description 3
- WURGXGVFSMYFCG-UHFFFAOYSA-N dichlofluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=CC=C1 WURGXGVFSMYFCG-UHFFFAOYSA-N 0.000 description 3
- 238000000113 differential scanning calorimetry Methods 0.000 description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 229920006334 epoxy coating Polymers 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 3
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- 235000001510 limonene Nutrition 0.000 description 3
- 229940087305 limonene Drugs 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 3
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 235000020638 mussel Nutrition 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000012860 organic pigment Substances 0.000 description 3
- 150000001282 organosilanes Chemical class 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000012744 reinforcing agent Substances 0.000 description 3
- 150000003505 terpenes Chemical class 0.000 description 3
- 235000007586 terpenes Nutrition 0.000 description 3
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 3
- HGXJDMCMYLEZMJ-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOOC(=O)C(C)(C)C HGXJDMCMYLEZMJ-UHFFFAOYSA-N 0.000 description 2
- 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
- IMYCVFRTNVMHAD-UHFFFAOYSA-N 1,1-bis(2-methylbutan-2-ylperoxy)cyclohexane Chemical compound CCC(C)(C)OOC1(OOC(C)(C)CC)CCCCC1 IMYCVFRTNVMHAD-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-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
- AQKYLAIZOGOPAW-UHFFFAOYSA-N 2-methylbutan-2-yl 2,2-dimethylpropaneperoxoate Chemical compound CCC(C)(C)OOC(=O)C(C)(C)C AQKYLAIZOGOPAW-UHFFFAOYSA-N 0.000 description 2
- IFXDUNDBQDXPQZ-UHFFFAOYSA-N 2-methylbutan-2-yl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)CC IFXDUNDBQDXPQZ-UHFFFAOYSA-N 0.000 description 2
- 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 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
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 241000195628 Chlorophyta Species 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229920000028 Gradient copolymer Polymers 0.000 description 2
- 239000013032 Hydrocarbon resin Substances 0.000 description 2
- 241000243320 Hydrozoa Species 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 241000199919 Phaeophyceae Species 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229920003232 aliphatic polyester Polymers 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 229910001570 bauxite Inorganic materials 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 238000012662 bulk polymerization Methods 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 238000013270 controlled release Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- VBWIZSYFQSOUFQ-UHFFFAOYSA-N cyclohexanecarbonitrile Chemical compound N#CC1CCCCC1 VBWIZSYFQSOUFQ-UHFFFAOYSA-N 0.000 description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 2
- 238000012674 dispersion polymerization Methods 0.000 description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- 229920006270 hydrocarbon resin Polymers 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 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
- 239000007788 liquid Substances 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 2
- 239000001095 magnesium carbonate Substances 0.000 description 2
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 2
- 235000014380 magnesium carbonate Nutrition 0.000 description 2
- HRLIOXLXPOHXTA-UHFFFAOYSA-N medetomidine Chemical compound C=1C=CC(C)=C(C)C=1C(C)C1=CN=C[N]1 HRLIOXLXPOHXTA-UHFFFAOYSA-N 0.000 description 2
- 229960002140 medetomidine Drugs 0.000 description 2
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000011490 mineral wool Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000010557 suspension polymerization reaction Methods 0.000 description 2
- KXYJPVZMZBJJBZ-UHFFFAOYSA-N tert-butyl 2-ethylbutaneperoxoate Chemical compound CCC(CC)C(=O)OOC(C)(C)C KXYJPVZMZBJJBZ-UHFFFAOYSA-N 0.000 description 2
- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 0.000 description 2
- PFBLRDXPNUJYJM-UHFFFAOYSA-N tert-butyl 2-methylpropaneperoxoate Chemical compound CC(C)C(=O)OOC(C)(C)C PFBLRDXPNUJYJM-UHFFFAOYSA-N 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- PQSIXYSSKXAOFE-UHFFFAOYSA-N tri(propan-2-yl)silyl prop-2-enoate Chemical compound CC(C)[Si](C(C)C)(C(C)C)OC(=O)C=C PQSIXYSSKXAOFE-UHFFFAOYSA-N 0.000 description 2
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 2
- 239000010456 wollastonite Substances 0.000 description 2
- 229910052882 wollastonite Inorganic materials 0.000 description 2
- VNTDZUDTQCZFKN-UHFFFAOYSA-L zinc 2,2-dimethyloctanoate Chemical compound [Zn++].CCCCCCC(C)(C)C([O-])=O.CCCCCCC(C)(C)C([O-])=O VNTDZUDTQCZFKN-UHFFFAOYSA-L 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- 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 1
- UXBFAGQTUAMQSX-PKUWUEBNSA-N (1R)-1,3-dimethyl-2-[2-(3-propan-2-ylphenyl)ethyl]cyclohexane-1-carboxylic acid Chemical compound CC(C)c1cccc(CCC2C(C)CCC[C@@]2(C)C(O)=O)c1 UXBFAGQTUAMQSX-PKUWUEBNSA-N 0.000 description 1
- HPQKNJHVWUWAOR-BWCMQUJESA-N (1S,4aR,5S,8aR)-5-[(3S)-4-carboxy-3-methylbutyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid Chemical compound [C@H]1([C@@](CCC2)(C)C(O)=O)[C@@]2(C)[C@@H](CC[C@H](C)CC(O)=O)C(=C)CC1 HPQKNJHVWUWAOR-BWCMQUJESA-N 0.000 description 1
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- XFKFBBVGUXNVOU-UHFFFAOYSA-N (4,5-dihydroxy-2-methylpent-2-en-3-yl) 2-methylprop-2-enoate Chemical compound OCC(O)C(=C(C)C)OC(=O)C(C)=C XFKFBBVGUXNVOU-UHFFFAOYSA-N 0.000 description 1
- 125000006659 (C1-C20) hydrocarbyl group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- HSFXEOPJXMFQHG-ARJAWSKDSA-N (z)-4-[2-(2-methylprop-2-enoyloxy)ethoxy]-4-oxobut-2-enoic acid Chemical compound CC(=C)C(=O)OCCOC(=O)\C=C/C(O)=O HSFXEOPJXMFQHG-ARJAWSKDSA-N 0.000 description 1
- FGWYWKIOMUZSQF-UHFFFAOYSA-N 1,1,1-triethoxypropane Chemical compound CCOC(CC)(OCC)OCC FGWYWKIOMUZSQF-UHFFFAOYSA-N 0.000 description 1
- HDPNBNXLBDFELL-UHFFFAOYSA-N 1,1,1-trimethoxyethane Chemical compound COC(C)(OC)OC HDPNBNXLBDFELL-UHFFFAOYSA-N 0.000 description 1
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 1
- GLPHLPJFRQFZNS-UHFFFAOYSA-N 1,2,3-trimethyl-5-(2-methylprop-1-enyl)cyclohex-3-ene-1-carboxylic acid Chemical compound CC1C(C)=CC(C=C(C)C)CC1(C)C(O)=O GLPHLPJFRQFZNS-UHFFFAOYSA-N 0.000 description 1
- ISZHXRVFIWHKKK-UHFFFAOYSA-N 1,4,5-trimethyl-2-(2-methylprop-1-enyl)cyclohex-3-ene-1-carboxylic acid Chemical compound CC1CC(C)(C(O)=O)C(C=C(C)C)C=C1C ISZHXRVFIWHKKK-UHFFFAOYSA-N 0.000 description 1
- NDEGPPPYPNVXEZ-UHFFFAOYSA-N 1,4,5-trimethyl-2-(2-methylprop-2-enyl)cyclohex-3-ene-1-carboxylic acid Chemical compound CC1(C(C=C(C(C1)C)C)CC(=C)C)C(=O)O NDEGPPPYPNVXEZ-UHFFFAOYSA-N 0.000 description 1
- FWPUNGDZMWDFKB-UHFFFAOYSA-N 1,4-dimethyl-5-(3-methylbut-2-enyl)cyclohex-3-ene-1-carboxylic acid Chemical compound CC(C)=CCC1CC(C)(C(O)=O)CC=C1C FWPUNGDZMWDFKB-UHFFFAOYSA-N 0.000 description 1
- SGJBIFUEFLWXJY-UHFFFAOYSA-N 1-(dibutoxymethoxy)butane Chemical compound CCCCOC(OCCCC)OCCCC SGJBIFUEFLWXJY-UHFFFAOYSA-N 0.000 description 1
- RWNXXQFJBALKAX-UHFFFAOYSA-N 1-(dipropoxymethoxy)propane Chemical compound CCCOC(OCCC)OCCC RWNXXQFJBALKAX-UHFFFAOYSA-N 0.000 description 1
- YFCNEIWVIJVLHW-UHFFFAOYSA-N 1-methyl-3-(4-methylpent-3-enyl)cyclohex-3-ene-1-carboxylic acid Chemical compound CC(C)=CCCC1=CCCC(C)(C(O)=O)C1 YFCNEIWVIJVLHW-UHFFFAOYSA-N 0.000 description 1
- QVJSHLNKUYTRMT-UHFFFAOYSA-N 1-methyl-4-(4-methylpent-3-enyl)cyclohex-3-ene-1-carboxylic acid Chemical compound CC(C)=CCCC1=CCC(C)(C(O)=O)CC1 QVJSHLNKUYTRMT-UHFFFAOYSA-N 0.000 description 1
- WPIQTKMKIKWAJR-UHFFFAOYSA-N 1-methyl-4-propan-2-ylbicyclo[2.2.2]oct-5-ene-2-carboxylic acid Chemical compound C1CC2(C)C=CC1(C(C)C)CC2C(O)=O WPIQTKMKIKWAJR-UHFFFAOYSA-N 0.000 description 1
- ZONJATNKKGGVSU-UHFFFAOYSA-N 14-methylpentadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCC(O)=O ZONJATNKKGGVSU-UHFFFAOYSA-N 0.000 description 1
- OJBOWZVSJWNXKS-UHFFFAOYSA-N 2,2,3,5-tetramethylhexanoic acid Chemical compound CC(C)CC(C)C(C)(C)C(O)=O OJBOWZVSJWNXKS-UHFFFAOYSA-N 0.000 description 1
- IMHQFVGHBDXALM-UHFFFAOYSA-N 2,2-diethylhexanoic acid Chemical compound CCCCC(CC)(CC)C(O)=O IMHQFVGHBDXALM-UHFFFAOYSA-N 0.000 description 1
- IKNDGHRNXGEHTO-UHFFFAOYSA-N 2,2-dimethyloctanoic acid Chemical compound CCCCCCC(C)(C)C(O)=O IKNDGHRNXGEHTO-UHFFFAOYSA-N 0.000 description 1
- DPGYCJUCJYUHTM-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-yloxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)CC(C)(C)C DPGYCJUCJYUHTM-UHFFFAOYSA-N 0.000 description 1
- WWPDEUORQAIWDC-UHFFFAOYSA-N 2,4-dimethyl-2-propan-2-ylpentanoic acid Chemical compound CC(C)CC(C)(C(C)C)C(O)=O WWPDEUORQAIWDC-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
- FIYMNUNPPYABMU-UHFFFAOYSA-N 2-benzyl-5-chloro-1h-indole Chemical compound C=1C2=CC(Cl)=CC=C2NC=1CC1=CC=CC=C1 FIYMNUNPPYABMU-UHFFFAOYSA-N 0.000 description 1
- PKJSRUTWBDIWAR-UHFFFAOYSA-N 2-ethyl-2,5-dimethylhexanoic acid Chemical compound CCC(C)(C(O)=O)CCC(C)C PKJSRUTWBDIWAR-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
- RMVVLWLIVYSRFT-UHFFFAOYSA-N 2-methyl-8-propan-2-ylbicyclo[2.2.2]oct-2-ene-5-carboxylic acid Chemical compound C1C(C(O)=O)C2C(C(C)C)CC1C(C)=C2 RMVVLWLIVYSRFT-UHFFFAOYSA-N 0.000 description 1
- WUGOQZFPNUYUOO-UHFFFAOYSA-N 2-trimethylsilyloxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCO[Si](C)(C)C WUGOQZFPNUYUOO-UHFFFAOYSA-N 0.000 description 1
- OILUAKBAMVLXGF-UHFFFAOYSA-N 3,5,5-trimethyl-hexanoic acid Chemical compound OC(=O)CC(C)CC(C)(C)C OILUAKBAMVLXGF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- CYUZOYPRAQASLN-UHFFFAOYSA-N 3-prop-2-enoyloxypropanoic acid Chemical compound OC(=O)CCOC(=O)C=C CYUZOYPRAQASLN-UHFFFAOYSA-N 0.000 description 1
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 1
- ZEWLHMQYEZXSBH-UHFFFAOYSA-N 4-[2-(2-methylprop-2-enoyloxy)ethoxy]-4-oxobutanoic acid Chemical compound CC(=C)C(=O)OCCOC(=O)CCC(O)=O ZEWLHMQYEZXSBH-UHFFFAOYSA-N 0.000 description 1
- MLBYBBUZURKHAW-UHFFFAOYSA-N 4-epi-Palustrinsaeure Natural products CC12CCCC(C)(C(O)=O)C1CCC1=C2CCC(C(C)C)=C1 MLBYBBUZURKHAW-UHFFFAOYSA-N 0.000 description 1
- VLJQDHDVZJXNQL-UHFFFAOYSA-N 4-methyl-n-(oxomethylidene)benzenesulfonamide Chemical compound CC1=CC=C(S(=O)(=O)N=C=O)C=C1 VLJQDHDVZJXNQL-UHFFFAOYSA-N 0.000 description 1
- KIYKTWDNCDHWBB-UHFFFAOYSA-N 5-but-3-en-2-yl-1,2,3-trimethylcyclohex-3-ene-1-carboxylic acid Chemical compound CC1(C(C(=CC(C1)C(C=C)C)C)C)C(=O)O KIYKTWDNCDHWBB-UHFFFAOYSA-N 0.000 description 1
- UPPCCJWKDIKFJH-UHFFFAOYSA-N 5-methyl-2-propan-2-ylbicyclo[2.2.2]oct-5-ene-8-carboxylic acid Chemical compound OC(=O)C1CC2C(C(C)C)CC1C(C)=C2 UPPCCJWKDIKFJH-UHFFFAOYSA-N 0.000 description 1
- XSIUOXMDYLBMER-UHFFFAOYSA-N 6-methoxycarbonyl-2,3-dimethyl-5-(2-methylprop-1-enyl)cyclohex-3-ene-1-carboxylic acid Chemical compound COC(=O)C1C(C=C(C)C)C=C(C)C(C)C1C(O)=O XSIUOXMDYLBMER-UHFFFAOYSA-N 0.000 description 1
- YPIFGDQKSSMYHQ-UHFFFAOYSA-N 7,7-dimethyloctanoic acid Chemical compound CC(C)(C)CCCCCC(O)=O YPIFGDQKSSMYHQ-UHFFFAOYSA-N 0.000 description 1
- XZOYHFBNQHPJRQ-UHFFFAOYSA-N 7-methyloctanoic acid Chemical compound CC(C)CCCCCC(O)=O XZOYHFBNQHPJRQ-UHFFFAOYSA-N 0.000 description 1
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000206761 Bacillariophyta Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241001474374 Blennius Species 0.000 description 1
- 241000700670 Bryozoa Species 0.000 description 1
- BUMCACNXOIGACX-UHFFFAOYSA-N C(C)(OCCCC)(OCCCC)OCCCC.C(C)(OCC)(OCC)OCC Chemical compound C(C)(OCCCC)(OCCCC)OCCCC.C(C)(OCC)(OCC)OCC BUMCACNXOIGACX-UHFFFAOYSA-N 0.000 description 1
- 229910021532 Calcite Inorganic materials 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- YGBZFOQXPOGACY-CUDHKJQZSA-N Communic acid Natural products CC(C=C)=CC[C@H]1C(=C)CC[C@@H]2[C@]1(C)CCC[C@]2(C)C(O)=O YGBZFOQXPOGACY-CUDHKJQZSA-N 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- QUUCYKKMFLJLFS-UHFFFAOYSA-N Dehydroabietan Natural products CC1(C)CCCC2(C)C3=CC=C(C(C)C)C=C3CCC21 QUUCYKKMFLJLFS-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- RWWVEQKPFPXLGL-ONCXSQPRSA-N L-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 RWWVEQKPFPXLGL-ONCXSQPRSA-N 0.000 description 1
- JEGUVXRNDRXUDN-UHFFFAOYSA-N Labdatriene Natural products C1CCC(C)(C(O)=O)C2CCC(=C)C(CCC(=C)C=C)C21C JEGUVXRNDRXUDN-UHFFFAOYSA-N 0.000 description 1
- RWWVEQKPFPXLGL-UHFFFAOYSA-N Levopimaric acid Natural products C1CCC(C(O)=O)(C)C2C1(C)C1CC=C(C(C)C)C=C1CC2 RWWVEQKPFPXLGL-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- KGMSWPSAVZAMKR-UHFFFAOYSA-N Me ester-3, 22-Dihydroxy-29-hopanoic acid Natural products C1CCC(C(O)=O)(C)C2C1(C)C1CCC(=C(C)C)C=C1CC2 KGMSWPSAVZAMKR-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- KGMSWPSAVZAMKR-ONCXSQPRSA-N Neoabietic acid Chemical compound [C@H]1([C@](CCC2)(C)C(O)=O)[C@@]2(C)[C@H]2CCC(=C(C)C)C=C2CC1 KGMSWPSAVZAMKR-ONCXSQPRSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- HPQKNJHVWUWAOR-UHFFFAOYSA-N Oliveric acid Natural products C1CCC(C(O)=O)(C)C2C1(C)C(CCC(C)CC(O)=O)C(=C)CC2 HPQKNJHVWUWAOR-UHFFFAOYSA-N 0.000 description 1
- 241000237502 Ostreidae Species 0.000 description 1
- MLBYBBUZURKHAW-MISYRCLQSA-N Palustric acid Chemical compound C([C@@]12C)CC[C@@](C)(C(O)=O)[C@@H]1CCC1=C2CCC(C(C)C)=C1 MLBYBBUZURKHAW-MISYRCLQSA-N 0.000 description 1
- 229920000954 Polyglycolide Polymers 0.000 description 1
- OEYVFRVNVPKHQQ-UHFFFAOYSA-N Pyrimidin-4-yl-Methanol Chemical compound OCC1=CC=NC=N1 OEYVFRVNVPKHQQ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 239000005083 Zinc sulfide Substances 0.000 description 1
- 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 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 229920005822 acrylic binder Polymers 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 238000012644 addition polymerization Methods 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 229920005603 alternating copolymer Polymers 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical class [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000010428 baryte Substances 0.000 description 1
- 229910052601 baryte Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- ZOMBKNNSYQHRCA-UHFFFAOYSA-J calcium sulfate hemihydrate Chemical compound O.[Ca+2].[Ca+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O ZOMBKNNSYQHRCA-UHFFFAOYSA-J 0.000 description 1
- 239000001175 calcium sulphate Substances 0.000 description 1
- 235000011132 calcium sulphate Nutrition 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000007156 chain growth polymerization reaction Methods 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- 229910001919 chlorite Inorganic materials 0.000 description 1
- 229910052619 chlorite group Inorganic materials 0.000 description 1
- QBWCMBCROVPCKQ-UHFFFAOYSA-N chlorous acid Chemical compound OCl=O QBWCMBCROVPCKQ-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000012505 colouration Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- BQVVSSAWECGTRN-UHFFFAOYSA-L copper;dithiocyanate Chemical compound [Cu+2].[S-]C#N.[S-]C#N BQVVSSAWECGTRN-UHFFFAOYSA-L 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000013078 crystal Substances 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
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 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 description 1
- 229940118781 dehydroabietic acid Drugs 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 238000004710 electron pair approximation Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 150000002084 enol ethers Chemical class 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 239000010433 feldspar Substances 0.000 description 1
- 238000009472 formulation Methods 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
- 229940074076 glycerol formal Drugs 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229920001480 hydrophilic copolymer Polymers 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- WTFXARWRTYJXII-UHFFFAOYSA-N iron(2+);iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Fe+2].[Fe+3].[Fe+3] WTFXARWRTYJXII-UHFFFAOYSA-N 0.000 description 1
- LDHBWEYLDHLIBQ-UHFFFAOYSA-M iron(3+);oxygen(2-);hydroxide;hydrate Chemical compound O.[OH-].[O-2].[Fe+3] LDHBWEYLDHLIBQ-UHFFFAOYSA-M 0.000 description 1
- SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 229940117955 isoamyl acetate Drugs 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 238000003032 molecular docking Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- JCNCSCMYYGONLU-UHFFFAOYSA-N n,n'-bis(2-methylphenyl)methanediimine Chemical compound CC1=CC=CC=C1N=C=NC1=CC=CC=C1C JCNCSCMYYGONLU-UHFFFAOYSA-N 0.000 description 1
- XLDBGFGREOMWSL-UHFFFAOYSA-N n,n'-bis[2,6-di(propan-2-yl)phenyl]methanediimine Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N=C=NC1=C(C(C)C)C=CC=C1C(C)C XLDBGFGREOMWSL-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000010434 nepheline Substances 0.000 description 1
- 229910052664 nepheline Inorganic materials 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 150000002905 orthoesters Chemical class 0.000 description 1
- 235000020636 oyster Nutrition 0.000 description 1
- YGBZFOQXPOGACY-UHFFFAOYSA-N ozic acid Natural products C1CCC(C(O)=O)(C)C2C1(C)C(CC=C(C=C)C)C(=C)CC2 YGBZFOQXPOGACY-UHFFFAOYSA-N 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- MKTRXTLKNXLULX-UHFFFAOYSA-P pentacalcium;dioxido(oxo)silane;hydron;tetrahydrate Chemical compound [H+].[H+].O.O.O.O.[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-][Si]([O-])=O.[O-][Si]([O-])=O.[O-][Si]([O-])=O.[O-][Si]([O-])=O.[O-][Si]([O-])=O.[O-][Si]([O-])=O MKTRXTLKNXLULX-UHFFFAOYSA-P 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
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 1
- 229920001485 poly(butyl acrylate) polymer Polymers 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000352 poly(styrene-co-divinylbenzene) Polymers 0.000 description 1
- 229920002432 poly(vinyl methyl ether) polymer Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- WJSXSXUHWBSPEP-UHFFFAOYSA-N pyridine;triphenylborane Chemical compound C1=CC=NC=C1.C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 WJSXSXUHWBSPEP-UHFFFAOYSA-N 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 238000007665 sagging Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- MHVJRKBZMUDEEV-KRFUXDQASA-N sandaracopimaric 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-KRFUXDQASA-N 0.000 description 1
- YZVSLDRKXBZOMY-KNOXWWKRSA-N sandaracopimaric acid Natural products CC(=C)[C@]1(C)CCC[C@]2(C)[C@H]3CC[C@](C)(C=C)C=C3CC[C@@H]12 YZVSLDRKXBZOMY-KNOXWWKRSA-N 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001797 sucrose acetate isobutyrate Substances 0.000 description 1
- UVGUPMLLGBCFEJ-SWTLDUCYSA-N sucrose acetate isobutyrate Chemical compound CC(C)C(=O)O[C@H]1[C@H](OC(=O)C(C)C)[C@@H](COC(=O)C(C)C)O[C@@]1(COC(C)=O)O[C@@H]1[C@H](OC(=O)C(C)C)[C@@H](OC(=O)C(C)C)[C@H](OC(=O)C(C)C)[C@@H](COC(C)=O)O1 UVGUPMLLGBCFEJ-SWTLDUCYSA-N 0.000 description 1
- 235000010983 sucrose acetate isobutyrate Nutrition 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000010435 syenite Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 1
- NKLYMYLJOXIVFB-UHFFFAOYSA-N triethoxymethylsilane Chemical compound CCOC([SiH3])(OCC)OCC NKLYMYLJOXIVFB-UHFFFAOYSA-N 0.000 description 1
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- TUQLLQQWSNWKCF-UHFFFAOYSA-N trimethoxymethylsilane Chemical compound COC([SiH3])(OC)OC TUQLLQQWSNWKCF-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- LTEHWCSSIHAVOQ-UHFFFAOYSA-N tripropyl borate Chemical compound CCCOB(OCCC)OCCC LTEHWCSSIHAVOQ-UHFFFAOYSA-N 0.000 description 1
- ZMCWFMOZBTXGKI-UHFFFAOYSA-N tritert-butyl borate Chemical compound CC(C)(C)OB(OC(C)(C)C)OC(C)(C)C ZMCWFMOZBTXGKI-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- 239000011686 zinc sulphate Substances 0.000 description 1
- 235000009529 zinc sulphate Nutrition 0.000 description 1
- LPEBYPDZMWMCLZ-CVBJKYQLSA-L zinc;(z)-octadec-9-enoate Chemical compound [Zn+2].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O LPEBYPDZMWMCLZ-CVBJKYQLSA-L 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 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
- C09D5/1656—Antifouling paints; Underwater paints characterised by the film-forming substance
- C09D5/1662—Synthetic film-forming substance
- C09D5/1668—Vinyl-type polymers
-
- C—CHEMISTRY; METALLURGY
- 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
- C09D133/00—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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/02—Homopolymers or copolymers of acids; Metal or ammonium salts thereof
-
- 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
- C09D133/00—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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
-
- 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
- C09D133/00—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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/08—Homopolymers or copolymers of acrylic acid esters
-
- 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
- C09D133/00—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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/10—Homopolymers or copolymers of methacrylic acid esters
- C09D133/12—Homopolymers or copolymers of methyl methacrylate
-
- 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
- C09D193/00—Coating compositions based on natural resins; Coating compositions based on derivatives thereof
- C09D193/04—Rosin
-
- 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
- C09D5/1612—Non-macromolecular compounds
- C09D5/1618—Non-macromolecular compounds inorganic
-
- 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
- C09D5/1612—Non-macromolecular compounds
- C09D5/1625—Non-macromolecular compounds organic
-
- 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
-
- 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
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered rings
Definitions
- the present invention relates to marine antifouling coating compositions, more specifically to marine antifouling coating compositions comprising a silyl ester copolymer comprising triisopropylsilyl methacrylate as a monomer.
- composition additionally contains an acrylic copolymer having a low Tg and preferably containing an acidic monomer, a monocarboxylic acid or derivative thereof and tralopyril as a biocide.
- the invention further relates to a method of protecting objects from fouling, and to objects coated with the antifouling composition of the invention. Background of invention
- antifouling paints are used. These paints generally comprise a film- forming binder, together with different components such as pigments, fillers, additives and solvents together with biologically active substances (biocides). Biocides can be broadly divided into those active against soft fouling, such as green and brown algae, grass, slime and those active against hard fouling, such as barnacles, mussels, tube worms etc.
- Typical service intervals for commercial vessels range from 24 to 90 months. It requires a controlled release of biocides from the coating film through the entire service interval to protect the object from fouling. That can best be obtained by using a self-polishing antifouling coating having a controlled polishing rate. Too fast polishing will lead to a rapid consumption of the coating film, resulting in an unprotected surface. Too slow polishing will lead to insufficient release of the biocide, which is vital for effective protection from fouling. A controlled degradation over the life time will give a constant release of biocides and thereby excellent fouling protection.
- the binder matrix consists of silyl ester copolymers often together with other binders such as acrylates and rosin or rosin derivatives to adjust the self-polishing properties and the mechanical properties of antifouling coating films.
- an antifouling coating contains copper based biocides such as cuprous oxide, copper thiocyanate and like.
- copper based biocides such as cuprous oxide, copper thiocyanate and like.
- new metal-free organic biocides have been put on the market. Their efficiency allows lower loading of biocides in the formulation.
- Tralopyril is an organic biocide which has been shown to be very effective against a broad spectrum of hard- shelled fouling organisms including barnacles, hydroids, mussels, oysters and tube worms.
- Antifouling coating compositions based on silyl ester copolymers which employ tralopyril as a biocide are disclosed in, for example, EP 3078715 and
- Controlled polishing and good mechanical properties of coatings can often be achieved by adjusting the ratios of the binder components.
- Antifouling coating compositions comprising tralopyril provide a solution that gives broader protection against marine fouling than other solutions without inorganic copper biocides in the market.
- the antifouling coating polishes at a constant rate through the whole life time of the coating system to provide good fouling protection. Insufficient fouling protection will increase the operational cost, such as fuel consumption and/or cost of underwater hull cleaning. It is also vital that the coating system can be applied in acceptable film thicknesses. High film thickness is costly for the customer with respect to the cost of the paint applied and extended time in dock resulting in increased docking fees and extended time out of business. Other disadvantages of applying high film thickness is risk of sagging during application and poor release of solvents during drying resulting in increased drying times, soft coatings and/or risk of coating failures such as blistering and flaking when immersed in sea water.
- An antifouling coating composition comprising a silyl methacrylate copolymer and tralopyril having a controlled polishing and degradation rate of the coating system is therefore needed.
- the present inventors have found that controlled polishing and good mechanical properties can be achieved by employing a triisopropylsilyl methacrylate copolymer and a monocarboxylic acid together with acrylic copolymers as the third component of the binder matrix, followed by optimization of the final binder mixture. They have established that using this binder in combination with tralopyril provides a self-polishing antifouling system with improved antifouling performance. Moreover, the antifouling composition of the invention has very good resistance to cracking and very good self-polishing properties.
- the invention relates to an antifouling coating composition
- an antifouling coating composition comprising:
- the invention provides a process for protecting an object from fouling, said process comprising coating at least a part of said object which is subject to fouling with an antifouling coating composition as defined herein.
- the invention also relates to objects coated with the antifouling coating composition as defined herein.
- the invention relates to the use of the binder (A) as defined herein in an antifouling coating composition comprising tralopyril, i.e. as a binder for such a composition.
- marine antifouling coating composition “antifouling coating composition” or simply“coating composition” refer to a composition that, when applied to a surface, prevents or minimises growth of marine organisms on the surface.
- hydrocarbyl group refers to any group containing C atoms and H atoms only and therefore covers alkyl, alkenyl, aryl, cycloalkyl, arylalkyl groups and so on.
- acrylic copolymer refers to a copolymer comprising repeating units derived from (meth)acrylate monomers. Generally an acrylic copolymer will comprise at least 80 wt% of the repeating units derived from (meth)acrylate monomers, i.e. acrylate and/or methacrylate monomers.
- (meth)acrylate means a methacrylate or acrylate.
- “monocarboxylic acid” refers to a compound comprising one -COOH group.
- resin acid refers to a mixture of carboxylic acids present in resins.
- binder defines part of the composition which includes the silyl ester copolymer and any other components which together form a matrix giving substance and strength to the composition.
- binder used herein means the silyl ester copolymer together with the monocarboxylic acid and acrylic copolymer, i.e. components (i), (ii) and (iii) as defined herein.
- Tg glass transition temperature
- the wt% is relative to the sum total (weight) of each monomer present in the copolymer.
- wt% based on the total weight of the composition refers to the wt% of a component present in the final, ready to use, composition, unless otherwise specified.
- the invention relates to a new antifouling coating composition
- a binder which contains a mixture of (i) a silyl ester copolymer comprising triisopropylsilyl methacrylate monomers; (ii) a monocarboxylic acid or derivative thereof; and (iii) an acrylic copolymer in particular weight ratios, together with tralopyril.
- the silyl ester copolymer contains monomers of triisopropylsilyl
- the silyl ester copolymer includes at least the monomers triisopropylsilyl methacrylate and a hydrophilic (meth)acrylate.
- the weight percentage of the triisopropylsilyl methacrylate monomer is in the range 5 to 80 wt%, preferably 30 to 75 wt%, such as 40 to 70 wt%, relative to the total weight of the silyl ester copolymer as a whole.
- (meth)acrylate monomer may be present in an amount of 2 to 50 wt%, such as 5 to 30 wt%, relative to the total weight of the silyl ester copolymer as a whole.
- silyl ester (meth)acrylate monomers hydrophilic (meth)acrylate monomers, and/or non-hydrophilic (meth)acrylate monomers may additionally be present as described herein.
- the silyl ester copolymer comprises as monomers:
- R 1 is hydrogen or methyl
- R 2 is a cyclic ether (such as oxolane, oxane, dioxolane, dioxane optionally alkyl substituted) and X is a C1-C4 alkylene; and/or a compound of Formula (II)
- R 3 is hydrogen or methyl
- R 4 is a C3 -C18 substituent with at least one oxygen or nitrogen atom, preferably at least one oxygen atom; and optionally
- R 5 is hydrogen or methyl
- R 6 is a C1-C8 hydrocarbyl
- the silyl ester copolymer includes at least the monomers triisopropylsilyl methacrylate (a) and at least one hydrophilic monomer (b).
- the wt% of a given monomer in the silyl ester copolymer is given, the wt% is relative to the sum total (weight) of each monomer present in the copolymer.
- the wt% of triisopropylsilyl methacrylate is calculated as [triisopropylsilyl methacrylate (a) (weight) /
- the copolymer preferably comprises >80 wt%, preferably >90 wt%, more preferably >95 wt%, especially >98 wt% of the combination of triisopropylsilyl methacrylate (a), hydrophilic (meth)acrylate monomer(s) (b) and non-hydrophilic (meth)acrylate monomer(s) (c).
- Component (a) is triisopropylsilyl methacrylate, which preferably forms 5 to 80 wt% of the copolymer, preferably 30 to 75 wt%, especially 40 to 70 wt%.
- Component (b) (total) preferably forms 2 to 50 wt% of the copolymer, preferably 3 to 40 wt% of the copolymer, especially 4 to 35 wt% of the copolymer, more especially 5 to 30 wt%. These wt% values refer to the total of component (b) monomers present.
- the ratio (a):(b) (weight/weight) is preferably in the range of 40:60 to 95:5, preferably in the range of 50:50 to 95:5, especially in the range of 55:45 to 93:7, most preferably in the range of 60:40 to 90: 10. It is preferred that the weight fraction of (a) in the copolymer is greater than that of component (b).
- the amount of (a)+(b) in the copolymer is preferably at most 95 wt%, such as at most 90 wt%, especially at most 85 wt%.
- the amount of (a)+(b) in the copolymer may be in the range of 30-95 wt% or 40-85 wt%. Hydrophilic (meth acrylate monomer(s) component (b)
- the silyl ester copolymer contains at least one monomer of Formula (I)
- R 1 is hydrogen or methyl
- R 2 is a cyclic ether (such as oxolane, oxane, dioxolane, dioxane optionally alkyl substituted)
- X is a C1-C4 alkylene, preferably a C1-C2 alkylene.
- the cyclic ether may contain a single oxygen atom in the ring or 2 or 3 oxygen atoms in the ring.
- the cyclic ether may contain a ring comprising 2 to 8 carbon atoms, such as 3 to 5 carbon atoms.
- the whole ring might comprise 4 to 8 atoms, such as 5 or 6 atoms.
- the cyclic ether ring may be substituted such as by one or more, such as one, C1-C6 alkyl group. That substituent group might be at any position on the ring including the position that binds to the X group.
- Suitable compounds of Formula (I) include tetrahydrofurfuryl acrylate, tetrahydrofurfuryl methacrylate, isopropylideneglycerol methacrylate,
- Formula (I) most preferably represents tetrahydrofurfuryl acrylate having the structure below:
- the copolymer may include one or more monomers of Formula (II):
- R 3 is hydrogen or methyl
- R 4 is a C3 -Cl 8 substituent containing at least one oxygen or nitrogen atom, preferably at least one oxygen atom.
- the term“hydrophilic (meth)acrylate” requires the R 4 group in Formula (II) to include at least one oxygen or nitrogen atom, preferably at least one oxygen atom.
- additional non- hydrophilic (meth)acrylate monomers of Formula (III) may also be present, in which the R 6 unit consists of C and H atoms only.
- the silyl ester copolymer contains at least one monomer of Formula (II) above, in which the R 4 group is of formula -(CH 2 CH 2 O) m -R 7 , where R 7 is a C1-C10 hydrocarbyl substituent, preferably a C1-C10 alkyl or a C6-C10 aryl substituent, and m is an integer in the range of 1 to 6, preferably 1 to 3.
- R 4 is of formula -(CH 2 CH 2 O) m -R 7 , where R 7 is an alkyl substituent, preferably methyl or ethyl, and m is an integer in the range of 1 to 3, preferably 1 or 2.
- the silyl ester copolymer includes one or more of 2- methoxyethyl methacrylate, 2-methoxyethyl acrylate, 2-ethoxyethyl methacrylate, 2- (2-ethoxyethoxy)ethyl methacrylate and 2-(2-ethoxyethoxy)ethyl acrylate.
- Particularly preferred monomer(s) (b) include 2-methoxyethyl acrylate, 2- methoxyethyl methacrylate, 2-ethoxyethyl methacrylate, 2-(2-ethoxyethoxy)ethyl acrylate, 2-(2-ethoxyethoxy)ethyl methacrylate, tetrahydrofurfuryl acrylate, and tetrahydrofurfuryl methacrylate.
- the silyl ester copolymer does not contain 2-(2- ethoxyethoxy)ethyl acrylate as a monomer.
- Formula (I) and Formula (II) defines a“polar”
- (meth)acrylate monomer or“hydrophilic” (meth)acrylate monomer.
- the use of these monomers with triisopropylsilyl methacrylate ensures the formation of a binder that has a controlled degradation.
- the silyl ester copolymer comprises a monomer of Formula (I) or a monomer of Formula (II). It is generally not preferred to have a monomer from both these formulae present.
- the silyl ester copolymer may include one or more additional non- hydrophilic (meth)acrylate monomers of Formula (III)
- R 5 is hydrogen or methyl
- R 6 is a C1-C8 hydrocarbyl substituent, preferably a C1-C8 alkyl substituent, most preferably methyl, ethyl, n-butyl or 2- ethylhexyl.
- Monomers according to Formula (III) are referred to as“non- hydrophilic” monomers herein.
- the silyl ester copolymer preferably includes at least one additional non-hydrophilic methacrylate and/or non-hydrophilic acrylate monomer.
- the sum of these non-hydrophilic (meth)acrylate monomers in the silyl ester copolymer is preferably at most 60 wt%, preferably no more than 55 wt%, such as in the range of 5 to 55 wt%, especially in the range of 10 to 50 wt%.
- the monomers triisopropylsilyl methacrylate (a), component (b) and any non-hydrophilic (meth)acrylate monomer(s) according to Formula (III) together form >80wt%, preferably >90 wt%, especially >95 wt% of the monomers in the silyl ester copolymer.
- the silyl ester copolymer includes one or more of the non-hydrophilic monomers methyl methacrylate and/or n-butyl acrylate. In all embodiments of the invention it is preferred that methyl methacrylate is included. Where present, methyl methacrylate is preferably present in an amount of 2 to 60 wt%, preferably 5 to 50 wt% of the copolymer. In a preferred embodiment triisopropylsilyl methacrylate (a), component (b) and methyl methacrylate together form >50 wt%, preferably >55 wt%, especially >60 wt% of the monomers in the silyl ester copolymer.
- n-butyl acrylate is preferably present in an amount of 1 to 30 wt%, especially 2 to 20 wt%.
- the silyl ester copolymer may include additional ethylenically unsaturated monomers.
- suitable ethylenically unsaturated monomers include styrene, vinyl acetate, triisopropylsilyl acrylate, 2- (trimethylsiloxy)ethyl methacrylate, zinc (meth)acrylate, zinc acetate (meth)acrylate and zinc neodecanoate (meth)acrylate.
- any additional ethylenically unsaturated monomer preferably forms no more than 20 wt% of the copolymer, preferably no more than 10 wt% of the copolymer.
- the silyl ester copolymer can be prepared using polymerization reactions known in the art.
- the silyl ester copolymer can be obtained by polymerizing a monomer mixture in the presence of a polymerization initiator by any of various methods such as solution polymerization, bulk polymerization, emulsion
- the copolymer is preferably diluted with an organic solvent to give a polymer solution having an appropriate viscosity. From this standpoint, it is desirable to employ solution polymerization.
- Suitable initiators for free-radical polymerization include azo compounds such as dimethyl 2,2’-azobis(2-methylpropionate), 2,2'-azobis(2- methylbutyronitrile), 2,2’-azobis(isobutyronitrile) and I,G- azobis(cyanocyclohexane); and peroxides such as tert- amyl peroxypivalate, tert- butyl peroxypivalate tert- amyl peroxy-2-ethylhexanoate, tert- butyl peroxy-2- ethylhexanoate, 1,1,3,3-tetramethylbutyl peroxy-2-ethylhexanoate, tert- butyl peroxydiethylacetate, tert-butyl peroxyiso butyrate, tert-butyl peroxyiso butyrate, tert-butyl pcroxybcnozatc, 1,1- di(tert
- organic solvent examples include aromatic hydrocarbons such as xylene, toluene, mesitylene; ketones such as methyl ethyl ketone, methyl isobutyl ketone, methyl amyl ketone, methyl isoamyl ketone, diisobutyl ketone,
- esters such as butyl acetate, tert-butyl acetate, amyl acetate, propyl prop
- the silyl ester copolymer may be a random copolymer, an alternate copolymer, a gradient copolymer or block copolymer.
- the copolymer is preferably a random copolymer.
- the thus-obtained polymer containing organosilyl ester groups preferably has a weight-average molecular weight (Mw) from 5,000 to 100,000, preferably from 15,000 to 80,000, more preferably from 20,000 to 60,000. Mw is measured as described in the examples section.
- the copolymer preferably has a glass transition temperature (Tg) of at least 15 °C, preferably at least 20 °C, such as at least 25 °C, all values being measured according to the Tg test described in the examples section. Values less than 80 °C are preferred, such as less than 70 °C, e.g. less than 60 °C.
- Tg glass transition temperature
- the silyl ester copolymer may be provided as a polymer solution, such as a xylene solution.
- the polymer solution is desirably regulated to have a solid content from 30 to 90 % by weight, preferably from 40 to 85 % by weight, more preferably from 45 to 75 % by weight.
- the amount of silyl ester copolymer present in the compositions of the invention is 30 to 80 wt% (dry solids), preferably 30 to 75 wt%, more preferably 35 to 70 wt% (dry solids), even more preferably 40 to 60 wt% (dry solids), based on the total weight of the binder (A).
- the final antifouling coating composition of the invention preferably comprises 2 to 40 wt% (dry solids) of the silyl ester copolymer, such as 3 to 30 wt% (dry solids), in particular 5 to 20 wt% (dry solids) based on the total coating composition.
- the antifouling coating compositions of the present invention comprise a monocarboxylic acid or derivative thereof
- the monocarboxylic acid present in the antifouling coating composition of the present invention preferably comprises 5 to 50 carbon atoms, more preferably 10 to 40 carbon atoms and still more preferably 12 to 25 carbon atoms.
- the monocarboxylic acid present in the antifouling coating composition of the present invention is preferably selected from a resin acid, a derivative of a resin acid, C6-C20 cyclic monocarboxylic acid, C5-C24 acyclic aliphatic monocarboxylic acid, C7-C20 aromatic monocarboxylic acid and mixtures thereof.
- Derivatives of monocarboxylic acid include metal salts of monocarboxylic acid, such as alkali metal carboxylate, alkaline earth metal carboxylate (e.g. calcium carboxylate, magnesium carboxylate) and transition metal carboxylate (e.g. zinc carboxylate, copper carboxylate).
- alkali metal carboxylate alkaline earth metal carboxylate (e.g. calcium carboxylate, magnesium carboxylate)
- transition metal carboxylate e.g. zinc carboxylate, copper carboxylate.
- the metal carboxylate is a transition metal carboxylate, particularly preferably the metal carboxylate is a zinc
- the metal carboxylate may be generated in situ in the antifouling coating composition.
- resin acids include abietic acid, neoabietic acid, dehydroabietic acid, palustric acid, levopimaric acid, pimaric acid, isopimaric acid, sandaracopimaric acid, communic acid and mercusic acid, secodehydroabietic acid.
- Resin acids are also referred to as rosin acids.
- sources of resin acids are gum rosin, wood rosin and tall oil rosin. Gum rosin, also referred to as colophony and colophonium, is particularly preferred.
- Preferred rosins are those comprising more than 85 % resin acids and still more preferably more than 90 % resin acids.
- rosin Commercial grades of rosin are often classified according to its colour by designation of letters on a colour scale XC (lightest), XB, XA, X, WW, WG, N, M, K, I, H, G, F, E, D (darkest) as specified in ASTM D509.
- Preferred colour grades for the compositions of the invention are X, WW, WG, N, M, K, I, and still more preferably WW.
- Commercial grades of rosin typically have an acid value from 155 to 180 mg KOH/g as specified in ASTM D465.
- Preferred rosin for the compositions of the invention has an acid value from 155 to 180 mg KOH/g, more preferred 160 to 175 mg KOH/g, even more preferred 160 to 170 mg KOH/g.
- rosin typically have a softening point (Ring & Ball) of 70 °C to 80 °C as specified in ASTM E28.
- Preferred rosin for the compositions of the invention has a softening point of 70 °C to 80 °C, more preferred 75 °C to 80 °C
- resin acid derivatives include partly
- dihydroabietic acids dihydropimaric acids and tetrahydroabietic acids.
- C6-C20 cyclic monocarboxylic acids include naphthenic acid, 1 ,4-dimethyl-5-(3-methyl-2-butenyl)-3-cyclohexen- 1 -yl-carboxylic acid, 1,3-dimethyl-2-(3-methyl-2-butenyl)-3-cyclo hex en-l -yl-carboxylic acid, 1,2,3- trimethyl-5-(l -methyl-2-propenyl)-3-cyclohexen- 1 -yl-carboxylic acid, 1 ,4,5- trimethyl-2-(2-methyl-2-propenyl)-3-cyclohexen- 1 -yl-carboxylic acid, 1 ,4,5- trimethyl-2-(2-methyl- 1 -propenyl)-3-cyclohexen- 1 -yl-carboxylic acid, 1,5,6- trimethyl-3 -(2-methyl- 1 -propenyl)-4-cyclohexen- 1
- C5-C24 acyclic aliphatic monocarboxylic acids include VersaticTM acids, neodecanoic acid, 2,2,3,5-tetramethylhexanoic acid, 2,4- dimethyl-2-isopropylpentanoic acid, 2,5-dimethyl-2-ethylhexanoic acid, 2,2- dimethyloctanoic acid, 2,2-diethylhexanoic acid, pivalic acid, 2,2-dimethylpropionic acid, trimethylacetic acid, neopentanoic acid, 2-ethylhexanoic acid, isononanoic acid, 3,5,5-trimethylhexanoic acid, isopalmitic acid, isostearic acid, 16- methylheptadecanoic acid and l2,l5-dimethylhexadecanoic acid.
- VersaticTM acids neodecanoic acid, 2,2,3,5-tetramethylhexanoic acid
- the acyclic aliphatic monocarboxylic acid is preferably selected from liquid, acyclic C10-C24 monocarboxylic acids or liquid, branched C10-C24 monocarboxylic acids. It will be appreciated that many of the acyclic C10-C24 monocarboxylic acids may be derived from natural sources, in which case in isolated form they typically exist as a mixture of acids of differing chain lengths with varying degree of branching.
- the monocarboxylic acid is gum rosin, derivatives of gum rosin, acyclic C10-C24 monocarboxylic acids, C6-C20 cyclic monocarboxylic acids or mixtures thereof.
- a mixture of acid preferably contains at least one resin acid, gum rosin or derivative of gum rosin. Gum rosin is most preferred.
- the derivative of the monocarboxylic acid is not a metal carboxylate.
- the amount of monocarboxylic acid present in the compositions of the invention is 20 to 55 wt% (dry solids), preferably 25 to 51 wt% (dry solids), more preferably 30-50 wt% (dry solids), based on the total weight of the binder (A).
- the final antifouling coating composition of the invention preferably comprises 2 to 30 wt% (dry solids) of the monocarboxylic acid, such as 4 to 25 wt% (dry solids), in particular 5 to 20 wt% (dry solids) based on the total coating composition.
- the term“acrylic copolymer” refers to copolymers comprising at least one monomer based on acrylic acid, methacrylic acid, esters of acrylic acid and esters of methacrylic acid. It is a requirement that the copolymer (iii) is different to the copolymer (i) in the binder (A) of the invention.
- the acrylic copolymer has a Tg below 25 °C, preferably below 10 °C, more preferred below 0 °C, even more preferred below -10°C, all values being measured according to the Tg test described in the examples section. It is envisaged that the use of an acrylic copolymer having a glass transition temperature (Tg) of less than 25 °C reduces the viscosity of the eventual antifouling coating composition and therefore reduces the solvent content that might be required.
- the acrylic copolymer preferably contains no hydrophilic monomers, except for monomers having an acid functionality.
- the acrylic copolymer contains (meth)acrylic acid units, more preferred having acid number below 60 mg KOH/g polymer, more preferred below 40 mg KOH/g polymer, even more preferred below 25 mg KOH/g polymer.
- the acid number is above 2 mg KOH/g polymer, such as above 5 mg KOH/g polymer.
- the acid number is measured as described in the examples section.
- the acrylic copolymer comprises 0.50-10 wt% of a carboxylic acid-containing monomer, based on the total weight of the acrylic copolymer.
- the acrylic copolymer comprises as monomers:
- R 8 is hydrogen or methyl, and R 9 is a C1-C20 hydrocarbyl substituent
- the combination of monomers defined under i. and ii. may make up at least 80 wt% of the acrylic copolymer such as at least 85 wt%, preferably at least 90 wt%, more preferably at least 95 wt%.
- the combination of monomers defined under i. and ii. represent up to 95 wt% of the acrylic copolymer, such as up to 99 wt% of the acrylic copolymer.
- the“combination of monomers defined under i. and ii.” includes the possibility of having two or more monomers of Formula (IV) or two or more carboxylic acid-containing monomers.
- the acrylic copolymer preferably contains less than 10 wt%, preferably less than 5 wt%, preferably less than 2 wt% of any monomer other than the monomers of Formula (IV) and carboxylic acid-containing monomer as described in i. and ii. above.
- components i. and ii. make up the entirety of the monomer components of the acrylic copolymer.
- the acrylic copolymer does not comprise a hydro lysable monomer, such as a silyl ester monomer.
- the acrylic copolymer is non- hydrolysable.
- the acrylic copolymer has a weight average molecular weight (Mw) of 10,000 to 50,000 g/mol, preferably 15,000 to 45,000.
- the acrylic copolymer may have an acid value of 2 to 60 mg KOH/g polymer as measured according to the acid value test described in the examples section, such as 5 to 40 mg KOH/g polymer.
- the binder (A) comprises 5 to 20 wt% (dry solids) of the acrylic copolymer, preferably 7 to 15 wt% (dry solids), e.g. 10 wt%
- the antifouling composition preferably comprises 1.0 to 15 wt% (dry solids) of the acrylic copolymer, preferably 1.2 to 10 wt% (dry solids), more preferably 1.5 to 8 wt% (dry solids) based on the total coating composition.
- the (meth)acrylate monomer to be used in the acrylic copolymer is preferably of Formula (IV):
- R 8 is hydrogen or methyl
- R 9 is a C1-C20 hydrocarbyl, preferably a Cl -8 alkyl substituent, most preferably methyl, ethyl, n-propyl, n-butyl or 2-ethylhexyl.
- Particularly preferred R 9 groups are methyl, n-butyl, and 2- ethylhexyl.
- Monomers according to Formula (IV) are referred to as“non-hydrophilic” monomers herein.
- the acrylic copolymer comprises at least one (meth)acrylate monomer of Formula (IV) selected from methyl methacrylate, ethyl acrylate, n-butyl acrylate, n-butyl methacrylate, 2-ethylhexyl acrylate and 2- ethylhexyl methacrylate.
- the acrylic copolymer comprises at least two different monomers of Formula (IV).
- the acrylic copolymer comprises methyl methacrylate as one monomer and at least one other monomer of Formula (IV). In a further particular embodiment, the acrylic copolymer comprises at least methyl methacrylate and n-butyl (meth)acrylate. Where one or more (meth)acrylate monomers of Formula (IV) are present, the weight percentage of the sum of these (meth)acrylate monomers in the acrylic copolymer is preferably at most 99.5 wt%, such as at most 99.2 wt%, such as at most 99.0 wt%, such as at most 98.5 wt%, such as 98.0 wt% based on the total weight of the acrylic copolymer.
- the weight percentage of the sum of these (meth)acrylate monomers in the acrylic copolymer is preferably at least 80 wt%, such as at least 85 wt%, such as at least 90 wt%, such as at least 92 wt% based on the total weight of the acrylic copolymer.
- methyl methacrylate is preferably present in an amount of 1.0 to 50 wt% of the acrylic copolymer, preferably 1.5 to 30 wt%, more preferably 1.5 to 25 wt%.
- n-butyl acrylate is preferably present in an amount of 50 to 99 wt% of the acrylic copolymer, preferably 55 to 98 wt%, more preferably 65 to 97 wt%, such as 70 to 95 wt%.
- Carboxylic acid-containing monomer ii The carboxylic acid-containing monomer(s) to be used in the acrylic copolymer help to provide improved compatibility of the acrylic copolymer in the coating film.
- the carboxylic acid-containing monomer(s) are interchangeably referred to as acidic monomer(s) herein. It has been found that below the optimum range of acidic monomer content, the acrylic copolymer is prone to migrate in the coating film, whereas above the optimum range of acidic monomer content acrylic copolymers with high viscosities are obtained. High viscosity of the acrylic copolymer means that higher amounts of solvent are needed for preparation and application of the paint. This is unwanted due to strict VOC regulations.
- the acidic monomer is present in an amount of 0.5-10 wt% based on the weight of the acrylic copolymer.
- the carboxylic acid-containing monomer is present in an amount of 0.5-8.0 wt%, such as 0.7- 8.6 wt%, such as 1.0-7.5 wt%, such as 1.2-7.0 wt%, such as 1.3-6.5 wt%, such as 1.4-6.0 wt%, based on the weight of the acrylic copolymer.
- carboxylic acid containing monomers examples include acrylic acid, methacrylic acid, 2-carboxyethyl acrylate, 2-carboxymethyl methacrylate, mono-2- (methacryloyloxy)ethyl maleate and mono-2-(methacryloyloxy)ethyl succinate.
- the carboxylic acid-containing monomer is acrylic acid or methacrylic acid, more preferably methacrylic acid. A combination of both acrylic acid and methacrylic acid may be used.
- the carboxylic acid-containing acrylic copolymer is preferably free of any N-vinyl lactam monomer. In particular, the absence of N- vinyl pyrrolidone is preferred.
- the acrylic copolymer may be prepared using polymerization reactions known in the art.
- Acrylic polymers are preferably prepared using addition polymerization or chain growth polymerization.
- the polymer may, for example, be obtained by polymerizing a monomer mixture in the presence of a polymerization initiator and optionally a chain transfer agent by any of various methods such as solution polymerization, bulk polymerization, emulsion polymerization, dispersion polymerization and suspension polymerization in a conventional way or by controlled polymerization techniques.
- the polymer is preferably diluted with an organic solvent to give a polymer solution having an appropriate viscosity. From this standpoint, it is desirable to employ solution polymerization.
- Suitable initiators for free-radical polymerization include azo compounds such as dimethyl 2,2’-azobis(2-methylpropionate), 2,2'-azobis(2- methylbutyronitrile), 2,2’-azobis(isobutyronitrile) and 1,1'
- azobis(cyanocyclohexane); and peroxides such as as tert- amyl peroxypivalate, tert- butyl peroxypivalate tert- amyl peroxy-2-ethylhexanoate, tert- butyl peroxy-2- ethylhexanoate, l,l,3,3-tetramethylbutyl peroxy-2-ethylhexanoate, tert- butyl peroxydiethylacetate, tert-butyl peroxyiso butyrate, tert-butyl pcroxybcnozatc, 1,1- di( tert-amyl peroxy)cyclohexane, ert-amylpcroxy 2-ethylhexyl carbonate, tert- butylperoxy isopropyl carbonate, tert-butylpcroxy 2-ethylhexyl carbonate, polyether
- organic solvent examples include aromatic hydrocarbons such as xylene, toluene, mesitylene; ketones such as methyl ethyl ketone, methyl isobutyl ketone, methyl amyl ketone, methyl isoamyl ketone, diisobutyl ketone,
- cyclopentanone cyclohexanone
- esters such as butyl acetate, tert-butyl acetate, amyl acetate, ethylene glycol methyl ether acetate, propyl propionate, n-butyl propionate, isobutyl isobutyrate
- ethers such as ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, dibutyl ether, dioxane, tetrahydrofuran, alcohols such as n-butanol, isobutanol, methyl isobutyl carbinol, benzyl alcohol; ether alcohols such as butoxyethanol, l-methoxy-2-propanol; terpenes such as limonene; aliphatic hydrocarbons such as white spirit; and optionally a mixture of two or more solvents. These compounds are used alone or as a mixture of two or more thereof. Preferred are mixtures of aromatic hydrocarbons
- the acrylic copolymer may be a random copolymer, an alternating copolymer, a gradient copolymer or a block copolymer.
- the acrylic copolymer is preferably a random copolymer.
- an additional binder can be used to adjust the properties of the antifouling coating film.
- binders that can be used include:
- hydrophilic copolymers such as poly(N-vinyl pyrrolidone) copolymers and polyethylene glycol) copolymers;
- vinyl ether polymers and copolymers such as poly(methyl vinyl ether), poly(ethyl vinyl ether), poly(isobutyl vinyl ether), poly(vinyl chloride-co-isobutyl vinyl ether);
- (meth)acrylic homopolymers and copolymers such as poly(n-butyl acrylate) and poly(n-butyl acrylate-co-isobutyl vinyl ether);
- polymeric plasticizers from any of the polymer groups specified above.
- polymeric plasticizer refers to polymers having a glass transition temperature (Tg) below 25°C.
- binders that may be present in the antifouling coating composition of the invention include:
- silyl ester (meth)acrylate copolymers such as copolymers comprising triisopropylsilyl acrylate
- metal (meth)acrylate copolymers such as copolymers comprising zinc (meth)acrylate, zinc hydroxide (meth)acrylate, zinc neodecanoate (meth)acrylate or zinc oleate (meth)acrylate;
- saturated aliphatic polyesters such as poly(lactic acid), poly(glycolic acid), poly(2-hydroxybutyric acid), poly(3-hydroxybutyric acid), poly(4-hydroxyvaleric acid), polycaprolactone and aliphatic polyester copolymer containing two or more of the units selected from the above mentioned units;
- esters of rosin and hydrogenated rosin such as methyl esters, glycerol esters, polyethylene glycol) esters, pcntacrythritol esters, preferred are esters of gum rosin and hydrogenated gum rosin;
- dimerized and polymerized rosin dimerized and polymerized rosin; alkyd resins and modified alkyd resins;
- hydrocarbon resin such as hydrocarbon resin formed only from the polymerisation of at least one monomer selected from a C5 aliphatic monomer, a C9 aromatic monomer, an indene coumarone monomer, or a terpene or mixtures thereof.
- the weight ratio of binder (A):binder may range from 70:30 to 99: 1, preferably from 75:25 to 95:5, especially 80:20 to 90:10.
- the antifouling coating composition additionally comprises a compound capable of preventing or removing marine fouling on or from a surface.
- a compound capable of preventing or removing marine fouling on or from a surface 4-bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-lH-pyrrole-3-carbonitrile [tralopyril], having the structure below, must be present.
- Example of commercial available tralopyril include Econea from Janssen PMP.
- antifouling agent In addition to this biocide, other antifouling compounds can be present.
- antifouling agent antifoulant, biocide and toxicant are used in the industry to describe known compounds that act to prevent marine fouling on a surface.
- the antifouling agents of the invention are marine antifouling agents.
- Preferred additional biologically active agents are zinc pyrithione, copper pyrithionc, zinc ethylenebis(dithiocarbamate) [zineb], 2-(tert-butylamino)-4- (cyclopropylamino)-6-(methylthio)-l,3,5-triazine [cubutryne], 4,5-dichloro-2-n- octyl-4-isothiazolin-3-one [DCOIT], N-dichlorofluoromethylthio-N',N'-dimethyl-N- phenylsulfamide [dichlofluanid], N-dichlorofluoromethylthio-N',N'-dimethyl-N-p- tolylsulfamide [tolylfluanid], triphenylborane pyridine [TPBP] and 4-[l-(2,3- dimethylphenyl)ethyl] - 1 H-imidazo le [medetomidine]
- the composition does not comprise 4-[l-(2,3- dimethylphenyl)ethyl] - 1 H-imidazo le [medetomidine] .
- a mixture of biocides can be used as is known in the art as different biocides operate against different marine fouling organisms.
- More preferred is a mixture of biocides active against marine invertebrates, such as barnacles, tubeworms, bryozoans and hydroids; plants, such as seaweed, algae and diatoms; and bacteria.
- the most preferred option is a combination of tralopyril and one or more selected biocides selected from zinc pyrithione, copper pyrithione, zineb, dichlofluanid, and 4,5-dichloro-2-octyl-4- isothiazo lin-3 -one .
- the composition comprises less than 0.5 wt% of an inorganic copper biocide, preferably less than 0.2 wt% of an inorganic copper biocide, even more preferably less than 0.1 wt% of an inorganic copper biocide, relative to the total weight of the composition as a whole. Most preferably, the composition is free of an inorganic copper biocide.
- composition of the invention comprises copper pyrithione, an organometallic copper compound.
- the composition is free of any copper based biocides.
- the combined amounts of biocides may form up to 20 wt% of the coating composition, such as 0.5 to 15 wt%, e.g. 1.0 to 12 wt%. It will be appreciated that the amount of biocide will vary depending on the end use and the biocide used.
- biocides may be encapsulated or adsorbed on an inert carrier or bonded to other materials for controlled release. These percentages refer to the amount of active biocide present and not therefore to any carrier used.
- Other components may be encapsulated or adsorbed on an inert carrier or bonded to other materials for controlled release. These percentages refer to the amount of active biocide present and not therefore to any carrier used.
- the antifouling coating composition according to the present invention may optionally further comprise one or more components selected among other binders, inorganic or organic pigments, extenders and fillers, additives, solvents and thinners.
- the pigments may be inorganic pigments, organic pigments or a mixture thereof.
- Inorganic pigments are preferred.
- examples of inorganic pigments include titanium dioxide, red iron oxide, yellow iron oxide, black iron oxide, zinc oxide, zinc sulfide, lithopone and graphite.
- examples of organic pigments include carbon black, phthalocyanine blue, phthalocyanine green, napthol red and
- Pigments may optionally be surface treated to be more easily dispersed in the paint composition.
- extenders and fillers are minerals such as dolomite, plastorite, calcite, quartz, barite, magnesite, silica, nepheline syenite, wollastonite, talc, chlorite, mica, kaolin, pyrophyllite and feldspar; synthetic inorganic compounds such as calcium carbonate, magnesium carbonate, barium sulphate, calcium silicate and silica; polymeric and inorganic microspheres such as uncoated or coated hollow and solid glass beads, uncoated or coated hollow and solid ceramic beads, porous and compact beads of polymeric materials such as poly(methyl methacrylate), poly(methyl methacrylate-co-ethylene glycol dimethacrylate), poly( styrene-co- ethylene glycol dimethacrylate), poly(styrene-co-divinylbenzene), polystyrene, poly(vinyl chloride).
- minerals such as dolomite, plastorite, cal
- the total amount of extender and/or pigment present in the compositions of the invention is 2-60 wt%, more preferably 5-50 wt% and still more preferably 7-45 wt%, based on the total weight of the composition.
- the extender and pigment content will vary depending on the particle size distribution, the particle shape, the surface morphology, the particle surface-resin affinity, the other components present and the end use of the coating composition. Examples of additives that can be added to an antifouling coating
- compositions are reinforcing agents, rheology modifiers, wetting and dispersing agents, defoamers and plasticizers.
- Fibres include natural and synthetic inorganic fibres and natural and synthetic organic fibres e.g. as described in WO 00/77102.
- Representative examples of fibres include mineral-glass fibres, wollastonite fibres, montmorillonite fibres, tobermorite fibres, atapulgite fibres, calcined bauxite fibres, volcanic rock fibres, bauxite fibres, rockwool fibres, and processed mineral fibres from mineral wool.
- the fibres have an average length of 25 to 2,000 ⁇ m and an average thickness of 1 to 50 ⁇ m with a ratio between the average length and the average thickness of at least 5.
- reinforcing agents are present in the compositions of the invention in an amount of 0-20 wt%, more preferably 0.5-15 wt% and still more preferably 1-10 wt%, based on the total weight of the composition.
- rheology modifiers include thixotropic agents, thickening agents and anti-settling agents.
- Representative examples of rheology modifiers are silicas such as fumed silicas, organo-modified clays, amide waxes, polyamide waxes, amide derivatives, polyethylene waxes, oxidised polyethylene waxes, hydrogenated castor oil wax, ethyl cellulose, aluminium stearates and mixtures thereof.
- Rheology modifiers that need activation may be added to the coating composition as is and activated during the paint production process or they can be added to the coating composition in a pre-activated form, e.g. solvent paste.
- rheology modifiers are each present in the composition of the invention in an amount of 0-5.0 wt%, more preferably 0.2-3.0 wt% and still more preferably 0.5-2.0 wt%, based on the total weight of the coating composition.
- plasticizers are polymeric plasticizers, chlorinated paraffins, phthalates, phosphate esters, sulphonamides, adipates, epoxidised vegetable oils and sucrose acetate isobutyrate.
- plasticizers are present in the compositions of the invention in an amount of 0-10 wt%, more preferably 0.5-7 wt% and still more preferably 1-5 wt%, based on the total weight of the coating composition.
- the dehydrating agent is preferably a compound which removes moisture and water from the coating composition. It is also referred to as water scavenger or drying agent.
- the dehydrating agents may be hygroscopic materials that absorb water or bind water as crystal water. These are often referred to as desiccants. Examples of such compounds include anhydrous calcium sulphate, calcium sulphate hemihydrate, anhydrous magnesium sulphate, anhydrous sodium sulphate, anhydrous zinc sulphate, molecular sieves and zeolites.
- the dehydrating agents may also be compounds that chemically react with water. Examples of dehydrating agents that react with water include orthoesters such as trimethyl orthoformate, triethyl orthoformate, tripropyl orthoformate, triisopropyl
- orthoformate tributyl orthoformate, trimethyl orthoacetate, triethyl orthoacetate tributyl orthoacetate and triethyl orthopropionate; ketals; acetals; enolethers;
- orthoborates such as trimethyl borate, triethyl borate, tripropyl borate, triisopropyl borate, tributyl borate and tri- tert-butyl borate; organosilanes such as
- trimethoxymethylsilane triethoxymethylsilane, tetraethoxysilane
- phenyltrimetoxysilane vinyltrimethoxysilane, vinyltriethoxysilane and ethyl polysilicate; and isocyanates, such as p-toluenesulfonyl isocyanate.
- the preferred dehydrating agents are organosilanes, such as
- tetraethoxysilane and inorganic desiccants.
- organosilane is especially preferred.
- Stabilizers are preferably acid scavengers.
- stabilizers are carbodiimide compounds, such as bis(2,6-diisopropylphenyl)carbodiimide, bis(2- methylphenyl)carbodiimide, 1 ,3-di-/ -tolylcarbodiimidc and others as described in W02014064049.
- the dehydrating agents and stabilizers are each present in the compositions of the invention in an amount of 0-5 wt%, more preferably 0.5-2.5 wt% and still more preferably 1.0-2.0 wt%, based on the total weight of the composition.
- the antifouling composition contains a solvent.
- This solvent is preferably volatile and is preferably organic.
- organic solvents and thinners are aromatic hydrocarbons such as xylene, toluene, mesitylene; ketones such as methyl ethyl ketone, methyl propyl ketone, methyl isobutyl ketone, methyl isoamyl ketone, methyl amyl ketone, diisobutyl ketone, cyclopentanone, cyclohexanone; esters such as butyl acetate, tert- butyl acetate, amyl acetate, isoamyl acetate, propyl propionate, n-butyl propionate, isobutyl isobutyrate; ether esters such as ethylene glycol methyl ether acetate, ethyl 3-ethoxypropionate; ethers such as ethylene glycol dimethyl ether, diethylene glycol
- Preferred solvents are aromatic solvents, especially xylene and mixtures of aromatic hydrocarbons.
- the amount of solvent is preferably as low as possible.
- the solvent content may be up to 45 wt% of the composition, preferably up to 40 wt% of the
- composition such as up to 35 wt% but may be as low as 15 wt% or less, e.g. 10 wt% or less.
- some raw materials comprise solvent and contribute to the total solvent content as specified above and that the solvent content will vary depending on the other components present and the end use of the coating composition.
- the coating can be dispersed in an organic non- solvent for the film- forming components in the coating composition or in an aqueous dispersion.
- the antifouling coating composition of the invention should preferably have solids content above 40 vol%, e.g. above 45 vol%, such as above 50 vol%, preferably above 55 vol%.
- the antifouling coating composition should have a content of volatile organic compounds (VOC) below 500 g/L, preferably below 420 g/L, more preferably below 400 g/L, e.g. below 380 g/L.
- VOC content can be calculated (ASTM D5201-01) or measured, e.g. as described in US EPA Method 24 or ISO 11890-2, preferably measured.
- the antifouling coating composition of the invention can be applied to a whole or part of any object surface which is subject to fouling.
- the surface may be permanently or intermittently underwater (e.g. through tide movement, different cargo loading or swell).
- the object surface will typically be the hull of a vessel or surface of a fixed marine object such as an oil platform or buoy.
- Application of the coating composition can be accomplished by any convenient means, e.g. via painting (e.g. with brush or roller) or spraying the coating onto the object.
- the surface will need to be separated from the seawater to allow coating.
- the application of the coating can be achieved as conventionally known in the art.
- the surface of the object is not protected solely by a single coat of antifouling.
- the antifouling coating can be applied directly to an existing coating system.
- a coating system may comprise several layers of paint of different generic types (e.g. epoxy, polyester, vinyl or acrylic or mixtures thereof).
- an uncoated surface e.g. steel, aluminium, plastic, composite, glass fiber or carbon fiber
- the full coating system will typically comprise one or two layers of an anticorrosive coating (e.g. curable epoxy coating or curable modified epoxy coating), one layer of tie-coat (e.g. curable modified epoxy coating or physical drying vinyl coating) and one or two layers of antifouling paint.
- an anticorrosive coating e.g. curable epoxy coating or curable modified epoxy coating
- tie-coat e.g. curable modified epoxy coating or physical drying vinyl coating
- antifouling paint e.g. curable modified epoxy coating or physical drying vinyl coating
- further layers of antifouling paint may be applied. If the surface is a clean and intact antifouling coating from a previous application, the new antifouling paint can be applied
- the viscosity of the polymers was determined in accordance with ASTM D2196 Test Method A using a Brookfield DV-I viscometer with LV-2 or LV-4 spindle at 12 rpm.
- the polymer solutions were tempered to 23.0 °C ⁇ 0.5 °C before the measurements. Determination of non-volatile matter content of the polymer solutions
- the non-volatile matter content in the polymer solutions was determined in accordance with ISO 3251. A test sample of 0.5 g ⁇ 0.1 g was taken out and dried in a ventilated oven at 150 °C for 30 minutes. The weight of the residual material was considered to be the non-volatile matter (NVM). The non-volatile matter content is expressed in weight percent. The value given is the average of three parallel measurements.
- the polymers were characterised by Gel Permeation Chromatography (GPC) measurement.
- the molecular weight distribution (MWD) was determined using a Malvern Omnisec Resolve and Reveal system with two PLgel 5 ⁇ m Mixed-D columns from Agilent in series, tetrahydrofuran (THF) as eluent at a constant flow rate of 1 ml/min and with a refractive index (RI) detector.
- the columns were calibrated using narrow polystyrene standards Polystyrene Medium EasiVials (4 ml) Red, Yellow and Green from Agilent.
- the column oven temperature and the detector oven temperature were 35 °C.
- the sample injection volume was 100 m ⁇ .
- the data were processed using Omnisec 5.1 software from Malvern.
- Samples were prepared by dissolving an amount of polymer solution corresponding to 25 mg dry polymer in 5 ml THF. The samples were kept for minimum 3 hours at room temperature prior to sampling for the GPC measurements. Before analysis the samples were filtered through 0.45 ⁇ m Nylon filters. The weight-average molecular weight (Mw) and the polydispersity index (PDI), given as Mw/Mn, are reported in the tables.
- Mw weight-average molecular weight
- PDI polydispersity index
- the glass transition temperature (Tg) was obtained by Differential Scanning Calorimetry (DSC) measurements.
- DSC measurements were performed on a TA Instruments DSC Q200. Samples were prepared by transfer of a small amount of polymer solution, corresponding to approx. 10 mg dry polymer material, to an aluminium pan and dry the samples for minimum 16-20 h at 50 °C with subsequent 3 h at 150 °C in a ventilated heating cabinet.
- the measurement was performed by running a heat-cool-heat procedure, within a temperature range from -80 °C to 120 °C, with a heating rate of 10 °C/min and cooling rate of 10 °C/min and using an empty pan as reference.
- the data were processed using Universal Analysis software from TA Instruments. The inflection point of the glass transition range, as defined in ASTM E1356-08, of the second heating is reported as the Tg of the polymers.
- the acid value of the polymers was determined according to the procedure described in ISO 2114:2000 Method A. A weighed quantity of the polymer solution was dissolved in Jotun Thinner No. 17. Phenolphthalein was added as colour indicator and the solution was titrated with 0.1 M KOH solution in ethanol until a red colouration appeared and was stable for 10-15 s while the solution was stirred. The acid value for the dry polymers were calculated based on measured non-volatile matter of the tested polymer solution. The reported acid value is the average value of three parallel measurements.
- Copolymer solution S8 was prepared using the process described for copolymer solution Sl above with a reaction temperature of 95°C and the amount of ingredients given in Table 1 A.
- a quantity of solvent was charged to a temperature-controlled reaction vessel equipped with a stirrer, a condenser, a nitrogen inlet and a feed inlet.
- the reaction vessel was heated and maintained at the reaction temperature of 95°C.
- a pre-mix of monomers, initiator and solvent was prepared. The pre-mix was charged to the reaction vessel at a constant rate over 2 hours under a nitrogen atmosphere. After further 1 hour reaction, post-addition of a boost initiator solution was added. The reaction vessel was maintained at the reaction temperature for a further 1.5 hours. The reactor was then heated to 105 °C and kept at this temperature for 1 hour.
- the copolymer solution had the following properties:
- copolymer solutions was prepared using the procedure described for copolymer solution Al with a reaction temperature of 95°C and with the amount of ingredients in the reactor charges, feed charges and boost charges as given in Table 1B.
- Thinning of copolymer A3 was done prior to the cooling of the polymer solution to room temperature.
- the zinc rosinate solution had a non-volatile matter of 64.1 wt%.
- Table 1 A Silyl copolymer ingredients and properties (amounts given in parts by weight).
- the mixture was dispersed in the presence of glass beads (approx. 2 mm in diameter) in a paint can of 250 ml using a vibrational shaker for 15 minutes. The glass beads were filtered out before testing.
- the viscosity of the antifouling paint composition was determined in accordance with ISO 2884-1 : 1999 using a digital Cone and Plate viscometer set at a temperature of 23 °C, working at a shear rate of 10 000 s -1 and providing viscosity measurement range of 0-10 P. The result is given as the average of three measurements.
- the volatile organic compound (VOC) content of the antifouling coating is the volatile organic compound (VOC) content of the antifouling coating
- composition was calculated in accordance with ASTM D5201.
- the hardness of the coating film was determined using a pendulum hardness tester.
- Each of the antifouling coating compositions was applied to a transparent glass plate (100 c 200> ⁇ 2 mm) using a film applicator with 300 ⁇ m gap size.
- the coating films were dried at 23°C and 50% relative humidity for 1 week and then dried at 50°C for 72 hours in a ventilated heating cabinet.
- the coating film hardness of the dry coating film was measured at a temperature of 23°C and 50% relative humidity using an Erichsen 299/300 pendulum hardness tester. The hardness is quantified as the number of pendulum swings to damp the amplitude from 6° to 3°. A higher number of swings indicates a higher hardness of the coating. The result is reported as the average of three parallel measurements on coating films after forced drying in the heating cabinet.
- PVC panels were coated with Safeguard Plus (two-component polyamide cured vinyl epoxy based coating, manufactured by Chokwang Jotun Ltd., Korea) using airless spray.
- the panels were dried and cured according to the product application guide.
- the antifouling coatings were applied on the cured, pre-coated panels using a film applicator with gap size of 800 ⁇ m.
- the applied coating films were dried for 72 h at 52 °C before immersion in seawater at 40 °C. At regular intervals, the panels are taken out and evaluated after drying under ambient conditions for 24 h and drying at 52 °C for 24 h.
- the panels were assessed for cracking visually and under 10 x magnifications and rated as described in ISO 4628-4:2005. The density and the size of the cracks were reported. The panels were then re-immersed. The result after 6 months of exposure is reported.
- the polishing rate was determined by measuring the reduction in film thickness of a coating film over time.
- PVC discs were used.
- the coating compositions were applied as radial stripes on the disc using a film applicator with a gap size of 600 ⁇ m.
- the thicknesses of the dry coating films were measured by a surface profiler.
- the initial dry film thickness will depend on the solids content of the applied antifouling coating composition and the speed of application. Typical initial dry film thickness for the tested coatings was 235 ⁇ 30 ⁇ m.
- the PVC discs were mounted on a shaft and rotated in a container in which seawater was flowing through. Natural seawater which has been filtered and temperature- adjusted to 25 °C ⁇ 2 °C was used. The speed of the rotated shaft provided an average simulated speed of 16 knots on the disc.
- the PVC discs were taken out at regular intervals for measuring the film thickness. The discs were rinsed and allowed to dry overnight at room temperature before measuring the film thicknesses. The results were given as film consumption, i.e. the difference between the initial film thickness and the measured thickness at the given time.
- the coating film was considered to be polished through when a thin, non-polishing leached layer was remaining on the surface, typically 10-20 ⁇ m in thickness, or when the film was totally polished away from the surface. That is denoted as PT in the result tables.
- the polishing index is obtained from the polishing rate between week 52 and week 78 divided by the polishing rate between week 26 and week 52.
- a coating film having a polishing index value below 2.0 is considered to exhibit controlled polishing.
- Table 3 Paint formulation compositions (amounts given in parts by weight).
- Table 5 Test results for paint examples with different binder compositions and comparative paint examples.
- the comparative examples CPA-l to CPA-4 in Table 5 show that the polishing of the antifouling coating film is not controlled over a long period of time without the presence of component (iii) in the antifouling coating composition. The same applies when the amount of component (iii) is low, as shown in comparative example CPA-5.
- the comparative examples CPA-6 to CPA-8 in Table 5 show that the antifouling coating films are soft and prone to mechanical damages when using high amount of component (iii) in the antifouling coating composition.
- the polishing of CPA-6 to CPA-7 is not controlled, as indicated by the high polishing index.
- the coating of CPA-8 has also poor cracking resistance.
- the comparative examples CPA-9 in Table 5 shows that the use of a triisopropylsilyl acrylate copolymer gives an uncontrolled polishing of antifouling coating film.
- Table 6 Paint formulation compositions (amounts given in parts by weight).
- Table 7 Comparative paint formulation compositions (amounts given in parts by weight).
- Table 8 Test results for paint examples with different silyl copolymers and comparative paint examples.
- the comparative examples CPB-l to CPB-5 in Table 8 show that the polishing of the antifouling coating film is not controlled over a long period of time without the presence of component (iii) in the antifouling coating composition.
- the comparative examples CPB-6 to CPB-7 in Table 8 show that the use of component (i) without hydrophilic monomer give too slow polishing to obtain sufficient release of antifouling agents over time.
- the comparative examples CPB-8 to CPB-9 in Table 8 show that the use of a triisopropylsilyl acrylate copolymer gives an uncontrolled polishing of antifouling coating film.
- Table 9 Paint formulation compositions (amounts given in parts by weight).
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB1718899.6A GB201718899D0 (en) | 2017-11-15 | 2017-11-15 | Antifouling coating composition |
GBGB1807388.2A GB201807388D0 (en) | 2017-11-15 | 2018-05-04 | Antifouling composition |
PCT/EP2018/081419 WO2019096926A1 (en) | 2017-11-15 | 2018-11-15 | Antifouling composition |
Publications (1)
Publication Number | Publication Date |
---|---|
EP3710538A1 true EP3710538A1 (en) | 2020-09-23 |
Family
ID=60788465
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP18804577.7A Pending EP3710538A1 (en) | 2017-11-15 | 2018-11-15 | Antifouling composition |
Country Status (8)
Country | Link |
---|---|
EP (1) | EP3710538A1 (zh) |
JP (2) | JP7349241B2 (zh) |
KR (2) | KR20190055759A (zh) |
CN (2) | CN109777298B (zh) |
DE (1) | DE102018128725A1 (zh) |
GB (2) | GB201718899D0 (zh) |
SG (1) | SG11202004483WA (zh) |
WO (1) | WO2019096926A1 (zh) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB201718898D0 (en) * | 2017-11-15 | 2017-12-27 | Jotun As | Antifouling composition |
WO2020138615A1 (ko) | 2018-12-26 | 2020-07-02 | 주식회사 임솔 | 치아 임플란트 식립 가이드의 제조 방법, 그 제조를 위한 예비가이드 및 가이드 트레이 |
GB2592921B (en) | 2020-03-09 | 2024-04-17 | Jotun As | Hull cleaning robot |
KR20220156612A (ko) | 2020-03-27 | 2022-11-25 | 요툰 에이/에스 | 방오성 코팅 조성물 |
JP7295172B2 (ja) * | 2020-08-03 | 2023-06-20 | 関西ペイントマリン株式会社 | 防汚塗料組成物 |
CN114479582B (zh) * | 2020-10-27 | 2023-08-11 | 中石化石油工程技术服务有限公司 | 一种临海油气管道静态环境下用无铜防污涂料及制备方法 |
CN112574631B (zh) * | 2020-12-08 | 2022-02-18 | 浙江大学 | 基于纳米微胶囊控释技术的新型海洋防污涂料组合物 |
BR112023018007A2 (pt) | 2021-03-23 | 2023-10-03 | Jotun As | Monitoração da limpeza de uma superfície subaquática de um objeto estacionário |
GB202107159D0 (en) | 2021-03-23 | 2021-06-30 | Jotun As | Monitoring a vessel |
CN117480220A (zh) * | 2021-05-19 | 2024-01-30 | 日本油漆船舶涂料公司 | 防污涂料组合物以及涂膜 |
CN116396684B (zh) * | 2023-03-29 | 2024-03-01 | 上海佳船工程监理发展有限公司 | 一种船舶用防污涂料及其制备方法 |
Family Cites Families (31)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2204046B (en) | 1987-04-28 | 1991-02-06 | Labofina Sa | Self-polishing antifouling paints |
JP2784725B2 (ja) * | 1994-08-23 | 1998-08-06 | 大日本塗料株式会社 | 防汚塗料組成物 |
CN1198887C (zh) | 1996-05-22 | 2005-04-27 | 亨普尔股份公司 | 防污涂料 |
JP4094170B2 (ja) | 1999-05-07 | 2008-06-04 | 大日本塗料株式会社 | 防汚塗料組成物 |
WO2000077102A1 (en) | 1999-06-11 | 2000-12-21 | J.C. Hempel's Skibsfarve-Fabrik A/S | Self-polishing marine antifouling paint composition comprising silicon-containing co-polymers and fibres |
EP1127902A1 (en) | 2000-02-25 | 2001-08-29 | Sigma Coatings B.V. | Metal-free binders for self-polishing anti-fouling paints |
JP4812947B2 (ja) | 2001-02-21 | 2011-11-09 | 日本ペイント株式会社 | ハイソリッド型防汚塗料 |
EE05295B1 (et) * | 2000-07-06 | 2010-04-15 | International Coatings Limited | Saastumisvastane vrv |
JP2002080778A (ja) * | 2000-09-07 | 2002-03-19 | Chugoku Marine Paints Ltd | 防汚塗料組成物、その塗膜、その塗膜で被覆された漁具・漁網および漁具・漁網の防汚方法 |
EP1288234A1 (en) | 2001-08-27 | 2003-03-05 | Sigma Coatings B.V. | Binders with low content in hydrolysable monomer suitable for selfpolishing antifouling paints |
EP1458821B1 (en) | 2001-12-20 | 2006-05-17 | Hempel A/S | Non-aqueous dispersion based antifouling paint composition |
JP3811749B2 (ja) | 2001-12-20 | 2006-08-23 | 大日本塗料株式会社 | 非水分散型防汚塗料組成物 |
NO20020846L (no) | 2002-02-21 | 2003-08-22 | Jotun As | Selvpolerende begroingshindrende maling |
ATE345361T1 (de) | 2003-07-07 | 2006-12-15 | Akzo Nobel Coatings Int Bv | Silylestercopolymerzusammensetzungen |
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 |
EP2161316B1 (en) | 2007-06-22 | 2017-08-30 | Nitto Kasei Co., Ltd. | Antifouling coating composition, process for producing the composition, antifouling coating film formed from the composition, coated object having the coating film on surface, and method of antifouling treatment by formation of the coating film |
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 |
ATE543844T1 (de) * | 2008-06-11 | 2012-02-15 | Jotun As | Bindemittel für antifouling-lack und antifouling- lack mit bindemittel |
EP2352876B1 (en) | 2008-11-04 | 2012-12-12 | Basf Se | Treated textile material for use in aquatic environments |
EP2386608A1 (en) | 2010-04-20 | 2011-11-16 | PPG Coatings Europe B.V. | A coating composition |
EP2725073B1 (en) * | 2012-10-23 | 2016-08-03 | Jotun A/S | Antifouling coating composition |
SG11201507231SA (en) | 2013-04-24 | 2015-10-29 | Nitto Kasei Co Ltd | Antifouling coating composition, method for producing copolymer for antifouling coating composition, and coated object having, on surface therof, antifouling coating film formed using the composition |
CN105001358A (zh) | 2014-04-24 | 2015-10-28 | 浙江省海洋开发研究院 | 一种丙烯酸铜/锌防污树脂的合成方法 |
CN105295630B (zh) | 2014-06-12 | 2018-04-17 | 浙江省海洋开发研究院 | 一种无锡无铜高活性防污漆及其制备方法 |
JP2016089167A (ja) | 2014-10-31 | 2016-05-23 | 中国塗料株式会社 | 防汚塗料組成物、防汚塗膜および防汚基材、ならびに防汚基材の製造方法 |
KR101999036B1 (ko) | 2014-11-18 | 2019-07-10 | 주고꾸 도료 가부시키가이샤 | 2액형 방오도료 조성물, 방오도막, 방오기재 및 방오기재의 제조방법 |
KR101769415B1 (ko) | 2014-12-31 | 2017-08-18 | 벽산페인트 주식회사 | 방오도료용 아크릴 공중합체 조성물 및 이를 포함하는 방오도료 조성물 |
KR102626623B1 (ko) * | 2015-04-09 | 2024-01-17 | 요툰 에이/에스 | 방오성 조성물 |
JP2016216651A (ja) * | 2015-05-22 | 2016-12-22 | 中国塗料株式会社 | 防汚塗料組成物、防汚塗膜、防汚基材、および防汚基材の製造方法 |
JP6663928B2 (ja) | 2015-11-30 | 2020-03-13 | 中国塗料株式会社 | 防汚性複合塗膜、防汚基材、および該防汚基材の製造方法 |
EP3693426B1 (en) | 2017-10-04 | 2021-12-29 | Nitto Kasei Co., Ltd. | Antifouling paint composition and coated article having antifouling coating formed using said composition on surface |
-
2017
- 2017-11-15 GB GBGB1718899.6A patent/GB201718899D0/en not_active Ceased
-
2018
- 2018-05-04 GB GBGB1807388.2A patent/GB201807388D0/en not_active Ceased
- 2018-11-14 JP JP2018213627A patent/JP7349241B2/ja active Active
- 2018-11-14 KR KR1020180139920A patent/KR20190055759A/ko not_active Application Discontinuation
- 2018-11-15 JP JP2020526563A patent/JP7332593B2/ja active Active
- 2018-11-15 DE DE102018128725.9A patent/DE102018128725A1/de active Pending
- 2018-11-15 EP EP18804577.7A patent/EP3710538A1/en active Pending
- 2018-11-15 CN CN201811362407.3A patent/CN109777298B/zh active Active
- 2018-11-15 SG SG11202004483WA patent/SG11202004483WA/en unknown
- 2018-11-15 KR KR1020207017207A patent/KR20200087820A/ko not_active Application Discontinuation
- 2018-11-15 CN CN201880086456.0A patent/CN111601856B/zh active Active
- 2018-11-15 WO PCT/EP2018/081419 patent/WO2019096926A1/en unknown
Also Published As
Publication number | Publication date |
---|---|
DE102018128725A1 (de) | 2019-05-16 |
KR20200087820A (ko) | 2020-07-21 |
CN111601856A (zh) | 2020-08-28 |
JP2021503027A (ja) | 2021-02-04 |
KR20190055759A (ko) | 2019-05-23 |
CN111601856B (zh) | 2023-05-23 |
CN109777298B (zh) | 2022-07-12 |
JP7332593B2 (ja) | 2023-08-23 |
SG11202004483WA (en) | 2020-06-29 |
CN109777298A (zh) | 2019-05-21 |
GB201807388D0 (en) | 2018-06-20 |
JP2019090019A (ja) | 2019-06-13 |
GB201718899D0 (en) | 2017-12-27 |
WO2019096926A1 (en) | 2019-05-23 |
JP7349241B2 (ja) | 2023-09-22 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP3710538A1 (en) | Antifouling composition | |
KR102634288B1 (ko) | 방오성 조성물 | |
JP7427391B2 (ja) | 防汚組成物 | |
KR102547145B1 (ko) | 방오성 조성물 | |
CN109777178B (zh) | 防污组合物 | |
EP3710539A1 (en) | Antifouling composition | |
EP2348077A1 (en) | Antifouling composition | |
JP7372933B2 (ja) | 組成物 | |
JP2020511586A (ja) | 組成物 | |
EP3538614A1 (en) | Antifouling composition | |
WO2018158437A1 (en) | Composition | |
WO2021191388A1 (en) | Antifouling coating composition |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: UNKNOWN |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE INTERNATIONAL PUBLICATION HAS BEEN MADE |
|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE |
|
17P | Request for examination filed |
Effective date: 20200611 |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR |
|
AX | Request for extension of the european patent |
Extension state: BA ME |
|
DAV | Request for validation of the european patent (deleted) | ||
DAX | Request for extension of the european patent (deleted) | ||
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: EXAMINATION IS IN PROGRESS |
|
17Q | First examination report despatched |
Effective date: 20231013 |