CN114026181A - 用于防污保护的组合物 - Google Patents
用于防污保护的组合物 Download PDFInfo
- Publication number
- CN114026181A CN114026181A CN202080044338.0A CN202080044338A CN114026181A CN 114026181 A CN114026181 A CN 114026181A CN 202080044338 A CN202080044338 A CN 202080044338A CN 114026181 A CN114026181 A CN 114026181A
- Authority
- CN
- China
- Prior art keywords
- antifouling
- radical
- formula
- compound
- alkyl radical
- 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.)
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- 230000003373 anti-fouling effect Effects 0.000 title claims abstract description 97
- 239000000203 mixture Substances 0.000 title claims abstract description 42
- 238000000576 coating method Methods 0.000 claims abstract description 68
- 150000001875 compounds Chemical class 0.000 claims abstract description 64
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 6
- 239000010949 copper Substances 0.000 claims description 49
- -1 C2-20Alkenyl radical Chemical class 0.000 claims description 46
- 239000003139 biocide Substances 0.000 claims description 35
- 239000011248 coating agent Substances 0.000 claims description 34
- 229920001577 copolymer Polymers 0.000 claims description 31
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 claims description 29
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 claims description 29
- 239000011701 zinc Substances 0.000 claims description 23
- 229920000642 polymer Polymers 0.000 claims description 18
- 229910052802 copper Inorganic materials 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 229910052725 zinc Inorganic materials 0.000 claims description 13
- 229940112669 cuprous oxide Drugs 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 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 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 238000013270 controlled release Methods 0.000 claims description 9
- PDZKZMQQDCHTNF-UHFFFAOYSA-M copper(1+);thiocyanate Chemical compound [Cu+].[S-]C#N PDZKZMQQDCHTNF-UHFFFAOYSA-M 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- XLOMVQKBTHCTTD-UHFFFAOYSA-N zinc oxide Inorganic materials [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 9
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 claims description 8
- 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 8
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 claims description 8
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- CUHVIMMYOGQXCV-UHFFFAOYSA-N medetomidine Chemical compound C=1C=CC(C)=C(C)C=1C(C)C1=CNC=N1 CUHVIMMYOGQXCV-UHFFFAOYSA-N 0.000 claims description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 claims description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- 239000005870 Ziram Substances 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 229910052749 magnesium Inorganic materials 0.000 claims description 5
- 239000011787 zinc oxide Substances 0.000 claims description 5
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 claims description 5
- 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
- 101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 claims description 4
- 239000005747 Chlorothalonil Substances 0.000 claims description 4
- 239000005510 Diuron Substances 0.000 claims description 4
- 239000011717 all-trans-retinol Substances 0.000 claims description 4
- 235000019169 all-trans-retinol Nutrition 0.000 claims description 4
- 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 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 239000011777 magnesium Substances 0.000 claims description 4
- 229910052748 manganese Inorganic materials 0.000 claims description 4
- 229960002140 medetomidine Drugs 0.000 claims description 4
- 229910052711 selenium Inorganic materials 0.000 claims description 4
- 229940043810 zinc pyrithione Drugs 0.000 claims description 4
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 claims description 4
- 239000005751 Copper oxide Substances 0.000 claims description 3
- 229910052791 calcium Inorganic materials 0.000 claims description 3
- 239000011575 calcium Substances 0.000 claims description 3
- 229910000431 copper oxide Inorganic materials 0.000 claims description 3
- 239000011572 manganese Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- BCQZXOMGPXTTIC-UHFFFAOYSA-N halothane Chemical compound FC(F)(F)C(Cl)Br BCQZXOMGPXTTIC-UHFFFAOYSA-N 0.000 claims description 2
- 229960003132 halothane Drugs 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 1
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims 1
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 58
- 239000003973 paint Substances 0.000 description 25
- 150000003254 radicals Chemical class 0.000 description 22
- 229920000058 polyacrylate Polymers 0.000 description 19
- 230000003115 biocidal effect Effects 0.000 description 14
- 239000011230 binding agent Substances 0.000 description 13
- 239000000178 monomer Substances 0.000 description 13
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 11
- 238000005498 polishing Methods 0.000 description 10
- 239000013535 sea water Substances 0.000 description 9
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 8
- 239000013642 negative control Substances 0.000 description 7
- QPLDLSVMHZLSFG-UHFFFAOYSA-N CuO Inorganic materials [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 6
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 6
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 5
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 5
- 239000000853 adhesive Substances 0.000 description 5
- 230000001070 adhesive effect Effects 0.000 description 5
- OCJKUQIPRNZDTK-UHFFFAOYSA-N ethyl 4,4,4-trifluoro-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)C(F)(F)F OCJKUQIPRNZDTK-UHFFFAOYSA-N 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 5
- HFCUBKYHMMPGBY-UHFFFAOYSA-N 2-methoxyethyl prop-2-enoate Chemical compound COCCOC(=O)C=C HFCUBKYHMMPGBY-UHFFFAOYSA-N 0.000 description 4
- 241000238586 Cirripedia Species 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229960004643 cupric oxide Drugs 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 229940063557 methacrylate Drugs 0.000 description 4
- FFHSWCQVNPBNOY-UHFFFAOYSA-N 4,4,4-trifluoro-N,N-dimethyl-3-oxobutanamide Chemical compound CN(C)C(=O)CC(=O)C(F)(F)F FFHSWCQVNPBNOY-UHFFFAOYSA-N 0.000 description 3
- IWCXWPIIRVBVNN-UHFFFAOYSA-N COC(C=C)=O.[Zn] Chemical group COC(C=C)=O.[Zn] IWCXWPIIRVBVNN-UHFFFAOYSA-N 0.000 description 3
- 229910016551 CuPt Inorganic materials 0.000 description 3
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical group CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 3
- 238000009360 aquaculture Methods 0.000 description 3
- 244000144974 aquaculture Species 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- NXVKRKUGIINGHD-ARJAWSKDSA-N ethyl (z)-3-amino-4,4,4-trifluorobut-2-enoate Chemical compound CCOC(=O)\C=C(/N)C(F)(F)F NXVKRKUGIINGHD-ARJAWSKDSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- XRCSXYDSFRSLEX-UHFFFAOYSA-N methyl 2-(1h-benzimidazol-2-yl)acetate Chemical compound C1=CC=C2NC(CC(=O)OC)=NC2=C1 XRCSXYDSFRSLEX-UHFFFAOYSA-N 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- GRJISGHXMUQUMC-UHFFFAOYSA-N silyl prop-2-enoate Chemical compound [SiH3]OC(=O)C=C GRJISGHXMUQUMC-UHFFFAOYSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 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 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 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
- WYVVKGNFXHOCQV-UHFFFAOYSA-N 3-iodoprop-2-yn-1-yl butylcarbamate Chemical compound CCCCNC(=O)OCC#CI WYVVKGNFXHOCQV-UHFFFAOYSA-N 0.000 description 2
- 241000700670 Bryozoa Species 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 239000005749 Copper compound Substances 0.000 description 2
- 241000195493 Cryptophyta Species 0.000 description 2
- 229910000570 Cupronickel Inorganic materials 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 241000243320 Hydrozoa Species 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000005802 Mancozeb Substances 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- 241000237536 Mytilus edulis Species 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 239000002519 antifouling agent Substances 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 150000001880 copper compounds Chemical class 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000003628 erosive effect Effects 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
- 235000020638 mussel Nutrition 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229930185156 spinosyn Natural products 0.000 description 2
- XKMZOFXGLBYJLS-UHFFFAOYSA-L zinc;prop-2-enoate Chemical compound [Zn+2].[O-]C(=O)C=C.[O-]C(=O)C=C XKMZOFXGLBYJLS-UHFFFAOYSA-L 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
- VHZJMAJCUAWIHV-UHFFFAOYSA-N 1-(2,4,6-trichlorophenyl)pyrrole-2,5-dione Chemical compound ClC1=CC(Cl)=CC(Cl)=C1N1C(=O)C=CC1=O VHZJMAJCUAWIHV-UHFFFAOYSA-N 0.000 description 1
- XOILGBPDXMVFIP-UHFFFAOYSA-N 1-(diiodomethylsulfonyl)-4-methylbenzene Chemical compound CC1=CC=C(S(=O)(=O)C(I)I)C=C1 XOILGBPDXMVFIP-UHFFFAOYSA-N 0.000 description 1
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 1
- QHMVQKOXILNZQR-UHFFFAOYSA-N 1-methoxyprop-1-ene Chemical group COC=CC QHMVQKOXILNZQR-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- NFGXHKASABOEEW-UHFFFAOYSA-N 1-methylethyl 11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate Chemical compound COC(C)(C)CCCC(C)CC=CC(C)=CC(=O)OC(C)C NFGXHKASABOEEW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
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- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- RCEJCSULJQNRQQ-UHFFFAOYSA-N 2-methylbutanenitrile Chemical compound CCC(C)C#N RCEJCSULJQNRQQ-UHFFFAOYSA-N 0.000 description 1
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- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明涉及高效防止船舶和海洋结构表面的海洋生物污损的包含式IA和/或IB化合物的防污组合物、它们用于抑制海洋生物污损的用途，以及包含所述组合物的防污涂料。
Description
技术领域
本发明涉及高效防止船舶和海洋结构表面的海洋生物污损的包含式IA和/或IB化合物的防污组合物、它们用于抑制海洋生物污损的用途，以及包含所述组合物的防污涂料。
背景技术
船舶、水产养殖渔网、水下结构和设备往往受到诸如藤壶、苔藓虫、水螅虫、蚌类、藻类等海洋生物的侵蚀。生物可以生长和繁殖，并最终导致严重的问题。例如，在船舶的船体的情况下，船体上海洋生物的生长会增加船体与水之间的摩擦阻力，从而增加油耗并降低船舶速度。需要保护船舶船体免受海洋生物生长的影响，以便保持它们的清洁和光滑以达到最大燃油效率。还有一个问题是将海洋生物从世界的一个地方运输到另一个地方，外来生物有可能破坏本地生态。因此，水下部件需要防止海洋生物污损的充分保护，这通常是通过防污涂料来实现的。
用于此类防污涂料的粘合剂体系通常由易侵蚀粘合剂组成。涂料膜的侵蚀通过随时间从涂层中释放防污剂(杀生物剂)从而阻止污损生物的附着来帮助防止污损。侵蚀性防污涂层有两种主要类型，业界将其描述为“自抛光”和“烧蚀”。
烧蚀涂层的粘合剂体系主要由松香组成，松香会与海水反应以变成水溶性并被侵蚀掉。可替代地，松香或松香衍生物也与诸如聚酯树脂、丙烯酸树脂、环氧树脂、氯乙烯树脂、氯化橡胶树脂、氯化聚乙烯树脂、氯化聚丙烯树脂、苯乙烯-丁二烯树脂或聚酰胺树脂等非易侵蚀粘合剂混合使用。
在“自抛光防污涂层”中，粘合剂体系基于可水解的丙烯酸酯聚合物。可水解官能团通常通过金属羧酸盐丙烯酸酯单体或丙烯酸甲硅烷基酯单体提供给聚合物。也使用易侵蚀聚酯粘合剂并使防污涂料成本较低。烧蚀涂层和自抛光涂层之间的区别主要在于浸出层的厚度和自抛光涂层随时间的更具线性的侵蚀率。
也存在“混合涂层”，其粘合剂系统由易侵蚀丙烯酸酯(例如在自抛光涂料中)和松香组成。浸出层的厚度比烧蚀涂层中薄，但比真正的自抛光涂层厚。
由于其中用作杀生物剂的氧化亚铜(Cu2O)的浓度高，即通常约40wt％(这是适当的防污保护所需的)，因此大多数市售防污涂料包含高金属含量。氧化亚铜潜在地对许多生物有害。防污涂料中的浸出会导致水、沉积物和周围环境中的铜水平升高。人为的高铜水平可能具有重大的生态影响。虽然Cu2O在防污涂料中被广泛用作防污剂，但防污涂料还可以包含额外的杀生物剂，因为单独的Cu2O仅对诸如藤壶之类的坚硬污损生物有效。
作为另一个缺点，氧化亚铜通常赋予防污涂料膜浓重的红棕色，并且还可能与大气中的二氧化碳和海水中的氯化物反应以在涂层的表面上形成不均匀的条纹。这是一种不吸引人的外观并且可能例如在船舶下海后不久发生。一些游艇所有者和游轮运营商更喜欢包含氧化亚铜的涂料无法获得的明亮色彩和均匀的外观。
在市售防污涂料中取代氧化亚铜的尝试导致开发了氧化亚铜的替代品，如白色的硫氰酸铜，以及对藤壶有效的农用杀虫剂曲洛比利(tralopyril)。但是这些替代品的成本更高，而且它们不如基于氧化亚铜的防污涂料有效。
因此，需要在生态和经济上改进的海洋防污涂料，其具有降低的铜含量，或者甚至完全替代常规使用的防污涂料中的氧化亚铜。
包含式IA和/或IB化合物的本发明的防污组合物满足了这种需要。发明人惊奇地发现，式IA和IB化合物都是增强所有类型防污涂料(例如烧蚀涂料或自抛光涂料)的防污性能并且还可以以简单的接触浸出涂层使用的高效且通用的试剂。
因此，现在可以部分或完全替代防污涂料中的Cu2O，因而大幅降低其中的金属含量，同时保持适当的防污性能。此外，包含式IA和/或IB化合物的本发明的防污组合物基本上是无色的，因而不会干扰船舶船体通常需要的明亮色彩。
附图说明
图1描绘了涂有实施例2表1的防污涂料的面板，并显示了在海水(姬路，深度：1.5m)中6个月后的面板外观。黑色方块表示阴性对照(即没有任何防污成分的涂层)的区域。
图2描绘了涂有实施例2表2的防污涂料的面板，并显示了在海水(姬路、长崎和女川)中4个月后的面板外观。“长崎”试验和姬路试验的面板6分别显示了在海水中1个月后的面板。“女川”试验的面板6显示了在海水中4个月后的面板。
图3描绘了涂有实施例2表3的防污涂料的面板，并显示了在海水(长崎；深度：1.5m)中1个月后的面板外观。黑色方块表示阴性对照(即没有任何防污成分的涂层)的区域。
具体实施方式
除非另有定义，本文使用的所有技术和科学术语与本发明相关领域的普通技术人员通常理解的含义相同。此处使用了以下缩写词和术语：
AIBN：偶氮双(异丁腈)
AMBN：偶氮双-(2-甲基丁腈)
A630-20X：脂肪酸酰胺
BA：丙烯酸丁酯
百菌清：2,4,5,6-四氯苯-1,3-二甲腈
铜巯氧吡啶
CuPT、吡啶硫酮铜：2-吡啶硫醇-1-氧化铜
Cu2O：氧化亚铜
CuSCN：硫氰酸铜(I)
DCOIT：4,5-二氯-2-正辛基-4-异噻唑啉-3-酮
敌草隆：3-(3,4-二氯苯基)-1,1-二甲基脲
帝司巴隆(Disparlon)A650-20x：合成聚酰胺蜡分散体。作为重颜料和金属漆的优良抗沉降剂。具有高度剪切稀化，使得施加性能卓越。
ETFAA：乙基4,4,4-三氟乙酰乙酸酯
2MEA：2-甲氧基丙烯酸乙酯单体
美托咪啶：4-[1-(2,3-二甲基苯基)乙基]-1H-咪唑
MMA：甲基丙烯酸甲酯单体
MIBK：甲基异丁基酮
MPM：甲氧基丙烯单体
PGM：丙二醇单甲醚
TIPX：丙烯酸三异丙基甲硅烷酯单体
曲洛比利:4-溴-2-(4-氯苯基)-5-(三氟甲基)-1H-吡咯-3-腈
VAGH：氯乙烯/醋酸乙烯/乙烯醇共聚物(商品)
代森锌(Zineb)：乙烷-1,2-二基双(二硫代氨基甲酸酯)锌
福美锌(Ziram)：N,N-二甲基氨基二硫代酯锌
Zn(ETFAA)2：二(乙基4,4,4-三氟乙酰乙酸酯)锌，本文也称为ZnETFAA
ZnO：氧化锌
ZnPT:吡啶硫酮锌：2-吡啶硫醇-1-氧化锌
术语“(甲基)丙烯酸酯”是指示丙烯酸酯和甲基丙烯酸酯单体的统称。术语“甲基丙烯酸酯”或“甲基-丙烯酸酯”仅表示甲基丙烯酸酯单体。
膨润土(Bentone)SD2是一种为了抗沉降性能而添加的有机粘土；膨润土#38是季铵盐18-锂蒙脱石粘土；Minex 4是霞石正长岩粘土。帝司巴隆6900-20x(A630-20X聚酰胺蜡)是聚酰胺蜡在二甲苯中的20％分散体，用作流变改性剂；Disperbyk 161是一种分散添加剂。树脂是指可用作本发明防污涂料中使用的粘合剂的原材料的所有预聚物或聚合物。松香或脂松香是指松脂香(CAS:8050-09-7,另见https://www.megaglori.com/what-is-gum-rosin/)。
“杀生物剂”是指防止海洋生物在表面上沉降和/或防止海洋生物在表面上生长和/或促使海洋生物从表面移出的任何化合物。
术语“防污涂料”、“防污涂层”和“防污制剂”在本文中可互换使用。
本发明提供了一种新的方法来抑制诸如船舶船体或任何其他海洋结构的水下物体表面的污损。具体地，本发明提供一种包含式IA和/或IB化合物的防污组合物：
其中
Me代表金属，优选Cu、Zn、Co、Ni、Ca、Mg或Mn；
R1可以是任何带来高疏水性的官能团，例如，
R1各自独立地选自氢、卤素、直链或支链的C1-20烷基、C2-20烯基、C2-20炔基、C3-12环烷基、C6-20芳基和C7-20芳烷基；
R2各自独立地选自NH、O、S和Se；
R3是NH、N(R4)、O、S和Se；
R4是氢、直链或支链的C1-20烷基、C2-20烯基、C2-20炔基、C3-12环烷基、C6-20芳基、C7-20芳烷基；
R5和R6各自独立地选自H、直链或支链的C1-20烷基、C2-20烯基、C2-20炔基、C3-12环烷基、C6-20芳基和C7-20芳烷基；或者
R5和R6一起形成基团＝O、＝S、＝Se、＝NR4、＝C(R4)2、＝C(R4)(OR4)、＝C(R4)(NHR4)。
在一个实施方案中，本发明提供一种防污组合物，其包含如上所示的式IA和/或IB化合物，其中
Me代表Cu、Zn、Ca、Mg或Mn；
R1各自独立地选自H、F、Cl、Br、I、直链或支链的C1-12烷基、C2-12烯基、C2-12炔基、C6-12芳基和C7-12芳烷基；
R2各自独立地选自NH、O和S；
R3是NH、N(R4)、O和S；
R4是H,直链或支链的C1-12烷基、C2-12烯基、C2-12炔基、C3-8环烷基、C6-12芳基、C7-12芳烷基；
R5和R6各自独立地选自H、直链或支链的C1-4烷基、C2-4烯基、C2-4炔基、C3-6环烷基、C6-12芳基和C7-12芳烷基；或者
R5和R6一起形成基团＝O、＝S、＝NR4、＝C(R4)2、＝C(R4)(OR4)、＝C(R4)(NHR4)。
在一个实施方案中，本发明提供一种防污组合物，其包含如上所示的式IA和/或IB化合物，其中
Me代表Cu或Zn；
R1各自独立地选自H、F、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、环丁基、环戊基、环己基、C8烷基、C9烷基、C10烷基、C11烷基、C12烷基和苄基；
R2各自独立地选自NH和O；
R3是N(R4)和O；
R4是H、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、环丁基、环戊基、环己基、C8烷基、C9烷基、C10烷基、C11烷基、C12烷基和苄基；
R5和R6各自独立地选自H、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基和苄基；或者
R5和R6一起形成基团＝CH(OCH3)；＝CH(OC2H5)；＝CH(OnC3H7)；
＝CH(OiC3H7)；＝CH(OnC4H9)；＝CH(OiC4H9)；＝CH(O叔.C4H9),
＝CH(NHCH3)；＝CH(NHC2H5)；＝CH(NHnC3H7)；＝CH(NHiC3H7)；
＝CH(NHnC4H9)；＝CH(NHiC4H9)；＝CH(NH叔.C4H9)。
在一个实施方案中，本发明提供一种防污组合物，其包含如上所示的式IA和/或IB化合物，其中
Me代表Cu或Zn；
R1各自独立地选自H和F；
R2各自独立地选自NH和O；
R3是N(CH3)、N(C2H5)和O；
R4是H、甲基、乙基、正丙基,异丙基、正丁基、异丁基、叔丁基、C8烷基、C9烷基、C10烷基、C11烷基、C12烷基和苄基；
R5和R6各自为H；或者
R5和R6一起形成基团＝CH(OCH3)；＝CH(OC2H5)、＝CH(NHCH3)；
＝CH(NHC2H5)；
在一个实施方案中，式IB化合物如上所定义，条件是如果Me是Cu，则每个R1是F，每个R2是O，R3是O，并且R5和R6各自是H，则R4不是乙基。
合适的式IA和IB化合物分别是，例如
乙基3-氨基-4,4,4-三氟巴豆酸酯；
[乙基3-氨基-4,4,4-三氟巴豆酸酯]2Zn,
[乙基3-氨基-4,4,4-三氟巴豆酸酯]2Cu,
乙基3-氨基-2-亚甲基-(甲氨基)-4,4-二氟巴豆酸酯,
[乙基3-氨基-2-亚甲基-(甲氨基)-4,4-二氟巴豆酸酯]2Zn,
[乙基3-氨基-2-亚甲基-(甲氨基)-4,4-二氟巴豆酸酯]2Cu
4,4,4-三氟-N,N-二甲基-3-氧代丁酰胺；
[4,4,4-三氟-N,N-二甲基-3-氧代丁酰胺]2Cu,
[4,4,4-三氟-N,N-二甲基-3-氧代丁酰胺]2Zn,
十二烷基4,4,4-三氟-3-氧代丁酸酯,
[十二烷基4,4,4-三氟-3-氧代丁酸酯]2Zn,
十二烷基4,4,4-三氟-3-氧代丁酸酯]2Cu,
苄基4,4,4-三氟乙酰乙酸酯,
[苄基4,4,4-三氟乙酰乙酸酯]2Zn,
[苄基4,4,4-三氟乙酰乙酸酯]2Cu,
辛基4,4,4-三氟乙酰乙酸酯,
[辛基4,4,4-三氟乙酰乙酸酯]2Zn,
[辛基4,4,4-三氟乙酰乙酸酯]2Cu,
异丙基4,4,4-三氟乙酰乙酸酯,
[异丙基4,4,4-三氟乙酰乙酸酯]2Zn,
[异丙基4,4,4-三氟乙酰乙酸酯]2Cu,
乙基4,4,4-三氟乙酰乙酸酯,
[乙基4,4,4-三氟乙酰乙酸酯]2Zn
叔丁基4,4,4-三氟-3-氧代丁酸酯,
[叔丁基4,4,4-三氟-3-氧代丁酸酯]2Zn,
[叔丁基4,4,4-三氟-3-氧代丁酸酯]2Cu
在一些实施方案中，防污组合物包含如上定义的式IA或IB化合物。在一些实施方案中，防污组合物包含如上定义的式IA和IB化合物。
令人惊奇地发现，式IA和IB化合物显著增强了防污组合物对海洋生物(如藤壶、苔藓虫、水螅虫、蚌类、藻类等)的沉降的防污功效。
本发明的防污组合物可以进一步包含能够防止物体表面污损的一种或多种杀生物剂。
这种杀生物剂可以是无机杀生物剂、有机金属杀生物剂或有机杀生物剂。
无机杀生物剂的例子是铜和铜化合物，例如氧化铜，例如氧化亚铜和氧化正铜；铜合金，例如铜镍合金；铜盐，例如硫氰酸铜(CuSCN)、硫化铜；或偏硼酸钡。
有机金属杀生物剂的例子是锌2-吡啶硫醇-1-氧化物[ZnPT，吡啶硫酮锌]；有机铜化合物，例如2-吡啶硫醇-1-氧化铜[CuPT，吡啶硫酮铜]、醋酸铜、环烷酸铜、8-氨基脲酸铜[喔星-铜]、壬基酚磺酸铜、双(乙二胺)双(十二烷基苯磺酸)铜和双(五氯苯酚)铜；二硫代氨基甲酸酯化合物，例如N,N-二甲基氨基二硫代酯锌[福美锌]、乙烷-1,2-二基双(二硫代氨基甲酸酯)锌[代森锌]、亚乙基双(二硫代氨基甲酸)锰[代森锰]或与锌盐复合的亚乙基双(二硫代氨基甲酸)锰[代森锰锌]。
有机杀生物剂的例子是杂环化合物，例如2-(叔丁基氨基)-4-(环丙胺)-6-(甲硫基)-1,3,5-三嗪[环丁腈],4,5-二氯-2-正辛基-4-异噻唑啉-3-酮[DCOIT],1,2-苯并异噻唑啉-3-酮[BIT],2-(硫氰酸根合甲硫基)-1,3-苯并噻唑[苯噻唑],3-苯并[b]噻吩-2-基-5,6-二氢-1,4,2-噻嗪-4-氧化物[苯噻唑嗪]和2,3,5,6-四氯-4-(甲基磺酰基)吡啶；脲衍生物，例如3-(3,4-二氯苯基)-1,1-二甲基脲[敌草隆]；羧酸、磺酸和次磺酸的酰胺和酰亚胺，例如N-(二氯氟甲硫基)邻苯二甲酰亚胺,N-二氯氟甲硫基-N',N'-二甲基-N-苯基磺酰胺[抑菌灵],N-二氯氟甲硫基-N',N'-二甲基-N-p-甲苯磺酰胺[对甲抑菌灵]和N-(2,4,6-三氯苯基)马来酰亚胺；其他有机化合物，例如吡啶三苯基硼烷,胺三苯基硼烷,3-碘-2-丙炔基-正丁基氨基甲酸酯[iodocarb],2,4,5,6-四氯间苯二腈[百菌清],对-((二碘甲基)磺酰基)甲苯或4-溴-2-(4-氯苯基)-5-(三氟甲基)-1H-吡咯-3-腈[曲洛比利]。
杀生物剂的其他例子是四烷基鏻卤化物(tetra-alkylphosphoniumhalogenide)；胍衍生物；含咪唑的化合物，例如4-[1-(2,3-二甲基苯基)乙基]-1H-咪唑[美托咪定]以及衍生物；大环内酯，包括阿维菌素及其衍生物，例如伊维菌素，或多杀菌素及其衍生物，例如多杀霉素，或酶，例如氧化酶，或具有蛋白水解、半纤维素分解、纤维素分解、脂肪分解或淀粉分解活性的酶。
在一个实施方案中，本发明的防污组合物包含如上所定义的式IA和/或IB化合物和选自由以下项组成的组的另外一种或多种杀生物剂：2-吡啶硫醇-1-氧化铜(CuPT，吡啶硫酮铜),2-吡啶硫醇-1-氧化锌(ZnPT，吡啶硫酮锌),4,5-二氯-2-正辛基-4-异噻唑啉-3-酮(DCOIT),氧化亚铜(Cu2O),氧化锌(ZnO),4-溴-2-(4-氯苯基)-5-(三氟甲基)-1H-吡咯-3-腈(曲洛比利),乙烷-1,2-二基双(二硫代氨基甲酸酯)锌(代森锌),N,N-二甲基甲基氨基二硫代酯锌(福美锌),3-(3,4-二氯苯基)-1,1-二甲基脲(敌草隆),硫氰酸铜(I)(CuSCN),4-[1-(2,3-二甲基苯基)乙基]-1H-咪唑(美托咪定),三嗪,氟烷和2,4,5,6-四氯间苯二腈(百菌清)。
在优选的实施方案中，本发明的防污组合物包含如上定义的式IA和/或IB化合物和选自CuPT、ZnPT、DCOIT、Cu2O和曲洛比利的一种或多种杀生物剂。
在更优选的实施方案中，本发明的防污组合物包含如上定义的式IA和/或IB化合物和选自CuPT和Cu2O的一种或多种杀生物剂。所述式IA和/或IB化合物(wt％)与CuPT(wt％)的比率和/或所述式IA和/或IB化合物(wt％)与Cu2O(wt％)的比率有利地为100:1至1:100，优选15:1至1:15，最优选5:1至1:5。
在具体的实施方案中，本发明的防污组合物包含所述式IA和/或IB化合物和CuPT。所述式IA和/或IB化合物(wt％)与CuPT(wt％)的比率有利地为100:1至1:100，优选10:1至1:10，最优选5:1到1:5。
在另一个具体的实施方案中，本发明的防污组合物包含所述式IA和/或IB化合物和Cu2O。所述式IA和/或IB化合物(wt％)与Cu2O(wt％)的比率有利地为100:1至1:100，优选10:1至1:10，最优选5:1到1:5。
在更具体的实施方案中，本发明的防污组合物包含所述式IA和/或IB化合物、CuPT和Cu2O，其中所述式IA和/或IB化合物(wt％)与CuPT(wt％)的比率为5:1至5:1，并且其中所述式IA和/或IB化合物(wt％)与Cu2O(wt％)的比率为5:1至1:5。
在另一个具体的实施方案中，本发明的防污组合物包含所述式IA和/或IB化合物和CuPT并且不含Cu2O，其中所述式IA和/或IB化合物(wt％)与CuPT(wt％)的比率是5:1至5:1。
包含如上定义的式IA和/或IB化合物的本发明的防污组合物不仅提供优异的防污性能，而且基本上是无色的，因此不干扰船舶船体通常需要的明亮色彩。
本发明进一步提供了本发明的防污组合物用于抑制固体表面上的海洋生物污损的用途。固体表面可以是水下物体(例如船舶、水产养殖渔网、水下结构和设备、罐、海上建筑、管道、网、码头、桩或柱等)的任何固体表面。
本发明的防污组合物可以进一步与聚合物和/或共聚物组合使用，从而允许控制释放所述式IA和/或IB化合物，并且如果存在，还允许控制释放包含在其中的所述一种或多种杀生物剂，例如通过随着时间的推移从防污涂层中释放这些试剂(如自抛光或烧蚀涂层的情况一样)。
本发明人惊奇地发现，式IA和/或IB化合物是可在所有类型的防污涂层(即基于通常用作防污涂层组合物的粘合剂的各种不同聚合物和/或共聚物的防污涂层)中使用的通用试剂。因此，允许控制释放所述式IA和/或IB化合物并且如果存在也允许控制释放其中包含的所述一种或多种杀生物剂的聚合物和/或共聚物可以是通常用作防污涂层中的粘合剂的任何聚合物和/或共聚物。用于该目的的合适的聚合物和/或共聚物是本领域技术人员已知的。取决于所使用的粘合剂的量和种类，所述式IA和/或IB化合物和一种或多种杀生物剂将以例如适合于船舶航行模式的预定期望速率以受控方式释放。
例如，在“自抛光防污涂层”中用作粘合剂的允许控制释放所述式IA和/或IB化合物和所述一种或多种杀生物剂的聚合物和/或共聚物可以是可水解的丙烯酸酯聚合物，例如(甲基)丙烯酸酯基聚合物和/或共聚物。(甲基)丙烯酸酯聚合物和/或共聚物中的(甲基)丙烯酸酯单体部分可以是烷基(甲基)丙烯酸酯,例如甲基(甲基)丙烯酸酯,乙基(甲基)丙烯酸酯,丙基(甲基)丙烯酸酯,异丙基(甲基)丙烯酸酯,丁基(甲基)丙烯酸酯,异丁基(甲基)丙烯酸酯,叔丁基(甲基)丙烯酸酯,戊基(甲基)丙烯酸酯,己基(甲基)丙烯酸酯,庚基(甲基)丙烯酸酯,环己基(甲基)丙烯酸酯,辛基(甲基)丙烯酸酯,异辛基(甲基)丙烯酸酯,2-乙基己基(甲基)丙烯酸酯,3,5,5-三甲基己基(甲基)丙烯酸酯,月桂基(甲基)丙烯酸酯,鲸蜡基(甲基)丙烯酸酯和硬脂基(甲基)丙烯酸酯；还有苯基(甲基)丙烯酸酯；苄基(甲基)丙烯酸酯；或者烷氧基烷基(甲基)丙烯酸酯，例如甲氧基甲基(甲基)丙烯酸酯,2-甲氧基乙基(甲基)丙烯酸酯,乙氧基甲基(甲基)丙烯酸酯,2-乙氧基乙基(甲基)丙烯酸酯,4-甲氧基丁基(甲基)丙烯酸酯,甲氧基丙基(甲基)丙烯酸酯,乙氧基丙基(甲基)丙烯酸酯,丙氧基乙基(甲基)丙烯酸酯,2-丁氧基乙基(甲基)丙烯酸酯,异丁氧基丁基二甘醇(甲基)丙烯酸酯；还有苯氧基乙基(甲基)丙烯酸酯；或者羟基烷基(甲基)丙烯酸酯，例如羟基甲基(甲基)丙烯酸酯,2-羟基乙基(甲基)丙烯酸酯,2-羟基丙基(甲基)丙烯酸酯,4-羟基丁基(甲基)丙烯酸酯或2-羟基-3-苯氧基丙基(甲基)丙烯酸酯；
(甲基)丙烯酸酯聚合物和/或共聚物中的(甲基)丙烯酸酯单体部分可以进一步是甲硅烷基(甲基)丙烯酸酯，例如三苄基甲硅烷基(甲基)丙烯酸酯,三甲基甲硅烷基(甲基)丙烯酸酯,三乙基甲硅烷基(甲基)丙烯酸酯,三异丙基甲硅烷基(甲基)丙烯酸酯,三正丁基甲硅烷基(甲基)丙烯酸酯,三异丁基甲硅烷基(甲基)丙烯酸酯,三叔丁基甲硅烷基(甲基)丙烯酸酯,三正戊基甲硅烷基(甲基)丙烯酸酯,三正十二烷基甲硅烷基(甲基)丙烯酸酯,三正己基甲硅烷基(甲基)丙烯酸酯,三正辛基甲硅烷基(甲基)丙烯酸酯,三正丙基甲硅烷基(甲基)丙烯酸酯或三苯基甲硅烷基(甲基)丙烯酸酯；
(甲基)丙烯酸酯聚合物和/或共聚物还可包含丙烯酸或甲基丙烯酸的金属盐部分，本文称为“(甲基)丙烯酸金属盐”。金属可以是技术人员已知的任何合适的金属，例如锌、钙、镁、锂、铁、锆、铝、钴、锆、钡和铋。
允许控制释放所述式IA和/或IB化合物并且如果存在还允许控制释放所述一种或多种杀生物剂的聚合物和/或共聚物也可以是VAGH共聚物。VAGH共聚物可以溶解在2:3二甲苯:MIBK中。
因此，在一个实施方案中，允许所述式IA和/或IB化合物控制释放并且如果存在还允许控制释放所述一种或多种杀生物剂的聚合物和/或共聚物包含(甲基)丙烯酸酯聚合物和/或共聚物，或VAGH共聚物。(甲基)丙烯酸酯聚合物和/或共聚物可以是选自由烷基(甲基)丙烯酸酯,苯基(甲基)丙烯酸酯,苄基(甲基)丙烯酸酯,烷氧基烷基(甲基)丙烯酸酯,羟基烷基(甲基)丙烯酸酯,(甲基)丙烯酸锌和甲硅烷基-(甲基)丙烯酸酯组成的组的单体部分的聚合物或共聚物；或(甲基)丙烯酸酯聚合物和/或共聚物可以是选自由乙基丙烯酸酯,甲基丙烯酸甲酯,丁基丙烯酸酯,2-甲氧基乙基丙烯酸酯,锌丙烯酸甲酯和三异丙基甲硅烷基丙烯酸酯组成的组的单体部分的聚合物或共聚物，优选地，(甲基)丙烯酸酯聚合物和/或共聚物是选自由乙基丙烯酸酯,甲基丙烯酸甲酯和锌丙烯酸甲酯组成的组的单体部分的共聚物，更优选地，(甲基)丙烯酸酯聚合物和/或共聚物是选自由乙基丙烯酸酯,甲基丙烯酸甲酯,2-甲氧基乙基丙烯酸酯和锌丙烯酸甲酯组成的组的单体部分的共聚物，并且最优选地，(甲基)丙烯酸酯聚合物聚合物和/或共聚物是选自由甲基丙烯酸甲酯,丁基丙烯酸酯,2-甲氧基乙基丙烯酸酯和三异丙基甲硅烷基丙烯酸酯组成的组的单体部分的共聚物。
因此，本发明进一步提供了一种防污涂料，其包含本发明的防污组合物和聚合物和/或共聚物，所述聚合物和/或共聚物允许控制释放所述式IA和/或IB化合物并且如果存在还允许控制释放所述一种或多种杀生物剂。
所述式IA和/或IB化合物在本发明的防污涂料中的含量为约1至约25wt％，优选约3至约20wt％，更优选约4至约18wt％，最优选约5至约15wt％。
由于所述式IA和/或IB化合物的优异增强特性，在本发明的防污涂料中仅需要少量的所述一种或多种杀生物剂。本发明的防污涂料中的一种或多种杀生物剂的总含量小于约30wt％，优选小于约25wt％，更优选小于约20wt％，最优选小于约18wt％。
本发明的防污涂料中CuPT的总含量小于约10wt％，更优选小于约8wt％，并且最优选小于约7wt％。
本发明的防污涂料中Cu2O的总含量小于约20wt％，更优选小于约15wt％，最优选小于约12wt％。
因此，有毒的金属化合物(特别是Cu2O)的含量保持在非常低的水平，甚至可以避免。
本发明进一步提供了一种用于抑制固体表面上海洋生物污损的方法，其特征在于将包含本发明的防污组合物的防污涂料施加在所述表面上。固体表面可以是水下物体(例如船舶、水产养殖渔网、水下结构和设备、罐、海上建筑、管道、网、码头、桩或柱等)的任何固体表面。
下面结合实施例对本发明作进一步说明，但应理解为本发明不受这些实施例的任何限制。
实施例
实施例1：用于防污涂料的示例性聚合物基粘合剂的制备
可用于自抛光防污涂料或混合涂层的不同示例性聚合物基粘合剂已按以下概述制备。
实施例1A：合成丙烯酸酯聚合物“酸性丙烯酸酯低酸值”(本文称为“Ac(AV＝100-)”)
实施例1B：合成丙烯酸酯聚合物“酸性丙烯酸酯100酸值”(本文称为“Ac(AV＝100)”)
实施例1C：使用丙烯酸酯聚合物“Ac(AV＝100-)”合成粘合剂组分以得到丙烯酸锌聚合物(本文称为“Zn-Ac(AV＝100-)”)
实施例1D：使用丙烯酸酯聚合物“Ac(AV＝100)”合成粘合剂组分以得到丙烯酸锌聚合物(本文称为“Zn-Ac(AV＝100)”)
实施例1E：合成甲硅烷基丙烯酸酯聚合物标准TIPX粘合剂组分(本文称为“Si-Ac”)
实施例1F：合成甲硅烷基丙烯酸酯聚合物低级TIPX粘合剂组分(本文称为“Si-Ac(TIPX-L)”)
实施例2：Cu2O和本发明化合物在防污涂料中的效力
为了确认如果本发明的式IA或IB化合物存在于防污涂料中可以显著减少Cu2O的量，通过将施加涂料的实验面板浸入试验筏的海水中来评估一组烧蚀防污涂料的功效。
已经为此目的制备了多种烧蚀防污涂料，其a)仅包含本发明的IA或IB化合物(即，没有杀生物剂)，b)包含本发明的IA或IB化合物连同杀生物剂(即Cu2O)，c)仅包含杀生物剂(即，Cu2O，或Cu2O连同CuPT分别作为“阳性对照涂料”)，以及d)不含杀生物剂且不含IA或IB化合物(“阴性对照涂料”)。
本实施例中采用的本发明的化合物描绘于下表1中。涂料的详细配方描绘于下表2至4中。涂料已按如下方式施加于PVC面板。
每个面板被分成三个部分，并用三种不同浓度(即，25％v/v、15％v/v和5％v/v)的相应涂料(即，包含杀生物剂，或本发明的化合物，或杀生物剂连同本发明的化合物)进行涂覆。这些成分的浓度如图1至3所示。
结果：在海水中浸泡预定时间(1、4或6个月，如下所示)后的结果示于图1、图2和图3。
图1：
面板1描绘了涂有如下表2所示的仅含Cu2O的防污涂料配方的面板。这三个部分表示已用包含不同浓度Cu2O的涂料处理过的面板上的3个区域。施加于第1部分的涂料包含15％v/v的Cu2O，施加于面板的第2部分的涂料包含5％v/v的Cu2O。面板1的最后部分(用正方形强调)是施加涂料的面板的阴性对照，其中涂料不包含任何防污作用成分，即既不包含杀生物剂也不包含式IA或IB化合物。图1中的面板6和面板12是未处理的PVC面板的阴性对照。图1的面板2至5和7至10类似于如图1所示的包含不同浓度的式IA或IB化合物的涂料。
图2：
在每个试验(即在长崎、姬路和女川)中，图2中的面板1是涂有如下表3所示的仅含Cu2O的防污涂料配方的面板。施加于面板的三个部分的涂料中所含成分的浓度如图2所示。浓度为25、15、5体积％。图2中每个试验中的面板6是未处理的PVC面板的阴性对照。每个试验中的面板4在第1部分中类似于具有25％v/v CuPt的涂料；在第2部分中类似于具有5％v/v Cu2O和25％CuPt的涂料，并且在第3部分中类似于具有5％v/v Cu2O和15％v/v CuPt的涂料。每个试验中的面板5在第1部分中类似于具有25％v/v ZnETFAA的涂料，在第2部分中类似于具有5％v/v Cu2O和25％ZnETFAA的涂料，并且在第3部分中类似于具有5％v/v Cu2O和15％v/v ZnETFAA的涂料。
图3：
图3中的面板7和10仅涂有如下表3所示的仅含Cu2O和Cu2O/CuPT防污涂料配方。浓度为25、15、5体积％。图3中的面板12是未处理的PVC面板的阴性对照。面板1至6在第1部分中类似于具有25％v/v的本发明化合物的涂料(即面板1:Der-2-Cu；面板2:Der-3-Cu；面板3:Der-4-Cu；面板4:Der-5-Cu；面板5:Der-6-Cu；面板6:Der-7-Cu，如图3和下表1所示)；在第2部分中类似于具有5％v/v Cu2O和25％的本发明化合物的涂料，并且在第3部分中类似于具有5％v/v Cu2O和15％v/v的本发明化合物的涂料。
与未处理的面板对照和素色涂料对照相比，类似于具有不同浓度的本发明化合物的涂料的面板的所有部分都显示出改进的防污性能。
观察到所有评估的衍生物都在提高防污涂料性能的总体趋势。
Claims (14)
1.包含式IA和/或IB化合物的防污组合物
其中
Me代表金属，优选Cu、Zn、Co、Ni、Ca、Mg或Mn；
R1各自独立地选自氢、卤素、直链或支链的C1-20烷基、C2-20烯基、C2-20炔基、C3-12环烷基、C6-20芳基和C7-20芳烷基；
R2各自独立地选自NH、O、S和Se；
R3是NH、N(R4)、O、S和Se；
R4为氢、直链或支链的C1-20烷基、C2-20烯基、C2-20炔基、C3-12环烷基、C6-20芳基、C7-20芳烷基；
R5和R6各自独立地选自H、直链或支链的C1-20烷基、C2-20烯基、C2-20炔基、C3-12环烷基、C6-20芳基和C7-20芳烷基；或者
R5和R6一起形成基团＝O、＝S、＝Se、＝NR4、＝C(R4)2、＝C(R4)(OR4)、＝C(R4)(NHR4)。
2.如权利要求1所述的防污组合物，其中在所述式IA和/或IB化合物中
Me代表Cu、Zn、Ca、Mg或Mn；
R1各自独立地选自H、F、Cl、Br、I、直链或支链的C1-12烷基、C2-12烯基、C2-12炔基、C6-12芳基和C7-12芳烷基；
R2各自独立地选自NH、O和S；
R3是NH、N(R4)、O和S；
R4是H、直链或支链的C1-12烷基、C2-12烯基、C2-12炔基、C3-8环烷基、C6-12芳基、C7-12芳烷基；
R5和R6各自独立地选自H、直链或支链的C1-4烷基、C2-4烯基、C2-4炔基、C3-6环烷基、C6-12芳基和C7-12芳烷基；或者
R5和R6一起形成基团＝O、＝S、＝NR4、＝C(R4)2、＝C(R4)(OR4)、＝C(R4)(NHR4)。
3.如权利要求1或2所述的防污组合物，其中在所述式IA和/或IB化合物中
Me代表Cu或Zn；
R1各自独立地选自H、F、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、环丁基、环戊基、环己基、C8烷基、C9烷基、C10烷基、C11烷基、C12烷基和苄基；
R2各自独立地选自NH和O；
R3是N(R4)和O；
R4是H、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、环丁基、环戊基、环己基、C8烷基、C9烷基、C10烷基、C11烷基、C12烷基和苄基；
R5和R6各自独立地选自H、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基和苄基；或者
R5和R6一起形成基团＝CH(OCH3)；＝CH(OC2H5)；＝CH(OnC3H7)；＝CH(OiC3H7)；＝CH(OnC4H9)；＝CH(OiC4H9)；＝CH(OtertC4H9),＝CH(NHCH3)；＝CH(NHC2H5)；＝CH(NHnC3H7)；＝CH(NHiC3H7)；＝CH(NHnC4H9)；＝CH(NHiC4H9)；＝CH(NHtertC4H9)。
4.如前述权利要求中任一项所述的防污组合物，其中所述一种或多种杀生物剂选自由以下项组成的组：2-吡啶硫醇-1-氧化铜(吡啶硫酮铜，CuPT)、2-吡啶硫醇-1-氧化锌(吡啶硫酮锌，ZnPT)、4,5-二氯-2-正辛基-4-异噻唑啉-3-酮(DCOIT)、氧化亚铜(Cu2O)、氧化锌(ZnO)、4-溴-2-(4-氯苯基)-5-(三氟甲基)-1H-吡咯-3-腈(曲洛比利)、乙烷-1,2-二基双(二硫代氨基甲酸酯)锌(代森锌)、N,N-二甲基氨基二硫代酯锌(福美锌)、3-(3,4-二氯苯基)-1,1-二甲基脲(敌草隆)、硫氰酸铜(I)(CuSCN)、4-[1-(2,3-二甲基苯基)乙基]-1H-咪唑(美托咪定)、三嗪、氟烷和2,4,5,6-四氯间苯二甲腈(百菌清)。
5.根据前述权利要求中任一项所述的防污组合物，其中所述一种或多种杀生物剂选自CuPT、ZnPT、DCOIT、Cu2O和曲洛比利。
6.如前述权利要求中任一项所述的防污组合物，其中所述一种或多种杀生物剂选自CuPT和Cu2O。
7.如权利要求6所述的防污组合物，其中式IA和/或IB化合物(wt％)与CuPT(wt％)的比率，和/或式IA和/或IB化合物(wt％)与Cu2O(wt％)的比率为100:1至1:100。
8.如前述权利要求中任一项所述的防污组合物用于抑制固体表面上的海洋生物污损的用途。
9.如权利要求8所述的用途，其中所述防污组合物与允许控制释放式IA和/或IB化合物的聚合物和/或共聚物组合使用。
10.一种防污涂料，其包含如权利要求1至7中任一项所述的防污组合物和允许控制释放式IA和/或IB化合物的聚合物和/或共聚物。
11.如权利要求10所述的防污涂料，其中式IA和/或IB化合物的含量为约1至约25wt％。
12.如权利要求10或11中任一项所述的防污涂料，其中所述一种或多种杀生物剂的总含量小于约30wt％。
13.如权利要求10至12中任一项所述的防污涂料，其中CuPT的总含量小于约10wt％。
14.一种用于抑制固体表面上的海洋生物污损的方法，其包括将如权利要求10至13中任一项所述的防污涂料施加到所述表面上。
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