OA12716A - Paint compositions comprising esters of rosin and process of production thereof. - Google Patents

Paint compositions comprising esters of rosin and process of production thereof. Download PDF

Info

Publication number: OA12716A
Authority: OA; OAPI
Prior art keywords: rosin; composition; paint; binder; paints
Prior art date: 2001-10-30

Application number

OA1200400124A

Other languages

English (en)

Inventor

Michel Gillard

Marcel Vos

Original Assignee

Sigma Coatings Bv

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2001-10-30

Filing date

2002-10-25

Publication date

2006-06-27

2002-10-25 Application filed by Sigma Coatings Bv filed Critical Sigma Coatings Bv

2006-06-27 Publication of OA12716A publication Critical patent/OA12716A/en

Links

RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 title claims abstract description 95
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 title claims abstract description 92
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 title claims abstract description 92
239000003973 paint Substances 0.000 title claims abstract description 72
239000000203 mixture Substances 0.000 title claims description 42
238000004519 manufacturing process Methods 0.000 title claims description 7
238000000034 method Methods 0.000 title description 14
230000008569 process Effects 0.000 title description 10
150000002148 esters Chemical class 0.000 title description 4
239000011230 binding agent Substances 0.000 claims abstract description 38
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000005103 alkyl silyl group Chemical group 0.000 claims 1
230000003373 anti-fouling effect Effects 0.000 abstract description 30
238000005498 polishing Methods 0.000 abstract description 12
-1 copper acrylates Chemical class 0.000 description 35
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 18
239000000049 pigment Substances 0.000 description 17
239000002253 acid Substances 0.000 description 12
BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 11
KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 11
229940112669 cuprous oxide Drugs 0.000 description 11
239000010949 copper Substances 0.000 description 9
125000001424 substituent group Chemical group 0.000 description 9
239000011701 zinc Substances 0.000 description 9
239000011787 zinc oxide Substances 0.000 description 9
MXODCLTZTIFYDV-UHFFFAOYSA-L zinc;1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylate Chemical compound [Zn+2].C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C([O-])=O.C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C([O-])=O MXODCLTZTIFYDV-UHFFFAOYSA-L 0.000 description 9
150000001875 compounds Chemical class 0.000 description 8
229910052802 copper Inorganic materials 0.000 description 8
239000013535 sea water Substances 0.000 description 8
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
150000003839 salts Chemical class 0.000 description 7
229910052725 zinc Inorganic materials 0.000 description 7
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 6
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 6
239000003139 biocide Substances 0.000 description 6
238000000576 coating method Methods 0.000 description 6
239000000243 solution Substances 0.000 description 6
239000008096 xylene Substances 0.000 description 6
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 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 5
150000001252 acrylic acid derivatives Chemical class 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
150000002894 organic compounds Chemical class 0.000 description 5
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 5
239000002023 wood Substances 0.000 description 5
PICXIOQBANWBIZ-UHFFFAOYSA-N zinc;1-oxidopyridine-2-thione Chemical compound [Zn+2].[O-]N1C=CC=CC1=S.[O-]N1C=CC=CC1=S PICXIOQBANWBIZ-UHFFFAOYSA-N 0.000 description 5
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
125000002843 carboxylic acid group Chemical group 0.000 description 4
239000008199 coating composition Substances 0.000 description 4
PDZKZMQQDCHTNF-UHFFFAOYSA-M copper(1+);thiocyanate Chemical compound [Cu+].[S-]C#N PDZKZMQQDCHTNF-UHFFFAOYSA-M 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000011521 glass Substances 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
239000011347 resin Substances 0.000 description 4
229920005989 resin Polymers 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
229940043810 zinc pyrithione Drugs 0.000 description 4
AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 3
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 3
239000005749 Copper compound Substances 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 3
230000001070 adhesive effect Effects 0.000 description 3
239000002519 antifouling agent Substances 0.000 description 3
125000003710 aryl alkyl group Chemical group 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
239000011248 coating agent Substances 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 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 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
238000007654 immersion Methods 0.000 description 3
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 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
AZHVQJLDOFKHPZ-UHFFFAOYSA-N oxathiazine Chemical class O1SN=CC=C1 AZHVQJLDOFKHPZ-UHFFFAOYSA-N 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
MHVJRKBZMUDEEV-APQLOABGSA-N (+)-Pimaric acid Chemical compound [C@H]1([C@](CCC2)(C)C(O)=O)[C@@]2(C)[C@H]2CC[C@](C=C)(C)C=C2CC1 MHVJRKBZMUDEEV-APQLOABGSA-N 0.000 description 2
125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 description 2
FMYSHKHSQFXYRS-UHFFFAOYSA-N 1,4,2-oxathiazine Chemical class O1C=CSC=N1 FMYSHKHSQFXYRS-UHFFFAOYSA-N 0.000 description 2
QRNATDQRFAUDKF-UHFFFAOYSA-N 2-carbamothioylsulfanylethyl carbamodithioate Chemical compound NC(=S)SCCSC(N)=S QRNATDQRFAUDKF-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
FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 2
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
241000238586 Cirripedia Species 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
239000004593 Epoxy Substances 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 2
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
235000008331 Pinus X rigitaeda Nutrition 0.000 description 2
235000011613 Pinus brutia Nutrition 0.000 description 2
241000018646 Pinus brutia Species 0.000 description 2
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
230000008901 benefit Effects 0.000 description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
239000013626 chemical specie Substances 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
150000001880 copper compounds Chemical class 0.000 description 2
238000005336 cracking Methods 0.000 description 2
230000007547 defect Effects 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000011156 evaluation Methods 0.000 description 2
239000003925 fat Substances 0.000 description 2
238000009472 formulation Methods 0.000 description 2
239000013505 freshwater Substances 0.000 description 2
125000002541 furyl group Chemical group 0.000 description 2
125000001475 halogen functional group Chemical group 0.000 description 2
230000009931 harmful effect Effects 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
125000001183 hydrocarbyl group Chemical group 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
150000002484 inorganic compounds Chemical class 0.000 description 2
229910010272 inorganic material Inorganic materials 0.000 description 2
238000002386 leaching Methods 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000003921 oil Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000000123 paper Substances 0.000 description 2
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 2
241000894007 species Species 0.000 description 2
IPEHJNRNYPOFII-AZUAARDMSA-N sugiol Chemical compound CC([C@@H]1CC2=O)(C)CCC[C@]1(C)C1=C2C=C(C(C)C)C(O)=C1 IPEHJNRNYPOFII-AZUAARDMSA-N 0.000 description 2
125000001544 thienyl group Chemical group 0.000 description 2
KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 2
239000004408 titanium dioxide Substances 0.000 description 2
150000003918 triazines Chemical class 0.000 description 2
229940100888 zinc compound Drugs 0.000 description 2
JVVXZOOGOGPDRZ-UHFFFAOYSA-N (1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl)methanamine Chemical compound NCC1(C)CCCC2(C)C3=CC=C(C(C)C)C=C3CCC21 JVVXZOOGOGPDRZ-UHFFFAOYSA-N 0.000 description 1
JKBKXKTXDKYEOR-UHZRXMQZSA-N (1R,4aR,4bS,7S,10aR)-7-ethenyl-1,4a,7-trimethyl-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthrene-1-carbaldehyde Chemical compound O=C[C@]1(C)CCC[C@]2(C)[C@H]3CC[C@](C=C)(C)C=C3CC[C@H]21 JKBKXKTXDKYEOR-UHZRXMQZSA-N 0.000 description 1
VJILEYKNALCDDV-OIISXLGYSA-N (1S,4aS,10aR)-1,2,3,4,4a,9,10,10a-octahydro-6-hydroxy-1,4a-dimethylphenanthrene-1-carboxylic acid Chemical compound C1=C(O)C=C2[C@@]3(C)CCC[C@@](C(O)=O)(C)[C@@H]3CCC2=C1 VJILEYKNALCDDV-OIISXLGYSA-N 0.000 description 1
RSWGJHLUYNHPMX-OZNCTZQZSA-N (1r)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCC[C@@]2(C)C(O)=O RSWGJHLUYNHPMX-OZNCTZQZSA-N 0.000 description 1
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YPGLTKHJEQHKSS-ASZLNGMRSA-N (1r,4ar,4bs,7r,8as,10ar)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthrene-1-carboxylic acid Chemical compound [C@H]1([C@](CCC2)(C)C(O)=O)[C@@]2(C)[C@H]2CC[C@@H](C(C)C)C[C@@H]2CC1 YPGLTKHJEQHKSS-ASZLNGMRSA-N 0.000 description 1
IGGWKHQYMAJOHK-HHUCQEJWSA-N (3r,4ar,6as,10as,10br)-3-ethenyl-3,4a,7,7,10a-pentamethyl-2,5,6,6a,8,9,10,10b-octahydro-1h-benzo[f]chromene Chemical compound O1[C@@](C)(C=C)CC[C@@H]2[C@@]3(C)CCCC(C)(C)[C@@H]3CC[C@]21C IGGWKHQYMAJOHK-HHUCQEJWSA-N 0.000 description 1
KVTOPOITUALWOF-AZUAARDMSA-N (4as,10as)-6-hydroxy-1,1,4a-trimethyl-7-propan-2-yl-2,3,4,10a-tetrahydrophenanthrene-9,10-dione Chemical compound CC([C@@H]1C(=O)C2=O)(C)CCC[C@]1(C)C1=C2C=C(C(C)C)C(O)=C1 KVTOPOITUALWOF-AZUAARDMSA-N 0.000 description 1
ADDAJJNRBDCPFR-UHFFFAOYSA-N (5-thiocyanatothiophen-2-yl) thiocyanate Chemical compound N#CSC1=CC=C(SC#N)S1 ADDAJJNRBDCPFR-UHFFFAOYSA-N 0.000 description 1
125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 description 1
125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 description 1
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UOZNXGJVAWDLQK-UHFFFAOYSA-N 1-(2,3-dimethylphenyl)pyrrole-2,5-dione Chemical compound CC1=CC=CC(N2C(C=CC2=O)=O)=C1C UOZNXGJVAWDLQK-UHFFFAOYSA-N 0.000 description 1
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
TUPMGRKCIDFTPF-UHFFFAOYSA-N 1-(2-anilinophenyl)pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1NC1=CC=CC=C1 TUPMGRKCIDFTPF-UHFFFAOYSA-N 0.000 description 1
BMBNUKLPUDEUNP-UHFFFAOYSA-N 1-(2-phenylphenyl)-2,3-dihydro-1H-indene Chemical group C1CC2=CC=CC=C2C1C1=CC=CC=C1C1=CC=CC=C1 BMBNUKLPUDEUNP-UHFFFAOYSA-N 0.000 description 1
QDEQBRUNBFJJPW-UHFFFAOYSA-N 1-(3-chlorophenyl)pyrrole-2,5-dione Chemical compound ClC1=CC=CC(N2C(C=CC2=O)=O)=C1 QDEQBRUNBFJJPW-UHFFFAOYSA-N 0.000 description 1
YLJPMCJDTAPPRX-UHFFFAOYSA-N 1-(4-butylphenyl)pyrrole-2,5-dione Chemical compound C1=CC(CCCC)=CC=C1N1C(=O)C=CC1=O YLJPMCJDTAPPRX-UHFFFAOYSA-N 0.000 description 1
KCFXNGDHQPMIAQ-UHFFFAOYSA-N 1-(4-methylphenyl)pyrrole-2,5-dione Chemical compound C1=CC(C)=CC=C1N1C(=O)C=CC1=O KCFXNGDHQPMIAQ-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
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
ONVABDHFQKWOSV-UHFFFAOYSA-N 16-Phyllocladene Natural products C1CC(C2)C(=C)CC32CCC2C(C)(C)CCCC2(C)C31 ONVABDHFQKWOSV-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
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
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238000010998 test method Methods 0.000 description 1
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
229960002447 thiram Drugs 0.000 description 1
230000009974 thixotropic effect Effects 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
125000004953 trihalomethyl group Chemical group 0.000 description 1
MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical compound C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000004246 zinc acetate Substances 0.000 description 1
RKQOSDAEEGPRER-UHFFFAOYSA-L zinc diethyldithiocarbamate Chemical compound [Zn+2].CCN(CC)C([S-])=S.CCN(CC)C([S-])=S RKQOSDAEEGPRER-UHFFFAOYSA-L 0.000 description 1
229960001296 zinc oxide Drugs 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
239000011686 zinc sulphate Substances 0.000 description 1
235000009529 zinc sulphate Nutrition 0.000 description 1
JRPGMCRJPQJYPE-UHFFFAOYSA-N zinc;carbanide Chemical group [CH3-].[CH3-].[Zn+2] JRPGMCRJPQJYPE-UHFFFAOYSA-N 0.000 description 1
NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-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
- 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
- C09D5/1637—Macromolecular compounds
- 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

Landscapes

Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Wood Science & Technology (AREA)
Organic Chemistry (AREA)
Paints Or Removers (AREA)
Compositions Of Macromolecular Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Saccharide Compounds (AREA)
Inks, Pencil-Leads, Or Crayons (AREA)
Macromonomer-Based Addition Polymer (AREA)

OA1200400124A 2001-10-30 2002-10-25 Paint compositions comprising esters of rosin and process of production thereof. OA12716A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
EP01204141A EP1308484A1 (de)	2001-10-30	2001-10-30	Verwendung von Kolophonium-silylester in selbstpolierenden, fäulnisverhindernden Anstrichen

Publications (1)

Publication Number	Publication Date
OA12716A true OA12716A (en)	2006-06-27

Family

ID=8181160

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200400124A OA12716A (en)	2001-10-30	2002-10-25	Paint compositions comprising esters of rosin and process of production thereof.

Country Status (19)

Country	Link
US (1)	US7118616B2 (de)
EP (2)	EP1308484A1 (de)
JP (1)	JP4388813B2 (de)
KR (1)	KR100893742B1 (de)
CN (1)	CN1286925C (de)
AT (1)	ATE325167T1 (de)
BR (1)	BR0213559A (de)
CA (1)	CA2462927A1 (de)
DE (1)	DE60211205T2 (de)
DK (1)	DK1448723T3 (de)
EG (1)	EG23246A (de)
ES (1)	ES2262862T3 (de)
HR (1)	HRP20040434B1 (de)
MY (1)	MY128025A (de)
NO (1)	NO20041614L (de)
OA (1)	OA12716A (de)
PL (1)	PL208369B1 (de)
WO (1)	WO2003037999A1 (de)
ZA (1)	ZA200402973B (de)

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EP1475415A1 (de)	2003-05-07	2004-11-10	SigmaKalon Services B.V.	Silylester, ihre Verwendung in Bindemittelsystemen und Lackzusammensetzungen, und Verfahren zu ihrer Herstellung
EP1641862B1 (de) *	2003-07-07	2006-11-15	Akzo Nobel Coatings International B.V.	Silylestercopolymerzusammensetzungen
KR100880841B1 (ko) *	2007-04-02	2009-02-02	부산대학교 산학협력단	방오 도료 조성물
FR2952067B1 (fr) *	2009-11-03	2012-05-25	Saint Gobain Technical Fabrics	Composition filmogene renfermant un agent apte a pieger le formaldehyde
EP2542629B1 (de) *	2010-03-02	2020-12-02	Aerogel ApS	Geladene gelpartikel für bewuchshemmende zusammensetzungen
CN102051101B (zh) *	2010-11-18	2012-07-04	浙江大学	一种常温固化防污减阻水凝胶软涂层的制备方法
EP2753665A4 (de) *	2011-09-06	2015-05-20	Hempel As	Selbstpolierende bewuchshemmende lackzusammensetzung mit festpartikeln eingeschlossener oder verkapselter harzbestandteile
DK2785804T3 (en)	2011-12-02	2016-02-29	Akzo Nobel Coatings Int Bv	WATER-BASED GROUNDING PREVENTION COATING COMPOSITION
JP6135861B2 (ja) *	2013-02-15	2017-05-31	荒川化学工業株式会社	コーティング組成物
JP5887331B2 (ja) *	2013-12-27	2016-03-16	株式会社タムラ製作所	はんだ組成物
EP3783073B1 (de) *	2018-04-20	2022-08-03	Nitto Kasei Co., Ltd.	Bewuchshemmende beschichtungszusammensetzung
JP7785373B2 (ja) *	2021-03-12	2025-12-15	日東化成株式会社	防汚塗料組成物

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GB2007691A (en) *	1977-10-21	1979-05-23	Carter B	Printing ink
EP0131621B1 (de)	1983-01-17	1987-09-30	Hydril Company	Rohrverbindung mit zwischenliegender metall-gegen-metall-dichtung
NZ206852A (en)	1983-01-17	1987-02-20	M & T Chemicals Inc	Erodable marine anti-fouling paint containing acrylic or methacrylic ester-based copolymer
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KR970000998B1 (ko)	1987-06-28	1997-01-25	닛뽄유시 가부시끼가이샤	방오용 페인트
GB9008053D0 (en)	1990-04-10	1990-06-06	Courtaulds Coatings Ltd	Coating compositions
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US5545823A (en) *	1991-06-11	1996-08-13	Yung Chi Paint & Varnish Mfg. Co., Ltd.	Self-polishing type antifouling coating composition containing film-formable metal soap compound
GB2257154B (en) *	1991-06-26	1995-09-06	Yung Chi Paint & Varnish Mfg C	Antifouling coating composition comprising a polymerisable metal soap
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US20030162924A1 (en) *	2000-02-25	2003-08-28	Marcel Vos	Metal-free binders for self-polishing antifouling paints
US6710117B2 (en) *	2000-02-25	2004-03-23	Sigma Coatings B.V.	Marine paint compositions
SG97209A1 (en) *	2000-10-25	2003-07-18	Chugoku Marine Paints	Novel (poly) oxyalkylene block silyl ester copolymer, antifouling coating composition, antifouling coating formed from antifouling coating composition, antifouling method using antifouling coating composition and hull or underwater structure covered with antifouling coating
ES2265060T3 (es) *	2001-12-20	2007-02-01	Hempel A/S	Composicion de pintura antiincrustante con base de dispersion no acuosa.

2001
- 2001-10-30 EP EP01204141A patent/EP1308484A1/de not_active Withdrawn
2002
- 2002-10-25 PL PL369794A patent/PL208369B1/pl not_active IP Right Cessation
- 2002-10-25 BR BR0213559-0A patent/BR0213559A/pt not_active IP Right Cessation
- 2002-10-25 CN CNB028217322A patent/CN1286925C/zh not_active Expired - Fee Related
- 2002-10-25 ES ES02781288T patent/ES2262862T3/es not_active Expired - Lifetime
- 2002-10-25 AT AT02781288T patent/ATE325167T1/de not_active IP Right Cessation
- 2002-10-25 HR HR20040434A patent/HRP20040434B1/xx not_active IP Right Cessation
- 2002-10-25 CA CA002462927A patent/CA2462927A1/en not_active Abandoned
- 2002-10-25 WO PCT/EP2002/011957 patent/WO2003037999A1/en not_active Ceased
- 2002-10-25 KR KR1020047006429A patent/KR100893742B1/ko not_active Expired - Fee Related
- 2002-10-25 JP JP2003540266A patent/JP4388813B2/ja not_active Expired - Lifetime
- 2002-10-25 US US10/492,766 patent/US7118616B2/en not_active Expired - Fee Related
- 2002-10-25 DE DE60211205T patent/DE60211205T2/de not_active Expired - Lifetime
- 2002-10-25 OA OA1200400124A patent/OA12716A/en unknown
- 2002-10-25 EP EP02781288A patent/EP1448723B1/de not_active Expired - Lifetime
- 2002-10-25 DK DK02781288T patent/DK1448723T3/da active
- 2002-10-29 MY MYPI20024058A patent/MY128025A/en unknown
- 2002-10-30 EG EG2002101189A patent/EG23246A/xx active
2004
- 2004-04-19 ZA ZA200402973A patent/ZA200402973B/en unknown
- 2004-04-20 NO NO20041614A patent/NO20041614L/no unknown

Also Published As

Publication number	Publication date
NO20041614L (no)	2004-04-20
EP1308484A1 (de)	2003-05-07
JP4388813B2 (ja)	2009-12-24
BR0213559A (pt)	2004-10-26
PL369794A1 (en)	2005-05-02
ZA200402973B (en)	2005-01-13
PL208369B1 (pl)	2011-04-29
DE60211205T2 (de)	2006-10-26
HRP20040434B1 (en)	2008-06-30
EP1448723A1 (de)	2004-08-25
CN1286925C (zh)	2006-11-29
KR20040062954A (ko)	2004-07-09
EG23246A (en)	2004-09-29
ES2262862T3 (es)	2006-12-01
KR100893742B1 (ko)	2009-04-17
HK1066822A1 (en)	2005-04-01
HRP20040434A2 (en)	2004-08-31
WO2003037999A1 (en)	2003-05-08
ATE325167T1 (de)	2006-06-15
DK1448723T3 (da)	2006-09-04
US20050131099A1 (en)	2005-06-16
EP1448723B1 (de)	2006-05-03
CN1578816A (zh)	2005-02-09
US7118616B2 (en)	2006-10-10
MY128025A (en)	2007-01-31
JP2005507450A (ja)	2005-03-17
CA2462927A1 (en)	2003-05-08
DE60211205D1 (de)	2006-06-08

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US8148446B2 (en)	2012-04-03	Silyl esters, their use in binder systems and paint compositions and a process of production thereof
EP3710539B1 (de)	2024-06-12	Antifouling zusammensetzung
FI102290B (fi)	1998-11-13	Kasvittumista estävä päällystekoostumus
JP2023089170A (ja)	2023-06-27	防汚組成物
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AU2002349007A1 (en)	2003-05-12	Paint Compositions comprising esters of rosin and process of production thereof
HK1066822B (en)	2006-09-22	Paint compositions comprising esters of rosin and process of production thereof
JPH10298454A (ja)	1998-11-10	防汚塗料組成物
JP2010159432A (ja)	2010-07-22	防汚塗料