DK172213B1 - Flydende overtrækspræparat baseret på et polyacetoacetat og en polyamin samt anvendelse af overtrækspræparat som overtræk på et substrat - Google Patents
Flydende overtrækspræparat baseret på et polyacetoacetat og en polyamin samt anvendelse af overtrækspræparat som overtræk på et substrat Download PDFInfo
- Publication number
- DK172213B1 DK172213B1 DK138686A DK138686A DK172213B1 DK 172213 B1 DK172213 B1 DK 172213B1 DK 138686 A DK138686 A DK 138686A DK 138686 A DK138686 A DK 138686A DK 172213 B1 DK172213 B1 DK 172213B1
- Authority
- DK
- Denmark
- Prior art keywords
- polyacetoacetate
- parts
- coating composition
- polyamine
- acetoacetate
- Prior art date
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- 239000011248 coating agent Substances 0.000 title claims abstract description 39
- 238000000576 coating method Methods 0.000 title claims abstract description 39
- 239000008199 coating composition Substances 0.000 title claims abstract description 36
- 229920000768 polyamine Polymers 0.000 title claims abstract description 23
- 239000007788 liquid Substances 0.000 title claims abstract description 6
- 239000000758 substrate Substances 0.000 title claims abstract description 5
- -1 hydroxyalkyl acrylate Chemical compound 0.000 claims abstract description 39
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical group CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 claims abstract description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 18
- 230000009477 glass transition Effects 0.000 claims abstract description 12
- 229920000642 polymer Polymers 0.000 claims abstract description 11
- 150000002576 ketones Chemical class 0.000 claims abstract description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 8
- 150000002148 esters Chemical class 0.000 claims abstract description 7
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims abstract description 6
- 150000001299 aldehydes Chemical class 0.000 claims abstract description 4
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 claims description 7
- 229940093858 ethyl acetoacetate Drugs 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 3
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 claims description 2
- 239000001294 propane Substances 0.000 claims description 2
- OELQSSWXRGADDE-UHFFFAOYSA-N 2-methylprop-2-eneperoxoic acid Chemical compound CC(=C)C(=O)OO OELQSSWXRGADDE-UHFFFAOYSA-N 0.000 claims 1
- 150000004808 allyl alcohols Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 26
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 abstract description 8
- 238000000034 method Methods 0.000 abstract 1
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- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 5
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- 125000005395 methacrylic acid group Chemical group 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
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- 238000006243 chemical reaction Methods 0.000 description 4
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
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- IGSBHTZEJMPDSZ-UHFFFAOYSA-N 4-[(4-amino-3-methylcyclohexyl)methyl]-2-methylcyclohexan-1-amine Chemical compound C1CC(N)C(C)CC1CC1CC(C)C(N)CC1 IGSBHTZEJMPDSZ-UHFFFAOYSA-N 0.000 description 3
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- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
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- YOOSAIJKYCBPFW-UHFFFAOYSA-N 3-[4-(3-aminopropoxy)butoxy]propan-1-amine Chemical compound NCCCOCCCCOCCCN YOOSAIJKYCBPFW-UHFFFAOYSA-N 0.000 description 1
- PHNLANCZOOOBPJ-UHFFFAOYSA-N 3-[5-(3-aminopropoxy)pentoxy]propan-1-amine Chemical compound NCCCOCCCCCOCCCN PHNLANCZOOOBPJ-UHFFFAOYSA-N 0.000 description 1
- RHLVCLIPMVJYKS-UHFFFAOYSA-N 3-octanone Chemical compound CCCCCC(=O)CC RHLVCLIPMVJYKS-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
- ZHVYIZVNKGAJBE-UHFFFAOYSA-N 4-[2-(4-amino-3-methylcyclohexyl)propan-2-yl]-2-methylcyclohexan-1-amine Chemical compound C1CC(N)C(C)CC1C(C)(C)C1CC(C)C(N)CC1 ZHVYIZVNKGAJBE-UHFFFAOYSA-N 0.000 description 1
- BDBZTOMUANOKRT-UHFFFAOYSA-N 4-[2-(4-aminocyclohexyl)propan-2-yl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1C(C)(C)C1CCC(N)CC1 BDBZTOMUANOKRT-UHFFFAOYSA-N 0.000 description 1
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 1
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 1
- RBHIUNHSNSQJNG-UHFFFAOYSA-N 6-methyl-3-(2-methyloxiran-2-yl)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2(C)OC2CC1C1(C)CO1 RBHIUNHSNSQJNG-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
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- 239000000020 Nitrocellulose Substances 0.000 description 1
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- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- ASAPXSLRMDUMFX-QXMHVHEDSA-N [(z)-octadec-9-enyl] prop-2-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCCOC(=O)C=C ASAPXSLRMDUMFX-QXMHVHEDSA-N 0.000 description 1
- 150000004729 acetoacetic acid derivatives Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- YBCVMFKXIKNREZ-UHFFFAOYSA-N acoh acetic acid Chemical compound CC(O)=O.CC(O)=O YBCVMFKXIKNREZ-UHFFFAOYSA-N 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- GJOSRMAVDXJBCZ-UHFFFAOYSA-N cyclohexyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC1CCCCC1 GJOSRMAVDXJBCZ-UHFFFAOYSA-N 0.000 description 1
- XXKOQQBKBHUATC-UHFFFAOYSA-N cyclohexylmethylcyclohexane Chemical compound C1CCCCC1CC1CCCCC1 XXKOQQBKBHUATC-UHFFFAOYSA-N 0.000 description 1
- JDPQWHLMBJZURR-UHFFFAOYSA-N decan-5-one Chemical compound CCCCCC(=O)CCCC JDPQWHLMBJZURR-UHFFFAOYSA-N 0.000 description 1
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 1
- ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- BQQUFAMSJAKLNB-UHFFFAOYSA-N dicyclopentadiene diepoxide Chemical compound C12C(C3OC33)CC3C2CC2C1O2 BQQUFAMSJAKLNB-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 125000004185 ester group Chemical group 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
- 125000001033 ether group Chemical group 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- VLCAYQIMSMPEBW-UHFFFAOYSA-N methyl 3-hydroxy-2-methylidenebutanoate Chemical compound COC(=O)C(=C)C(C)O VLCAYQIMSMPEBW-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ZAJNGDIORYACQU-UHFFFAOYSA-N methyl n-octyl ketone Natural products CCCCCCCCC(C)=O ZAJNGDIORYACQU-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- KMBPCQSCMCEPMU-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)CCCN KMBPCQSCMCEPMU-UHFFFAOYSA-N 0.000 description 1
- ITZPOSYADVYECJ-UHFFFAOYSA-N n'-cyclohexylpropane-1,3-diamine Chemical compound NCCCNC1CCCCC1 ITZPOSYADVYECJ-UHFFFAOYSA-N 0.000 description 1
- QHJABUZHRJTCAR-UHFFFAOYSA-N n'-methylpropane-1,3-diamine Chemical compound CNCCCN QHJABUZHRJTCAR-UHFFFAOYSA-N 0.000 description 1
- PSCWDXZBRYGBDI-UHFFFAOYSA-N n-(oxiran-2-ylmethyl)prop-2-enamide Chemical group C=CC(=O)NCC1CO1 PSCWDXZBRYGBDI-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229940117969 neopentyl glycol Drugs 0.000 description 1
- 125000004971 nitroalkyl group Chemical group 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 1
- MVDYEFQVZNBPPH-UHFFFAOYSA-N pentane-2,3,4-trione Chemical compound CC(=O)C(=O)C(C)=O MVDYEFQVZNBPPH-UHFFFAOYSA-N 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
- 229920001568 phenolic resin Polymers 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- PFENPVAFZTUOOM-UHFFFAOYSA-N phenyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC1=CC=CC=C1 PFENPVAFZTUOOM-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- AXLMPTNTPOWPLT-UHFFFAOYSA-N prop-2-enyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCC=C AXLMPTNTPOWPLT-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
- C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
- Optical Fibers, Optical Fiber Cores, And Optical Fiber Bundles (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Medicinal Preparation (AREA)
- Non-Metallic Protective Coatings For Printed Circuits (AREA)
- Steroid Compounds (AREA)
- Saccharide Compounds (AREA)
- Sampling And Sample Adjustment (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL8500953 | 1985-03-29 | ||
| NL8500953 | 1985-03-29 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK138686D0 DK138686D0 (da) | 1986-03-25 |
| DK138686A DK138686A (da) | 1986-09-30 |
| DK172213B1 true DK172213B1 (da) | 1998-01-05 |
Family
ID=19845770
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK138686A DK172213B1 (da) | 1985-03-29 | 1986-03-25 | Flydende overtrækspræparat baseret på et polyacetoacetat og en polyamin samt anvendelse af overtrækspræparat som overtræk på et substrat |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4772680A (enExample) |
| EP (1) | EP0199087B2 (enExample) |
| JP (1) | JPS61252274A (enExample) |
| CN (1) | CN1007259B (enExample) |
| AT (1) | ATE40142T1 (enExample) |
| AU (1) | AU580400B2 (enExample) |
| BR (1) | BR8601355A (enExample) |
| CA (1) | CA1268890C (enExample) |
| DE (1) | DE3661834D1 (enExample) |
| DK (1) | DK172213B1 (enExample) |
| ES (1) | ES8708002A1 (enExample) |
| FI (1) | FI80467C (enExample) |
| GR (1) | GR860835B (enExample) |
| NO (1) | NO175007C (enExample) |
| ZA (1) | ZA862357B (enExample) |
Families Citing this family (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0331829A1 (en) * | 1988-03-10 | 1989-09-13 | The Dow Chemical Company | Chelation resins and their preparation |
| US4708821A (en) * | 1985-03-27 | 1987-11-24 | Hoechst Gosei Kabushiki Kaisha | Process for preparing aqueous gel and use thereof |
| ATE46712T1 (de) * | 1985-03-29 | 1989-10-15 | Akzo Nv | Fluessige ueberzugszusammensetzung und verfahren zum ueberziehen von substraten damit. |
| EP0262720B1 (en) * | 1986-09-24 | 1991-04-24 | Akzo N.V. | An aqueous coating composition and a process of coating a substrate with such coating composition |
| DE3767274D1 (de) * | 1986-09-24 | 1991-02-14 | Akzo Nv | Waesserige ueberzugszusammensetzung und verfahren zum ueberziehen eines substrats damit. |
| ES2046291T3 (es) * | 1988-02-01 | 1994-02-01 | Rohm And Haas Company | Metodo de reaccion de dos componentes, composiciones, composiciones de recubrimientos y sus usos. |
| EP0360037B1 (de) * | 1988-09-19 | 1994-11-17 | Siemens Aktiengesellschaft | Dämpfungsmasse für Oberflächen-wellenbauelemente |
| DE3832958A1 (de) * | 1988-09-28 | 1990-04-12 | Basf Lacke & Farben | Haertbare zusammensetzung auf basis eines michael-additionsproduktes, verfahren zu seiner herstellung sowie seine verwendung |
| ES2060929T3 (es) * | 1989-06-09 | 1994-12-01 | Akzo Nobel Nv | Composicion de revestimiento liquida que incluye, como agente de reticulacion, una amina monoprimaria no bloqueada. |
| DE3932517A1 (de) * | 1989-09-29 | 1991-04-11 | Herberts Gmbh | Bindemittelzusammensetzung und deren verwendung in ueberzugsmitteln |
| US5021537A (en) * | 1990-04-27 | 1991-06-04 | Shell Oil Company | Polyacetoacetate-containing epoxy resin compositions |
| US5589534A (en) * | 1990-10-16 | 1996-12-31 | Akzo Nobel N.V. | Aqueous coating compositions including a reactive emulsifier |
| DE4032751A1 (de) * | 1990-10-16 | 1992-04-23 | Hoechst Ag | Fluessiges beschichtungsmittel |
| DE4137613A1 (de) * | 1991-11-15 | 1993-05-19 | Herberts Gmbh | Bindemittelzusammensetzung, diese enthaltende ueberzugsmittel und deren verwendung |
| US5288804A (en) * | 1992-01-03 | 1994-02-22 | Reichhold Chemicals, Inc. | Acetoacetate aromatic aldimine resin composition |
| US5391624A (en) * | 1992-02-10 | 1995-02-21 | S. C. Johnson & Son, Inc. | Thermosettable compositions |
| DE4210333A1 (de) * | 1992-03-30 | 1993-10-07 | Hoechst Ag | Flüssiges Beschichtungsmittel |
| MY108731A (en) * | 1992-04-16 | 1996-11-30 | Akzo Nv | Aqueous coating compositions |
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-
1986
- 1986-03-19 EP EP86103739A patent/EP0199087B2/en not_active Expired - Lifetime
- 1986-03-19 DE DE8686103739T patent/DE3661834D1/de not_active Expired
- 1986-03-19 AT AT86103739T patent/ATE40142T1/de not_active IP Right Cessation
- 1986-03-25 NO NO861223A patent/NO175007C/no not_active IP Right Cessation
- 1986-03-25 DK DK138686A patent/DK172213B1/da not_active IP Right Cessation
- 1986-03-26 ES ES553477A patent/ES8708002A1/es not_active Expired
- 1986-03-26 BR BR8601355A patent/BR8601355A/pt not_active IP Right Cessation
- 1986-03-26 US US06/844,413 patent/US4772680A/en not_active Expired - Lifetime
- 1986-03-26 CA CA505214A patent/CA1268890C/en not_active Expired - Lifetime
- 1986-03-27 AU AU55367/86A patent/AU580400B2/en not_active Expired
- 1986-03-27 ZA ZA862357A patent/ZA862357B/xx unknown
- 1986-03-27 FI FI861347A patent/FI80467C/fi not_active IP Right Cessation
- 1986-03-28 CN CN86102064A patent/CN1007259B/zh not_active Expired
- 1986-03-28 GR GR860835A patent/GR860835B/el unknown
- 1986-03-28 JP JP61068830A patent/JPS61252274A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FI861347A0 (fi) | 1986-03-27 |
| EP0199087A1 (en) | 1986-10-29 |
| BR8601355A (pt) | 1986-12-02 |
| ES553477A0 (es) | 1987-09-16 |
| DK138686D0 (da) | 1986-03-25 |
| EP0199087B1 (en) | 1989-01-18 |
| JPH0220677B2 (enExample) | 1990-05-10 |
| JPS61252274A (ja) | 1986-11-10 |
| EP0199087B2 (en) | 1993-11-10 |
| DK138686A (da) | 1986-09-30 |
| CA1268890A (en) | 1990-05-08 |
| CN1007259B (zh) | 1990-03-21 |
| ATE40142T1 (de) | 1989-02-15 |
| ES8708002A1 (es) | 1987-09-16 |
| NO175007C (no) | 1994-08-17 |
| ZA862357B (en) | 1986-11-26 |
| DE3661834D1 (en) | 1989-02-23 |
| CN86102064A (zh) | 1986-09-24 |
| NO861223L (no) | 1986-09-30 |
| FI861347L (fi) | 1986-09-30 |
| NO175007B (no) | 1994-05-09 |
| FI80467B (fi) | 1990-02-28 |
| AU5536786A (en) | 1986-10-02 |
| CA1268890C (en) | 1990-05-08 |
| GR860835B (en) | 1986-07-29 |
| FI80467C (fi) | 1990-06-11 |
| AU580400B2 (en) | 1989-01-12 |
| US4772680A (en) | 1988-09-20 |
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| B1 | Patent granted (law 1993) | ||
| PBP | Patent lapsed |
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