EP0956321A1 - Composition de rev tement pour des recipients alimentaires - Google Patents
Composition de rev tement pour des recipients alimentairesInfo
- Publication number
- EP0956321A1 EP0956321A1 EP97953778A EP97953778A EP0956321A1 EP 0956321 A1 EP0956321 A1 EP 0956321A1 EP 97953778 A EP97953778 A EP 97953778A EP 97953778 A EP97953778 A EP 97953778A EP 0956321 A1 EP0956321 A1 EP 0956321A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- weight
- coating composition
- water
- composition according
- coating
- 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.)
- Withdrawn
Links
- 239000008199 coating composition Substances 0.000 title claims abstract description 53
- 235000013305 food Nutrition 0.000 title claims abstract description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 28
- 229920002803 thermoplastic polyurethane Polymers 0.000 claims abstract description 26
- 229920001225 polyester resin Polymers 0.000 claims abstract description 23
- 239000004645 polyester resin Substances 0.000 claims abstract description 23
- 239000011230 binding agent Substances 0.000 claims abstract description 22
- 229920000642 polymer Polymers 0.000 claims abstract description 22
- 229920000058 polyacrylate Polymers 0.000 claims abstract description 16
- 238000004132 cross linking Methods 0.000 claims abstract description 13
- 239000003960 organic solvent Substances 0.000 claims abstract description 10
- 238000000576 coating method Methods 0.000 claims description 39
- 239000011248 coating agent Substances 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 21
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 19
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 17
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 12
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 4
- 229920000877 Melamine resin Polymers 0.000 claims description 4
- 238000006386 neutralization reaction Methods 0.000 claims description 4
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 4
- 239000000049 pigment Substances 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 239000000314 lubricant Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000004640 Melamine resin Substances 0.000 claims description 2
- 238000007334 copolymerization reaction Methods 0.000 claims description 2
- 150000007974 melamines Chemical class 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 239000005056 polyisocyanate Substances 0.000 description 18
- 229920001228 polyisocyanate Polymers 0.000 description 18
- 230000001954 sterilising effect Effects 0.000 description 14
- 238000004659 sterilization and disinfection Methods 0.000 description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- 229920005989 resin Polymers 0.000 description 11
- 239000011347 resin Substances 0.000 description 11
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 6
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 6
- -1 aliphatic dicarboxylic acids Chemical class 0.000 description 6
- 229960002887 deanol Drugs 0.000 description 6
- 239000012972 dimethylethanolamine Substances 0.000 description 6
- 238000009928 pasteurization Methods 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 229920003180 amino resin Polymers 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 230000007613 environmental effect Effects 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000000463 material Substances 0.000 description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical group NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 3
- 238000004806 packaging method and process Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 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
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- OMOVVBIIQSXZSZ-UHFFFAOYSA-N [6-(4-acetyloxy-5,9a-dimethyl-2,7-dioxo-4,5a,6,9-tetrahydro-3h-pyrano[3,4-b]oxepin-5-yl)-5-formyloxy-3-(furan-3-yl)-3a-methyl-7-methylidene-1a,2,3,4,5,6-hexahydroindeno[1,7a-b]oxiren-4-yl] 2-hydroxy-3-methylpentanoate Chemical compound CC12C(OC(=O)C(O)C(C)CC)C(OC=O)C(C3(C)C(CC(=O)OC4(C)COC(=O)CC43)OC(C)=O)C(=C)C32OC3CC1C=1C=COC=1 OMOVVBIIQSXZSZ-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000008186 active pharmaceutical agent Substances 0.000 description 2
- 230000000996 additive effect Effects 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
- 150000008064 anhydrides Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000002981 blocking agent Substances 0.000 description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical class CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 229920000578 graft copolymer Polymers 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 1
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 1
- GDXHBFHOEYVPED-UHFFFAOYSA-N 1-(2-butoxyethoxy)butane Chemical compound CCCCOCCOCCCC GDXHBFHOEYVPED-UHFFFAOYSA-N 0.000 description 1
- 150000000211 1-dodecanols Chemical class 0.000 description 1
- JLBXCKSMESLGTJ-UHFFFAOYSA-N 1-ethoxypropan-1-ol Chemical compound CCOC(O)CC JLBXCKSMESLGTJ-UHFFFAOYSA-N 0.000 description 1
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 description 1
- SZSSMFVYZRQGIM-UHFFFAOYSA-N 2-(hydroxymethyl)-2-propylpropane-1,3-diol Chemical compound CCCC(CO)(CO)CO SZSSMFVYZRQGIM-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- BNCADMBVWNPPIZ-UHFFFAOYSA-N 2-n,2-n,4-n,4-n,6-n,6-n-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound COCN(COC)C1=NC(N(COC)COC)=NC(N(COC)COC)=N1 BNCADMBVWNPPIZ-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 229920003270 Cymel® Polymers 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- 229920003264 Maprenal® Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 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
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001279 adipic acids Chemical class 0.000 description 1
- XPNGNIFUDRPBFJ-UHFFFAOYSA-N alpha-methylbenzylalcohol Natural products CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 238000006664 bond formation reaction Methods 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000002788 crimping Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical class OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006159 dianhydride group Chemical group 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 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
- 239000001530 fumaric acid Substances 0.000 description 1
- 150000002311 glutaric acids Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical class CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- 235000013980 iron oxide Nutrition 0.000 description 1
- VBMVTYDPPZVILR-UHFFFAOYSA-N iron(2+);oxygen(2-) Chemical class [O-2].[Fe+2] VBMVTYDPPZVILR-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000007774 longterm Effects 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
- 150000002689 maleic acids Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl 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])C([H])([H])[H] 0.000 description 1
- 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 1
- 150000002923 oximes Chemical class 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical class CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003330 sebacic acids Chemical class 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical group NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/06—Polyurethanes from polyesters
-
- 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
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/625—Polymers of alpha-beta ethylenically unsaturated carboxylic acids; hydrolyzed polymers of esters of these acids
- C08G18/6254—Polymers of alpha-beta ethylenically unsaturated carboxylic acids and of esters of these acids containing hydroxy groups
-
- 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
- C09D133/062—Copolymers with monomers not covered by C09D133/06
- C09D133/066—Copolymers with monomers not covered by C09D133/06 containing -OH groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
Definitions
- the invention relates to a coating composition for food containers, comprising a binder polymer from the group 'Water-soluble or water-dispersible polyester resin; water-soluble or water-dispersible acrylic polymer" or mixtures thereof, a crosslin ing resin, a solvent and, if desired, customary auxiliaries. Adjustment to a viscosity optimal for the processing of the coating composition can be made with the water and/or with the organic solvent. It is understood that the resulting binder polymer from the group 'Water-soluble or water-dispersible polyester resin; water-soluble or water-dispersible acrylic polymer" or mixtures thereof, a crosslin ing resin, a solvent and, if desired, customary auxiliaries. Adjustment to a viscosity optimal for the processing of the coating composition can be made with the water and/or with the organic solvent. It is understood that the resulting
- the binder polymer generally has a considerable number of OH groups capable of bond formation, by means of which, in conjunction with the crosslinking resin, it is possible to achieve crosslinking and, accordingly, curing.
- coatings produced from a coating composition are required to have particular properties.
- suitability for foods per se When used as an (external, for example) coating on food containers, such as cans, for example, suitability for foods per se must be accompanied by suitability for germ elimination stages in food processing, in particular for both interior and exterior can coatings.
- a germ elimination stage of this kind usually operates by pasteurization. In pasteurization, the contents (together with the container) are brought to temperatures in the range from 60°C to 80°C, but at any rate below 100°C, and are held at these temperatures for a certain time. By this means, microbes in the foods are damaged or killed. Pasteurization does not, however, lead to a microbe-free product but leads merely
- a can In a sterilization stage, for the purpose of virtually complete killing of microbes, a can is heated at temperatures of more than 120°C, in many cases even more than 130°C, for at least several minutes, for example 30 minutes. If a coating is to be exposed not to pasteurization but to a sterilization stage, then the coating must be so designed that
- the coatings must meet the particular requirements of the manufacturing processes of sheet-metal packaging, for example on Rutherford machines.
- the coatings are required to withstand shaping procedures such as folding, crimping, drawing, etc.
- they should be of high gloss, resistant to abrasion and readily printable, and should show good adhesion, a smooth surface texture (i.e. no craters) and a good humidity effect. What has been said applies especially in the case of use as a non-varnish exterior coating, i.e. without a final colourless protective coat.
- Food container coating compositions of the basic composition specified at the outset, albeit based on organic solvents, are known from the art.
- the resin used for curing the hydroxyl-containing binder polymer is a melamine or benzoguanamine resin.
- These known coating compositions have become well established in food technology, and indeed for containers including those subjected to a sterilization stage. On environmental protection grounds, and grounds of workplace safety, however, it is desirable to replace coating compositions comprising organic solvents by those comprising water as solvent.
- the document EP 0006336 Bl discloses a food container coating composition based on a hydroxyl-containing binder polymer which is likewise cured with an amino resin or phenolic resin, but which is aqueous. This known coating composition is suitable at best for pasteurization stages, but does not meet all requirements, especially with regard to hardness before and after sterilization stages.
- the document PCT EP90/00283 discloses a food container coating composition in which the curing of the hydroxyl-containing binder polymer takes place with the aid of blocked di- or polyisocyanates.
- Polyisocyanate resins are not employed for this purpose.
- the solvent is purely organic. Consequently, this known coating composition is subject to the environmental concerns already addressed above.
- the document DE-A 2507884 discloses aqueous coating composition based, inter alia, on hydroxyl-containing polymers which can be cured by means of blocked polyisocyanates. Polyisocyanate resins are not employed. These known coating compositions do not meet the requirements of the food industry from a technical standpoint, especially after exposure under sterilization conditions of the coatings produced therefrom.
- the documents DE 4421823 Al and EP 0358979B1 disclose aqueous coating compositions for the automotive industry which are based on hydroxyl-containing polymers that can be cured with polyisocyanates containing free NCO groups.
- the polyisocyanates are not resins.
- These coating compositions known from a different sector of technology, can in any case not be used for food containers in terms of their processing properties, the properties of the coatings produced therefrom, and, in particular, their food suitability.
- the coating technology is a different one.
- the invention is based on the technical problem of providing a coating composition with which it is possible to produce coatings which, even subsequent to sterilization stages, meet all requirements in terms of hardness, elasticity and water absorption behaviour but which nevertheless meet heightened environmental requirements through the use of water as solvent.
- a coating composition for food containers comprising a) 20-70% by weight of a binder polymer from the group 'Water-soluble or water-dispersible polyester resin; water-soluble or water- dispersible acrylic polymer" or mixtures thereof, b) 5-20% by weight of a crosslinking urethane resin which is virtually free from free NCO groups, c) 20-
- the coating composition can be completed by further additives, for example fillers.
- the invention is based on the surprising finding that, with the use of crosslinking urethane resins which per se are uncommon for the above-mentioned water-based binder polymers, and which are virtually free from free NCO groups, it is possible to provide a water-based coating composition which meets all requirements when the urethane resin is combined with the binder polymer in the manner indicated. This specific combination also, in particular, ensures sufficient crosslinking and thus sufficient hardness of the finished coating if the OH number and the content of NCO groups are within the stated ranges.
- Crosslinking urethane resins which are virtually free from free NCO groups are also referred to as blocked polyisocyanate resins.
- composition can, moreover, be applied particularly well with the Rutherford
- a novel coating composition produces a coating which meets all of the requirements despite the very short baking times in this case, for example 30 s (at a maximum article temperature of about 190°C).
- a particularly important advantage is that in conjunction with the above positive properties a coating produced from a novel coating composition, even after exposure to the severe conditions of sterilization stages, meets all requirements in terms of hardness, solvent resistance and adhesion (both to the
- the literature reference DE-A-4209248 does indeed disclose mixing a binder polymer with a crosslinking urethane resin which is virtually free from free NCO groups, the coating composition being obtained in aqueous solution or dispersion.
- the binder polymer is a very specific graft copolymer on
- invention is the complex and expensive preparation of the binder polymer.
- a novel coating composition preferably contains 25-35% by weight of the binder polymer, based on the solids content of the binder, 8-15% of urethane resin, 61- 34% of water, 1-15% by weight, preferably 5-15% by weight, of an organic solvent and 0.3-1% by weight of other auxiliaries.
- the novel coating composition can be designed in various ways in terms of the binder polymer.
- the polyester resin used can be an acrylic-modified, saturated polyester resin whose preparation is conducted with the proviso that the polyester resin has an OH number of 30 - 120 mg of KOH/g, preferably of 35 - 45 mg of KOH/g, and an acid number of 40 - 80 mg of KOH/g, preferably of 45 - 55 mg of KOH/g. It is advantageous if the polyester resin has a viscosity of 500 - 900 mPa.s, measured at 23°C and 50% by weight in butyl glycol as solvent.
- polyester resins examples include those from the group 'hydroxyl-containing polyesters, hydroxyl-containing acrylic-modified polyesters, hydroxyl-containing epoxy-modified polyesters" or mixtures thereof. They can also be employed, if desired, in combination with epoxy resins and/or hydroxyl- containing acrylate polymers or copolymers.
- the polyester resins are prepared, for example, by customary techniques of polyesterification reactions, by esterifying 9
- aromatic and/or aliphatic dicarboxylic acids dicarboxylic anhydrides, tricarboxylic anhydrides and/or tetracarboxylic mono- and dianhydrides with aliphatic, cyclo- aliphatic and/or aromatic mono-, di- and/or polyols.
- carboxylic acids suitable for the synthesis of the polyesters are phthalic, isophthalic, terephthalic, tetrahydrophthalic and hexahydrophthalic acids, dimethyl terephalate, trimellitic acid, trimellitic anhydride, adipic, azelaic, sebacic, maleic and glutaric acids and also dimeric and/or trimeric fatty acids.
- alcohol components which can be employed are aliphatic monools having 4 to 20 C atoms, 2,2-dimethyl-l,3- propanediol, ethylene glycol, diethylene glycol, 1,2- and 1,3-propylene glycol, butanediols, pentanediols, neopentyl glycol, hexane-diols, 2-methyl-l,5-pentane- diol, 2-ethyl-l,4-butane-diol, dimethylolcyclohexane, glycerol, trimethylol-ethane, trimethylolpropane, trimethylolbutane, pentaerythritol, dipentaerythritol, polycaprolactone-diols and -triols, and bisphenol A.
- the acrylic polymer employed can be one obtainable by using methacrylic acid and ethyl acrylate as starting materials, and styrene for copolymeriza-tion, and carrying out polymerization in the presence of butyl glycol and butanol.
- the acrylic polymer has an OH number of 10 - 100 mg of KOH/g, preferably of 25 - 35 mg of KOH/g, and a neutralization number of 40 - 100 mg of KOH/g, preferably of 65 - 75 mg of KOH/g.
- Acrylic polymers are essentially copolymers of acrylic esters with carboxyl-containing monomers. Examples of acrylic esters which can be used are esters of acrylic or methacrylic acid with methanol, ethanol, the butanols or ethylhexanol, or mixtures thereof, and esters with higher alcohols (having for example up to 20 C atoms).
- carboxyl-containing monomers which can be used are acrylic, methacrylic, crotonic, maleic or fumaric acid or mixtures thereof. Polymerization can also be carried out with further hydroxyl-containing compounds, such as esters of acrylic or methacrylic acid with ethanediol, propanediol or butanediol or reaction products of these acids with monoepoxide compounds or mixtures thereof.
- further suitable comonomers are styrene, methylstyrene, vinyltoluene, acrylamide, methacrylamide and the non-etherified or etherified N- methylol compounds thereof, or mixtures of these.
- Polymerization can be carried out using customary peroxy compounds as initiators, an example being tertiary-butyl peroxybenzoate.
- Organic solvents employed are, for example,. aliphatic, cycloaliphatic and aromatic hydrocarbons, esters, ethers and ketones, examples being butanol, xylene, various
- Shellsol® grades butyl glycol, ethylene glycol dibutyl ether, ethylene glycol diethyl
- ether ethylene glycol dimethyl ether, methyl ethyl ketone, methyl n-amyl ketone, diethyl ketone, ethyl butyl ketone, diisopropyl ketone, diisobutyl ketone, ⁇ acetylacetone, methyl acetate, ethyl acetate, propyl acetate, butyl acetate, amyl
- crosslinking urethane resin it is possible to employ blocked polyisocyanates based, for example, on polymerization products of monomeric diisocyanates having uretdione and/or biuret and/or isocyanurate and/or allophanate groups.
- blocked polyisocyanates it is possible to use any desired polyisocyanates in which the isocyanate groups have been reacted with a compound so that the blocked polyisocyanate formed is resistant at room temperature to hydroxyl and amino groups but reacts at elevated temperatures, generally in the range from about 80°C to about 300°C.
- In preparing the blocked polyisocyanates it is possible to use any organic polyisocyanates which are suitable for crosslinking.
- isocyanates which contain about 3 to 38, in particular about 8 to 15, carbon atoms.
- suitable diisocyanates are hexamethylene diisocyanate, 2,4- tolylene diisocyanate, 2,6-tolylene diisocyanate and l-isocyanatomethyl-5- isocyanato-l,3,3-trimethylcyclohexane.
- Polyisocyanates of higher isocyanate functionality can also be used. Examples of these are trimerized hexamethylene diisocyanate and trimerized isophorone diisocyanate. Mixtures of polyisocyanates can also be utilized.
- the organic polyisocyanates suitable as crosslinking agents in the context of the invention can also be prepolymers derived, for example, from a polyol, including a polyetherpolyol or a polyesterpolyol.
- alcohols such as methyl, ethyl, chloroethyl, propyl, butyl, amyl, hexyl, octyl, nonyl, 3,3,5-trimethylhexyl, decyl and lauryl alcohols; cycloaliphatic alcohols such as cyclopentanol and cyclohexanol; and aromatic alkyl alcohols, such as phenyl carbinol and methylphenyl carbinol.
- blocking agents are hydroxy amines, such as ethanolamine, oximes, such as methyl ethyl ketone oxime and acetone oxime, and aliphatic diamines,such as dibutylamine and diisopropylamine. In suitable proportions, these polyisocyanates and blocking agents can also be used to prepare the partially blocked polyisocyanates mentioned above.
- urethane resin preferably 30-70% of the amount of urethane resin employed, is replaced by amino resins, in particular a highly methylated melamine resin.
- Typical suitable amino resins are melamine, benzoguanamine and urea- formaldehyde resins. They are preferably used in a form etherified with lower alcohols, mostly methanol and/or butanol. Suitable amino resins are available commercially under the tradenames Cymel, Luwipal, Maprenal and Beetle, for example. Hexamethoxymethylmelamine, for example, is a suitable amino resin. / 2_
- novel coating composition can be formulated as a colourless, i.e. as
- a clearcoat or as a coloured coating material.
- a customary pigment is added to the coating composition, for example TiO 2 for a white coating material.
- a customary lubricant may be advisable as a further additive. Pigments and additives of this kind are referred to as auxiliaries.
- pigments examples being iron oxides, colorants on an inorganic or organic basis, bentonite, carbon black,
- auxiliaries can be added to the coating composition, examples being antifoams, stabilizers, plasticizers, light protection additives, etc.
- the invention also relates to the use of a novel coating composition according to Claim 8, to a process for preparing a novel coating composition according to Claim 9, and to a sterilizable can according to Claim 10.
- the can can be designed, in particular, as a two-piece can and/or may consist of sheet aluminium. Use for steel cans is likewise possible.
- the invention is illustrated on the basis of coating compositions which represent merely exemplary embodiments.
- Example 1 A novel coating composition was prepared from the following components: 27.96% by weight of an acrylic-modified saturated polyester resin, 9.32% by weight of butyl diglycol, 12.79% by weight of a crosslinking urethane resin which is virtually free from free NCO groups, 1.60% by weight of DMEA (dimethylethanolamine), 48.03%> by weight of demineralized water and 0.30% by weight of an auxiliary with the designation Additol XW 329 (silicone-containing coatings auxiliary, 50% strength in butyl glycol).
- the polyester resin employed has an OH number of about 40 mg of KOH/g and a neutralization number of about 50 mg of KOH/g and also a viscosity of about 700 mPa.s (the viscosity measured at 23°C and 50% by weight in butyl glycol as solvent) and is obtainable under the
- polyester resin relates to an 80% strength solution of the resin in ethoxypropanol/butyl glycol. This polyester resin is readily soluble in water.
- the urethane resin employed is a urethane baking resin based on hexamethylene
- This urethane resin is per se readily soluble only in organic solvents. It has an equivalent weight of about 378 and an NCO content of about 11.1% (blocked).
- the viscosity at 23°C and in accordance with DIN 53019/1 (75% strength in solvent naphtha 100) is about 3250 mPa.s. It is self-evident that the data given above and in the subsequent examples for the materials employed can be varied, it being possible for the variations in the numerical parameters to be up to 50% or more, provided the fundamental structural properties indicated are unchanged. Comparative experiments revealed that a coating of the above coating composition
- polyester/amino based coating (acrylate-modified, water-dilutable, saturated polyester resin/benzoguanamine resin): the hardness of the coating at 25°C after a sterilization stage at 129°C for 30 minutes was more than 4 H (film hardness in units of the hardness of customary commercial pencils) and was reduced virtually not at all relative to the initial hardness (customary coating: slight reduction by about 1 hardness unit).
- the hardness of the coating in hot water at 80°C after a sterilization stage at 129°C for 30 minutes was more than 2 H and was reduced relative to the initial hardness by only about 2 hardness units (customary coating: reduction by more than 6 hardness units).
- the solvent resistance (indicated as double strokes of a cotton wool pad soaked with MEK) after a sterilization stage at 129°C for 30 minutes was up to 60 DS (customary coating: about 6 DS).
- the polyester resin and also the urethane resin from Example 1 were employed.
- the proportion of the polyester resin was 32.40% by weight and that of the urethane resin 14.83% by weight. Additionally employed were: 0.40% by weight of Additol XW 329 (50% strength in butyl glycol), 7.62% by weight of butyl /S glycol, 8.51% by weight of butanol, 1.87% by weight of DMEA and 0.49% by
- BYK®-020 10% (antifoam for water-soluble systems, based on a
- Example 1 The product had a binder content of 37.04% by weight and a solids content of 37.29% by weight (0.25% by weight of solids from the additive). The proportion of water was 33.88% by weight, while the proportion of other solvents was likewise 33.88% by weight.
- Example 1 hardness relative to Example 1 while at the same time having greatly improved solvent resistance (MEK more than 80 after sterilization stage in accordance with Example 1).
- the third mixture is then added to the first mixture. 10% of the resulting first mixture are then added to the second mixture in a reactor. The temperature rises as a result of exothermic reaction and should be maintained within the range from 120°C to 129°C. The remainder of the first mixture is then metered into the contents of the reactor over 3 h at from 129°C to 131°C. 80 g of butyl glycol are added as the rinsing medium. Then the temperature is maintained at from 129°C to
- the substance A is a lubricant based on polyethylene glycol dioleate and is
- Variations of the acrylic polymer in terms of the OH number of 30 mg of KOH/g, in accordance with the above acrylic polymer, to more than 50 and from 75 to 100 mg of KOH/g showed that an increasing OH number leads to a rise in the viscosity of the coating composition, to a reduction in the hardness of the coating and to a reduction in the solvent resistance of the coating. From this it is evident that the OH number established should also not be too high.
- a coating produced with the above coating composition was subjected to the following test.
- An autoclave was preheated to 95°C.
- a metal panel bearing the coating was introduced into the autoclave and subjected to 1 1 of water (23°C).
- the autoclave was then run up to 125°C, where it was held for 30 minutes.
- the metal panel was then removed and the coating was assessed. Only very slight changes were evident in limited regions, and, moreover, these changes had completely disappeared again after 1 h.
- the coating meets all requirements with respect to hardness and solvent resistance as well.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Paints Or Removers (AREA)
Abstract
L'invention concerne une composition de revêtement pour des récipients alimentaires. Cette composition comprend: a) 20-40 % en poids d'un polymère de liaison dans le groupe 'résine de polyester soluble à l'eau ou dispersible dans l'eau; polymère acrylique soluble à l'eau ou dispersible dans l'eau'; b) 5-20 % en poids d'une résine d'uréthane réticulable qui est virtuellement dépourvue de groupes NCO libres; c) 20-70 % en poids d'eau; d) 0-18 % en poids d'un solvant organique et e) 0-5 % en poids d'auxiliaires. Le polymère de liaison comporte un nombre d'OH d'au moins 10 mg de KOH/g et la résine d'uréthane présente une teneur de NCO gropupes (bloqués) d'au moins 5 %.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19703091 | 1997-01-29 | ||
| DE19703091A DE19703091A1 (de) | 1997-01-29 | 1997-01-29 | Überzugsmittel für Nahrungsmittelbehälter |
| PCT/EP1997/006906 WO1998032807A1 (fr) | 1997-01-29 | 1997-12-10 | Composition de revêtement pour des recipients alimentaires |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0956321A1 true EP0956321A1 (fr) | 1999-11-17 |
Family
ID=7818607
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP97953778A Withdrawn EP0956321A1 (fr) | 1997-01-29 | 1997-12-10 | Composition de rev tement pour des recipients alimentaires |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0956321A1 (fr) |
| KR (1) | KR20000070606A (fr) |
| AU (1) | AU5756098A (fr) |
| BR (1) | BR9714327A (fr) |
| CA (1) | CA2278351A1 (fr) |
| DE (1) | DE19703091A1 (fr) |
| WO (1) | WO1998032807A1 (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10349811A1 (de) * | 2003-10-24 | 2005-05-25 | Bayer Materialscience Ag | Beschichtungen für Nahrungsmittelbehälter |
| DE102004060798A1 (de) * | 2004-12-17 | 2006-06-29 | Bayer Materialscience Ag | Wässrige Beschichtungen für Nahrungsmittelbehälter |
| RU2011146073A (ru) | 2009-04-13 | 2013-05-20 | У.Р. Грейс Энд Ко.-Конн. | Покрытие для металлических пищевых контейнеров, стойкое к процессам при высоких рн |
| CN109423129B (zh) * | 2017-06-21 | 2020-08-28 | 广东华润涂料有限公司 | 适用于在三片罐上形成侧缝条或侧缝涂层的水性涂料组合物 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2507884B2 (de) * | 1975-02-24 | 1981-02-05 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung wäßriger Dispersionen von pigmentierten Überzugsmitteln |
| CA1186846A (fr) * | 1978-06-12 | 1985-05-07 | George L. Brown | Substance de revetement formant une emulsion aqueuse et constituee de melanges auto-emulsifiants d'esters d'epoxyde et d'un copolymere |
| US4395444A (en) * | 1981-09-25 | 1983-07-26 | Ppg Industries, Inc. | Thermosetting cationic acrylic latex compositions containing blocked isocyanates |
| US4847316A (en) * | 1987-05-06 | 1989-07-11 | Eastman Kodak Company | Aqueous dispersion blends of polyesters and polyurethane materials and printing inks therefrom |
| ATE160454T1 (de) * | 1988-07-04 | 1997-12-15 | Sun Microsystems Inc | Multiprozessorsystem mit hierarchischer cachespeicheranordnung |
| DE3829587A1 (de) * | 1988-09-01 | 1990-03-15 | Bayer Ag | Beschichtungsmittel, ein verfahren zu ihrer herstellung und die verwendung von ausgewaehlten zweikomponenten-polyurethansystemen als bindemittel fuer derartige beschichtungsmittel |
| JPH0372577A (ja) * | 1989-04-28 | 1991-03-27 | Toyo Ink Mfg Co Ltd | 水性塗料組成物 |
| US5314945A (en) * | 1990-12-03 | 1994-05-24 | E. I. Du Pont De Nemours And Company | Waterbased coating compositions of methylol(meth)acrylamide acrylic polymer, polyurethane and melamine crosslinking agent |
| DE4223183C1 (en) * | 1992-07-15 | 1993-07-15 | Herberts Gmbh, 5600 Wuppertal, De | Emulsifier-free thermo-curable coating as aq. emulsion - comprises self-emulsifying ester-based copolymers, polyester oligomers, water-(in)soluble amine resin crosslinking agents and capped poly:isocyanate(s) |
| JPH0641491A (ja) * | 1992-07-23 | 1994-02-15 | Kansai Paint Co Ltd | 水性塗料とその塗装方法 |
| DE4332015A1 (de) * | 1993-09-21 | 1995-03-23 | Basf Lacke & Farben | Verfahren zur Herstellung von Decklackschichten |
| DE4421823A1 (de) * | 1994-06-22 | 1996-01-04 | Basf Lacke & Farben | Aus mindestens 3 Komponenten bestehendes Beschichtungsmittel, Verfahren zu seiner Herstellung sowie seine Verwendung |
| JPH08209066A (ja) * | 1995-02-07 | 1996-08-13 | Kansai Paint Co Ltd | 水性中塗塗料 |
-
1997
- 1997-01-29 DE DE19703091A patent/DE19703091A1/de not_active Ceased
- 1997-12-10 BR BR9714327-8A patent/BR9714327A/pt not_active Application Discontinuation
- 1997-12-10 AU AU57560/98A patent/AU5756098A/en not_active Abandoned
- 1997-12-10 CA CA002278351A patent/CA2278351A1/fr not_active Abandoned
- 1997-12-10 EP EP97953778A patent/EP0956321A1/fr not_active Withdrawn
- 1997-12-10 WO PCT/EP1997/006906 patent/WO1998032807A1/fr not_active Ceased
- 1997-12-10 KR KR1019997006854A patent/KR20000070606A/ko not_active Withdrawn
Non-Patent Citations (1)
| Title |
|---|
| See references of WO9832807A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20000070606A (ko) | 2000-11-25 |
| WO1998032807A1 (fr) | 1998-07-30 |
| CA2278351A1 (fr) | 1998-07-30 |
| AU5756098A (en) | 1998-08-18 |
| BR9714327A (pt) | 2000-02-08 |
| DE19703091A1 (de) | 1998-07-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5852120A (en) | Aqueous, heat curable coating compound, its preparation and its use | |
| EP1285035B1 (fr) | Composition liante aqueuse et reticulable et composition de revetement, de laquage ou d'etancheification comprenant ladite composition liante | |
| US6277910B1 (en) | Water-borne hybrid binder composition and use thereof | |
| JPH06248229A (ja) | コーティング媒体及び耐酸性コーティングの製造のためのその使用 | |
| CA2190286A1 (fr) | Agent de revetement a au moins trois composants, son procede de fabrication et son utilisation | |
| US6306956B1 (en) | Aqueous dispersion of high molecular weight polyester for chip resistant primer | |
| US5686532A (en) | Binder composition, coating composition containing this binder, production and use thereof | |
| ZA200208425B (en) | Branched hydroxyl-functional polyester resin and its use in aqueous cross-linkable binder compositions. | |
| KR100648556B1 (ko) | 고체 함량이 높은 가열건조형 에나멜용 수성 도료 및 그의용도 | |
| US5969054A (en) | High solids polyurethane binder compositions containing grafted polyacrylate polyols | |
| EP0353797A1 (fr) | Polyuréthane fonctionnalisé utilisable pour la préparation de dispersions aqueuses de polymères hybrides | |
| JPH11513721A (ja) | 少なくとも三成分からなる被覆剤、該被覆剤の製造ならびに該被覆剤の使用 | |
| JP3883628B2 (ja) | Oh官能性ポリアクリレートグラフトコポリマーを含む高固形分バインダー組成物 | |
| US6166111A (en) | Aqueous binder compositions and their use in heat curable coating compositions | |
| CN100393827C (zh) | 用于罐头涂层的含水组合物 | |
| CA2050914C (fr) | Composition de revetement, procede de fabrication et utilisation, notamment pour le peinturage de contenants aboutis | |
| US6863863B2 (en) | Coating composition, a process for its preparation, and its use in the production of textured coated surfaces | |
| EP0956321A1 (fr) | Composition de rev tement pour des recipients alimentaires | |
| US5322863A (en) | Coating compound, process for its production as well as use thereof | |
| JPS61141718A (ja) | 低分子量アクリルポリマー | |
| AT411762B (de) | Hydroxylgruppen-haltige polymere, deren herstellung und verwendung | |
| JP4208257B2 (ja) | 水散逸性ポリマー及び水性の系におけるこれらの使用法 | |
| EP0106350B1 (fr) | Compositions de revêtement à haute teneur en matières solides contenant du polycaprolactonepolyol comme diluants réactifs et un procédé pour en former un enduit | |
| US6043301A (en) | Aqueous coating compositions | |
| JP2667896B2 (ja) | ポリエステルおよび塗料用樹脂組成物 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 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 |
|
| 17P | Request for examination filed |
Effective date: 19990731 |
|
| AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AT BE CH DE ES FR GB IE IT LI NL PT SE |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
| 18D | Application deemed to be withdrawn |
Effective date: 20010703 |