NZ617726B2 - Coating compositions comprising 2,2'-biphenol - Google Patents
Coating compositions comprising 2,2'-biphenol Download PDFInfo
- Publication number
- NZ617726B2 NZ617726B2 NZ617726A NZ61772612A NZ617726B2 NZ 617726 B2 NZ617726 B2 NZ 617726B2 NZ 617726 A NZ617726 A NZ 617726A NZ 61772612 A NZ61772612 A NZ 61772612A NZ 617726 B2 NZ617726 B2 NZ 617726B2
- Authority
- NZ
- New Zealand
- Prior art keywords
- coating
- biphenol
- bisphenol
- derivatives
- residues
- Prior art date
Links
- 239000008199 coating composition Substances 0.000 title claims abstract description 32
- IMHDGJOMLMDPJN-UHFFFAOYSA-N biphenyl-2,2'-diol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1O IMHDGJOMLMDPJN-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 239000011248 coating agent Substances 0.000 claims abstract description 39
- 238000000576 coating method Methods 0.000 claims abstract description 39
- 239000000758 substrate Substances 0.000 claims abstract description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 26
- 229910052751 metal Inorganic materials 0.000 claims abstract description 26
- 239000002184 metal Substances 0.000 claims abstract description 26
- 235000013305 food Nutrition 0.000 claims abstract description 24
- 238000004806 packaging method and process Methods 0.000 claims abstract description 18
- 235000013361 beverage Nutrition 0.000 claims abstract description 17
- 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 claims abstract description 10
- PXKLMJQFEQBVLD-UHFFFAOYSA-N Bis(4-hydroxyphenyl)methane Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229920005862 polyol Polymers 0.000 claims description 15
- 150000003077 polyols Chemical class 0.000 claims description 15
- 229920000642 polymer Polymers 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 239000011574 phosphorus Substances 0.000 claims description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 4
- 229920000058 polyacrylate Polymers 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims 1
- -1 for example Substances 0.000 description 21
- 239000000203 mixture Substances 0.000 description 19
- 239000003795 chemical substances by application Substances 0.000 description 16
- 239000003960 organic solvent Substances 0.000 description 15
- 229920005989 resin Polymers 0.000 description 15
- 239000011347 resin Substances 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- 239000004593 Epoxy Substances 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
- 125000003700 epoxy group Chemical group 0.000 description 7
- 239000004970 Chain extender Substances 0.000 description 6
- 229920001228 Polyisocyanate Polymers 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 239000005056 polyisocyanate Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 238000005260 corrosion Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 229920001568 phenolic resin Polymers 0.000 description 5
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-Butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 4
- JDSHMPZPIAZGSV-UHFFFAOYSA-N Melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000010959 steel Substances 0.000 description 4
- 229920001187 thermosetting polymer Polymers 0.000 description 4
- 101700033790 CYMEL Proteins 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001253 acrylic acids Chemical class 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminum Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000004070 electrodeposition Methods 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000005011 phenolic resin Substances 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 239000011528 polyamide (building material) Substances 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000002023 wood Substances 0.000 description 3
- XUCHXOAWJMEFLF-UHFFFAOYSA-N 2-[[4-[[4-(oxiran-2-ylmethoxy)phenyl]methyl]phenoxy]methyl]oxirane Chemical compound C1OC1COC(C=C1)=CC=C1CC(C=C1)=CC=C1OCC1CO1 XUCHXOAWJMEFLF-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N Adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 229920001342 Bakelite® Polymers 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N Catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N Diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- 229920000126 Latex Polymers 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene (PE) Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N Resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N Sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000004637 bakelite Substances 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N benzohydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N 1,2-ethanediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N 1,4-Butanediol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N 1,5-Pentanediol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- LHENQXAPVKABON-UHFFFAOYSA-N 1-methoxypropan-1-ol Chemical compound CCC(O)OC LHENQXAPVKABON-UHFFFAOYSA-N 0.000 description 1
- ZAXXZBQODQDCOW-UHFFFAOYSA-N 1-methoxypropyl acetate Chemical compound CCC(OC)OC(C)=O ZAXXZBQODQDCOW-UHFFFAOYSA-N 0.000 description 1
- OWBTYPJTUOEWEK-UHFFFAOYSA-N 2,3-Butanediol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-Dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 1
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 1
- WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 description 1
- ODGCZQFTJDEYNI-UHFFFAOYSA-N 2-methylcyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1(C)C=CCCC1C(O)=O ODGCZQFTJDEYNI-UHFFFAOYSA-N 0.000 description 1
- ZRYCRPNCXLQHPN-UHFFFAOYSA-N 3-hydroxy-2-methylbenzaldehyde Chemical compound CC1=C(O)C=CC=C1C=O ZRYCRPNCXLQHPN-UHFFFAOYSA-N 0.000 description 1
- YWVFNWVZBAWOOY-UHFFFAOYSA-N 4-methylcyclohexane-1,2-dicarboxylic acid Chemical compound CC1CCC(C(O)=O)C(C(O)=O)C1 YWVFNWVZBAWOOY-UHFFFAOYSA-N 0.000 description 1
- 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 1
- BDJRBEYXGGNYIS-UHFFFAOYSA-N Azelaic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 1
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 1
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N Caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N Cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- UNXHWFMMPAWVPI-QWWZWVQMSA-N D-Threitol Natural products OC[C@@H](O)[C@H](O)CO UNXHWFMMPAWVPI-QWWZWVQMSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 210000003298 Dental Enamel Anatomy 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N Diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N Diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- TVIDDXQYHWJXFK-UHFFFAOYSA-N Dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N Erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 239000004386 Erythritol Substances 0.000 description 1
- 229940009714 Erythritol Drugs 0.000 description 1
- 229920000219 Ethylene vinyl alcohol Polymers 0.000 description 1
- 229910001335 Galvanized steel Inorganic materials 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N Glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- GQZXNSPRSGFJLY-UHFFFAOYSA-N Hypophosphorous acid Chemical compound OP=O GQZXNSPRSGFJLY-UHFFFAOYSA-N 0.000 description 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-N Isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N Methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 description 1
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N N-Butylamine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- SQDFHQJTAWCFIB-UHFFFAOYSA-N N-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 1
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- XNGIFLGASWRNHJ-UHFFFAOYSA-N Phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 1
- 229940034610 Toothpaste Drugs 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N Triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- VWUBNHFQIQYNCV-UHFFFAOYSA-M [N-]=C=O.[O-]C(=O)C=C Chemical compound [N-]=C=O.[O-]C(=O)C=C VWUBNHFQIQYNCV-UHFFFAOYSA-M 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 230000000111 anti-oxidant Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000003115 biocidal Effects 0.000 description 1
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- 238000009835 boiling Methods 0.000 description 1
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- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000011111 cardboard Substances 0.000 description 1
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- VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
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- 150000001896 cresols Chemical class 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- PXGZQGDTEZPERC-UHFFFAOYSA-N cyclohexane-1,4-dicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N ethanolamine Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N ethyl amine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N ethylene glycol monomethyl ether Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 239000004715 ethylene vinyl alcohol Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000011094 fiberboard Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
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- 125000000524 functional group Chemical group 0.000 description 1
- 239000008397 galvanized steel Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000004404 heteroalkyl group Chemical group 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- RTIAQOLKVLAEAU-UHFFFAOYSA-N hexan-3-yl acetate Chemical compound CCCC(CC)OC(C)=O RTIAQOLKVLAEAU-UHFFFAOYSA-N 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N hexane-1,2,6-triol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002365 multiple layer Substances 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000747 poly(lactic acid) polymer Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000004626 polylactic acid Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propanol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective Effects 0.000 description 1
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N tin hydride Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000005029 tin-free steel Substances 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- BSUNTQCMCCQSQH-UHFFFAOYSA-N triazine Chemical compound C1=CN=NN=C1.C1=CN=NN=C1 BSUNTQCMCCQSQH-UHFFFAOYSA-N 0.000 description 1
- IMTKRLUCQZWPRY-UHFFFAOYSA-N triazine-4-carbaldehyde Chemical compound O=CC1=CC=NN=N1 IMTKRLUCQZWPRY-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000002966 varnish Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
- C08G59/06—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols
- C08G59/066—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols with chain extension or advancing agents
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1405—Polycondensates modified by chemical after-treatment with inorganic compounds
- C08G59/1422—Polycondensates modified by chemical after-treatment with inorganic compounds containing phosphorus
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1488—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing phosphorus
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
- C08G59/245—Di-epoxy compounds carbocyclic aromatic
-
- 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
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
-
- 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
- C09D5/44—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications
- C09D5/4419—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications with polymers obtained otherwise than by polymerisation reactions only involving carbon-to-carbon unsaturated bonds
- C09D5/443—Polyepoxides
- C09D5/4434—Polyepoxides characterised by the nature of the epoxy binder
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
- Y10T428/1352—Polymer or resin containing [i.e., natural or synthetic]
- Y10T428/1355—Elemental metal containing [e.g., substrate, foil, film, coating, etc.]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31511—Of epoxy ether
Abstract
Disclosed herein is the use of a coating compositions comprising a polyglycidyl ether of a 2,2'-biphenol, wherein said coating is substantially free of bisphenol A and/or derivatives and/or residues thereof and bisphenol F and/or derivatives and/or residues thereof for coating food and/or beverage packaging. Also disclosed are methods of coating substrates using the coating compositions and substrates such as metal cans coated with the coating compositions. ackaging. Also disclosed are methods of coating substrates using the coating compositions and substrates such as metal cans coated with the coating compositions.
Description
COATING COMPOSITIONS COMPRISING 2,2’-BIPHENOL
FIELD OF THE INVENTION
The present invention relates to the use of coating compositions
comprising 2,2’-biphenol.
BACKGROUND OF THE INVENTION
A wide variety of coatings have been used to coat the surfaces of food
and beverage containers. For example, metal cans are sometimes coated using
coil coating or sheet coating operations; that is, a plane or coil or sheet of a
suitable substrate, for example, steel or aluminum, is roll coated or
electrodeposited with a suitable composition and cured. The coated substrate is
then formed into the can body or can end. Alternatively, the coating composition
may be applied, for example, by spraying, dipping and electrodeposition, to the
formed can and then cured. Coatings for food and beverage containers are
typically capable of high speed application to the substrate and provide the
necessary properties when cured to perform in a demanding end use. For
example, the coating should be safe for food contact and have acceptable
adhesion to the substrate.
Many of the coating compositions for food and beverage containers are
based on epoxy resins that are the polyglycidyl ethers of bisphenol A. Use of
bisphenol A and derivatives thereof, such as diglycidyl ethers of bisphenol A
(BADGE), epoxy novolak resins and polyols prepared with bisphenol A and
bisphenol F have recently come under attack. Although the balance of scientific
evidence available to date indicates that small trace amounts of BPA or BADGE
that might be released from existing coatings does not pose health risks to
humans, these compounds are nevertheless perceived by some as being harmful
to human health. Consequently, there is a strong desire to eliminate these
compounds from coatings for food and beverage containers. Accordingly,
packaging coating compositions for food and/or beverage packaging that do not
contain extractable quantities of BPA and/or derivatives thereof while providing
suitable properties are therefore desired. It is an object of the present invention
to go some way towards satisfying these desiderata, and/or to at least provide the
public with a useful choice.
[0003a] In this specification where reference has been made to patent
specifications, other external documents, or other sources of information, this is
generally for the purpose of providing a context for discussing the features of the
invention. Unless specifically stated otherwise, reference to such external
documents is not to be construed as an admission that such documents, or such
sources of information, in any jurisdiction, are prior art, or form part of the
common general knowledge in the art.
SUMMARY OF THE INVENTION
The present invention is directed to use of a coating composition
comprising a polyglycidyl ether of a 2,2'-biphenol, wherein said coating contains
less than 100 ppm of bisphenol A and/or derivatives and/or residues thereof and
bisphenol F and/or derivatives and/or residues thereof for coating food and/or
beverage packaging. The present invention is further directed to a method for
coating a substrate selected from food and/or beverage packaging comprising
applying to at least a portion of the substrate the coating composition as defined
above.
Described herein is a coating composition comprising a phosphated
polyglycidyl ether of a 2,2’-biphenol.
The present invention is further directed to a substrate selected from
food and/or beverage packaging coated at least in part with the coating
composition as defined above.
[0006a] In the description in this specification reference may be made to subject
matter which is not within the scope of the appended claims. That subject matter
should be readily identifiable by a person skilled in the art and may assist in
putting into practice the invention as defined in the appended claims.
DETAILED DESCRIPTION
The present invention is directed to the use of a coating composition
comprising a polyglycidyl ether of a 2,2’-biphenol. Suitable polyglycidyl ethers of
a 2,2'-biphenol contain two or more epoxy or oxirane groups. Typical polyglycidyl
ethers are epoxide-terminated linear epoxy resins having a 1,2-epoxy
equivalency not substantially in excess of 2, usually about 1.5 to 2; in certain
embodiments, the epoxy resins are difunctional with regard to epoxy. The
polyglycidyl ether of 2,2’-biphenol typically has a number average molecular
weight (M ) of at least 400, such as 400 to 2400 g/mole.
Examples of a 2,2'-biphenol include 2,2'-biphenol itself and substituted
2,2'-biphenol including those of the structure:
R OHHO R
R R R R
3 4 8 7
in which R , R , R , R , R , R , R and R are the same or different and are
1 2 3 4 5 6 7 8
independently hydrogen and hydrocarbyl groups. “Hydrocarbyl” and like terms
include, for example, alkyl groups, heteroalkyl groups, aryl groups, heteroaryl
groups and such groups with any substitutions (“substituted hydrocarbyl groups”).
As used herein, the term “2,2’-biphenol” refers to 2,2’-biphenol itself and
substituted 2,2’-biphenol in which at least one of R through R are anything other
than hydrogen.
Examples of suitable polyglycidyl ethers of a 2,2'-biphenol (“PGE”) can
be formed by reacting epihalohydrins with a 2,2'-biphenol in the presence of an
alkali condensation and dehydrohalogenation catalyst such as sodium hydroxide
or potassium hydroxide. Useful epihalohydrins include epibromohydrin,
dichlorohydrin and especially epichlorohydrin.
In certain embodiments, the polyglycidyl ether of a 2,2'-biphenol is
prepared as described above, followed by chain extension or advancement to a
higher molecular weight product that may or may not have epoxy termination.
Examples of chain extenders include monoalcohols and polyols, including
polymeric polyols, and polycarboxylic acids/anhydrides. Certain embodiments,
however, specifically exclude reaction of the PGE with a carboxylic acid and/or
anhydride-containing compound. Specific examples of chain extenders include
2,2'-biphenol and/or polyfunctional materials that are reactive with epoxy
functionality such as dihydric phenols, for example, resorcinol, pyrocatechol and
hydroquinone; aliphatic polyhydric alcohols, for example, ethylene glycol,
diethylene glycol, triethylene glycol, 1,2-propylene glycol, 1,4-butylene glycol, 2,3-
butylene glycol, pentamethylene glycol, polyoxyalkylene glycol; polyols such as
sorbitol, glycerol, 1,2,6-hexanetriol, erythritol and trimethylolpropane; and
mixtures thereof. Examples of other chain extenders include amines such as
ammonia and primary amines such as ethylamine and butylamine, diamines such
as hydrazine and ethylene diamine and hydroxyalkylamines such as
monoethanolamine and diethanolamine. In certain embodiments, the chain
extender is a polymeric polyol and the monomers of the polymeric polyol, such as
(meth)acrylic polymers, can contain a monomer with a group that is reactive with
the groups of the PGE. Such reactive groups include, for example, epoxy groups
such as those associated with glycidyl methacrylate that are reactive with the
hydroxyl groups associated with the PGE or an isocyanate acrylate such as
isocyanato ethyl methacrylate that is also reactive with the hydroxy groups of the
PGE. In certain embodiments, the monomers of the polymeric polyol can be
polymerized in the presence of the PGE. In other embodiments, the polymeric
polyol, when reacted with the PGE, will form an ungelled resinous reaction
product. As used herein, the term “ungelled” refers to resins that are substantially
free of crosslinking and have an intrinsic viscosity when dissolved in a suitable
solvent. Gelled resins have too high an intrinsic viscosity to be measured.
Examples of suitable polycarboxylic acids for use as chain extenders are phthalic
acid, isophthalic acid, terephthalic acid, 1,4-cyclohexane dicarboxylic acid,
succinic acid, sebacic acid, methyltetrahydrophthalic acid,
methylhexahydrophthalic acid, tetrahydrophthalic acid, dodecane dioic acid,
adipic acid, azelaic acid, naphthylene dicarboxylic acid, pyromellitic acid, dimer
fatty acids and/or trimellitic acid. Anhydrides of polycarboxylic acids where they
exist can also be used.
In certain embodiments, the PGE is phosphated. More specifically, the
PGE is reacted with a phosphorus acid. The PGE can be reacted with the
phosphorous acid before and/or after chain extension, if such extension is done.
A “phosphated polyglycidyl ether of a 2,2’-biphenol” therefore refers to any PGE
described herein that has been further reacted with a phosphorous acid. The
phosphorus acid that is reacted with the PGE can be a phosphinic acid, a
phosphonic acid and/or a phosphoric acid. The phosphoric acid can be in the
form of an aqueous solution, for example, an 85 percent by weight aqueous
solution, or can be 100 percent phosphoric acid or super phosphoric acid.
Typically, the acid is provided in amounts of at least 0.2, more typically 0.2 to 1.0
or 0.2 to 0.5 equivalents of phosphoric acid per equivalent of epoxy of the
polyepoxide. The reaction of the phosphorus acid with the PGE is typically
conducted in organic solvent. The organic solvent can be a hydroxyl functional
compound, such as a monofunctional compound. Among the hydroxyl functional
compounds that may be used are aliphatic alcohols, cycloaliphatic alcohols and
alkyl ether alcohols. Examples of hydroxyl functional compounds include
n-butanol and 2-butoxyethanol. Other suitable solvents are ketones and esters.
Examples include methyl ethyl ketone, methyl isobutyl ketone, butyl glycol
acetate and methoxypropyl acetate. Mixtures of organic solvents can also be
used. The organic solvent or mixture thereof typically has a boiling point of 65 to
250ºC. The reactants and the organic solvent are typically mixed at a
temperature of 50ºC to 95ºC and once the reactants are contacted, the reaction
mixture can be maintained at a temperature of 90ºC to 200ºC. The reaction
typically is allowed to proceed for a period of about 45 minutes to 6 hours. The
organic solvent for the reaction is typically present in amounts of about 20 to 50
percent by weight based on total weight of phosphorus acid, PGE and organic
solvent.
The PGE is typically present in the coating compositions in an amount of
0.1 to 95, such as 0.1 to 85 or 0.1 to 70 weight percent. In certain embodiments,
the present coatings will further comprise a crosslinker or curing agent. Curing
agents, if used in the composition, are reactive with hydroxyl groups associated
with the PGE.
Among the curing agents that may be used are phenols, phenolplasts or
phenol-formaldehyde resins, aminoplast or triazine-formaldehyde resins, and
polyisocyanates. The phenol-formaldehyde resins can be of the resol type.
Examples of suitable phenols are phenol itself, butyl phenol, xylenol and cresol.
Cresol-formaldehyde resins, the types typically etherified with butanol, are often
used. For the chemistry in preparation of phenolic resins, reference is made to
"The Chemistry and Application of Phenolic Resins or Phenolplasts", Vol. V, Part
I, edited by Dr. Oldring; John Wiley & Sons/Cita Technology Limited, London,
1997. Examples of commercially available phenolic resins are PHENODUR
PR285 and BR612 and those resins sold under the trademark BAKELITE , such
as BAKELITE 6581LB.
Examples of aminoplast resins are those that are formed by reacting a
triazine such as melamine or benzoguanamine with formaldehyde. These
condensates are typically etherified with methanol, ethanol, and/or butanol. For
the chemistry preparation and use of aminoplast resins, see "The Chemistry and
Applications of Amino Crosslinking Agents or Aminoplast", Vol. V, Part II, page 21
ff., edited by Dr. Oldring; John Wiley & Sons/Cita Technology Limited, London,
1998. These resins are commercially available under the trademark MAPRENAL
such as MAPRENAL MF980 and under the trademark CYMEL such as CYMEL
303 and CYMEL 1128, available from Cytec Industries.
Examples of polyisocyanate curing agents are blocked polyisocyanates.
A number of blocked polyisocyanates are satisfactory curing agents. These
agents are well known in the art. Generally, the organic polyisocyanates are
blocked with a volatile alcohol, epsilon caprolactam or ketoxime. These blocked
polyisocyanates become unblocked at elevated temperatures, e.g., above about
100ºC. "The Chemistry of Organic Film Formers", Robert E. Kreiger Pub. Co.,
copyrighted 1977, by D. H. Solomon, pages 216 to 217, contains a description of
many blocked isocyanates that can be used here.
The curing agent can be used in amounts of 0 to 90, such as 10 to 50 or
to 40 weight percent, with weight percent based on the total weight of the PGE
and curing agent.
In certain embodiments, the coating composition contains a diluent to
dissolve or disperse the ingredients in the composition. The diluent can be
entirely an organic solvent (organic solvent based coating composition) or mixture
of water and compatible organic solvents such as alcohols, ketones and glycol
ethers (aqueous based coating composition).
The organic solvent can be selected to have sufficient volatility to
evaporate from the coating composition during the curing process, such as during
heating from 175-205ºC for about 5 to 15 minutes. Examples of suitable organic
solvents are aliphatic hydrocarbons such as mineral spirits and high flash point
VM&P naphtha; aromatic hydrocarbons such as benzene, toluene, xylene and
solvent naphtha 100, 150, 200 and the like; alcohols, for example, ethanol, n-
propanol, isopropanol, n-butanol and the like; ketones such as acetone,
cyclohexanone, methylisobutyl ketone and the like; esters such as ethyl acetate,
butyl acetate, and the like; glycols such as butyl glycol, glycol ethers such as
methoxypropanol and ethylene glycol monomethyl ether and ethylene glycol
monobutyl ether and the like. Mixtures of various organic solvents can also be
used. The diluent can be used in the coating compositions in amounts of up to
80, such as 20 to 80, such as 30 to 70 percent by weight based on total weight of
the coating composition.
It will be appreciated that in certain embodiments the PGE and curing
agent therefor, if used, can form all or part of the film-forming resin of the coating.
In certain embodiments, one or more additional film-forming resins are also used
in the coating. The additional film-forming resin can comprise, for example,
acrylic polymers, polyester polymers, polyurethane polymers, polyamide
polymers, polyether polymers, polysiloxane polymers, copolymers thereof, and
mixtures thereof. Generally, these polymers can be any polymers of these types
made by any method known to those skilled in the art. The additional film-
forming resin may be thermosetting or thermoplastic. In embodiments where the
additional film-forming resin is thermosetting, the coating composition may further
comprise a curing agent that may be selected from any of the curing agents
described above, or any other suitable curing agent(s). The curing agent may be
the same or different from the curing agent that is used to crosslink the PGE. In
certain other embodiments, a thermosetting film-forming polymer or resin having
functional groups that are reactive with themselves are used; in this manner, such
thermosetting coatings are self-crosslinking. The coating compositions may be
solvent-based liquid compositions. The coating compositions can be one
component (“1K”), that is, all the ingredients can be stored in one container, or
multi-component, that is, the ingredients are stored in two or more containers and
mixed just prior to use.
The coating compositions useful in the present invention can also
comprise any additives standard in the art of coating manufacture including
lubricants such as waxes and surfactants, catalysts, organic cosolvents,
colorants, plasticizers, abrasion-resistant particles, film strengthening particles,
flow control agents, thixotropic agents, rheology modifiers, antioxidants, biocides,
dispersing aids, adhesion promoters, clays, stabilizing agents, fillers, reactive
diluents, and other customary auxiliaries, or combinations thereof. The colorants
and abrasion-resistant particles can be, for example, those disclosed in United
States Publication Number 2010/0055467A1, paragraphs 24-34, hereby
incorporated by reference.
In one embodiment, an ungelled resinous reaction product of PGE and a
polymer polyol can be prepared by heating the PGE in organic solvent to reflux
temperature. Thereafter, a (meth)acrylic monomer component is added with a
free radical initiator such as a peroxide or azo compound. Reaction is continued
at elevated temperature to form an ungelled resinous reaction product. Typically,
the weight ratio of PGE to methacrylic monomer component in these
embodiments is from 5 to 95:95 to 5, such as 20 to 80:80 to 20.
The present coatings can be applied to any substrates known in the art,
for example, automotive substrates, industrial substrates, packaging substrates,
architectural substrates, wood flooring and furniture, apparel, electronics
including housings and circuit boards, glass and transparencies, sports
equipment including golf balls, and the like. These substrates can be, for
example, metallic or non-metallic. Metallic substrates include tin, steel, tin-plated
steel, tin free steel, black plate, chromium passivated steel, galvanized steel,
aluminum, aluminum foil. Non-metallic substrates include polymeric, plastic,
polyester, polyolefin, polyamide, cellulosic, polystyrene, polyacrylic, poly(ethylene
naphthalate), polypropylene, polyethylene, nylon, EVOH, polylactic acid, other
“green” polymeric substrates, poly(ethyleneterephthalate) (“PET”), polycarbonate,
polycarbonate acrylobutadiene styrene (“PC/ABS”), polyamide, wood, veneer,
wood composite, particle board, medium density fiberboard, cement, stone,
glass, paper, cardboard, textiles, leather both synthetic and natural, and other
nonmetallic substrates. The substrate can be one that has been already treated
in some manner, such as to impart visual and/or color effect. Accordingly, the
coatings useful in the present invention can be a clear coat, a pigmented coat,
can be used alone or in conjunction with other coatings such as a primer layer,
basecoat, topcoat and the like.
The coatings useful in the present invention are particularly suitable for
use as a packaging coating. The application of various pretreatments and
coatings to packaging is well established. Such treatments and/or coatings, for
example, can be used in the case of metal cans, wherein the treatment and/or
coating is used to retard or inhibit corrosion, provide a decorative coating, provide
ease of handling during the manufacturing process, and the like. Coatings can
be applied to the interior of such cans to prevent the contents from contacting the
metal of the container. Contact between the metal and a food or beverage, for
example, can lead to corrosion of a metal container, which can then contaminate
the food or beverage. This is particularly true when the contents of the can are
acidic in nature. The coatings applied to the interior of metal cans also help
prevent corrosion in the headspace of the cans, which is the area between the fill
line of the product and the can lid; corrosion in the headspace is particularly
problematic with food products having a high salt content. Coatings can also be
applied to the exterior of metal cans. Certain coatings useful in the present
invention are particularly applicable for use with coiled metal stock, such as the
coiled metal stock from which the ends of cans are made (“can end stock”), and
end caps and closures are made (“cap/closure stock”). Since coatings designed
for use on can end stock and cap/closure stock are typically applied prior to the
piece being cut and stamped out of the coiled metal stock, they are typically
flexible and extensible. For example, such stock is typically coated on both sides.
Thereafter, the coated metal stock is punched. For can ends, the metal is then
scored for the “pop-top” opening and the pop-top ring is then attached with a pin
that is separately fabricated. The end is then attached to the can body by an
edge rolling process. A similar procedure is done for “easy open” can ends. For
easy open can ends, a score substantially around the perimeter of the lid allows
for easy opening or removing of the lid from the can, typically by means of a pull
tab. For caps and closures, the cap/closure stock is typically coated, such as by
roll coating, and the cap or closure stamped out of the stock; it is possible,
however, to coat the cap/closure after formation. Coatings for cans subjected to
relatively stringent temperature and/or pressure requirements should also be
resistant to cracking, popping, corrosion, blushing and/or blistering.
Accordingly, the present invention is further directed to a substrate
selected from food and/or beverage packaging coated at least in part with any of
the coating compositions described above. A “package” is anything used to
contain another item. It can be made of metal or non-metal, for example, plastic
or laminate, and be in any form. In certain embodiments, the package is a
laminate tube. In certain embodiments, the package is a metal can. The term
“metal can” includes any type of metal can, container or any type of receptacle or
portion thereof used to hold something. One example of a metal can is a food
can; the term “food can(s)” is used herein to refer to cans, containers or any type
of receptacle or portion thereof used to hold any type of food and/or beverage.
The term “metal can(s)” specifically includes food cans and also specifically
includes “can ends”, which are typically stamped from can end stock and used in
conjunction with the packaging of beverages. The term “metal cans” also
specifically includes metal caps and/or closures such as bottle caps, screw top
caps and lids of any size, lug caps, and the like. The metal cans can be used to
hold other items as well, including, but not limited to, personal care products, bug
spray, spray paint, and any other compound suitable for packaging in an aerosol
can. The cans can include “two-piece cans” and “three-piece cans” as well as
drawn and ironed one-piece cans; such one-piece cans often find application with
aerosol products. Packages coated according to the present invention can also
include plastic bottles, plastic tubes, laminates and flexible packaging, such as
those made from PE, PP, PET and the like. Such packaging could hold, for
example, food, toothpaste, personal care products and the like.
The coating can be applied to the interior and/or the exterior of the
package. For example, the coating can be rollcoated onto metal used to make a
two-piece food can, a three-piece food can, can end stock and/or cap/closure
stock. In some embodiments, the coating is applied to a coil or sheet by roll
coating; the coating is then cured by heating or radiation and can ends are
stamped out and fabricated into the finished product, i.e. can ends. In other
embodiments, the coating is applied as a rim coat to the bottom of the can; such
application can be by roll coating. The rim coat functions to reduce friction for
improved handling during the continued fabrication and/or processing of the can.
In certain embodiments, the coating is applied to caps and/or closures; such
application can include, for example, a protective varnish that is applied before
and/or after formation of the cap/closure and/or a pigmented enamel post applied
to the cap, particularly those having a scored seam at the bottom of the cap.
Decorated can stock can also be partially coated externally with the coating
described herein, and the decorated, coated can stock used to form various metal
cans.
The packages of the present invention can be coated with any of the
compositions described above by any means known in the art, such as spraying,
roll coating, dipping, flow coating and the like; the coating may also be applied by
electrocoating when the substrate is conductive. Electrocoating is particularly
suitable with coatings comprising a phosphated polyglycidyl ether of a 2,2’-
biphenol. The appropriate means of application can be determined by one skilled
in the art based upon the type of package being coated and the type of function
for which the coating is being used. The coatings described above can be
applied over the substrate as a single layer or as multiple layers with multiple
heating stages between the application of each layer, if desired. After application
to the substrate, the coating composition may be cured by any appropriate
means.
The present coatings can also be used as a packaging "size" coating,
wash coat, spray coat, end coat, and the like.
The coatings can be applied in certain embodiments to a dry film
thickness of 0.10 mils to 1.0 mils, such as from 0.10 to 0.50 mils, or from 0.15 to
0.30 mils. Thicker or thinner dry film thicknesses are also within the scope of the
present invention.
Certain embodiments of the present coatings are free of acrylic and/or
free of latex. As used in this context, “free” means acrylic and/or latex are not
intentionally added, and, if present, are present in an amount of less than 5
weight percent, such as less than 2 weight percent or less than 1 weight percent,
or 0 weight percent, with weight percent based on total weight of the coating.
In certain embodiments, the compositions useful in the invention may be
substantially free, may be essentially free and/or may be completely free of
bisphenol A and derivatives and/or residues thereof, including bisphenol A
diglycidyl ether (“BADGE”). Such compositions are sometimes referred to as
“BPA non intent” because BPA, including derivatives or residues thereof, are not
intentionally added but may be present in trace amounts because of unavoidable
contamination from the environment. The compositions may also be substantially
free, may be essentially free and/or may be completely free of bisphenol F and
derivatives and/ or residues thereof, including bisphenol F diglycidyl ether
(“BFDGE”). The term "substantially free" as used in this context means the
compositions contain less than 1000 parts per million (ppm) of the recited
compound including derivatives or residues thereof; the term "essentially
completely free" means the compositions contain less than 100 ppm; the term
"completely free" means that the compositions contain less than 20 parts per
billion (ppb) of the recited compound including derivatives or residues thereof.
As used herein, unless otherwise expressly specified, all numbers such
as those expressing values, ranges, amounts or percentages may be read as if
prefaced by the word “about”, even if the term does not expressly appear. Any
numerical range recited herein is intended to include all sub-ranges subsumed
therein. Plural encompasses singular and vice versa. For example, while the
invention has been described in terms of "a" polyglycidyl ether of “a” 2,2’-biphenol,
“a” phosphorus acid monomer, “an” organic solvent, “a” chain extender and the
like, mixtures of these and other components can be used. Also, as used herein,
the term “polymer” is meant to refer to prepolymers, oligomers and both
homopolymers and copolymers; the prefix “poly” refers to two or more. When
ranges are given, any endpoints of those ranges and/or numbers within those
ranges can be combined with the scope of the present invention. “Including”,
“such as”, “for example” and like terms means “including/such as/for example but
not limited to”. As used herein, the molecular weights are determined by gel
permeation chromatography using a polystyrene standard. Unless otherwise
indicated, molecular weights are on a number average basis (M ). The terms
“acrylic” and “acrylate” are used interchangeably (unless to do so would alter the
intended meaning) and include acrylic acids, anhydrides, and derivatives thereof,
lower alkyl-substituted acrylic acids, e.g., C -C substituted acrylic acids, such as
methacrylic acid, ethacrylic acid, etc., and their C -C alkyl esters and hydroxyalkyl
esters, unless clearly indicated otherwise. The terms "(meth)acrylic" or
"(meth)acrylate" are intended to cover both the acrylic/acrylate and
methacrylic/methacrylate forms of the indicated material, e.g., a (meth)acrylate
monomer. The term "(meth)acrylic polymer" refers to polymers prepared from one
or more (meth)acrylic monomers.
The term “comprising” as used in this specification and claims means
“consisting at least in part of”. When interpreting statements in this specification
and claims which include the term “comprising”, other features besides the
features prefaced by this term in each statement can also be present. Related
terms such as “comprise” and “comprises” are to be interpreted in similar manner.
Claims (19)
1. Use of a coating composition comprising a polyglycidyl ether of a 2,2'- biphenol, wherein said coating contains less than 100 ppm of bisphenol A and/or derivatives and/or residues thereof and bisphenol F and/or derivatives and/or residues thereof for coating food and/or beverage packaging.
2. Use of claim 1 wherein said coating contains less than 20 ppm of bisphenol A and/or derivatives and/or residues thereof and bisphenol F and/or derivatives and/or residues thereof.
3. Use of claim 1 or 2 wherein said coating is completely free of bisphenol A and/or derivatives and/or residues thereof and bisphenol F and/or derivatives and/or residues thereof.
4. Use of any one of claims 1 to 3 in which the 2,2'-biphenol has the structure: R OHHO R R R R R 3 4 8 7 in which R , R , R , R , R , R , R and R may be the same or different and are 1 2 3 4 5 6 7 8 independently hydrogen and hydrocarbyl.
5. Use of claim 4 in which R , R , R , R , R , R , R and R are hydrogen. 1 2 3 4 5 6 7 8
6. Use of any one of claims 1 to 5, wherein the polyglycidyl ether of 2,2’-biphenol is further chain-extended with a polyol.
7. Use of claim 6, wherein the polyol comprises 2,2’-biphenol.
8. Use of claim 6, wherein the polyol comprises a polymeric polyol.
9. Use of claim 8 in which the polymeric polyol comprises a (meth)acrylic polymer and/or a polyester polymer.
10. Use of any one of claims 1 to 9, wherein said polyglycidyl ether of a 2,2’-biphenol is phosphated.
11. Use of any one of claims 1 to 10, wherein said 2,2-biphenol is phosphated by reaction with a phosphorus acid.
12. Use of claim 11, wherein such coating is an electrodepositable coating.
13. Use of claim 8 in which the polyglycidyl ether of 2,2’-biphenol and the polymeric polyol are reacted together to form an ungelled resinous binder.
14. A method for coating a substrate selected from food and/or beverage packaging comprising applying to at least a portion of the substrate the coating composition defined in any one of Claims 1 to 13.
15. A substrate selected from food and/or beverage packaging coated at least in part with the coating composition defined in any one of Claims 1 to 13.
16. The substrate of Claim 15, wherein the packaging comprises a metal can.
17. Use of any one of claims 1 to 13 substantially as herein described.
18. A method of claim 14 substantially as herein described.
19. A substrate of claim 15 or 16 substantially as herein described.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201161481281P | 2011-05-02 | 2011-05-02 | |
US201161481278P | 2011-05-02 | 2011-05-02 | |
US61/481,281 | 2011-05-02 | ||
US61/481,278 | 2011-05-02 | ||
PCT/US2012/035946 WO2012151184A1 (en) | 2011-05-02 | 2012-05-01 | Coating compositions comprising 2,2'-biphenol |
Publications (2)
Publication Number | Publication Date |
---|---|
NZ617726A NZ617726A (en) | 2015-02-27 |
NZ617726B2 true NZ617726B2 (en) | 2015-05-28 |
Family
ID=
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