JP6537497B2 - 食品および飲料梱包用のポリマー組成物およびコーティング - Google Patents
食品および飲料梱包用のポリマー組成物およびコーティング Download PDFInfo
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- JP6537497B2 JP6537497B2 JP2016514009A JP2016514009A JP6537497B2 JP 6537497 B2 JP6537497 B2 JP 6537497B2 JP 2016514009 A JP2016514009 A JP 2016514009A JP 2016514009 A JP2016514009 A JP 2016514009A JP 6537497 B2 JP6537497 B2 JP 6537497B2
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- 239000000203 mixture Substances 0.000 title claims description 187
- 235000013361 beverage Nutrition 0.000 title claims description 38
- 235000013305 food Nutrition 0.000 title claims description 33
- 238000004806 packaging method and process Methods 0.000 title claims description 23
- 229920000642 polymer Polymers 0.000 title description 195
- 238000000576 coating method Methods 0.000 title description 127
- 229920005989 resin Polymers 0.000 claims description 109
- 239000011347 resin Substances 0.000 claims description 109
- 239000008199 coating composition Substances 0.000 claims description 70
- 239000004971 Cross linker Substances 0.000 claims description 60
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 51
- 229910001868 water Inorganic materials 0.000 claims description 49
- 238000004132 cross linking Methods 0.000 claims description 44
- 229910052751 metal Inorganic materials 0.000 claims description 42
- 239000002184 metal Substances 0.000 claims description 42
- 239000007795 chemical reaction product Substances 0.000 claims description 41
- 239000003054 catalyst Substances 0.000 claims description 36
- 150000004292 cyclic ethers Chemical class 0.000 claims description 31
- 239000008240 homogeneous mixture Substances 0.000 claims description 26
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 19
- 229910052782 aluminium Inorganic materials 0.000 claims description 18
- 239000007788 liquid Substances 0.000 claims description 16
- XUCHXOAWJMEFLF-UHFFFAOYSA-N bisphenol F diglycidyl ether Chemical compound C1OC1COC(C=C1)=CC=C1CC(C=C1)=CC=C1OCC1CO1 XUCHXOAWJMEFLF-UHFFFAOYSA-N 0.000 claims description 15
- 239000003999 initiator Substances 0.000 claims description 14
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 13
- 150000003254 radicals Chemical class 0.000 claims description 12
- 229920000877 Melamine resin Polymers 0.000 claims description 10
- 229910000831 Steel Inorganic materials 0.000 claims description 8
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical group NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 8
- 239000010959 steel Substances 0.000 claims description 8
- YQMXOIAIYXXXEE-UHFFFAOYSA-N 1-benzylpyrrolidin-3-ol Chemical compound C1C(O)CCN1CC1=CC=CC=C1 YQMXOIAIYXXXEE-UHFFFAOYSA-N 0.000 claims description 7
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims description 6
- 239000004094 surface-active agent Substances 0.000 claims description 6
- 150000003672 ureas Chemical class 0.000 claims description 6
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 claims description 5
- KCAMLFCTSSYIFW-UHFFFAOYSA-N 2,4,6-tris(dimethylamino)phenol Chemical compound CN(C)C1=CC(N(C)C)=C(O)C(N(C)C)=C1 KCAMLFCTSSYIFW-UHFFFAOYSA-N 0.000 claims 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 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
- 150000002170 ethers Chemical class 0.000 claims description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 4
- 150000007974 melamines Chemical class 0.000 claims description 4
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 claims description 4
- 125000005497 tetraalkylphosphonium group Chemical group 0.000 claims description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 4
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 claims description 3
- 229910000838 Al alloy Inorganic materials 0.000 claims description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 3
- 239000011651 chromium Substances 0.000 claims description 3
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 claims description 3
- 229910052718 tin Inorganic materials 0.000 claims description 3
- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 claims description 2
- 229910000851 Alloy steel Inorganic materials 0.000 claims description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- 229910000599 Cr alloy Inorganic materials 0.000 claims description 2
- 229910001128 Sn alloy Inorganic materials 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 229910001297 Zn alloy Inorganic materials 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 239000000788 chromium alloy Substances 0.000 claims description 2
- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 claims description 2
- XZZXKVYTWCYOQX-UHFFFAOYSA-J octanoate;tin(4+) Chemical compound [Sn+4].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O XZZXKVYTWCYOQX-UHFFFAOYSA-J 0.000 claims description 2
- 125000005207 tetraalkylammonium group Chemical group 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 claims description 2
- GXBYFVGCMPJVJX-UHFFFAOYSA-N Epoxybutene Chemical compound C=CC1CO1 GXBYFVGCMPJVJX-UHFFFAOYSA-N 0.000 claims 2
- JEBWAOITKHXCBF-BEAPMJEYSA-N (3s,3ar,6r,6ar)-3,6-bis(oxiran-2-ylmethoxy)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan Chemical compound O([C@@H]1[C@H]2OC[C@H]([C@H]2OC1)OCC1OC1)CC1CO1 JEBWAOITKHXCBF-BEAPMJEYSA-N 0.000 claims 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 claims 1
- 125000004386 diacrylate group Chemical group 0.000 claims 1
- -1 bisphenol compound Chemical class 0.000 description 118
- 239000000463 material Substances 0.000 description 111
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 98
- 239000011248 coating agent Substances 0.000 description 95
- 239000000178 monomer Substances 0.000 description 89
- 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 84
- 150000001875 compounds Chemical class 0.000 description 78
- 239000004593 Epoxy Substances 0.000 description 53
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 52
- 239000000758 substrate Substances 0.000 description 48
- 125000000217 alkyl group Chemical group 0.000 description 43
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 41
- 229920001187 thermosetting polymer Polymers 0.000 description 39
- 239000002253 acid Substances 0.000 description 36
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 34
- 239000000126 substance Substances 0.000 description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 29
- 238000000034 method Methods 0.000 description 29
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 29
- 239000010408 film Substances 0.000 description 28
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- 238000012360 testing method Methods 0.000 description 25
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 24
- 125000001931 aliphatic group Chemical group 0.000 description 24
- 125000004432 carbon atom Chemical group C* 0.000 description 24
- 239000010410 layer Substances 0.000 description 24
- 229920000647 polyepoxide Polymers 0.000 description 24
- 229920005862 polyol Polymers 0.000 description 24
- 239000002243 precursor Substances 0.000 description 23
- 150000002148 esters Chemical class 0.000 description 22
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
- 150000008064 anhydrides Chemical class 0.000 description 21
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- 239000000796 flavoring agent Substances 0.000 description 19
- 125000000524 functional group Chemical group 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 18
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- 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 15
- 150000007513 acids Chemical class 0.000 description 15
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 12
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- RWPGFSMJFRPDDP-UHFFFAOYSA-L potassium metabisulfite Chemical compound [K+].[K+].[O-]S(=O)S([O-])(=O)=O RWPGFSMJFRPDDP-UHFFFAOYSA-L 0.000 description 1
- 229940043349 potassium metabisulfite Drugs 0.000 description 1
- 235000010263 potassium metabisulphite Nutrition 0.000 description 1
- YLLIGHVCTUPGEH-UHFFFAOYSA-M potassium;ethanol;hydroxide Chemical compound [OH-].[K+].CCO YLLIGHVCTUPGEH-UHFFFAOYSA-M 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 description 1
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 235000019423 pullulan Nutrition 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000005551 pyridylene group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 238000007763 reverse roll coating Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 235000019615 sensations Nutrition 0.000 description 1
- 229910021332 silicide Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 125000004079 stearyl 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])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])[H] 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000004964 sulfoalkyl group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000003075 superhydrophobic effect Effects 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940065721 systemic for obstructive airway disease xanthines Drugs 0.000 description 1
- 235000015523 tannic acid Nutrition 0.000 description 1
- LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 description 1
- 229920002258 tannic acid Polymers 0.000 description 1
- 229940033123 tannic acid Drugs 0.000 description 1
- 230000009967 tasteless effect Effects 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- OIQNWJHRBIPDFR-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate 2-tert-butylbenzenecarboperoxoic acid Chemical compound C(C)(C)(C)C1=C(C(=O)OO)C=CC=C1.C(C1=CC=CC=C1)(=O)OOC(C)(C)C OIQNWJHRBIPDFR-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000007984 tetrahydrofuranes Chemical class 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical group [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- MJOXZELXZLIYPI-UHFFFAOYSA-N titanium(2+) Chemical group [Ti+2] MJOXZELXZLIYPI-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- WUCQRXWCJPCWTQ-UHFFFAOYSA-N trans-3-pentenal Natural products CC=CCC=O WUCQRXWCJPCWTQ-UHFFFAOYSA-N 0.000 description 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
- BJIOGJUNALELMI-UHFFFAOYSA-N trans-isoeugenol Natural products COC1=CC(C=CC)=CC=C1O BJIOGJUNALELMI-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- WOZZOSDBXABUFO-UHFFFAOYSA-N tri(butan-2-yloxy)alumane Chemical compound [Al+3].CCC(C)[O-].CCC(C)[O-].CCC(C)[O-] WOZZOSDBXABUFO-UHFFFAOYSA-N 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- ALVYUZIFSCKIFP-UHFFFAOYSA-N triethoxy(2-methylpropyl)silane Chemical compound CCO[Si](CC(C)C)(OCC)OCC ALVYUZIFSCKIFP-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- FHVAUDREWWXPRW-UHFFFAOYSA-N triethoxy(pentyl)silane Chemical compound CCCCC[Si](OCC)(OCC)OCC FHVAUDREWWXPRW-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- GIRKRMUMWJFNRI-UHFFFAOYSA-N tris(dimethylamino)silicon Chemical compound CN(C)[Si](N(C)C)N(C)C GIRKRMUMWJFNRI-UHFFFAOYSA-N 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- 210000002845 virion Anatomy 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 230000004393 visual impairment Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- 229930007850 β-damascenone Natural products 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
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
- B65D25/00—Details of other kinds or types of rigid or semi-rigid containers
- B65D25/14—Linings or internal coatings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/10—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers containing more than one epoxy radical per molecule
-
- 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
- C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
-
- 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
- C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
- C09D151/08—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- 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
- C09D5/002—Priming paints
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2312/00—Crosslinking
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Mechanical Engineering (AREA)
- Paints Or Removers (AREA)
- Wrappers (AREA)
Description
本出願は、2013年5月16日出願の米国仮特許出願第61/824,084号の優先権を主張するものであり、その開示内容は、その全体を参照により本明細書に援用される。
本開示は、ビスフェノールA(BPA)および関連の化合物を実質的に無含有の組成物およびコーティングに関する。
多くの飲料容器および食品容器のコーティングは、ビスフェノールベースのポリカーボネートまたはエポキシおよび関連のポリウレタンを採用し、ビスフェノール化合物は、ポリマーの一部として結合されるおよび/または移動性形態で存在する。ポリカーボネートの一般的な合成法は、ビスフェノール化合物(例、ビスフェノールA(BPA)またはビスフェノールF(BPF)等)を塩基性にして、ビス(フェノキシ)塩を形成し、その生成物をホスゲン(COCl2)と縮合し、ポリカーボネートを形成する。保護コーティングは、内容物が容器の金属表面と接触する状態になるのを回避し、金属の腐食、内容物の汚染および変質を防ぐために、金属および他の食品容器および飲料容器(例えば、缶)の内部に塗布される。
本開示において、食品梱包および飲料梱包用の新規の組成物およびコーティングが提供される。本開示のコーティング組成物は、エポキシ樹脂、アクリレート樹脂、および/またはシロキサン樹脂の同様の組み合わせをベースとすると思われる以前のコーティング組成物と異なり、他の樹脂の存在下で1種もしくは複数種の構成ポリマー樹脂を合成または架橋することにより調製され、その結果、少なくとも1つのポリマー網目の相互侵入網目または絡み合った組み合わせが生み出され、それにより、移動性ビスフェノール化合物を実質的に含有しない非常に安定した高分子網目が提供される。いくつかの実施形態において、高分子材料は、相互侵入ポリマー網目である。ある実施形態において、均質混合物中の少なくとも1種の樹脂架橋体の反応生成物は、他の樹脂から形成されるポリマーへのいかなる架橋も含まない。他の実施形態において、少なくとも1種の樹脂の反応生成物における少なくともいくつかの架橋は、他の2種の樹脂の一方もしくは両方からのある型のポリマーに結合する。それにかかわらず、網目の絡み合った組み合わせにより付与される安定性は、結果として移動性ビスフェノール化合物を実質的に含有しないコーティングをもたらす。
a)高分子材料は、環状エーテル樹脂、アクリレート樹脂およびシロキサン樹脂の3種類のうちの少なくとも2種類から選択される熱硬化性樹脂の均質混合物の反応生成物からなり、
b)熱硬化性樹脂の種類のうちの少なくとも2種類の反応生成物は、それぞれ、1種類につき乾燥重量で高分子材料の少なくとも20%を組成し、
c)高分子材料中の骨格結合のうち5%〜25%は、網目形成結合であることが可能であり、
d)高分子材料は、乾燥重量でコーティングの少なくとも90%を組成することが可能であり、
e)コーティングは、BPA、BPF、BADGEおよびBFDGEを実質的に無含有であり、そして
f)コーティングは、水との接触角が少なくとも70度であり、
コーティングの基板への密着性は、食品梱包および飲料梱包の通常の使用条件下で、化学的にほぼ安定である。
a)高分子材料は、環状エーテル樹脂、アクリレート樹脂およびシロキサン樹脂の3種類のうちの少なくとも2種類から選択される熱硬化性樹脂の均質混合物の反応生成物からなり、
b)熱硬化性樹脂の種類のうちの少なくとも2種類の反応生成物は、それぞれ、1種類につき乾燥重量で高分子材料の少なくとも20%を組成し、
c)高分子材料中の骨格結合のうち5%〜25%は、網目形成結合であることが可能であり、
d)高分子材料は、乾燥重量でコーティングの少なくとも90%を組成することが可能であり、
e)コーティングは、BPA、BPF、BADGEおよびBFDGEを実質的に無含有であり、そして
f)コーティングは、水との接触角が少なくとも70度であり、
コーティングの基板への密着性は、食品梱包および飲料梱包の通常の物理的応力下で、機械的にほぼ安定である。
a)高分子材料は、環状エーテル樹脂、アクリレート樹脂およびシロキサン樹脂の3種類のうちの少なくとも2種類から選択される熱硬化性樹脂の均質混合物の反応生成物からなり、
b)熱硬化性樹脂の種類のうちの少なくとも2種類の反応生成物は、それぞれ、1種類につき乾燥重量で高分子材料の少なくとも20%を組成し、
c)高分子材料中の骨格結合のうち5%〜25%は、網目形成結合であることが可能であり、
d)高分子材料は、乾燥重量でコーティングの少なくとも90%を組成することが可能であり、
e)コーティングは、BPA、BPF、BADGEおよびBFDGEを実質的に無含有であり、そして
f)コーティングは、水との接触角が少なくとも70度であり、
コーティングの基板への密着性は、食品梱包および飲料梱包の通常の条件および物理的応力下で、化学的にそして機械的にほぼ安定である。
本開示は、以下の:エーテル(例、環状エーテル等)、アクリルおよびシロキサンのうちの2または3種の組み合わせをベースとする硬化性の梱包用組成物を提供する。その組成物は、ビスフェノールAや関連の化合物を、たとえ含有するとしてもほんの僅かしか含有しない。本開示はまた、組成物の塗布方法および使用方法を提供する。具体的には、その方法は、食品容器および飲料容器の金属表面上の積層および内張りに有用であるが、本開示の範囲は、それに限定するものではない。本明細書に開示される組み合わせから作製されるポリマーは、著しいTg、架橋密度および疎水性を有する。さらに、そのポリマーは、十分な密着性、靭性、可撓性および耐腐食性を提供できる。硬化性組成物は、複数の重合法(ラジカル重合、縮重合、および/またはカチオン重合またはアニオン重合)を同時に行うことが可能である。さらに、その硬化性組成物は、架橋剤としてイソシアネート、ホルムアルデヒドおよびスチレンを使用することを回避する一方、他のアプローチに対してコスト競争力がある。そして硬化性組成物は、それらが接触するようになる製品において感覚刺激剤と最小の相互作用を有する。
本開示の様々な態様は、本明細書に用いる用語に関する以下の定義を参照することにより、さらに明確に理解され得る。
当業者には既知のように、「香味のスカルピング」は、梱包材料によってその香気香味が吸収されるか、または梱包された完成品に含有される成分が望ましくない香味を梱包材料から吸収するかのどちらかが起因して、梱包された完成品の品質が損失することを記載する。いくつかの筋書において、化学物質が、梱包材料から梱包材料に包まれる食料品に浸出し、それにより、味覚および/または臭気がなくなる。同様に、食品の香気が、梱包材料に吸収されることがあり、梱包材料に包まれる食料品を所望の臭いおよび/または味覚よりも劣る状態にする。本質的には、食料品と梱包材料間で化学反応が起きて、新たな香気および/または臭気を形成することもある。本開示の組成物およびコーティングは、香味の損失またはスカルピングを抑え、かつ梱包材料から梱包材料に包まれた食料品に化学物質が浸出するのを抑えるまたは最小限に抑える。
いくつかの実施形態において、組成物は、ポリマー前駆体、つまりオリゴマーである分子、またはそうでなければ小分子よりも大きい分子を含み、例えば熱源またはエネルギー源(例、電子線、紫外線、可視光線等)に暴露されることにより、または、水分、化学触媒、もしくは他の薬剤の作用により、硬化性となる1つもしくは複数の官能基を含有する。組成物は、例えば、モノマーのみまたはポリマーのみが存在するならば、上述の前駆体を全く含有せず、或いは任意選択的に、3種類のうちの任意からのポリマー前駆体、または3種類のうちの任意の組み合わせからのポリマー前駆体を含有してもよい。さらに、ある種類からのポリマー前駆体は、別の種類からのモノマー、ポリマーまたは前駆体とハイブリッド形成または結合し得る。非限定の例証的なエポキシ樹脂の前駆体として、アミノポリマーもしくはアミノプラストポリマーを形成する反応性化合物(例、アルキル化尿素−ホルムアルデヒドポリマー、メラミン−ホルムアルデヒドポリマー、アルキル化ベンゾグアナミン−ホルムアルデヒドポリマー、グリシジルエポキシ樹脂、脂環式エポキシド、およびグリシジルアミンエポキシ樹脂等)(これらに限定されない)が挙げられる。例証的なアクリレート樹脂前駆体として、アクリレートポリマーおよびアルカクリレート(alkacrylate)ポリマー、アルキルアクリレート、アクリル化エポキシ、アクリル化ウレタン、アクリル化ポリエステル、アクリル化ポリエーテル、ビニルエーテル、アクリル化オイル、およびアクリル化シリコーンをベースとするアクリレート樹脂前駆体(これらに限定されない)が挙げられる。例証的なポリシロキサン前駆体として、アルキルアルコキシシランオリゴマー;および反応性ビニルポリシロキサン(これらに限定されない)が挙げられる。いくつかの実施形態において、3種類以外であるポリマー前駆体が、架橋、可塑化、バリア性向上、または別の利点の目的のために提供される。例証的なこのような「種類以外」のポリマーの前駆体として、アルキドポリマー(例、ウレタンアルキドポリマー;ポリエステルポリマー;反応性ウレタンポリマー;フェノールポリマー;フェノール/ラテックスポリマー;等)の前駆体(これらに限定されない)が挙げられる。組成物には、モノマー、オリゴマー、ポリマー、またはそれらの組み合わせが含まれてよい。特定の実施形態において、組成物には、硬化の際に架橋を形成し得る少なくとも2種の型のポリマーのモノマーが含まれる。例えば、その組成物は、硬化の際に、エポキシ/アクリルポリマーを形成するエポキシ成分とアクリル成分を含んでもよい。
非エポキシド系環状エーテルの開環 組成物は、非エポキシド系重合性の酸素含有環を有する1種もしくは複数種の成分を含んでよい。例証的な例として、オキセタン化合物、オキソラン(例えば、テトラヒドロフラン)化合物、ジオキソラン化合物、オキセパン化合物およびジオキセパン化合物(これらに限定されない)が挙げられ、それらの化合物において、アルキレンオキシド環は、任意選択的に低級アルキル置換基を有してもよい。
アクリレート:いくつかの実施形態において、エチレン性不飽和ヒドロキシル−官能性モノマーとして、反応性の炭素−炭素二重結合およびヒドロキシル基を有するモノマー(これに限定されない)が挙げられる。適切なアルキル(メタ)アクリレートエステルの例として、メチル、エチル、プロピル、イソプロピル、ブチル、イソブチル、ペンチル、イソアミル、ヘキシル、2−エチルヘキシル、オクチル、ノニル、デシル、イソデシル、ラウリル、およびイソボルニル(メタ)アクリレート(これらに限定されない)が挙げられる。芳香族(メタ)アクリレートエステルコモノマー(例えば、シクロヘキシルおよびベンジル(メタ)アクリレート)も同様に使用され得る。ある実施形態において、(メタ)アクリルエステルは、メタクリル酸のメチルエステルおよびエチルエステルまたはこのようなエステルの混合物である。
ポリシロキサンの反応性種 組成物は、メチル−シラン、直鎖アルキルシラン、分岐のアルキルシラン、芳香族シラン、フッ素化アルキルシラン、およびジアルキルシラン(これらに限定されない)を含むシロキサン類を含んでもよい。オルガノシランの特に例証的な例として、エチルトリメトキシシラン、プロピルトリメトキシシラン、n−ブチルトリメトキシシラン、n−ブチルトリエトキシシラン、ペンチルトリエトキシシラン、フェニルトリエトキシシラン、イソブチルトリエトキシシラン、シクロペンチルトリメトキシシラン、ノナフルオロヘキシルトリス(ジメチルアミノ)シラン、およびそれらの組み合わせ(これらに限定されない)が挙げられる。
架橋を促進するために、いくつかの実施形態において、均質混合物は、シロキサン型、アクリル型および環状アルキレンオキシド型から選択される2個以上の官能基の組み合わせを有するモノマーを含む。
本開示に基づくコーティング組成物は、不揮発性固形分基準(つまり、任意選択の溶媒またはキャリア液を除いて)でコーティング組成物の約0.1重量%〜約10重量%、約1重量%〜約5重量%、または約2重量%〜約4重量%の量において、架橋剤を同様に含有してもよい。いくつかの実施形態において、架橋剤は、ヒドロキシル官能性ポリエステル樹脂、フェノール−ホルムアルデヒド樹脂、カルボキシル官能性ポリエステル樹脂およびおよび/または任意選択のクレゾール−ホルムアルデヒド樹脂の1種もしくは複数種と化学反応することができる2個以上の官能基を含む。
ポリマーは、環状エーテル以外の、アクリルまたはシロキサン官能基を有する組成物に含まれてよく、ポリマーとして最初に存在してよく、または均質混合物の硬化中に生成されてもよい。これらは、架橋剤(例えば、ポリアミンをエポキシ樹脂と共に)として、可塑剤(例えば、ポリアルキレンオキシド)として、および透明性の高い薬剤(例えば、ポリエステル)として特に有用であることがある。いくつかの実施形態において、ポリマーは、各末端において官能基で末端処理されている。当業者は、典型的なポリエステル末端基(例えば、ヒドロキシルまたはカルボキシル基)が、当技術分野で既知の従来の化学合成方法を用いて、化学的に反応してまたは交換されて、末端アミノ官能性、アミド官能性または尿素−ポリエステルポリマーを生成することを理解する。
任意選択的に、触媒を用いて、組成物での硬化速度または架橋速度を増大させてもよい。いくつかの実施形態において、触媒は、非揮発性材料の約0.05〜約5パーセントまたは約0.1〜約1.5重量パーセントの量で存在する。
溶媒 いくつかの実施形態において、組成物は、キャリア液を含む。特定の実施形態において、キャリア液は、留去および硬化を早めるために、揮発性で実質的に非水の有機溶媒または溶媒ブレンドである。硬化の前か後かのどちらかに、比較的低量の水が、最終上塗り被覆の防食特性を損なうことなく、コーティング組成物の総重量の約5パーセントまで含まれてもよい。水を組成物に意図して添加することは可能であり、またはコーティング配合中に成分を加える際等に、意図しないで導入してもよい。
食品容器および飲料容器を製作するための保護コーティングは、金属基板に塗布されて、例えば高速被覆ライン(例えば、コイルコーティングライン)上でフィルムに硬化され得る。コーティング剤は、連続的にコイルライン上または回分式でシートコーティングライン上のどちらかでローラーコーティングプロセスにおいて、薄い金属(例、アルミニウム、ブリキ、ティンフリースチール、またはクロム鋼等)に塗布された後、高温で反応する。このように生産される被覆金属は、例えば、延伸および扱き加工、絞り−再絞り、深絞り、プレス加工、水切り、金型成形(die reducing)、およびフランジング等のプロセスにより、所望の金属梱包物品を形成するように成形されてよい。
最も一般的な測定として、水との接触角は、平坦で非常に清浄な上向き面を有する水平面として注目の材料を提供し、高度に浄化した水の液滴を表面に導入した後、液滴を静止するまで放置して、最終的には、液滴のすぐ真下にある表面領域と、表面から生じる液体/気体の界面との間の角度を測定することにより、測定される。つまりその角度は液体を通る。所与の温度および圧力での、固体、液状、および気体の所与の系は、固有な平衡接触角を有する。平衡接触角は、液状、固体および気体間の相互作用の相対的な重要性を示す。しかしながら、実験測定では、いわゆる前進(最大)接触角およびいわゆる後退(最小)接触角に起因する接触角ヒステリシスを被る。平衡接触は、これらの値の中間であり、それらから算出できる。
樹脂組成物 モノマー、反応性オリゴマー、ポリマー前駆体または反応性ポリマーに対して、本開示に基づく硬化の役割を担う架橋剤および触媒は、樹脂中の、高分子材料の反応生成物の組成(重量パーセント)を決定する目的上、対応する樹脂の一部であるとみなされる。
以下の実施例は、本開示の実施形態を例証することを意図とし、決して、本開示を限定すると解釈されるべきではない。
下の表において、樹脂は、熱硬化性樹脂であり、E=環状エーテル樹脂、A=アクリレート樹脂、かつS=シロキサン樹脂である。明示のNF%は、完全な硬化混合物に関して反応生成物の骨格結合のうちの網目形成結合のおよその理論百分率を意味する。しかしながら、合成手順は、硬化された場合に達成される網目形成結合のこの理論百分率に基づいて決まるものではない。加重平均は、重量パーセントで算出したNF%値の加重平均であり、副産物(例、シロキサン縮合により生じるエタノール等)は、ポリマーの一部ではなく、従って、出発モノマーおよび架橋剤の重量百分率は、本明細書のように高分子材料のみを考慮する場合、各樹脂の反応生成物に対する重量の積と必ずしも同じではない。コーティングの目標厚さは、2〜5ミクロンである。
試料のエポキシ(1,4−シクロヘキサンジメタノールジグリシジルエーテル(CHDMGEまたはCHDMEP))9.48g、アクリルモノマー(トリプロピレングリコールジアクリレート)4.74g、別のアクリルモノマー、トリメチロールプロパントリアクリレート(TMPTA)4.74g、エアロゾルOT(ジオクチルナトリウムスルホスクシネート界面活性剤)1g、およびエタノール14gを秤量し、150mLのガラス製試料バイアル中で合わせて、手動で徐々に撹拌した。この穏やかな撹拌は、これらの材料の普遍的な混和性のお蔭で、完全な混合を実現するのに殆どの場合十分であった。試料の2,4,6−トリス(ジメチルアミノ)フェノール0.24gをこの混合物に加えた後、再び穏やかに振り混ぜて、普遍的な分散性を確保した。最終的に、0.8gのt−ブチルパーオキシベンゾエート(t−ブチルベンゾペルオキソエート、PhCO2O−t−Buとも呼ぶ)と、65gの水とを加え、最初は手動で振り混ぜた後、磁気攪拌棒を用い約250rpmで1時間撹拌した。次に、下記のように、生成した組成物からコーティングを調製した。
試料のエポキシ(1,4−シクロヘキサンジメタノールジグリシジルエーテル(CHDMGEまたはCHDMEP))9.48g、アクリルモノマー(トリプロピレングリコールジアクリレート)4.74g、別のアクリルモノマー、プロポキシル化ネオペンチルグリコールジアクリレート(プロポキシル化NPGジアクリレート)4.74g、エアロゾルOT 1g、およびエタノール14gを秤量し、150mLのガラス製試料バイアル中で合わせて、手動で徐々に撹拌した。この穏やかな撹拌は、これらの材料の普遍的な混和性のお蔭で、完全な混合を実現するのに殆どの場合十分であった。試料の2,4,6−トリス(ジメチルアミノ)フェノール0.24gをこの混合物に加えた後、再び穏やかに振り混ぜて、普遍的な分散性を確保した。最終的に、0.8gのt−ブチルパーオキシベンゾエート(t−ブチルベンゾペルオキソエート)と、65gの水とを加え、最初は手動で振り混ぜた後、磁気攪拌棒を用い約250rpmで1時間撹拌した。次に、下記のように、生成した組成物からコーティングを調製した。
試料のエポキシ(1,4−シクロヘキサンジメタノールジグリシジルエーテル(CHDMGEまたはCHDMEP))9.48g、アクリルモノマー(トリプロピレングリコールジアクリレート)4.74g、別のアクリルモノマー、トリメチロールプロパントリアクリレート(TMPTA)4.74g、エアロゾルOT 1g、ベンジルトリエトキシシラン1g、およびエタノール14gを秤量し、150mLのガラス製試料バイアル中で合わせて、手動で徐々に撹拌した。この穏やかな撹拌は、これらの材料の普遍的な混和性のお蔭で、完全な混合を実現するのに殆どの場合十分であった。試料の2,4,6−トリス(ジメチルアミノ)フェノール0.24gをこの混合物に加えた後、再び穏やかに振り混ぜて、普遍的な分散性を確保した。最終的に、0.8gのt−ブチルパーオキシベンゾエートと、65gの水とを加え、最初は手動で振り混ぜた後、磁気攪拌棒を用い約250rpmで1時間撹拌した。次に、下記のように、生成した組成物からコーティングを調製した。
1ppmのアルデヒド溶液(pH3)を以下のように調製した。
Claims (16)
- 食品および飲料梱包用のコーティング組成物であって、
a)イソソルビドジグリシジルエーテル、重量比5:1のエチレンオキシドとビニルオキシラン、重量比10:1のプロピレンオキシドとビニルオキシラン、または、1,4−シクロヘキサンジメタノールジグリシジルエーテルから選択される少なくとも1種の環状エーテルモノマー、
b)ジペンタエリトリトールペンタアクリレート、ジアクリロイルメタン、トリプロピレングリコールジアクリレート、プロポキシル化ネオペンチルグリコールジアクリレート、または、トリメチロールプロパントリアクリレートから選択される少なくとも1種のポリアクリレートモノマー、
c)フリーラジカル開始剤、
d)少なくとも1種の界面活性剤、及び、
e)キャリア液
の均質混合物から形成される高分子反応生成物を含み、
前記コーティング組成物は、BPA、BPF、BADGEおよびBFDGEを実質的に含有しない
コーティング組成物。 - 前記高分子反応生成物が硬化されている請求項1に記載のコーティング組成物。
- 前記高分子反応生成物が、乾燥重量で測定して、前記コーティング組成物の少なくとも20%を組成する請求項1に記載のコーティング組成物。
- 前記コーティング組成物が、0.1〜20ミクロン厚であり、水との接触角が少なくとも70度である請求項1に記載のコーティング組成物。
- 前記高分子反応生成物が、乾燥重量で前記コーティング組成物の少なくとも90%を組成する請求項1に記載のコーティング組成物。
- 前記混合物が0.1%〜10重量%の量で架橋剤をさらに含む請求項1に記載のコーティング組成物。
- 前記混合物がメチル化メラミンおよびブチル化メラミン、アルキル化およびイミノ混合型エーテルメラミン、アルキル化尿素、ホルムアルデヒド無含有の変性尿素、ベンゾグアナミン、グリコールウリル、又はそれらの組み合わせから選択される縮合型の架橋樹脂をさらに含む請求項1に記載のコーティング組成物。
- 前記混合物がハロゲン化テトラアルキルアンモニウム、ヨウ化テトラアルキルホスホニウムもしくはヨウ化テトラアリールホスホニウムまたは酢酸テトラアルキルホスホニウムもしくは酢酸テトラアリールホスホニウム、オクタン酸スズ、オクタン酸亜鉛、トリフェニルホスフィン又はそれらの任意の組み合わせから選択される触媒をさらに含む請求項1に記載のコーティング組成物。
- 食品容器および飲料容器であって、
a)アルミニウム、アルミニウム合金、鋼、鋼合金、スズ、スズ合金、亜鉛、亜鉛合金、クロム又はクロム合金から選択される金属と、
b)前記金属の表面を少なくとも部分的に被覆する請求項1に記載のコーティング組成物と
を含む食品容器および飲料容器。 - 前記少なくとも1種のポリアクリレートモノマーが、トリプロピレングリコールジアクリレート、プロポキシル化ネオペンチルグリコールジアクリレート、トリメチロールプロパントリアクリレート又はそれらの任意の組み合わせから選択される請求項1に記載のコーティング組成物。
- 前記少なくとも1種のポリアクリレートモノマーが、前記均質混合物の4.7〜9.4重量%である請求項1に記載のコーティング組成物。
- 前記少なくとも1種の環状エーテルモノマーが、1,4−シクロヘキサンジメタノールジグリシジルエーテルである請求項1に記載のコーティング組成物。
- 前記少なくとも1種の環状エーテルモノマーが、前記均質混合物の9.5重量%である請求項1に記載のコーティング組成物。
- 前記フリーラジカル開始剤が、t−ブチルパーオキシベンゾエートを含む請求項1に記載のコーティング組成物。
- 前記少なくとも1種の界面活性剤が、2,4,6−トリス(ジメチルアミノ)フェノール及び/又はエアロゾルOTを含む請求項1に記載のコーティング組成物。
- 前記コーティング組成物のTg値が60〜80℃である請求項2に記載のコーティング組成物。
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