NO783432L - WATERLESS RESIN FOR USE IN A COATING PREPARATION - Google Patents
WATERLESS RESIN FOR USE IN A COATING PREPARATIONInfo
- Publication number
- NO783432L NO783432L NO783432A NO783432A NO783432L NO 783432 L NO783432 L NO 783432L NO 783432 A NO783432 A NO 783432A NO 783432 A NO783432 A NO 783432A NO 783432 L NO783432 L NO 783432L
- Authority
- NO
- Norway
- Prior art keywords
- bisphenol
- diglycidyl ether
- weight
- resin
- acid
- Prior art date
Links
- 238000000576 coating method Methods 0.000 title claims description 58
- 239000011248 coating agent Substances 0.000 title claims description 49
- 238000002360 preparation method Methods 0.000 title claims description 35
- 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 description 72
- 229920005989 resin Polymers 0.000 claims description 43
- 239000011347 resin Substances 0.000 claims description 43
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 38
- 229930185605 Bisphenol Natural products 0.000 claims description 38
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 34
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 23
- 150000008064 anhydrides Chemical class 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 239000004593 Epoxy Substances 0.000 claims description 16
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 14
- 235000021355 Stearic acid Nutrition 0.000 claims description 14
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 14
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 14
- 239000008117 stearic acid Substances 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 11
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 9
- 150000001298 alcohols Chemical class 0.000 claims description 8
- 229920003180 amino resin Polymers 0.000 claims description 8
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 8
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 7
- BNCADMBVWNPPIZ-UHFFFAOYSA-N 2-n,2-n,4-n,4-n,6-n,6-n-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical group COCN(COC)C1=NC(N(COC)COC)=NC(N(COC)COC)=N1 BNCADMBVWNPPIZ-UHFFFAOYSA-N 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical group OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 claims description 6
- 239000000908 ammonium hydroxide Substances 0.000 claims description 5
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 5
- DYCRDXOGOYSIIA-UHFFFAOYSA-N 1-hexoxyethanol Chemical compound CCCCCCOC(C)O DYCRDXOGOYSIIA-UHFFFAOYSA-N 0.000 claims description 4
- 235000021314 Palmitic acid Nutrition 0.000 claims description 4
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 3
- 239000011928 denatured alcohol Substances 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000011877 solvent mixture Substances 0.000 claims 1
- 235000013405 beer Nutrition 0.000 description 13
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 13
- -1 e.g. stearic acid Chemical class 0.000 description 12
- 235000019441 ethanol Nutrition 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 238000012360 testing method Methods 0.000 description 10
- 150000002576 ketones Chemical class 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- 229930195729 fatty acid Natural products 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- 150000004665 fatty acids Chemical class 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- 150000005215 alkyl ethers Chemical class 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000003822 epoxy resin Substances 0.000 description 5
- 229920000647 polyepoxide Polymers 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 238000006253 efflorescence Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 206010037844 rash Diseases 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000008199 coating composition Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000011888 foil Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 2
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 2
- PFCHFHIRKBAQGU-UHFFFAOYSA-N 3-hexanone Chemical compound CCCC(=O)CC PFCHFHIRKBAQGU-UHFFFAOYSA-N 0.000 description 2
- IWTBVKIGCDZRPL-UHFFFAOYSA-N 3-methylpentanol Chemical compound CCC(C)CCO IWTBVKIGCDZRPL-UHFFFAOYSA-N 0.000 description 2
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- ZTJORNVITHUQJA-UHFFFAOYSA-N Heptyl p-hydroxybenzoate Chemical compound CCCCCCCOC(=O)C1=CC=C(O)C=C1 ZTJORNVITHUQJA-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 239000011260 aqueous acid Substances 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- KEMQGTRYUADPNZ-UHFFFAOYSA-N heptadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)=O KEMQGTRYUADPNZ-UHFFFAOYSA-N 0.000 description 2
- 235000019251 heptyl p-hydroxybenzoate Nutrition 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 238000009928 pasteurization Methods 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
- 238000007761 roller coating Methods 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 2
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 1
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 1
- IDQBJILTOGBZCR-UHFFFAOYSA-N 1-butoxypropan-1-ol Chemical compound CCCCOC(O)CC IDQBJILTOGBZCR-UHFFFAOYSA-N 0.000 description 1
- CUZLJOLBIRPEFB-UHFFFAOYSA-N 1-methoxypropan-2-one Chemical compound COCC(C)=O CUZLJOLBIRPEFB-UHFFFAOYSA-N 0.000 description 1
- FRKWIUGOPAAFHI-UHFFFAOYSA-N 2,4,6-triethyl-2h-1,3,5-triazine-1,5,6-triamine Chemical compound CCC1N=C(CC)N(N)C(N)(CC)N1N FRKWIUGOPAAFHI-UHFFFAOYSA-N 0.000 description 1
- AXCCTNWOXQEKQA-UHFFFAOYSA-N 2,4,6-triphenyl-2h-1,3,5-triazine-1,5,6-triamine Chemical compound NN1C(C=2C=CC=CC=2)N=C(C=2C=CC=CC=2)N(N)C1(N)C1=CC=CC=C1 AXCCTNWOXQEKQA-UHFFFAOYSA-N 0.000 description 1
- LYANEXCVXFZQFF-UHFFFAOYSA-N 2-(2,5-dioxooxolan-3-yl)acetic acid Chemical compound OC(=O)CC1CC(=O)OC1=O LYANEXCVXFZQFF-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- PFNHSEQQEPMLNI-UHFFFAOYSA-N 2-methyl-1-pentanol Chemical compound CCCC(C)CO PFNHSEQQEPMLNI-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- DFATXMYLKPCSCX-UHFFFAOYSA-N 3-methylsuccinic anhydride Chemical compound CC1CC(=O)OC1=O DFATXMYLKPCSCX-UHFFFAOYSA-N 0.000 description 1
- RHLVCLIPMVJYKS-UHFFFAOYSA-N 3-octanone Chemical compound CCCCCC(=O)CC RHLVCLIPMVJYKS-UHFFFAOYSA-N 0.000 description 1
- LDMRLRNXHLPZJN-UHFFFAOYSA-N 3-propoxypropan-1-ol Chemical compound CCCOCCCO LDMRLRNXHLPZJN-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- ZVHAANQOQZVVFD-UHFFFAOYSA-N 5-methylhexan-1-ol Chemical compound CC(C)CCCCO ZVHAANQOQZVVFD-UHFFFAOYSA-N 0.000 description 1
- FVFVNNKYKYZTJU-UHFFFAOYSA-N 6-chloro-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(Cl)=N1 FVFVNNKYKYZTJU-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 235000003255 Carthamus tinctorius Nutrition 0.000 description 1
- 244000020518 Carthamus tinctorius Species 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- NJYZCEFQAIUHSD-UHFFFAOYSA-N acetoguanamine Chemical compound CC1=NC(N)=NC(N)=N1 NJYZCEFQAIUHSD-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- MASBWURJQFFLOO-UHFFFAOYSA-N ammeline Chemical compound NC1=NC(N)=NC(O)=N1 MASBWURJQFFLOO-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical class CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- 239000003398 denaturant Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229920006334 epoxy coating Polymers 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000004426 flaxseed Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 1
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- YAQXGBBDJYBXKL-UHFFFAOYSA-N iron(2+);1,10-phenanthroline;dicyanide Chemical compound [Fe+2].N#[C-].N#[C-].C1=CN=C2C3=NC=CC=C3C=CC2=C1.C1=CN=C2C3=NC=CC=C3C=CC2=C1 YAQXGBBDJYBXKL-UHFFFAOYSA-N 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 229960004011 methenamine Drugs 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 1
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
- 150000002842 nonanoic acids Chemical class 0.000 description 1
- 125000005473 octanoic acid group Chemical class 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229960002969 oleic acid Drugs 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- SQYNKIJPMDEDEG-UHFFFAOYSA-N paraldehyde Chemical compound CC1OC(C)OC(C)O1 SQYNKIJPMDEDEG-UHFFFAOYSA-N 0.000 description 1
- 229960003868 paraldehyde Drugs 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- MCSINKKTEDDPNK-UHFFFAOYSA-N propyl propionate Chemical compound CCCOC(=O)CC MCSINKKTEDDPNK-UHFFFAOYSA-N 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 229960004274 stearic acid Drugs 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical class CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Description
Oppfinnelsen vedrører epoksy-baserte harpikser som er vannsolubiliserbare med ammoniakk eller et amin og vannbaserte belegningsprodukter som inneholder dem. The invention relates to epoxy-based resins which are water-solubilizable with ammonia or an amine and water-based coating products containing them.
Det er blitt foreslått å lage vann-fortynnbare emul-sjoner eller dispersjoner som inneholder epoksy harpikser for anvendelse som vannbaserte belegg. Slike belegg har sine ulemper, og det er sværtønskelig å tilveiebringe vannløselige epoksy-baserte belegg. Tidligere kjente epoksy-baserte belegg har dårlig holdbarhet på grunn av nærvær av oksiran-grupper og/ eller uomsatt anhydrid. It has been proposed to make water-dilutable emulsions or dispersions containing epoxy resins for use as water-based coatings. Such coatings have their disadvantages, and it is highly desirable to provide water-soluble epoxy-based coatings. Previously known epoxy-based coatings have poor durability due to the presence of oxirane groups and/or unreacted anhydride.
I US-patentskrift nr. 4 105 614 er det åpenbart enIn US Patent No. 4,105,614 there is obviously a
harpiks i hvilken epoksy-gruppene av en diglycidyleter er avdekket med en bisfenol og hvor det resulterende materiale er omsatt med et anhydrid for tilveiebringelse av vannsolubiliserbare karboksyl-grupper.. Harpiksene i henhold til foreliggende oppfinnelse som anvender en monokarboksylsyre, som f.eks. stearinsyre, har for-deler fremfor harpiksene i henhold til det nevnte patent: 1. Belegg laget av disse absorberer ikke n-heptyl-p-hydroksybenzoat et konserveringsmiddel som anvendes for stabi-lisering av ikke-pasteurisert øl. resin in which the epoxy groups of a diglycidyl ether are capped with a bisphenol and where the resulting material is reacted with an anhydride to provide water-solubilized carboxyl groups. The resins according to the present invention which use a monocarboxylic acid, such as e.g. stearic acid, has advantages over the resins according to the aforementioned patent: 1. Coatings made from these do not absorb n-heptyl-p-hydroxybenzoate, a preservative used to stabilize unpasteurized beer.
2. Belegg laget av disse har mindre innvirkning på2. Coatings made from these have less impact on
aromaen hos øl under kortvarig lagring.the aroma of beer during short-term storage.
3. Belegningspreparatene har høyere faststoffinnhold ved påføringsviskositet, noe som tillater anvendelse av et enkelt belegg for oppnåelse av de belegningsvekter som er nødvendige ved standardanvendelser. Påføringsviskositeten er generelt 154-100 sek. fortrinnsvis 25-70 sek., Zahn-cup nr. 2. 4. Det endelige belegningspreparat har bedre holdbarhet (shelf life) målt i viskositetsforandring. 3. The coating preparations have a higher solids content at application viscosity, which allows the use of a single coating to achieve the coating weights required for standard applications. The application viscosity is generally 154-100 sec. preferably 25-70 sec., Zahn cup no. 2. 4. The final coating preparation has better durability (shelf life) measured in viscosity change.
Såvidt vites er det hittil ikke blitt foreslåttAs far as is known, it has not been proposed so far
noe harpikssystem av denne type og belegg som inneholder slike. any resin system of this type and coatings containing such.
Foreliggende oppfinnelse tilveiebringer en vannsolubiliserbar harpiks som omfatter et addukt av en monokarboksylsyre og en diglycidyleter av en bisfenol eller av en monokarboksylsyre, en bisfenol og en diglycidyleter av en bisfenol, under anvendelse av et ekvivalent forhold mellom summen av monokarboksylsyre og bisfenol, om sådan anvendes, og diglycidyleter på mellom ca. 1:1 og ca. 1,2:1, videre addukt-dannet med et anhydrid i en mengde som er tilstrekkelig til å tilveiebringe et syretall på mellom ca. 35 og ca. 150. The present invention provides a water-solubilizable resin comprising an adduct of a monocarboxylic acid and a diglycidyl ether of a bisphenol or of a monocarboxylic acid, a bisphenol and a diglycidyl ether of a bisphenol, using an equivalent ratio between the sum of monocarboxylic acid and bisphenol, if used, and diglycidyl ethers of between approx. 1:1 and approx. 1.2:1, further adduct-formed with an anhydride in an amount sufficient to provide an acid number of between approx. 35 and approx. 150.
Oppfinnelsen tilveiebringer også et belegningspreparat som omfatter en slik harpiks og en aminoplast, i et vektforhold som ligger mellom ca. 95:5 og ca. 70:30 solubilisert med et flyktig tertiært amin, ammoniakk eller ammoniumhydroksyd til en pH-verdi på ca.7,0 -ca.9,1 i minst ett løsningsmiddel fra gruppen bestående av alkoholer, alkoksyetanoler, .ketoner og alkyletere av dietylenglykol, idet hvert av disse er tilstede i mellom ca. 1 vekt% og ca. 20 vekt% regnet på vekten av det ferdige preparat og fortynnet med vann til et faststoffinnhold mellom ca. 10 vekt% The invention also provides a coating preparation comprising such a resin and an aminoplast, in a weight ratio that lies between approx. 95:5 and approx. 70:30 solubilized with a volatile tertiary amine, ammonia or ammonium hydroxide to a pH value of approx. 7.0 - approx. 9.1 in at least one solvent from the group consisting of alcohols, alkoxyethanols, ketones and alkyl ethers of diethylene glycol, each of these is present in between approx. 1% by weight and approx. 20% by weight calculated on the weight of the finished preparation and diluted with water to a solids content between approx. 10% by weight
og ca. 25 vekt%.and approx. 25% by weight.
Oppfinnelsen tilveiebringer også substrater som er belagt med et slikt belegningspreparat, samt forpakningsbeholdere av metall som. er innvendig belagt med et slikt belegningspreparat og innbrent, og som inneholder et næringsmiddel eller en drikk. The invention also provides substrates which are coated with such a coating preparation, as well as packaging containers made of metal which. is internally coated with such a coating preparation and baked in, and which contains a foodstuff or a drink.
De vann-fortynnbare harpikser i henhold til oppfinnelsen fremstilles ved addukt-dannelse av tilstrekkelig monokarboksylsyre eller monokarboksylsyre og bisfenol til en diglycidyleter av en bisfenol til å reagere med alle epoksy-grupper. Diglycidyleteren oppvarmes vanligvis til ca. 80 - 90°C i et egnet løsningsmiddel som ikke bare er løsningsmiddel for reaksjonen, men som kan være en komponent av en binær azeotrop med vann. Deretter tilsettes monokarboksylsyren eller monokarboksylsyren og bisfenolen, og adduksjonen fortsettes vanligvis ved ca. 150°C i 2 - 3 timer inntil epoksy-verdien er 0,008 eller mindre. Denne adduksjons-reaksjon kan utføres i hvilkensomhelst rekkefølge, dvs. monokarboksylsyre først, fulgt av bisfenol, om sådan anvendes; eller bisfenol, om denne anvendes, først, fulgt av monokarboksylsyre. Det foretrekkes å omsette monokarboksylsyre, bisfenol og diglycidyleter av en bisfenol samtidig. The water-dilutable resins according to the invention are prepared by adducting sufficient monocarboxylic acid or monocarboxylic acid and bisphenol to a diglycidyl ether of a bisphenol to react with all epoxy groups. The diglycidyl ether is usually heated to approx. 80 - 90°C in a suitable solvent which is not only the solvent for the reaction, but which may be a component of a binary azeotrope with water. The monocarboxylic acid or the monocarboxylic acid and the bisphenol are then added, and the adduction is usually continued at approx. 150°C for 2 - 3 hours until the epoxy value is 0.008 or less. This adduction reaction can be carried out in any order, i.e. monocarboxylic acid first, followed by bisphenol, if used; or bisphenol, if this is used, first, followed by monocarboxylic acid. It is preferred to react monocarboxylic acid, bisphenol and diglycidyl ether of a bisphenol simultaneously.
Egnede løsningsmideler er ketoner, etere og estere. Suitable solvents are ketones, ethers and esters.
Ikke-begrensende eksemler på egnede løsningsmidler er metyletylketon, metylisonutylketon, diisobutyleter og n-propylacetat, n-butylacetat, isobutylacetat, n-propylpropionat og etylbutyrat. Ketoner foretrekkes særlig. Non-limiting examples of suitable solvents are methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ether and n-propyl acetate, n-butyl acetate, isobutyl acetate, n-propyl propionate and ethyl butyrate. Ketones are particularly preferred.
Reaksjonsblandingen skal tilbakeløpsbehandles for fjerning av alt vann som kan være tilstede. Vandige betingelser er nødvendig før anhydrider tilsettes. Etter at alt vann som eventuelt er tilstede, er fjernet, tilsettes et anhydrid i en mengde som- er tilstrekkelig til å tilveiebringe et syretall på mellom ca. 35 og ca. 150, fortrinnsvis 40 - 90. Generelt utføres reaksjonen ved ca. 100 - 120°C i ca.' 2 - 4 timer. Omsetningen av anhydridet er fullstendig når det alkoholiske syretall og det vandige syretall er praktisk talt like, van- The reaction mixture must be refluxed to remove any water that may be present. Aqueous conditions are required before anhydrides are added. After all water that may be present has been removed, an anhydride is added in an amount sufficient to provide an acid value of between approx. 35 and approx. 150, preferably 40 - 90. In general, the reaction is carried out at approx. 100 - 120°C for approx.' 24 hours. The conversion of the anhydride is complete when the alcoholic acid number and the aqueous acid number are practically equal, usually
ligvis innen to enheter fra hverandre. I den hensikt å sikre god holdbarhet må anhydridtallet være under ca. 6 og fortrinnsvis 0. Anhydridtallet er forskjellen mellom det alkoholiske syretall literally within two units of each other. In order to ensure good durability, the anhydride number must be below approx. 6 and preferably 0. The anhydride number is the difference between the alcoholic acid number
og det vandige syretall.and the aqueous acid number.
En alkoksyetanol som koker ved ca. 130°C eller høyereAn alkoxyethanol that boils at approx. 130°C or higher
og andre løsningsmidler, f.eks. alkoholer, tilsettes for reduksjon av faststoffinnholdet til mellom ca. 60 og ca. 75 vekt%. and other solvents, e.g. alcohols, are added to reduce the solids content to between approx. 60 and approx. 75% by weight.
Den epoksy harpiks som er anvendelig i forbindelse med oppfinnelsen, er en diglycidyleter av en bisfenol, en klasse av forbindelser som er samensatt av et par av fenoliske grupper som er forbundet via en alifatisk bro. Selvom hvilkesomhelst av bisfe-nolene kan anvendes, er forbindelsen 2,2-bis(p-hydroksyfenyl)propan som er vanlig kjent som bisfenol A, lettere tilgjengelig i handelen og foretrekkes. Diglycidyleterne av bisfenol A er lett tilgjengelige kommersielt. Epoksy harpiksen, dvs. diglycidyleteren av en bisfenol, vil ha en epoksy-ekvivalentvekt på mellom ca. 180 og ca. 2.500. The epoxy resin which is applicable in connection with the invention is a diglycidyl ether of a bisphenol, a class of compounds composed of a pair of phenolic groups connected via an aliphatic bridge. Although any of the bisphenols may be used, the compound 2,2-bis(p-hydroxyphenyl)propane commonly known as bisphenol A is more readily available commercially and is preferred. The diglycidyl ethers of bisphenol A are readily available commercially. The epoxy resin, i.e. the diglycidyl ether of a bisphenol, will have an epoxy equivalent weight of between approx. 180 and approx. 2,500.
De alifatiske monokarboksylsyrer som er anvendelige i forbindelse med oppfinnelsen, har mellom 8 og 18 karbonatomer og en molekylvekt mellom ca. 140 og ca. 290. The aliphatic monocarboxylic acids which are applicable in connection with the invention have between 8 and 18 carbon atoms and a molecular weight between approx. 140 and approx. 290.
Blandinger av monokarboksylsyrer er innen oppfinnelsens ramme. Ikke-begrensende eksempler på de alifatiske monokarboksylsyrer og blandiger av disse er oktansyrer, nonansyrer, dekansyrer, undekan-syrer, laurinsyre, tridekansyre, myristinsyre, pentadekansyre, pal mitinsyre, heptadekansyre, stearinsyre, oljesyre, linolsyre, linolensyre, ricinolsyre, linfrøfettsyre, safflorfettsyre, soyafettsyre, talloljefettsyre, bomullsfrøfettsyre, ricinusoljefettsyre, dehydratiserto ricinusoljefettsyre, og tungoljefettsyre. Mixtures of monocarboxylic acids are within the scope of the invention. Non-limiting examples of the aliphatic monocarboxylic acids and mixtures thereof are octanoic acids, nonanoic acids, decanoic acids, undecanoic acids, lauric acid, tridecanoic acid, myristic acid, pentadecanoic acid, palmitic acid, heptadecanoic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, ricinoleic acid, linseed fatty acid, safflower fatty acid, soybean fatty acid, tall oil fatty acid, cottonseed fatty acid, castor oil fatty acid, dehydrated castor oil fatty acid, and heavy oil fatty acid.
Den bisfenol som addukt-dannes med epoksy-harpiksenThe bisphenol adduct is formed with the epoxy resin
kan være hvilkeh som helst bisfenol, som angitt ovenfor. Fortrinnsvis anvendes en bisf enol...A, _ Ekvivalentforholdet mellom summen av monokarboksylsyrer og bisfenol, hvis sådan anvendes, og diglycidyleter av en bisfenol vil ligge mellom ca. 1:1 og ca. 1,2:1. Ekvivalentforholdet mellom monokarboksylsyre og diglycidyleter av en bisfenol vil ligge mellom ca. 0,1:1 og ca. 1:1. Ekvivalentforholdet mellom bisfenol og diglycidyleter av en bisfenol vil ligge mellom ca. X),'0:1 og ca. •0,9:1. Det grunnleggende formål med å anvende en bisfenol er å forstørre molekylvekten (MV) til diglycidyleteren av en bisfenol for å sikre ti-lstrekkelig molekylvekt i den endelige sure harpiks. Hvis diglycidyleteren av en bisfenol har tilstrekkelig høy molekylvekt, anvendes ikke bisfenol. Generelt vil molekylvekten til sluttharpiksen, målt ved hjelp av can be any bisphenol, as indicated above. Preferably a bisphenol...A is used, _ The equivalent ratio between the sum of monocarboxylic acids and bisphenol, if such is used, and diglycidyl ethers of a bisphenol will lie between approx. 1:1 and approx. 1.2:1. The equivalent ratio between monocarboxylic acid and diglycidyl ether of a bisphenol will lie between approx. 0.1:1 and approx. 1:1. The equivalent ratio between bisphenol and diglycidyl ether of a bisphenol will lie between approx. X),'0:1 and approx. •0.9:1. The basic purpose of using a bisphenol is to increase the molecular weight (MW) of the diglycidyl ether of a bisphenol to ensure sufficient molecular weight in the final acidic resin. If the diglycidyl ether of a bisphenol has a sufficiently high molecular weight, bisphenol is not used. In general, the molecular weight of the final resin, as measured by
gel gjennomtrengningskromatografi ligge mellom ca. 5.000 og ca. 25.000. Fortrinnsvis bør MV ligge mellom ca.8.000 og ca. 20.000. Det er mest å foretrekke at MV ligger mellom ca. 11.000 og ca. 13.000. gel permeation chromatography lie between approx. 5,000 and approx. 25,000. Preferably MV should lie between approx. 8,000 and approx. 20,000. It is most preferable that MV lies between approx. 11,000 and approx. 13,000.
Det foretrukne anhydrid som anvendes i harpiksen i henhold til oppfinnelsen er trimellittsyreanhydrid. Andre sykliske anhydrider som kan anvendes, inkluderer ravsyreanhydrid, metylravsyre-anhydrid, trikarballylsyreanhydrid, ftalsyreanhydrid, heksahydro-ftalsyreanhydrid og maleinsyréanhydrid. The preferred anhydride used in the resin according to the invention is trimellitic anhydride. Other cyclic anhydrides which may be used include succinic anhydride, methylsuccinic anhydride, tricarballylic anhydride, phthalic anhydride, hexahydrophthalic anhydride and maleic anhydride.
Mengden av anhydrid som anvendes, må være tilstrekkelig til at det oppnås et syretall på 35 - 150, fortrinnsvis mellom ca. 40 og ca. 90, for å sikre vannløselighet når harpiksen nøytrali-seres. The amount of anhydride used must be sufficient to achieve an acid number of 35 - 150, preferably between approx. 40 and approx. 90, to ensure water solubility when the resin is neutralized.
I den hensikt å oppnå god holdbarhet for belegningspreparatet må det ikke være noen uomsatte anhydridgrupper. Mengden av anhydrid som skal anvendes, kan lett beregnes ut fra hydroksyl-tallet til monokarboksylsyre-og bisfenol-epoksy-adduktet. In order to achieve good durability for the coating preparation, there must be no unreacted anhydride groups. The amount of anhydride to be used can easily be calculated from the hydroxyl number of the monocarboxylic acid and bisphenol epoxy adduct.
Ved fremstilling av et belegningspreparat som inneholder den sure harpiks, nøytraliseres harpiksen med et tertiært amin, ammoniakk eller ammoniumhydroksyd til pH ca..7,0 - ca. 9,1. Typiske aminer som er anvendelige, inkluderer trietylamin, tri-propylamin, dimetyletanolamin, dietyletanolamin, dimetyletylamin og metyldietylamin. When preparing a coating preparation containing the acidic resin, the resin is neutralized with a tertiary amine, ammonia or ammonium hydroxide to a pH of approx. 7.0 - approx. 9.1. Typical amines useful include triethylamine, tripropylamine, dimethylethanolamine, diethylethanolamine, dimethylethylamine and methyldiethylamine.
Det materiale som anvendes for å termoherde belegget,The material used to thermoset the coating,
er et konvensjonelt aminoplast-tverrbindingsmiddel. Slike midler er velkjente på fagområdet. Det kan anvendes hvilketsom- is a conventional aminoplast cross-linking agent. Such means are well known in the field. It can be used which-
helst av de termoherdende alkylerte aminoplastharpikser, f.eks. urea-aldehydharpiksene, melamin-aldehydharpiksene, dicyandiamid-.aldehydharpiksene og andre aminoplast-aldehydharpikser, f.eks. preferably of the thermosetting alkylated aminoplast resins, e.g. the urea-aldehyde resins, the melamine-aldehyde resins, the dicyandiamide-aldehyde resins and other aminoplast-aldehyde resins, e.g.
de triazine harpikser som fremstilles ved omsetning mellom et aldehyd og formoguanamin, ammelin, 2-klor,4.6-diamino-l,3,5-triazin, 2-fenyl-p-oksy-4,6-diamino-l,3,5-triazin, 6-metyl-2,4-diamino-l,3,5-triazin; 2,4,6-trihydrazin-l,3,5-triazin og 2,4,6-trietyl-triamino-1,3,5-triazin. Det foretrekkes å anvende mono-, di- eller triaralkyl-eller mono-, di- eller triarylmelaminer, f.eks. 2, 4, 6-trifenyl-triamino-1, 3,5-triazin. Som aldehyder som anvendes for omsetning med aminoforbindelsen for dannelse av harpiksmaterialet, kan man anvende slike aldehyder som formaldehyd, acetaldehyd, kortonaldehyd, acrolein- eller forbindelser som frembringer aldehyder, f.eks. heksa-metylentetramin, paraldehyd, paraformaldehyd og lignende. Den foretrukne aminoplast er heksametoksymetylmelamin. Vektforholdet mellom sur harpiks og aminoplast vil ligge mellom ca. 95:5 og ca. 70:30. the triazine resins produced by reaction between an aldehyde and formoguanamine, ammelin, 2-chloro,4,6-diamino-1,3,5-triazine, 2-phenyl-p-oxy-4,6-diamino-1,3,5 -triazine, 6-methyl-2,4-diamino-1,3,5-triazine; 2,4,6-trihydrazine-1,3,5-triazine and 2,4,6-triethyltriamino-1,3,5-triazine. It is preferred to use mono-, di- or trialkyl or mono-, di- or triaryl melamines, e.g. 2, 4, 6-triphenyl-triamino-1, 3,5-triazine. As aldehydes used for reaction with the amino compound to form the resin material, one can use such aldehydes as formaldehyde, acetaldehyde, cortonaldehyde, acrolein or compounds which produce aldehydes, e.g. hexa-methylenetetramine, paraldehyde, paraformaldehyde and the like. The preferred aminoplast is hexamethoxymethylmelamine. The weight ratio between acid resin and amino plastic will be between approx. 95:5 and approx. 70:30.
Det løsningsmiddelsystem som anvendes i belegningspreparatet, vil inkludere alkoholer, alkoksyetanoler, ketoner og alkyletere av dietylenglykol. Egnede alkoholer er slike som har mellom ca. 2 og ca-. 8 karbonatomer og som har et kokepunkt på The solvent system used in the coating preparation will include alcohols, alkoxyethanols, ketones and alkyl ethers of diethylene glycol. Suitable alcohols are those that have between approx. 2 and approx. 8 carbon atoms and which has a boiling point of
opp til ca. 180°C. Ikke-begrensende eksempler på anvendelige alkoholer inkluderer spesielle denaturerte etanoler (formel 1), propanol, butanol, isobutanol, t-butanol, pentanol, heksanol, 2-metylpentanol, 3-metylpentanol, heptanol, isoheptanol, oktanol, isooktanol og 2-etylheksanol. up to approx. 180°C. Non-limiting examples of useful alcohols include particular denatured ethanols (formula 1), propanol, butanol, isobutanol, t-butanol, pentanol, hexanol, 2-methylpentanol, 3-methylpentanol, heptanol, isoheptanol, octanol, isooctanol and 2-ethylhexanol.
De alkoksyetanoler som er anvendelige, er slike som har mellom 1 og 6 karbonatomer i alkoksygruppen. Ikke-begrensende eksempler inkluderer metoksyetanol, etoksyetanol, butoksyetanol og heksoksyetanol. Propoksypropanol og butoksypropanol er også anvendelige. The alkoxyethanols which are applicable are those which have between 1 and 6 carbon atoms in the alkoxy group. Non-limiting examples include methoxyethanol, ethoxyethanol, butoxyethanol, and hexoxyethanol. Propoxypropanol and butoxypropanol are also applicable.
De ketoner som er anvendelige, er alifatiske ketonerThe ketones that are useful are aliphatic ketones
som inneholder mellom 3 og 8 karbonatomer.- Ikke-begrensende eksempler på anvendelige ketoner er aceton, dietylketon, metyletylketon metyl<p>ropylketon, metylisobutylketon, metylamylketon, metylheksylketon, etylpropylketon, etylbutylketon, etylamylketon og metoksyaceton. which contain between 3 and 8 carbon atoms.- Non-limiting examples of usable ketones are acetone, diethyl ketone, methyl ethyl ketone methyl<p>ropyl ketone, methyl isobutyl ketone, methyl amyl ketone, methyl hexyl ketone, ethyl propyl ketone, ethyl butyl ketone, ethyl amyl ketone and methoxy acetone.
De anvendelige alkyletere av dietylenglykol vilThe useful alkyl ethers of diethylene glycol will
inneholde mellom 1 og 4 karbonatomer i alkylgruppen. Ikke-begrensende eksempler inkluderer monometyleteren av dietylenglykol, .monoetyleteren av dietylenglykol, og monobutyleteren av dietylenglykol. contain between 1 and 4 carbon atoms in the alkyl group. Non-limiting examples include the monomethyl ether of diethylene glycol, the monoethyl ether of diethylene glycol, and the monobutyl ether of diethylene glycol.
Generelt er alkyletanoler, ketoner, og alkyletere av dietylenglykol primært løsningsmidler for harpiks og aminoplast. Lavere alkoholer, f.eks. etanol, t-butanol, assisterer også ved fukting av overflaten som belegges. Høyere alkoholer, f.eks. isooktanol, tjener også som avskummingsmidler. Ved regulering av viskositeten til det endelige belegningspreparat har høyerekokende løsningsmidler, f.eks. heksoksyetanol, tendens til å øke viskositeten, og laverekokende løsningsmidler, f.eks. butoksyetanol og metyletylketon, har tendens til å nedsette viskositeten. In general, alkyl ethanols, ketones, and alkyl ethers of diethylene glycol are primarily solvents for resins and aminoplasts. Lower alcohols, e.g. ethanol, t-butanol, also assists in wetting the surface being coated. Higher alcohols, e.g. isooctanol, also serve as defoamers. When regulating the viscosity of the final coating preparation, higher-boiling solvents, e.g. hexoxyethanol, tendency to increase viscosity, and lower boiling solvents, e.g. butoxyethanol and methyl ethyl ketone, tend to reduce viscosity.
Selvom blandinger av organiske løsningsmidler sterkt, foretrekkes, kan tilfredsstillende belegningspreparater fremstilles under anvendelse av en enkelt metoksyetanol, keton eller alkyleter av dietylenglykol. Although mixtures of organic solvents are strongly preferred, satisfactory coating compositions can be prepared using a single methoxyethanol, ketone or alkyl ether of diethylene glycol.
I det ferdige belegningspreparat vil faststoffinnnholdet (harpiks og aminoplast) ligge mellom ca. 10 og ca. 25 vekt%, fortrinnsvis ca. 20 - 23 vekt%. Det flyktige system (inklusive amin, In the finished coating preparation, the solids content (resin and aminoplast) will be between approx. 10 and approx. 25% by weight, preferably approx. 20 - 23% by weight. The volatile system (including amine,
ammoniakk eller ammoniumhydroksyd) vil ligge mellom ca. 90 vekt% og ca. 75 vekt% regnet på det ferdige belegningspreparat, fortrinnsvis ca. 77 - 80 vekt%. Ca. 65 - 90 vekt% av det flyktige system vil være vann og resten (35-10 vekt%) organiske flyktige løsningsmidler inklusive amin, ammoniakk eller ammoniumhydroksyd. Fortrinnsvis vil forholdet mellom vann og organiske flyktige materialer være ca. 70 : 30 til 80 : 20 i det flyktige system. Hver komponent i løs-ningsmiddelsystemet vil være tilstede i en mengde av mellom ca. ammonia or ammonium hydroxide) will be between approx. 90% by weight and approx. 75% by weight calculated on the finished coating preparation, preferably approx. 77 - 80% by weight. About. 65 - 90% by weight of the volatile system will be water and the rest (35-10% by weight) organic volatile solvents including amine, ammonia or ammonium hydroxide. Preferably, the ratio between water and organic volatile materials will be approx. 70:30 to 80:20 in the volatile system. Each component of the solvent system will be present in an amount of between approx.
1 vekt% og ca. 20 vekt%, regnet på vekten av det ferdige preparat.1% by weight and approx. 20% by weight, calculated on the weight of the finished preparation.
Et typisk og foretrukket løsningsmiddelsystem er definert i utførel-sesekssemplene. A typical and preferred solvent system is defined in the design examples.
I de følgende illustrerende eksempler angir alleIn the following illustrative examples all indicate
deler vektdeler, med mindre annet er angitt.parts parts by weight, unless otherwise stated.
Eksempel 1Example 1
I en reaksjonskjei ble det satset 55,4 deler avIn a reaction chain, 55.4 parts of
en 80 vekt% faststoffløsning i metyletylketon (MEK) av en diglycidyleter av bisfenol A som hadde en epoksy-ekvivalentvekt på 450 - 550 og en epoksyverdi på 0,22 basert på faststoff. an 80% by weight solids solution in methyl ethyl ketone (MEK) of a diglycidyl ether of bisphenol A which had an epoxy equivalent weight of 450-550 and an epoxy value of 0.22 based on solids.
Løsningen ble oppvarmet til 88°C og det ble tilsatt 10,02 deler bisfenol A, 5,84 deler av en blanding av 70 vekt% stearinsyre og. The solution was heated to 88°C and 10.02 parts bisphenol A, 5.84 parts of a mixture of 70% by weight stearic acid and.
30 vekt% palmitinsyre, samt 0,17 del tri-n-butylamin (katalysator). Reaksjonsblandingen ble o<p>pvarmet til 149°C, mens MEK-destillat ble fjernet etter behov. Ved 149°C ble reaksjonsblandingen holdt ved totalt tilbakeløp i to timer, og det ble tatt prøver på 30% by weight palmitic acid, as well as 0.17 part tri-n-butylamine (catalyst). The reaction mixture was heated to 149°C, while MEK distillate was removed as needed. At 149°C, the reaction mixture was held at total reflux for two hours and sampled
faststoff og epoksyverdi. Tilbakeløpsbehandlingen ble fortsatt inntil epoksy-verdien var høyst 0,008. Deretter ble reaksjonsblandingen avkjølt til 115°C, og faststoffene ble justert til 92 £ 0,5' vekti med MEK destillat. Ved 115°C ble det tilsatt 5,95 deler trimelittsyreanhydrid, og reaksjonsblandingen ble oppvarmet ved 118°C i to timer. Deretter ble det tatt prøver av reaksjonsblandingen for bestemmelse av anhydridtall, som skulle være. høyst'6,0. Etter 2 1/2 timer ved 118°C ble det tatt prøver av reaksjonsblandingen for bestemmelse av anhydridtall, og 15,06 deler n-butanol og 7,52 deler butoksyetanol ble tilsatt og holdt til blandingen var ensartet. Endelige verdier med hénsyn til syretall, anhydridtall, vekt% faststoff og molekylvekt er angitt i tabell 1. solids and epoxy value. The reflux treatment was continued until the epoxy value was at most 0.008. Then the reaction mixture was cooled to 115°C and the solids were adjusted to 92 lb 0.5' wt with MEK distillate. At 115°C, 5.95 parts of trimellitic anhydride were added, and the reaction mixture was heated at 118°C for two hours. Samples were then taken of the reaction mixture to determine the anhydride number, which should be. at most'6.0. After 2 1/2 hours at 118°C, the reaction mixture was sampled for anhydride number determination, and 15.06 parts of n-butanol and 7.52 parts of butoxyethanol were added and held until the mixture was uniform. Final values with regard to acid number, anhydride number, weight % solids and molecular weight are given in table 1.
Eksempler 2 til 9.Examples 2 to 9.
Det ble utført en rekke forsøk på lignende måte somA number of experiments were carried out in a similar manner as
i eksempel 1, med følgende unntagelser: Eksempel 2 er en laboratorie-gjentagelse av eksempel 1; eksempel 3 er en gjentagelse av eksempel 1 i "pilot plant" ; eksempel 4 anvender overskudd av stearinsyre; eksempel 5 anvender mindre stearinsyre; i eksempel 6 ble stearinsyren først omsatt, fulgt av bisfenol A; i eksempel 7 ble det anvendt mer stearinsyre og mindre bisfenol A; eksempel 8 var det samme som eksempel 2, med unntagelse av at det endelige løsningsmiddel var butyleter av dietylenglykol i stedet for 2:1 -vektforholdsblandingen av butanol og butoksyetanol som ble anvendt i de andre eksempler; og i eksempel 9 ble en større mengde av trimelittsyreanhydrid anvendt. Viktige data og sluttverdier for disse eksempler er angitt i tabell 1 sammen med eksempel 1. in Example 1, with the following exceptions: Example 2 is a laboratory repeat of Example 1; example 3 is a repetition of example 1 in "pilot plant"; example 4 uses excess stearic acid; example 5 uses less stearic acid; in example 6 the stearic acid was reacted first, followed by bisphenol A; in example 7 more stearic acid and less bisphenol A was used; Example 8 was the same as Example 2, except that the final solvent was diethylene glycol butyl ether instead of the 2:1 weight ratio mixture of butanol and butoxyethanol used in the other examples; and in Example 9 a larger amount of trimellitic anhydride was used. Important data and final values for these examples are given in table 1 together with example 1.
Eksempler 10 og 11 Examples 10 and 11
Under anvendelse av den generelle prosess fra eksempel 1 kan harpikser i henhold til oppfinnelsen fremstilles under anvendelse av relativt lavmolekylære diglycidyletere av bisfenol A. Eksempel 10 er lik eksempel 1, med unntagelse av at det anvendes en annen epoksyharpiks. I eksempel 11 er diglycidyleteren av bisfenol A forstørret med hensyn til molekylvekt med bisfenol A og deretter omsatt med stearinsyre. Using the general process from example 1, resins according to the invention can be produced using relatively low molecular weight diglycidyl ethers of bisphenol A. Example 10 is similar to example 1, with the exception that a different epoxy resin is used. In example 11, the diglycidyl ether of bisphenol A is enlarged with respect to molecular weight with bisphenol A and then reacted with stearic acid.
Sammensetningene, i deler, for disse eksempler er angitt i tabell II. The compositions, in parts, for these examples are given in Table II.
Eksempel 12 Example 12
Dette eksempel viser fremstilling av en harpiks i hvilken epoksyen har tilstrekkelig høy molekylvekt til at det ikke ble brukt noe bisfenol A, men bare stearinsyre. I en reaksjonskjei ble det satset 47,72 deler diglycidyleter av bisfenol A som hadde en epoksyekvivalentvekt på 850, og 5,35 deler metyletylketon (MEK). Blandingen ble oppvarmet til ca. 88°C for oppløsning av harpiksen (ca. 55 minutter). Deretter ble det tilsatt 15,98 deler stearinsyre og 0,19 del tri-n-butylamin, og reaksjonsblandingen ble oppvarmet til 150°C, under oppsamling av ca. 146 g MEK-destillat og holdt ved 150°C i 2 timer. Efter 1,5 timer viste en prøve av reaksjonsblandingen en epoksyverdi på 0,004. MEK-destillatet ble.tilsatt tilbake til reaksjonsblandingen, og det ble tilsatt 6,30 deler trimellittsyreanhydrid. Reaksjonsblandingen ble oppvarmet til tilbakeløp ved ca. 116°C, under fjerning av 11-12 g MEK-déstillat og ble holdt ved tilbakeløp i 2,5 timer. Det ble tatt prøver av blandingen, og blandingen ble deretter redusert med 12,23 deler butoksyetanol og 12,23 deler t-butanol. Sluttverdiene for harpiksløsningen var: This example shows the production of a resin in which the epoxy has a sufficiently high molecular weight that no bisphenol A was used, but only stearic acid. In a reaction chain, 47.72 parts of diglycidyl ether of bisphenol A, which had an epoxy equivalent weight of 850, and 5.35 parts of methyl ethyl ketone (MEK) were charged. The mixture was heated to approx. 88°C for dissolution of the resin (approx. 55 minutes). Then 15.98 parts of stearic acid and 0.19 parts of tri-n-butylamine were added, and the reaction mixture was heated to 150°C, collecting approx. 146 g of MEK distillate and held at 150°C for 2 hours. After 1.5 hours, a sample of the reaction mixture showed an epoxy value of 0.004. The MEK distillate was added back to the reaction mixture and 6.30 parts trimellitic anhydride was added. The reaction mixture was heated to reflux at approx. 116°C, removing 11-12 g of MEK distillate and was held at reflux for 2.5 hours. Samples of the mixture were taken and the mixture was then reduced with 12.23 parts of butoxyethanol and 12.23 parts of t-butanol. The final values for the resin solution were:
Følgende eksempler 13-15 illustrerer fremstilling The following examples 13-15 illustrate preparation
av belegningspreparater som anvender harpiksene i henhold til oppfinnelsen. of coating preparations using the resins according to the invention.
Eksempel 13Example 13
En blanding av 28,9 3 deler av det produkt som er beskrevet i eksempel 1, 2,25 deler heksametoksymetylmelamin, A mixture of 28.9 3 parts of the product described in Example 1, 2.25 parts of hexamethoxymethylmelamine,
3,37 deler n-butanol, 0,30 del heksoksyetanol og 0,37 del butyleter av dietylenglykol ble omrørt til blandingen var jevn, mens temperaturen ikke ble tillatt å overskride 54°C. Deretter ble det tilsatt 1,29 deler denaturert alkohol ("Synasol"), som inneholder denatureringsmidler i forholdene 100 liter spesial-.denaturert alkohol av formel 1, 1 liter metylisobutylketon, 1 liter etylacetat og 1 liter flybensin. Dette ble omrørt til blandingen var ensartet. Det ble tilsatt en forhåndslaget blanding av 1,30 deler vandig ammoniakk (26° Baumé) og 2,19 deler avionisert vann. Dette ble omrørt til ensartet blanding og deretter fortynnet med 60,00 deler avionisert vann. 3.37 parts n-butanol, 0.30 part hexoxyethanol and 0.37 part butyl ether of diethylene glycol were stirred until the mixture was smooth, while the temperature was not allowed to exceed 54°C. Then 1.29 parts of denatured alcohol ("Synasol") were added, which contain denaturants in the proportions 100 liters of special denatured alcohol of formula 1, 1 liter of methyl isobutyl ketone, 1 liter of ethyl acetate and 1 liter of jet fuel. This was stirred until the mixture was uniform. A pre-made mixture of 1.30 parts aqueous ammonia (26° Baumé) and 2.19 parts deionized water was added. This was stirred to a uniform mixture and then diluted with 60.00 parts of deionized water.
Det endelige belegningspreparat har et faststoffinnhold på 22,63 vekt%, inneholdende 90,06 vekt% harpiks fra eksempel 1 The final coating preparation has a solids content of 22.63% by weight, containing 90.06% by weight of resin from example 1
og 9,94 vekt% heksametoksymetylmelamin. pH-verdien var 8,5-9,0. and 9.94% by weight hexamethoxymethylmelamine. The pH value was 8.5-9.0.
Eksempler 14 og 15Examples 14 and 15
I en alternativ blandeprosess ble n-butanol, butoksyetanol og heksametoksymetylmelamin satset, og agitering ble igangsatt. Det produkt som er beskrevet i eksempel 1, ble tilsatt og omrørt til ensartet blanding, mens temperaturen ikke ble tillatt å overskride 49°C. En forhåndslaget blanding av vandig ammoniakk (26° Baumé) og avionisert vann ble tilsatt og omrørt til ensartethet. Endelig ble blandingen fortynnet med avionisert In an alternative mixing process, n-butanol, butoxyethanol and hexamethoxymethylmelamine were charged, and agitation was initiated. The product described in example 1 was added and stirred to a uniform mixture, while the temperature was not allowed to exceed 49°C. A premade mixture of aqueous ammonia (26° Baumé) and deionized water was added and stirred until uniform. Finally, the mixture was diluted with deionized water
.vann for frembringelse av det endelige belegningspreparat. Komponentmengdene, i deler, i hvert eksempel 14 og 15 og viktige data angående de endelige belegningspreparater er gjengitt i tabell III. .water for producing the final coating preparation. The component amounts, in parts, in each of Examples 14 and 15 and important data regarding the final coating preparations are reproduced in Table III.
Belegningspreparatet i henhold til oppfinnelsen er for det første nyttig ved belegning av aluminium, tinnbelagt stål, forhåndsbehandlede metaller, stål og metaller som er belagt med det samme eller et annet harpikspreparat (dvs. et belegg nr. 2). Belegningspreparatet kan imidlertid anvendes for belegning av andre substrater så som tre, papir og lær. Den mest foretrukne og nyttige anvendelse av belegningspreparatet er for innvendig belegning av metallbeholdere som vil komme i kontakt med mat eller drikke. Belegningen kan utføres ved hvilken som helst belegningsmetode som er velkjent for fagmannen på området, inklusive direkte valsebelegning, reversert valsebelegning, elektrodeponering, sprøyting, flyt-belegning og lignende. Den foretrukne metode ved belegning av det indre av metallbeholdere er imidlertid sprøyting. Etter belegning av substratet innbrennes belegget i fra ca. 5 sekunder til ca. 5 minutter ved mellom ca. 121°C og ca. 316°C. En typisk innbrenning foregår i ca. The coating preparation according to the invention is, firstly, useful for coating aluminium, tin-coated steel, pre-treated metals, steel and metals coated with the same or another resin preparation (ie a coating no. 2). However, the coating preparation can be used for coating other substrates such as wood, paper and leather. The most preferred and useful application of the coating composition is for the interior coating of metal containers that will come into contact with food or drink. The coating can be carried out by any coating method well known to the person skilled in the art, including direct roller coating, reversed roller coating, electrodeposition, spraying, flow coating and the like. However, the preferred method of coating the interior of metal containers is spraying. After coating the substrate, the coating is burned in from approx. 5 seconds to approx. 5 minutes at intervals of approx. 121°C and approx. 316°C. A typical burn-in takes place in approx.
2 minutter ved ca. 204°C.2 minutes at approx. 204°C.
Belegningspreparatene i henhold til eksemplene 13, 14The coating preparations according to examples 13, 14
og 15 ble testet med hensyn på adhesjon, pasteurisert adhesjon og "blomstring". Adhesjonstesten utføres ved kryss-skravering av et belagt område med individuelle ripelinjer som var tilnærmet 1,6 mm fra hverandre. "Scotch"-klebebåndet festes godt til det kryss-skraverte område•og fjernes med en rask avrivning. Mengden av belegg som forblir på panelet, anslås visuelt og graderes på and 15 were tested for adhesion, pasteurized adhesion and "bloom". The adhesion test is performed by cross-hatching a coated area with individual scratch lines that were approximately 1.6 mm apart. The "Scotch" tape adheres firmly to the cross-hatched area•and is removed with a quick tear. The amount of coating remaining on the panel is visually estimated and graded on
en 0-10 skala (10 = perfekt adhesjon). Pasteurisering utføres ved neddypping av de belagte paneler i vann ved 62,8°C i 30 minutter. Deretter tørkes panelene av med absorberende håndklær, og adhesjonstesten utføres som beskrevet ovenfor. Mengden av utblomstring graderes på det pasteuriserte panel under anvendelse av en skala som går fra 0-10, hvor 0 betyr kraftig utblomstring og 10 ingen utblomstring. a 0-10 scale (10 = perfect adhesion). Pasteurization is carried out by immersing the coated panels in water at 62.8°C for 30 minutes. The panels are then dried with absorbent towels and the adhesion test is carried out as described above. The amount of efflorescence is graded on the pasteurized panel using a scale ranging from 0-10, where 0 means heavy efflorescence and 10 no efflorescence.
Eksempel 16Example 16
Behandlede aluminium-testpaneler ble belagt med belegningspreparatene fra eksemplene 13, 14 og 15 med en stav-belegger til en filmvekt på 2,5-3,0 mg pr. 6,45 cm 2. Disse testpaneler viste en adhesjonskarakter på 10 i adhesjonstesten. Treated aluminum test panels were coated with the coating compositions of Examples 13, 14 and 15 with a stick coater to a film weight of 2.5-3.0 mg per 6.45 cm 2. These test panels showed an adhesion grade of 10 in the adhesion test.
I pasteuriseringstesten fikk panelene en karakter på 10 i adhesjon og 10 i utblomstring. In the pasteurization test, the panels received a grade of 10 in adhesion and 10 in efflorescence.
Effekten av et belegg på aromaen til et innpakket produkt bestemmes i en aromadifferanse-evaluering. Flasker med øl av handelskvalitet avkjøles til ca. 4,4-7,2°C og åpnes. Ark av aluminiumfolgLe (0,00254 mm) stavbelegges på begge sider med det belegg som skal vurderes, og innbrennes. Deretter rulles et ark av folie lett og innføres i hver ølflaske, og flasken lukkes med et nytt deksel. The effect of a coating on the aroma of a wrapped product is determined in an aroma difference evaluation. Bottles of commercial quality beer are cooled to approx. 4.4-7.2°C and opens. Sheets of aluminum foil (0.00254 mm) are rod-coated on both sides with the coating to be evaluated and burned in. A sheet of foil is then lightly rolled and inserted into each beer bottle, and the bottle is closed with a new lid.
For. sammenligningens skyld forsynes ytterligere flasker med det samme øl med ruller av aluminiumfolie som er belagt på begge sider med et akseptert kommersielt belegg for innvendig belegning (løsningsmiddelbasert epoksybelegg) og innbrennes. Testbelegget og kontrollbelegget ble innbrent i 30 sekunder ved 204°C metalltemperatur. For. for the sake of comparison, additional bottles of the same beer are provided with rolls of aluminum foil coated on both sides with an accepted commercial interior coating (solvent-based epoxy coating) and fired. The test coating and the control coating were baked in for 30 seconds at 204°C metal temperature.
Etter lagring i 3 dager ved 37,8°C avkjøles flaskene med øl igjen og smaksvurderes av 9 erfarne smakere som sammenligner testbeleggene mot kontrollprøven. Det aritmetiske middel av karakterene beregnes (x). Deretter ekskluderes alle karakterer uten for x ± 2, og det beregnes et nytt gjennomsnitt, hvilket blir kvalitetskarakteren (QR). Følgende karakterskala ble brukt på basis av 1-9. After storage for 3 days at 37.8°C, the bottles of beer are cooled again and tasted by 9 experienced tasters who compare the test coatings against the control sample. The arithmetic mean of the grades is calculated (x). All grades except for x ± 2 are then excluded, and a new average is calculated, which becomes the quality grade (QR). The following grading scale was used on the basis of 1-9.
1 = ingen aromaforskjell1 = no aroma difference
1,0-1,5 = utmerket aroma1.0-1.5 = excellent aroma
1,5-2,0 = meget god aroma1.5-2.0 = very good aroma
2,0-2,5 = god aroma2.0-2.5 = good aroma
2,5-3,0 = akseptabel aroma2.5-3.0 = acceptable aroma
>3,0= ikke akseptabel>3.0= not acceptable
I ikke-pasteurisert øl anvendes n-heptyl-p-hydroksy-benzoat i en mengde av 12 ppm for inhibering av vekst av mikro-organismer. Det er svært ønskelig at det anvendes et belegg for In non-pasteurized beer, n-heptyl-p-hydroxybenzoate is used in an amount of 12 ppm to inhibit the growth of micro-organisms. It is highly desirable that a coating is used for
■ det innvendige av metallbeholdere. for øl som ikke absorberer noen særlig mengde av n-hepty1-p-hydroksybenzoatet (dette selges under handelsbetegnelsen "Staypro". ■ the interior of metal containers. for beer which does not absorb any significant amount of the n-hepty1-p-hydroxybenzoate (this is sold under the trade name "Staypro".
Denne egenskap testes under anvendelse av et simulert øl, en vandig løsning av 8 vol.% etanol og 12 ppm "Staypro". Ølbeholdere av metall belegges innvendig med det belegningspreparat som skal testes, og innbrennes. i den vanlige innbrennings-cyklus, f.eks. 2 minutter ved 204°C. Deretter fylles beholderne med simulert øl og lagres ved romtemperatur i 1 uke. Ved slutten av uken analyseres det simulerte øl for bestemmelse av mengden av gjenværende hepty1-p-hydroksybenzoat. Dette gjøres ved måling av lystransmisjon på et spektrofotometer ved en bølgelengde på.255 millimikron, i sammenligning med originalprøven. This property is tested using a simulated beer, an aqueous solution of 8 vol.% ethanol and 12 ppm "Staypro". Metal beer containers are coated internally with the coating preparation to be tested, and burned in. in the usual burn-in cycle, e.g. 2 minutes at 204°C. The containers are then filled with simulated beer and stored at room temperature for 1 week. At the end of the week, the simulated beer is analyzed to determine the amount of remaining hepty1-p-hydroxybenzoate. This is done by measuring light transmission on a spectrophotometer at a wavelength of .255 millimicrons, in comparison with the original sample.
Eksempler 17, 18 og 19Examples 17, 18 and 19
Under anvendelse av harpikser som beskrevet i eksemplene 1 og 9, samt i eksempel 1 i henhold til US-patent nr. 4.105.614, ble det laget belegningspreparater ved den frem-gangsmåte som er angitt i eksempel 14. Hvert preparat inneholdt 10 vekt% (på faststoffbasis) heksametoksymetylmelamin, og det flyktige system hadde et volumprosentforhold vann/organiske fast-stoffer på '80/20. Preparatene ble anvendt for testing ved karaktergivning av øl-aroma, og for resistens overfor absorpsjon av n-hepty1-p-hydroksybenzoat. Viktige data og testresultater er gjengitt i tabell IV. Using resins as described in examples 1 and 9, as well as in example 1 according to US patent no. 4,105,614, coating preparations were made by the method indicated in example 14. Each preparation contained 10% by weight (on a solids basis) hexamethoxymethylmelamine, and the volatile system had a volume percent water/organic solids ratio of '80/20. The preparations were used for testing when characterizing beer aroma, and for resistance to absorption of n-hepty1-p-hydroxybenzoate. Important data and test results are reproduced in Table IV.
Lagringsstabilitet (shelf life) for et belegningspreparat måles ved forandring i viskositet. En signifikantøkning i viskositet er ikke ønskelig. Et belegningspreparat som beskrevet i eksempel 17, og for sammenligningens skyld, ef belegningspreparat som beskrevet i eksempel 19, ble anbragt i forede belegningsbeholdere og lagret ved 26,7°C. Preparatene ble periodisk testet med hensyn på viskositet ved 26,7°C under anvendelse av Zahn-cup nr. 2. Resultatene er gjengitt i tabell V. Storage stability (shelf life) for a coating preparation is measured by changes in viscosity. A significant increase in viscosity is not desirable. A coating preparation as described in Example 17, and for the sake of comparison, if coating preparation as described in Example 19, were placed in lined coating containers and stored at 26.7°C. The preparations were periodically tested for viscosity at 26.7°C using Zahn cup No. 2. The results are reproduced in Table V.
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NO783432A NO783432L (en) | 1978-10-10 | 1978-10-10 | WATERLESS RESIN FOR USE IN A COATING PREPARATION |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NO783432A NO783432L (en) | 1978-10-10 | 1978-10-10 | WATERLESS RESIN FOR USE IN A COATING PREPARATION |
Publications (1)
Publication Number | Publication Date |
---|---|
NO783432L true NO783432L (en) | 1980-04-11 |
Family
ID=19884479
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO783432A NO783432L (en) | 1978-10-10 | 1978-10-10 | WATERLESS RESIN FOR USE IN A COATING PREPARATION |
Country Status (1)
Country | Link |
---|---|
NO (1) | NO783432L (en) |
-
1978
- 1978-10-10 NO NO783432A patent/NO783432L/en unknown
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