WO1979000732A1 - Water soluble epoxy ester copolymers for sanitary can use - Google Patents
Water soluble epoxy ester copolymers for sanitary can use Download PDFInfo
- Publication number
- WO1979000732A1 WO1979000732A1 PCT/US1979/000110 US7900110W WO7900732A1 WO 1979000732 A1 WO1979000732 A1 WO 1979000732A1 US 7900110 W US7900110 W US 7900110W WO 7900732 A1 WO7900732 A1 WO 7900732A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- epoxy ester
- acid
- recited
- copolymer
- ester copolymer
- Prior art date
Links
- 239000004593 Epoxy Substances 0.000 title claims abstract description 40
- 229920001577 copolymer Polymers 0.000 title claims abstract description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 239000002253 acid Substances 0.000 claims abstract description 31
- 239000000178 monomer Substances 0.000 claims abstract description 19
- 150000002148 esters Chemical class 0.000 claims abstract description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 15
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 9
- 239000005711 Benzoic acid Substances 0.000 claims abstract description 8
- 235000010233 benzoic acid Nutrition 0.000 claims abstract description 8
- 150000001412 amines Chemical class 0.000 claims abstract description 6
- 150000001991 dicarboxylic acids Chemical class 0.000 claims abstract description 6
- 229920005989 resin Polymers 0.000 claims abstract description 6
- 239000011347 resin Substances 0.000 claims abstract description 6
- 238000005886 esterification reaction Methods 0.000 claims abstract description 5
- 229920003180 amino resin Polymers 0.000 claims abstract description 4
- 229920001568 phenolic resin Polymers 0.000 claims abstract description 4
- 229920000728 polyester Polymers 0.000 claims abstract description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 3
- 150000003839 salts Chemical class 0.000 claims abstract 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 18
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 11
- 239000001530 fumaric acid Substances 0.000 claims description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 5
- 239000006185 dispersion Substances 0.000 claims description 4
- SMNNDVUKAKPGDD-UHFFFAOYSA-N 2-butylbenzoic acid Chemical group CCCCC1=CC=CC=C1C(O)=O SMNNDVUKAKPGDD-UHFFFAOYSA-N 0.000 claims description 3
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 3
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 claims description 3
- 229930185605 Bisphenol Natural products 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 2
- 150000002118 epoxides Chemical group 0.000 claims description 2
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical group ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical compound NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 abstract description 2
- 150000001559 benzoic acids Chemical class 0.000 abstract 1
- 125000003700 epoxy group Chemical group 0.000 abstract 1
- 230000009257 reactivity Effects 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000796 flavoring agent Substances 0.000 description 4
- 235000019634 flavors Nutrition 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- BNCADMBVWNPPIZ-UHFFFAOYSA-N 2-n,2-n,4-n,4-n,6-n,6-n-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound COCN(COC)C1=NC(N(COC)COC)=NC(N(COC)COC)=N1 BNCADMBVWNPPIZ-UHFFFAOYSA-N 0.000 description 3
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 3
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 229960002887 deanol Drugs 0.000 description 3
- 239000012972 dimethylethanolamine Substances 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000005643 Pelargonic acid Substances 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- -1 ammonia Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001246 colloidal dispersion Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000012632 extractable Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000012943 hotmelt Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
- C08G59/4292—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof together with monocarboxylic acids
-
- 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
Definitions
- the present invention relates to water soluble epoxy ester copolymers which are particularly adapted to sanitary can use where good resistance to extraction by hot water and good odor and flavor characteristics are essential.
- Background Art Water solution coating compositions have been employed for diverse purposes, but it has been difficult to obtain the good resistance to extraction by hot water and good odor and flavor characteristics which are important to enable application of the coatings to sanitary cans.
- a relatively low molecular. weight polyepoxide having an average molecular weight of about 300 to about 1100 (by calculation) and a 1, 2-epoxy equivalency of about 1.4 to about 2.0 is esterified with an at least approximately stoichio-metric proportion, based on epoxide functionality, of monocarboxylic acid selected from benzoic acid, a C 1 -C 8 alkyl substituted benzoic acid, or a C 6 -C 10 alkanoic acid to produce an ester derivative substantially free of epoxy functionality.
- This esterification reaction is continued to an acid number of less than 20.
- the resulting hydroxy functional epoxy ester is then polyesterified with a monoethylenic dicarboxylic acid which resists homopolymerization, preferably fumaric acid.
- polyesterification reaction From 1.5-8% of the diacid is used in the polyesterification reaction, based on the weight, of the epoxy ester, so the hydroxy groups in the epoxy ester are present in stoichiometric excess, and the polyesterification is continued to an acid number of less than 20 to provide an ethylenically unsaturated hydroxy functional poly- ester.
- This unsaturated polyester is then copolymerized with from 15% to 70% of monoethylenic monomers, based on the weight of the copolymer, to provide a copolymer product.
- These monomers include monoethylenic carboxylic acid, such as methacrylic acid or fumaric acid, to provide an acid number of from 20-100 in the final copolymer so that amine and water can be added to provide a water dispersion which is either a solution or a colloidal dispersion.
- Reactive monomers such as hydroxyethyl acrylate or N-methylol acrylamide or its ether, such as the butyl ether, may be used.
- an aminoplast such as hexamethoxy methyl melamine, or a water soluble or dispersible phenoplast, or a mixture thereof, may be used for cure.
- the polyepoxides preferably have a 1, 2-epoxy equivalency of about 1.4 to about 2.0 and the best properties are obtained using diglycidyl ethers of a bisphenol, such as bisphenol A.
- the preferred molecular weight of the polyepoxides which may be provided by the use of mixtures, is from 350 to 800.
- the saturated monocarboxylie acid used to consume the epoxy functionality may be benzoic acid or a C 1 -C 8 alkyl substituted benzoic acid or a C 6 -C 10 alkanoic acid, but para tertiary butyl benzoic acid is particularly preferred.
- the C 6 -C 10 alkanoic acids are less preferred and are illustrated by hexoic acid or pelar- gonic acid.
- These saturated monocarboxylic acids uniquely provide maximum impermeability in the combination of this invention.
- the esterification reaction is wholly conventional, simple heating to a hot melt, desirably in the presence of a trace of amine catalyst, being all that is needed.
- the acid is used in at least approximately stoichiometric proportion and the reaction is continued to consume most of the acid, an acid number of less than about 20, preferably less than 10, being contemplated.
- Significant residual epoxy functionality yields instability and should be avoided. Some excess acid will simply react with the hydroxy functionality on the epoxy ester. It is here noted that polyepoxides frequently contain hydroxy groups, and even if they do not, the carboxy-epoxy reaction produces hydroxy groups, so the epoxy ester which is formed is hydroxy functional. Substantially stoichiometric proportions are preferred.
- the monoethylenically unsaturated dicarboxylic acid should resist homopolymerization so that its acidity can be substantially consumbed in the production of a polyester with the hydroxyl functional epoxy ester without consuming the unsaturation.
- the preferred dicarboxylic acid is fumaric acid, but maleic acid or maleic anhydride can also be used.
- This polyester now contains polymerizable unsaturation and it is copolymerized with monoethylenic monomers, the bulk of which (at least about 50% by weight) are nonreactive. This means that, aside from their polymerizable unsaturation, they do not react under the conditions of polymerization and use which are contemplated. A similar statement is that there are no functional groups except the polymerizable ethylenic group. Styrene and vinyl toluene are particularly contemplated, though methyl methacrylate, methyl acrylate, ethyl acrylate, acrylonitrile and vinyl acetate will further illustrate the useful materials. Styrene and vinyl toluene are especially important for two reasons.
- a monoethylenic carboxylic acid of any desired type should be employed to provide an acid number of from 20-100 in the final copolymer. Fumaric acid and maleic acid are preferred because these are F.D.A. approved, but acrylic acid, methacrylic acid, crotonic acid and itaconic acid are all useful, and one cannot know which acids will be a-proved for sanitary can use in the future. Maleic anhydride is useful at the smaller proportion of use.
- the preferred acidity should not exceed 60. While more acid polymers can be used, sanitary can use requires maximum water resistance and good resistance to water extraction, and these are best at low acid value.
- the copolymers herein are well adapted to disperse in water at low acid value.
- Other reactive monoethylenic monomers may be included in an amount up to about 20% of the total polymerizable monomers. These are illustrated by hydroxy monomers, such as 2-hydroxyethyl acrylate, amide monomers, such as acrylamide, N-methylol functional monomers, such as N-methylol acrylamide or ethers thereof like the butyl ether.
- the copolymerization is itself conventional being carried out in organic solvent solution using a free radical generating polymerization catalyst. These are well known and are illustrated in the Example.
- aminoplast and phenoplast resins which may be used for cure are also well known and will be illustrated by hexamethoxymethyl melamine.
- This class of water soluble and water dispersible materials useful for curing hydroxy functional resins is a matter of common knowledge in the art. They are used in an amount of 5-40% of total resin solids.
- An amine including ammonia, is added to allow the acidic copolymer to be dispersed in water. This is again conventional, and is illustrated using dimethyl ethanol amine.
- the resulting aqueous solutions cure to provide films characterized by superior resistance to extraction and they resist absorbing odor and flavor components of the foods and beverages which are packaged. They can be applied to any metal can interior, such as aluminum, steel and tin plated steel. Spray appication and cure by baking at 400°F. for 3 minutes are particularly contemplated. Films of about 0.2-0.3 mil are formed. Good adhesion is obtained on all of these surfaces.
- the final product is a milky dispersion having the following characteristics: Nonvolatile solids 30.1%; Acid value of solids - 33.5.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Paints Or Removers (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US88503678A | 1978-03-09 | 1978-03-09 | |
| US885036 | 1997-06-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1979000732A1 true WO1979000732A1 (en) | 1979-10-04 |
Family
ID=25385977
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1979/000110 WO1979000732A1 (en) | 1978-03-09 | 1979-03-09 | Water soluble epoxy ester copolymers for sanitary can use |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0015917A1 (enrdf_load_stackoverflow) |
| JP (1) | JPS55500154A (enrdf_load_stackoverflow) |
| CA (1) | CA1117690A (enrdf_load_stackoverflow) |
| WO (1) | WO1979000732A1 (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0042426A4 (en) * | 1979-12-28 | 1982-05-10 | Desoto Inc | WATER-SOLUBLE COPOLYMERS OF EPOXYESTER FOR USE IN THE INSIDE OF CAN. |
| WO1990010677A1 (en) * | 1987-04-10 | 1990-09-20 | Lowell Cummings | Water-based coating compositions |
| WO2002083801A3 (fr) * | 2001-04-06 | 2003-03-13 | Kansai Paint Co Ltd | Composition aqueuse de revetement pour surface interne d'une boite et procede de revetement de surface interne de boite |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5318462B2 (ja) * | 2008-05-23 | 2013-10-16 | 互応化学工業株式会社 | カルボキシル基含有樹脂及びその硬化物 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3564074A (en) * | 1966-11-28 | 1971-02-16 | Dow Chemical Co | Thermosetting vinyl resins reacted with dicarboxylic acid anhydrides |
| US4101398A (en) * | 1971-04-01 | 1978-07-18 | Hoechst Aktiengesellschaft | Process for hardening a resin which is the reaction product of an epoxy resin, an olefinically unsaturated monocarboxylic acid and a polycarboxylic acid anhydride unit |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3773856A (en) * | 1971-11-11 | 1973-11-20 | E Takiyama | Process for the preparation of unsaturated epoxy ester compositions |
| JPS5296690A (en) * | 1976-02-10 | 1977-08-13 | Dainippon Ink & Chem Inc | Rapidly curable photo-setting resin composition |
| US4098735A (en) * | 1977-02-14 | 1978-07-04 | Mobil Oil Corporation | Water reducible epoxy ester using monocarboxylic acid to control molecular weight |
-
1979
- 1979-03-09 JP JP50051479A patent/JPS55500154A/ja active Pending
- 1979-03-09 WO PCT/US1979/000110 patent/WO1979000732A1/en unknown
- 1979-03-09 CA CA000323074A patent/CA1117690A/en not_active Expired
- 1979-10-09 EP EP79900275A patent/EP0015917A1/en not_active Withdrawn
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3564074A (en) * | 1966-11-28 | 1971-02-16 | Dow Chemical Co | Thermosetting vinyl resins reacted with dicarboxylic acid anhydrides |
| US4101398A (en) * | 1971-04-01 | 1978-07-18 | Hoechst Aktiengesellschaft | Process for hardening a resin which is the reaction product of an epoxy resin, an olefinically unsaturated monocarboxylic acid and a polycarboxylic acid anhydride unit |
Non-Patent Citations (1)
| Title |
|---|
| See also references of EP0015917A4 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0042426A4 (en) * | 1979-12-28 | 1982-05-10 | Desoto Inc | WATER-SOLUBLE COPOLYMERS OF EPOXYESTER FOR USE IN THE INSIDE OF CAN. |
| WO1990010677A1 (en) * | 1987-04-10 | 1990-09-20 | Lowell Cummings | Water-based coating compositions |
| WO2002083801A3 (fr) * | 2001-04-06 | 2003-03-13 | Kansai Paint Co Ltd | Composition aqueuse de revetement pour surface interne d'une boite et procede de revetement de surface interne de boite |
| US6893678B2 (en) | 2001-04-06 | 2005-05-17 | Kansai Paint Co., Ltd. | Water-based coating composition for inner surface of can and method of coating inner surface of can |
| CN100343351C (zh) * | 2001-04-06 | 2007-10-17 | 关西涂料株式会社 | 用于容器内表面的水基涂料组合物和容器内表面的涂布方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA1117690A (en) | 1982-02-02 |
| EP0015917A4 (en) | 1980-07-17 |
| EP0015917A1 (en) | 1980-10-01 |
| JPS55500154A (enrdf_load_stackoverflow) | 1980-03-21 |
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