GB1117126A - Preparation of resins for use in water-thinnable compositions - Google Patents
Preparation of resins for use in water-thinnable compositionsInfo
- Publication number
- GB1117126A GB1117126A GB3769165A GB3769165A GB1117126A GB 1117126 A GB1117126 A GB 1117126A GB 3769165 A GB3769165 A GB 3769165A GB 3769165 A GB3769165 A GB 3769165A GB 1117126 A GB1117126 A GB 1117126A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- anhydride
- water
- mixtures
- methacrylic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000203 mixture Substances 0.000 title abstract 5
- 229920005989 resin Polymers 0.000 title abstract 2
- 239000011347 resin Substances 0.000 title abstract 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 abstract 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 150000008064 anhydrides Chemical class 0.000 abstract 3
- 238000001035 drying Methods 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 abstract 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 2
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 2
- 229930195729 fatty acid Natural products 0.000 abstract 2
- 239000000194 fatty acid Substances 0.000 abstract 2
- 150000004665 fatty acids Chemical class 0.000 abstract 2
- 239000003112 inhibitor Substances 0.000 abstract 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 abstract 2
- 239000000178 monomer Substances 0.000 abstract 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 abstract 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 abstract 1
- 239000004342 Benzoyl peroxide Substances 0.000 abstract 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 abstract 1
- 229920000877 Melamine resin Polymers 0.000 abstract 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 235000011037 adipic acid Nutrition 0.000 abstract 1
- 239000001361 adipic acid Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 1
- 239000004202 carbamide Substances 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001244 carboxylic acid anhydrides Chemical group 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000008199 coating composition Substances 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- 229960002887 deanol Drugs 0.000 abstract 1
- 150000002118 epoxides Chemical group 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 abstract 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract 1
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 abstract 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 229920005862 polyol Polymers 0.000 abstract 1
- 150000003077 polyols Chemical class 0.000 abstract 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/46—Polyesters chemically modified by esterification
- C08G63/48—Polyesters chemically modified by esterification by unsaturated higher fatty oils or their acids; by resin 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
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/08—Polyesters modified with higher fatty oils or their acids, or with natural resins or resin acids
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
Ethylenically unsaturated monomers, at least one of which contains a carboxylic acid or anhydride group, are copolymerized, the acidic polymer product is esterified with a partial ester of a polyol and a C8-C20 oil fatty acid, then uncombined esterifiable groups (e.g. hydroxyl or epoxide groups) of the product are further esterified with a polybasic carboxylic acid or an anhydride thereof to a predetermined acid value, and free carboxyl groups are neutralized with a base to render the product water-soluble. The carboxylic component of the initial copolymer may be acrylic or methacrylic acid; and suitable comonomers include alkyl (C1-C10) esters of acrylic or methacrylic acid, vinyl chloride, styrene, vinyl toluene and mixtures thereof. The partial ester may be derived, on the one hand, from a drying oil, semi-drying oil or non-drying oil fatty acid and, on the other, from glycerol, ethylene glycol, pentaerythritol, trimethylol-ethane or -propane or mixtures thereof. Suitable polybasic components for further esterification include phthalic acid or its anhydride, isophthalic acid, adipic acid, trimellitic acid or its anhydride and pyromellitic anhydride and mixtures thereof. The neutralizing agent may be ammonia or an amine, e.g. triethylamine or dimethylaminoethanol. The products obtained can be thinned with water for use as coating compositions. Such compositions may also include water-miscible solvents, e.g. ethylene glycol, monoethyl or monobutyl ether or dioxane, and water-soluble resins such as urea, melamine or phenol condensates with formaldehyde, optionally modified by treatment with an alcohol. In examples, the monomers copolymerized are (a) methyl methacrylate (containing a small amount of hydroquinone inhibitor), ethyl acrylate (with similar inhibitor) and methacrylic acid, and (b) methyl methacrylate and methacrylic acid, the polymerization being effected in toluene in the presence of benzoyl peroxide.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU48957/64A AU409963B2 (en) | 1964-09-04 | 1964-09-04 | A method of manufacturing water-thinnable vinyl and acrylic modified alkyd resins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1117126A true GB1117126A (en) | 1968-06-19 |
Family
ID=3735726
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3769165A Expired GB1117126A (en) | 1964-09-04 | 1965-09-03 | Preparation of resins for use in water-thinnable compositions |
Country Status (2)
| Country | Link |
|---|---|
| AU (1) | AU409963B2 (en) |
| GB (1) | GB1117126A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4264766A (en) * | 1877-09-19 | 1981-04-28 | Hoffmann-La Roche Inc. | Immunological diagnostic reagents |
| US4910292A (en) * | 1988-10-14 | 1990-03-20 | Eastman Kodak Company | Water-dissipatable polyester resins and coatings prepared therefrom |
| US5859135A (en) * | 1992-04-16 | 1999-01-12 | Akzo Nobel Nv | Aqueous coating compositions comprising functional group-containing crosslinkable resins |
| US6166150A (en) * | 1996-09-25 | 2000-12-26 | Basf Coatings Ag | Process for preparing an aqueous dispersion of a polyacrylate-modified polyurethane-alkyd resin and the use of such a dispersion |
-
1964
- 1964-09-04 AU AU48957/64A patent/AU409963B2/en not_active Expired
-
1965
- 1965-09-03 GB GB3769165A patent/GB1117126A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4264766A (en) * | 1877-09-19 | 1981-04-28 | Hoffmann-La Roche Inc. | Immunological diagnostic reagents |
| US4910292A (en) * | 1988-10-14 | 1990-03-20 | Eastman Kodak Company | Water-dissipatable polyester resins and coatings prepared therefrom |
| US5859135A (en) * | 1992-04-16 | 1999-01-12 | Akzo Nobel Nv | Aqueous coating compositions comprising functional group-containing crosslinkable resins |
| US6166150A (en) * | 1996-09-25 | 2000-12-26 | Basf Coatings Ag | Process for preparing an aqueous dispersion of a polyacrylate-modified polyurethane-alkyd resin and the use of such a dispersion |
Also Published As
| Publication number | Publication date |
|---|---|
| AU4895764A (en) | 1966-03-10 |
| AU409963B2 (en) | 1971-01-25 |
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