GB1095953A - Aqueous stoving lacquers - Google Patents
Aqueous stoving lacquersInfo
- Publication number
- GB1095953A GB1095953A GB28443/66A GB2844366A GB1095953A GB 1095953 A GB1095953 A GB 1095953A GB 28443/66 A GB28443/66 A GB 28443/66A GB 2844366 A GB2844366 A GB 2844366A GB 1095953 A GB1095953 A GB 1095953A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- tetrahydrophthalic
- acids
- optionally
- alkyd
- 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
- 239000004922 lacquer Substances 0.000 title abstract 8
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 7
- 229930195729 fatty acid Natural products 0.000 abstract 7
- 239000000194 fatty acid Substances 0.000 abstract 7
- 150000004665 fatty acids Chemical class 0.000 abstract 7
- 229920000180 alkyd Polymers 0.000 abstract 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 5
- 239000002253 acid Substances 0.000 abstract 5
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 abstract 5
- -1 amine salts Chemical class 0.000 abstract 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 abstract 4
- NIDNOXCRFUCAKQ-UMRXKNAASA-N (1s,2r,3s,4r)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid Chemical compound C1[C@H]2C=C[C@@H]1[C@H](C(=O)O)[C@@H]2C(O)=O NIDNOXCRFUCAKQ-UMRXKNAASA-N 0.000 abstract 3
- 235000013162 Cocos nucifera Nutrition 0.000 abstract 3
- 244000060011 Cocos nucifera Species 0.000 abstract 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 3
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 abstract 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 abstract 2
- 244000068988 Glycine max Species 0.000 abstract 2
- 235000010469 Glycine max Nutrition 0.000 abstract 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 abstract 2
- 235000004443 Ricinus communis Nutrition 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 229960002887 deanol Drugs 0.000 abstract 2
- 239000012972 dimethylethanolamine Substances 0.000 abstract 2
- 150000002009 diols Chemical class 0.000 abstract 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 abstract 2
- 229920005862 polyol Polymers 0.000 abstract 2
- 150000003077 polyols Chemical class 0.000 abstract 2
- 230000009183 running Effects 0.000 abstract 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 abstract 1
- FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical class COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 abstract 1
- KNDQHSIWLOJIGP-UHFFFAOYSA-N 826-62-0 Chemical compound C1C2C3C(=O)OC(=O)C3C1C=C2 KNDQHSIWLOJIGP-UHFFFAOYSA-N 0.000 abstract 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 abstract 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 240000006240 Linum usitatissimum Species 0.000 abstract 1
- 235000004431 Linum usitatissimum Nutrition 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- 229920000877 Melamine resin Polymers 0.000 abstract 1
- 239000004640 Melamine resin Substances 0.000 abstract 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 abstract 1
- 150000001279 adipic acids Chemical class 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 150000003973 alkyl amines Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000001414 amino alcohols Chemical group 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical class OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 abstract 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 239000004359 castor oil Substances 0.000 abstract 1
- 235000019438 castor oil Nutrition 0.000 abstract 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 abstract 1
- 150000001991 dicarboxylic acids Chemical class 0.000 abstract 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 235000004426 flaxseed Nutrition 0.000 abstract 1
- 239000008098 formaldehyde solution Substances 0.000 abstract 1
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical class O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- 150000002531 isophthalic acids Chemical class 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000000944 linseed oil Substances 0.000 abstract 1
- 150000007974 melamines Chemical class 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000003607 modifier Substances 0.000 abstract 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 abstract 1
- SBOJXQVPLKSXOG-UHFFFAOYSA-N o-amino-hydroxylamine Chemical group NON SBOJXQVPLKSXOG-UHFFFAOYSA-N 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 150000003022 phthalic acids Chemical class 0.000 abstract 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000000600 sorbitol Substances 0.000 abstract 1
- 239000007921 spray Substances 0.000 abstract 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 abstract 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical class OOO JSPLKZUTYZBBKA-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
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
- C08G63/54—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation the acids or hydroxy compounds containing carbocyclic rings
- C08G63/553—Acids or hydroxy compounds containing cycloaliphatic rings, e.g. Diels-Alder adducts
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
Aqueous stoving lacquers comprise amine salts of tetrahydrophthalic or endomethylene-tetrahydrophthalic acid semiesters of alkyd resins which are fatty acid modified and contain free hydroxyl groups, said alkyd resins containing residues of polyols having three or more hydroxy groups, and optionally also of diols, and dicarboxylic acids in molar ratios of 1-1.3:1, and having acid numbers below 15 and hydroxy numbers of 90-300 before semi-esterification, the semi-esters having acid numbers of 30-80 and hydroxy numbers of 60-200. Suitable components of the alkyd are glycerol, trimethylolpropane, pentaerythritol, dipentaerythritol, and sorbitol, optionally with minor amounts of ethylene glycol, diethylene glycol, the butylene glycols and neopentylene glycol; adipic, isophthalic and phthalic acids. Suitable modifiers are castor, dehydrated castor, coconut, soya and linseed oils; soya, linseed, coconut and dehydrated castor oil fatty acids, ricinoleic and hydrogenated ricinoleic acids, natural and synthetic first runnings fatty acids and fatty acids from paraffins, and optionally also benzoic, t-butylbenzoic and resinic acids. Suitable amines are primary, secondary and tertiary alkylamines, aminoalcohols, amino-ethers, e.g. methyl-, diethyl-, triethyl-, ethanol-, diethanol-, triethanol-, N - methyl - ethanol-, N:N - dimethyl - ethanol-, 3 - propanol-, and 3 - methoxypropyl - amines and morpholine. The lacquers may also comprise water-miscible organic solvents, e.g. alcohols, ether-alcohols, esters, ketones, keto-alcohols and ethers, e.g. ethylene glycol methyl, ethyl or butyl monoethers. The neutralized product should have a pH of less than 8 in 30 solids per cent solution. In Example (1) a pentaerythritol/natural first runnings fatty acid (of A.N. 340-350)/phthalic anhydride alkyd of acid number (A.N.) 6 (molar ratios 1:0.9:0.9) is heated at 140 DEG C. for 30 minutes with tetrahydrophthalic anhydride to give a product of AN=40, which is treated with ethylene glycol monobutyl ether and dimethyl-ethanolamine and water to give a 55% lacquer solution, which is mixed with rutile TiO2 and a methylated melamine-formaldehyde solution to give a white stoving lacquer. In Example (5) the fatty acid used is a coconut/ricinoleic mixture, and in Example (6) the endomethylene tetrahydrophthalic acid semiester is prepared, the other components being the same.ALSO:Aqueous stoving lacquers contain at least one amine salt of tetrahydrophthalic acid or endomethylene tetrahydrophthalic acid semiesterified with an alkyd resin derived from at least one polyol having three or more hydroxy groups, and optionally also at least one diol, and a dicarboxylic acid, modified with a fatty acid and containing free hydroxy groups (see Division C3). In Examples lacquers are prepared from pentaerythritol-fatty acid-phthalic anhydride alkyds esterified with tetrahydrophthalic or endomethylene tetrahydrophthalic anhydride and dissolved in ethylene glycol monobutyl ether and aqueous dimethyl-ethanolamine. TiO2 and a methylated melamine resin are added and the lacquer is applied by spray gun to metal sheets, which are air-dried and stoved.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0046889 | 1965-06-24 | ||
| DEF0046426 | 1965-06-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1095953A true GB1095953A (en) | 1967-12-20 |
Family
ID=25976837
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB28443/66A Expired GB1095953A (en) | 1965-06-24 | 1966-06-24 | Aqueous stoving lacquers |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT278206B (en) |
| BE (1) | BE682926A (en) |
| CH (1) | CH463670A (en) |
| DE (2) | DE1519146A1 (en) |
| DK (1) | DK119718B (en) |
| ES (1) | ES328204A1 (en) |
| FR (1) | FR1484344A (en) |
| GB (1) | GB1095953A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4346044A (en) | 1979-07-28 | 1982-08-24 | Bayer Aktiengesellschaft | Water-soluble air-drying alkyd resins, process for their preparation and their use as bases for non-yellowing lacquers |
| US4413116A (en) * | 1981-04-14 | 1983-11-01 | Bayer Aktiengesellschaft | Process for the preparation of polyesters or alkyd resins, resins which may be obtained according to this process and the use thereof as lacquer binders |
| GB2136007A (en) * | 1982-12-30 | 1984-09-12 | Nippon Paint Co Ltd | Resinous composition its preparation and coating composition containing the same |
| AU583037B2 (en) * | 1984-05-04 | 1989-04-20 | Franz Haas Waffelmaschinen Industriegesellschaft Mbh | Process and apparatus for making rolled wafer cones |
| WO1995009880A1 (en) * | 1993-10-04 | 1995-04-13 | Ppg Industries, Inc. | Waterborne polyesters having improved saponification resistance |
| CN115677991A (en) * | 2022-11-04 | 2023-02-03 | 江苏三木化工股份有限公司 | Water-based alkyd resin with high solid content and high flash point baking varnish and preparation method thereof |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT369028B (en) * | 1981-06-12 | 1982-11-25 | Vianova Kunstharz Ag | METHOD FOR THE PRODUCTION OF AIR- AND OVEN-DRYING WATER-DETUMABLE VARNISH BINDERS |
-
1965
- 1965-06-24 DE DE19651519146 patent/DE1519146A1/en active Pending
- 1965-08-13 DE DE19651519147 patent/DE1519147A1/en active Pending
-
1966
- 1966-04-20 CH CH571966A patent/CH463670A/en unknown
- 1966-06-21 ES ES0328204A patent/ES328204A1/en not_active Expired
- 1966-06-22 BE BE682926D patent/BE682926A/en unknown
- 1966-06-22 FR FR66518A patent/FR1484344A/en not_active Expired
- 1966-06-22 DK DK321866AA patent/DK119718B/en unknown
- 1966-06-23 AT AT598966A patent/AT278206B/en not_active IP Right Cessation
- 1966-06-24 GB GB28443/66A patent/GB1095953A/en not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4346044A (en) | 1979-07-28 | 1982-08-24 | Bayer Aktiengesellschaft | Water-soluble air-drying alkyd resins, process for their preparation and their use as bases for non-yellowing lacquers |
| US4413116A (en) * | 1981-04-14 | 1983-11-01 | Bayer Aktiengesellschaft | Process for the preparation of polyesters or alkyd resins, resins which may be obtained according to this process and the use thereof as lacquer binders |
| GB2136007A (en) * | 1982-12-30 | 1984-09-12 | Nippon Paint Co Ltd | Resinous composition its preparation and coating composition containing the same |
| AU583037B2 (en) * | 1984-05-04 | 1989-04-20 | Franz Haas Waffelmaschinen Industriegesellschaft Mbh | Process and apparatus for making rolled wafer cones |
| WO1995009880A1 (en) * | 1993-10-04 | 1995-04-13 | Ppg Industries, Inc. | Waterborne polyesters having improved saponification resistance |
| US5552475A (en) * | 1993-10-04 | 1996-09-03 | Ppg Industries, Inc. | Waterborne polyesters having improved saponification resistance |
| CN115677991A (en) * | 2022-11-04 | 2023-02-03 | 江苏三木化工股份有限公司 | Water-based alkyd resin with high solid content and high flash point baking varnish and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1519147A1 (en) | 1970-09-03 |
| DK119718B (en) | 1971-02-15 |
| DE1519146A1 (en) | 1969-12-11 |
| AT278206B (en) | 1970-01-26 |
| BE682926A (en) | 1966-12-22 |
| FR1484344A (en) | 1967-06-09 |
| ES328204A1 (en) | 1967-08-01 |
| CH463670A (en) | 1968-10-15 |
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