GB1045118A - Polyhydric phenol modified fatty media and iron surfaces chelated therewith - Google Patents
Polyhydric phenol modified fatty media and iron surfaces chelated therewithInfo
- Publication number
- GB1045118A GB1045118A GB1684765A GB1684765A GB1045118A GB 1045118 A GB1045118 A GB 1045118A GB 1684765 A GB1684765 A GB 1684765A GB 1684765 A GB1684765 A GB 1684765A GB 1045118 A GB1045118 A GB 1045118A
- Authority
- GB
- United Kingdom
- Prior art keywords
- reacted
- methyl
- gallate
- linseed
- pyrogallol
- 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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title abstract 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 title 2
- 229910052742 iron Inorganic materials 0.000 title 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 18
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 abstract 18
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 abstract 13
- FBSFWRHWHYMIOG-UHFFFAOYSA-N methyl 3,4,5-trihydroxybenzoate Chemical compound COC(=O)C1=CC(O)=C(O)C(O)=C1 FBSFWRHWHYMIOG-UHFFFAOYSA-N 0.000 abstract 11
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 abstract 10
- 229920000180 alkyd Polymers 0.000 abstract 9
- 229940075579 propyl gallate Drugs 0.000 abstract 9
- 235000010388 propyl gallate Nutrition 0.000 abstract 9
- 239000000473 propyl gallate Substances 0.000 abstract 9
- 240000006240 Linum usitatissimum Species 0.000 abstract 7
- 235000004431 Linum usitatissimum Nutrition 0.000 abstract 7
- 235000004426 flaxseed Nutrition 0.000 abstract 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 6
- IBKQQKPQRYUGBJ-UHFFFAOYSA-N methyl gallate Natural products CC(=O)C1=CC(O)=C(O)C(O)=C1 IBKQQKPQRYUGBJ-UHFFFAOYSA-N 0.000 abstract 6
- 235000010678 Paulownia tomentosa Nutrition 0.000 abstract 5
- 240000002834 Paulownia tomentosa Species 0.000 abstract 5
- 239000000376 reactant Substances 0.000 abstract 5
- 239000002253 acid Substances 0.000 abstract 4
- -1 oleyl gallate Chemical compound 0.000 abstract 4
- 150000004703 alkoxides Chemical class 0.000 abstract 3
- 239000004359 castor oil Substances 0.000 abstract 3
- 235000019438 castor oil Nutrition 0.000 abstract 3
- 239000003054 catalyst Substances 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 3
- 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 3
- FDNCPIRKQFHDBX-UHFFFAOYSA-N methyl undec-2-enoate Chemical compound CCCCCCCCC=CC(=O)OC FDNCPIRKQFHDBX-UHFFFAOYSA-N 0.000 abstract 3
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 abstract 2
- 229910000831 Steel Inorganic materials 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 150000001298 alcohols Chemical class 0.000 abstract 2
- INPLRNDUHADSET-UHFFFAOYSA-N butan-1-olate;iron(2+) Chemical compound [Fe+2].CCCC[O-].CCCC[O-] INPLRNDUHADSET-UHFFFAOYSA-N 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 238000000354 decomposition reaction Methods 0.000 abstract 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical class O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 abstract 2
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 abstract 2
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 239000000944 linseed oil Substances 0.000 abstract 2
- 235000021388 linseed oil Nutrition 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 2
- 150000004702 methyl esters Chemical class 0.000 abstract 2
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 abstract 2
- 229940073769 methyl oleate Drugs 0.000 abstract 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 abstract 2
- 229940079877 pyrogallol Drugs 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 239000010959 steel Substances 0.000 abstract 2
- 239000002966 varnish Substances 0.000 abstract 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 abstract 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 abstract 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 1
- 229910019142 PO4 Inorganic materials 0.000 abstract 1
- 239000004952 Polyamide Substances 0.000 abstract 1
- 235000019485 Safflower oil Nutrition 0.000 abstract 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 abstract 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000011248 coating agent Substances 0.000 abstract 1
- 239000008199 coating composition Substances 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical class O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 abstract 1
- 239000003822 epoxy resin Substances 0.000 abstract 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 229940074391 gallic acid Drugs 0.000 abstract 1
- 235000004515 gallic acid Nutrition 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 1
- 150000002506 iron compounds Chemical class 0.000 abstract 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 abstract 1
- KOJYENXGDXRGDK-OBWVEWQSSA-N methyl (9e,11e,13e)-octadeca-9,11,13-trienoate Chemical compound CCCC\C=C\C=C\C=C\CCCCCCCC(=O)OC KOJYENXGDXRGDK-OBWVEWQSSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- BRNPAEUKZMBRLQ-UHFFFAOYSA-N octadecyl 3,4,5-trihydroxybenzoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C1=CC(O)=C(O)C(O)=C1 BRNPAEUKZMBRLQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000005474 octanoate group Chemical group 0.000 abstract 1
- 229940055577 oleyl alcohol Drugs 0.000 abstract 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 abstract 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- 235000021317 phosphate Nutrition 0.000 abstract 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 abstract 1
- 239000000049 pigment Substances 0.000 abstract 1
- 229920002647 polyamide Polymers 0.000 abstract 1
- 229920000647 polyepoxide Polymers 0.000 abstract 1
- 239000003813 safflower oil Substances 0.000 abstract 1
- 235000005713 safflower oil Nutrition 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 239000010936 titanium Substances 0.000 abstract 1
- 229910052719 titanium Inorganic materials 0.000 abstract 1
- 229930195735 unsaturated hydrocarbon Chemical group 0.000 abstract 1
- 229910052726 zirconium Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
- C09F7/00—Chemical modification of drying oils
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/14—Esterification
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/08—Anti-corrosive paints
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Paints Or Removers (AREA)
Abstract
Polyhydroxy phenol-substituted fatty media are obtained by heating at a temperature below that at which decomposition of the reactants take place a polyhydric phenol with a fatty medium containing olefinic unsaturation and/or hydroxyl groups in the presence of a catalyst which comprises a metal alkoxide or an activated alumino silicate, at least one of the reactants containing a free or esterified carboxylic group. The fatty media referred to are esters, acids or alcohols containing straight chains of at least 6 carbon atoms containing hydroxyl groups and/or olefinic unsaturation. Suitable catalysts are, for example, an alkoxide of aluminium, titanium or zirconium or acid activated montmorillonite. Suitable temperatures are in the range 150-250 DEG C. In the examples (a) methyl gallate is reacted with octadecanol to give mainly octadecyl gallate; (b) methyl or propyl gallate is reacted with oleyl alcohol to give oleyl gallate; (c) castor oil is reacted with methyl gallate; (d) linseed oil is reacted with propyl gallate; (e) isomerized safflower oil is reacted with propyl gallate; (f) dehydrated castor oil is reacted with pyrogallol; (g) linseed oil is reacted with pyrogallol; (h) methyl undecenoate is reacted with pyrogallol; (k) methyl oleate is reacted with catechol; (k) methyl undecenoate is reacted with catechol; (l) mixed linseed methyl esters are reacted with catechol; (m) methyl-beta-eleostearate is reacted with catechol; (n) methyl oleate is reacted with pyrogallol; (o) methyl undecenoate is reacted with pyrogallol; and (p) mixed linseed methyl esters are reacted with pyrogallol.ALSO:Polyhydroxy phenol-substituted fatty media are obtained by heating at a temperature below that at which decomposition of the reactants take place a polyhydric phenol with a fatty medium containing olefinic unsaturation and/or hydroxyl groups in the presence of a catalyst which comprises a metal alkoxide or an activated aluminosilicate, at least one of the reactants containing a free or esterified carboxylic group. Suitable fatty media are, for example, alkyd resins having free hydroxy groups or unsaturated hydrocarbon groups and polyethylene sebacate. Examples are given of the reactions between (a) a linseed/tung/phthalic/glycerol alkyd and methyl gallate (Ex. 5); (b) a castor oil/phthalic/glycerol alkyd and methyl gallate (Ex. XI); (c) linseed/tung/phthalic/glycerol alkyd and propyl gallate (Ex. XII); (d) a linseed/tung/phthalic/pentaerythritol alkyd and propyl gallate (Ex. XIII); (e) a lauric/phthalic/glycerol alkyd and methyl gallate (Ex. XIV); (f) a dehydrated castor-modified bisphenol epoxy resin and propyl gallate (Ex. XXV); (g) a polyethylene sebacate and propyl gallate (Ex. XXVII); (h) propyl gallate and the product of the condensation of linoleic polyamide with a linseed/tung/phthalic glycerol alkyd (Ex. XXIX); (j) a linseed/tung/phthalic/glycerol alkyd with propyl gallate (Ex. XXII). The products are dissolved in ethylene glycol monoethyl ether, to which may also be added solvent naphtha, to give coating varnishes for steel. To these varnishes are also optionally added small amounts of acetic acid and/or iron butoxide, and/or Fe2O3 pigment (Ex. XXIII).ALSO:Polyhydroxy phenol-substituted fatty media which are prepared by reacting a polyhydric phenol with a fatty medium containing olefinic unsaturation and/or hydroxyl groups, at least one of the reactants containing a free or esterified carboxylic group, are used in coating compositions for ferrous (including steel) surfaces. The fatty media referred to are esters, acids or alcohols containing straight chains of at least 6 carbon atoms or alkyd resins containing five hydroxy groups or olefinic unsaturation. Suitable polyhydric phenols are, for example, gallic acid and its esters, pyrogallol and catechol. The resulting compounds are applied in suitable solvents, e.g. lower glycol ethers, to the ferrous surfaces. Small amounts of acidic substances, e.g. acetic acid, formic acid and acid phosphates or an iron compound, e.g. iron butoxide or octoate may be added to the solution.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US367262A US3304276A (en) | 1964-05-13 | 1964-05-13 | Polyhydric phenol modified fatty media and iron surfaces chelated therewith |
| US442831A US3321320A (en) | 1965-03-25 | 1965-03-25 | Iron butoxide improved polyhydric phenol modified alkyd compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1045118A true GB1045118A (en) | 1966-10-05 |
Family
ID=27003728
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1684765A Expired GB1045118A (en) | 1964-05-13 | 1965-04-21 | Polyhydric phenol modified fatty media and iron surfaces chelated therewith |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1045118A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4760197A (en) * | 1986-03-12 | 1988-07-26 | Imperial Chemical Industries Plc | Corrosion inhibition |
| US5162156A (en) * | 1990-09-21 | 1992-11-10 | Lord Corporation | Phenolic resin adhesion promoters and adhesive compositions, and bonding method employing same |
| CN113679039A (en) * | 2021-05-12 | 2021-11-23 | 浙江大学 | Gallic acid polyethylene glycol ester protein carrier synergist and preparation method and application thereof |
-
1965
- 1965-04-21 GB GB1684765A patent/GB1045118A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4760197A (en) * | 1986-03-12 | 1988-07-26 | Imperial Chemical Industries Plc | Corrosion inhibition |
| US5162156A (en) * | 1990-09-21 | 1992-11-10 | Lord Corporation | Phenolic resin adhesion promoters and adhesive compositions, and bonding method employing same |
| CN113679039A (en) * | 2021-05-12 | 2021-11-23 | 浙江大学 | Gallic acid polyethylene glycol ester protein carrier synergist and preparation method and application thereof |
| CN113679039B (en) * | 2021-05-12 | 2023-05-09 | 浙江大学 | Polyethylene glycol gallate protein carrier synergist and preparation method and application thereof |
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