GB882147A - Novel aliphatic carboxylic acid esters - Google Patents
Novel aliphatic carboxylic acid estersInfo
- Publication number
- GB882147A GB882147A GB4351759A GB4351759A GB882147A GB 882147 A GB882147 A GB 882147A GB 4351759 A GB4351759 A GB 4351759A GB 4351759 A GB4351759 A GB 4351759A GB 882147 A GB882147 A GB 882147A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- polycyclopentadiene
- acids
- esters
- epoxidized
- 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
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 title abstract 6
- 239000002253 acid Substances 0.000 abstract 9
- 150000002148 esters Chemical class 0.000 abstract 9
- 150000001875 compounds Chemical class 0.000 abstract 7
- 239000004593 Epoxy Chemical group 0.000 abstract 5
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical group C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 abstract 5
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 abstract 4
- 150000007513 acids Chemical class 0.000 abstract 4
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 4
- 229930195729 fatty acid Natural products 0.000 abstract 4
- 239000000194 fatty acid Substances 0.000 abstract 4
- 150000004665 fatty acids Chemical class 0.000 abstract 4
- 150000004670 unsaturated fatty acids Chemical class 0.000 abstract 4
- 235000021122 unsaturated fatty acids Nutrition 0.000 abstract 4
- 238000001035 drying Methods 0.000 abstract 3
- 125000003700 epoxy group Chemical group 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- 229920005989 resin Polymers 0.000 abstract 3
- 239000011347 resin Substances 0.000 abstract 3
- 229920006395 saturated elastomer Polymers 0.000 abstract 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 2
- 229910000831 Steel Inorganic materials 0.000 abstract 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- -1 amine aldehyde Chemical class 0.000 abstract 2
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 239000011521 glass Substances 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract 2
- 239000011976 maleic acid Substances 0.000 abstract 2
- 239000003921 oil Substances 0.000 abstract 2
- 235000003441 saturated fatty acids Nutrition 0.000 abstract 2
- 150000004671 saturated fatty acids Chemical class 0.000 abstract 2
- 239000010959 steel Substances 0.000 abstract 2
- 239000011135 tin Substances 0.000 abstract 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 abstract 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 abstract 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 abstract 1
- 235000010469 Glycine max Nutrition 0.000 abstract 1
- 244000068988 Glycine max Species 0.000 abstract 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 abstract 1
- 229920000877 Melamine resin Polymers 0.000 abstract 1
- 239000005642 Oleic acid Substances 0.000 abstract 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 235000021355 Stearic acid Nutrition 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 229920000180 alkyd Polymers 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 239000004359 castor oil Substances 0.000 abstract 1
- 235000019438 castor oil Nutrition 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000008199 coating composition Substances 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 229910017052 cobalt Inorganic materials 0.000 abstract 1
- 239000010941 cobalt Substances 0.000 abstract 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- UKRVECBFDMVBPU-UHFFFAOYSA-N ethyl 3-oxoheptanoate Chemical compound CCCCC(=O)CC(=O)OCC UKRVECBFDMVBPU-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
- 238000011065 in-situ storage Methods 0.000 abstract 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 abstract 1
- GIWKOZXJDKMGQC-UHFFFAOYSA-L lead(2+);naphthalene-2-carboxylate Chemical class [Pb+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 GIWKOZXJDKMGQC-UHFFFAOYSA-L 0.000 abstract 1
- 229910052748 manganese Inorganic materials 0.000 abstract 1
- 239000011572 manganese Substances 0.000 abstract 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 abstract 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 abstract 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 abstract 1
- 150000004965 peroxy acids Chemical class 0.000 abstract 1
- 239000000049 pigment Substances 0.000 abstract 1
- 239000004014 plasticizer Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000008117 stearic acid Substances 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
- 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
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/027—Polycondensates containing more than one epoxy group per molecule obtained by epoxidation of unsaturated precursor, e.g. polymer or monomer
-
- 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
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
- C08G59/1455—Monocarboxylic acids, anhydrides, halides, or low-molecular-weight esters thereof
-
- 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
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
- C08G59/1455—Monocarboxylic acids, anhydrides, halides, or low-molecular-weight esters thereof
- C08G59/1461—Unsaturated monoacids
- C08G59/1472—Fatty acids
-
- 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
- C08G59/20—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 epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
-
- 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
- C09F7/10—Chemical modification of drying oils by re-esterification
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Emergency Medicine (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Epoxy Resins (AREA)
- Epoxy Compounds (AREA)
Abstract
Coating compositions comprise an ester of an epoxidized polycyclopentadiene or epoxided alkylcyclopentadiene having 3 to 6 cyclopentadiene units and an average of 1 to 2 epoxy groups in the molecule with a saturated or unsaturated mono- or poly-aliphatic carboxylic acid (see Groups IV(a) and IV(b)). In examples: glass, tin and steel sheet are coated with compositions containing such esters derived from stearic acid, oleic acid or blends of polymerized C18 unsaturated fatty acid with dehydrated castor oil acid together with a melamine-formaldehyde resin and, in some cases, manganese octoate, air dried and baked. In another example glass, tin and steel sheets are coated with a solution of an ester of an epoxidized cyclopentadiene with a blend of polymerized C18 unsaturated fatty acids and soya fatty acids containing cobalt, manganese and lead naphthenates and air dried.ALSO:The invention comprises esters of epoxidized polycyclopentadienes or epoxidized alkyl substituted polycyclopentadienes and aliphatic carboxylic acids, said polycyclopentadiene having 3 to 6 cyclopentadiene units and an epoxy functionality of 2 to 4 (i.e. containing an average of 1 to 2 epoxy groups in the molecule). The esters are prepared by reacting the epoxidized polycyclopentadiene and the acid at elevated temperatures. Generally 1 to 7 parts by weight of acid are used per part of epoxy compound. An inert atmosphere may be used and a catalyst such as LiOH, trimethylbenzylammonium hydroxide or (CH3)3NHOH may be present. Suitable aliphatic carboxylic acids include saturated and unsaturated fatty acids, preferably having 4 to 24 carbon atoms and polycarboxylic acids such as maleic acid or polymerized fatty acids. Part of the epoxidized polycyclopentadiene may be replaced by polyhydroxy compounds or by other polyepoxy compounds reactive with the acids. The products may contain free hydroxy groups. Esters with drying oil fatty acids harden on exposure to air to hard, tough, alkali-resistant coatings. The present esters may be blended with resins such as phenol or amine aldehyde resins, alkyd resins or resin gums, or with drying or semi-drying oils. Plasticizers, pigments and dyes may be present.ALSO:The invention comprises esters of epoxidised polycyclopentadienes or epoxidised alkyl substituted polycyclopentadienes and aliphatic carboxylic acids, said polycyclopentadiene having 3 to 6 cyclopentadiene units and an epoxy functionality of 2 to 4 (i.e. containing an average of 1 to 2 epoxy groups in the molecule). The esters are prepared by reacting the epoxidised polycyclopentadiene and the acid at elevated temperatures. Generally 1 to 7 parts by weight of acid are used per part of epoxy compound. An inert atmosphere may be used and a catalyst such as LiOH, trimethylbenzylammonium hydroxide or (CH3)3 NHOH may be present. Suitable aliphatic carboxylic acids include saturated and unsaturated fatty acids, preferably having 4 to 24 carbon atoms and polycarboxylic acids such as maleic acid or polymerised fatty acids. Part of the epoxidised polycyclopentadiene may be replaced by polyhydroxy compounds or by other polyepoxy compounds reactive with the acids. The products may contain free hydroxy groups. The epoxy compounds are prepared by reacting the polycyclopentadiene with an epoxidising agent, preferably a lower aliphatic peracid. The peracid may be preformed or formed in situ from hydrogen peroxide and the corresponding carboxylic acid. A solvent may be present.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH93060A CH386115A (en) | 1960-01-28 | 1960-01-28 | Process for the preparation of synthetic esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB882147A true GB882147A (en) | 1961-11-15 |
Family
ID=4198468
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4351759A Expired GB882147A (en) | 1960-01-28 | 1959-12-22 | Novel aliphatic carboxylic acid esters |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE586216A (en) |
| CH (1) | CH386115A (en) |
| GB (1) | GB882147A (en) |
| LU (1) | LU38110A1 (en) |
| NL (2) | NL109696C (en) |
-
0
- LU LU38110D patent/LU38110A1/xx unknown
- NL NL247910D patent/NL247910A/xx unknown
- NL NL109696D patent/NL109696C/xx active
- BE BE586216D patent/BE586216A/xx unknown
-
1959
- 1959-12-22 GB GB4351759A patent/GB882147A/en not_active Expired
-
1960
- 1960-01-28 CH CH93060A patent/CH386115A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH386115A (en) | 1964-12-31 |
| BE586216A (en) | |
| NL247910A (en) | |
| NL109696C (en) | |
| LU38110A1 (en) |
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