GB823840A - Improvements in alicyclic tetracarboxylic acids and their derivatives - Google Patents
Improvements in alicyclic tetracarboxylic acids and their derivativesInfo
- Publication number
- GB823840A GB823840A GB17403/58A GB1740358A GB823840A GB 823840 A GB823840 A GB 823840A GB 17403/58 A GB17403/58 A GB 17403/58A GB 1740358 A GB1740358 A GB 1740358A GB 823840 A GB823840 A GB 823840A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- reaction
- dianhydride
- cis
- mixture
- 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
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
- C08G59/4215—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof cycloaliphatic
-
- 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
Abstract
The invention comprises 1-trans, 2-cis, 4-trans - tricarboxy - 3 - cis - carboxymethyl cyclopentane and its dianhydride. The acid may be prepared by oxidizing 5- or 6-hydroxy-5,6-dihydro-exo-dicyclopentadiene or a carboxylic acid ester thereof and the dianhydride by dehydrating the acid with any of the usual chemical dehydrating agents. The alcohol reactant may be obtained by treating dicyclopentadiene with 20-25% sulphuric acid as described in J.A.C.S. 67, 723-8 and its esters may be prepared in the conventional manner. The oxidation is preferably carried out using 30-75% aqueous nitric acid at 30-60 DEG C. in the presence of an oxidation catalyst such as Co, Ni, V or the oxides of V, Ta, Pb, Mn, Co, Cr or Mo and also in the presence of traces of sodium nitrite which tends to promote the reaction by the formation of nitrous fumes. The acid may be isolated by concentrating the reaction mixture after the exothermic reaction has ceased so that the acid crystallizes out. In the examples: (1) the alcohol is run into a mixture of 70% nitric acid, V2O5 and NaNo2 at 60 DEG C. over 12 hours, the mixture kept at 60 DEG C. a further 2 hours and the acid isolated by concentration; (2) the acid is similarly prepared at 55 DEG C. in the absence of a catalyst; (3) the acid is similarly prepared at 55-60 DEG C. from the acetate ester of the alcohol in the absence of a catalyst; (4) the dianhydride is obtained by treating the acid with 20 parts of acetyl chloride at room temperature for 3-5 weeks. The dianhydride may be used as a curing agent for epoxy resins (see Group IV (a)).ALSO:Epoxy resins are cured by mixing the resin with the di-anhydride of 1-trans-2-cis-4-transtricarboxy - 3 - cis - carboxymethylcyclopentane (see Group IV (b)) at a moderate temperature at which any reaction between the resin and the di-anhydride is slow and then heating the mixture to a temperature at which reaction occurs or at which it occurs at a substantially higher rate, whereby the cure is effected. An example is given using a resin derived from epichlorohydrin and 4,41-isopropylidene diphenol.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US685424A US3080418A (en) | 1957-09-23 | 1957-09-23 | Process for the preparation of trans, cis, trans-1, 2, 4-tricarboxy-cis-3-carboxymethylocylopentane |
Publications (1)
Publication Number | Publication Date |
---|---|
GB823840A true GB823840A (en) | 1959-11-18 |
Family
ID=24752152
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB17403/58A Expired GB823840A (en) | 1957-09-23 | 1958-05-30 | Improvements in alicyclic tetracarboxylic acids and their derivatives |
Country Status (5)
Country | Link |
---|---|
US (1) | US3080418A (en) |
DE (1) | DE1078120B (en) |
FR (1) | FR1207769A (en) |
GB (1) | GB823840A (en) |
NL (1) | NL231511A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3242206A (en) * | 1961-12-18 | 1966-03-22 | Copolymer Rubber & Chem Corp | Recycling a portion of the reaction products in an hno3 oxidation of a dicarboxy cycloalkene compound to control the oxidation rate |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1141988B (en) * | 1960-04-28 | 1963-01-03 | Grace W R & Co | Process for the preparation of 2, 3, 5-Tricarboxycyclopentylessigsaeure |
US3194816A (en) * | 1961-12-18 | 1965-07-13 | Copolymer Rubber & Chem Corp | Purification of 1, 2, 3, 4-cyclopentanetet-racarboxylic acid and preparation of its anhydride |
US9097938B2 (en) | 2010-04-23 | 2015-08-04 | Rolic Ag | Photoaligning material |
WO2013017467A1 (en) | 2011-08-02 | 2013-02-07 | Rolic Ag | Photoaligning material |
WO2013026691A1 (en) | 2011-08-25 | 2013-02-28 | Rolic Ag | Photoreactive compounds |
CN103842329B (en) | 2011-10-03 | 2016-12-07 | 罗利克有限公司 | Optical directional material |
CN103889944A (en) | 2011-10-03 | 2014-06-25 | 罗利克股份公司 | Photoaligning materials |
KR102637838B1 (en) | 2015-11-11 | 2024-02-16 | 롤릭 테크놀로지스 아게 | Photoalignment material |
JP2019531398A (en) | 2016-10-11 | 2019-10-31 | ロリク・テクノロジーズ・アーゲーRolic Technologies Ag | Photo-alignment copolymer material |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1960211A (en) * | 1932-11-03 | 1934-05-22 | Dow Chemical Co | Preparation of adipic acids |
US2615008A (en) * | 1945-09-18 | 1952-10-21 | Devoe & Raynolds Co | Epoxide resin compositions |
US2750411A (en) * | 1951-11-14 | 1956-06-12 | Gordon S Fisher | Converting alpha-pinene to mixtures of acids |
US2668807A (en) * | 1952-04-08 | 1954-02-09 | Devoe & Raynolds Co | Epoxide compositions |
US2806057A (en) * | 1953-02-24 | 1957-09-10 | Shell Dev | Hydroxy-substituted tetrahydrophthalic acids, derivatives thereof, and method for producing the same |
US2798079A (en) * | 1953-12-29 | 1957-07-02 | Universal Oil Prod Co | Condensation of aromatic hydrocarbon derivatives with carbohydrates and related materials |
US2782233A (en) * | 1955-03-11 | 1957-02-19 | Du Pont | Boric tris-(fluorocarboxylic) anhydrides |
US2798080A (en) * | 1956-05-10 | 1957-07-02 | Eastman Kodak Co | Process of manufacturing mixed anhydrides of carboxylic acids |
-
0
- NL NL231511D patent/NL231511A/xx unknown
-
1957
- 1957-09-23 US US685424A patent/US3080418A/en not_active Expired - Lifetime
-
1958
- 1958-05-30 GB GB17403/58A patent/GB823840A/en not_active Expired
- 1958-07-10 FR FR1207769D patent/FR1207769A/en not_active Expired
- 1958-09-02 DE DEP21292A patent/DE1078120B/en active Pending
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3242206A (en) * | 1961-12-18 | 1966-03-22 | Copolymer Rubber & Chem Corp | Recycling a portion of the reaction products in an hno3 oxidation of a dicarboxy cycloalkene compound to control the oxidation rate |
Also Published As
Publication number | Publication date |
---|---|
NL231511A (en) | |
DE1078120B (en) | 1960-03-24 |
US3080418A (en) | 1963-03-05 |
FR1207769A (en) | 1960-02-18 |
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