GB823840A - Improvements in alicyclic tetracarboxylic acids and their derivatives - Google Patents

Improvements in alicyclic tetracarboxylic acids and their derivatives

Info

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
Application number
GB17403/58A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of GB823840A publication Critical patent/GB823840A/en
Expired legal-status Critical Current

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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

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.
GB17403/58A 1957-09-23 1958-05-30 Improvements in alicyclic tetracarboxylic acids and their derivatives Expired GB823840A (en)

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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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
JP5856147B2 (en) 2010-04-23 2016-02-09 ロリク アーゲーＲｏｌｉｃ Ａｇ Photo-alignment material
KR102020755B1 (en) 2011-08-02 2019-09-11 롤리크 아게 Photoaligning material
CN103748192B (en) 2011-08-25 2016-07-27 罗利克有限公司 Photoreactive compound
KR101998557B1 (en) 2011-10-03 2019-07-10 롤리크 아게 Photoaligning materials
BR112014007924A2 (en) 2011-10-03 2017-04-11 Rolic Ag alignment photo materials
WO2017081056A1 (en) 2015-11-11 2017-05-18 Rolic Ag Photoalignment materials
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)

* Cited by examiner, † Cited by third party
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

Cited By (1)

* Cited by examiner, † Cited by third party
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
FR1207769A (en) 1960-02-18
US3080418A (en) 1963-03-05
NL231511A (en)
DE1078120B (en) 1960-03-24

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