GB906017A - Substituted tetrahydro- and hexahydrophthalic anhydrides and resinous compositions containing the same - Google Patents

Substituted tetrahydro- and hexahydrophthalic anhydrides and resinous compositions containing the same

Info

Publication number
GB906017A
GB906017A GB3429159A GB3429159A GB906017A GB 906017 A GB906017 A GB 906017A GB 3429159 A GB3429159 A GB 3429159A GB 3429159 A GB3429159 A GB 3429159A GB 906017 A GB906017 A GB 906017A
Authority
GB
United Kingdom
Prior art keywords
anhydride
dimethyl
anhydrides
hexahydrophthalic
product
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
GB3429159A
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.)
Heyden Newport Chemical Corp
Original Assignee
Heyden Newport Chemical Corp
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 Heyden Newport Chemical Corp filed Critical Heyden Newport Chemical Corp
Publication of GB906017A publication Critical patent/GB906017A/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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Epoxy Resins (AREA)

Abstract

A resinous composition comprises a polyepoxide resin having a 1,2-epoxy-equivalency of at least 1,1 and a curing agent therefor comprising a dialkyl alkenyl tetrahydrophthalic anhydride or a trialkyl hexahydrophthalic anhydride or a mixture thereof said curing agent being present in an amount such that from 0,8 to 1,2 equivalents of anhydride are present for each equivalent of epoxide in the polyepoxide resin. The polyepoxides employed may be saturated or unsaturated cycloaliphatic, aromatic or heterocyclic and may be substituted with chlorine atoms, hydroxy or amino groups or both hydroxy and amino groups. Preferred curing agents are dimethyl butenyl tetrahydrophthalic anhydrides and dimethyl butyl hexahydrophthalic anhydrides, the term "butenyl" including all alkenyl radicals of the formula C4H7 and the term "butyl" all alkyl groups of the formula C4H9, and are preferably prepared from allo-ocimene and maleic anhydride (see Group IV(b)). Examples are furnished wherein the curing of epoxy resins in the presence of the anhydrides specified above and N,N-dimethyl-benzyl amine is described. In a comparative example phthalic anhydride is used as the curing agent. Optional additives specified are solvents (acetone, ethyl acetate and chloroform), and resins (alkyd, urea or phenolics).ALSO:Acid anhydrides are obtained by reacting allo-ocimene and maleic anhydride and optionally hydrogenating the product. The product of the Diels-Alder reaction is believed to consist of a mixture of 3,4-dimethyl-6-isobutenyl-tetrahydrophthalic anhydride and 3,3-dimethyl-6-sec. butenyl-tetrahydrophthalic anhydride and the hydrogenation product, of a mixture of 3,4-dimethyl-6-isobutyl-hexahydrophthalic anhydride and 3,3-dimethyl-6-sec. butyl hexahydrophthalic anhydride. The allo-ocimene-maleic anhydride reaction product may be isomerised by heating to obtain products liquid at ordinary temperature. The hydrogenation may be carried out at elevated temperature and pressure in the presence of Raney nickel. Examples are furnished. The products are used as curing agents for polyepoxide resins (see Group IV(a)).
GB3429159A 1958-10-09 1959-10-09 Substituted tetrahydro- and hexahydrophthalic anhydrides and resinous compositions containing the same Expired GB906017A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US76618958A 1958-10-09 1958-10-09

Publications (1)

Publication Number Publication Date
GB906017A true GB906017A (en) 1962-09-19

Family

ID=25075670

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3429159A Expired GB906017A (en) 1958-10-09 1959-10-09 Substituted tetrahydro- and hexahydrophthalic anhydrides and resinous compositions containing the same

Country Status (3)

Country Link
DE (1) DE1129691B (en)
FR (1) FR1243547A (en)
GB (1) GB906017A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1980001804A1 (en) * 1979-02-28 1980-09-04 Mitsubishi Petrochemical Co Liquefaction of acid anhydride
US4332733A (en) 1979-02-28 1982-06-01 Mitsubishi Petrochemical Co., Ltd. Process for liquefying acid anhydride
WO1998033787A1 (en) * 1997-01-30 1998-08-06 Shell Internationale Research Maatschappij B.V. Process for the preparation of a carboxylic anhydride

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE632074A (en) * 1962-05-11

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE531450A (en) * 1953-08-28

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1980001804A1 (en) * 1979-02-28 1980-09-04 Mitsubishi Petrochemical Co Liquefaction of acid anhydride
US4332733A (en) 1979-02-28 1982-06-01 Mitsubishi Petrochemical Co., Ltd. Process for liquefying acid anhydride
WO1998033787A1 (en) * 1997-01-30 1998-08-06 Shell Internationale Research Maatschappij B.V. Process for the preparation of a carboxylic anhydride
AU726989B2 (en) * 1997-01-30 2000-11-30 Shell Internationale Research Maatschappij B.V. Process for the preparation of a carboxylic anhydride

Also Published As

Publication number Publication date
FR1243547A (en) 1960-10-14
DE1129691B (en) 1962-05-17

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