HOMOGENEOUS THERMOSETTABLE COMPOSITION OF A POLYANHYDRIDE AND A POLYEPOXIDE

• US 3,852,236 A
• Filed: 08/09/1972
• Issued: 12/03/1974
• Est. Priority Date: 12/21/1970
• Status: Expired due to Term

• Current Assignee: Chevron Research Company (Chevron Corp.)
• Original Assignee: William J. Heilman
• Inventors: Heilman, William J.
• Primary Examiner(s): Schofer, Joseph I.
• Assistant Examiner(s): Holler, A.
• Application Number:
  US05/278,967
• Time in Patent Office: 846 Days
• Field of Search: 260/878R,836,41AG,886,42.18
• US Class Current: 524/531
• CPC Class Codes: C08F 20/02 Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
• CPC Class Codes: C08F 267/04 on to polymers of anhydrides
• CPC Class Codes: C08F 8/00 Chemical modification by after-treatment graft polymers, block polymers, crosslinking with unsaturated monomers or with polymers C08F251/00 - C08F299/00; of conjugated diene rubbers C08C

Abstract

A new composition comprising a homogeneous mixture of polyanhydride, for example, the copolymer of maleic anhydride and an alpha-olefin, and a polyepoxide formed by free radical copolymerization of an olefinically unsaturated monooxirane compound such as glycidyl methacrylate and an olefin such as styrene. This composition is capable of being molded, particularly when in combination with a substrate such as fiber glass, and further cured through anhydride and epoxide groups to a solid, infusible resin.

Claims

1. A METHOD OF PREPARING A HANDLEABLE, THERMOSETTABLE, MOLDABLE COMPOSITION WHICH COMPRISES THE STEPS FORMING A LIQUID SOLUTION CONSISTING ESSENTIALLY OF A POLYANHYDRIDE REPRESENTED BY THE GENERAL FORMULA FIG-01 WHEREIN N IS BETWEEN 2 AND ABOUT 500, R IS HYDROGEN, HALOGEN OR A STRAIGHT CHAIN ALKYL OR HALOGENATED ALKYL GROUP HAVING FROM 1 TO 18 CARBON ATOMS, R1 AND R2 ARE INDEPENDENTLY SELECTED FROM HYDROGEN, HALOGEN, ALKYL HAVING FROM ONE TO FOUR CARBON ATOMS AND PHENYL, R3 IS HYDROGEN, CHLORINE, BROMINE OR METHYL AND R4 AND R5 ARE ON AN AROMATIC NUCLEUS AND ARE INDEPENDENTLY SELECTED FROM HYDROGEN, CHLORINE, BROMINE, LOWER ALKYL HAVING FROM ONE TO FOUR CARBON ATOMS, METHOXY AND ETHOXY;

AN OLEFINICALLY UNSATURATED MONOXIRANE COMPOUND CONTAINING AS ITS ONLY FUNCTIONAL GROUPS A SINGLE OXIRANE OXYGEN ATOM AND AN OLEFINIC DOUBLE BOND CAPABLE OF BEING POLYMERIZED BY FREE RADICAL MEANS;

AND OPTIONALLY AN OLEFINICALLY UNSATURATED MONOMER FREE OF OXIRANE OXYGEN ATOMS AND CONTAINING AS ITS ONLY FUNCTIONAL GROUPS AT LEAST ONE OLEFINIC DOUBLE BOND CAPABLE OF POLYMERIZATION BY FREE RADICAL MEANS;

AND POLYMERIZING AT LEAST A PORTION OF SAID OLEFINIC DOUBLE BONDS OF SAID OLEFINICALLY UNSATURATED MONOOXIRANE COMPOUND AND SAID OLEFINICALLY UNSATURATED MONOMER BY USING A CHEMICAL FREE RADICAL INITIATOR AT A TEMPERATURE UP TO ABOUT 70*C. WITHOUT SUBSTANTIAL POLYMERIZATION OF THE ANHYDRIDE GROUPS AND THE EPOXIDE GROUPS PRESENT IN THE MIXTURE WHEREBY A HANDLEABLE, THERMOSETTABLE, MOLDABLE COMPOSITION COMPRISING A HOMOGENOUS MIXTURE OF POLYANHYDRIDE MOLECULES, POLYEPOXIDE MOLECULES AND ANY UNREACTED OLEFINICALLY UNSATURATED MONOOXIRANE COMPOUND AND OLEFINICALLY UNSATURATED MONOMER IS OBTAINED.

2. A method in accordance with claim 1 In which the chemical free radical initiator is an organic peroxide.

3. A method in accordance with claim 1 in which a fiber glass substrate is incorporated into said liquid solution.

4. A method in accordance with claim 1 in which the polyanhydride is represented by the general formula:

5. A method in accordance with claim 4 in which R1 and R2 are hydrogen, the olefinically unsaturated monooxirane compound is glycidyl acrylate or glycidyl methacrylate and the olefinically unsaturated monomer is styrene.

6. A method in accordance with claim 1 in which the polyanhydride is represented by the general formula:

7. A method in accordance with claim 6 in which R1R2, R3, R4and R5 are hydrogen, the olefinically unsaturated monooxirane compound is glycidyl acrylate or glycidyl methacrylate and the olefinically unsaturated monomer is styrene.

8. A method in accordance with claim 1 at a temperature up to about 50* C.

9. A method in accordance with claim 1 in which a plasticizer is present in said solution.

10. A method in accordance with claim 1 in which the anhydride to epoxide equivalent ratio is between about 0.1:

1 and about 5;

1 and the amount of olefinically unsaturated monomer is between about 0 and about 4 parts by weight per part of the olefinically unsaturated monooxirane compound.

11. A method in accordance with claim 10 in which the anhydride to epoxide equivalent ratio is between about 0.5:

1 and about 1.5;

1 and the amount of olefinically unsaturated monomer is between about 0.25 and about 2 parts by weight per part of the olefinically unsaturated monooxirane compound.

12. A method in accordance with claim 3 in which the handleable, thermosettable, moldable composition is formed in a relatively thin sheet.