Copolymer of a bisphenol diglycidyl ether and a phenolphthalene and/or a phenolphthalimidine, method for the preparation thereof, article comprising the copolymer, and compositions comprising the copolymer

Patent metadata

Field	Value
Publication number	US-9951217-B2
Application number	US-201414168323-A
Country	US
Kind code	B2
Filing date	Jan 30, 2014
Priority date	Jan 30, 2014
Publication date	Apr 24, 2018
Grant date	Apr 24, 2018

Abstract

A copolymer exhibiting improved heat resistance relative to phenolic resins is formed by the reaction of a bisphenol diglycidyl ether and a phenolphthalein and/or a phenolphthalimidine in a molar ratio of 0.98:1 to 1.02:1 in the presence of a catalyst. The copolymer can be used to mold plastic parts. The copolymer is also useful as a flexibilizer in thermoset compositions, and useful as a compatibilizer in blends of polar and non-polar polymers, and blends of non-polar polymers and polar fillers.

First claim

The invention claimed is:

1. A method of forming a copolymer, the method comprising:
adding
an oligomeric bisphenol diglycidyl ether to
an N-phenylphenolphthalimidine wherein the phenyl group bound to nitrogen is unsubstituted or substituted
in a molar ratio of 0.98:1 to 1.02:1 in the presence of a tertiary amine catalyst to form a reaction mixture; and
reacting
the oligomeric bisphenol diglycidyl ether and
the N-phenylphenolphthalimidine
to form a copolymer;
wherein the oligomeric bisphenol diglycidyl ether is added to the N-phenylphenolphthalimidine such that an excess of phenolic groups relative to epoxy groups is maintained in the reaction mixture.

2. The method of claim 1 , wherein the oligomeric bisphenol diglycidyl ether has the structure

wherein m is, on average, 1.2 to 10; each occurrence of w is independently 0 or 1; each occurrence of x is independently 0, 1, 2, 3, or 4; each occurrence of R 1 is independently halogen, C 1 -C 12 hydrocarbylthio, C 1 -C 12 hydrocarbyloxy, C 2 -C 12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms, or unsubstituted or substituted C 1 -C 12 hydrocarbyl; and each occurrence of Y is independently

wherein each occurrence of R 4 , R 5 , R 6 , and IC is independently hydrogen or an unsubstituted or substituted C 1 -C 12 hydrocarbyl; and
the N-phenylphenolphthalimidine has the structure

wherein each occurrence of y is independently 0, 1, 2, 3, or 4; and each occurrence of R 2 is independently halogen, C 1 -C 12 hydrocarbylthio, C 1 -C 12 hydrocarbyloxy, C 2 -C 12 halohydrocarbolyoxy wherein at least two carbon atoms separate the halogen and oxygen atoms, or unsubstituted or substituted C 1 -C 12 hydrocarbyl; and R 3 is independently unsubstituted or substituted phenyl.

3. The method of claim 1 , wherein the tertiary amine catalyst comprises triethylamine, tri-n-propylamine, tri-n-butylamine, dimethylaniline, diethylaniline, alpha-methylbenzyldimethylamine, N,N-dimethylaminoethanol, N,N-dimethylaminopyridine, alkylimidazoles, or a combination thereof.

4. The method of claim 1 , wherein the copolymer has a weight average molecular weight of 10,000 to 100,000 atomic mass units.

5. The method of claim 1 ,
wherein said reacting comprises reacting the oligomeric bisphenol diglycidyl ether and the N-phenylphenolphthalimidine in a molar ratio of 0.99:1 to 1.01:1;
wherein the oligomeric bisphenol diglycidyl ether has the structure

wherein m is, on average, 1.5 to 7;
wherein the N-phenylphenolphthalimidine has the structure

and
wherein the copolymer has a weight average molecular weight of 20,000-40,000 atomic mass units.

Assignees

• Sabic Innovative Plastics Ip Bv
• Sabic Global Technologies Bv

Inventors

• Peters Edward Norman

Classifications

• C08L77/06

  Polyamides derived from polyamines and polycarboxylic acids (C08L77/10 takes precedence) · CPC title

• C08G65/2633

  the other compounds containing amide groups · CPC title

• C08L75/04

  Polyurethanes · CPC title

• C08G2650/56

  Polyhydroxyethers, e.g. phenoxy resins · CPC title

• C08L71/00

  Compositions of polyethers obtained by reactions forming an ether link in the main chain (of polyacetals C08L59/00; of epoxy resins C08L63/00; of polythioether-ethers C08L81/02; of polyether-sulfones C08L81/06); Compositions of derivatives of such polymers · CPC title