Method for preparing polyphenylene ethers
AssigneeGeneral Electric Company
InventorsJames Gordy Bennett, Jr., Glenn Dale Cooper
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Abstract
A novel process is disclosed for the preparation of polyphenylene ethers by an oxidative coupling reaction. The process comprises oxidatively coupling a phenolic compound in the presence of a catalyst which comprises a copper complex of a copper compound with an N,N.sup.1 -disubstituted alkylene or cycloalkylene diamine having from 2 to 3 carbon atoms between the nitrogen atoms and whose substituents on the two nitrogens atoms are isopropyl or alpha tertiary alkyl, a tertiary amine, a secondary mono-amine and a bromine containing compound.
Claims20
In a process for forming a polyphenylene ether resin by the oxidative coupling of a 2,6-disubstituted phenolic compound in the presence of a catalyst which comprises a copper compound, a diamine of the formula:
- R.sup.1 HN--R.sup.2 --NHR.sup.1
- wherein each R.sup.1 is independently isopropyl, a C.sub.4-8 tertiary alkyl or a cycloalkyl group having no hydrogens on the alphacarbon atom and R.sup.2 is C.sub.2-4 alkylene or C.sub.3-7 cycloalkylene;
- a tertiary amine;
- a bromine containing compound selected from the group consisting of hydrogen bromide, alkali metal bromides, alkaline earth metal bromides, 4-bromophenols and mixtures thereof in the presence of an oxygen containing gas, the improvement which comprises adding to the polymerization reaction an amount of a secondary mono-amine of the formula:
- ##STR7## wherein R and R' are independently selected from the group consisting of lower alkyl of from 1 to 12 carbon atoms;
- said amount being sufficient to modify the reaction so that a polyphenylene ether resin will be obtained that when combined with a styrene resin will form a composition having impact that are improved over compositions of a polyphenylene ether resin and a styrene resin wherein the polyphenylene ether resin is prepared by identical catalyst system except for the absence of a secondary mono-amine.
In a process for forming a polyphenylene ether by the oxidative coupling of a 2,6-di-substituted phenolic compound in the presence of a catalyst which comprises a copper compound, N,N'-di-tertbutylethylenediamine with low steric requirements, a 4-bromoxylenol, said process comprising passing oxygen through a solution of a 2,6-di-substituted phenol and said catalyst, the improvement which comprises adding to said catalyst a minor amount of a secondary amine selected from compounds of the formula:
- ##STR10## wherein R and R' are independently selected from the group consisting of a lower alkyl of from 3 to 6 carbon atoms, said amount being sufficient to modify the reaction so that a polyphenylene ether resin will be obtained that when combined with a styrene resin will form a composition having impact properties that are improved over compositions of a polyphenylene ether resin and a styrene resin wherein the polyphenylene ether resin is prepared by identical catalyst system except for the absence of a secondary mono-amine, to produce a mixture of a complex catalyst and a polyphenylene ether resin, and therefore separating a polyphenylene ether from said mixture by precipitation with methanol.
In a process for forming a polyphenylene ether by the oxidative coupling of a 2,6-di-substituted phenolic compound in the presence of a catalyst which comprises a copper compound, N, N'-di-tert-butylethylene-diamine, a tertiary amine with low steric requirements and hydrobromic acid, said process comprising passing oxygen through a solution of a 2,6-di-substituted phenol and said catalyst, the improvement which comprises adding to said catalyst a minor amount of a secondary amine selected from compounds of the formula:
- ##STR11## wherein R and R' are independently selected from the group consisting of lower alkyl of from 3 to 6 carbon atoms, to produce a mixture of a complex catalyst and a polyphenylene ether resin, and thereafter separating the polyphenylene ether from said mixture.
Dependencies are inferred from the claim text.