US4092294A — Method for preparing polyphenylene ethers

Claim 1

Independent Claim 208 words

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 1 is independently isopropyl, a C 4-8 tertiary alkyl or a cycloalkyl group having no hydrogens on the alphacarbon atom and R 2 is C 2-4 alkylene or C 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.

Claim 2

Dependent Claim 208 words

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 1 is independently isopropyl, a C 4-8 tertiary alkyl or a cycloalkyl group having no hydrogens on the alphacarbon atom and R 2 is C 2-4 alkylene or C 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.

Claim 3

Dependent Claim 39 words

A process as defined in claim 1 wherein the secondary amine is selected from compounds of the formula: ##STR8## wherein R and R' are independently selected from the group consisting of lower alkyl of 3 to 6 carbon atoms.

Claim 4

Dependent Claim 72 words

A process as defined in claim 1 wherein said polyphenylene ether is of the formula: ##STR9## wherein Q is a hydrocarbon radical, a halogen radical having at least two carbon atoms between the carbon atom and the phenyl nucleus, and Q' and Q" are the same as Q and in addition, halogen, provided that Q, Q' and Q" are all free of a tertiary carbon atom and n is at least 50.

Claim 5

Dependent Claim 26 words

A process is defined in claim 1 wherein Q and Q' are hydrocarbon radicals having from 1 to 8 carbon atoms and Q" are each hydrogen.

Claim 6

Dependent Claim 15 words

A process as defined in claim 4 wherein Q and Q' are each methyl radicals.

Claim 7

Dependent Claim 14 words

A process as defined in claim 1 wherein the copper compound is cuprous bromide.

Claim 8

Dependent Claim 13 words

A process as defined in claim 1 wherein said tertiary amine is n-butyldimethylamine.

Claim 9

Dependent Claim 12 words

A process as defined in claim 2 wherein said 4-bromophenol is 4-bromoxylenol.

Claim 10

Dependent Claim 184 words

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.

Claim 11

Dependent Claim 184 words

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.

Claim 12

Dependent Claim 13 words

A process as defined in claim 9 wherein said phenolic compound is 2,6-xylenol.

Claim 13

Dependent Claim 21 words

A process as defined in claim 10 wherein the poly (2,6-dimethyl-1,4-phenylene ether) resin has a polymerization degree of at least 50.

Claim 14

Dependent Claim 14 words

A process as defined in claim 11 wherein the secondary amine is di-n-butyl amine.

Claim 15

Dependent Claim 14 words

A process as defined in claim 11 wherein the secondary amine is di-isobutyl amine.

Claim 16

Dependent Claim 13 words

A process as defined in claim 11 wherein the secondary amine is di-n-propylamine.

Claim 17

Dependent Claim 120 words

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.

Claim 18

Dependent Claim 120 words

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.

Claim 19

Dependent Claim 13 words

A process as defined in claim 15 wherein said phenolic compound is 2,6-xylenol.

Claim 20

Dependent Claim 21 words

A process as defined in claim 15 wherein the poly (2,6-dimethyl-1,4-phenylene ether) resin has a polymerization degree of at least 50.

Claim 21

Dependent Claim 14 words

A process as defined in claim 17 wherein the secondary amine is di-n-butyl amine.

Claim 22

Dependent Claim 14 words

A process as defined in claim 17 wherein the secondary amine is di-isobutyl amine.

Claim 23

Dependent Claim 13 words

A process as defined in claim 17 wherein the secondary amine is di-n-propylamine.

Annuity Stage	Window Opens	Payment Deadline	Surcharge Period Until	Estimated Fee	Status
3.5 Years (Year 4)	1981-05-29	1981-11-28	1982-05-30	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	1985-05-29	1985-11-28	1986-05-30	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	1989-05-29	1989-11-28	1990-05-30	$7700.00	Window Closed / Lapsed

Method for preparing polyphenylene ethers

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