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EP0106023A2
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EP
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End-capped polyarylene polyethers, articles made therefrom and process for preparing such polyarylene polyethers
Assignee: BP Corp North America Inc
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Filing: 1983-06-29
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Granted: —
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Expires: 2003-06-29
Abstract
Abstract Class of high performance thermosetting materials composed of polyarylene polyether resins having each of their ends capped with a monovalent unsaturated organo radical. The end-capped polyarylene polyether resins have the formula: wherein Z and Z' are each a monovalent unsaturated organo radical. Usually Z and Z' are alkylene, aralkylene or cycloalkylene moieties. The end-capped polyarylene polyethers can be cured as is or in the presence of one or more unsaturated comonomers to afford homopolymers or copolymers, respectively. Such cured systems exhibit high glass transition temperatures, good tensile properties, excellent electric and alkali resistance and improved stress cracking resistance. End- terminated polysulfone resins having molecular weight of 5,00 to 15.000 are especially advantageous. The properties exhibited by the vinyl/allyl terminated oligomers are useful in fields which require high temperature performance, excellent solvent resistance and good fabrication characteristics. Specific areas of application include high performance molded products for appliances and electronics, high temperature laminates and adhesives and protective and insulative coatings.
Inventors
- 👤 You-Ling Fan
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-09 08:25
CPC Classifications
C; C08; C08G; C08G65/00; C08G65/34; C08G65/48; C08F; C08F290/00; C08F290/02; C08F290/06; C08G65/38; C08G65/40; C08G65/4012; C08G75/00; C08G75/20; C08G75/23; C08G2650/00; C08G2650/02; C08G2650/04; C08G2650/20; C08L; C08L2312/00
Claims Analysis
Total Claims: 66
Claim 1
Independent Claim
32 words
An end-capped polyarylene polyether having the formula: Z (̵ polyarylene polyether chain Z' wherein Z and Z' are each a monovalent unsaturated organo moiety, the polyarylene polyether chain being substituted or unsubstituted.
Claim 2
Dependent Claim
32 words
An end-capped polyarylene polyether having the formula: Z (̵ polyarylene polyether chain Z' wherein Z and Z' are each a monovalent unsaturated organo moiety, the polyarylene polyether chain being substituted or unsubstituted.
Claim 3
Dependent Claim
21 words
The end-capped polyarylene polyether as claimed in Claim 1 wherein the polyarylene polyether is composed of recurring units having the formula:
Claim 4
Dependent Claim
23 words
The end-capped polyarylene polyether as claimed in Claim 1 or 2 wherein Z and Z' are each an alkylene, aralkylene or cycloalkylene moiety.
Claim 5
Dependent Claim
106 words
The end-capped polyarylene polyether as claimed in Claim 1 or 2 wherein Z and Z each is a monovalent unsaturated organo moiety selected from the group consisting of: wherein R 1 , R 2 and R 3 each is hydrogen, an aliphatic hydrocarbon radical containing 1 to 20 carbon atoms, an alicyclic hydrocarbon radical containing 1 to 20 carbon atoms or an aromatic radical, and R 4 , R 5 and R 6 each is a divalent alkylene radical having 1 to 20 carbon atoms, a divalent arylene radical having 6 to 10 carbon atoms and a divalent cycloalkylene radical containing 3 to 8 carbon atoms.
Claim 6
Dependent Claim
52 words
The end-capped polyarylene polyether as claimed in Claim 4 wherein R 1 , R 2 and R 3 each is hydrogen, an alkyl radica having 1 to 20 carbon atoms, an aryl radical, an aralkyl radical, an alkaryl radical, an alicyclic radical having 3 to 8 carbon atoms or a bicyclic radical.
Claim 7
Dependent Claim
32 words
The end-capped polyarylene polyether as claimed in Claim 4 or 5 wherein R 4 , R 5 and R 6 each is a divalent alkylene radical having 1 to 8 carbon atoms.
Claim 8
Dependent Claim
75 words
An end-capped polyarylene polyether having the formula: wherein n is a positive number, Z and Z' are each amonovalent unsaturated organo moiety, E is the residue after removal of the hydroxyl groups of a dihydric phenol and E' is the residue after removal of the two activated halo groups of an aromatic compound having two activated halo substituents, with the residues represented by E and E' being unsubstituted or substituted beyond the already defined degree.
Claim 9
Dependent Claim
75 words
An end-capped polyarylene polyether having the formula: wherein n is a positive number, Z and Z' are each amonovalent unsaturated organo moiety, E is the residue after removal of the hydroxyl groups of a dihydric phenol and E' is the residue after removal of the two activated halo groups of an aromatic compound having two activated halo substituents, with the residues represented by E and E' being unsubstituted or substituted beyond the already defined degree.
Claim 10
Dependent Claim
15 words
The end-capped polyarylene polyether as claimed in Claim 7 wherein n is 2 to 300.
Claim 11
Dependent Claim
23 words
The end-capped polyarylene polyether as claimed in Claim 7 or 8 wherein Z and Z' are each an alkylene, aralkylene or cycloalkylene moiety.
Claim 12
Dependent Claim
38 words
The end-capped polyarylene polyether as claims in any of Claims 6 to 9 wherein E' is the residue of hydroquinone, 2,2-bis (4-hydroxyphenyl)propane, 4,4'-thiodiphenyl, p,p-biphenol, or bis(4-hydroxyphenyl)sulfone, and wherein E is the residue of 4,4'-dihalodiphenyl sulfone, 4,4'-dihalobenzophenone, or 4,4'-bis(4-halophenylsulfonyl)biphenyl.
Claim 13
Dependent Claim
75 words
An end-capped polyarylene polyether having the formula: wherein n is a positive number, Z and Z' are each a unsaturated organo moiety, and Ar is a divalent aromatic group that can be the same or different from one (̵ O - Ar )̵ group to the next, and in which each Ar group is bonded to the connecting oxy groups through aromatic carbon atoms, with the aromatic group represented by Ar being substituted or unsubstituted.
Claim 14
Dependent Claim
75 words
An end-capped polyarylene polyether having the formula: wherein n is a positive number, Z and Z' are each a unsaturated organo moiety, and Ar is a divalent aromatic group that can be the same or different from one (̵ O - Ar )̵ group to the next, and in which each Ar group is bonded to the connecting oxy groups through aromatic carbon atoms, with the aromatic group represented by Ar being substituted or unsubstituted.
Claim 15
Dependent Claim
15 words
The end-capped polyarylene polyether as claimed in Claim 11 wherein n is 2 to 300.
Claim 16
Dependent Claim
23 words
The end-capped polyarylene polyether as claimed in Claim 11 or 12 wherein Z and Z are each an alkylene, aralkylene or cycloalkylene moiety.
Claim 17
Dependent Claim
88 words
An end-capped polyaryl polyether having the formula: wherein: R 1 and R 2 each are hydrogen or alkyl having from one to four carbon atoms or alkoxy having one to four carbon atoms; Ar is phenylene, naphthylene,.diphenylene, or a radical having the formula: wherein R is a bivalent aliphatic, cycloaliphatic or araliphati radical having one to eight carbon atoms, -0-, -S-, -SO-, -S0 2 - or -CO-; Z and Z' are each a monovalent unsaturated organo moiety; and n is an integer from about 3 to about 200.
Claim 18
Dependent Claim
88 words
An end-capped polyaryl polyether having the formula: wherein: R 1 and R 2 each are hydrogen or alkyl having from one to four carbon atoms or alkoxy having one to four carbon atoms; Ar is phenylene, naphthylene,.diphenylene, or a radical having the formula: wherein R is a bivalent aliphatic, cycloaliphatic or araliphati radical having one to eight carbon atoms, -0-, -S-, -SO-, -S0 2 - or -CO-; Z and Z' are each a monovalent unsaturated organo moiety; and n is an integer from about 3 to about 200.
Claim 19
Dependent Claim
21 words
The end-capped polyarylene polyether as claimed in Claim 14 wherein Z and Z' are each an alkylene, aralkylene or cycloalkylene moiety.
Claim 20
Dependent Claim
14 words
The end-capped polyaryl polyether as claimed in Claim 14 or 15 wherein Ar is
Claim 21
Dependent Claim
27 words
An article comprising a substrate and adhered thereto or coated thereon a homopolymer of an end-capped polyarylene polyether as defined in any one of the preceding claims.
Claim 22
Dependent Claim
24 words
The article as claimed in Claim 17 wherein the homopolymer contains an inorganic mineral filler, preferablyan inorganic mineral filler, especially C aC0 3 .
Claim 23
Dependent Claim
17 words
.19. The articles as claimed in Claim 17 or 18 wherein the substrate is a fibrous material.
Claim 24
Dependent Claim
26 words
The article as claimed in Claim 19 wherein the fibrous material is glass fibers and the end-capped polyarylene polyether is a sizing for the glass fibers.
Claim 25
Dependent Claim
18 words
A composite comprising thermoplastic polyarylene polyether containing, as a reinforcing filler, the sized glass fibers of Claim 20.
Claim 26
Dependent Claim
22 words
A blend of a thermoplastic polyarylene polyether and the end-capped polyarylene polyether as claimed in any of the Claims 1 to 16.
Claim 27
Dependent Claim
27 words
The blend as claimed in Claim 22 wherein the thermoplastic polyarylene polyether is the thermoplastic reaction product of an alkali metal salt of 2,2-bis(4-hydroxyphenyl)propane and 4,4'-dihalodiphenyl sulfone.
Claim 28
Dependent Claim
58 words
The process for preparing an end-capped polyarylene polyether which comprises reacting substantially equimolar amounts of an alkali metal double salt of a dihydric phenol with a dihalobenzenoid compound, and reacting the end phenoxy groups of the polyarylene polyether with a compound having the formula: XZ wherein X is a halogen and Z is a monovalent unsaturated organic radical.
Claim 29
Dependent Claim
58 words
The process for preparing an end-capped polyarylene polyether which comprises reacting substantially equimolar amounts of an alkali metal double salt of a dihydric phenol with a dihalobenzenoid compound, and reacting the end phenoxy groups of the polyarylene polyether with a compound having the formula: XZ wherein X is a halogen and Z is a monovalent unsaturated organic radical.
Claim 30
Dependent Claim
70 words
Process for preparing a polysulfone resin having unsaturated organic terminal groups comprising (a) polymeriz ing a dihydric phenol and a dihalobenzenoid sulfone preferably a dichlorobenzenoid sulfone,in the presence of an alkali metal hydroxide or alkali metal oxide or ammonium hydroxide, and (b) reacting the end phenoxy groups of polysulfone (a) with a compound having the formula: XZ wherein X is a halogen and Z is a monovalent unsaturated organic radical.
Claim 31
Dependent Claim
70 words
Process for preparing a polysulfone resin having unsaturated organic terminal groups comprising (a) polymeriz ing a dihydric phenol and a dihalobenzenoid sulfone preferably a dichlorobenzenoid sulfone,in the presence of an alkali metal hydroxide or alkali metal oxide or ammonium hydroxide, and (b) reacting the end phenoxy groups of polysulfone (a) with a compound having the formula: XZ wherein X is a halogen and Z is a monovalent unsaturated organic radical.
Claim 32
Dependent Claim
23 words
Process as claimed in Claim 24 wherein the polymerization of step (a) is conducted at an elevated temperature, preferably at 150 and 180°C.
Claim 33
Dependent Claim
41 words
Process as claimed in Claim 24 wherein a solvent is present in polymerization step (a), preferably a polar solvent or a mixture of polar solvents, especially dimethyl acetamide or a mixture of dimethyl sulfoxide and dimethyl acetamide, or an aprotic solvent.
Claim 34
Dependent Claim
21 words
Process as claimed in Claim 25 wherein an alkali metal hydroxide or oxide is used in step (a), preferably sodium hydroxide.
Claim 35
Dependent Claim
20 words
process as claimed in Claim 25 wherein Z is a reactive, unsaturated radical having an alkylene, aralkylene or cycloalkylene moiety.
Claim 36
Dependent Claim
22 words
Process as claimed in Claim 25 wherein compound XZ is allyl chloride, 2-chloroethylacrylate, 2-chloroethylmethacrylate, chloromethyldimethylvinylsilane, vinyl benzyl chloride or 2-chloroethyl vinyl ether.
Claim 37
Dependent Claim
30 words
Process as claimed, in Claim 25 wherein end-capping step (b) is conducted at a temperature which does not exceed 125°C and preferably under positive nitrogen pressure and/or under anhydrous conditions.
Claim 38
Dependent Claim
26 words
Process as claimed in Claim 25 wherein the end-capped polysulfone resin is separated from the reaction mixture, preferably by coagulation or by the melt recovery method.
Claim 39
Dependent Claim
36 words
A homopolymer of an end-capped polyarylene polyether having the formula: Z (̵ polyarylene polyether chain )̵ Z' wherein Z and Z' are each a monovalent unsaturated organo moiety, the polyarylene polyether chain being substituted or unsubstituted.
Claim 40
Dependent Claim
36 words
A homopolymer of an end-capped polyarylene polyether having the formula: Z (̵ polyarylene polyether chain )̵ Z' wherein Z and Z' are each a monovalent unsaturated organo moiety, the polyarylene polyether chain being substituted or unsubstituted.
Claim 41
Dependent Claim
33 words
The homopolymer as claimed in Claim 33 wherein the polyarylene polyether is composed of recurring units having the formula: and wherein Z and Z' are each an alkylene, aralkylene 0 or cycloalkylene moiety.
Claim 42
Dependent Claim
104 words
The homopolymer as claimed in Claim 33 or 34 wherein Z and Z' each is a monovalent unsaturated organo moiety 25 selected from the group consisting of: wherein R 1 , R 2 and R 3 each is hydrogen, an aliphatic hydrocarboi radical containing 1 to 20 'carbon atoms, an.alicyclic hydrocarbon radical containing 1 to 20 carbon atoms or an aromatic radical, and R 4 , R 5 and R 6 each is a divalent alkylene radical having 1 to 10 carbon atoms, a divalent arylene radical having 6 to 10 carbon atoms and a divalent cycloalkylene radical containing 3 to 8 carbon atoms.
Claim 43
Dependent Claim
79 words
A homopolymer of an end-capped polyarylene polyether having the formula: wherein n is 2 to 300, Z and Z' are each a monovalent unsaturated organo moiety, E is the residue after removal of the hydroxyl groups of a dihydric phenol and E' is the residue after removal of the two activated halo groups of an aromatic compound having two activated halo substituents, with the residues represented by E and E' being unsubstituted or substituted beyond the already defined degree.
Claim 44
Dependent Claim
79 words
A homopolymer of an end-capped polyarylene polyether having the formula: wherein n is 2 to 300, Z and Z' are each a monovalent unsaturated organo moiety, E is the residue after removal of the hydroxyl groups of a dihydric phenol and E' is the residue after removal of the two activated halo groups of an aromatic compound having two activated halo substituents, with the residues represented by E and E' being unsubstituted or substituted beyond the already defined degree.
Claim 45
Dependent Claim
79 words
A homopolymer of an end-capped polyarylene polyether having the formula: wherein n is 2 to 300, Z and Z' are each a monovalent unsaturated organo moiety, and Ar is a divalent aromatic group that can be the same or different from one (̵ O - Ar)̵ group to the next, and in which each Ar group is bonded to the connecting oxy groups through aromatic carbon atoms, with the aromatic group represented by Ar being substituted or unsubstituted. 1
Claim 46
Dependent Claim
79 words
A homopolymer of an end-capped polyarylene polyether having the formula: wherein n is 2 to 300, Z and Z' are each a monovalent unsaturated organo moiety, and Ar is a divalent aromatic group that can be the same or different from one (̵ O - Ar)̵ group to the next, and in which each Ar group is bonded to the connecting oxy groups through aromatic carbon atoms, with the aromatic group represented by Ar being substituted or unsubstituted. 1
Claim 47
Dependent Claim
93 words
A homopolymer of an end-capped polyaryl polyether having the formula: . wherein: R 1 and R 2 each are hydrogen or alkyl having from on to four carbon atoms or alkoxy having one to four carbon atoms; Ar is phenylene, naphthylene, diphenylene, or a radical having the formula: wherein R is a bivalent aliphatic, cycloaliphatic or araliphati radical having one to eight carbon atoms, -0-, -S-, -SO-, -S0 2 - or -CO-; Z and Z' are each a monovalent unsaturated organo moiety; and n is an integer from about 3 to about 200.
Claim 48
Dependent Claim
93 words
A homopolymer of an end-capped polyaryl polyether having the formula: . wherein: R 1 and R 2 each are hydrogen or alkyl having from on to four carbon atoms or alkoxy having one to four carbon atoms; Ar is phenylene, naphthylene, diphenylene, or a radical having the formula: wherein R is a bivalent aliphatic, cycloaliphatic or araliphati radical having one to eight carbon atoms, -0-, -S-, -SO-, -S0 2 - or -CO-; Z and Z' are each a monovalent unsaturated organo moiety; and n is an integer from about 3 to about 200.
Claim 49
Dependent Claim
15 words
Process of preparing the homopolymer of Claim 33 by polymerizing said end-capped polyarylene polyether monomer.
Claim 50
Dependent Claim
37 words
Process as claimed in Claim 39 wherein a free radical initiator, preferably a peroxide, especially dicumyl peroxide, is present in an amount of 0.05 to 1 percent by weight, based on the total amount of the monomer.
Claim 51
Dependent Claim
25 words
Process as claimed in Claim 40 wherein heat, preferably a temperature between 25° to 300°C, is applied to help initiate and carry out the polymerization.
Claim 52
Dependent Claim
58 words
A copolymer comprised of: (A) at least one monomer which is an end-capped polyarylene polyether having the formula Z (̵ polyarylene polyether chain )̵ Z' wherein Z and Z' are each a monovalent unsaturated organo moiety, the polyarylene polyether chain being substituted or unsubstituted: and (B) at least one monomer having at least one monovalent unsaturated organo moiety.
Claim 53
Dependent Claim
58 words
A copolymer comprised of: (A) at least one monomer which is an end-capped polyarylene polyether having the formula Z (̵ polyarylene polyether chain )̵ Z' wherein Z and Z' are each a monovalent unsaturated organo moiety, the polyarylene polyether chain being substituted or unsubstituted: and (B) at least one monomer having at least one monovalent unsaturated organo moiety.
Claim 54
Dependent Claim
20 words
The copolymer as claimed in Claim 42 wherein the monovalent unsaturated organo moiety is an alkylene, aralkylene, or cycloalkylene moiety.
Claim 55
Dependent Claim
99 words
The copolymer as claimed in Claim 42 or 43 wherein the monovalent unsaturated organo moiety is selected from the group consisting of: wherein R 1 , R 2 and R 3 each is hydrogen, an aliphatic hydrocarbon radical containing 1 to 20 carbon atoms, an alicyclic hydrocarbon radical containing 1 to 20 carbon atoms or an aromatic radical, and R 4 , R 5 and R6 each is a divalent alkylene radical having 1 to 20 carbon atoms, a divalent arylene radical having 6 to 10 carbon atoms and a divalent cycloalkylene radical containing 3 to 8 carbon atoms.
Claim 56
Dependent Claim
50 words
The copolymer as claimed in Claim 44 wherein R 1 , R 2 and R 3 each is hydrogen, an alkyl radical having 1 to 20 carbon atoms, an aryl radical, an aralkyl radical, an alkaryl radical, an alicyclic radical having 3 to 8 carbon atoms or a bicyclic radical.
Claim 57
Dependent Claim
30 words
The copolymer as claimed in Claim 44 or 45 wherein R 4 , R 5 and R 6 each is a divalent alkylene radical having 1 to 8 carbon atoms.
Claim 58
Dependent Claim
247 words
The copolymer as claimed in Claim 42 wherein monomer (B) is a monomer containing at least one reactive vinyl group R 7 R 8 C=CR 9 -, reactive vinylidene group R 7 R 8 C=C and/or reactive vinylene group -CR 10 =CR 11 -, wherein R 7 , R 8 , Rg, R 10 and R 11 each is (a) hydrogen, (b) alkyl having 1 to 4 carbon atoms, (c) alkoxy having 1 to 4 carbon atoms, (d) alkylcarboxy having 2 to 12 carbon atoms, (e) aryl having 6 to 10 carbon atoms, (f) alkoxycarbonyl having 2 to 12 carbon atoms, (g) substituted aryl having 6 carbon atoms and being substituted with at least one halogen, nitrile, alkyl having 1 to 4 carbon atoms, and/or alkoxy having 1 to 4 carbon atoms, (h) aralkyl wherein the alkyl has 1 to 4 carbon atoms and the aryl has 6 to 10 carbon atoms, (i) substituted aralkyl wherein the alkyl has 1 to 4 carbon atoms, the aryl has 6 to 10 carbon atoms and the substituents are halogen, alkyl having 1 to 4 carbon atoms, nitrile and/or alkoxy having 1 to 4 carbon atoms, (j) substituted alkyl having 1 to 4 carbon atoms and being substituted with nitrile, halogen and/or alkoxy having 1 to 4 carbon atoms, (k) substituted alkylcarboxy having 2 to 12 carbon atoms and substituted with halogen and/or nitrile, or (1) substituted alkoxycarbonyl having 2 to 12 carbon atoms and substituted with halogen and/or nitrile.
Claim 59
Dependent Claim
51 words
The copolymer as claimed in Claim 42 wherein monomer (B) is styrene, substituted styrene RnC6H5-nCH=CH2 wherein n is 1 to 5 and R is halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, -CN and/or -NO 2 , or α-substituted styrene wherein R 2 alkyl
Claim 60
Dependent Claim
61 words
The copolymer as claimed in Claim 42 wherein monomer (B) is alkylacrylate wherein the alkyl radical has 1 to 11 carbon atoms, alkoxyacrylate wherein the alkyl radical has 1 to 11 carbon atoms, alkyl methacrylate wherein the alkyl radical has 1 to 10 carbon atoms, alkoxy methacrylate wherein the alkyl radical has 1 to 10 carbon atoms, or an unsaturated nitrile.
Claim 61
Dependent Claim
25 words
The copolymer as claimed in Claim 42 wherein monomer (B) is an allyl alkyl ether, an allyl halide, allyl ester, allylbenzene,an allylbenzene derivative or styrene.
Claim 62
Dependent Claim
20 words
The copolymer as claimed in Claim 42 wherein monomer (B) has one reactive unsaturated group or multiple reactive unsaturated groups.
Claim 63
Dependent Claim
54 words
Process of preparing the copolymer of Claim 42 by polymerizing said end-capped polyarylene polyether monomer (A) and monomer (B), preferably in the presence of a free radical initiator, especially a peroxide like dicumyl peroxide, in an amount of 0.05 to 1 percent by weight, based on the total amount of monomers (A) and (B).
Claim 64
Dependent Claim
24 words
Process as claimed in Claim 52 wherein heat,preferably a temperature between 25° to 300°C, is applied to help initiate and carry out the polymerization.
Claim 65
Dependent Claim
36 words
Process as claimed in Claim 52 wherein the molar ratio of monomer (A) to monomer (B) is between 4 to 1 and 0.8 to 1, preferably (A) and (B) are present in approximately equal stoichiometric amounts.
Claim 66
Dependent Claim
24 words
A mixture of a heat-hardenable resin and from about 1 to 99 parts by weight of the thermosetting end-capped polyarylene polyether of Claim 1.
References Cited (Backward Citations)
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