GB1561140A - Polyphenylene ether resins - Google Patents
Polyphenylene ether resins Download PDFInfo
- Publication number
- GB1561140A GB1561140A GB54158/76A GB5415876A GB1561140A GB 1561140 A GB1561140 A GB 1561140A GB 54158/76 A GB54158/76 A GB 54158/76A GB 5415876 A GB5415876 A GB 5415876A GB 1561140 A GB1561140 A GB 1561140A
- Authority
- GB
- United Kingdom
- Prior art keywords
- composition
- phosphate
- carbon atoms
- phthalate
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
- C08L71/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
- C08L71/12—Polyphenylene oxides
- C08L71/123—Polyphenylene oxides not modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0016—Plasticisers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
Description
(54) IMPROVEMENTS IN POLYPHENYLENE
ETHER RESINS
(71) We, GENERAL ELECTRIC
COMPANY, a Corporation organized and existing under the laws of the State of New
York, United States of America, of 1 River
Road, Schenectady 12305, State of New
York, United States of America, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement:- The present invention relates to polyphenylene ether resins and in particular to flexible polyphenylene ether resins.
Poly(2,6-dimethyl-l,4-phenylene ether) is sold commercially as pure polymer and in combination with a styrene resin. These materials are characterized by toughness hardness and good dimensional stability at elevated temperatures. In U.S. Patent No, 3,373,226, a procedure is disclosed for preparing flexible films by cross-linking a film of polyphenylene ether polymers, swelling the cross-linked film and biaxially orienting the film by securing the edges of the swollen film during a drying stage.
Plasticized polyphenylene ethers are disclosed in U.S. Patent No. 3,356,761 as being useful for film and fiber application.
Polymerizable vinyl monomers, such as styrene monomer, were employed as the plasticizing agents of that patent. U.S.
Patent No. 3,639,506 disclosed rigid polyphenylene ether-phosphate compositions that fail to suggest the present invention.
It has now been found that phosphate and phthalate flexibilizers may be employed to make flexible polyphenylene ether compositions that while being flexible, still have good physical properties that make them useful for film and molding applications that require a flexible thermoplastic.
Flexible polyphenylene ether resin compositions can provide an attractive alternative to plasticized polyvinyl chloride resins as they do not form hydrogen chloride when they are incinerated. In recent times, the widely used polyvinyl chloride resins have been criticized for this property, and therefore, the flexibilized polyphenylene ethers of this invention provide an alternate material that does not have the disposal problem that is inherent with polyvinyl chloride resins.
As used herein, the term flexibilized is employed in its art-recognized sense to define a composition, a "flexisol" so to speak, that is calenderable, when fabricated between oppositely rotating mill rolls, into sheets of 1/8" or less thickness. Such sheets may be bent without causing cracking or crazing, and in suitably thin forms, they will drape and be suitable for purposes such as shower curtains, and automobile upholstery, thus opening up a whole new field of use for polyphenylene ether resins.
Accordingly, the present invention provides a flexibilized thermoplastic composition which comprises:
(a) a polyphenylene ether resin: or a polyphenylene ether resin in admixture with an alkenyl aromatic resin; and
(b) from 50 to 100 parts by weight, per 100 parts by weight of resin, of a flexibilizer selected from o,p-toluene sulfonamide and substituted derivatives thereof, alkyl esters of trimellitic acid, hydrogenated terphenyl, epoxy stearates, epoxy terranyarophthalates, epoxidized oils, mineral oil, phosphate flexibilizers of the formula:
where each Q is independently alkyl, cycloalkyl, aryl, alkaryl, aralkyl, hydroxyalkyl, hydroxyaryl, hydroxyalkaryl, halogen or hydrogen, and phthalate flexibilizers of the general formula::
wherein R9 and R10 are independently alkyl, aryl, cycloalkyl, alkaryl, aralkyl, hydroxyalkyl, hydroxyaryl or hydroxyalkaryl.
The substituted derivatives of o,ptoluene sulfonamide include N-ethyl-o,p- toluenesulfonamide and N-cyclohexyl-ptoluene-sulfonamide. Other substituted derivatives having straight and branched chain alkyl groups of 1--10 carbon atoms on the N atom may also be employed.
The alkyl esters of trimellitic acid include those esters having straight and branched chain alkyl groups of 1--10 carbon atoms.
Examples of these esters also include tri-2ethylhexyl trimellitate, n-octyl, n-decyl trimellitate and triisodecyl trimellitate.
The epoxy stearates include epoxy butyl stearate, epoxy n-hexyl stearate, epoxyisooctyl stearate and other epoxidized alkyl stearates wherein the alkyl group is a straight or branched chain hydrocarbon group having from I to 10 carbon atoms.
The epoxy tetrahydrophthalates include the epoxidized alkyl tetrahydrophthalates wherein the alkyl group is a straight or branched chain hydrocarbon group having from 1 to 10 carbon atoms such as epoxy 2ethylhexyl tetrahydrophthalates and epoxy isodecyl tetrahydrophthalates.
The epoxidized oils include epoxidized soybean oil and 2-ethylhexyl tallate.
It is preferred to use the phosphate and phthalate flexibilizers.
The preferred polypnenylene ether resins are of the formula:
wherein the oxygen ether atom of one unit is connected to the benzene nucleus of the next adjoining unit, n is a positive number and is at least 50, and each Q is a hydrogen or halogen atom or a hydrocarbon radical free of a tertiary alpha carbon atom, a halohydrocarbon radical having at least two carbon atoms between the halogen atom and the phenyl nucleus, or a hydrocarbonoxy or halohydrocarbonoxy radical having at least two carbon atoms.
The preferred polyphenylene ether resin is a poly(2,6-dimethyl- 1 ,4-phenylene ether) resin having an intrinsic viscosity of at least 0.4 dl/g as measured in chloroform solution at 30"C.
The alkenyl aromatic resin should preferably have at least 25% of its units derived from a compound of the formula:
wherein R' and R2 are alkyl or alkenyl groups of up to 6 carbon atoms or hydrogen; R3 and R4 are chlorine, bromine, hydrogen or alkyl of from 1 to 6 carbon atoms; R5 and R6 are hydrogen or alkyl or alkenyl groups of up to 6 carbons or R5 and
R6 may be concatenated together with hydrocarbyl groups to form a naphthyl group.
Materials that may be copolymerized with the vinyl aromatic monomer include those having the general formula:
wherein R7 and R8 represent a hydrogen or halogen atom. analkyl group of 1--4 carbon atoms, carboalkoxy having from 1--4 carbon atoms or R7 and R8 taken together represent an anhydride linkage (-COOOC-) and R9 is hydrogen, vinyl, alkyl or alkenyl group having up to 12 carbon atoms, cycroalkyl having 3 to 6 carbon atoms, carboalkoxy having 2 to 6 carbon atoms, alkoxy-alkyl having 2 to 6 carbon atoms, alkylcarboxy having 2 to 6 carbon atoms, ketoxy, halogen, carboxy alkyl having 1 to 6 atoms, cyano or pyridyl and n is 0 or a whole number from I to 9.
The general formulae set forth above include by way of example, homopolymers such as homopolystyrene and monochloropolystyrene, the modified polystyrenes, such as rubber-modified, highimpact polystyrene and the styrene containing copolymers, such as the styrene acrylonitrile copolymers, styrene butadiene copolymers, styrene acrylonitrile-a-alkyl styrene copolymers, styrene-acrylonitrilebutadiene copolymers, poly-methyistyrene, copolymers which include ethylvinylbenzene, or divinylbenzene and styrene maleic anhydride copolymers and block copolymers of styrene-butadiene and styrene-butadiene-styrene.
The styrene-maleic anhydride copolymers are described in U.S. Patents
No. 3,971,939; 3,336,267 and 2,769,804.
The rubber-modified, high-impact styrene resins are preferred and these may be made by well known procedures with rubbers such as nitrile rubbers, polybutadiene rubber, styrene-butadiene rubber, polysulfide rubber, ethylenepropylene copolymers, propylene oxide and
EPDM. These materials are well known and many are commercially available.
The phosphate flexibilizer has, as indicated above, the formula:
wherein the radicals Q are the same or different radicals, and are alkyl, such as straight and branched chain alkyl of from 1 to 10 carbon atoms such as methyl, propyl, n-butyl, hexyl and heptyl; cycloalkyl such as those cycloalkyl radicals having from 1 to 8 carbon atoms such as cyclopropyl, cyclobutyl, and cyclohexyl; aryl such as those aryl radicals having from 6 to 14 carbon atoms such as phenyl and naphthyl; alkaryl such as those radicals having from 1 to 5 straight or branched chain alkyl radicals having from I to 10 carbon atoms on a phenyl or naphthyl nucleus, e.g., 2methylphenyl, 4-n-butylphenyl, and 2ethylphenyl; aralkyl such as phenyl or naphthyl substituted straight or branched chain alkyl radicals having from 1 to 10 carbon atoms such as benzyl, phenethyl, and phenpropyl; hydroxyalkyl having from to 10 carbon atoms such as 2hydroxyethyl, and 4-hydroxyhexyl; hydroxyaryl such as hydroxyphenyl or hydroxynaphthyl, e.g., 4-hydroxy phenyl; hydroxyalkaryl such as cresyl, 4-ethyl-2hydroxyphenyl; halogen such as chlorine, bromine or fluorine; or hydrogen.
Preferred phosphate flexibilizers include cresyl diphenyl phosphate, 2-ethylhexyl diphenyl phosphate, tricresyl phosphate, triiosopropylphenyl phosphate, triphenyl phosphate, triethyl phosphate, dibutyl phenyl phosphate, diethyl phosphate, cresyl diphenyl phosphate, isooctyl diphenyl phosphate, tributyl phosphate, 2-ethylhexyl diphenyl phosphate, isodecyl diphenyl phosphate, isodecyl dicresyl phosphate, didecyl cresyl phsophate tri-n-hexyl phosphate, di-n-octyl phenyl phosphate, di-2ethylhexyl phenyl and tri-2-ethylhexyl phosphate or mixtures thereof.
Phosphates such as triphenyl phosphate will exhibit good compatibility with polyphenylene ethers up to 40 parts of triphenyl phosphate, per 100 parts of total composition. At higher concentrations, the polyphenylene ether tends to separate from these compositions. Alkylated aryl phosphates such as isopropylated triphenyl phosphate have better compatibility with polyphenylene ethers and may be employed at higher levels with better compatibility.
The phthalate flexibilizers have the formula:
wherein R9 and R'O are independently alkyl, such as straight and branched chain alkyl radicals of from 1 to 30 carbon atoms such as methyl, ethyl, propyl, n-butyl, n-hexyl, octyl, decyl, undecyl, and tridecyl; aryl such as those aryl radicals having from 6 to 14 carbon atoms such as phenyl and naphthyl; cycloalkyl such as those cycloalkyl radicals having from 1 to 8 carbon atoms such as cyclopropyl, cyclobutyl, and cyclohexyl; alkaryl such as those radicals having from I to 5 straight or branched chain alkyl radicals having from 1 to 10 carbon atoms on a phenyl or naphthyl, e.g.
2-methylphenyl, 4-n-butylphenyl. and 2 n-hexylphenyl; aralkyl such as phenyl or naphthyl substituted straight or branched chain alkyl radicals having from I to 10 carbon atoms such as benzyl, phenethyl, and phenpropyl; hydroxyalkyl having from 1 to 10 carbon atoms such as 2hydroxyethyl, and 4-hydroxyhexyl; hydroxyaryl such as hydroxyphenyl or hydroxynaphthyl e.g. 4-hydroxyphenyl; or hydroxyalkaryl such as cresyl, or 4hydroxyphenyl.
Particular phthalates include dibenzyl phthalate, phenyl cresyl phthalate, diethyl phthalate, dimethyl phthalate, phenyl benzyl phthalate, butyl benzyl phthalate, butyl cyclohexyl phthalate, dibutyl phthalate, octyl cresyl phthalate, diphenyl phthalate, di-n-hexyl phthalate, disohexyl phthalate, butyl octyl phthalate, butyl decyl phthalate, diisooctyl phthalate, di-2ethylhexyl phthalate, di-n-octyl phthalate, diisononyl phthalate, diisodecyl phthalate, di-2-propyl heptyl phthalate, di-n-nonyl phthalate, di-n-decyl phthalate, diundecyl phthalate and ditridecyl phthalate.
Generally the compositions of the inventions will comprise either a polyphenylene ether resin or a mixture of a polyphenylene ether resin and an alkenyl aromatic resin and a sufficient amount of flexibilizer to make the composition sufficiently flexible for the desired application. Generally a ratio of 150 parts/100 parts to 30 parts/100 parts of polyphenylene ether resin or polyphenylene ether resin and alkenyl aromatic resin to plasticizer may be employed. The relative proportions of polyphenylene ether and alkenyl aromatic resin may vary from 1--99 parts by weight to 99-1 parts by weight.
The preferred composition will have between 15-50 parts by weight of polyphenylene ether resin and 85-50 parts by weight of an alkenyl aromatic resin.
It has been found that at a 40:60 ratio of
polyphenylene ether to triphenylphosphate,
the extruded strands are both tough and
flexible.
The flexibilized compositions may be
employed in various applications that
require flexible thermoplastic materials.
The applications include sheet and film products as well as tubing and packaging. If desired, the flexibilized compositions may be foamed to form structural articles having diverse application. Various foaming techniques may be used that are well known
in the art such as those disclosed in the
Encyclopedia of Polymer Science, Vol. 2, pages 532-561.
The technique employed in preparing the
flexible compositions is not critical, and any
of the well known procedures in the art are
suitable. For example, the composition may
be prepared by one or more passes through
an extruder. Alternately, the compositions
may be prepared by dissolving the
components in a mutual solvent and
recovering the blended materials by
evaporation of the solvent or by
precipitation with a non-solvent.
The compositions of this invention have a heat distortion temperature of 125"F or
lower (ASTM method 264 psi).
EXAMPLE I
A composition was prepared by blending in an extruder 40 parts by weight of poly(2,6-dimethyl- 1 4-phenylene ether)* and 60 parts by weight of triphenyl phosphate. the composition had the following physical properties:
Tensile strength (psi) 1550
Elongation (%) 177 *PPO General Electric Company
EXAMPLE 2
Following the procedure of Example 1, the following composition was prepared:
Parts by
weight Poly(2,6-dimethyl- 1,4-phenylene ether) 25
Polystyrene [Dylene 8G Arco
(Registered trade Mark)
crystal polystyrene] 25
Triphenyl phosphate 50
The composition had the following physical properties:
Tensile Strength (psi) 1350
Elongation (%) 188
EXAMPLE 3
Following the procedure of Example 1, the following composition was prepared::
Parts by
weight Poly(2,6-dimethyl- 1 4-phenylene ether) 50
Triphenyl phosphate 50
The composition had the following physical properties:
Tensile Strength (psi) 1810
Elongation (%) 123
EXAMPLE 4
Following the procedure of Example I, the following composition was prepared:
Parts by
weight Poly(2,6-dimethyl- I ,4-phenylene ether) 50
Triphenyl phosphate 50
Rubber-modified, high-impact
polystyrene 20
The composition had the following physical properties:
Tensile Strength (psi) 2640
Elongation (%) 93
EXAMPLE 5
Following the procedure of Example 1, the following composition was prepared: :
Parts by
weight Poly(2,6-dimethyl- 1 4-phenylene ether) 50
Triphenyl phosphate 17
Triisopropylphenyl phosphate* 33
*Kronitex 300, a mixture containing triisopropylphenyl phosphates as obtained from the alkylation of phenol with propylene and subsequent reaction with phosphorus pentachloride.
The composition had the following physical properties:
Tensile Strength (psi) 2100
Elongation (%) 119
EXAMPLE 6
Following the procedure of Example 1, the following composition was prepared:
Parts by
weight Poly(2*6-dimethyl- 1,4-phenylene ether) 50
Triphenyl phosphate 25
Triisopropylphenyl phosphate
(Kronitex 300) 25 The composition had the following physical properties:
Tensile Strength (psi) 2100 Elongation ("") 130
EXAMPLE 7
Following the procedure of Example 1, the following composition was prepared:
Parts by
weight Poly(2.6-dimethyl-l 1.4-phenylene ether) 50
Triisopropylphenyl phosphate
(Kronitex 300) 50
The composition had the following physical properties::
Tensile Strength (psi) 1760
Elongation (%) 133
WHAT WE CLAIM IS:- 1. A flexibilized thermoplastic composition which comprises:
(a) a polyphenylene ether resin; or a polyphenylene ether resin in admixture with an alkenyl aromatic resin: and
(b) from 50 to 100 parts by weight, per 100 parts bv weight of resin, of a flexibilizer selected from o,p-toluene sulfonamide and substituted derivatives thereof. alkyl esters of trimellitic acid, hydrogenated terphenyl.
epoxy stearatesw epoxv tetrahydrophthalates, epoxidized oils, mineral oil, phosphate flexibilizers of the formula:
where each Q is independently alkyl, cvcloalkyl, aryl. alkaryl, aralkyl, hydroxyalkyl, hydroxyaryl, hydroxyalkaryl, halogen or hydrogen and phthalate flexibilizers of the general formula:
wherein R9 and R10 are independently alkvl.
aryl. cycloalkyl. alkaryl. aralkyl.
hydroxyalkyl. hvdrusvarvl or hydroxyalkaryl .
2. A composition as claimed in Claim 1, wherein the polyphenylene ether resin has the formula:
wherein the oxygen ether atom of one unit is connected to the benzene nucleus of the next adjoining unit, n is a positive number and is at least 50, and each Q is a hydrogen or halogen atom or a hydrocarbon radical free of a tertiary alpha carbon atom, a halohydrocarbon radical having at least two carbon atoms between the halogen atom and the phenyl nucleus, or a hydrocarbonoxy or halohydrocarbonoxy radical having at least two carbon atoms.
3. A composition as claimed in Claim 2, wherein the polyphenylene ether resin is poly(2,6-dimethyl-l 1,4-phenylene ether).
4. A composition as claimed in Claim 1, wherein at least 25; of the units of said alkenyl aromatic resin are derived from a monomer of the formula:
wherein R' and R2 are alkyl or alkenyl groups of up to 6 carbon atoms or hydrogen;
R3 and R4 are chlorine, bromine, hydrogen or alkyl of from I to 6 carbon atoms: R5 and R6 are hydrogen or alkyl or alkenyl groups of up to 6 carbons or R5 and R6 may be concatenated together with hydrocarbyl groups to form a naphthyl group.
5. A composition as claimed in any preceding claim, wherein the flexibilizer is cresyl diphenyl phosphate, 2-ethylhexyl diphenyl phosphate, tricresyl phosphate, triphenyl phosphate, isopropyl triphenyl phosphate or a mixture thereof.
6. A composition as claimed in any of
**WARNING** end of DESC field may overlap start of CLMS **.
Claims (7)
- **WARNING** start of CLMS field may overlap end of DESC **.Parts by weight Poly(2*6-dimethyl- 1,4-phenylene ether) 50 Triphenyl phosphate 25 Triisopropylphenyl phosphate (Kronitex 300) 25 The composition had the following physical properties: Tensile Strength (psi) 2100 Elongation ("") 130 EXAMPLE 7 Following the procedure of Example 1, the following composition was prepared: Parts by weight Poly(2.6-dimethyl-l 1.4-phenylene ether) 50 Triisopropylphenyl phosphate (Kronitex 300) 50 The composition had the following physical properties: Tensile Strength (psi) 1760 Elongation (%) 133 WHAT WE CLAIM IS:- 1.A flexibilized thermoplastic composition which comprises: (a) a polyphenylene ether resin; or a polyphenylene ether resin in admixture with an alkenyl aromatic resin: and (b) from 50 to 100 parts by weight, per 100 parts bv weight of resin, of a flexibilizer selected from o,p-toluene sulfonamide and substituted derivatives thereof. alkyl esters of trimellitic acid, hydrogenated terphenyl.epoxy stearatesw epoxv tetrahydrophthalates, epoxidized oils, mineral oil, phosphate flexibilizers of the formula:where each Q is independently alkyl, cvcloalkyl, aryl. alkaryl, aralkyl, hydroxyalkyl, hydroxyaryl, hydroxyalkaryl, halogen or hydrogen and phthalate flexibilizers of the general formula:wherein R9 and R10 are independently alkvl.aryl. cycloalkyl. alkaryl. aralkyl.hydroxyalkyl. hvdrusvarvl or hydroxyalkaryl .
- 2. A composition as claimed in Claim 1, wherein the polyphenylene ether resin has the formula:wherein the oxygen ether atom of one unit is connected to the benzene nucleus of the next adjoining unit, n is a positive number and is at least 50, and each Q is a hydrogen or halogen atom or a hydrocarbon radical free of a tertiary alpha carbon atom, a halohydrocarbon radical having at least two carbon atoms between the halogen atom and the phenyl nucleus, or a hydrocarbonoxy or halohydrocarbonoxy radical having at least two carbon atoms.
- 3. A composition as claimed in Claim 2, wherein the polyphenylene ether resin is poly(2,6-dimethyl-l 1,4-phenylene ether).
- 4. A composition as claimed in Claim 1, wherein at least 25; of the units of said alkenyl aromatic resin are derived from a monomer of the formula:wherein R' and R2 are alkyl or alkenyl groups of up to 6 carbon atoms or hydrogen; R3 and R4 are chlorine, bromine, hydrogen or alkyl of from I to 6 carbon atoms: R5 and R6 are hydrogen or alkyl or alkenyl groups of up to 6 carbons or R5 and R6 may be concatenated together with hydrocarbyl groups to form a naphthyl group.
- 5. A composition as claimed in any preceding claim, wherein the flexibilizer is cresyl diphenyl phosphate, 2-ethylhexyl diphenyl phosphate, tricresyl phosphate, triphenyl phosphate, isopropyl triphenyl phosphate or a mixture thereof.
- 6. A composition as claimed in any ofClaims I to 4, wherein the flexibilizer is butyl benzyl phthalate, dicyclohexyt phthalate or di-2-ethylhexyl phthalate.
- 7. A composition as claimed in Claim I substantially as hereinbefore described in any one of the Examples,
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US64565375A | 1975-12-31 | 1975-12-31 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1561140A true GB1561140A (en) | 1980-02-13 |
Family
ID=24589901
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB54158/76A Expired GB1561140A (en) | 1975-12-31 | 1976-12-24 | Polyphenylene ether resins |
Country Status (7)
Country | Link |
---|---|
JP (1) | JPS5290559A (en) |
AU (1) | AU506630B2 (en) |
DE (1) | DE2659331A1 (en) |
FR (1) | FR2337179A1 (en) |
GB (1) | GB1561140A (en) |
MX (1) | MX144325A (en) |
NL (1) | NL7614511A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0083049A2 (en) * | 1981-12-28 | 1983-07-06 | General Electric Company | Composition of PPE and PS-grafted EPDM and plasticizer |
EP0137545A2 (en) * | 1983-10-12 | 1985-04-17 | General Electric Company | Articles manufactured wholly or partly from a polymer mixture and comprising a lacquer layer or an adhesive layer |
EP0137546A2 (en) * | 1983-10-12 | 1985-04-17 | General Electric Company | Polyphenylene ether composition containing an epoxy compound |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS57500152A (en) * | 1980-01-14 | 1982-01-28 | ||
US4373045A (en) * | 1980-04-15 | 1983-02-08 | General Electric Company | Polyphenylene ether molding compositions that include an alkenyl aromatic resin, an ethylene propylene rubber and a triaryl phosphate |
EP0054845A3 (en) * | 1980-12-18 | 1982-09-22 | General Electric Company | Mineral filled polyphenylene ether compositions having improved properties |
US4444934A (en) * | 1982-12-01 | 1984-04-24 | Asahi Kasei Kogyo Kabushiki Kaisha | Heat resistant thermoplastics resin composition excellent in processing flowability |
DE3337629A1 (en) * | 1983-10-15 | 1985-04-25 | Chemische Werke Hüls AG, 4370 Marl | METHOD FOR PRODUCING THERMOPLASTIC MOLDS CONTAINING POLYPHENYLENE ETHER |
CA2015525A1 (en) * | 1989-08-18 | 1991-02-18 | Gim F. Lee Jr. | Thermoplastic compositions which contain polyolefins and polyphenylene ethers, and articles made therefrom |
DE4101804A1 (en) * | 1991-01-23 | 1992-07-30 | Basf Ag | SELF-EXTINGUISHING, HALOGEN-FREE, FLAME-PROTECTED SHAPE SIZE WITH IMPROVED FIRE RESISTANCE |
DE4101805A1 (en) * | 1991-01-23 | 1992-07-30 | Basf Ag | THERMOPLASTIC MOLDING MATERIAL WITH INCREASED FLOWABILITY |
-
1976
- 1976-11-23 AU AU19888/76A patent/AU506630B2/en not_active Expired
- 1976-12-17 MX MX167493A patent/MX144325A/en unknown
- 1976-12-24 GB GB54158/76A patent/GB1561140A/en not_active Expired
- 1976-12-24 FR FR7639046A patent/FR2337179A1/en active Granted
- 1976-12-28 NL NL7614511A patent/NL7614511A/en not_active Application Discontinuation
- 1976-12-29 DE DE19762659331 patent/DE2659331A1/en not_active Withdrawn
- 1976-12-29 JP JP16097076A patent/JPS5290559A/en active Pending
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0083049A2 (en) * | 1981-12-28 | 1983-07-06 | General Electric Company | Composition of PPE and PS-grafted EPDM and plasticizer |
EP0083049A3 (en) * | 1981-12-28 | 1984-02-22 | General Electric Company | Composition of ppe and ps-grafted epdm and plasticizer |
EP0137545A2 (en) * | 1983-10-12 | 1985-04-17 | General Electric Company | Articles manufactured wholly or partly from a polymer mixture and comprising a lacquer layer or an adhesive layer |
EP0137546A2 (en) * | 1983-10-12 | 1985-04-17 | General Electric Company | Polyphenylene ether composition containing an epoxy compound |
WO1985001738A1 (en) * | 1983-10-12 | 1985-04-25 | General Electric Company | Polyphenylene ether composition containing an epoxy compound |
EP0137546A3 (en) * | 1983-10-12 | 1985-07-03 | Gen Electric | Polyphenylene ether composition containing an epoxy compound |
EP0137545A3 (en) * | 1983-10-12 | 1985-07-03 | General Electric Company | Articles manufactured wholly or partly from a polymer mixture and comprising a lacquer layer or an adhesive layer |
Also Published As
Publication number | Publication date |
---|---|
AU1988876A (en) | 1978-06-01 |
JPS5290559A (en) | 1977-07-29 |
NL7614511A (en) | 1977-07-04 |
MX144325A (en) | 1981-09-29 |
DE2659331A1 (en) | 1977-09-01 |
FR2337179B1 (en) | 1980-04-04 |
AU506630B2 (en) | 1980-01-17 |
FR2337179A1 (en) | 1977-07-29 |
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Date | Code | Title | Description |
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PS | Patent sealed [section 19, patents act 1949] | ||
PCNP | Patent ceased through non-payment of renewal fee | ||
PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19951224 |