WO1981002019A1 - Polyphenylene ether molding compositions that include an alkenyl aromatic resin and an epdm rubber - Google Patents
Polyphenylene ether molding compositions that include an alkenyl aromatic resin and an epdm rubber Download PDFInfo
- Publication number
- WO1981002019A1 WO1981002019A1 PCT/US1981/000043 US8100043W WO8102019A1 WO 1981002019 A1 WO1981002019 A1 WO 1981002019A1 US 8100043 W US8100043 W US 8100043W WO 8102019 A1 WO8102019 A1 WO 8102019A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- thermoplastic molding
- molding composition
- rubber
- parts
- ether resin
- Prior art date
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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
- C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
-
- 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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/16—Elastomeric ethene-propene or ethene-propene-diene copolymers, e.g. EPR and EPDM rubbers
-
- 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
-
- 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
-
- 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
Definitions
- Polyphenylene Ether Molding Compositions that include An Alkenyl Aromatic Resin And An EPDM Rubber
- polyphenylene ether resin is descriptive of a well known group of polymers that may be made by a variety of catalytic and non-catalytic processes.
- certain of the polyphenylene ethers are disclosed in Hay, U.S. Patent No. 3,306,874 and 3,306,875, and in Stamatoff, 3,257,357 and 3,257,358.
- the polyphenylene ethers are prepared by an oxidative coupling reaction comprising passing an oxygen-containing gas through a reaction solution of a phenol and a metal-amine complex catalyst.
- Other disclosures relating to processes for preparing polyphenylene ethers are found in Fox, U.S. Patent No.
- Patent No. 3,573,257 (jaetal-alcoholate or phenolate); Kobayashi et al, U.S. Patent No. 3, 455, 880 (cobalt chelates); and the like.
- the polyphenylene ethers are produced by reacting the corresponding phenolate ion with an initiator, such as a peroxy acid salt, an acid peroxide, a hypophalite, and the like, in the presence of a complexing agent. Disclosures relating to non-catalytic processes, such as oxidation with lead dioxide, silver oxide, etc., are described in Price et al, U.S. Patent No. 3,382,212. Cizek, U.S. 3,383,435 discloses compositions of polyphenylene ethers and styrene resins. All of the above- mentioned disclosures are incorporated herein by reference.
- compositions of a polyphenylene ether resin there are described compositions of a polyphenylene ether resin; polystyrene or high impact polystyrene; and either an ethylene-prcpylene copolymer, polyisobucylane or an ⁇ -olefin copolymer.
- U.S. 3,943,191; U.S. 4,101.503; U.S. 4,101,504; U.S. 4,101,505 and U.S. 4,102,850 all disclose compositions that include a polyphenylene ether resin and an alkenyl resin that is modified with an interpolymerized EPDM rubber.
- compositions of a polyphenylene ether, and an alkenyl aromatic resin are modified by the inclusion of a small quantity of an EPDM rubber, the resulting compositions have improved Izod and Gardner impact strength and ductility as compared to analogous compositions prepared with ethylene prcpylene rubber.
- the invention also includes compositions of a polyphenylene ether resin, a phosphate compound and an EPDM rubber and optionally a thermoplastic rubber. Accordingly, it is a primary object of this invention to provide thermoplastic molding compositions of a polyphenylene ether resin, an alkenyl aromatic resin and an EPDM rubber.
- the polyphenylene ether resins are polymers having units of the formula:
- Q is selected from the group consisting of hydrogen, hydrocarbon radicals, halohydrocarbcn radicals having at least two carbon atoms between the halogen atom and the phenyl nucleus, hydrocarbonoxy radicals and halohydrocarbonoxy radicals having at least two carbon atoms between the halogen atom and the phenyl nucleus, Q' and Q" are the same as Q and in addition halogen with the proviso that Q and Q' are both free of a tertiary carbon atom and n is an integer of at least 50.
- the preferred polyphenylene ether resin is a poly (2, 6-dimethyl-1,4-phenylene) ether resin having an intrinsic viscosity of from about 0.40 dl/g to about 0.65 dl/g as measured in chloroform at 30oC.
- the alkenyl aromatic resin will have at least 25% of its units derived from monomers of the formula:
- R 1 and R 2 are selected from the group consisting of lower alkyl or alkenyl groups of from 1 to 6 carbon atoms and hydrogen;
- R 3 , R 4 and R 5 are selectee from the group consisting of chloro, brorao, hydrogen and (lower) alkyl of from 1 to 6 carbon atoms;
- R 6 and R 7 are selected from the group consisting of hydrogen and (lower) alkyl and alkenyl groups of from 1 to 6 carbon atoms or R 5 and R 6 may be concatenated together with hydrocarbyl groups to form a naphthyl group.
- Styrene is the preferred alkenyl aromatic compound.
- An ⁇ , 3-unsaturated cyclic anhydride may be copolymerized with the vinyl aromatic compound.
- These compounds may be represented by the formula wherein the dotted lines represent a single or double carbon to carbon bond, R 7 and R 8 taken together represents a
- R 9 is selected from the group consisting of hydrogen, vinyl, alkyl, alkenyl, alkylcarboxylic or alkenylcarboxylic of from 1 to 12 carbon atoms, n is 1 or 2, depending on the position of the carbon-carbon double bond, and m is an integer of from 0 to about 10. Amounts from 0 to 1 part per weight of anhydride per part by weight of alkenyl aromatic resin may be used. Examples include maleic anhydride, citraconic anhydride, itaconic anhydride, aconitic anhydride and the like.
- Rubber may be employed in preparing the rubber-modified polymers of a vinyl aromatic compound such as polybutadiene rubber, butyl rubber, styrene-butadiene rubber, acrylonitrile rubber, ethylene propylene copolycers, natural rubber, EPDM rubbers, polysulfide rubber, propylene oxide and the like.
- the rubber may be present at from 0.5 to 25 parts per weight per 100 parts of alkenyl aromatic resin
- the EPDM rubbers are rubbery incarpolymers comprising mixtures of raono-olefins and a polyene including those prepared from ethylene, an alpha-olefin and a polyene.
- Preferred types comprise 10-90 mole percent of ethylene, 10-90 mole percent of an alpha-olefin containing 3-16 carbon atoms, and 0.1 - 12 mole percent of a polyene that is a nor-conjugaced cyclic or open-chain diene having 5-20 carbon atoms.
- Especially preferred are those alpha-olefins having 3-10 carbon atoms and non-conjugated cyclic or open-chain dienes having 5-10 carbon atoms.
- EPDM rubbers include the ethylene-propylene- ethylidene norbomene terpolymer and those described in Ritchie, Vinyl and Allied Polymers, Vol. 1 page 121 (1968) which is incorporated by reference.
- the preferred EPDK rubbery inter- polymers are those comprising ethylene, propylene and 5-ethylidene -2-norbomene; or ethylene, propylene and 1,4-hexadiene; and of ethylene, propylene and dicyclopentadiene.
- compositions of the invention may comprise from
- reinforcing fillers may be added to the composition in reinforcing amounts such as from 1 to 40 parts by weight per 100 parts by weight of total composition of fibrous glass, quartz, matal fibers, woilastor.ite cr the fillers mentioned in U.S. 4,080,351 column 3 and 4, which is incorporated by reference.
- Flame recardants such as chose described in U.S. 3,833,535 which is incorporated in the composition of the invention nay also be present in addition to non-reinforcing fillers.
- Phosphates may be utilized in combination with the polyphenylene ether and the EPDM rubbery interpolymers and optionally a thermoplastic rubber.
- Suitable phosphates include phosphates of the formula:
- each Q represents the same or different radicals including hydrocarbon radicals such as alkyl, cycloalkyl, aryl, alkyl substituted aryl, and aryl substituted alkyl; and combinations thereof provided that at least one of said Q's is aryl.
- Suitable phosphates include, phenylbisdodecyl phosphate, phenylbisneopentyl phosphate, phenylbis 3,5,5'-trimethylhexyl phosphate), ethyldiphenyl phosphate, 2-ethylhexyl di(p-tolyl) phosphate, bis (2-ethylhexyl) p-toiylphosphate, tritolyl phosphate, bis (2-ethylhexyl)-phenyl phosphate, tri- (nonylphenyl) phosphate, di(dodecyl) p-colyl phosphate, tricesyl phosphate, triphenyl phosphate, halogenated triphenyl phosphate, dibutylphenyl phosphate, 2-chloroethyldiphenyl phosphate, p-tolyl bis (2,5,5'-trimethylhexyl phosphat
- the preferred phosphates are those where each Q is aryl.
- the most preferred phosphate is triphenyl phosphate.
- a composition comprised of mixed triaryl phosphates, with one or more isopropyl groups on the aryl rings, such as Kronitex 50 supplied by FMC may also be utilized.
- these compositions will comprise from 65-95 parts by weight of the polyphenylene ether resin; from 35-5 parts by weight of the phosphate and from 1-15 parts by weight of the rubbery interpolym ⁇ r of a mixture of mono oiefins and a polyene alone or in combination with a thermcolastic rubber. If such a mixture is utilized, it should contain a minimum of 257. by weight of the rubbery interpolymer.
- thermoplastic rubbers of the A3A type with or without a saturated midblock are respectively described in U.S. 3,646,162 and U.S. 3,595,942 which are incorporated by reference.
- the compositions may be prepared by tumble blending the components with or without suitable reinforcing agents, stabilizers, pigments, fillers, flame retardants, plasticizers or extrusion aids. The blended components may then be extruded into a continuous strand, the strands are chopped into pellets and the pellets may be molded to any desired shape
- Vistalon 702 (Exxon) a copolymer of ethylene and propylene containing 75 mol percent ethylene.
- Nordel 1500 (Dupont) terpolymer of ethylene, propylene and 1,4-hexadiene containing about 80 mol percent ethylene, 13 mol percent propylene and 7 mol percent hexadiene.
- Example 2 A composition containing 90 parts by weight of a poly (2 ,6-dimethyl-1,4-phenylene) ether resin and 10 parts of tri- phenylphosphate, and blends of 90 parts of a poly (2, 6-dimethyl-1,
- Example 3 A composition of 91 parts ⁇ oly(2, 6-dimethyl-1,4-pheny lene) ether, 9 parts triphenylphosphate, 0.15 parts zinc sulfide, 0.15 parts zinc oxide and 10 parts of a triblock copclymer 1 was extruded and molded. Another blend was also prepared, of the same composition except that the 10 parts of the triblock were replaced by a mixture of 5 parts of the triblock and 5 parts of EPDM rubber 2 , and a third with the 10 pares of the triblock replaced by 10 parts of EPDM. Properties of the blends are given in Table 3. The effect of replacing part or all of the triblock with EPDM is a slight increase in Izod impact and a slight decrease in Gardner impact strength.
- Example 4 Compositions of 78 parts of poly (2, 6-dimethyl-l , 4- phenylene) ether; 22 parts of triphenyl phosphate and 10 parts of the specified EPDM rubber were extruded and molded along with a control blend that did not contain anv EPDM rubber.
- Epcar 847 is a terpolymer of ethylene propylene and 5-ethyl- idene-2-norbornene containing about 65% ethylene, 30% propylene and 57. of 5-ethylidene-2-norbornene.
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3129767T DE3129767C2 (de) | 1980-01-14 | 1981-01-13 | Termoplastische Formmasse |
JP50353681A JPS58500763A (ja) | 1981-01-13 | 1981-05-19 | 皮革なめし剤及びその製法 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/111,983 US4315084A (en) | 1980-01-14 | 1980-01-14 | Polyphenylene ether molding compositions that include an alkenyl aromatic resin and EPDM rubber |
US111983 | 2005-04-22 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1981002019A1 true WO1981002019A1 (en) | 1981-07-23 |
Family
ID=22341495
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1981/000043 WO1981002019A1 (en) | 1980-01-14 | 1981-01-13 | Polyphenylene ether molding compositions that include an alkenyl aromatic resin and an epdm rubber |
Country Status (4)
Country | Link |
---|---|
US (2) | US4315084A (da) |
JP (1) | JPS6336346B2 (da) |
DE (1) | DE3129767C2 (da) |
WO (1) | WO1981002019A1 (da) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4483953A (en) * | 1981-10-28 | 1984-11-20 | General Electric Company | Polyphenylene ether resins and compositions heat stabilized with trineopentylene diphosphite |
US4442251A (en) * | 1982-03-04 | 1984-04-10 | General Electric Company | Impact resistant polyphenylene ether resin compositions |
US4910241A (en) * | 1983-08-25 | 1990-03-20 | General Electric Company | Crosslinkable flame retardant compositions of olefinic rubber and polyphenylene ether |
US4600741A (en) * | 1984-09-27 | 1986-07-15 | General Electric Company | Polyphenylene ether-polyamide blends |
US4678601A (en) * | 1985-09-16 | 1987-07-07 | The Dow Chemical Company | Electroconductive polymer-latex composites |
US5069818A (en) * | 1985-09-26 | 1991-12-03 | General Electric Company | Functionalized polyphenylene ethers and blends with polyamides |
US4824915A (en) * | 1985-09-26 | 1989-04-25 | General Electric Company | Functionalized polyphenylene ethers and blends with polyamides |
JPS62223252A (ja) * | 1986-03-25 | 1987-10-01 | Mitsubishi Rayon Co Ltd | ポリフエニレンエ−テル樹脂組成物 |
US5015690A (en) * | 1987-04-13 | 1991-05-14 | Copolymer Rubber & Chemical Corporation | Thermoplastic modifier compositions which imparts improved appearance and impact properties to molded thermoplastics |
JPH0545264Y2 (da) * | 1988-11-30 | 1993-11-18 | ||
JPH04178445A (ja) * | 1990-11-09 | 1992-06-25 | Mitsubishi Petrochem Co Ltd | 熱可塑性樹脂組成物 |
US6187425B1 (en) | 1996-12-30 | 2001-02-13 | Kimberly-Clark Worldwide, Inc. | Elastic materials with improved performance at body temperature |
US6011117A (en) * | 1997-02-11 | 2000-01-04 | Basf Corporation | High gloss, high impact polystyrene composition |
US6113822A (en) * | 1998-12-23 | 2000-09-05 | General Electric Company | Polyolefins as nucleating agent for foamed engineering polymers |
JP2004161929A (ja) * | 2002-11-14 | 2004-06-10 | Ge Plastics Japan Ltd | ワイヤ・ケーブル被覆材用樹脂組成物 |
US7517927B2 (en) * | 2004-01-07 | 2009-04-14 | Sabic Innovative Plastics Ip B.V. | Flexible poly(arylene ether)composition and articles thereof |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3383435A (en) * | 1965-01-06 | 1968-05-14 | Gen Eiectric Company | Blend of a polyphenylene ether and a styrene resin |
US3943191A (en) * | 1973-10-01 | 1976-03-09 | General Electric Company | Blends of a polyphenylene ether resin and alkenyl aromatic resins modified with EPDM rubber |
US3981841A (en) * | 1974-02-15 | 1976-09-21 | General Electric Company | Blends of a polyphenylene ether resin, alkenyl aromatic resins modified with EPDM rubber and graft polymerized high rubber content polymers |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4826381A (da) * | 1971-08-07 | 1973-04-06 | ||
JPS4838768A (da) * | 1971-09-17 | 1973-06-07 | ||
CS165110B1 (da) * | 1973-02-27 | 1975-11-28 | ||
US3981341A (en) * | 1975-05-19 | 1976-09-21 | The Goodyear Tire & Rubber Company | Safety support for pneumatic tires |
JPS53418A (en) * | 1976-06-25 | 1978-01-06 | Kahee Shimomura | Doubleewalled ocean tanks of caisson type with shaft |
DE2752383A1 (de) * | 1976-12-28 | 1978-06-29 | Gen Electric | Plastizierte verstaerkte zusammensetzungen aus einem polyphenylenaetherharz |
US4101503A (en) * | 1977-04-13 | 1978-07-18 | General Electric Company | Compositions of a polyphenylene ether resin and high molecular weight alkenyl aromatic resins modified with EPDM rubber |
US4101504A (en) * | 1977-04-13 | 1978-07-18 | General Electric Company | High impact compositions of a polyphenylene ether resin and alkenyl aromatic resins modified with EPDM rubber |
US4101505A (en) * | 1977-04-13 | 1978-07-18 | General Electric Company | Compositions of a polyphenylene ether resin and EPDM rubber-modified alkenyl aromatic resins having specified gel content |
US4196116A (en) * | 1977-11-28 | 1980-04-01 | General Electric Company | Impact resistant polyphenylene ether compositions containing EPDM rubber-modified alkenyl aromatic resins and hydrogenated diblock copolymers |
JPS54148840A (en) * | 1978-05-12 | 1979-11-21 | Gen Electric | Thermoplastic composition |
JPS54148836A (en) * | 1978-05-12 | 1979-11-21 | Gen Electric | Polyphenylene ether composition |
-
1980
- 1980-01-14 US US06/111,983 patent/US4315084A/en not_active Expired - Lifetime
-
1981
- 1981-01-13 DE DE3129767T patent/DE3129767C2/de not_active Expired - Fee Related
- 1981-01-13 WO PCT/US1981/000043 patent/WO1981002019A1/en active Application Filing
- 1981-01-13 JP JP56500697A patent/JPS6336346B2/ja not_active Expired
- 1981-08-14 US US06/292,747 patent/US4421883A/en not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3383435A (en) * | 1965-01-06 | 1968-05-14 | Gen Eiectric Company | Blend of a polyphenylene ether and a styrene resin |
US3943191A (en) * | 1973-10-01 | 1976-03-09 | General Electric Company | Blends of a polyphenylene ether resin and alkenyl aromatic resins modified with EPDM rubber |
US3981841A (en) * | 1974-02-15 | 1976-09-21 | General Electric Company | Blends of a polyphenylene ether resin, alkenyl aromatic resins modified with EPDM rubber and graft polymerized high rubber content polymers |
Also Published As
Publication number | Publication date |
---|---|
DE3129767T1 (de) | 1982-04-01 |
JPS6336346B2 (da) | 1988-07-20 |
JPS57500153A (da) | 1982-01-28 |
US4315084A (en) | 1982-02-09 |
DE3129767C2 (de) | 1995-03-02 |
US4421883A (en) | 1983-12-20 |
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