EP0678114A4 - - Google Patents
Info
- Publication number
- EP0678114A4 EP0678114A4 EP94906024A EP94906024A EP0678114A4 EP 0678114 A4 EP0678114 A4 EP 0678114A4 EP 94906024 A EP94906024 A EP 94906024A EP 94906024 A EP94906024 A EP 94906024A EP 0678114 A4 EP0678114 A4 EP 0678114A4
- Authority
- EP
- European Patent Office
- Prior art keywords
- polyphenylene sulfide
- composition according
- composition
- terpolymer
- group
- 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.)
- Withdrawn
Links
- 239000004734 Polyphenylene sulfide Substances 0.000 claims abstract description 85
- 229920000069 polyphenylene sulfide Polymers 0.000 claims abstract description 85
- 239000000203 mixture Substances 0.000 claims abstract description 79
- 229920001897 terpolymer Polymers 0.000 claims abstract description 44
- 150000001336 alkenes Chemical class 0.000 claims abstract description 31
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 31
- -1 acrylic ester Chemical group 0.000 claims abstract description 24
- 239000002253 acid Substances 0.000 claims abstract description 17
- 239000003365 glass fiber Substances 0.000 claims abstract description 15
- 239000003960 organic solvent Substances 0.000 claims abstract description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229920000049 Carbon (fiber) Polymers 0.000 claims abstract description 8
- 239000004917 carbon fiber Substances 0.000 claims abstract description 8
- 238000002156 mixing Methods 0.000 claims abstract description 8
- 229920000642 polymer Polymers 0.000 claims abstract description 8
- 239000012744 reinforcing agent Substances 0.000 claims abstract description 6
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 15
- 239000000654 additive Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 8
- 230000000996 additive effect Effects 0.000 claims description 7
- 239000000945 filler Substances 0.000 claims description 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 6
- 239000005977 Ethylene Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000000835 fiber Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical group C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 claims description 3
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical group CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000006057 Non-nutritive feed additive Substances 0.000 claims description 2
- 239000004760 aramid Substances 0.000 claims description 2
- 229920006231 aramid fiber Polymers 0.000 claims description 2
- 239000011324 bead Substances 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- 239000000919 ceramic Substances 0.000 claims description 2
- 239000010439 graphite Substances 0.000 claims description 2
- 229910002804 graphite Inorganic materials 0.000 claims description 2
- 150000002430 hydrocarbons Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000000314 lubricant Substances 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052982 molybdenum disulfide Inorganic materials 0.000 claims description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 2
- 229920001296 polysiloxane Polymers 0.000 claims description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 2
- 150000004760 silicates Chemical class 0.000 claims description 2
- 230000003068 static effect Effects 0.000 claims description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 2
- 239000011521 glass Substances 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 239000012763 reinforcing filler Substances 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 11
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 8
- 229920000728 polyester Polymers 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- CGPRUXZTHGTMKW-UHFFFAOYSA-N ethene;ethyl prop-2-enoate Chemical compound C=C.CCOC(=O)C=C CGPRUXZTHGTMKW-UHFFFAOYSA-N 0.000 description 5
- 239000011159 matrix material Substances 0.000 description 5
- 239000004952 Polyamide Substances 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- 229920001169 thermoplastic Polymers 0.000 description 4
- 239000004416 thermosoftening plastic Substances 0.000 description 4
- 239000002131 composite material Substances 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- 229920013683 Celanese Polymers 0.000 description 2
- 229920013633 Fortron Polymers 0.000 description 2
- 239000004738 Fortron® Substances 0.000 description 2
- 229920013632 Ryton Polymers 0.000 description 2
- 239000004736 Ryton® Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 230000002787 reinforcement Effects 0.000 description 2
- 239000012745 toughening agent Substances 0.000 description 2
- WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical class [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
- 235000011132 calcium sulphate Nutrition 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- BLCTWBJQROOONQ-UHFFFAOYSA-N ethenyl prop-2-enoate Chemical compound C=COC(=O)C=C BLCTWBJQROOONQ-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical class [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 235000011160 magnesium carbonates Nutrition 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
Classifications
-
- 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
- C08L81/02—Polythioethers; Polythioether-ethers
-
- 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
-
- 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
Definitions
- the present invention relates to toughened polyphenylene sulfide compositions for mechanical and industrial applications and, more particularly, to toughening polyphenylene sulfide compositions to enhance impact strength, weld line strength and tensile elongation.
- Polyphenylene sulfide is a semicrystalline, high temperature resistant material which is used in many industrial and mechanical applications.
- Polyphenylene sulfide is often used for mechanical parts, such as gears, motor parts, furnace components, lighting sockets and electrical connectors.
- Automotive parts such as engine sensors and light reflectors can also be made from polyphenylene sulfide materials.
- Polyphenylene sulfide suffers from low impact strength, poor weld line strength and a tendency to flash when injection molded.
- various attempts in the prior art to toughen various thermoplastics including polyphenylene sulfide.
- U.S. Patent No. 4,172,859 discloses a toughened multi-phase thermoplastic composition consisting essentially of 60 to 99 wt% of a polyester and polycarbonate matrix resin and 1 to 40 wt% of at least one random copolymer having a particle size of 0.01 to 3 microns adhered to the matrix resin.
- Suitable copolymers for toughening the polyester/polycarbonate matrix include ethylene/vinyl acetate/glycidyl methacrylate and ethylene/methyl acrylate/glycidyl methacrylate.
- the compositions may be modified by one or more conventional additives, such as fibrous and particulate fillers and reinforcements, etc.
- the compositions are useful for forming molded and extruded parts having greater ductility, toughness and less susceptibility to catastrophic failure.
- U.S. Patent No. 4,174,358 discloses a toughened thermoplastic composition consisting essentially of 60 to 99 wt% of a polyamide matrix resin and 1 to 40 wt% of at least one polymer- having a particle size of 0.01 to 3 microns and being adhered to the polyamide.
- An example of a suitable toughening polymer is ethylene/vinyl acrylate/glycidyl methacrylate. Similar advantages were observed for the toughened polyamide compositions as those observed for the toughened polyester/polycarbonate compositions previously discussed.
- U.S. Patent No. 4,753,980 discloses toughened thermoplastic polyester compositions comprising 60 to 97 wt% of a polyester matrix resin and 3 to 40 wt% of an ethylene copolymer, such as ethylene/methyl acrylate/glycidyl methacrylate. Molded articles formed from the toughened polyester compositions are characterized by extraordinary toughness, especially at low temperatures. With regard to the prior art discussed above, it is believed that a terpolymer such as ethylene/methyl acrylate/glycidyl methacrylate reacts with the amine of the polyamide or carboxyl groups of the polyester. However, no similar reactivity is apparent with polyphenylene sulfide compositions.
- U.S. Patent No. 4,889,893 discloses a polyphenylene sulfide composition having enhanced impact properties comprising: (a) a polyphenylene sulfide resin which is treated with an acid, hot water or an organic solvent or combination thereof; and (b) an olefinic copolymer containing 60 to 99.5 wt% of an s -olefin and 0.5 to 40 wt% of a glycidyl ester of an , ⁇ -unsaturated carboxylic acid.
- the polyphenylene sulfide must be treated with the acid, hot water and/or organic solvent to increase its affinity with the olefinic copolymer.
- Suitable olefinic copolymers include ethylene, propylene and butene-1.
- Suitable glycidyl esters of acids include glycidyl acrylate, methacrylate a d ethacrylate.
- the olefinic copolymer »ay further be copolymerized with 40 wt% or less of another copolymerizable unsaturated monomer, such as vinyl ether, vinyl acetate, vinyl propionate, methyl acrylate, methyl methacrylate, acrylonitrile or styrene.
- the polyphenylene sulfide composition comprises a blend of (a) polyphenylene sulfide which has not been pretreated with an acid, hot water or organic solvent wash; and (b) an olefin terpolymer for toughening the polyphenylene sulfide, the terpolymer having the formula:
- the composition may optionally include conventional additives such as fillers or reinforcing agents.
- Another aspect of the present invention is a method for toughening a polyphenylene sulfide composition.
- the method comprises blending polyphenylene sulfide and an olefin terpolymer of the Formula I, with no acid, hot water or organic solvent wash pretreatment of the polyphenylene sulfide.
- the invention is particularly advantageous for toughening glass or carbon fiber reinforced polyphenylene sulfide compositions.
- the toughened polyphenylene sulfide compositions of the present invention not only exhibit high impact strength, weld line strength and tensile elongation, but also have improved color stability during extrusion and molding operations and are believed to have improved wear resistance over polyphenylene sulfide alone.
- the need for an acid wash or other pretreatment of the polyphenylene sulfide is eliminated in the present compositions, thereby providing a simple and inexpensive method for making toughened polyphenylene sulfide compositions.
- the toughened polyphenylene sulfide composition of the present invention comprises polyphenylene sulfide which has not been pretreated with an acid wash, hot water and/or organic solvent to improve its affinity with the olefinic terpolymer.
- the polyphenylene sulfide may be of a branch configuration, a linear configuration is presently preferred.
- An example of a suit-able linear polyphenylene sulfide resin is Fortron 214, which is commercially available from Hoechst Celanese Corp. of Chatham, New Jersey.
- a branched polyphenylene sulfide which is suitable for use in the present invention is Ryton P4, which is commercially available from Phillips 66 Co. of Pasadena, Texas.
- the percentage of polyphenylene sulfide in the unfilled or unreinforced composition is about 60 to about 97 wt%. However, it is presently preferred that the percentage of polyphenylene sulfide in the composition be about 70 to about 96 wt% and, more preferably, about 80 to about 93 wt%.
- the toughening agent for the polyphenylene sulfide composition comprises an olefin terpolymer represented by the formula:
- the component E is an olefinic polymer, such as ethylene, propylene, butene or pentene.
- the percentage of the olefinic polymer in the olefin terpolymer is about 40 to about 90 wt%.
- the percentage of olefinic polymer is about 50 to about 80 wt% and, more preferably, about 60 to about 70 wt% of the total terpolymer.
- the component X of the olefin terpolymer is an acrylic ester.
- the acrylic ester is preferably one having the general formula:
- R is selected from the group consisting of H and a lower alkyl group and R' is a hydrocarbon group having 1 to 8 and preferably 1 to 4 carbons.
- the lower alkyl group has 1 to 6, and preferably 1 to 3 carbons.
- suitable acrylic esters include ethyl acrylate and butyl acrylate.
- the percentage of the component X in the olefin terpolymer is generally about 15 to about 40 wt%. However, it is presently preferred that the percentage of X is about 20 to about 35 wt% and, more preferably, about 25 to about 32 wt% of the total terpolymer.
- the component Y of the olefin terpolymer is a glycidyl ester.
- the glycidyl ester is one having the general formula:
- ⁇ C C-CII-0-CI-CI - C/ (III) / I I ⁇ / ⁇
- the component Y comprises about 1 to about 20 wt% of the olefin terpolymer.
- the component Y comprises about 3 to about 16 wt% and, more preferably, about 5 to about 9 wt% of the olefin terpolymer.
- Suitable olefin terpolymers are commercially available or may be polymerized according to methods well known to those of ordinary skill in the art.
- the olefin terpolymers suitable for use in the present invention is an ethylene/ethyl acrylate/glycidyl methacrylate terpolymer which is commercially available from Elf Atochem North America, Inc. of Philadelphia, Pennsylvania under the trademark Lotader.
- the terpolymer to be blended with the polyphenylene sulfide is in powdered or pelletized form.
- the polyphenylene sulfide and olefin terpolymer may be blended by dry tumbling and mixing in a single screw extruder having a mixing screw design, for example.
- a suitable single screw extruder for use in the present invention is commercially available from Welex of Blue Bell, Pennsylvania.
- Other methods for blending the polyphenylene sulfide and olefin terpolymer will be evident to those of ordinary skill in the art.
- the toughened polyphenylene sulfide composition may also include additives such as reinforcing agents, fillers, lubricants, static dissipating materials, and/or processing aids.
- Suitable additives include polytetrafluoroethylene; silicone; molybdenum disulfide; polyethylene; carbon fiber or powder; glass fiber, powder or beads; silicon carbide fibers; aramid fibers; ceramic fibers; graphite fibers or powder; metal fibers; and fillers, such as silicates, mica, talc, wollastonite, clay, carbonates, such as calcium and magnesium carbonates, and sulfates, such as barium and calcium sulfates.
- the additive(s) in the polyphenylene sulfide composition may be present in an amount up to about 80 wt% of the total composition. Preferably the percentage of additive is about 30 to about 60 wt% of the composition.
- glass fibers to the present polyphenylene sulfide composition, which increases the. strength, stiffness, creep resistance, thermoconductivity and heat distortion temperature of the composition.
- Carbon fibers may be added to the polyphenylene sulfide composition to increase the strength, thermocon ⁇ ductivity, electrical conductivity, and creep and fatigue endurance of the composition.
- the additive is mixed with the composition after the polyphenylene sulfide and olefin terpolymer have been blended, but each of the components may be blended together and extruded as discussed above, as desired.
- the toughened polyphenylene sulfide compositions of the present invention may be used in the same types of applications as polyphenylene sulfide alone, and are especially advantageous where enhanced toughness, high impact strength, weld line strength and tensile elongation are desired.
- the present invention will now be illustrated by the following specific, non-limiting examples.
- EXAMPLE 1 Polyphenylene sulfide and olefin terpolymer composites were prepared by dry tumbling varying percentages of linear polyphenylene sulfide (Hoechst Celanese) and ethylene/ethyl acrylate/glycidyl methacrylate (E/EA/GMA) (Atochem) to form compositions according to the present invention. No acid, hot water, organic solvent or other pretreatment of the PPS was used. Glass fibers (GF) (1/8" x 10 um, which are commercially available from PPG Industries, Inc. of Pittsburgh, Pennsylvania) were blended together with the polyphenylene sulfide and olefin terpolymer at different percentages.
- GF glass fibers
- compositions were extruded in a 2 1/2" single screw extruder having a mixing screw design. Percentages of toughening agent and glass fiber reinforcement present in each test sample are set forth in Table I.
- Table I As shown in Table I, as the weight percentage of ethylene/ethyl acrylate/glycidyl methacrylate is progressively increased in samples having the same percentage of glass fiber, the notched Izod values also increase. For example, for 30 wt% glass fiber samples, the notched Izod value almost tripled when 20 wt% ethylene/ethyl acrylate/glycidyl methacrylate was included in the polyphenylene sulfide composition. Similar increases in notched Izod strength values were observed for samples containing 40 and 50 wt% glass fiber, respectively.
- EXAMPLE 2 Polyphenylene sulfide and olefin terpolymer composites were prepared in the same manner using the same components as Example 1, except 40 wt% glass fiber and 8.5 wt% carbon fiber were included in each sample. No acid, hot water, organic solvent or other pretreatment of the PPS was used. Test samples of each composite were prepared and tested in the same manner as that set forth in Example 1. The test results are set forth in Table II.
- the test results show that the olefin terpolymers of the present invention enhance the toughness and strength of polyphenylene sulfide compositions without acid, hot water or organic solvent treatment of the polyphenylene sulfide prior to compounding.
- the use of an olefin terpolymer according to the present invention not only increases the impact strength of polyphenylene sulfide, but also the weld line strength and tensile elongation. It is also believed that the olefin terpolymer improves the color stability of polyphenylene sulfide compositions of the present invention during extrusion and molding and the wear resistance of articles formed from the compositions.
Landscapes
- 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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US228793A | 1993-01-08 | 1993-01-08 | |
| US2287 | 1993-01-08 | ||
| PCT/US1994/000103 WO1994016018A1 (en) | 1993-01-08 | 1994-01-04 | Toughened polyphenylene sulfide compositions and method of making the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0678114A1 EP0678114A1 (en) | 1995-10-25 |
| EP0678114A4 true EP0678114A4 (enrdf_load_stackoverflow) | 1995-12-06 |
Family
ID=21700082
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP94906024A Withdrawn EP0678114A1 (en) | 1993-01-08 | 1994-01-04 | Toughened polyphenylene sulfide compositions and method of making the same |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0678114A1 (enrdf_load_stackoverflow) |
| JP (1) | JPH08506128A (enrdf_load_stackoverflow) |
| AU (1) | AU5991094A (enrdf_load_stackoverflow) |
| BR (1) | BR9405652A (enrdf_load_stackoverflow) |
| CA (1) | CA2153328A1 (enrdf_load_stackoverflow) |
| WO (1) | WO1994016018A1 (enrdf_load_stackoverflow) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011012139A (ja) * | 2009-06-30 | 2011-01-20 | Tosoh Corp | ポリアリーレンスルフィド組成物 |
| KR101368315B1 (ko) * | 2010-12-31 | 2014-02-27 | 제일모직주식회사 | 밀드 피치계 탄소섬유를 포함하는 고열전도성 수지 조성물 |
| KR101355472B1 (ko) * | 2010-12-31 | 2014-01-28 | 제일모직주식회사 | 고열전도성 수지 조성물 |
| US9765219B2 (en) | 2012-04-13 | 2017-09-19 | Ticona Llc | Polyarylene sulfide components for heavy duty trucks |
| US9758674B2 (en) | 2012-04-13 | 2017-09-12 | Ticona Llc | Polyarylene sulfide for oil and gas flowlines |
| US9493646B2 (en) | 2012-04-13 | 2016-11-15 | Ticona Llc | Blow molded thermoplastic composition |
| US9494260B2 (en) | 2012-04-13 | 2016-11-15 | Ticona Llc | Dynamically vulcanized polyarylene sulfide composition |
| US9494262B2 (en) | 2012-04-13 | 2016-11-15 | Ticona Llc | Automotive fuel lines including a polyarylene sulfide |
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| WO2015031233A1 (en) | 2013-08-27 | 2015-03-05 | Ticona Llc | Heat resistant toughened thermoplastic composition for injection molding |
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| CN104817831A (zh) * | 2015-05-21 | 2015-08-05 | 国网智能电网研究院 | 一种电气绝缘热塑性树脂组合物及其制备方法 |
| WO2017100395A1 (en) | 2015-12-11 | 2017-06-15 | Ticona Llc | Crosslinkable polyarylene sulfide composition |
| CN108368339A (zh) | 2015-12-11 | 2018-08-03 | 提克纳有限责任公司 | 聚芳硫醚组合物 |
| CN108883600B (zh) | 2016-03-24 | 2021-08-06 | 提克纳有限责任公司 | 复合结构体 |
| JP6987183B1 (ja) * | 2020-06-29 | 2021-12-22 | ポリプラスチックス株式会社 | 押出成形又はブロー成形用ポリアリーレンサルファイド樹脂組成物 |
| CN112724675A (zh) * | 2020-12-29 | 2021-04-30 | 富海(东营)新材料科技有限公司 | 一种聚苯硫醚复合材料及其制备方法 |
| CN112778762B (zh) * | 2020-12-31 | 2023-01-10 | 上海聚威新材料股份有限公司 | 一种导电pps复合材料及其制备方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0484273A1 (de) * | 1990-10-08 | 1992-05-06 | Ciba-Geigy Ag | Polyarylensulfidzusammensetzungen |
| JPH04332735A (ja) * | 1991-05-08 | 1992-11-19 | Toray Ind Inc | ブロー中空成形品 |
| EP0546608A1 (fr) * | 1991-12-13 | 1993-06-16 | SOLVAY (Société Anonyme) | Compositions à base de polysulfure de phénylène de résistance au choc améliorée et procédé pour les préparer |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0228268B1 (en) * | 1985-12-27 | 1990-05-23 | Toray Industries, Inc. | A polyphenylene sulfide resin composition and a process for producing it |
| JPH0662849B2 (ja) * | 1988-02-03 | 1994-08-17 | ポリプラスチックス株式会社 | ポリアリーレンサルファイド樹脂組成物 |
| JPH01306467A (ja) * | 1988-06-02 | 1989-12-11 | Toray Ind Inc | ポリフェニレンスルフィド組成物 |
| US5204405A (en) * | 1988-11-09 | 1993-04-20 | Nippon Petrochemicals Co., Ltd. | Thermoplastic resin composition and method for preparing the same |
-
1994
- 1994-01-04 AU AU59910/94A patent/AU5991094A/en not_active Withdrawn
- 1994-01-04 JP JP6516159A patent/JPH08506128A/ja active Pending
- 1994-01-04 WO PCT/US1994/000103 patent/WO1994016018A1/en not_active Application Discontinuation
- 1994-01-04 CA CA 2153328 patent/CA2153328A1/en not_active Abandoned
- 1994-01-04 EP EP94906024A patent/EP0678114A1/en not_active Withdrawn
- 1994-01-04 BR BR9405652A patent/BR9405652A/pt not_active Application Discontinuation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0484273A1 (de) * | 1990-10-08 | 1992-05-06 | Ciba-Geigy Ag | Polyarylensulfidzusammensetzungen |
| JPH04332735A (ja) * | 1991-05-08 | 1992-11-19 | Toray Ind Inc | ブロー中空成形品 |
| EP0546608A1 (fr) * | 1991-12-13 | 1993-06-16 | SOLVAY (Société Anonyme) | Compositions à base de polysulfure de phénylène de résistance au choc améliorée et procédé pour les préparer |
Non-Patent Citations (2)
| Title |
|---|
| PATENT ABSTRACTS OF JAPAN vol. 017, no. 176 (C - 1045) 6 April 1993 (1993-04-06) * |
| See also references of WO9416018A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH08506128A (ja) | 1996-07-02 |
| BR9405652A (pt) | 1995-11-14 |
| AU5991094A (en) | 1994-08-15 |
| WO1994016018A1 (en) | 1994-07-21 |
| EP0678114A1 (en) | 1995-10-25 |
| CA2153328A1 (en) | 1994-07-21 |
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