WO2006037753A1 - Sulfone polymer composition - Google Patents
Sulfone polymer composition Download PDFInfo
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- WO2006037753A1 WO2006037753A1 PCT/EP2005/054934 EP2005054934W WO2006037753A1 WO 2006037753 A1 WO2006037753 A1 WO 2006037753A1 EP 2005054934 W EP2005054934 W EP 2005054934W WO 2006037753 A1 WO2006037753 A1 WO 2006037753A1
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- WIPO (PCT)
- Prior art keywords
- polymer
- sulfone
- recurring units
- immiscible
- composition according
- Prior art date
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 155
- 239000000203 mixture Substances 0.000 title claims abstract description 68
- 150000003457 sulfones Chemical class 0.000 title claims abstract description 68
- 230000009477 glass transition Effects 0.000 claims abstract description 31
- 238000000034 method Methods 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- 239000004697 Polyetherimide Substances 0.000 claims description 11
- 229920001601 polyetherimide Polymers 0.000 claims description 11
- 229920006393 polyether sulfone Polymers 0.000 claims description 8
- 239000004695 Polyether sulfone Substances 0.000 claims description 7
- 229920002492 poly(sulfone) Polymers 0.000 claims description 7
- 239000004696 Poly ether ether ketone Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229920002530 polyetherether ketone Polymers 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 150000003949 imides Chemical class 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 229920005649 polyetherethersulfone Polymers 0.000 claims description 3
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 238000012360 testing method Methods 0.000 description 9
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 8
- 238000013329 compounding Methods 0.000 description 7
- 239000000835 fiber Substances 0.000 description 6
- 238000010998 test method Methods 0.000 description 5
- 229920000491 Polyphenylsulfone Polymers 0.000 description 4
- 229920003295 Radel® Polymers 0.000 description 4
- 238000001746 injection moulding Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000006068 polycondensation reaction Methods 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229920001400 block copolymer Polymers 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000012763 reinforcing filler Substances 0.000 description 3
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229920004738 ULTEM® Polymers 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 239000002216 antistatic agent Substances 0.000 description 2
- JUPQTSLXMOCDHR-UHFFFAOYSA-N benzene-1,4-diol;bis(4-fluorophenyl)methanone Chemical compound OC1=CC=C(O)C=C1.C1=CC(F)=CC=C1C(=O)C1=CC=C(F)C=C1 JUPQTSLXMOCDHR-UHFFFAOYSA-N 0.000 description 2
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 239000012760 heat stabilizer Substances 0.000 description 2
- -1 herein after) Substances 0.000 description 2
- 239000001023 inorganic pigment Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 238000003754 machining Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 239000012860 organic pigment Substances 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000012744 reinforcing agent Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- OZUNPRDEUXITBO-UHFFFAOYSA-N 1-(4-chlorophenyl)sulfonyl-4-[4-(4-chlorophenyl)sulfonylphenyl]benzene Chemical group C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC=C(C=2C=CC(=CC=2)S(=O)(=O)C=2C=CC(Cl)=CC=2)C=C1 OZUNPRDEUXITBO-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- XIAJWWWCYMMOMV-UHFFFAOYSA-N CC(C)(c(cc1)ccc1OC)c(cc1)ccc1Oc(cc1)ccc1S(c1ccc(C)cc1)(=O)=O Chemical compound CC(C)(c(cc1)ccc1OC)c(cc1)ccc1Oc(cc1)ccc1S(c1ccc(C)cc1)(=O)=O XIAJWWWCYMMOMV-UHFFFAOYSA-N 0.000 description 1
- 0 CC(C1N2)[C@]1C2=*C Chemical compound CC(C1N2)[C@]1C2=*C 0.000 description 1
- 229920004695 VICTREX™ PEEK Polymers 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 229920005603 alternating copolymer Polymers 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229940106691 bisphenol a Drugs 0.000 description 1
- 238000000071 blow moulding Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- NJLLQSBAHIKGKF-UHFFFAOYSA-N dipotassium dioxido(oxo)titanium Chemical compound [K+].[K+].[O-][Ti]([O-])=O NJLLQSBAHIKGKF-UHFFFAOYSA-N 0.000 description 1
- NLLGJEMIZSAJFN-AAFOHLTDSA-L disodium;(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxy-1-[4-[4-[[(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxy-1-sulfonatohexyl]amino]phenyl]sulfonylanilino]hexane-1-sulfonate Chemical compound [Na+].[Na+].C1=CC(NC([C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO)S([O-])(=O)=O)=CC=C1S(=O)(=O)C1=CC=C(NC([C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO)S([O-])(=O)=O)C=C1 NLLGJEMIZSAJFN-AAFOHLTDSA-L 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 238000010330 laser marking Methods 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000012764 mineral filler Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000003856 thermoforming Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
- 239000011787 zinc oxide Substances 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
- C08L81/06—Polysulfones; Polyethersulfones
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/0313—Organic insulating material
- H05K1/032—Organic insulating material consisting of one material
- H05K1/0333—Organic insulating material consisting of one material containing S
Definitions
- the invention relates to a sulfone polymer composition having a good balance between high temperature performances, melt processability and economic aspects.
- High glass transition temperature sulfone polymers are attractive because of their outstanding heat resistance, dimensional stability, good chemical resistance and mechanical integrity up to operating temperature of about 250°C.
- a sulfone polymer composition comprising : - at least one high glass transition temperature sulfone polymer (A)
- the sulfone polymer composition of the invention possesses advantageously thermal performances and processability advantages in addition to minor cost with respect to high glass transition temperature sulfone polymers.
- polymer is intended to denote any material consisting essentially of recurring units, and having a molecular weight above 2000.
- high glass transition temperature sulfone polymer (A) is intended to denote any polymer, at least 50 % wt of the recurring units thereof being recurring units (Rl) :
- - Q is a group chosen among the following structures
- J J J J J J J VY lUl n integer from 1 to 6, or an aliphatic divalent group, linear or branched, of up to 6 carbon atoms; and mixtures thereof.
- recurring units (Rl) are recurring units (ii).
- Polymer (A) may notably be a homopolymer or a copolymer. Should polymer (A) be a copolymer, it may notably be a random, alternating or block copolymer. Although polymer (A) may be a block copolymer in certain particular embodiments of the invention, polymer (A) is generally not a block copolymer.
- the high glass temperature sulfone polymer (A) comprises preferably 70 % wt, more preferably 75 % wt of recurring units (Rl); still more preferably, it contains no recurring unit other than recurring units (Rl). Excellent results were obtained with high glass transition temperature sulfone polymer (A) consisting of recurring units (ii) (polybiphenyldisulfone, hereinafter).
- the term "at least one high transition temperature solfone polymer (A)” means that the polymer composition can comprise one or more than one polymer (A). Should the composition comprise several polymers (A), said polymers (A) are usually miscible, that implies that they display only one glass transition temperature.
- the high glass transition temperature sulfone polymer (A) has a glass transition temperature advantageously of at least 230°C, preferably of at least 240°C, more preferably of at least 250°C.
- the sulfone polymer composition advantageously comprises at least 20 % wt, preferably at least 40 % wt, more preferably at least 50 % wt of high glass transition temperature sulfone polymer (A), with respect to the total weight Of (A) 5 (B) and (C).
- the sulfone polymer composition advantageously comprises at most 90 % wt, preferably at most 80 % wt, more preferably at most 75 % wt of high glass transition temperature sulfone polymer (A), with respect to the total weight Of (A) 5 (B) and (C).
- miscible polymer (B) is intended to denote any polymer miscible with the high glass temperature sulfone polymer (A) in the composition according to the invention, i.e. a polymer yielding a single homogeneous phase when mixed with said high glass temperature sulfone polymer (A), showing only one glass transition temperature.
- the miscible polymer (B) is a miscible sulfone polymer.
- miscible sulfone polymer is intended to denote any polymer, at least 50 % wt of the recurring units thereof being recurring units
- R being an aliphatic divalent group of up to 6 carbon atoms, such as methylene, ethylene, isopropylene and the like.
- Recurring units (R2) are preferably chosen from :
- recurring units (R2) are recurring units (j).
- the miscible sulfone polymer comprises generally more than 50 % wt, preferably 70 % wt, more preferably 75 % wt of recurring units (R2). Still more preferably, it contains no recurring unit other than recurring units (R2).
- miscible sulfone polymer the recurring units thereof are recurring units (j) (polyphenylsulfone, hereinafter).
- Polyphenylsulfone is available as RADEL ® R PPSF from Solvay Advanced Polymers, L.L.C..
- the sulfone polymer composition advantageously comprises at least 5 % wt, preferably at least 7.5 % wt, more preferably at least 10 % wt of miscible polymer (B), with respect to the total weight of (A), (B) and (C).
- the sulfone polymer composition advantageously comprises at most 60 % wt, preferably at most 50 % wt, more preferably at least 40 % wt of miscible polymer (B), with respect to the total weight of (A), (B) and (C).
- the term "immiscible polymer” is intended to denote any polymer immiscible with the high glass transition temperature sulfone polymer (A) in the composition according to the invention, i.e. a polymer yielding a phase-separated mixture when mixed with said high glass transition temperature sulfone polymer (A) or with the mixture of (A) and (B), showing two distinct glass transition temperatures.
- One typical feature obtained by adding said immiscible polymer (C) to components (A) and (B) is thus that, since the high glass transition temperature sulfone polymer (A) [and the mixture of (A) and (B)] and the immiscible polymer are phase separated, they retain their separate glass transition temperatures.
- the immiscible polymer (C) has a glass transition temperature of advantageously at least 150°C, preferably at least 160°C, more preferably at least 175°C.
- the immiscible polymer (C) has a glass transition temperature of advantageously at most 240°C, preferably at most 235°C, more preferably at most 230°C.
- the immiscible polymer (C) is selected from the group consisting of immiscible sulfone polymers, polyetherimide polymers, polyetheretherketone polymers (PEEK, herein after), and mixtures thereof.
- the term "immiscible sulfone polymer” is intended to denote any polymer, at least 50 % wt of the recurring units thereof being recurring units (R3), chosen from :
- Polysulfone is available as UDEL ® PSF from Solvay Advanced Polymers, L.L.C..
- Polyethersulfone is available as RADEL ® A PES from Solvay Advanced Polymers, L.L.C..
- the immiscible sulfone polymer comprises preferably 70 % wt, more preferably 75 % wt of recurring units (R3). Still more preferably, it contains no recurring unit other than recurring units (R3).
- polyetherimide polymer is intended to denote any polymer, at least 50 % wt of the recurring units thereof being recurring units (R4), comprising two imide groups as such (R4-A) and/or in their corresponding amic acid forms [(R4-B) and (R4-C)] :
- linking groups being in ortho, meta or para position and R' being a hydrogen atom or an alkyl radical comprising from 1 to 6 carbon
- n integer from 1 to 6 ;
- n integer from 1 to 6 .
- Recurring units (R4) are preferably recurring units (k), in imide (k-A) and/or in amic acid form [(k-B) and (k-C)] :
- the polyetherimide polymer comprises advantageously at least 50 % wt, preferably 70 % wt, more preferably 75 % wt of recurring units (R4), still more preferably, it contains no recurring unit other than recurring units (R4).
- polyetherimide polymer consisting of recurring units (k).
- Polymers available as ULTEM ® PEI from GE Plastics comply with this criterion.
- polyetherether ketone polymer is intended to denote any polymer, at least 50 % wt of the recurring units thereof being recurring units (R5) :
- the polyetheretherketone polymer comprises advantageously at least 50 % wt, preferably 70 % wt, more preferably 75 % wt of recurring units (R5), still more preferably, it contains no recurring unit other than recurring units (R5).
- the sulfone polymer composition advantageously comprises at least 5 % wt, preferably at least 7.5 % wt, more preferably at least 10 % wt of immiscible polymer (C), with respect to the total weight of (A), (B) and (C).
- the sulfone polymer composition advantageously comprises at most 60 % wt, preferably at most 50 % wt, more preferably at least 40 % wt of immiscible polymer (C), with respect to the total weight of (A), (B) and (C).
- the immiscible polymer (C) is an immiscible sulfone polymer selected from the group consisting of poly sulfone, polyethersulfone, polyetherethersulfone and mixtures thereof. More preferably, the component (C) of the first embodiment of the invention is chosen among the group consisting of polyethersulfone, polysulfone and mixtures thereof.
- the immiscible polymer (C) is a polyetherimide polymer. More preferably, the component (C) of the first embodiment of the invention is a polyetherimide polymer consisting of recurring units (k).
- the sulfone polymer composition can further comprise lubricating agents, heat stabilizer, anti-static agents, extenders, reinforcing agents, organic and/or inorganic pigments like TiO 2 , carbon black, acid scavengers, such as MgO, stabilizers, i.e., metal oxides such as zinc oxide, antioxidants, flame retardants, smoke-suppressing agents.
- lubricating agents heat stabilizer, anti-static agents, extenders, reinforcing agents, organic and/or inorganic pigments like TiO 2 , carbon black, acid scavengers, such as MgO, stabilizers, i.e., metal oxides such as zinc oxide, antioxidants, flame retardants, smoke-suppressing agents.
- the sulfone polymer composition optionally comprises at least one filler chosen from reinforcing fillers, structural fibers and mixtures thereof.
- Structural fibers may include glass fiber, carbon or graphite fibers, and fibers formed of silicon carbide, alumina, titania, boron and the like, and may include mixtures comprising two or more such fibers.
- Reinforcing fillers which can also be used in sulfone polymer composition include notably pigments, flake, spherical and fibrous particulate filler reinforcements and nucleating agents such as talc, mica, titanium dioxide, potassium titanate, silica, kaolin, chalk, alumina, mineral fillers, and the like.
- the reinforcing fillers and structural fibers can be used alone or in any combination.
- Another aspect of the present invention concerns a process for manufacturing the sulfone polymer composition as above described, which comprises mixing the at least one high glass transition temperature sulfone polymer (A), the at least one miscible polymer (B), and the at least one immiscible polymer (C).
- the process comprises mixing by dry blending and/or melt compounding the high glass transition temperature sulfone polymer (A), the miscible polymer (B), and the immiscible polymer (C).
- the high glass transition temperature sulfone polymer (A), the miscible polymer (B), and the immiscible polymer (C) are mixed by melt compounding.
- the high glass transition temperature sulfone polymer (A), the miscible polymer (B), and the immiscible polymer (C) are melt compounded in continuous or batch devices. Such devices are well-known to those skilled in the art.
- Suitable continuous devices to melt compound the sulfone polymer composition of the invention are notably screw extruders.
- the high glass transition temperature sulfone polymer (A), the miscible polymer (B), and the immiscible polymer (C) and optionally, other ingredients are advantageously fed in powder or granular form in an extruder and the sulfone polymer composition is advantageously extruded into strands and the strands are advantageously chopped into pellets.
- fillers may be added to the composition during the compounding step.
- the high glass transition temperature sulfone polymer (A), the miscible polymer (B), and the immiscible polymer (C) are melt compounded in a twin-screw extruder.
- the sulfone polymer composition can be processed following standard methods for injection molding, extrusion, thermoforming, machining, and blow molding. Solution-based processing for coatings and membranes is also possible. Finished articles comprising the sulfone polymer composition can undergo standard post-iabrication operations such as ultrasonic welding, adhesive bonding, and laser marking as well as heat staking, threading, and machining.
- an object of the invention is an article comprising the sulfone polymer composition as above described.
- the article is an injection molded article, an extrusion molded article, a shaped article, a coated article or a casted article.
- articles are shaped article, electronic components (such as printed circuit boards, electrical plug- in connectors, bobbins for relays and solenoids), pipes, fittings, housings, films, membranes, coatings.
- the articles according to the invention can be fabricated by processing the sulfone polymer composition as above described following standard methods.
- RADEL ® R-5800 NT polyphenylsulfone commercially available from Solvay Advanced Polymers, L.L.C., a sulfone polymer obtained from the poly condensation of a 4,4'-dihalodiphenylsulfone and 4,4'-dihydroxydiphenyl, has been used.
- Table 2 here below summarizes main properties of the material used in preparing the compositions : Table 2 - Properties of the polyphenylsulfone
- RADEL ® A-301 NT polyethersulfone commercially available from Solvay Advanced Polymers, L.L.C., a polyethersulfone polymer obtained from the poly condensation of a 4,4'-dihalodiphenylsulfone and
- compositions were melt compounded using a 25 mm diameter twin screw double vented Berstorff extruder having an L/D ratio of 33/1 according to the conditions profile shown in Table 4.
- the first vent port was open to the atmosphere; the second was connected to a vacuum pump.
- the extruder was fitted with a double strand die.
- the polymer extrudate was pelletized after passing through a water trough for cooling. All blends were extruded and pelletized without incident at the throughput rates indicated in Table 4.
- the resin pellets from the various resins and compositions were dried for about 16 hrs in a 149°C (300 F) desiccated hot air oven with a due point of -37.2°C (-35 F). Parts were then injection molded into 1/8" thick ASTM tensile and flexural test specimens using a Wasp Mini-Jector benchtop injection molding machine equipped with a 3/4" general purpose screw and a 20 L/D. Injection molding machine temperature settings were 395°C, 400°C and 405 °C for the rear, front and nozzle sections respectively. An injection pressure of 1100 psi was used along with a mold temperature of 85°C (185 F) and a screw speed of 60 RPM. Mechanical Properties determinations
- a standard flexural bar 5" x 1 A” x 1 A” was used for ASTM D648 HDT determinations and for ASTM D256 Notched Izod measurements (test method A).
- a type I ASTM tensile bar, 4.5" in gage length x 7 2 " wide x 1 A " thick was used for ASTM D638 Tensile properties determinations. Examples 1 to 3
- HDT Temperature
- ⁇ Tensile properties measured according to ASTM D 638.
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Abstract
The invention relates to a sulfone polymer composition comprising : at least one high glass transition temperature sulfone polymer (A); at least one miscible polymer (B); and at least one immiscible polymer (C). The invention also relates to a process for manufacturing the sulfone polymer composition and to the articles thereof. The sulfone polymer composition of the invention possesses notably thermal performances and processability advantages in addition to minor cost with respect to high glass transition temperature sulfone polymers taken done.
Description
Sulfone polymer composition
The invention relates to a sulfone polymer composition having a good balance between high temperature performances, melt processability and economic aspects.
REFERENCE TO RELATED APPLICATIONS This application claims priority to U.S. provisional application 60/614,973, filed October 4, 2004, to EP application 04106875.0, filed on December 22, 2004, to U.S. provisional application 60/615,023, filed October 4, 2004, to U.S. provisional application 60/619,695, filed October 19, 2004, to U.S. provisional application 60/619,694, filed October 19, 2004, whose disclosures are incorporated herein by reference.
High glass transition temperature sulfone polymers are attractive because of their outstanding heat resistance, dimensional stability, good chemical resistance and mechanical integrity up to operating temperature of about 250°C.
Nevertheless, these high glass transition temperature sulfone polymer present several drawbacks, in particular a poor melt processability (due to the extremely high glass transition temperature), and a high cost, due to the expensive monomers required for their synthesis.
These drawbacks and others are remarkably overcome by a sulfone polymer composition comprising : - at least one high glass transition temperature sulfone polymer (A)
- at least one miscible polymer (B); and
- at least one immiscible polymer (C).
The sulfone polymer composition of the invention possesses advantageously thermal performances and processability advantages in addition to minor cost with respect to high glass transition temperature sulfone polymers. For the purpose of the invention, the term "polymer" is intended to denote any material consisting essentially of recurring units, and having a molecular weight above 2000.
For the purpose of the invention, the term "high glass transition temperature sulfone polymer" (A) is intended to denote any polymer, at least 50 % wt of the recurring units thereof being recurring units (Rl) :
(Rl) wherein :
- Q is a group chosen among the following structures
L H, Jn c with n = integer from 1 to 6, or an aliphatic divalent group, linear or branched, of up to 6 carbon atoms; and mixtures thereof; and
- Ar is a group chosen among the following structures
J J J J VY lUl n = integer from 1 to 6, or an aliphatic divalent group, linear or branched, of up to 6 carbon atoms; and mixtures thereof.
(0
(ϋ)
More preferably, recurring units (Rl) are recurring units (ii). Polymer (A) may notably be a homopolymer or a copolymer. Should polymer (A) be a copolymer, it may notably be a random, alternating or block copolymer. Although polymer (A) may be a block copolymer in certain particular embodiments of the invention, polymer (A) is generally not a block copolymer.
The high glass temperature sulfone polymer (A) comprises preferably 70 % wt, more preferably 75 % wt of recurring units (Rl); still more preferably, it contains no recurring unit other than recurring units (Rl). Excellent results were obtained with high glass transition temperature sulfone polymer (A) consisting of recurring units (ii) (polybiphenyldisulfone, hereinafter).
The term "at least one high transition temperature solfone polymer (A)" means that the polymer composition can comprise one or more than one polymer (A). Should the composition comprise several polymers (A), said polymers (A) are usually miscible, that implies that they display only one glass transition temperature.
The high glass transition temperature sulfone polymer (A) has a glass transition temperature advantageously of at least 230°C, preferably of at least 240°C, more preferably of at least 250°C.
The sulfone polymer composition advantageously comprises at least 20 % wt, preferably at least 40 % wt, more preferably at least 50 % wt of high glass transition temperature sulfone polymer (A), with respect to the total weight Of (A)5 (B) and (C).
The sulfone polymer composition advantageously comprises at most 90 % wt, preferably at most 80 % wt, more preferably at most 75 % wt of high glass transition temperature sulfone polymer (A), with respect to the total weight Of (A)5 (B) and (C).
For the purpose of the invention, the term "miscible polymer" (B) is intended to denote any polymer miscible with the high glass temperature sulfone polymer (A) in the composition according to the invention, i.e. a polymer yielding a single homogeneous phase when mixed with said high glass temperature sulfone polymer (A), showing only one glass transition temperature.
Preferably, the miscible polymer (B) is a miscible sulfone polymer.
For the purpose of the invention, the term "miscible sulfone polymer" is intended to denote any polymer, at least 50 % wt of the recurring units thereof being recurring units
(R2) wherein Ar' is a group chosen among the following structures
Recurring units (R2) are preferably chosen from :
Ov) and mixtures therefrom.
More preferably, recurring units (R2) are recurring units (j).
The miscible sulfone polymer comprises generally more than 50 % wt, preferably 70 % wt, more preferably 75 % wt of recurring units (R2). Still more preferably, it contains no recurring unit other than recurring units (R2).
Good results were obtained with miscible sulfone polymer, the recurring units thereof are recurring units (j) (polyphenylsulfone, hereinafter).
Polyphenylsulfone is available as RADEL® R PPSF from Solvay Advanced Polymers, L.L.C..
The sulfone polymer composition advantageously comprises at least 5 % wt, preferably at least 7.5 % wt, more preferably at least 10 % wt of miscible polymer (B), with respect to the total weight of (A), (B) and (C).
The sulfone polymer composition advantageously comprises at most 60 % wt, preferably at most 50 % wt, more preferably at least 40 % wt of miscible polymer (B), with respect to the total weight of (A), (B) and (C).
For the purpose of the invention, the term "immiscible polymer" is intended to denote any polymer immiscible with the high glass transition temperature sulfone polymer (A) in the composition according to the invention, i.e. a polymer yielding a phase-separated mixture when mixed with said high glass transition temperature sulfone polymer (A) or with the mixture of (A) and (B), showing two distinct glass transition temperatures.
One typical feature obtained by adding said immiscible polymer (C) to components (A) and (B) is thus that, since the high glass transition temperature sulfone polymer (A) [and the mixture of (A) and (B)] and the immiscible polymer are phase separated, they retain their separate glass transition temperatures.
The immiscible polymer (C) has a glass transition temperature of advantageously at least 150°C, preferably at least 160°C, more preferably at least 175°C.
The immiscible polymer (C) has a glass transition temperature of advantageously at most 240°C, preferably at most 235°C, more preferably at most 230°C.
Advantageously, the immiscible polymer (C) is selected from the group consisting of immiscible sulfone polymers, polyetherimide polymers, polyetheretherketone polymers (PEEK, herein after), and mixtures thereof.
For the purpose of this invention, the term "immiscible sulfone polymer" is intended to denote any polymer, at least 50 % wt of the recurring units thereof being recurring units (R3), chosen from :
Gv) and mixtures therefrom.
Good results were obtained with immiscible sulfone polymer (C) the recurring units of which are recurring units Qj) (polyetherethersulfone, hereinafter), with immiscible sulfone polymer (C) the recurring units of which are recurring units Qjj) and, optionally in addition, recurring units Qj) (polyethersulfone, hereinafter) and with immiscible sulfone polymers (C) the recurring units of which are recurring units Qv) (polysulfone, hereinafter).
Polysulfone is available as UDEL® PSF from Solvay Advanced Polymers, L.L.C.. Polyethersulfone is available as RADEL® A PES from Solvay Advanced Polymers, L.L.C..
The immiscible sulfone polymer comprises preferably 70 % wt, more preferably 75 % wt of recurring units (R3). Still more preferably, it contains no recurring unit other than recurring units (R3).
For the purpose of the invention, the term "polyetherimide polymer" is intended to denote any polymer, at least 50 % wt of the recurring units thereof being recurring units (R4), comprising two imide groups as such (R4-A) and/or in their corresponding amic acid forms [(R4-B) and (R4-C)] :
(R4-C) wherein :
- the — > denotes isomerism so that in any recurring unit the groups to which the arrows point may exist as shown or in an interchanged position;
- E is typically :
with the linking groups being in ortho, meta or para position and R' being a hydrogen atom or an alkyl radical comprising from 1 to 6 carbon
L H, J n atoms ; z with n = integer from 1 to 6 ;
- Ar" is typically :
Recurring units (R4) are preferably recurring units (k), in imide (k-A) and/or in amic acid form [(k-B) and (k-C)] :
(k-C) wherein in formulae (k-B) and (k-C) the — > denotes isomerism so that in any recurring unit the groups to which the arrows point may exist as shown or in an interchanged position.
The polyetherimide polymer comprises advantageously at least 50 % wt, preferably 70 % wt, more preferably 75 % wt of recurring units (R4), still more preferably, it contains no recurring unit other than recurring units (R4).
Good results have been obtained with polyetherimide polymer consisting of recurring units (k). Polymers available as ULTEM® PEI from GE Plastics comply with this criterion.
For the purpose of this invention, the term "polyetherether ketone polymer" is intended to denote any polymer, at least 50 % wt of the recurring units thereof being recurring units (R5) :
(R5)
The polyetheretherketone polymer comprises advantageously at least 50 % wt, preferably 70 % wt, more preferably 75 % wt of recurring units (R5), still more preferably, it contains no recurring unit other than recurring units (R5).
Polymers commercially available as VICTREX® PEEK comply with this criterion.
The sulfone polymer composition advantageously comprises at least 5 % wt, preferably at least 7.5 % wt, more preferably at least 10 % wt of immiscible polymer (C), with respect to the total weight of (A), (B) and (C).
The sulfone polymer composition advantageously comprises at most 60 % wt, preferably at most 50 % wt, more preferably at least 40 % wt of immiscible polymer (C), with respect to the total weight of (A), (B) and (C).
In a first preferred embodiment of the invention, the immiscible polymer (C) is an immiscible sulfone polymer selected from the group consisting of poly sulfone, polyethersulfone, polyetherethersulfone and mixtures thereof. More preferably, the component (C) of the first embodiment of the invention is chosen among the group consisting of polyethersulfone, polysulfone and mixtures thereof.
In a second preferred embodiment of the invention, the immiscible polymer (C) is a polyetherimide polymer. More preferably, the component (C) of the first embodiment of the invention is a polyetherimide polymer consisting of recurring units (k).
Optionally, the sulfone polymer composition can further comprise lubricating agents, heat stabilizer, anti-static agents, extenders, reinforcing agents, organic and/or inorganic pigments like TiO2, carbon black, acid scavengers, such as MgO, stabilizers, i.e., metal oxides such as zinc oxide, antioxidants, flame retardants, smoke-suppressing agents.
The sulfone polymer composition optionally comprises at least one filler chosen from reinforcing fillers, structural fibers and mixtures thereof. Structural fibers may include glass fiber, carbon or graphite fibers, and fibers formed of
silicon carbide, alumina, titania, boron and the like, and may include mixtures comprising two or more such fibers. Reinforcing fillers which can also be used in sulfone polymer composition include notably pigments, flake, spherical and fibrous particulate filler reinforcements and nucleating agents such as talc, mica, titanium dioxide, potassium titanate, silica, kaolin, chalk, alumina, mineral fillers, and the like. The reinforcing fillers and structural fibers can be used alone or in any combination.
Another aspect of the present invention concerns a process for manufacturing the sulfone polymer composition as above described, which comprises mixing the at least one high glass transition temperature sulfone polymer (A), the at least one miscible polymer (B), and the at least one immiscible polymer (C).
Advantageously, the process comprises mixing by dry blending and/or melt compounding the high glass transition temperature sulfone polymer (A), the miscible polymer (B), and the immiscible polymer (C).
Preferably, the high glass transition temperature sulfone polymer (A), the miscible polymer (B), and the immiscible polymer (C) are mixed by melt compounding.
Advantageously, the high glass transition temperature sulfone polymer (A), the miscible polymer (B), and the immiscible polymer (C) are melt compounded in continuous or batch devices. Such devices are well-known to those skilled in the art.
Examples of suitable continuous devices to melt compound the sulfone polymer composition of the invention are notably screw extruders. Thus, the high glass transition temperature sulfone polymer (A), the miscible polymer (B), and the immiscible polymer (C) and optionally, other ingredients, are advantageously fed in powder or granular form in an extruder and the sulfone polymer composition is advantageously extruded into strands and the strands are advantageously chopped into pellets. Optionally, fillers, lubricating agents, heat stabilizer, anti-static agents, extenders, reinforcing agents, organic and/or inorganic pigments like TiO2, carbon black, acid scavengers, such as MgO, flame-retardants, smoke- suppressing agents may be added to the composition during the compounding step.
Preferably, the high glass transition temperature sulfone polymer (A), the miscible polymer (B), and the immiscible polymer (C) are melt compounded in a twin-screw extruder.
The sulfone polymer composition can be processed following standard methods for injection molding, extrusion, thermoforming, machining, and blow molding. Solution-based processing for coatings and membranes is also possible. Finished articles comprising the sulfone polymer composition can undergo standard post-iabrication operations such as ultrasonic welding, adhesive bonding, and laser marking as well as heat staking, threading, and machining.
Still an object of the invention is an article comprising the sulfone polymer composition as above described.
Advantageously the article is an injection molded article, an extrusion molded article, a shaped article, a coated article or a casted article. Non- limitative examples of articles are shaped article, electronic components (such as printed circuit boards, electrical plug- in connectors, bobbins for relays and solenoids), pipes, fittings, housings, films, membranes, coatings.
The articles according to the invention can be fabricated by processing the sulfone polymer composition as above described following standard methods.
The present invention is described in greater detail below by referring to the Examples; however, the present invention is not limited to these examples. Raw materials :
The polybiphenyldisulfone obtained from the polycondensation of 4,4'-bis-(4-chlorophenyl sulfonyl)biphenyl and 4,4'-dihydroxydiphenyl, has been used. The table 1 here below summarizes main properties of two materials used in preparing the compositions :
Table 1 - Properties of the polybiphenyldisulfone polymers
(f ) Melt flow index measured according to ASTM D 1238, at a temperature of 4000C, under a load of 5 kg.
(π) Tensile properties measured according to ASTM D 638.
(X) Notched Izod has been measured at 250C according to ASTM D256 (test method A). (§) Test parts were annealed at 25O0C for 1 hour prior to HDT testing. Heat Deflection
Temperature (HDT) has been measured according to ASTM D648. (*) Izod break type : Complete.
RADEL® R-5800 NT polyphenylsulfone commercially available from Solvay Advanced Polymers, L.L.C., a sulfone polymer obtained from the poly condensation of a 4,4'-dihalodiphenylsulfone and 4,4'-dihydroxydiphenyl, has been used. Table 2 here below summarizes main properties of the material used in preparing the compositions : Table 2 - Properties of the polyphenylsulfone
(f) Melt flow index measured according to ASTM D 1238, at a temperature of 4000C, under a load of 5 kg. (π) Tensile properties measured according to ASTM D 638.
(X) Notched Izod has been measured at 250C according to ASTM D256 (test method A).
(§) Test parts were annealed at 2000C for 1 hour prior to HDT testing. Heat Deflection
Temperature (HDT) has been measured according to ASTM D648. (f) Izod break type : Partial
RADEL® A-301 NT polyethersulfone commercially available from Solvay Advanced Polymers, L.L.C., a polyethersulfone polymer obtained from the
poly condensation of a 4,4'-dihalodiphenylsulfone and
4,4'-dihydroxydiphenylsulfone, UDEL® P- 1700 NT polysulfone, a polysulfone obtained from the poly condensation of a 4,4'-dihalodiphenylsulfone and Bisphenol-A commercially available from Solvay Advanced Polymers, L.L.C., and ULTEM® 1000 polyetherimide commercially available from GE Plastics have been used. Table 3 here below summarizes main properties of the materials used in preparing the compositions : Table 3 - Properties of the immiscible polymers
(f) Melt flow index measured according to ASTM D 1238, at a temperature of 4000C, under a load of 5 kg.
(X) Notched Izod has been measured at 250C according to ASTM D256 (test method A). (§) Test parts were annealed at 2000C for 1 hour prior to HDT testing. Heat Deflection
Temperature (HDT) has been measured according to ASTM D648. (π) Tensile properties measured according to ASTM D 638. Compounding procedure :
The compositions were melt compounded using a 25 mm diameter twin screw double vented Berstorff extruder having an L/D ratio of 33/1 according to the conditions profile shown in Table 4. The first vent port was open to the atmosphere; the second was connected to a vacuum pump. The extruder was fitted with a double strand die. The polymer extrudate was pelletized after passing through a water trough for cooling. All blends were extruded and pelletized without incident at the throughput rates indicated in Table 4.
Table 4 - Compounding conditions
Injection molding procedure
Following compounding, the resin pellets from the various resins and compositions were dried for about 16 hrs in a 149°C (300 F) desiccated hot air oven with a due point of -37.2°C (-35 F). Parts were then injection molded into 1/8" thick ASTM tensile and flexural test specimens using a Wasp Mini-Jector benchtop injection molding machine equipped with a 3/4" general purpose screw and a 20 L/D. Injection molding machine temperature settings were 395°C, 400°C and 405 °C for the rear, front and nozzle sections respectively. An injection pressure of 1100 psi was used along with a mold temperature of 85°C (185 F) and a screw speed of 60 RPM. Mechanical Properties determinations
A standard flexural bar 5" x 1A" x 1A" was used for ASTM D648 HDT determinations and for ASTM D256 Notched Izod measurements (test method A). A type I ASTM tensile bar, 4.5" in gage length x 72" wide x 1A " thick was used for ASTM D638 Tensile properties determinations. Examples 1 to 3
Ternary blends of a high glass transition temperature sulfone polymer, a miscible sulfone polymer and an immiscible polymer were prepared by melt compounding as specified here above. Details of composition and characterization of the blends are summarized in Table 5 here below.
Table 5 - Composition and characterization of ternary blends
(f) Melt flow index measured according to ASTM D 1238, at a temperature of 4000C, under a load of 5 kg.
(X) Notched Izod has been measured at 250C according to ASTM D256 (test method A). (§) Test parts were annealed at 23O0C for 1 hour prior to HDT testing. Heat Deflection
Temperature (HDT) has been measured according to ASTM D648. (π) Tensile properties measured according to ASTM D 638.
Claims
C L A I M S
1 - Sulfone polymer composition comprising :
- at least one high glass transition temperature sulfone polymer (A);
- at least one miscible polymer (B); and
- at least one immiscible polymer (C).
where at least 50 % wt of the recurring units of polymer (A) are recurring units (Rl) :
(Rl) wherein :
- Q is a group chosen among the following structures :
n
2 with n = integer from 1 to 6, or an aliphatic divalent group, linear or branched, of up to 6 carbon atoms;
and mixtures thereof; and
- Ar is a group chosen among the following structures
and mixtures thereof.
2 - Composition according to Claim 1, characterized in that recurring units (Rl) are recurring units (ii) :
(ϋ)
3 - Composition according to Claim 1 or 2, characterized in that polymer (A) contains no recurring unit other than recurring units (Rl).
4 - Composition according to anyone of the preceding Claims, characterized in that polymer (B) is a miscible sulfone polymer, at least 50 % wt of the recurring units thereof being recurring units (R2) :
(R2)
wherein Ar' is a group chosen among the following structures :
5 - Composition according to Claim 4, characterized in that at least 50 % wt of the recurring units of the polymer (B) are recurring units (j) :
U)
6 - Composition according to anyone of preceding Claims, characterized in that the immiscible polymer (C) is selected from the group consisting of immiscible sulfone polymers, polyetherimide polymers, polyetheretherketone polymers, and mixtures thereof.
7 - Composition according to Claim 6, characterized in that the immiscible polymer (C) is an immiscible sulfone polymer selected from the group consisting of poly sulfone, polyethersulfone, polyetherethersulfone and mixtures thereof.
8 - Composition according to Claim 6, characterized in that the immiscible polymer (C) is a polyetherimide polymer.
9 - Composition according to Claim 6 or 8, characterized in that the immiscible polymer (C) is a polyetherimide polymer, at least 50 % wt of the
recurring units thereof being recurring unit (k), in imide (k-A) and/or amic acid form [(k-B) and (k-C)] :
(k-C) wherein in formulae (k-B) and (k-C) the — > denotes isomerism so that in any recurring unit the groups to which the arrows point may exist as shown or in an interchanged position.
10 - Process for manufacturing the sulfone polymer composition according to anyone of Claims 1 to 9, which comprises mixing the at least one high glass transition temperature sulfone polymer (A), the at least one miscible polymer (B), and the at least one immiscible polymer (C).
11 - Article comprising the sulfone polymer composition according to anyone of Claims 1 to 9.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2007535143A JP2008516028A (en) | 2004-10-04 | 2005-09-30 | Sulfone polymer composition |
| EP05792122.3A EP1799769B1 (en) | 2004-10-04 | 2005-09-30 | Sulfone polymer composition |
| US11/576,556 US20090124767A1 (en) | 2004-10-04 | 2005-09-30 | Sulfone Polymer Composition |
Applications Claiming Priority (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US61502304P | 2004-10-04 | 2004-10-04 | |
| US61497304P | 2004-10-04 | 2004-10-04 | |
| US60/615,023 | 2004-10-04 | ||
| US60/614,973 | 2004-10-04 | ||
| US61969404P | 2004-10-19 | 2004-10-19 | |
| US61969504P | 2004-10-19 | 2004-10-19 | |
| US60/619,695 | 2004-10-19 | ||
| US60/619,694 | 2004-10-19 | ||
| EP04106875A EP1524297A1 (en) | 2004-12-22 | 2004-12-22 | Sulfone polymer composition |
| EP04106875.0 | 2004-12-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2006037753A1 true WO2006037753A1 (en) | 2006-04-13 |
Family
ID=34354662
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2005/054934 WO2006037753A1 (en) | 2004-10-04 | 2005-09-30 | Sulfone polymer composition |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20090124767A1 (en) |
| EP (2) | EP1524297A1 (en) |
| JP (1) | JP2008516028A (en) |
| IN (1) | IN2007CH01386A (en) |
| TW (2) | TW200628300A (en) |
| WO (1) | WO2006037753A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010530914A (en) * | 2007-06-22 | 2010-09-16 | ビーエーエスエフ ソシエタス・ヨーロピア | Molding materials containing polyaryl ethers with improved surface quality |
| US11225574B2 (en) | 2015-12-01 | 2022-01-18 | Solvay Specialty Polymers Usa, Llc | Polymer compositions including a poly(ether sulfone) blend and articles made therefrom |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070066741A1 (en) * | 2005-09-16 | 2007-03-22 | Donovan Michael S | High glass transition temperature thermoplastic articles |
| US8034857B2 (en) | 2007-07-12 | 2011-10-11 | Sabic Innovative Plastics Ip B.V. | Polyetherimide/polyphenylene ether sulfone blends |
| KR101912484B1 (en) * | 2011-05-25 | 2018-10-26 | 솔베이 스페셜티 폴리머즈 유에스에이, 엘엘씨 | Polymers with reduced estrogenic activity |
| EP2738219A1 (en) | 2012-11-28 | 2014-06-04 | Solvay Specialty Polymers USA, LLC. | PAEK/PAES compositions |
| JP2016516884A (en) | 2013-05-08 | 2016-06-09 | ソルベイ スペシャルティ ポリマーズ ユーエスエー， エルエルシー | Polyarylene ether sulfone (PAES) polymer |
| JP2016516885A (en) | 2013-05-08 | 2016-06-09 | ソルベイ スペシャルティ ポリマーズ ユーエスエー， エルエルシー | Polyarylene ether sulfone (PAES) composition |
| WO2015011004A2 (en) * | 2013-07-22 | 2015-01-29 | Solvay Specialty Polymers Usa, Llc | Chemical processing articles |
| ES2909439T3 (en) | 2013-10-15 | 2022-05-06 | Basf Se | Improved chemical stability of filtration membranes |
| EP3950808A4 (en) | 2019-03-27 | 2022-12-28 | Sekisui Chemical Co., Ltd. | Resin composition and molded object |
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| EP0297363A3 (en) * | 1987-06-27 | 1989-09-13 | BASF Aktiengesellschaft | High temperature resistant thermoplastic moulding masses with improved melt stability |
| US5189115A (en) * | 1989-02-21 | 1993-02-23 | Amoco Corporation | Polyetherimide copolymers |
| US6075100A (en) * | 1999-07-28 | 2000-06-13 | Bp Amoco Corporation | Ternary poly(biphenyl ether sulfone) resin blends having improved environmental stress cracking resistance |
| EP1695994B1 (en) * | 2005-02-24 | 2009-05-06 | Solvay Advanced Polymers, L.L.C. | Aromatic high glass temperature sulfone polymer composition |
| EP1526158A1 (en) * | 2004-12-22 | 2005-04-27 | Solvay Advanced Polymers, L.L.C. | Electronic components |
| US20080058480A1 (en) * | 2004-10-04 | 2008-03-06 | Solvay Advanced Polymers | Sulfone Polymer Composition |
| EP1802704B1 (en) * | 2004-10-04 | 2014-11-12 | Solvay Specialty Polymers USA, LLC. | High performance membranes, methods of making, and uses thereof |
-
2004
- 2004-12-22 EP EP04106875A patent/EP1524297A1/en not_active Withdrawn
-
2005
- 2005-09-30 JP JP2007535143A patent/JP2008516028A/en active Pending
- 2005-09-30 EP EP05792122.3A patent/EP1799769B1/en not_active Not-in-force
- 2005-09-30 WO PCT/EP2005/054934 patent/WO2006037753A1/en active Application Filing
- 2005-09-30 US US11/576,556 patent/US20090124767A1/en not_active Abandoned
- 2005-10-03 TW TW94134513A patent/TW200628300A/en unknown
- 2005-10-03 TW TW94134508A patent/TW200624483A/en unknown
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2007
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| EP0176989A1 (en) * | 1984-09-28 | 1986-04-09 | Amoco Corporation | Molded articles manufactured from blends of a biphenyl containing poly(aryl ether sulfone) and a poly(aryl ether ketone) |
| EP0215580A2 (en) * | 1985-08-19 | 1987-03-25 | Union Carbide Corporation | Miscible blends of poly(aryl ether sulfones) |
| EP0332012A1 (en) * | 1988-03-05 | 1989-09-13 | BASF Aktiengesellschaft | High temperature resistant polyarylethersulfone-/polyaryleneetherketone moulding compounds with improved phase cohesion |
| EP0376349A2 (en) * | 1988-12-30 | 1990-07-04 | Amoco Corporation | Miscible blends of imide containing polymers with poly(aryl sulfones) |
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| JP2010530914A (en) * | 2007-06-22 | 2010-09-16 | ビーエーエスエフ ソシエタス・ヨーロピア | Molding materials containing polyaryl ethers with improved surface quality |
| US11225574B2 (en) | 2015-12-01 | 2022-01-18 | Solvay Specialty Polymers Usa, Llc | Polymer compositions including a poly(ether sulfone) blend and articles made therefrom |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1524297A1 (en) | 2005-04-20 |
| JP2008516028A (en) | 2008-05-15 |
| US20090124767A1 (en) | 2009-05-14 |
| EP1799769A1 (en) | 2007-06-27 |
| TW200624483A (en) | 2006-07-16 |
| EP1799769B1 (en) | 2014-04-16 |
| IN2007CH01386A (en) | 2007-08-31 |
| TW200628300A (en) | 2006-08-16 |
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