JP4990148B2 - Aromatic high glass transition temperature sulfone polymer composition - Google Patents
Aromatic high glass transition temperature sulfone polymer composition Download PDFInfo
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- JP4990148B2 JP4990148B2 JP2007535151A JP2007535151A JP4990148B2 JP 4990148 B2 JP4990148 B2 JP 4990148B2 JP 2007535151 A JP2007535151 A JP 2007535151A JP 2007535151 A JP2007535151 A JP 2007535151A JP 4990148 B2 JP4990148 B2 JP 4990148B2
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- 239000000203 mixture Substances 0.000 title claims description 74
- 229920000642 polymer Polymers 0.000 title claims description 67
- 125000003118 aryl group Chemical group 0.000 title claims description 30
- 230000009477 glass transition Effects 0.000 title claims description 21
- 150000003457 sulfones Chemical class 0.000 title claims description 18
- -1 aromatic sulfone Chemical class 0.000 claims description 31
- 150000007942 carboxylates Chemical class 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 229920000515 polycarbonate Polymers 0.000 claims description 10
- 239000004417 polycarbonate Substances 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 229910044991 metal oxide Inorganic materials 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 6
- 150000004706 metal oxides Chemical class 0.000 claims description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 4
- 229910052723 transition metal Inorganic materials 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000003624 transition metals Chemical class 0.000 claims description 2
- 239000011521 glass Substances 0.000 claims 2
- 230000007704 transition Effects 0.000 claims 2
- 229920002492 poly(sulfone) Polymers 0.000 description 9
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 8
- HNSDLXPSAYFUHK-UHFFFAOYSA-N 1,4-bis(2-ethylhexyl) sulfosuccinate Chemical compound CCCCC(CC)COC(=O)CC(S(O)(=O)=O)C(=O)OCC(CC)CCCC HNSDLXPSAYFUHK-UHFFFAOYSA-N 0.000 description 7
- 229920000491 Polyphenylsulfone Polymers 0.000 description 7
- 239000000835 fiber Substances 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000004695 Polyether sulfone Substances 0.000 description 5
- 229920003295 Radel® Polymers 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 229920006393 polyether sulfone Polymers 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000008188 pellet Substances 0.000 description 4
- 239000011787 zinc oxide Substances 0.000 description 4
- 229920003286 Udel® P-3703 Polymers 0.000 description 3
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- 239000012744 reinforcing agent Substances 0.000 description 3
- 239000012763 reinforcing filler Substances 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 0 Cc(cc1)ccc1S(*S(c(cc1)ccc1O[Al]OC)(=O)=O)(=O)=O Chemical compound Cc(cc1)ccc1S(*S(c(cc1)ccc1O[Al]OC)(=O)=O)(=O)=O 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229910010413 TiO 2 Inorganic materials 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
- 238000004458 analytical method Methods 0.000 description 2
- 239000002216 antistatic agent Substances 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
- 239000006229 carbon black Substances 0.000 description 2
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- 239000003480 eluent Substances 0.000 description 2
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- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 239000012860 organic pigment Substances 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-M 9-cis,12-cis-Octadecadienoate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC([O-])=O OYHQOLUKZRVURQ-HZJYTTRNSA-M 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 108010002493 Arachin Proteins 0.000 description 1
- 102100022005 B-lymphocyte antigen CD20 Human genes 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
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- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 238000003436 Schotten-Baumann reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical class CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229940116224 behenate Drugs 0.000 description 1
- UKMSUNONTOPOIO-UHFFFAOYSA-M behenate Chemical compound CCCCCCCCCCCCCCCCCCCCCC([O-])=O UKMSUNONTOPOIO-UHFFFAOYSA-M 0.000 description 1
- 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 1
- 238000000071 blow moulding Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 108010059485 brain synaptic membrane glycoprotein gp 50 Proteins 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- WNPXRNJEBMRJGV-UHFFFAOYSA-N chembl1399590 Chemical compound COC1=CC=CC(C=2N=C3C=CC=CC3=C(N3C(CCCC3)C)N=2)=C1O WNPXRNJEBMRJGV-UHFFFAOYSA-N 0.000 description 1
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- 229920001577 copolymer Polymers 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-M decanoate Chemical compound CCCCCCCCCC([O-])=O GHVNFZFCNZKVNT-UHFFFAOYSA-M 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 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
- 238000009826 distribution Methods 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000003949 imides Chemical group 0.000 description 1
- 238000001746 injection moulding Methods 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
- 229940070765 laurate Drugs 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 229940049918 linoleate Drugs 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 150000002739 metals 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
- 229940105132 myristate Drugs 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920013655 poly(bisphenol-A sulfone) Polymers 0.000 description 1
- 229920005649 polyetherethersulfone Polymers 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229910052705 radium Inorganic materials 0.000 description 1
- WBHHMMIMDMUBKC-QJWNTBNXSA-M ricinoleate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O WBHHMMIMDMUBKC-QJWNTBNXSA-M 0.000 description 1
- 229940066675 ricinoleate Drugs 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
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- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
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- Compositions Of Macromolecular Compounds (AREA)
Description
〔参照する関連出願〕
本出願は、2004年10月4日に提出された米国仮出願第60/615,025号明細書及び2005年2月24日に提出された欧州特許出願第05101408.2号明細書に対する優先権を主張し、それらの開示を参照としてここに組み込む。
[Related applications to be referenced]
This application claims priority to US Provisional Application No. 60 / 615,025 filed on October 4, 2004 and European Patent Application No. 05101408.2 filed on February 24, 2005; The disclosures of which are incorporated herein by reference.
一方で、スルホンポリマーの性質は、一定量の抽出可能硫酸塩がポリマーのほかに多く存在することである。他方で、半導体産業などの敏感な電子工学用途のような、抽出可能イオンを最小化する必要のある用途に用いるのに好適な芳香族高ガラス転移温度ポリマー、例えばポリスルホン、ポリエーテルスルホン、及びポリフェニルスルホンが必要とされる。すでに、抽出される硫酸塩の濃度を低下させるための添加剤パッケージを開発することが試されている。
残念ながら、抽出可能硫酸塩の濃度を減少させるこれらの添加剤も抽出される。結果として、これらの添加剤はさらなる抽出可能な問題を導く。これらの欠点又は他の欠点は、本発明の芳香族高ガラス転移温度ポリマー組成物によって顕著に克服される。
On the other hand, the property of the sulfone polymer is that a certain amount of extractable sulfate is present in addition to the polymer. On the other hand, aromatic high glass transition temperature polymers suitable for use in applications where the extractable ions need to be minimized, such as sensitive electronics applications such as the semiconductor industry, such as polysulfone, polyethersulfone, and polysulfone. Phenylsulfone is required. Already, an attempt has been made to develop an additive package for reducing the concentration of sulfate extracted.
Unfortunately, these additives that reduce the concentration of extractable sulfate are also extracted. As a result, these additives lead to further extractable problems. These or other disadvantages are significantly overcome by the aromatic high glass transition temperature polymer compositions of the present invention.
従って、本発明の目的は、
-少なくとも1種の芳香族スルホンポリマー(P);
-少なくとも1種の金属酸化物;
-少なくとも10個の炭素原子を含む、少なくとも1種の金属カルボン酸塩:
を含む、芳香族高ガラス転移温度スルホンポリマー組成物である。
驚くべきことに、酸化物及びカルボン酸塩の組み合わせは、有利には硫酸イオンを封鎖する際に優れた効率を提供する。好ましくは、これらの添加剤がこの利点を提供し、さらにそれらが該芳香族スルホンポリマーの透明な外観を保持する。
Therefore, the object of the present invention is to
-At least one aromatic sulfone polymer (P);
-At least one metal oxide;
-At least one metal carboxylate containing at least 10 carbon atoms:
An aromatic high glass transition temperature sulfone polymer composition comprising:
Surprisingly, the combination of oxide and carboxylate advantageously provides excellent efficiency in sequestering sulfate ions. Preferably, these additives provide this advantage and further they retain the transparent appearance of the aromatic sulfone polymer.
本発明では、“ポリマー”という用語は、本質的に繰り返し単位からなり、且つ2000以上の分子量を有する任意の材料を意味することが意図される。
本発明では、“芳香族スルホンポリマー(P)”という用語は、その繰り返し単位の少なくとも5質量%が少なくとも1つの式1の基を含む任意のポリマーを意味することが意図される:
In the context of the present invention, the term “aromatic sulfone polymer (P)” is intended to mean any polymer in which at least 5% by weight of its repeat units contain at least one group of formula 1:
芳香族スルホンポリマー(P)は、有利には少なくとも150℃、好ましくは少なくとも160℃、さらに好ましくは少なくとも175℃のガラス転移温度を有する。
芳香族スルホンポリマー(P)は、少なくとも1つの上記式1の基を含む、少なくとも5質量%、好ましくは少なくとも20質量%、さらに好ましくは少なくとも30質量%、さらに好ましくは少なくとも50質量%、さらに好ましくは少なくとも75質量%の繰り返し単位を含む。最も好ましくは、芳香族スルホンポリマー(P)が、少なくとも1つの上記式1の基を含む繰り返し単位以外の繰り返し単位を含まない。
The aromatic sulfone polymer (P) advantageously has a glass transition temperature of at least 150 ° C., preferably at least 160 ° C., more preferably at least 175 ° C.
The aromatic sulfone polymer (P) comprises at least one group of formula 1 above, at least 5% by weight, preferably at least 20% by weight, more preferably at least 30% by weight, more preferably at least 50% by weight, more preferably Contains at least 75% by weight of repeating units. Most preferably, the aromatic sulfone polymer (P) does not contain repeating units other than the repeating unit comprising at least one group of formula 1 above.
本出願人は、該芳香族スルホンポリマー(P)における少なくとも1つの上記式1の基を含む繰り返し単位の少なくとも5質量%の割合は、本発明の組成物に対して、敏感な電子工学用途に求められる高温挙動を与えるのに十分であることを見出した。
本出願人は、本発明の範囲のこの制限によらず、芳香族ポリカーボネートポリマーの存在が、本発明の組成物の機械的特性及びイオン抽出特性に有害となり得ると考えている。
従って、本発明の組成物は、該組成物の全質量に基づき、有利には10質量%よりも少ない芳香族ポリカーボネート(PC)を含む。
Applicants have found that the proportion of at least 5% by weight of the repeating units comprising at least one group of formula 1 in the aromatic sulfone polymer (P) is sensitive to sensitive electronic applications relative to the composition of the present invention. It has been found that it is sufficient to give the required high temperature behavior.
Applicants believe that, despite this limitation of the scope of the invention, the presence of aromatic polycarbonate polymer can be detrimental to the mechanical and ion extraction properties of the compositions of the invention.
Thus, the composition according to the invention comprises preferably less than 10% by weight of aromatic polycarbonate (PC), based on the total weight of the composition.
本発明では、“芳香族ポリカーボネート(PC)”という用語は、その繰り返し単位の50質量%よりも多くが以下の式2に従う任意のポリマーを意味することが意図される:
芳香族ポリカーボネート(PC)の例は、以下の式3及び/又は4の繰り返し単位を含むポリマーである:
-各場合によって等しい又は異なるRa及びRbのぞれぞれは、独立に水素原子、ハロゲン又はC1-C6炭化水素基である;
-Eは、以下の構造の中から選択される二価の架橋性基である。
Each equal or different Ra and Rb is independently a hydrogen atom, a halogen or a C 1 -C 6 hydrocarbon group;
-E is a divalent crosslinkable group selected from the following structures.
芳香族ポリカーボネート(PC)は、特に商品名LEXAN(登録商標)(GEから)、MAKROLON(登録商標)(Bayerから)、CALIBER(登録商標)(Dowから)、PANLITE(登録商標)(帝人から)、及びIUPILON(登録商標)(三菱から)として市場で入手可能である。
芳香族ポリカーボネート(PC)は、商業的には2種の異なるプロセス:アミン-触媒界面縮合反応におけるホスゲン及び芳香族ジオールのSchotten-Baumann反応、又はビスフェノールと炭酸ジフェニルなどのモノマー炭酸塩との塩基-触媒エステル転移反応で調製され得る。
Aromatic polycarbonate (PC), especially under the trade names LEXAN (registered trademark) (from GE), MAKROLON (registered trademark) (from Bayer), CALIBER (registered trademark) (from Dow), PANLITE (registered trademark) (from Teijin) , And IUPILON (R) (from Mitsubishi).
Aromatic polycarbonate (PC) is commercially available in two different processes: the Schotten-Baumann reaction of phosgene and aromatic diols in amine-catalyzed interfacial condensation reactions, or the base of monomeric carbonates such as bisphenol and diphenyl carbonate. It can be prepared by catalytic transesterification.
本発明の組成物は、該組成物の全質量に基づき、好ましくは8質量%よりも少なく、さらに好ましくは7質量%よりも少なく、さらに好ましくは5質量%よりも少ない芳香族ポリカーボネート(PC)を含む。
本発明の好ましい実施態様では、本発明の組成物が芳香族ポリカーボネート(PC)を含まない。
本発明の組成物は、該組成物の全質量に基づき、有利には90質量%よりも多く、好ましくは92質量%よりも多く、さらに好ましくは95質量%よりも多く、さらに好ましくは97.5質量%よりも多くの芳香族スルホンポリマー(P)を含む。
該組成物は、該組成物の全質量に基づいて90質量%よりも多くの芳香族スルホンポリマー(P)を含むときに、敏感な電子工学用途、例えば半導体産業で評価される顕著な機械的特性及び耐熱性を有する。
The composition of the present invention, based on the total weight of the composition, is preferably less than 8% by weight, more preferably less than 7% by weight, more preferably less than 5% by weight aromatic polycarbonate (PC). including.
In a preferred embodiment of the present invention, the composition of the present invention does not contain an aromatic polycarbonate (PC).
The composition of the present invention is advantageously more than 90% by weight, preferably more than 92% by weight, more preferably more than 95% by weight, more preferably 97.5% by weight, based on the total weight of the composition. Contains more than% aromatic sulfone polymer (P).
When the composition contains more than 90% by weight of the aromatic sulfone polymer (P) based on the total weight of the composition, it is a significant mechanical component that is valued in sensitive electronics applications such as the semiconductor industry. Has properties and heat resistance.
本発明の第一の好ましい実施態様では、芳香族スルホンポリマー(P)の繰り返し単位の少なくとも5質量%が、イミド形態(R1-A)及び/又はアミド酸形態[(R1-B)及び(R1-C)]の繰り返し単位(R1)である。
-→は、全ての繰り返し単位において、矢印の指す基が示されているように存在し得るか、又は交換位置に存在し得る異性を意味する;
-Ar”は、以下の構造の中から選択される。
-→ means an isomerism that may be present in all repeating units as indicated by the group indicated by the arrow or may be in the exchange position;
“Ar” is selected from the following structures.
本発明の第一の好ましい実施態様の芳香族スルホンポリマー(P)は、少なくとも5質量%、好ましくは少なくとも20質量%、さらに好ましくは少なくとも30質量%、さらに好ましくは少なくとも50質量%、さらに好ましくは少なくとも75質量%の繰り返し単位(R1)を含む。最も好ましくは、繰り返し単位(R1)以外の繰り返し単位を含まない。 The aromatic sulfone polymer (P) of the first preferred embodiment of the present invention is at least 5% by weight, preferably at least 20% by weight, more preferably at least 30% by weight, more preferably at least 50% by weight, more preferably It contains at least 75% by weight of repeating units (R1). Most preferably, no repeating unit other than the repeating unit (R1) is contained.
本発明の第二の好ましい実施態様では、芳香族スルホンポリマー(P)の繰り返し単位の少なくとも5質量%が、繰り返し単位(R2)及び/又は繰り返し単位(R3)である:
-Qは以下の構造の中から選択される基である:
及びそれらの混合物;
-Arは以下の構造の中から選択される基である:
及びそれらの混合物;
-Ar'は以下の構造の中から選択される基である:
及びそれらの混合物。
In a second preferred embodiment of the present invention, at least 5% by mass of the repeating unit of the aromatic sulfone polymer (P) is the repeating unit (R2) and / or the repeating unit (R3):
-Q is a group selected from the following structures:
And mixtures thereof;
-Ar is a group selected from the following structures:
And mixtures thereof;
-Ar 'is a group selected from the following structures:
And mixtures thereof.
繰り返し単位(R2)は好ましくは以下から選択される:
繰り返し単位(R3)は好ましくは以下から選択される:
本発明の第二の好ましい実施態様の芳香族スルホンポリマー(P)は、少なくとも5質量%、好ましくは少なくとも20質量%、さらに好ましくは少なくとも30質量%、さらに好ましくは少なくとも50質量%、さらに好ましくは少なくとも75質量%の繰り返し単位(R2)及び/又は(R3)を含む。最も好ましくは、繰り返し単位(R2)及び/又は(R3)以外の繰り返し単位を含まない。 The aromatic sulfone polymer (P) of the second preferred embodiment of the present invention is at least 5 wt%, preferably at least 20 wt%, more preferably at least 30 wt%, more preferably at least 50 wt%, more preferably At least 75% by weight of repeating units (R2) and / or (R3) are included. Most preferably, no repeating unit other than the repeating units (R2) and / or (R3) is included.
良好な結果が、繰り返し単位が繰り返し単位(ii)(以下ではポリビフェニルジスルホン)である芳香族スルホンポリマー(P)、繰り返し単位が繰り返し単位(j)(以下ではポリフェニルスルホン)である芳香族スルホンポリマー(P)、繰り返し単位が繰り返し単位(jj)(以下ではポリエーテルエーテルスルホン)である芳香族スルホンポリマー(P)、繰り返し単位が繰り返し単位(jjj)及び任意にさらに繰り返し単位(jj)(以下ではポリエーテルスルホン)である芳香族スルホンポリマー(P)、及び繰り返し単位が繰り返し単位(jv)(以下ではポリスルホン)である芳香族スルホンポリマー(P)で得られた。 Good results are obtained when the aromatic sulfone polymer (P) is a repeating unit (ii) (hereinafter polybiphenyldisulfone) and the aromatic sulfone is a repeating unit (j) (hereinafter polyphenylsulfone). Polymer (P), aromatic sulfone polymer (P) in which the repeating unit is a repeating unit (jj) (hereinafter, polyetherethersulfone), the repeating unit is a repeating unit (jjj) and optionally further a repeating unit (jj) (hereinafter referred to as In the above, the aromatic sulfone polymer (P) which is a polyethersulfone and the aromatic sulfone polymer (P) whose repeating unit is a repeating unit (jv) (hereinafter referred to as polysulfone) were obtained.
ポリフェニルスルホンは、特にSolvay Advanced Polymers, L.L.C.からRADEL(登録商標)R PPSFとして入手可能である。ポリスルホンは、特にSolvay Advanced Polymers, L.L.C.からUDEL(登録商標)PSFとして入手可能である。ポリエーテルスルホンは、特にSolvay Advanced Polymers, L.L.C.からRADEL(登録商標)A PESとして入手可能である。
好ましくは、芳香族スルホンポリマー(P)が、ポリビフェニルジスルホン、ポリスルホン、ポリフェニルスルホン、ポリエーテルスルホン、コポリマー及びそれらの混合物からなる群の中から選択される。
Polyphenylsulfone is particularly available from Solvay Advanced Polymers, LLC as RADEL® R PPSF. Polysulfone is particularly available from Solvay Advanced Polymers, LLC as UDEL® PSF. Polyethersulfone is especially available as RADEL® A PES from Solvay Advanced Polymers, LLC.
Preferably, the aromatic sulfone polymer (P) is selected from the group consisting of polybiphenyldisulfone, polysulfone, polyphenylsulfone, polyethersulfone, copolymers and mixtures thereof.
好ましくは、金属酸化物が、アルカリ土類金属又は12族遷移金属の酸化物である。
本発明では、12族遷移金属として、Zn、Cd、Hg、Uubからなる金属の群を意味することを意図する。
さらに好ましくは、該酸化物が、CaO、MgO、ZnO及びそれらの混合物からなる群の中から選択される。さらに好ましくは、該酸化物がZnOである。
好ましくは、金属カルボン酸塩が、アルカリ土類金属又は12族遷移金属のカルボン酸塩である。
さらに好ましくは、該カルボン酸塩が、Ca、Mg、Zn及びそれらの混合物のカルボン酸塩からなる群の中から選択される。さらに好ましくは、該カルボン酸塩がカルボン酸亜鉛である。
好ましくは、該カルボン酸塩が、カプリン酸塩(C10)、ラウリン酸塩(C12)、ミリスチン酸塩(C14)、パルミチン酸塩(C16)、ステアリン酸塩(C18)、アラキン酸塩(C20)、ベヘン酸塩(C22)、パルミトレイン酸塩(C16)、オレイン酸塩(C18)、ガドレイン酸塩(C20)、リシノール酸塩(C18)、リノール酸塩(C18)、リノレン酸塩(C18)、及びそれらの混合物の中から選択される。さらに好ましくは、該カルボン酸塩がステアリン酸塩である。
優れた結果が、ステアリン酸亜鉛で得られた。
Preferably, the metal oxide is an alkaline earth metal or Group 12 transition metal oxide.
In the present invention, the group 12 transition metal is intended to mean a group of metals consisting of Zn, Cd, Hg, and Uub.
More preferably, the oxide is selected from the group consisting of CaO, MgO, ZnO and mixtures thereof. More preferably, the oxide is ZnO.
Preferably, the metal carboxylate is an alkaline earth metal or a Group 12 transition metal carboxylate.
More preferably, the carboxylate is selected from the group consisting of carboxylates of Ca, Mg, Zn and mixtures thereof. More preferably, the carboxylate is zinc carboxylate.
Preferably, the carboxylate is a caprate (C 10 ), a laurate (C 12 ), a myristate (C 14 ), a palmitate (C 16 ), a stearate (C 18 ), an arachin (C 20 ), behenate (C 22 ), palmitate (C 16 ), oleate (C 18 ), gadoleate (C 20 ), ricinoleate (C 18 ), linoleate (C 18 ), linolenic acid salt (C 18 ), and mixtures thereof. More preferably, the carboxylate is a stearate.
Excellent results were obtained with zinc stearate.
芳香族高ガラス転移温度ポリマー組成物は、該組成物の全質量に基づき、有利には少なくとも0.001質量%、好ましくは少なくとも0.005質量%、さらに好ましくは少なくとも0.01質量%の酸化物を含む。
芳香族高ガラス転移温度ポリマー組成物は、該組成物の全質量に基づき、有利には0.7質量%以下、好ましくは0.6質量%以下、さらに好ましくは0.5質量%以下、さらに好ましくは0.3質量%以下、最も好ましくは0.2質量%以下の酸化物を含む。
優れた結果が、該組成物が該組成物の全質量に基づいて0.02〜0.10質量%の酸化物を含んだときに得られた。
The aromatic high glass transition temperature polymer composition advantageously comprises at least 0.001% by weight, preferably at least 0.005% by weight, more preferably at least 0.01% by weight of oxide, based on the total weight of the composition.
The aromatic high glass transition temperature polymer composition is advantageously 0.7% by weight or less, preferably 0.6% by weight or less, more preferably 0.5% by weight or less, more preferably 0.3% by weight or less, based on the total weight of the composition. And most preferably 0.2% by mass or less of oxide.
Excellent results were obtained when the composition contained 0.02 to 0.10% oxide by weight based on the total weight of the composition.
芳香族高ガラス転移温度ポリマー組成物は、該組成物の全質量に基づき、有利には少なくとも0.005質量%、好ましくは少なくとも0.01質量%、さらに好ましくは少なくとも0.05質量%のカルボン酸塩を含む。
芳香族高ガラス転移温度ポリマー組成物は、該組成物の全質量に基づき、有利には1.00質量%以下、好ましくは0.75質量%以下、さらに好ましくは0.50質量%以下のカルボン酸塩を含む。
優れた結果が、該組成物が該組成物の全質量に基づいて0.05〜0.35質量%のカルボン酸塩を含んだときに得られた。
The aromatic high glass transition temperature polymer composition advantageously comprises at least 0.005% by weight, preferably at least 0.01% by weight, more preferably at least 0.05% by weight carboxylate, based on the total weight of the composition.
The aromatic high glass transition temperature polymer composition advantageously comprises 1.00% by weight or less, preferably 0.75% by weight or less, more preferably 0.50% by weight or less of the carboxylate salt based on the total weight of the composition.
Excellent results were obtained when the composition contained 0.05 to 0.35% by weight carboxylate based on the total weight of the composition.
本発明の組成物中の酸化物及びカルボン酸塩の質量比は、有利には1質量/質量以下、好ましくは0.75質量/質量以下、さらに好ましくは0.5質量/質量以下である。
本発明の組成物中の酸化物及びカルボン酸塩の質量比は、有利には少なくとも0.05質量/質量、好ましくは少なくとも0.075質量/質量、さらに好ましくは少なくとも0.10質量/質量である。
優れた結果が、0.1〜0.5質量/質量の酸化物及びカルボン酸塩の質量比で得られた。
The mass ratio of oxide and carboxylate in the composition of the present invention is advantageously 1 mass / mass or less, preferably 0.75 mass / mass or less, more preferably 0.5 mass / mass or less.
The mass ratio of oxide to carboxylate in the composition of the invention is advantageously at least 0.05 mass / mass, preferably at least 0.075 mass / mass, more preferably at least 0.10 mass / mass.
Excellent results were obtained with an oxide to carboxylate mass ratio of 0.1 to 0.5 mass / mass.
任意に、本発明の高ガラス転移温度スルホンポリマー組成物は、充填剤、潤滑剤、熱安定化剤、帯電防止剤、増量剤、強化剤、有機及び/又は無機顔料、例えばTiO2、カーボンブラック、抗酸化剤、難燃剤、防煙剤をさらに含むことができる。
本発明の組成物は、有利には強化用充填剤、構造用繊維及びそれらの混合物から選択される少なくとも1種の充填剤を含む。構造用繊維は、ガラス繊維、炭素又はグラファイト繊維、及び炭化ケイ素、アルミナ、チタニア、ホウ素などから形成される繊維を含んでもよく、及び2種以上の該繊維を含む混合物を含んでもよい。本発明の組成物にも用いることのできる強化用充填剤は、特に顔料、フレーク、球状及び繊維状粒子性充填強化剤及び核剤、例えばタルク、マイカ、二酸化チタン、チタン酸カリウム、シリカ、カオリン、チョーク、アルミナ、鉱物充填剤などを含む。強化用充填剤及び構造用繊維は、単独か又は任意に組み合わせて用いることができる。
Optionally, the high glass transition temperature sulfone polymer composition of the present invention comprises a filler, lubricant, heat stabilizer, antistatic agent, extender, reinforcing agent, organic and / or inorganic pigments such as TiO 2 , carbon black Further, an antioxidant, a flame retardant, and a smoke proofing agent can be further included.
The composition according to the invention advantageously comprises at least one filler selected from reinforcing fillers, structural fibers and mixtures thereof. Structural fibers may include glass fibers, carbon or graphite fibers, and fibers formed from silicon carbide, alumina, titania, boron, and the like, and may include a mixture including two or more such fibers. Reinforcing fillers that can also be used in the compositions of the present invention are in particular pigments, flakes, spherical and fibrous particulate filler reinforcing agents and nucleating agents such as talc, mica, titanium dioxide, potassium titanate, silica, kaolin. , Including chalk, alumina, mineral fillers. Reinforcing fillers and structural fibers can be used alone or in any combination.
本発明の別の特徴は、上記の高ガラス転移温度スルホンポリマー組成物を製造するための方法であって:
-芳香族スルホンポリマー(P);
-金属酸化物;
-金属カルボン酸塩、
を混合することを含む方法に関する。
Another feature of the present invention is a method for producing the above high glass transition temperature sulfone polymer composition comprising:
-Aromatic sulfone polymer (P);
-Metal oxides;
-Metal carboxylates,
A method comprising mixing.
有利には、本発明の方法が、ポリマー(P)、酸化物及びカルボン酸塩を乾式混合及び/又は融解配合することによって混合することを含む。
好ましくは、ポリマー(P)、酸化物及びカルボン酸塩が、融解配合によって混合される。
有利には、ポリマー(P)、酸化物及びカルボン酸塩が、連続式装置又はバッチ式装置で融解配合される。該装置は当業者によく知られている。
本発明のスルホンポリマー組成物を融解配合するのに好適な連続式装置の例は、特にスクリュー押出機である。従って、ポリマー(P)、酸化物及びカルボン酸塩及び任意の他の成分は、有利には粉末又は顆粒の形態で押出機に供給され、該組成物はストランドに押出され、及び該ストランドはペレットに刻まれる。
Advantageously, the method of the invention comprises mixing the polymer (P), oxide and carboxylate salt by dry blending and / or melt blending.
Preferably, polymer (P), oxide and carboxylate are mixed by melt blending.
Advantageously, the polymer (P), oxide and carboxylate are melt compounded in a continuous or batch apparatus. Such devices are well known to those skilled in the art.
An example of a continuous apparatus suitable for melt compounding the sulfone polymer composition of the present invention is in particular a screw extruder. Thus, the polymer (P), oxides and carboxylates and any other components are advantageously fed to the extruder in the form of powder or granules, the composition is extruded into strands, and the strands are pelleted Engraved on.
任意に、充填剤、潤滑剤、熱安定化剤、帯電防止剤、増量剤、強化剤、有機及び/又は無機顔料、例えばTiO2、カーボンブラック、難燃剤、防煙剤が、配合工程中に該組成物に加えられ得る。
好ましくは、ポリマー(P)、酸化物及びカルボン酸塩が、2軸スクリュー押出機で融解配合される。
該組成物は、射出成形、押出、熱成形、機械加工、及び吹込成形のための標準的方法によってさらに処理することができる。コーティング及び膜のための溶液に基づく処理も可能である。上記の組成物を含む最終的な物品は、超音波溶接、接着、及びレーザーマーキング、並びにヒートステーキング、ねじ切り、及び機械加工などの標準的な後二次加工操作に付すことができる。
Optionally, fillers, lubricants, heat stabilizers, antistatic agents, fillers, reinforcing agents, organic and / or inorganic pigments, for example TiO 2, carbon black, flame retardants and smoke suppressants, during compounding process It can be added to the composition.
Preferably, polymer (P), oxide and carboxylate are melt compounded in a twin screw extruder.
The composition can be further processed by standard methods for injection molding, extrusion, thermoforming, machining, and blow molding. Solution-based processing for coatings and films is also possible. The final article comprising the above composition can be subjected to standard post-processing operations such as ultrasonic welding, adhesion, and laser marking, and heat staking, threading, and machining.
本発明の別の目的は、上記のポリマー組成物を含む物品である。
有利には、該物品が、射出成形物品、押出成形物品、成形物品、コーティング物品又はキャスト物品である。好ましくは、射出成形物品である。
本発明の物品は、標準的な方法により上記のように該組成物を処理することよって製造することができる。
本発明は、実施例を参照することによって以下により詳細に記載される;しかし、本発明はこれらの実施例に限定されない。
Another object of the present invention is an article comprising the polymer composition described above.
Advantageously, the article is an injection molded article, an extruded article, a molded article, a coated article or a cast article. Preferably, it is an injection molded article.
Articles of the invention can be manufactured by treating the composition as described above by standard methods.
The invention is described in more detail below by reference to examples; however, the invention is not limited to these examples.
実施例１〜５
原材料:
Solvay Advanced Polymers, L.L.C.から市場で入手可能なRADEL(登録商標)R 5600 ポリフェニルスルホンは、4,4'-ジハロジフェニルスルホン及び4,4'-ジヒドロキシジフェニルの重縮合から得られるポリフェニルスルホンである。
配合:
酸化亜鉛、ステアリン酸亜鉛及びステアリン酸マグネシウムを、RADEL(登録商標)R 5600 ポリフェニルスルホンペレットと混合し、及び33/1のL/D比を有する25mm直径の2軸スクリュー二重通気式Berstorff押出機を用いて融解配合した。実施例で用いた量の詳細は、表１で報告する。
Examples 1-5
raw materials:
RADEL® R 5600 polyphenylsulfone commercially available from Solvay Advanced Polymers, LLC is a polyphenylsulfone obtained from the polycondensation of 4,4'-dihalodiphenylsulfone and 4,4'-dihydroxydiphenyl. is there.
Formula:
Zinc oxide, zinc stearate and magnesium stearate are mixed with RADEL® R 5600 polyphenylsulfone pellets and 25 mm diameter twin screw double vented Berstorff extrusion with L / D ratio of 33/1 This was melted and blended using a machine. Details of the amounts used in the examples are reported in Table 1.
イオン抽出及び分析測定
各調合物、並びにRADEL(登録商標)R 5600 ポリフェニルスルホン単独から配合されたペレットのサンプルを、以下の手順によるイオン抽出に付した:
1.0gのサンプルを5.0mLの18mΩの水(Alltech Associates, Inc.から入手可能なMilli-Q)に入れた。続いて、該サンプルを85℃で24時間オーブンに入れ、イオンを抽出した。
24時間後、該ペレットを分離し、以下の分析システムを用いて水相をIC(イオンクロマトグラフィー)によって分析した:
Dionex DX500 クロマトグラフィーシステム;
Dionex GP50 標準的なボア勺配ポンプ;
Dionex ASRS Ultra 4mm サプレッサー;
Dionex CD20 伝導率検出器;
Dionex AS11A カラム, 4mm;
Dionex AG11A 保護カラム, 4mm;
Dionex AS40 オートサンプラー, Inert Peek Flow Path.
用いた溶出液は、EG40 Eluent Generatorによって提供される18mΩの水、0.2-0.4mM KOHである。
イオンクロマトグラフィーは、各イオンの5点検量線の最小値を用いて定量化した。
結果を表１に加える。
Ion Extraction and Analytical Measurements Samples of each formulation and pellets formulated from RADEL® R 5600 polyphenylsulfone alone were subjected to ion extraction by the following procedure:
1.0 g of sample was placed in 5.0 mL of 18 mΩ water (Milli-Q available from Alltech Associates, Inc.). Subsequently, the sample was placed in an oven at 85 ° C. for 24 hours to extract ions.
After 24 hours, the pellets were separated and the aqueous phase was analyzed by IC (ion chromatography) using the following analytical system:
Dionex DX500 chromatography system;
Dionex GP50 standard bore distribution pump;
Dionex ASRS Ultra 4mm suppressor;
Dionex CD20 conductivity detector;
Dionex AS11A column, 4mm;
Dionex AG11A protection column, 4mm;
Dionex AS40 Autosampler, Inert Peek Flow Path.
The eluent used is 18 mΩ water, 0.2-0.4 mM KOH provided by EG40 Eluent Generator.
Ion chromatography was quantified using the minimum value of the 5 check curve for each ion.
The results are added to Table 1.
表１
実施例６〜８:
原材料:
Solvay Advanced Polymers, L.L.C.から市場で入手可能なUDEL(登録商標)P3703 ポリスルホンは、4,4'-ジハロジフェニルスルホン及びビスフェノールAの重縮合から得られるポリスルホンである。
配合:
酸化亜鉛及びステアリン酸亜鉛を、UDEL(登録商標)P3703 ポリスルホンペレットと混合し、及び33/1のL/D比を有する25mm直径の2軸スクリュー二重通気式Berstorff押出機を用いて融解配合した。実施例で用いた量の詳細は、表２で報告する。
イオン抽出及び分析測定
実施例１〜５と同様の手順を、実施例７及び８の組成物、並びにUDEL(登録商標)P3703 ポリスルホン単独(比較例６)で繰り返した。結果を表２に加える。
Examples 6-8:
raw materials:
UDEL® P3703 polysulfone commercially available from Solvay Advanced Polymers, LLC is a polysulfone obtained from the polycondensation of 4,4′-dihalodiphenylsulfone and bisphenol A.
Formula:
Zinc oxide and zinc stearate were mixed with UDEL® P3703 polysulfone pellets and melt compounded using a 25 mm diameter twin screw double vented Berstorff extruder with an L / D ratio of 33/1. . Details of the amounts used in the examples are reported in Table 2.
Ion Extraction and Analytical Measurements The same procedure as Examples 1-5 was repeated with the compositions of Examples 7 and 8 and UDEL® P3703 polysulfone alone (Comparative Example 6). The results are added to Table 2.
表２
Claims (11)
-該組成物の全質量に基づいて90質量%よりも多い少なくとも1種の芳香族スルホンポリマー(P)、ここで該芳香族スルホンポリマー(P)の繰り返し単位の少なくとも5質量%は少なくとも1つの式1の基を含む；
-該組成物の全質量に基づいて少なくとも0.005質量%の、少なくとも10個の炭素原子を含む、少なくとも1種の金属カルボン酸塩
を含み、前記金属酸化物及び前記金属カルボン酸塩の間の質量比が、0.05〜1質量/質量である、芳香族高ガラス転移温度スルホンポリマー組成物。 An aromatic high glass transition temperature sulfone polymer composition comprising:
More than 90% by weight of at least one aromatic sulfone polymer (P) based on the total weight of the composition, wherein at least 5% by weight of the repeating units of the aromatic sulfone polymer (P) is at least one Including a group of formula 1;
At least one metal carboxylate comprising at least 0.005% by weight, based on the total weight of the composition, of at least 10 carbon atoms
Hints, the mass ratio between the metal oxide and the metal carboxylate salt is from 0.05 to 1 weight / weight, aromatic high glass transition temperature sulfone polymer composition.
-Qは以下の構造の中から選択される基であり:
及びそれらの混合物;
-Arは以下の構造の中から選択される基であり:
及びそれらの混合物;
-Ar'は以下の構造の中から選択される基である。
及びそれらの混合物)。The aromatic high glass according to any one of claims 1 to 5, wherein at least 5% by mass of the repeating unit of the aromatic sulfone polymer (P) is the repeating unit (R2) and / or the repeating unit (R3). Transition temperature sulfone polymer composition.
-Q is a group selected from the following structures:
And mixtures thereof;
-Ar is a group selected from the following structures:
And mixtures thereof;
-Ar 'is a group selected from the following structures.
And mixtures thereof).
-金属酸化物;
-金属カルボン酸塩:
を混合することを含む、請求項１〜９のいずれか１項に記載の高ガラス転移温度スルホンポリマー組成物を製造するための方法。-Aromatic sulfone polymer (P);
-Metal oxides;
-Metal carboxylates:
10. A method for producing a high glass transition temperature sulfone polymer composition according to any one of claims 1 to 9 , comprising mixing.
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| US61502504P | 2004-10-04 | 2004-10-04 | |
| US60/615,025 | 2004-10-04 | ||
| EP05101408.2 | 2005-02-24 | ||
| EP05101408A EP1695994B1 (en) | 2005-02-24 | 2005-02-24 | Aromatic high glass temperature sulfone polymer composition |
| PCT/EP2005/054975 WO2006037773A1 (en) | 2004-10-04 | 2005-10-03 | Aromatic high glass transition temperature sulfone polymer composition |
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| EP2256136A1 (en) * | 2009-05-05 | 2010-12-01 | Sanofi-Aventis | Novel acylated decasaccharides and their use as antithrombotic agents |
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| JPS5714849A (en) * | 1980-06-30 | 1982-01-26 | Fuji Photo Film Co Ltd | Transfer film for electrophotographic copier |
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| JPS6375060A (en) * | 1986-09-19 | 1988-04-05 | Asahi Glass Co Ltd | Molded aromatic polysulfone based polymer article |
| JPH062879B2 (en) * | 1988-12-19 | 1994-01-12 | 住友化学工業株式会社 | Method for producing aromatic polysulfone resin molding material with improved releasability |
| DE3932882A1 (en) * | 1989-10-02 | 1991-04-11 | Siemens Ag | WELL HEAT-CONDUCTING COMPOSITE |
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| JP3968864B2 (en) * | 1998-03-31 | 2007-08-29 | 住友化学株式会社 | Thermoplastic resin composition, production method and molded product |
| JP2003041147A (en) * | 2001-05-18 | 2003-02-13 | Showa Denko Kk | Coated zinc oxide particle, method for producing the same and application thereof |
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