JP2020530040A - メチルメタクリレート、(メタ)アクリル酸及びスチレンモノマーを含むコポリマーを含む組成物 - Google Patents
メチルメタクリレート、(メタ)アクリル酸及びスチレンモノマーを含むコポリマーを含む組成物 Download PDFInfo
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- JP2020530040A JP2020530040A JP2020503848A JP2020503848A JP2020530040A JP 2020530040 A JP2020530040 A JP 2020530040A JP 2020503848 A JP2020503848 A JP 2020503848A JP 2020503848 A JP2020503848 A JP 2020503848A JP 2020530040 A JP2020530040 A JP 2020530040A
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- polymer
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- methyl methacrylate
- acrylic acid
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- 239000000178 monomer Substances 0.000 title claims abstract description 36
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- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 229920001577 copolymer Polymers 0.000 title description 15
- 229920000642 polymer Polymers 0.000 claims abstract description 37
- 238000000034 method Methods 0.000 claims description 23
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- 238000006116 polymerization reaction Methods 0.000 claims description 11
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 8
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- 125000003545 alkoxy group Chemical group 0.000 description 2
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- 238000000071 blow moulding Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
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- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
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- WRXCBRHBHGNNQA-UHFFFAOYSA-N (2,4-dichlorobenzoyl) 2,4-dichlorobenzenecarboperoxoate Chemical compound ClC1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1Cl WRXCBRHBHGNNQA-UHFFFAOYSA-N 0.000 description 1
- HGXJDMCMYLEZMJ-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOOC(=O)C(C)(C)C HGXJDMCMYLEZMJ-UHFFFAOYSA-N 0.000 description 1
- KDGNCLDCOVTOCS-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy propan-2-yl carbonate Chemical compound CC(C)OC(=O)OOC(C)(C)C KDGNCLDCOVTOCS-UHFFFAOYSA-N 0.000 description 1
- NOBYOEQUFMGXBP-UHFFFAOYSA-N (4-tert-butylcyclohexyl) (4-tert-butylcyclohexyl)oxycarbonyloxy carbonate Chemical compound C1CC(C(C)(C)C)CCC1OC(=O)OOC(=O)OC1CCC(C(C)(C)C)CC1 NOBYOEQUFMGXBP-UHFFFAOYSA-N 0.000 description 1
- FYRCDEARNUVZRG-UHFFFAOYSA-N 1,1,5-trimethyl-3,3-bis(2-methylpentan-2-ylperoxy)cyclohexane Chemical compound CCCC(C)(C)OOC1(OOC(C)(C)CCC)CC(C)CC(C)(C)C1 FYRCDEARNUVZRG-UHFFFAOYSA-N 0.000 description 1
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- 230000008018 melting Effects 0.000 description 1
- 239000000113 methacrylic resin Substances 0.000 description 1
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical class CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 1
- SRSFOMHQIATOFV-UHFFFAOYSA-N octanoyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(=O)CCCCCCC SRSFOMHQIATOFV-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000001902 propagating effect Effects 0.000 description 1
- LLLWBIRGAQXDLV-UHFFFAOYSA-N propan-2-yl 2,4,4-trimethylpentan-2-ylperoxy carbonate Chemical compound C(OOOC(CC(C)(C)C)(C)C)(OC(C)C)=O LLLWBIRGAQXDLV-UHFFFAOYSA-N 0.000 description 1
- AHIHJODVQGBOND-UHFFFAOYSA-N propan-2-yl hydrogen carbonate Chemical compound CC(C)OC(O)=O AHIHJODVQGBOND-UHFFFAOYSA-N 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical class CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 239000003017 thermal stabilizer Substances 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 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
- C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
- C08L25/02—Homopolymers or copolymers of hydrocarbons
- C08L25/04—Homopolymers or copolymers of styrene
- C08L25/08—Copolymers of styrene
- C08L25/14—Copolymers of styrene with unsaturated esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C45/00—Injection moulding, i.e. forcing the required volume of moulding material through a nozzle into a closed mould; Apparatus therefor
- B29C45/0001—Injection moulding, i.e. forcing the required volume of moulding material through a nozzle into a closed mould; Apparatus therefor characterised by the choice of material
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/08—Styrene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/04—Acids; Metal salts or ammonium salts thereof
- C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/10—Homopolymers or copolymers of methacrylic acid esters
- C08L33/12—Homopolymers or copolymers of methyl methacrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2438/00—Living radical polymerisation
- C08F2438/02—Stable Free Radical Polymerisation [SFRP]; Nitroxide Mediated Polymerisation [NMP] for, e.g. using 2,2,6,6-tetramethylpiperidine-1-oxyl [TEMPO]
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2500/00—Characteristics or properties of obtained polyolefins; Use thereof
- C08F2500/12—Melt flow index or melt flow ratio
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
- C08F2800/20—Copolymer characterised by the proportions of the comonomers expressed as weight or mass percentages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
Abstract
Description
熱可塑性ポリマー及びコポリマー、特に(メタ)アクリルポリマーは、優れた透明性、良好な機械的特性及び機械加工特性を有し、自動車部品、電気部品、工業部品、光学材料、家電製品の様々な部品、審美的部品、その他の物品などのような様々な分野で広く使用されている。
・85%から92%、好ましくは88%から92%の間、より好ましくは88%から91%の間、有利には88%から90%の間の重量割合のメチルメタクリレート、
・3%から10%、好ましくは5%から9%の間、より好ましくは5.5%から8%の間、有利には6%から8%の間の重量割合のスチレン、
・3%から6%、好ましくは3.5%から5%の間、有利には4%から5%の間の重量割合のメタクリル酸及び/又はアクリル酸を含む。理想的には、メタクリル酸の割合は4%から4.9%である。
a)以下の3つのモノマー:
a1)85%から92%、好ましくは88%から92%の間、より好ましくは88%から91%の間、有利には88%から90%の間の重量割合のメチルメタクリレート、
a2)3%から10%、好ましくは5%から9%の間、より好ましくは5.5%から8%の間、有利には6%から8%の間の重量割合のスチレン、
a3)3%から6%、好ましくは3.5%から5%の間、有利には4%から5%の間の重量割合のメタクリル酸及び/又はアクリル酸、有利には、4%から4.9%の割合のメタクリル酸、
を含む混合物(全ての割合は、3つのモノマーa1)、a2)及びa3)の合計に対する)を調製する工程と、
b)工程a)で得られた混合物を重合する工程と、
を含む。
上式中、ラジカルRLは15.0342g/molを超えるモル質量を有する。ラジカルRLは、15.0342を超えるモル質量を有する限り、塩素、臭素又はヨウ素などのハロゲン原子であっても、飽和若しくは不飽和、直鎖状、分岐状若しくは環状炭化水素系基(例えば、アルキルラジカル又はフェニルラジカル)、又はエステル基−COOR、又はアルコキシル基−OR、又はホスホン酸基−PO(OR)2であってもよい。一価であるラジカルRLは、ニトロキシドラジカルの窒素原子に関してβの位置にあるといわれる。式(1)の炭素原子及び窒素原子の残存する原子価は、種々のラジカル、例えば、水素原子、又は1から10個の炭素原子を含む炭化水素系ラジカル、例えばアルキル、アリール又はアリールアルキルラジカルに結合され得る。式(1)の炭素原子と窒素原子が二価のラジカルを介して環を形成するように結合していることは除外されない。しかし、式(1)の炭素原子と窒素原子の残存する原子価は、好ましくは一価のラジカルに結合している。ラジカルRLは、好ましくは、30g/molを超えるモル質量を有する。ラジカルRLは、例えば、40から450g/molのモル質量を有し得る。例として、ラジカルRLは、ホスホリル基を含むラジカルであってもよく、場合によって前記ラジカルRLは、以下の式:
により表され、上式中、R1及びR2(これらは同一でも異なっていてもよい)は、アルキル、シクロアルキル、アルコキシル、アリールオキシル、アリール、アラルキルオキシル、ペルフルオロアルキル又はアラルキルラジカルから選択され、1から20個の炭素原子を含み得る。R1及び/又はR2はまた、塩素又は臭素又はフッ素又はヨウ素原子のようなハロゲン原子であってもよい。ラジカルRLはまた、例えばフェニルラジカル又はナフチルラジカルについては少なくとも一の芳香環を含んでもよく、場合によって前記環は、例えば1から4個の炭素原子を含むアルキルラジカルで置換されている。
・N−(tert−ブチル)−1−フェニル−2−メチルプロピルニトロキシド、
・N−(tert−ブチル)−1−(2−ナフチル)−2−メチルプロピルニトロキシド、
・N−(tert−ブチル)−1−ジエチルホスホノ−2,2−ジメチルプロピルニトロキシド、
・N−(tert−ブチル)−1−ジベンジルホスホノ−2,2−ジメチルプロピルニトロキシド、
・N−フェニル−1−ジエチルホスホノ−2,2−ジメチルプロピルニトロキシド、
・N−フェニル−1−ジエチルホスホノ−1−メチルエチルニトロキキシド、
・N−(1−フェニル−2−メチルプロピル)−1−ジエチルホスホノ−1−メチルエチルニトロキシド、
・4−オキソ−2,2,6,6-テトラメチル-1-ピペリジニルオキシ、
・2,4,6−トリ−tert−ブチルフェノキシ ニトロキシド、
・N−(tert−ブチル)−1−ジエチルホスホノ−2,2−ジメチルプロピルニトロキシド。
・本発明の方法により生成された(メタ)アクリルコポリマーを含む組成物を溶融する工程、
・溶融された組成物を型に射出する工程、
・少なくとも型が完全に溶融された組成物で満たされるまで、型に圧力を加える工程。
Claims (14)
- 成形物体又は射出成形物体又は押出物体の製造に適したポリマー組成物であって、前記ポリマーが、85%から92%の間の重量割合のメチルメタクリレート、3%から10%の間の重量割合のスチレン、3%から6%の間の割合のアクリル酸及び/又はメタクリル酸から選択されるモノマーを含む、組成物。
- スチレンが前記ポリマー中に5%から9%の間の重量割合で含まれていることを特徴とする、請求項1に記載の組成物。
- メタクリル酸及び/又はアクリル酸が前記ポリマー中に3.5%から5%の間の重量割合で含まれていることを特徴とする、請求項1に記載の組成物。
- 前記ポリマーが、以下
・88%から92%の間、より好ましくは88%から90%の間で変化する重量割合のメチルメタクリレート、
・5%から9%の間、より好ましくは5.5%から8%の間で変化する重量割合のスチレン、
・3.5%から5%の間で変化する重量割合のメタクリル酸及び/又はアクリル酸
のモノマーを含むことを特徴とする、請求項1に記載の組成物。 - ラジカル重合により調製されている、請求項1から4のいずれか一項に記載の組成物。
- 制御ラジカル重合により調製されている、請求項1から4のいずれか一項に記載の組成物。
- 3.5g/10分から7g/10分の間のメルトフローインデックスを有する、請求項1から6のいずれか一項に記載の組成物。
- 110℃から120℃の間のビカット軟化温度を有する、請求項1から6のいずれか一項に記載の組成物。
- 請求項1から8のいずれか一項に記載のポリマー組成物を調製するための方法であって、以下の工程:
a)以下の3つのモノマー:
a1)85%から92%、好ましくは88%から92%の間、より好ましくは88%から91%の間、有利には88%から90%の間の重量割合のメチルメタクリレート、
a2)3%から10%、好ましくは5%から9%の間、より好ましくは5.5%から8%の間、有利には6%から8%の間の重量割合のスチレン、
a3)3%から6%、好ましくは3.5%から5%の間、有利には4%から5%の間の重量割合のメタクリル酸及び/又はアクリル酸、有利には、4%から4.9%の割合のメタクリル酸、
を含む混合物(全ての割合は、3つのモノマーa1)、a2)及びa3)の合計に対する)を調製する工程と、
b)工程a)で得られた混合物を重合する工程と、
を含む、方法。 - 重合がラジカル方式で行われることを特徴とする、請求項9に記載の方法。
- 重合が制御ラジカル方式で行われることを特徴とする、請求項9に記載の方法。
- 請求項1から8のいずれか一項に記載の組成物から製造される成形又は押出成形物体。
- シート、ブロック、フィルム、管又はプロファイル要素の形態の、請求項12に記載の物体。
- 導光体、レンズ、装飾用自動車部品、前後の自動車用ヘッドランプ部品、テールライト、ランプカバー、ダッシュボードウィンドウ、骨材、オーブンの正面、家電製品の部品、光学フィルム、装飾フィルム、共押出多層構造体の上部保護層から選択される、請求項12又は13に記載の物体。
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PCT/FR2018/051944 WO2019025709A1 (fr) | 2017-07-31 | 2018-07-27 | Composition comprenant un copolymere comprenant des monomeres de methacrylate de methyle, d'acides (meth) acrylique et de monomeres styreniques |
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2017
- 2017-07-31 FR FR1757288A patent/FR3069549B1/fr active Active
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2018
- 2018-07-27 EP EP18765946.1A patent/EP3661987A1/fr active Pending
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- 2018-07-27 WO PCT/FR2018/051944 patent/WO2019025709A1/fr unknown
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JPS58125712A (ja) * | 1982-01-20 | 1983-07-26 | Asahi Chem Ind Co Ltd | 耐熱性アクリル樹脂共重合体 |
JPS5941349A (ja) * | 1982-09-01 | 1984-03-07 | Mitsubishi Rayon Co Ltd | 難燃性アクリル系樹脂組成物およびその製造方法 |
JPH0243207A (ja) * | 1989-06-21 | 1990-02-13 | Asahi Chem Ind Co Ltd | 変性共重合体 |
WO2004036112A1 (ja) * | 2002-10-17 | 2004-04-29 | Mitsubishi Rayon Co., Ltd. | 車両用部品 |
US20080261019A1 (en) * | 2005-10-24 | 2008-10-23 | Arkema Inc. | Pvc/Wood Composite |
JP2014111740A (ja) * | 2012-11-02 | 2014-06-19 | Asahi Kasei Chemicals Corp | 熱可塑性樹脂の製造方法 |
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WO2019025709A1 (fr) | 2019-02-07 |
US20200277482A1 (en) | 2020-09-03 |
EP3661987A1 (fr) | 2020-06-10 |
FR3069549B1 (fr) | 2020-10-02 |
FR3069549A1 (fr) | 2019-02-01 |
KR102647458B1 (ko) | 2024-03-13 |
CN110914318A (zh) | 2020-03-24 |
JP7329495B2 (ja) | 2023-08-18 |
KR20200037293A (ko) | 2020-04-08 |
US11634572B2 (en) | 2023-04-25 |
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