JP2020504775A - ケイ素含有ハロゲン化エラストマー - Google Patents
ケイ素含有ハロゲン化エラストマー Download PDFInfo
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- JP2020504775A JP2020504775A JP2019535354A JP2019535354A JP2020504775A JP 2020504775 A JP2020504775 A JP 2020504775A JP 2019535354 A JP2019535354 A JP 2019535354A JP 2019535354 A JP2019535354 A JP 2019535354A JP 2020504775 A JP2020504775 A JP 2020504775A
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- silicon
- halogenated
- surface layer
- halogen
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- 239000010703 silicon Substances 0.000 title claims abstract description 40
- 229920001971 elastomer Polymers 0.000 title claims abstract description 30
- 239000000806 elastomer Substances 0.000 title claims abstract description 22
- 239000000203 mixture Substances 0.000 claims abstract description 82
- 239000002210 silicon-based material Substances 0.000 claims abstract description 48
- 239000002344 surface layer Substances 0.000 claims abstract description 46
- 239000002253 acid Substances 0.000 claims abstract description 36
- 229920006125 amorphous polymer Polymers 0.000 claims abstract description 33
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 25
- 150000002367 halogens Chemical class 0.000 claims abstract description 24
- 150000001875 compounds Chemical class 0.000 claims description 42
- 229910052731 fluorine Inorganic materials 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 13
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- 150000002978 peroxides Chemical class 0.000 claims description 10
- 229930185605 Bisphenol Natural products 0.000 claims description 9
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 9
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- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 claims description 5
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- 125000000217 alkyl group Chemical group 0.000 description 7
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- 125000001153 fluoro group Chemical group F* 0.000 description 6
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
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- 238000012360 testing method Methods 0.000 description 5
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- 229910018557 Si O Inorganic materials 0.000 description 4
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- 125000001931 aliphatic group Chemical group 0.000 description 4
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- 230000003247 decreasing effect Effects 0.000 description 4
- 238000000113 differential scanning calorimetry Methods 0.000 description 4
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- 229910021485 fumed silica Inorganic materials 0.000 description 4
- 239000005350 fused silica glass Substances 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 235000012239 silicon dioxide Nutrition 0.000 description 4
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- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 3
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- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
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- KSMYREBPTSSZDR-UHFFFAOYSA-M tributyl(prop-2-enyl)phosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CC=C KSMYREBPTSSZDR-UHFFFAOYSA-M 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/14—Peroxides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—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 a halogen; Compositions of derivatives of such polymers
- C08L27/02—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 a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L27/04—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 a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
- C08L27/06—Homopolymers or copolymers of vinyl chloride
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—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 a halogen; Compositions of derivatives of such polymers
- C08L27/02—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 a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L27/12—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 a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
- C08L27/16—Homopolymers or copolymers or vinylidene fluoride
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
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Abstract
Description
(a)少なくとも25重量%のハロゲンを有するハロゲン化非晶質ポリマーと、
(b)少なくとも0.5phrの酸受容体と、
(c)少なくとも0.01phrのケイ素含有化合物と、
(d)脱ハロゲン化水素硬化系と、
を含む、硬化性ハロゲン化非晶質ポリマー組成物が記載される。
ケイ素を含む表面層を有するハロゲン化エラストマーを含む物品であって、バルク中に少なくとも0.01phrのケイ素含有無機化合物を含み、表面層からバルクに向かって減少する二酸化ケイ素の濃度勾配が存在する、ハロゲン化エラストマーが記載される。
「a」、「an」、及び「the」という用語は、互換的に使用され、1以上を意味し、
「及び/又は」は、述べられた事例の一方又は両方が起こり得ることを示すために使用され、例えば、A及び/又はBは、(A及びB)と(A又はB)とを含み、
「主鎖」とは、ポリマーの主な連続鎖を指し、
「コポリマー」は、ターポリマー又はクワドポリマーなどの、明示的に列挙されていない他のモノマー(コモノマー)から誘導される他の繰り返し単位が存在する選択肢を除外することなく、列挙されたモノマー(コモノマー)から誘導される繰り返し単位を含むポリマーを指す。
「架橋」とは、予め形成した2つのポリマー鎖を、化学結合又は化学的な基を使用して連結することを指す。
「共重合」とは、モノマーが一緒に重合されてポリマー主鎖を形成することを指す。
「モノマー」は、重合を経てその後ポリマーの基本的構造の部分を形成することができる分子である。
「有機」は、当該技術分野において一般的な意味を有し、例えば、有機化合物は、炭化物、酸化炭素、二硫化炭素などの二元化合物;金属シアン化物、ホスゲン、硫化カルボニルなどの三元化合物、及び炭酸カルシウムなどの金属炭酸塩が挙げられる、いくつかの例外/除外を有する炭素含有化合物である。
「全フッ素化」とは、全ての水素原子がフッ素原子に置換されている、炭化水素から得られる基又は化合物を意味する。しかし、全フッ素化化合物は、酸素原子、塩素原子、臭素原子及びヨウ素原子のような、フッ素原子及び炭素原子以外の原子を更に含有してもよい。
「ポリマー」は、少なくとも20,000ダルトン、少なくとも3,000ダルトン、少なくとも50,000ダルトン、少なくとも100,000ダルトン、少なくとも300,000ダルトン、少なくとも500,000ダルトン、少なくとも750,000ダルトン、少なくとも1,000,000ダルトン又は更には少なくとも1,500,000ダルトンであり、かつポリマーの早期ゲル化を引き起こすほどには高くない分子量の数平均分子量(Mn)を有するマクロ構造を指す。
CF2=CF−O−Rf
式中、Rfは、1個以上の酸素原子を含有してもよい全フッ素化脂肪族基を表す。
CF2=CFO(Ra fO)n(Rb fO)mRc f
式中、Ra f及びRb fは、炭素原子が1〜6個、特に炭素原子が2〜6個の異なる直鎖状又は分岐状ペルフロオロアルキレン基であり、m及びnは、独立して、0〜10であり、Rc fは、炭素原子が1〜6個のペルフルオロアルキル基である。全フッ素化ビニルエーテルの特定の例としては、ペルフルオロ(メチルビニル)エーテル(PMVE)、ペルフルオロ(エチルビニル)エーテル(PEVE)、ペルフルオロ(n−プロピルビニル)エーテル(PPVE−1)、ペルフルオロ−2−プロポキシプロピルビニルエーテル(PPVE−2)、ペルフルオロ−3−メトキシ−n−プロピルビニルエーテル、ペルフルオロ−2−メトキシ−エチルビニルエーテル、及びCF3−(CF2)2−O−CF(CF3)−CF2−O−CF(CF3)−CF2−O−CF=CF2が挙げられる。
CF2=CF−Rd f 又は CH2=CH−Rd f
式中、Rd fは、炭素原子が1〜10個、好ましくは1〜5個のペルフルオロアルキル基を表す。フルオロアルキルビニルモノマーの典型的な例は、ヘキサフルオロプロピレンである。
(a)以下の式を有するブロモ−又はヨード−(ペル)フルオロアルキル−(ペル)フルオロビニルエーテル:
Z−Rf−O−CX=CX2
[式中、各Xは、同じであっても異なっていてもよく、H又はFを表し、Zは、Br又はIであり、Rfは、任意選択で塩素及び/又はエーテル酸素原子を含有する(ペル)フルオロアルキレンC1〜C12であり、例えば、BrCF2−O−CF=CF2、BrCF2CF2−O−CF=CF2、BrCF2CF2CF2−O−CF=CF2、CF3CFBrCF2−O−CF=CF2、ICF2CF2CH=CH2、ICF2CF2CF2−O−CF=CF2などである]、
(b)以下の式を有するものなどの、ブロモ−又はヨードペルフルオロオレフィン:
Z’−(Rf’)r−CX=CX2
[式中、各Xは、独立して、H又はFを表し、Z’は、Br又はIであり、R’fは、任意選択で塩素原子を含有するペルフルオロアルキレンC1〜C12であり、rは、0又は1であり、例えば、ブロモトリフルオロエチレン、4−ブロモ−ペルフルオロブテン−1など、又は1−ブロモ−2,2−ジフルオロエチレン及び4−ブロモ−3,3,4,4−テトラフルオロブテン−1などのブロモフルオロオレフィンである]、
(c)臭化ビニル及び4−ブロモ−1−ブテンなどの非フッ素化ブロモ−オレフィン
が挙げられる。
トリフェニルベンジルホスホニウムクロリド
トリブチルアリルホスホニウムクロリド
トリブチルベンジルアンモニウムクロリド
テトラブチルアンモニウムブロミド
トリアリールスルホニウムクロリド
8−ベンジル−1,8ジアザビシクロ[5,4,0]−7−ウンデセニウムクロリド
ベンジルトリス(ジメチルアミノ)ホスホニウムクロリド、及び
ベンジル(ジエチルアミノ)ジフェニルホスホニウムクロリド。
CX1X2=CX3−L−M
式中、X1、X2及びX3は、H、Cl及びFから独立して選択され、X1、X2及びX3のうちの少なくとも1つはHであり、X1、X2及びX3のうちの少なくとも1つはF又はClであり、Lは結合又は連結基であり、Mは求核基である。
(b)少なくとも0.5phrの酸受容体と、
(c)少なくとも0.1phrのケイ素含有化合物と、
(d)脱ハロゲン化水素硬化系と、
を含む、硬化性ハロゲン化非晶質ポリマー組成物。
(b)少なくとも0.5〜最大10phrの酸受容体と、
(c)少なくとも0.01phrのケイ素含有化合物と、
(d)脱ハロゲン化水素硬化系と、
を含む、硬化性ハロゲン化非晶質ポリマー組成物。
(式中、X1、X2及びX3は、H、Cl及びFから独立して選択され、X1、X2及びX3のうちの少なくとも1つはHであり、少なくとも1つはF又はClである)、並びに(iv)これらの組み合わせのうちの少なくとも1つを含む、実施形態1〜16のいずれか1つに記載の組成物。
(a)実施形態1〜21のいずれか1つに記載の組成物を得ることと、
(b)この組成物を少なくとも160℃の温度で少なくとも15分間、無拘束で加熱することと、
を含む製造方法。
Claims (16)
- (a)少なくとも25重量%のハロゲンを有するハロゲン化非晶質ポリマーと、
(b)少なくとも0.5phrかつ10phr未満の酸受容体と、
(c)少なくとも0.01phrのケイ素含有化合物と、
(d)脱ハロゲン化水素硬化系と、
を含む、硬化性ハロゲン化非晶質ポリマー組成物。 - 前記ハロゲン化非晶質ポリマーが、フッ素化非晶質ポリマー又は塩素化非晶質ポリマーである、請求項1に記載の組成物。
- 7phr未満の酸受容体を含む、請求項1又は2に記載の組成物。
- 前記酸受容体が、MgO、Ca(OH)2及びハイドロタルサイトのうちの少なくとも1つを含む、請求項1〜3のいずれか一項に記載の組成物。
- 5phr未満のケイ素含有化合物を含む、請求項1〜4のいずれか一項に記載の組成物。
- 前記脱ハロゲン化水素硬化系が、(i)ビスフェノール硬化系、(ii)アミン系硬化系、(iii)CX1X2=CX3−L−M(式中、X1、X2及びX3は、H、Cl及びFから独立して選択され、X1、X2及びX3のうちの少なくとも1つはHであり、少なくとも1つはF又はClである)、並びに(iv)これらの組み合わせのうちの少なくとも1つを含む、請求項1〜5のいずれか一項に記載の組成物。
- ペルオキシド硬化系を更に含む、請求項1〜6のいずれか一項に記載の組成物。
- 少なくとも0.5phr〜最大4phrの、Ca(OH)2である前記酸受容体、及び少なくとも0.05phr〜最大5phrの前記ケイ素含有化合物を含む、請求項1〜7のいずれか一項に記載の組成物。
- 少なくとも0.5phr〜最大7phrの、MgOである前記酸受容体、及び少なくとも0.05phr〜最大5phrの前記ケイ素含有化合物を含む、請求項1〜7のいずれか一項に記載の組成物。
- 少なくとも0.5phr〜最大5phrの、ハイドロタルサイトである前記酸受容体、及び少なくとも0.05phr〜最大5phrの前記ケイ素含有化合物を含む、請求項1〜7のいずれか一項に記載の組成物。
- ケイ素を含む表面層を有するハロゲン化エラストマーの製造方法であって、
(a)請求項1〜10のいずれか一項に記載の組成物を得ることと、
(b)前記組成物を少なくとも160℃の温度で少なくとも15分間、無拘束で加熱することと、を含む製造方法。 - ケイ素を含む表面層を有するハロゲン化エラストマーを含む物品であって、前記ハロゲン化エラストマーが、バルク中に少なくとも0.01phrのケイ素含有無機化合物を含み、前記表面層から前記バルクに向かって減少する二酸化ケイ素の濃度勾配が存在する、物品。
- ハロゲン化エラストマーを含む物品であって、前記ハロゲン化エラストマーの第1の主面が、ケイ素を含む表面層を有し、かつ波状である、物品。
- 硬化した請求項1〜10のいずれか一項に記載の組成物を含むエラストマー物品であって、前記バルクのケイ素含有量の少なくとも2倍であるケイ素含有量を、前記エラストマー物品の表面に含む、エラストマー物品。
- ハロゲン含有非晶質ポリマー化合物であって、表面層をその上に有するバルク部分を含み、前記表面層が第1のSi対ハロゲン重量比を有し、前記バルク部分が第2のSi対ハロゲン重量比を有し、前記第1の重量比が前記第2の重量比よりも大きく、Si対ハロゲンの前記重量比が前記表面層から前記バルク部分へ徐々に減少する、ハロゲン含有非晶質ポリマー化合物。
- (a)少なくとも25重量%のハロゲンを有し、部分的にハロゲン化されている、ハロゲン化非晶質ポリマー、(b)最大で4phrの、二価金属の酸化物又は水酸化物から選択される酸受容体、及び(c)少なくとも0.05かつ最大5phrのケイ素含有化合物を含む組成物を、ビスフェノール硬化系により硬化することによって得られる、硬化物品。
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- 2017-12-22 CN CN201780081417.7A patent/CN110168002A/zh active Pending
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KR102448558B1 (ko) | 2022-09-28 |
WO2018125790A1 (en) | 2018-07-05 |
US20190330444A1 (en) | 2019-10-31 |
KR20190099437A (ko) | 2019-08-27 |
US11326040B2 (en) | 2022-05-10 |
EP3562876A1 (en) | 2019-11-06 |
CN110168002A (zh) | 2019-08-23 |
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