JP2010043257A - 炭化水素ポリマー添加物を添加した、優れた不透過性を有するエラストマ組成物 - Google Patents
炭化水素ポリマー添加物を添加した、優れた不透過性を有するエラストマ組成物 Download PDFInfo
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- JP2010043257A JP2010043257A JP2009182629A JP2009182629A JP2010043257A JP 2010043257 A JP2010043257 A JP 2010043257A JP 2009182629 A JP2009182629 A JP 2009182629A JP 2009182629 A JP2009182629 A JP 2009182629A JP 2010043257 A JP2010043257 A JP 2010043257A
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- elastomer composition
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- 239000000203 mixture Substances 0.000 title claims abstract description 266
- 229920000642 polymer Polymers 0.000 title claims abstract description 72
- 239000000654 additive Substances 0.000 title claims abstract description 35
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- 239000004215 Carbon black (E152) Substances 0.000 title claims abstract description 30
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 30
- 230000000996 additive effect Effects 0.000 title claims abstract description 28
- 229920001971 elastomer Polymers 0.000 claims abstract description 214
- 239000000806 elastomer Substances 0.000 claims abstract description 157
- 239000004927 clay Substances 0.000 claims abstract description 82
- 150000005673 monoalkenes Chemical class 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims description 51
- 238000002156 mixing Methods 0.000 claims description 51
- -1 vorconskite Chemical compound 0.000 claims description 45
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 41
- 239000000945 filler Substances 0.000 claims description 24
- 125000004122 cyclic group Chemical group 0.000 claims description 23
- 230000004888 barrier function Effects 0.000 claims description 22
- 239000000463 material Substances 0.000 claims description 19
- 239000000377 silicon dioxide Substances 0.000 claims description 19
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 claims description 18
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- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims description 12
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 9
- 239000000454 talc Substances 0.000 claims description 7
- 229910052623 talc Inorganic materials 0.000 claims description 7
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 6
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 claims description 6
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 5
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- KWLMIXQRALPRBC-UHFFFAOYSA-L hectorite Chemical compound [Li+].[OH-].[OH-].[Na+].[Mg+2].O1[Si]2([O-])O[Si]1([O-])O[Si]([O-])(O1)O[Si]1([O-])O2 KWLMIXQRALPRBC-UHFFFAOYSA-L 0.000 claims description 5
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- VNSBYDPZHCQWNB-UHFFFAOYSA-N calcium;aluminum;dioxido(oxo)silane;sodium;hydrate Chemical compound O.[Na].[Al].[Ca+2].[O-][Si]([O-])=O VNSBYDPZHCQWNB-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
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- XCOBTUNSZUJCDH-UHFFFAOYSA-B lithium magnesium sodium silicate Chemical compound [Li+].[Li+].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Na+].[Na+].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3 XCOBTUNSZUJCDH-UHFFFAOYSA-B 0.000 claims description 4
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- 239000008107 starch Substances 0.000 claims description 3
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- 239000004408 titanium dioxide Substances 0.000 claims description 3
- HPTYUNKZVDYXLP-UHFFFAOYSA-N aluminum;trihydroxy(trihydroxysilyloxy)silane;hydrate Chemical compound O.[Al].[Al].O[Si](O)(O)O[Si](O)(O)O HPTYUNKZVDYXLP-UHFFFAOYSA-N 0.000 claims 2
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- 230000035699 permeability Effects 0.000 abstract description 14
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- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 38
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- 239000003921 oil Substances 0.000 description 25
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 24
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- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 18
- 239000011572 manganese Substances 0.000 description 16
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 15
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 15
- 238000012545 processing Methods 0.000 description 15
- 238000004073 vulcanization Methods 0.000 description 15
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 14
- 229920001577 copolymer Polymers 0.000 description 14
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- 229910052757 nitrogen Inorganic materials 0.000 description 13
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- 238000004132 cross linking Methods 0.000 description 12
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- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 11
- 244000043261 Hevea brasiliensis Species 0.000 description 11
- 239000005062 Polybutadiene Substances 0.000 description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 11
- 229920003052 natural elastomer Polymers 0.000 description 11
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- 239000001301 oxygen Substances 0.000 description 11
- 229910052760 oxygen Inorganic materials 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 10
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- 239000002994 raw material Substances 0.000 description 10
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 9
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- 239000011593 sulfur Substances 0.000 description 9
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 8
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- 239000006057 Non-nutritive feed additive Substances 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
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- 238000004519 manufacturing process Methods 0.000 description 8
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- 229920000181 Ethylene propylene rubber Polymers 0.000 description 7
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- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
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- REBKUVYQFXSVNO-NSCUHMNNSA-N (3E)-1,1-dichloropenta-1,3-diene Chemical group C\C=C\C=C(Cl)Cl REBKUVYQFXSVNO-NSCUHMNNSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
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- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 239000012745 toughening agent Substances 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000004017 vitrification Methods 0.000 description 1
- 239000004636 vulcanized rubber Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
- B60C1/0008—Compositions of the inner liner
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/18—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms
- C08L23/20—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms having four to nine carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L57/00—Compositions of unspecified polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C08L57/02—Copolymers of mineral oil hydrocarbons
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- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
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- Mechanical Engineering (AREA)
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Abstract
ガス透過特性を向上させたエラストマ組成物を提供することである。
【解決手段】
キュアされたエラストマ組成物は、少なくとも一つのC4−C7モノオレフィンエラストマと、炭化水素ポリマー添加物と、クレイとから成り、ある実施例においては、当該キュアされたエラストマ組成物は、40℃における透過流速係数が90 cc*mm/(m2*day)かまたはそれ以下であり、またある実施例においては、当該エラストマ組成物は、実質的にナフテン酸油を含まないことを特徴とする。
【選択図】 なし
Description
エラストマ
メチルスチレン))、ハロゲン化ポリ(イソブチレン-co-p-メチルスチレン)[BIMSM]、ポリブタジエンゴム[BR]、高シス-ポリブタジエン、ポリイソプレンゴム、イソプレン-ブタジエンゴム[IBR]、スチレン-イソプレン-ブタジエンゴム[SIBR]、スチレン-ブタジエンゴム[SBR]、溶液-スチレン-ブタジエンゴム[sSBR]、エマルジョン-スチレン-ブタジエンゴム、ニトリルゴム、エチレン-プロピレンゴム[EP]、エチレン-プロピレンゴム-ジエンゴム[EPDM]、合成ポリイソプレン、一般用途用ゴム、天然ゴム、これらのエラストマのハロゲン化物、およびこれらの混合物。
好適なエラストマには、IIR、ハロゲン化IIR、およびハロゲン化ポリ(イソブチレン-co-p-メチルスチレン)のようなイソブチレンベースのエラストマが含まれる。 有用なエラストマは、公知の適切な手段によって製造することができ、本発明はエラストマを製造する方法によって限定されるものではない。
炭化水素ポリマー添加物
の範囲、あるいは約0℃〜約80℃の範囲、あるいは約40℃〜約60℃の範囲、あるいは約45℃〜約55℃の範囲、あるいは更に好ましくは約48℃〜約53℃の範囲にある。 HPAのTgは示差走査熱量測定(DSC)によって測定することができる。
示差走査熱量測定(DSC)の手順について、以下に説明する。
加熱プレス装置の中へポリマーを入れ、約200℃〜約230℃の温度下でこのポリマーをプレスする。 そしてこのプレスしたシート状のポリマーを、周辺環境条件下の下で冷却するために当該樹脂シートを吊るして置く。 ポンチ型を使って、当該樹脂シートから約6mg〜10mgのサンプルを切り出す。 この6mg〜10mgのサンプルは、室温において80〜100時間の間アニールする。 このアニール期間が終了するときに、このサンプルを示差走査熱量測定(DSC)装置(Perkin Elmer Pyris One Thermal Analysis System製)の中へ入れ、約-50℃〜-70℃まで冷却する。 このサンプルは、約200℃の最終温度になるまで、10℃/分の加熱速度で加熱される。 このサンプルは200℃の温度で5分間保持され、その後2番目の冷却サイクルが行われる。 これらのサイクルの過程で得られるイベントが記録される。 サンプルの溶融ピークより下の温度領域において熱出力が記録される。 そしてこの熱出力は通常、0℃から200℃の間において生じる。 試験(計測)作業中におけるサンプルの吸収エネルギまたは放出エネルギは、ΔHとして表され、ポリマー1g当たりのジュールとして表される。 融点は、サンプルが溶融する範囲内におけるベースラインに対して、最も大きな熱吸収が生じる温度として記録される。
ナノコンポジット(nanocomposite)
望ましいジアミンには、R4R5N-R6-NR7R8の構造式を持つものがある。 ここで、R4,R5,R6,R7,およびR8は等しいか異なり、C1〜C30までのアルキル、又はC2〜C30までのアルキル又はアルケンである。 長鎖のジアミンが必要なときには、少なくとも一つのN-アルキル基またはN-アルケン基が8〜30までの炭素原子を有し、好ましくは、14〜20までの炭素原子を有する。 特に非限定的な例示として、N-coco-1,3-ジアミノプロパン、N-oleyl-1,3-ジアミノプロパン、N-tallow-1,3-ジアミノプロパン、N, N, N’-トリメチル- N’- tallow-1,3-ジアミノプロパンが挙げられる。
が含まれる。 ゴム組成物の技術分野において良く知られているその他の復帰抵抗物質(reversion resistors)としては、ヘキサメチレン ビス(桂皮アルデヒド)がある。
フィラーと添加物
架橋剤、硬化剤、キュアパッケージ、キュアプロセス
プロセス
産業上の応用
実施例1
実施例2
実施例3
Claims (15)
- キュアされたエラストマ組成物であって、
(a) 少なくとも一つのC4−C7モノオレフィンエラストマと、
(b) 炭化水素ポリマー添加物であって、環状成分を備えた炭化水素ポリマー添加物と、
(c) クレイと、
から成り、当該エラストマ組成物が、40℃における透過流速係数が90 cc*mm/(m2*day)かまたはそれ以下であることを特徴とするエラストマ組成物。 - 請求項1に記載のエラストマ組成物であって、前記炭化水素ポリマー添加物が10〜40重量部の範囲で含有されていることを特徴とするエラストマ組成物。
- 請求項1または2に記載のエラストマ組成物であって、当該エラストマ組成物は、炭酸カルシウム、マイカ、シリカ、ケイ酸塩、タルク、二酸化チタン、デンプン、木粉、カーボン・ブラック、およびこれらの混合物の中から選択される一つまたは複数のフィラーを更に含んでいることを特徴とするエラストマ組成物。
- 請求項1乃至3のいずれかに記載のエラストマ組成物であって、前記クレイは、剥離したクレイであって、剥離した天然の、又は合成したモンモリロナイト、ノントロナイト、バイデライト、ボルコンスコイト、ラポナイト、ヘクトライト、サポナイト、サウコナイト、マガダイト、ケニヤイト、スティーンサイト、バーミキュライト、ハロイサイト、アルミン酸塩酸化物、ハイドロタルサイト、およびこれらの混合物からなる群の中から選択されたものであることを特徴とするエラストマ組成物。
- 請求項1乃至4のいずれかに記載のエラストマ組成物であって、当該エラストマ組成物は、実質的にナフテン酸油を含まないことを特徴とするエラストマ組成物。
- 請求項1乃至5のいずれかに記載のエラストマ組成物であって、前記炭化水素ポリマー添加物が、少なくとも75重量%の環状成分を含有することを特徴とするエラストマ組成物。
- 請求項1乃至6のいずれかに記載のエラストマ組成物であって、前記炭化水素ポリマー添加物がジシクロペンタジエンから成ることを特徴とするエラストマ組成物。
- 請求項1乃至7のいずれかに記載のエラストマ組成物であって、前記炭化水素ポリマー添加物が115〜130 ℃の範囲の軟化点温度を有することを特徴とするエラストマ組成物。
- 請求項1乃至8のいずれかに記載のエラストマ組成物であって、前記炭化水素ポリマー添加物が、500〜700 g/moleの範囲のMwと、65〜75 ℃の範囲のTgを有することを特徴とするエラストマ組成物。
- 請求項1乃至9のいずれかに記載のエラストマ組成物であって、当該エラストマ組成物が、空気バリア材、タイヤの内側ライナー、内側チューブ、あるいはホースであることを特徴とするエラストマ組成物。
- エラストマ組成物からなる空気バリア材であって、当該エラストマ組成物は、
(a) 少なくとも一つのC4−C7モノオレフィンべースのエラストマと、少なくとも一つのフィラーと、少なくとも一つのクレイと、少なくとも一つの環状成分を備えた炭化水素ポリマー添加物とからなるコンポーネントを混合するステップと、
(b) 前記混合されたコンポーネントをキュアするステップと、
からなる方法によって製造されることを特徴とする空気バリア材。 - 請求項11に記載の空気バリア材であって、当該空気バリアがタイヤの内側ライナー、内側チューブ、あるいはホースであることを特徴とする空気バリア材。
- 請求項11または12に記載の空気バリア材であって、前記クレイは、剥離したクレイであって、剥離した天然の、又は合成したモンモリロナイト、ノントロナイト、バイデライト、ボルコンスコイト、ラポナイト、ヘクトライト、サポナイト、サウコナイト、マガダイト、ケニヤイト、スティーンサイト、バーミキュライト、ハロイサイト、アルミン酸塩酸化物、ハイドロタルサイト、およびこれらの混合物からなる群の中から選択されたものであることを特徴とする空気バリア材。
- 請求項11乃至13のいずれかに記載した空気バリア材であって、前記炭化水素ポリマー添加物が、少なくとも75重量%の環状成分を含有することを特徴とする空気バリア材。
- 請求項11乃至14のいずれかに記載した空気バリア材であって、前記炭化水素ポリマー添加物が115〜130 ℃の範囲の軟化点温度を有することを特徴とするエラストマ組成物。
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JP7105317B2 (ja) | 2018-04-03 | 2022-07-22 | エクソンモービル ケミカル パテンツ インコーポレイテッド | チオアセタート官能化イソブチレン系ポリマー及びそれを含有する硬化性組成物 |
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Also Published As
Publication number | Publication date |
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CN101643556A (zh) | 2010-02-10 |
EP2156948B1 (en) | 2011-12-28 |
JP5126987B2 (ja) | 2013-01-23 |
ATE538925T1 (de) | 2012-01-15 |
CA2671931A1 (en) | 2010-02-08 |
EP2156948A1 (en) | 2010-02-24 |
EP2156948B8 (en) | 2012-03-14 |
CA2671931C (en) | 2016-06-21 |
RU2519393C2 (ru) | 2014-06-10 |
US8476352B2 (en) | 2013-07-02 |
US20100036025A1 (en) | 2010-02-11 |
CN101643556B (zh) | 2013-02-06 |
RU2009130127A (ru) | 2011-02-20 |
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