JP2016500398A - 高不透過性を有するブチルゴム - Google Patents
高不透過性を有するブチルゴム Download PDFInfo
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- JP2016500398A JP2016500398A JP2015548122A JP2015548122A JP2016500398A JP 2016500398 A JP2016500398 A JP 2016500398A JP 2015548122 A JP2015548122 A JP 2015548122A JP 2015548122 A JP2015548122 A JP 2015548122A JP 2016500398 A JP2016500398 A JP 2016500398A
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- Prior art keywords
- composition
- butyl rubber
- iir
- monomer
- fots
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 229920005549 butyl rubber Polymers 0.000 title claims abstract description 157
- 239000013545 self-assembled monolayer Substances 0.000 claims abstract description 33
- 239000002094 self assembled monolayer Substances 0.000 claims abstract description 32
- PYJJCSYBSYXGQQ-UHFFFAOYSA-N trichloro(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](Cl)(Cl)Cl PYJJCSYBSYXGQQ-UHFFFAOYSA-N 0.000 claims abstract description 17
- 150000001282 organosilanes Chemical class 0.000 claims abstract description 13
- PISDRBMXQBSCIP-UHFFFAOYSA-N trichloro(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CC[Si](Cl)(Cl)Cl PISDRBMXQBSCIP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 45
- 229920000642 polymer Polymers 0.000 claims description 44
- 150000002978 peroxides Chemical class 0.000 claims description 32
- 239000000178 monomer Substances 0.000 claims description 29
- -1 aliphatic diene Chemical class 0.000 claims description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- 229920005555 halobutyl Polymers 0.000 claims description 26
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 25
- 229910052760 oxygen Inorganic materials 0.000 claims description 25
- 239000001301 oxygen Substances 0.000 claims description 25
- 229920000554 ionomer Polymers 0.000 claims description 24
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical group CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 21
- 229910052710 silicon Inorganic materials 0.000 claims description 21
- 239000010703 silicon Substances 0.000 claims description 21
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 20
- 239000012038 nucleophile Substances 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 229910052698 phosphorus Inorganic materials 0.000 claims description 14
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 239000011574 phosphorus Substances 0.000 claims description 13
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- 229920002554 vinyl polymer Polymers 0.000 claims description 11
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 10
- 230000015572 biosynthetic process Effects 0.000 claims description 10
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 10
- FRPLKHQCXVNBNO-UHFFFAOYSA-N (4-ethenylphenyl)-diphenylphosphane Chemical group C1=CC(C=C)=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 FRPLKHQCXVNBNO-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 7
- 230000026030 halogenation Effects 0.000 claims description 6
- 238000005658 halogenation reaction Methods 0.000 claims description 6
- 230000001590 oxidative effect Effects 0.000 claims description 6
- 238000005240 physical vapour deposition Methods 0.000 claims description 6
- 229910003902 SiCl 4 Inorganic materials 0.000 claims description 5
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 claims description 2
- QDZXSLUJYIHQDN-UHFFFAOYSA-N 2-ethenyl-9-ethylcarbazole Chemical compound C1=C(C=C)C=C2N(CC)C3=CC=CC=C3C2=C1 QDZXSLUJYIHQDN-UHFFFAOYSA-N 0.000 claims description 2
- NNBKMEUAQBLPSI-UHFFFAOYSA-N CCC(=O)NC=C.C1(=CC=CC=C1)C(=CP)C1=CC=CC=C1 Chemical compound CCC(=O)NC=C.C1(=CC=CC=C1)C(=CP)C1=CC=CC=C1 NNBKMEUAQBLPSI-UHFFFAOYSA-N 0.000 claims description 2
- GDFCSMCGLZFNFY-UHFFFAOYSA-N Dimethylaminopropyl Methacrylamide Chemical compound CN(C)CCCNC(=O)C(C)=C GDFCSMCGLZFNFY-UHFFFAOYSA-N 0.000 claims description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- PDDYFPPQDKRJTK-UHFFFAOYSA-N diphenyl(prop-2-enyl)phosphane Chemical compound C=1C=CC=CC=1P(CC=C)C1=CC=CC=C1 PDDYFPPQDKRJTK-UHFFFAOYSA-N 0.000 claims description 2
- AJVBXLXLODZUME-UHFFFAOYSA-N ethenyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=C)C1=CC=CC=C1 AJVBXLXLODZUME-UHFFFAOYSA-N 0.000 claims description 2
- FLEBNGWAHUAGKT-UHFFFAOYSA-N n,n-bis(prop-2-enyl)butan-1-amine Chemical compound CCCCN(CC=C)CC=C FLEBNGWAHUAGKT-UHFFFAOYSA-N 0.000 claims description 2
- 230000000269 nucleophilic effect Effects 0.000 claims description 2
- NDIFDGDMWAZLDH-UHFFFAOYSA-N phenyl-bis(prop-2-enyl)phosphane Chemical compound C=CCP(CC=C)C1=CC=CC=C1 NDIFDGDMWAZLDH-UHFFFAOYSA-N 0.000 claims description 2
- IGDLZDCWMRPMGL-UHFFFAOYSA-N 2-ethenylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(C=C)C(=O)C2=C1 IGDLZDCWMRPMGL-UHFFFAOYSA-N 0.000 claims 1
- 230000002140 halogenating effect Effects 0.000 claims 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 claims 1
- 150000003376 silicon Chemical class 0.000 claims 1
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- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical group Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 abstract 1
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- 235000012431 wafers Nutrition 0.000 description 13
- 125000004968 halobutyl group Chemical group 0.000 description 12
- 238000004483 ATR-FTIR spectroscopy Methods 0.000 description 11
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- 239000004809 Teflon Substances 0.000 description 6
- 229920006362 Teflon® Polymers 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 description 4
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- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 4
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- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 3
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- IPJGAEWUPXWFPL-UHFFFAOYSA-N 1-[3-(2,5-dioxopyrrol-1-yl)phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC(N2C(C=CC2=O)=O)=C1 IPJGAEWUPXWFPL-UHFFFAOYSA-N 0.000 description 2
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- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 2
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 2
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- 125000002950 monocyclic group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000010058 rubber compounding Methods 0.000 description 1
- 238000000682 scanning probe acoustic microscopy Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- SBIBMFFZSBJNJF-UHFFFAOYSA-N selenium;zinc Chemical compound [Se]=[Zn] SBIBMFFZSBJNJF-UHFFFAOYSA-N 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- AVXLXFZNRNUCRP-UHFFFAOYSA-N trichloro(1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctyl)silane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)[Si](Cl)(Cl)Cl AVXLXFZNRNUCRP-UHFFFAOYSA-N 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/25—Incorporating silicon atoms into the molecule
-
- 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
- C08L23/22—Copolymers of isobutene; Butyl rubber ; Homo- or copolymers of other iso-olefins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/24—Incorporating phosphorus atoms into the molecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L15/00—Compositions of rubber derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
本発明は不透過性(impermeability)を高める(increase)処理表面を有するブチルゴムに関する。更に詳しくは、本発明はビニル側基を持ったモノマーを含むブチルゴムに関する。なお更に詳しくは、光透明性を示す、任意に充填していないブチルゴムに関する。表面処理したブチルゴムの作製方法も開示される。
ポリ(イソブチレン−コ(co)−イソプレン)又はIIRは、1940年代からイソブチレンと、少量の(1〜2モル%)イソプレンとのランダムカチオン共重合により製造されている、通常ブチルゴムとして知られた合成エラストマーである。その分子構造の結果として、優れた空気不透過性、高い損失モデュラス、酸化安定性及び長期の耐疲労性を有している。
ここでは、IIRの酸素に対する不透過性を高める(図1)パーフルオロ化オルガノシラン自己組織単分子層(self-assembled monolayer)(SAM)の形成を可能にする、IIR表面をオルガノシランに対し高度に反応性にするプラズマ処理と化学的処理との組合わせに基づく簡単で効果的な表面改質方法を説明する。ブチルゴムの空気不透過性を改良するこの方法は、IIR配合物に充填剤を添加する通常、使用されている方法に比べて、2つの重要な利点がある。第一に、空気不透過性を改良する材料改質がIIR基体の表面に限定され、引張強度、硬度等の所望の内部特性をそのまま保持する。第二に、この方法は透明なIIR配合物の光透明性を顕著に損なうことはない。これに対し、充填剤は改質材料を不透明化する場合が多い。
ブチルゴムアイオノマー(ionomer)はハロゲン化ブチルゴム重合体から作製される。ブチルゴム重合体類は一般に、少なくとも1種のイソオレフィンモノマー、少なくとも1種のマルチオレフィンモノマー及び任意に更に共重合性モノマーから誘導される。
式中Aは窒素又は燐であり、R1、R2及びR3は、独立に直鎖又は分枝鎖のC1〜C18アルキル置換基、単環式か又はC4〜C8縮合環で構成されるいずれかのアリール置換基、又はそれらの組合わせから選択、構成される。R1、R2,又はR3の少なくとも1種はビニル側基を有する。
MDR
非充填ブチルゴム(U−IIR)基体の製造
充填IIR基体の製造
IIR基体の酸化
四塩化珪素処理
IIR基体上でのSAMの作製
接触角測定
フーリエ変換赤外分光法
透過性測定
結果
非充填U−IIR表面の酸化
シリケート層の形成
自己組織単分子層(SAM)の形成
透過性試験
光透明性
結論
Claims (26)
- 少なくとも1種のイソオレフィンモノマーから誘導された繰返し単位及び少なくとも1種のマルチオレフィンモノマーから誘導された繰返し単位を有すると共に、オルガノシラン自己組織単分子層(self-assembled monolayer)を持った表面を有するブチルゴム組成物。
- イソオレフィンモノマーがC4〜C8イソモノオレフィンモノマーを含む請求項1に記載の組成物。
- イソオレフィンモノマーがイソブチレンである請求項2に記載の組成物。
- マルチオレフィンモノマーがC5〜C11共役脂肪族ジエンモノマーを含む請求項1に記載の組成物。
- マルチオレフィンモノマーがイソプレンである請求項4に記載の組成物。
- 少なくとも1種のマルチオレフィンモノマーから誘導された繰返し単位が、少なくとも1種のマルチオレフィンモノマーと少なくとも1種の窒素系(based on)又は燐系求核剤とのハロゲン化後の反応生成物を含有する請求項1に記載の組成物。
- マルチオレフィンモノマーがハロゲン化の前に0.5〜2.5モル%の合計量で存在する請求項1に記載の組成物。
- 窒素系又は燐系求核剤がビニル側基を有する請求項6に記載の組成物。
- 求核剤が、ジフェニルホスフィノスチレン(DPPS)、アリルジフェニルホスフィン、ジアリルフェニルホスフィン、ジフェニルビニルホスフィン、トリアリルフェニルホスフィン、N−ビニルカプロラクタム、N−ビニルフタルイミド、9−ビニルカルバゾール、N−[3−(ジメチルアミノ)プロピル]メタクリルアミド、ジフェニルビニルホスフィン−メチル−N−ビニルアセトアミド、N−アリル−N−ブチル−2−プロペン−1−アミン、1−ビニル−2−ピロリドン、2−イソプロペニル−2−オキサゾリン、2−ビニルピリド−4−ビニルピリジン、N−エチル−2−ビニルカルバゾール及びそれらの混合物よりなる群から選ばれる請求項8に記載の組成物。
- 組成物は、0.51mm以下の厚さで提供された場合、630nmの波長に対し75%以上の光透明性を示す請求項6に記載の組成物。
- 組成物が過酸化物硬化される請求項1に記載の組成物。
- 組成物が充填されない請求項1に記載の組成物。
- オルガノシラン自己組織単分子層が、オルガノトリクロロシラン蒸気との表面反応によって形成される請求項1に記載の組成物。
- 組成物の酸素に対する不透過性が、オルガノシラン自己組織単分子層形成後、15〜25%だけ高まる請求項1に記載の組成物。
- a)少なくとも1種のイソオレフィンモノマーから誘導された繰返し単位及び1種以上のマルチオレフィンモノマーから誘導された繰返し単位を有するブチルゴム重合体を用意する(provide)工程、
b)該ブチルゴム重合体の表面を酸化する工程、
c)該表面をアルコールで処理する工程、
d)該処理された表面をハロゲン化珪素に露出する工程、及び
e)該ハロゲン化珪素露出表面を、自己組織単分子層の形成に好適な条件下でオルガノトリクロロシランと反応させる工程、
を含む、ブチルゴム組成物の不透過度を高める方法。 - 前記方法が、b)工程の前に、
前記ブチル重合体をハロゲン化してアリル性(allylic)ハロゲン部分を形成する工程、
窒素系又は燐系求核剤を該ハロゲン化ブチルゴム重合体と反応させる工程、及び
前記アリル性ハロゲン部分を該求核剤と反応させて過酸化物硬化ブチルゴムアイオノマー(ionomer)を形成する工程、
を更に含む請求項15に記載の方法。 - 前記窒素系又は燐系求核剤がビニル側基を有する請求項16に記載の方法。
- 前記方法が、
過酸化物硬化剤を前記窒素系又は燐系求核剤及びハロゲン化ブチルゴム重合体と混合する工程、及び過酸化物硬化剤に好適な条件下で硬化する工程、
を更に含む請求項16に記載の方法。 - 前記組成物は、0.51mm以下の厚さで提供された場合、630nmの波長に対し75%以上の光透明性を示す請求項17に記載の方法。
- 前記ハロゲン化珪素がテトラハロゲン化珪素である請求項15に記載の方法。
- テトラハロゲン化珪素がSiCl4を含む請求項20に記載の方法。
- 前記表面が酸素含有RFプラズマにより酸化される請求項15に記載の方法。
- 前記表面が6〜15秒間の前記RFプラズマにより酸化される請求項22に記載の方法。
- オルガノトリクロロシランが、トリクロロ(1H,1H,2H,2H−パーフルオロオクチル)シラン(FOTS)、n−オクタデシルトリクロロシラン(OTS)又はそれらの組合わせを含む請求項15に記載の方法。
- オルガノトリクロロシランが、物理的蒸着(PVD)により付着される請求項15に記載の方法。
- ゴム組成物の酸素に対する不透過性が15〜25%だけ高まる請求項15に記載の方法。
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US201261738681P | 2012-12-18 | 2012-12-18 | |
US61/738,681 | 2012-12-18 | ||
PCT/CA2013/001047 WO2014094123A1 (en) | 2012-12-18 | 2013-12-16 | Butyl rubber with increased impermeability |
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JP2016500398A true JP2016500398A (ja) | 2016-01-12 |
JP2016500398A5 JP2016500398A5 (ja) | 2017-03-09 |
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EP (1) | EP2935451B1 (ja) |
JP (1) | JP6441228B2 (ja) |
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EP2935451A1 (en) | 2015-10-28 |
KR20150129656A (ko) | 2015-11-20 |
EP2935451B1 (en) | 2019-01-16 |
SG11201504717YA (en) | 2015-07-30 |
EP2935451A4 (en) | 2016-08-03 |
US20150329649A1 (en) | 2015-11-19 |
CN105358619A (zh) | 2016-02-24 |
CN105358619B (zh) | 2017-06-20 |
US9745388B2 (en) | 2017-08-29 |
RU2656050C2 (ru) | 2018-05-30 |
TW201434914A (zh) | 2014-09-16 |
CA2894638A1 (en) | 2014-06-26 |
WO2014094123A1 (en) | 2014-06-26 |
JP6441228B2 (ja) | 2018-12-19 |
SA515360604B1 (ar) | 2016-09-05 |
RU2015129313A (ru) | 2017-01-26 |
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