JP2010536945A - 共役ジエンをベースとするナノ構造化ポリマー - Google Patents
共役ジエンをベースとするナノ構造化ポリマー Download PDFInfo
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- 229920000642 polymer Polymers 0.000 title claims abstract description 87
- 150000001993 dienes Chemical class 0.000 title claims abstract description 29
- 239000007822 coupling agent Substances 0.000 claims description 40
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 238000006116 polymerization reaction Methods 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 12
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- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 8
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- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000000178 monomer Substances 0.000 claims description 5
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- 229910052761 rare earth metal Inorganic materials 0.000 claims description 5
- 150000002910 rare earth metals Chemical class 0.000 claims description 5
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 claims description 4
- 125000002723 alicyclic group Chemical group 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 239000000010 aprotic solvent Substances 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 230000002902 bimodal effect Effects 0.000 claims description 3
- AHAREKHAZNPPMI-AATRIKPKSA-N (3e)-hexa-1,3-diene Chemical compound CC\C=C\C=C AHAREKHAZNPPMI-AATRIKPKSA-N 0.000 claims description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 claims description 2
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- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 claims description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 2
- IMJGQTCMUZMLRZ-UHFFFAOYSA-N buta-1,3-dien-2-ylbenzene Chemical compound C=CC(=C)C1=CC=CC=C1 IMJGQTCMUZMLRZ-UHFFFAOYSA-N 0.000 claims description 2
- 229920005669 high impact polystyrene Polymers 0.000 claims description 2
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- 230000000052 comparative effect Effects 0.000 description 11
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- 238000005859 coupling reaction Methods 0.000 description 9
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- 229910003902 SiCl 4 Inorganic materials 0.000 description 5
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 239000002086 nanomaterial Substances 0.000 description 4
- -1 vinyl aromatic compounds Chemical class 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241001441571 Hiodontidae Species 0.000 description 3
- 229910002808 Si–O–Si Inorganic materials 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
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- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
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- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 239000011954 Ziegler–Natta catalyst Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
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- 238000004821 distillation Methods 0.000 description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 150000004820 halides Chemical group 0.000 description 2
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- 239000001257 hydrogen Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003791 organic solvent mixture Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
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- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
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- 239000010703 silicon Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- PAXCWMAHLFTBMQ-UHFFFAOYSA-K 2,2-diethylhexanoate neodymium(3+) Chemical compound [Nd+3].CCCCC(CC)(CC)C([O-])=O.CCCCC(CC)(CC)C([O-])=O.CCCCC(CC)(CC)C([O-])=O PAXCWMAHLFTBMQ-UHFFFAOYSA-K 0.000 description 1
- CMAOLVNGLTWICC-UHFFFAOYSA-N 2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC=C(F)C(C#N)=C1 CMAOLVNGLTWICC-UHFFFAOYSA-N 0.000 description 1
- GAODDBNJCKQQDY-UHFFFAOYSA-N 2-methyl-4,6-bis(octylsulfanylmethyl)phenol Chemical compound CCCCCCCCSCC1=CC(C)=C(O)C(CSCCCCCCCC)=C1 GAODDBNJCKQQDY-UHFFFAOYSA-N 0.000 description 1
- UZGARMTXYXKNQR-UHFFFAOYSA-K 7,7-dimethyloctanoate;neodymium(3+) Chemical compound [Nd+3].CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O UZGARMTXYXKNQR-UHFFFAOYSA-K 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 229910052777 Praseodymium Inorganic materials 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
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- 125000003172 aldehyde group Chemical group 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
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- 238000004458 analytical method Methods 0.000 description 1
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- 230000003078 antioxidant effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 150000001785 cerium compounds Chemical class 0.000 description 1
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- 238000013329 compounding Methods 0.000 description 1
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- 230000009977 dual effect Effects 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
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- 150000002118 epoxides Chemical class 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 150000002251 gadolinium compounds Chemical class 0.000 description 1
- 150000002259 gallium compounds Chemical class 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 150000002604 lanthanum compounds Chemical class 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 150000002798 neodymium compounds Chemical class 0.000 description 1
- ARWCRSVRKCNEDI-UHFFFAOYSA-K neodymium(3+);octanoate Chemical compound [Nd+3].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O ARWCRSVRKCNEDI-UHFFFAOYSA-K 0.000 description 1
- 150000002816 nickel compounds Chemical class 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 1
- 150000003114 praseodymium compounds Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
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- 239000010959 steel Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003606 tin compounds Chemical group 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 150000003682 vanadium compounds Chemical class 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- 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
- C08C19/30—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule
- C08C19/42—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups
- C08C19/44—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups of polymers containing metal atoms exclusively at one or both ends of the skeleton
-
- 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
-
- 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
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/30—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule
- C08C19/34—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with oxygen or oxygen-containing groups
-
- 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
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/04—Carbon
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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
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
-
- 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
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/52—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides selected from boron, aluminium, gallium, indium, thallium or rare earths
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- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
Description
X3−Si−(O−SiX2)n−X
[式中、
Xは式OR(ここで、Rは、1〜30個の炭素原子を有する飽和のもしくはある程度不飽和の脂肪族炭化水素基、5〜30個の炭素原子を有する脂環式炭化水素基または6〜30個の炭素原子を有する芳香族炭化水素基である)のアルコラートであり、
nは0より大きい、好ましくは1より大きい、特に好ましくは2より大きい数である]
のオリゴマーシリケートである。
(RO)3Si−O−Si(OR)3、
(RO)3Si−O−Si(OR)2−O−Si(OR)3、
(RO)3Si−O−Si(OR)2−O−Si(OR)2−O−Si(OR)3、
(RO)3Si−O−Si(OR)2−O−Si(OR)2−O−Si(OR)2−O−Si(OR)3、
(RO)3Si−O−Si(OR)2−O−Si(OR)2−O−Si(OR)2−O−Si(OR)2−O−Si(OR)3または
(RO)3Si−O−Si(OR)2−O−Si(OR)2−O−Si(OR)2−O−Si(OR)2−O−Si(OR)2−O−Si(OR)3
(式中、Rはメチル、エチル、ビニル、プロピル、イソプロピル、ブチル、ペンチル、ヘキシル、オクチルまたはそれらの異性体である)
である。これらのオリゴマーシリケートは商業的に入手可能であり、ケイ素テトラアルコラートの縮合によって好ましくは形成され、異なる縮合度を有する化合物または化合物の混合物と定義することができる。
オリゴマーシリケートは、例としてDegussaから商標Dynasil(登録商標)40で得られる。
X3−Si−(O−SiX2)n−X
[式中、
Xは式OR(ここで、Rは、1〜30個の炭素原子を有する飽和のもしくはある程度不飽和の脂肪族炭化水素基、5〜30個の炭素原子を有する脂環式炭化水素基、または6〜30個の炭素原子を有する芳香族炭化水素基である)のアルコラートであり、
nは0より大きい、好ましくは1より大きい、特に好ましくは2より大きい数である]
のナノ−カップリング剤と反応させられ、
使用されるナノ−カップリング剤の量が、ポリマーに対して0.001〜10g:100gの範囲にあることを特徴とする、共役ジエンをベースとするナノ構造化ポリマーの製造方法を提供する。
ネオジムバーサテートに関して等モル量のヘキサン中の水素化ジイソブチルアルミニウム(DIBAH;Al(C4H9)2H)の溶液およびヘキサン中のエチルアルミニウムセスキクロライド(EASC,Al2(C2H5)3Cl3)の溶液と、ヘキサン中のネオジムバーサテート(NdV、Nd(O2C10H19)3)の溶液とを、撹拌しながら、窒素下の乾燥20Lスチール反応器中の、工業銘柄ヘキサン中13重量%の1,3−ブタジエンの溶液に加えた。混合物を次に、73℃の初期供給温度に加熱する。反応開始の60分後に反応を終了させ、ポリマー検体を採取する。100mLのヘキサンと共に変性試薬を次に、撹拌しながら、ビューレットを用いて加える。
比較例6および7は、本発明の実施例2に記載された通り実施した。ナノ−カップリング剤の代わりに、SiCl4を変性剤として使用した。このポリマーは、変性後にムーニー上昇を全く示さなかった。両比較例において、変性後に、30秒後ムーニー緩和値は、5%未満の、非結合ポリマーの範囲にあった。分子量は、SiCl4との反応後に二峰性を全く示さない。図3は、SiCl4との反応後の比較例7での分子量分布を示す。SiCl4は、ナノ−カップリング剤としての活性を全く示さなかった。
比較例8については、Lanxess Deutschland GmbH製のBunaTMCB24を使用した。本発明の実施例9および10については、実施例2および5のポリマーを使用した。配合材料の比較ムーニー粘度について、比較例8と比べると本発明の実施例9および10において耐引裂−伝搬性を著しく改善することが可能であった。
Claims (5)
- 希土類の触媒での共役ジエンの重合およびその後のナノ−カップリング剤との反応によって得られる、共役ジエンをベースとするナノ構造化ポリマーであって、高分子量画分が2,000,000g/モルより大きい平均モル質量を有する二峰性モル質量分布を得られたポリマーが有し、全体ポリマーを基準として、高分子量画分の量が1%〜20%の範囲にあり、ポリマーを基準として、全体ポリマーのゲル含有率が1%未満であり、1,2−ビニル単位の含有率が0.3〜1重量%である、ナノ構造化ポリマー。
- 共役ジエンとして、1,3−ブタジエン、2,3−ジメチル−1,3−ブタジエン、3−ブチル−1,3−オクタジエン、イソプレン、ピペリレン、1,3−ヘキサジエン、1,3−オクタジエンおよび/または2−フェニル−1,3−ブタジエンを含むことを特徴とする、請求項1に記載のナノ構造化ポリマー。
- 式:
X3−Si−(O−SiX2)n−X
[式中、
Xは式OR(ここで、Rは、1〜30個の炭素原子を有する飽和のもしくはある程度不飽和の脂肪族炭化水素基、5〜30個の炭素原子を有する脂環式炭化水素基または6〜30個の炭素原子を有する芳香族炭化水素基である)のアルコラートであり、
nは0より大きい数である]
のオリゴマーシリケートがナノ−カップリング剤として存在することを特徴とする、請求項2に記載のナノ構造化ポリマー。 - 共役ジエンを、先ず、不活性の有機非プロトン性溶媒の存在下におよび希土類の触媒の存在下に重合させ、前記モノマーをベースとする、重合反応後に得られたポリマーを、式:
X3−Si−(O−SiX2)n−X
[式中、
Xは式OR(ここで、Rは、1〜30個の炭素原子を有する飽和のもしくはある程度不飽和の脂肪族炭化水素基、5〜30個の炭素原子を有する脂環式炭化水素基、または6〜30個の炭素原子を有する芳香族炭化水素基である)のアルコラートであり、
nは0より大きい数である]
のナノ−カップリング剤と反応させ、
使用される前記ナノ−カップリング剤の量が、ポリマーに対して0.001〜10g:100gの範囲にあることを特徴とする、共役ジエンをベースとするナノ構造化ポリマーの製造方法。 - タイヤおよびタイヤ部品の、ゴルフボールおよび工業ゴム製品ならびにABSプラスチックおよびHIPSプラスチックなどの、ゴム強化プラスチックの製造のための請求項1〜4のいずれか一項に記載のナノ構造化ポリマーの使用。
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JP2015502990A (ja) * | 2011-11-03 | 2015-01-29 | ランクセス・ドイチュランド・ゲーエムベーハー | NdBRウェットマスターバッチ |
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US9758646B2 (en) | 2011-11-03 | 2017-09-12 | Arlanxeo Deutschland Gmbh | NdBR wet masterbatch |
WO2013127448A1 (en) | 2012-02-29 | 2013-09-06 | Styron Europe Gmbh | Process for producing diene polymers |
US8940838B2 (en) * | 2012-05-28 | 2015-01-27 | China Petroleum & Chemcial Corporation | Polyisoprene, preparation method thereof, polyisoprene rubber compounds and vulcanizate therefrom |
RU2561704C2 (ru) * | 2013-03-25 | 2015-09-10 | Общество с ограниченной ответственностью "Научно-производственная фирма "Белагроспецмаш" | Резиновая смесь преимущественно для пневмошин и пневмошина из нее |
SG11201602766WA (en) | 2013-10-16 | 2016-05-30 | Arlanxeo Deutschland Gmbh | Functionalized polymer composition |
JP6984610B2 (ja) * | 2016-11-15 | 2021-12-22 | 日本ゼオン株式会社 | 合成ポリイソプレンラテックス |
EP3366709A1 (en) | 2017-02-24 | 2018-08-29 | ARLANXEO Deutschland GmbH | In-chain phosphine- and phosphonium- containing diene-polymers |
WO2021154112A1 (ru) | 2020-01-29 | 2021-08-05 | Публичное Акционерное Общество "Сибур Холдинг" (Пао "Сибур Холдинг") | Способ получения модифицированных полидиенов |
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