JP6659699B2 - ポリオレフィン主鎖と一又は複数のポリマー側鎖とを含むグラフト共重合体の調製方法及びそれから得られる生成物 - Google Patents
ポリオレフィン主鎖と一又は複数のポリマー側鎖とを含むグラフト共重合体の調製方法及びそれから得られる生成物 Download PDFInfo
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- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 description 1
- 229960000380 propiolactone Drugs 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- RXWDMDWQNOJWJY-UHFFFAOYSA-M pyridine-3-carboxylate;tributylstannanylium Chemical compound CCCC[Sn](CCCC)(CCCC)OC(=O)C1=CC=CN=C1 RXWDMDWQNOJWJY-UHFFFAOYSA-M 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- VSZWPYCFIRKVQL-UHFFFAOYSA-N selanylidenegallium;selenium Chemical compound [Se].[Se]=[Ga].[Se]=[Ga] VSZWPYCFIRKVQL-UHFFFAOYSA-N 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000002210 silicon-based material Substances 0.000 description 1
- SCABQASLNUQUKD-UHFFFAOYSA-N silylium Chemical compound [SiH3+] SCABQASLNUQUKD-UHFFFAOYSA-N 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 229910052713 technetium Inorganic materials 0.000 description 1
- GKLVYJBZJHMRIY-UHFFFAOYSA-N technetium atom Chemical compound [Tc] GKLVYJBZJHMRIY-UHFFFAOYSA-N 0.000 description 1
- JBQYATWDVHIOAR-UHFFFAOYSA-N tellanylidenegermanium Chemical compound [Te]=[Ge] JBQYATWDVHIOAR-UHFFFAOYSA-N 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical group [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- VSEOIQRHQSIHRZ-UHFFFAOYSA-L titanium(4+);dichloride Chemical compound Cl[Ti+2]Cl VSEOIQRHQSIHRZ-UHFFFAOYSA-L 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- CMHHITPYCHHOGT-UHFFFAOYSA-N tributylborane Chemical compound CCCCB(CCCC)CCCC CMHHITPYCHHOGT-UHFFFAOYSA-N 0.000 description 1
- PWBHRVGYSMBMIO-UHFFFAOYSA-M tributylstannanylium;acetate Chemical compound CCCC[Sn](CCCC)(CCCC)OC(C)=O PWBHRVGYSMBMIO-UHFFFAOYSA-M 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- RGGPNXQUMRMPRA-UHFFFAOYSA-N triethylgallium Chemical compound CC[Ga](CC)CC RGGPNXQUMRMPRA-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical compound CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- XCZXGTMEAKBVPV-UHFFFAOYSA-N trimethylgallium Chemical compound C[Ga](C)C XCZXGTMEAKBVPV-UHFFFAOYSA-N 0.000 description 1
- DZWGKMVDRPKMPD-UHFFFAOYSA-N tripropyl(tripropylstannyloxy)stannane Chemical compound CCC[Sn](CCC)(CCC)O[Sn](CCC)(CCC)CCC DZWGKMVDRPKMPD-UHFFFAOYSA-N 0.000 description 1
- CNWZYDSEVLFSMS-UHFFFAOYSA-N tripropylalumane Chemical compound CCC[Al](CCC)CCC CNWZYDSEVLFSMS-UHFFFAOYSA-N 0.000 description 1
- GBVHWVQKJWLJKO-UHFFFAOYSA-M tripropylstannyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCC)(CCC)CCC GBVHWVQKJWLJKO-UHFFFAOYSA-M 0.000 description 1
- JQKHNBQZGUKYPX-UHFFFAOYSA-N tris(2,4,6-trimethoxyphenyl)phosphane Chemical compound COC1=CC(OC)=CC(OC)=C1P(C=1C(=CC(OC)=CC=1OC)OC)C1=C(OC)C=C(OC)C=C1OC JQKHNBQZGUKYPX-UHFFFAOYSA-N 0.000 description 1
- OBAJXDYVZBHCGT-UHFFFAOYSA-N tris(pentafluorophenyl)borane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1B(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F OBAJXDYVZBHCGT-UHFFFAOYSA-N 0.000 description 1
- SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 description 1
- RTAKQLTYPVIOBZ-UHFFFAOYSA-N tritert-butylalumane Chemical compound CC(C)(C)[Al](C(C)(C)C)C(C)(C)C RTAKQLTYPVIOBZ-UHFFFAOYSA-N 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
- 238000001622 two pulse phase modulation pulse sequence Methods 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- 229920001866 very low density polyethylene Polymers 0.000 description 1
- DWTTZBARDOXEAM-UHFFFAOYSA-N zearalenone Chemical compound O=C1OC(C)CCCC(O)CCCCCC2=CC(O)=CC(O)=C21 DWTTZBARDOXEAM-UHFFFAOYSA-N 0.000 description 1
- BYYXHWABFVUKLO-UHFFFAOYSA-N zinc;2-methylpropane Chemical compound [Zn+2].C[C-](C)C.C[C-](C)C BYYXHWABFVUKLO-UHFFFAOYSA-N 0.000 description 1
- QMBQEXOLIRBNPN-UHFFFAOYSA-L zirconocene dichloride Chemical compound [Cl-].[Cl-].[Zr+4].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 QMBQEXOLIRBNPN-UHFFFAOYSA-L 0.000 description 1
Classifications
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- 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
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
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- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
- C08G63/08—Lactones or lactides
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- C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
- C08F255/02—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 on to polymers of olefins having two or three carbon atoms
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- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/02—Ethene
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- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/04—Monomers containing three or four carbon atoms
- C08F210/06—Propene
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- C08F216/00—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 alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F216/02—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 alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an alcohol radical
- C08F216/04—Acyclic compounds
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- C08F216/00—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 alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F216/02—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 alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an alcohol radical
- C08F216/10—Carbocyclic compounds
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- 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
- C08F4/60—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 together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/639—Component covered by group C08F4/62 containing a transition metal-carbon bond
- C08F4/6392—Component covered by group C08F4/62 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring
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- 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
- C08F4/60—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 together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
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- C08F4/639—Component covered by group C08F4/62 containing a transition metal-carbon bond
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- C08F4/63922—Component covered by group C08F4/62 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring containing at least two cyclopentadienyl rings, fused or not
- C08F4/63927—Component covered by group C08F4/62 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring containing at least two cyclopentadienyl rings, fused or not two cyclopentadienyl rings being mutually bridged
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- 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
- C08F4/60—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 together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/6592—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring
- C08F4/65922—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring containing at least two cyclopentadienyl rings, fused or not
- C08F4/65927—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring containing at least two cyclopentadienyl rings, fused or not two cyclopentadienyl rings being mutually bridged
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- C08G64/18—Block or graft polymers
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- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
- C08G81/02—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers at least one of the polymers being obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C08G81/024—Block or graft polymers containing sequences of polymers of C08C or C08F and of polymers of C08G
- C08G81/027—Block or graft polymers containing sequences of polymers of C08C or C08F and of polymers of C08G containing polyester or polycarbonate sequences
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- C08F2410/00—Features related to the catalyst preparation, the catalyst use or to the deactivation of the catalyst
- C08F2410/01—Additive used together with the catalyst, excluding compounds containing Al or B
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- C08F4/60—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 together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
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- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/65912—Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an organoaluminium compound
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- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Graft Or Block Polymers (AREA)
Description
A)触媒系を使用して、少なくとも1つの第1の種類のオレフィンモノマーと、少なくとも1つの第2の種類の金属鎮静化された(pacified)官能化オレフィンモノマーとを共重合して、一又は複数の金属鎮静化された官能化短鎖分枝を有するポリオレフィン主鎖を得る工程であって、該触媒系が、
i)元素のIUPAC周期表の第3族〜第10族に由来する金属を含む、金属触媒又は金属触媒前駆体と、
ii)必要に応じて共触媒と、
を含む、工程;及び
B)前記ポリオレフィン主鎖上に一又は複数のポリマー側鎖を形成する工程であって、触媒的開始剤として、工程A)で得られたポリオレフィン主鎖上の金属鎮静化された官能化短鎖分枝が、グラフト共重合体を得るために用いられる、工程
を含む。
Cは炭素であり、
R1a、R1b、R1c、及びR1dは、各々独立して、H又は、1〜16個の炭素原子を有するヒドロカルビルからなる群より選択される。
Cは炭素であり、
R2、R3、及びR4は、各々独立して、H又は、1〜16個の炭素原子を有するヒドロカルビルからなる群より選択され、
R5X−MLnは、典型金属(main group metal)鎮静化されたヘテロ原子含有官能基である[式中、Xはヘテロ原子又はヘテロ原子含有官能基であり、Mに結合するヘテロ原子はO、S及びNからなる群より選択され、R5は、1〜16個の炭素原子を有するヒドロカルビルである]。
以下の定義は、記載される主題を明確にするために、本明細書及び特許請求の範囲において用いられる。以下に挙げられていない他の用語もまた、概ね、当技術分野で受け入れられた意味を有することが意図されている。
*第1族:リチウム(Li)、ナトリウム(Na)、及びカリウム(K)
*第2族:ベリリウム(Be)、マグネシウム(Mg)、及びカルシウム(Ca)
*第13族:ホウ素(B)、アルミニウム(Al)、ガリウム(Ga)、及びインジウム(In)
*第14族:ゲルマニウム(Ge)、及びスズ(Sn)
*第15族:アンチモン(Sb)、及びビスマス(Bi)
を意味し、
典型金属には、本発明の文脈では、亜鉛(Zn)も含まれる。
本発明に従った方法における第1の工程は、反応性の求電子性金属懸垂基を有するポリオレフィン主鎖の調製である。よって、工程A)で得られる生成物は、金属鎮静化された官能化側鎖含有ポリオレフィンである。
Cは炭素であり、
R1a、R1b、R1c、及びR1dは、各々独立して、H又は、1〜16個の炭素原子を有するヒドロカルビルからなる群より選択される。
Cは炭素であり、
R2、R3、及びR4は、各々独立して、H又は、1〜16個の炭素原子を有するヒドロカルビルからなる群より選択され、
R5−X−MLnは、金属鎮静化されたヘテロ原子含有官能基である。
・ −O−
・ −S−
・ −NR6a−
・ −CO2−
・ −C(=O)−
・ −C(=S)S−
・ −C(=O)S−
・ −C(=S)O−
・ −C(=O)N(R6a)−
・ −C(=NR6a)O−
・ −C(=NR6a)N(R6b)−
・ −C(=NR6b)N(R6a)−
・ −C(=S)N(R6a)−
・ −C(=NR6a)S−
・ −CH2C(R6a)=C(OR6b)O−
・ −CH2C(R6a)=C(NR6bR6c)O−
・ −CH2C(R6a)=P(OR6bOR6c)O−
・ −C(R6a)=N−
・ −C(R6a)R6bC(R6c)R6dO−
・ −C(R6a)R6bC(R6c)R6dNR6e−
・ −C(=O)−R6a−C(=O)O−
・ −C(R6bR6c)N(R6a)−
・ −S(=O)2O−
・ −C(R6a)(R6b)O−
工程A)で使用するための触媒系は、以下の成分を含む:
i)元素のIUPAC周期表の第3族〜第10族に由来する金属を含む、金属触媒又は金属触媒前駆体、
ii)必要に応じて共触媒、及び
iii)必要に応じて捕捉剤。
以下のセクションにおいて、本発明に従った金属触媒又は、該金属触媒の調製に使用されうる金属触媒前駆体の幾つかの例が特定される。本発明の工程A)での使用に適した金属触媒は、工程A)での使用前に金属触媒前駆体を共触媒と反応させることによって、又は、共触媒とのインサイチュ反応によって、得られうる。
共触媒は、金属触媒前駆体が適用される場合に用いられうる。この共触媒の機能は、金属触媒前駆体を活性化することである。共触媒は、例として、例えばトリイソブチルアルミニウムなどのアルミニウムアルキルと組み合わせる可能性がある、例えばアルミニウムアルキル及びアルミニウムアルキルハライド、例えば、トリエチルアルミニウム(TEA)又はジエチルアルミニウムクロリド(DEAC)、MAO、DMAO、MMAO、SMAOなどからなる群より選択されてよく、及び/又は、例えばトリイソブチルアルミニウムなどのアルミニウムアルキルと、フッ化アリールボラン又はフッ化アリールボラート(すなわち、B(R’)y、ここで、それぞれ、R’はフッ化アリールであり、yは3又は4である)との組合せなどであってもよい。フッ化ボランの例はB(C6F5)3であり、フッ化ボラートの例は、[X]+[B(C6F5)4]−(例えばX=Ph3C、C6H5N(H)Me2)である。
捕捉剤は、重合リアクタ内、及び/又は、供給される溶媒及び/又はモノマー内に存在する不純物と反応させるために、必要に応じて触媒系に加えられうる。この捕捉剤は、オレフィン重合プロセスの間の触媒の被毒を防止する。捕捉剤は、共触媒と同一であって差し支えないが、アルミニウムヒドロカルビル(例えばトリイソブチルアルミニウム、トリオクチルアルミニウム、トリメチルアルミニウム、MAO、MMAO、SMAO)、亜鉛ヒドロカルビル(例えばジエチル亜鉛)又はマグネシウムヒドロカルビル(例えばジブチルマグネシウム)からなる群より独立して選択されてもよい。
工程A)は、少なくとも2種類のオレフィンを重合して、共重合体化されたポリオレフィン主鎖を提供する工程であり、この工程は、好ましくは、不活性雰囲気下で行われる。
上述のように、グラフト共重合体は、工程B)の間に形成される。工程B)は、したがって、一又は複数の金属鎮静化された官能化短鎖分枝上にポリマー側鎖を形成して、グラフト共重合体を得る工程である。言い換えれば、工程B)は、ポリマー側鎖、すなわちポリマー分枝、すなわちグラフト共重合体の形成に関する。これは、例えばROPによって行われうる。これは、カルボニル基含有官能基(例えばカルボン酸又は炭酸エステル官能基)を含む事前合成されたポリマーを用いる求核置換反応によっても行うことができる。ポリマー分枝は、したがって、ランダム又はブロック共重合体でありうる。
本発明の方法の工程B)の間に、環状モノマーのROPによってポリマー側鎖が形成されうる。
工程B)の間に、ポリオレフィン主鎖にポリマー側鎖を付加するために、求核置換反応が行われうる。
本方法の工程B)の間に、ポリマー側鎖は、例えばラクトンなどの環状モノマーのROPと、例えばエステル交換反応などの求核置換との組合せによって形成されうる。
本発明は、グラフト共重合体の調製のための2段階プロセスに関する。
本発明の利点は、共重合体の合成に向けて必要とされるプロセス工程の数の低減である。本発明に従った方法は、先行技術に従った方法と比べて、より短時間及び省エネルギーにし、かつ、より材料消費を少なくする。
ポリエチレン−グラフト−ポリカプロラクトン共重合体の調製のため、単一バッチリアクタ内で行われる連続的な供給プロセスを適用した。第1の工程A)は、エチレン/C11OH共重合からなり、その後にCLのROPが続く(工程B)。重合反応を、ステンレス鋼Buchiリアクタ内で行った。重合の前に、リアクタを、真空下、40℃で乾燥させ、窒素を流した。トルエン溶媒(70mL)を導入し、続いて、不活性雰囲気下でTIBA及び官能性モノマーを導入した。結果的に得られた溶液を15〜20分間攪拌し、続いて、窒素雰囲気下で計算量の共触媒を添加した。金属触媒前駆体をリアクタに加えることによって、重合反応を開始した。次に、リアクタを、エチレンで所望の圧力まで加圧し、その圧力を所定の時間、維持した。エチレンの供給を停止し、残留圧力を解放した。液体注入管を通じて、計算量のCLモノマーを不活性雰囲気下で加え、懸濁液を、強攪拌(600rpm)下で所定の時間、60℃に維持した。酸性メタノール(10%濃塩酸)中での沈降によって反応を終わらせ、PE−グラフト−PCL共重合体とPCL材料を単離した。
1H NMR解析を、TCE−d2を溶媒として使用して80〜110℃で行い、400MHzの周波数で動作する、Varian Mercury分光計の5mmチューブに記録した。化学シフトは、テトラメチルシランに対してppm単位で報告され、残留溶媒を参照して決定された。
工程A)は、第1の種類のオレフィンモノマーとしてエチレン、第2の種類のオレフィンモノマーとしてインサイチュ保護化C11OH、金属触媒前駆体として1を使用して行われた。さらには、TIBA及びMAOが用いられる。工程B)の間に、環状モノマーとしてCLを用いてROPプロセスが行われた。
工程A)は、第1の種類のオレフィンモノマーとしてエチレン、第2の種類のオレフィンモノマーとしてインサイチュ保護化C11OH、金属触媒前駆体として2を使用して行われた。さらには、TIBA及びMAOが用いられる。工程B)の間に、環状モノマーとしてCLを用いてROPプロセスが行われた。
工程A)は、第1の種類のオレフィンモノマーとしてエチレン、金属触媒前駆体として3を使用して行われた。さらには、TIBA及びMAOが用いられる。工程B)の間に、環状モノマーとしてCLを用いてROPプロセスが行われた。
工程A)は、第1の種類のオレフィンモノマーとしてエチレン、第2の種類のオレフィンモノマーとしてインサイチュ保護化C11OH、金属触媒前駆体として1を使用して行われた。さらには、TIBA、MAO及びBHTが用いられる。工程B)の間に、環状モノマーとしてCLを用いてROPプロセスが行われた。
b)mmol(M)単位のMAO共触媒;
c)TIBA:C11OH:触媒のモル比;ここで、TIBAは連鎖移動剤として用いられ;C11OHは、コモノマーとして用いられたインサイチュ保護化10−ウンデセン−1−オールである;
d)C2:バール単位のエチレン圧であり、括弧内は分単位の反応時間である;
e)記載される値は、mmol単位の量である。括弧内の値は、分単位の時間である;
f)収量クルードは、グラム単位の酸性メタノール中での沈降後の収量である。これは、所望のグラフト共重合体と1つ以上のホモポリマーとの混合物を含みうる;
g)THF中の収量は、THFに可溶性のPCLホモポリマーを除去するためにTHF中に沈降させた後の収量である;
h)Mnは、g/mol単位の数平均分子量であり、括弧内の値は多分散指数である。
工程A)は、第1の種類のオレフィンモノマーとしてプロピレン、第2の種類のオレフィンモノマーとしてインサイチュ保護化C11OH、金属触媒前駆体として1を使用して行われた。さらには、TIBA及びMAOが用いられる。工程B)の間に、環状モノマーとしてCLを用いてROPプロセスが行われた。
工程A)は、第1の種類のオレフィンモノマーとしてプロピレン、第2の種類のオレフィンモノマーとしてインサイチュ保護化C11OH、金属触媒前駆体として1を使用して行われた。さらには、TIBA及びトリチルテトラキス(ペンタフルオロフェニル)ボラートが用いられる。工程B)の間に、環状モノマーとしてCLを用いてROPプロセスが行われた。
工程A)は、第1の種類のオレフィンモノマーとしてプロピレン、第2の種類のオレフィンモノマーとしてインサイチュ保護化C11OH、金属触媒前駆体として2を使用して行われた。さらには、TIBA及びMAOが用いられる。工程B)の間に、環状エステルモノマーとしてCLを用いてROPプロセスが行われた。
工程A)は、第1の種類のオレフィンモノマーとしてプロピレン、第2の種類のオレフィンモノマーとしてインサイチュ保護化C11OH、金属触媒前駆体として2を使用して行われた。さらには、TIBA及びトリチルテトラキス(ペンタフルオロフェニル)ボラートが用いられる。工程B)の間に、環状エステルモノマーとしてCLを用いてROPプロセスが行われた。
b)mmol(M)単位のMAO共触媒;
c)TIBA:C11OH:触媒のモル比;ここで、TIBAは連鎖移動剤として用いられ;C11OHは、コモノマーとして用いられたインサイチュ保護化10−ウンデセン−1−オールである;
d)C3:バール単位のプロピレン圧力であり、括弧内は分単位の反応時間である;
e)記載される値は、mmol単位の量である。括弧内の値は、分単位の時間である;
f)収量クルードは、グラム単位の酸性メタノール中での沈降後の収量である。これは、所望のグラフト共重合体と1つ以上のホモポリマーとの混合物を含みうる;
g)THF中の収量は、THFに可溶性のPCLホモポリマーを除去するためにTHF中に沈降させた後の収量である;
h)Mnは、g/mol単位の数平均分子量であり、括弧内の値は多分散指数である。
他の実施形態
1.ポリオレフィン主鎖と一又は複数のポリマー側鎖とを含むグラフト共重合体の調製方法において、
A)触媒系を使用して、少なくとも1つの第1の種類のオレフィンモノマーと、少なくとも1つの第2の種類の金属鎮静化された官能化オレフィンモノマーとを共重合し、一又は複数の金属鎮静化された官能化短鎖分枝を有するポリオレフィン主鎖を得る工程であって、該触媒系が、
i)元素のIUPAC周期表の第3族〜第10族に由来する金属を含む、金属触媒又は金属触媒前駆体と、
ii)必要に応じて共触媒と、
を含む、工程と、
B)前記ポリオレフィン主鎖上に一又は複数のポリマー側鎖を形成する工程であって、触媒的開始剤として、工程A)で得られた前記ポリオレフィン主鎖上の前記金属鎮静化された官能化短鎖分枝を用いて、前記グラフト共重合体を得る、工程と
を含む、方法。
2.前記方法が、好ましくは金属置換をしない、一連のリアクタを使用する単一プロセスであることを特徴とする、実施形態1に記載の方法。
3.グラフト共重合体を得る工程B)が、少なくとも1種類の環状モノマーを使用するROPによって行われることを特徴とする、実施形態1又は2に記載の方法。
4.グラフト共重合体を得る工程B)が、前記側鎖についての少なくとも1種類のポリマーのカルボニル基含有官能基における求核置換反応によって行われることを特徴とする、実施形態1又は2に記載の方法。
5.グラフト共重合体を得る工程B)が、少なくとも1種類の環状モノマーを使用するROPと、少なくとも1種類の第2のポリマーのカルボニル基含有官能基における少なくとも1つの求核置換反応との組合せによって行われることを特徴とする、実施形態1又は2に記載の方法。
6.前記少なくとも1つの第1の種類のオレフィンモノマーが、式I−Aに従った化合物であり、
Cは炭素であり、
R 1a 、R 1b 、R 1c 、及びR 1d は、各々独立して、H又は、1〜16個の炭素原子を有するヒドロカルビルからなる群より選択される
ことを特徴とする、実施形態1から5のいずれかに記載の方法。
7.前記少なくとも1つの第2の種類の金属鎮静化された官能化オレフィンモノマーが、式I−Bに従った化合物であり、
Cは炭素であり、
R 2 、R 3 、及びR 4 は、各々独立して、H又は、1〜16個の炭素原子を有するヒドロカルビルからなる群より選択され、
R 5 −X−ML n は、典型金属鎮静化されたヘテロ原子含有官能基であり、ここで、Xは、ヘテロ原子又はヘテロ原子含有基であり、Mに結合するヘテロ原子は、O、S及びNからなる群より選択され、R 5 は、1〜16個の炭素原子を有するヒドロカルビルである、
ことを特徴とする、実施形態1から6のいずれかに記載の方法。
8.工程B)の間に、ROP、エステル交換反応又は求核置換反応のための追加的な触媒が添加されないことを特徴とする、実施形態1〜7のいずれかに記載の方法。
9.工程A)で用いられる前記金属触媒又は金属触媒前駆体が、元素のIUPAC周期表の第3族〜第8族、好ましくは第3族〜第6族、さらに好ましくは第3族〜第4族に由来する金属を含む、及び/又は、工程A)で用いられる前記金属触媒又は金属触媒前駆体が、Ti、Zr、Hf、V、Cr、Fe、Co、Ni、Pdからなる群より選択される金属、好ましくはTi、Zr又はHfを含むことを特徴とする、実施形態1〜8のいずれかに記載の方法。
10.前記共触媒が、MAO、DMAO、MMAO、SMAO、フッ化アリールボラン、又はフッ化アリールボラートからなる群より選択されることを特徴とする、実施形態1から9のいずれかに記載の方法。
11.式I−Aに従った前記オレフィンモノマーが、エチレン、プロピレン、1−ブテン、4−メチル−1−ペンテン、1−ペンテン、1−ヘキセン、1−ヘプテン、1−オクテン、1−ノネン、1−デセン、1−ウンデセン、1−ドデセン、1−トリデセン、1−テトラデセン、1−ペンタデセン、1−ヘキサデセン、1−ヘプタデセン、1−オクタデセン、1−シクロペンテン、シクロヘキセン、ノルボルネン、エチリデン−ノルボルネン、及びビニリデン−ノルボルネン、並びにそれらの1つ以上の組合せからなる群より選択されることを特徴とする、実施形態1から10のいずれかに記載の方法。
12.工程B)のROPの間に用いられる前記環状モノマーが、ラクトン、ラクチド、例えば、ジ−エステル、トリ−エステル、テトラ−エステル、ペンタ−エステル又はより高次のオリゴエステルなどの環状オリゴエステル、エポキシド、アジリジン、エポキシド及び/又はアジリジンとCO 2 との組合せ、環状無水物、エポキシド及び/又はアジリジンと環状無水物との組合せ、エポキシド及び/又はアジリジンとCO 2 と環状無水物との組合せ、環状N−カルボキシ無水物、環状カーボネート、ラクタム、及びそれらの1つ以上の組合せからなる群より選択される極性モノマーであり、好ましくはラクトンであり、あるいは、工程B)のROPの間に用いられる前記環状モノマーが、少なくとも12原子の環サイズを有する無極性の環状モノマーであり、好ましくは、マクロラクトンなどの環状エステル、環状カーボネート、環状アミド、環状ウレタン、及び環状尿素、又はそれらの1つ以上の組合せからなる群より選択され、さらに好ましくはマクロラクトンであることを特徴とする、実施形態3、5及び6から11のいずれかに記載の方法。
13.少なくとも1つのカルボン酸エステル又は炭酸エステル官能基又はカルボニル基含有官能基を含む前記側鎖を形成するために工程B)の間に付加される前記ポリマーが、ポリエステル、ポリカーボネート、ポリアミド、ポリウレタン、ポリ尿素、ランダム又はブロックポリ(カーボネート−エステル)、ポリ(カーボネート−エーテル)、ポリ(エステル−エーテル)、ポリ(カーボネート−エーテル−エステル)、ポリ(エステル−アミド)、ポリ(エステル−エーテル−アミド)、ポリ(カーボネート−アミド)、ポリ(カーボネート−エーテル−アミド)、ポリ(エステル−ウレタン)、ポリ(エステル−エーテル−ウレタン)、ポリ(カーボネート−ウレタン)、ポリ(カーボネート−エーテル−ウレタン)、ポリ(エステル−尿素)、ポリ(エステル−エーテル−尿素)、ポリ(カーボネート−尿素)、ポリ(カーボネート−エーテル−尿素)、ポリ(エーテル−アミド)、ポリ(アミド−ウレタン)、ポリ(アミド−尿素)、ポリ(ウレタン−尿素)又はそれらの1つ以上の組合せからなる群より選択されることを特徴とする、実施形態4、5及び6から12のいずれかに記載の方法。
14.前記金属鎮静化された官能化オレフィンモノマーを得るために用いられる、鎮静化用金属が、アルミニウム、チタン、亜鉛、ガリウム、マグネシウム、カルシウム及びそれらの1つ以上の組合せからなる群より選択されることを特徴とする、実施形態1から13のいずれかに記載の方法。
15.実施形態1から14のいずれかに記載の方法によって得られた又は得ることができるグラフト共重合体。
Claims (12)
- ポリオレフィン主鎖と一又は複数のポリマー側鎖とを含むグラフト共重合体の調製方法において、
A)触媒系を使用して、少なくとも1つの第1の種類のオレフィンモノマーと、少なくとも1つの第2の種類の金属鎮静化された官能化オレフィンモノマーとを共重合し、一又は複数の金属鎮静化された官能化短鎖分枝を有するポリオレフィン主鎖を得る工程であって、前記触媒系が、
i)元素のIUPAC周期表の第3族〜第10族に由来する金属を含む金属触媒又は金属触媒前駆体と、
ii)任意選択で共触媒と、
を含む、工程、及び
B)前記ポリオレフィン主鎖上に一又は複数のポリマー側鎖を形成して、グラフト共重合体を得る工程であって、触媒的開始剤として、工程A)で得られた前記ポリオレフィン主鎖上の前記金属鎮静化された官能化短鎖分枝が用いられる、工程
を含み、
グラフト共重合体を得る工程B)が、少なくとも1種類の側鎖用のポリマーのカルボニル基含有官能基における求核置換反応によって行われるか、又は
グラフト共重合体を得る工程B)が、少なくとも1種類の環状モノマーを使用する開環重合(ROP)と、少なくとも1種類の側鎖用のポリマーのカルボニル基含有官能基における求核置換反応との組合せによって行われる、方法。 - 一連のリアクタを使用する単一プロセスである、請求項1に記載の方法。
- 前記少なくとも1つの第2の種類の金属鎮静化された官能化オレフィンモノマーが、式I−Bに従う化合物であり、
Cは炭素であり、
R2、R3、及びR4は、各々独立して、H、又は1〜16個の炭素原子を有するヒドロカルビルからなる群より選択され、
R5−X−MLnは、典型金属鎮静化されたヘテロ原子含有官能基であり、ここで、Xはヘテロ原子又はヘテロ原子含有基であり、Mに結合するヘテロ原子は、O、S及びNからなる群より選択され、Mは典型金属であり、Lは配位子であり、nは、L n の全体の電荷がMの酸化状態−1となるように0、1、2又は3であり、R5は1〜16個の炭素原子を有するヒドロカルビルである、請求項1から3のいずれか一項に記載の方法。 - 前記配位子Lが、ヒドリド、ヒドロカルビル、ハライド、アルコキシド、アリールオキシド、アミド、チオラート、メルカプテート、カルボキシレート、カルバメート、サレン、サラン、サラレン、グアニジナート、ポルフィリン、β−ケチミナート、フェノキシ−イミン、フェノキシ−アミン、ビスフェノラート、トリスフェノラート、アルコキシアミン、アルコキシエーテル、アルコキシチオエーテル、サブカーボネート及びサブサリチレート又はそれらの組合せからなる群より独立して選択される、請求項4に記載の方法。
- 工程B)の間に、ROP、エステル交換反応又は求核置換反応のための追加的な触媒が添加されない、請求項1から5のいずれか一項に記載の方法。
- 工程A)で用いられる前記金属触媒又は金属触媒前駆体が、元素のIUPAC周期表の第3族〜第8族に由来する金属を含む、又は、工程A)で用いられる前記金属触媒又は金属触媒前駆体が、Ti、Zr、Hf、V、Cr、Fe、Co、Ni、Pdからなる群より選択される金属を含む、請求項1から6のいずれか一項に記載の方法。
- 前記共触媒が、MAO、DMAO、MMAO、SMAO、フッ化アリールボラン、又はフッ化アリールボラートからなる群より選択される、請求項1から7のいずれか一項に記載の方法。
- 前記少なくとも1つの第1の種類のオレフィンモノマーが、エチレン、プロピレン、1−ブテン、4−メチル−1−ペンテン、1−ペンテン、1−ヘキセン、1−ヘプテン、1−オクテン、1−ノネン、1−デセン、1−ウンデセン、1−ドデセン、1−トリデセン、1−テトラデセン、1−ペンタデセン、1−ヘキサデセン、1−ヘプタデセン、1−オクタデセン、1−シクロペンテン、シクロヘキセン、ノルボルネン、エチリデン−ノルボルネン、及びビニリデン−ノルボルネン、並びにそれらの1つ以上の組合せからなる群より選択される、請求項1から8のいずれか一項に記載の方法。
- 工程B)のROPの間に用いられる環状モノマーが、ラクトン、ラクチド、環状オリゴエステル、エポキシド、アジリジン、エポキシド及び/又はアジリジンとCO2との組合せ、環状無水物、エポキシド及び/又はアジリジンと環状無水物との組合せ、エポキシド及び/又はアジリジンとCO2と環状無水物との組合せ、環状N−カルボキシ無水物、環状カーボネート、ラクタム、及びそれらの1つ以上の組合せからなる群より選択される極性モノマーであり、あるいは、工程B)のROPの間に用いられる環状モノマーが、少なくとも12原子の環サイズを有する無極性の環状モノマーである、請求項1から9のいずれか一項に記載の方法。
- 工程B)の間に付加されるカルボニル基含有官能基を含む前記少なくとも1種類の側鎖用のポリマーが、ポリエステル、ポリカーボネート、ポリアミド、ポリウレタン、ポリ尿素、ランダム又はブロックポリ(カーボネート−エステル)、ポリ(カーボネート−エーテル)、ポリ(エステル−エーテル)、ポリ(カーボネート−エーテル−エステル)、ポリ(エステル−アミド)、ポリ(エステル−エーテル−アミド)、ポリ(カーボネート−アミド)、ポリ(カーボネート−エーテル−アミド)、ポリ(エステル−ウレタン)、ポリ(エステル−エーテル−ウレタン)、ポリ(カーボネート−ウレタン)、ポリ(カーボネート−エーテル−ウレタン)、ポリ(エステル−尿素)、ポリ(エステル−エーテル−尿素)、ポリ(カーボネート−尿素)、ポリ(カーボネート−エーテル−尿素)、ポリ(エーテル−アミド)、ポリ(アミド−ウレタン)、ポリ(アミド−尿素)、ポリ(ウレタン−尿素)又はそれらの1つ以上の組合せからなる群より選択される、請求項1から10のいずれか一項に記載の方法。
- 前記金属鎮静化された官能化オレフィンモノマーを得るために用いられる鎮静化用金属が、アルミニウム、チタン、亜鉛、ガリウム、マグネシウム、カルシウム及びそれらの1つ以上の組合せからなる群より選択される、請求項1から3のいずれか一項に記載の方法。
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PCT/EP2015/080340 WO2016097207A1 (en) | 2014-12-17 | 2015-12-17 | A process for the preparation of a graft copolymer comprising a polyolefin main chain and one or a multiple polymer side chains and the products obtained therefrom |
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US10519267B2 (en) | 2019-12-31 |
EP3034544A1 (en) | 2016-06-22 |
SA517381731B1 (ar) | 2020-12-15 |
KR102483732B1 (ko) | 2022-12-30 |
JP2017538828A (ja) | 2017-12-28 |
CN107207712B (zh) | 2020-08-07 |
WO2016097207A1 (en) | 2016-06-23 |
US20170320989A1 (en) | 2017-11-09 |
EP3233975B1 (en) | 2019-08-14 |
EP3233975A1 (en) | 2017-10-25 |
KR20170107991A (ko) | 2017-09-26 |
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