CN1304941A - 共聚物的金属取代的方法 - Google Patents
共聚物的金属取代的方法 Download PDFInfo
- Publication number
- CN1304941A CN1304941A CN00130934A CN00130934A CN1304941A CN 1304941 A CN1304941 A CN 1304941A CN 00130934 A CN00130934 A CN 00130934A CN 00130934 A CN00130934 A CN 00130934A CN 1304941 A CN1304941 A CN 1304941A
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- Prior art keywords
- multipolymer
- metal
- alkali
- solution
- reaction
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 65
- 229910052751 metal Inorganic materials 0.000 title claims description 94
- 239000002184 metal Substances 0.000 title claims description 94
- 229920000642 polymer Polymers 0.000 title abstract description 28
- 238000006467 substitution reaction Methods 0.000 title description 26
- 229920001577 copolymer Polymers 0.000 claims abstract description 51
- -1 alkyl lithium compound Chemical class 0.000 claims abstract description 37
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 34
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 30
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 25
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 24
- 229910052792 caesium Inorganic materials 0.000 claims abstract description 16
- 150000004703 alkoxides Chemical class 0.000 claims abstract description 10
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 claims description 49
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 44
- 239000003513 alkali Substances 0.000 claims description 40
- 229910052744 lithium Inorganic materials 0.000 claims description 32
- 239000011591 potassium Substances 0.000 claims description 30
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 27
- 230000008569 process Effects 0.000 claims description 27
- 150000003440 styrenes Chemical class 0.000 claims description 21
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 claims description 18
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 14
- JBAUPCNQUQGXJT-UHFFFAOYSA-N 1-ethenyl-4-methylbenzene;2-methylprop-1-ene Chemical group CC(C)=C.CC1=CC=C(C=C)C=C1 JBAUPCNQUQGXJT-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 238000011084 recovery Methods 0.000 claims description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 1
- 125000006177 alkyl benzyl group Chemical group 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 12
- 150000002430 hydrocarbons Chemical class 0.000 abstract description 10
- 229930195733 hydrocarbon Natural products 0.000 abstract description 6
- 229910052708 sodium Inorganic materials 0.000 abstract description 5
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 3
- 229920005601 base polymer Polymers 0.000 abstract 1
- 239000012039 electrophile Substances 0.000 abstract 1
- 239000004032 superbase Substances 0.000 abstract 1
- 150000007525 superbases Chemical class 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 66
- 239000003153 chemical reaction reagent Substances 0.000 description 51
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 46
- 238000006243 chemical reaction Methods 0.000 description 42
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 28
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- 239000000047 product Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical group CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 description 9
- 229910052728 basic metal Inorganic materials 0.000 description 9
- 150000003818 basic metals Chemical class 0.000 description 9
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- 238000006884 silylation reaction Methods 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 7
- 150000001721 carbon Chemical group 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
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- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
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- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 3
- 229940041616 menthol Drugs 0.000 description 3
- 229910052752 metalloid Inorganic materials 0.000 description 3
- 150000002738 metalloids Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
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- 238000005406 washing Methods 0.000 description 3
- FEWLNYSYJNLUOO-UHFFFAOYSA-N 1-Piperidinecarboxaldehyde Chemical compound O=CN1CCCCC1 FEWLNYSYJNLUOO-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical group CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- REEBWSYYNPPSKV-UHFFFAOYSA-N 3-[(4-formylphenoxy)methyl]thiophene-2-carbonitrile Chemical compound C1=CC(C=O)=CC=C1OCC1=C(C#N)SC=C1 REEBWSYYNPPSKV-UHFFFAOYSA-N 0.000 description 2
- PQOSNJHBSNZITJ-UHFFFAOYSA-N 3-methyl-3-heptanol Chemical group CCCCC(C)(O)CC PQOSNJHBSNZITJ-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- VHOQXEIFYTTXJU-UHFFFAOYSA-N Isobutylene-isoprene copolymer Chemical group CC(C)=C.CC(=C)C=C VHOQXEIFYTTXJU-UHFFFAOYSA-N 0.000 description 2
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- 239000000654 additive Chemical group 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
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- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
- 125000001743 benzylic group Chemical group 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
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- 125000002524 organometallic group Chemical group 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000000711 polarimetry Methods 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 238000002444 silanisation Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 150000003553 thiiranes Chemical class 0.000 description 1
- 230000005919 time-dependent effect Effects 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/42—Introducing metal atoms or metal-containing groups
-
- 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
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/04—Monomers containing three or four carbon atoms
- C08F210/08—Butenes
- C08F210/10—Isobutene
-
- 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
- C08F212/00—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 aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/12—Monomers containing a branched unsaturated aliphatic radical or a ring substituted by an alkyl radical
-
- 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
- C08F8/00—Chemical modification by after-treatment
-
- 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
- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
- C08F2800/10—Copolymer characterised by the proportions of the comonomers expressed as molar percentages
-
- 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
- C08F2810/00—Chemical modification of a polymer
- C08F2810/30—Chemical modification of a polymer leading to the formation or introduction of aliphatic or alicyclic unsaturated groups
-
- 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
- C08F2810/00—Chemical modification of a polymer
- C08F2810/50—Chemical modification of a polymer wherein the polymer is a copolymer and the modification is taking place only on one or more of the monomers present in minority
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)
Abstract
Description
烷基锂(Eq)* | 醇盐(Eq)* | 溶剂T(℃)/t(min) | 硅烷基化(%)苄基位/环上 |
s-丁基锂(1) | 叔戊醇钾(1) | 环己烷RT/15 | 44/9 |
s-丁基锂(1) | 叔戊醇钾(3) | 环己烷RT/15 | 59/5 |
s-丁基锂(1) | 叔戊醇钾(10) | 环己烷RT/15 | 75/20 |
s-丁基锂(2) | 叔戊醇钾(6) | 正己烷-78/120 | 70/22 |
s-丁基锂(2) | 叔戊醇钾(6) | 正己烷-48/15 | 76/10 |
s-丁基锂(2) | 叔戊醇钾(6) | 正己烷-48/263 | 77/12 |
s-丁基锂(2) | 叔戊醇钾(6) | 环己烷RT/15 | 84/7 |
s-丁基锂(2) | 叔戊醇钾(6) | 环己烷RT/1860 | 70/1 |
s-丁基锂(2) | 叔戊醇钾(6) | 环己烷65/15 | 79/3 |
s-丁基锂(2) | 叔戊醇钾(6) | 环己烷65/43 | 87/3 |
s-丁基锂(2) | 叔戊醇钾(6) | 环己烷70/10 | 52/12 |
s-丁基锂(1.1) | 1-薄荷醇钠(1.25) | 环己烷RT/15 | 5/0 |
s-丁基锂(1.1) | 1-薄荷醇钾(1.25) | 环己烷RT/15 | 36/4 |
s-丁基锂(1.1) | 1-薄荷醇钾(1.25) | 环己烷RT/1543 | 35/3 |
s-丁基锂(1.1) | 1-薄荷醇铯(1.25) | 环己烷RT/15 | 71/1 |
s-丁基锂(1.1) | 1-薄荷醇铯(1.25) | 环己烷RT/1534 | 50/3 |
s-丁基锂(2) | 1-薄荷醇铯(2) | 环己烷RT/15 | 94/5 |
s-丁基锂(2) | 1-薄荷醇铯(4) | 环己烷RT/15 | 88/3 |
s-丁基锂(2) | 1-薄荷醇铯(6) | 环己烷RT/15 | 99/2 |
烷基锂(Eq) | 醇盐(Eq) | 添加剂(Eq) | 溶剂T(℃)/t(min) | 硅烷基化(%)苄基位/环上 |
s-丁基锂(2) | 叔戊醇钾(6) | TMEDA(8) | 环己烷RT/15 | 79/27 |
t-丁基锂(2) | 叔戊醇钾(6) | 环己烷RT/15 | 68/10 | |
t-丁基锂(2) | 叔戊醇钾(6) | TMEDA(8) | 环己烷RT/15 | 70/8 |
t-丁基锂(2) | 叔戊醇钾(6) | 质子海绵 | 环己烷RT/15 | 64/9 |
Claims (11)
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US44495095A | 1995-05-19 | 1995-05-19 | |
US08/444,950 | 1995-05-19 | ||
US44713195A | 1995-05-22 | 1995-05-22 | |
US08/447,131 | 1995-05-22 | ||
US08/476,753 US5670581A (en) | 1995-05-19 | 1995-06-07 | Metalation and functionalization of polymers and copolymers |
US08/476,753 | 1995-06-07 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN96194952A Division CN1188487A (zh) | 1995-05-19 | 1996-05-20 | 聚合物和共聚物的金属取代和官能化 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN1304941A true CN1304941A (zh) | 2001-07-25 |
Family
ID=27412231
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN00130934A Pending CN1304941A (zh) | 1995-05-19 | 2000-11-10 | 共聚物的金属取代的方法 |
Country Status (11)
Country | Link |
---|---|
US (2) | US5840810A (zh) |
EP (1) | EP0832138A2 (zh) |
JP (1) | JPH11505287A (zh) |
KR (1) | KR19990014901A (zh) |
CN (1) | CN1304941A (zh) |
BR (1) | BR9609135A (zh) |
CA (1) | CA2219464A1 (zh) |
CZ (1) | CZ363797A3 (zh) |
MX (1) | MX9708904A (zh) |
PL (1) | PL323380A1 (zh) |
WO (1) | WO1996036650A2 (zh) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6011120A (en) * | 1996-12-23 | 2000-01-04 | Exxon Chemical Patents, Inc. | Alkenyl silane functionalization of alkylstyrene homopolyers and copolymers |
AT410546B (de) * | 1996-12-23 | 2003-05-26 | Exxon Chemical Patents Inc | Verfahren zum einführen von ethylenisch ungesättigter funktionalität in ein alkylstyrol enthaltendes polymer |
JP4410868B2 (ja) * | 1998-03-04 | 2010-02-03 | 株式会社ブリヂストン | ゴム組成物及びそれを用いた空気入りタイヤ |
CA2362847A1 (en) | 1999-03-02 | 2000-09-08 | Exxonmobil Chemical Patents Inc. | Silane grafted copolymers of an alpha-olefin and a vinyl aromatic monomer |
US6451935B1 (en) | 2000-05-10 | 2002-09-17 | Bridgestone Corporation | Highly functionalized polymers and a process for making the same |
AU2003243337A1 (en) * | 2002-07-05 | 2004-01-23 | Exxonmobil Chemical Patents Inc. | Functionalized elastomer nanocomposite |
CN103013017B (zh) * | 2002-07-05 | 2017-03-01 | 埃克森美孚化学专利公司 | 官能化的弹性体纳米复合材料 |
WO2006013637A1 (ja) * | 2004-08-04 | 2006-02-09 | Hitachi, Ltd. | 電子タグ、リーダ、及びその製造方法 |
WO2006069205A1 (en) | 2004-12-21 | 2006-06-29 | Dow Global Technologies Inc. | Polypropylene-based adhesive compositions |
ZA200707873B (en) | 2005-03-17 | 2009-02-25 | Dow Global Technologies Inc | Low molecular weight ethylene/alpha-olefin interpolymer as base lubricant oils |
EP2363420B1 (en) | 2006-06-15 | 2012-12-12 | Dow Global Technologies LLC | Functionalized olefin interpolymers, compositions and articles prepared therefrom, and methods for making the same |
TWI438238B (zh) * | 2006-12-21 | 2014-05-21 | Dow Global Technologies Llc | 聚烯烴組成物與由其製備之物件,以及其之製造方法 |
WO2010008371A1 (en) * | 2008-06-30 | 2010-01-21 | Dow Global Technologies Inc. | Polyolefin compositions and articles prepared therefrom and methods of making the same |
WO2013090396A1 (en) | 2011-12-14 | 2013-06-20 | Dow Global Technologies Llc | Functionalized block composite and crystalline block composite compositions |
BR122020003369B1 (pt) | 2013-07-01 | 2021-03-02 | Rohm And Haas Company | composição de polímero compósito |
CN113195570A (zh) | 2018-12-13 | 2021-07-30 | 埃克森美孚化学专利公司 | 通过金属有机碱活化在现有聚合物链上的阴离子接枝聚合 |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1566343A (zh) * | 1968-02-05 | 1969-05-09 | ||
GB1254220A (en) * | 1968-03-14 | 1971-11-17 | Firestone Tire & Rubber Co | Method of metalating unsaturated polymers |
US3978161A (en) * | 1973-10-01 | 1976-08-31 | The General Tire & Rubber Company | Metalation of polymers |
US4145490A (en) * | 1975-09-25 | 1979-03-20 | E. I. Du Pont De Nemours And Company | Carboxylated copolymers of isobutylene and a vinylbenzene |
US4603148A (en) * | 1983-05-12 | 1986-07-29 | Hercules Incorporated | Macroreticulate polymer scavengers for the removal of impurities from inert fluids |
JPS61151203A (ja) * | 1984-12-26 | 1986-07-09 | Toa Nenryo Kogyo Kk | スチレン系重合体への前駆物質の製造法 |
US5162445A (en) * | 1988-05-27 | 1992-11-10 | Exxon Chemical Patents Inc. | Para-alkylstyrene/isoolefin copolymers and functionalized copolymers thereof |
US5077346A (en) * | 1989-10-03 | 1991-12-31 | Exxon Chemical Patents Inc. | Functionalization of polymeric organolithium compounds by carbonation |
US5461118A (en) * | 1993-04-06 | 1995-10-24 | Exxon Chemical Patents Inc. | Para-alkylstyrene/isoolefin copolymers functionalized with an amine alkylthioethers or hydroxy-alkylthioethers and their use in polymer blends |
WO1995010544A1 (en) * | 1993-10-15 | 1995-04-20 | University Of Massachusetts At Lowell | Capping of living polymers |
-
1996
- 1996-05-20 CZ CZ973637A patent/CZ363797A3/cs unknown
- 1996-05-20 EP EP96916512A patent/EP0832138A2/en not_active Withdrawn
- 1996-05-20 JP JP8535131A patent/JPH11505287A/ja not_active Ceased
- 1996-05-20 KR KR1019970708246A patent/KR19990014901A/ko not_active Application Discontinuation
- 1996-05-20 BR BR9609135A patent/BR9609135A/pt not_active Application Discontinuation
- 1996-05-20 CA CA002219464A patent/CA2219464A1/en not_active Abandoned
- 1996-05-20 PL PL96323380A patent/PL323380A1/xx unknown
- 1996-05-20 WO PCT/US1996/007278 patent/WO1996036650A2/en not_active Application Discontinuation
- 1996-06-06 US US08/659,457 patent/US5840810A/en not_active Expired - Fee Related
-
1997
- 1997-06-05 US US08/869,818 patent/US5849828A/en not_active Expired - Fee Related
- 1997-11-18 MX MX9708904A patent/MX9708904A/es not_active IP Right Cessation
-
2000
- 2000-11-10 CN CN00130934A patent/CN1304941A/zh active Pending
Also Published As
Publication number | Publication date |
---|---|
CA2219464A1 (en) | 1996-11-21 |
PL323380A1 (en) | 1998-03-30 |
US5840810A (en) | 1998-11-24 |
EP0832138A2 (en) | 1998-04-01 |
WO1996036650A3 (en) | 1996-12-19 |
WO1996036650A2 (en) | 1996-11-21 |
BR9609135A (pt) | 1999-02-17 |
JPH11505287A (ja) | 1999-05-18 |
CZ363797A3 (cs) | 1998-07-15 |
MX9708904A (es) | 1998-09-30 |
KR19990014901A (ko) | 1999-02-25 |
US5849828A (en) | 1998-12-15 |
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