CN1049666C - 用共轭二烯和甲基丙烯酸甲酯制备高耐热性热塑性弹性体嵌段共聚物的方法及所得的产品 - Google Patents
用共轭二烯和甲基丙烯酸甲酯制备高耐热性热塑性弹性体嵌段共聚物的方法及所得的产品 Download PDFInfo
- Publication number
- CN1049666C CN1049666C CN93120665A CN93120665A CN1049666C CN 1049666 C CN1049666 C CN 1049666C CN 93120665 A CN93120665 A CN 93120665A CN 93120665 A CN93120665 A CN 93120665A CN 1049666 C CN1049666 C CN 1049666C
- Authority
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- China
- Prior art keywords
- methyl
- lithium
- polymerization
- temperature
- initiator
- 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.)
- Expired - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 25
- 150000001993 dienes Chemical class 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title claims description 6
- 229920001169 thermoplastic Polymers 0.000 title abstract description 4
- 239000004416 thermosoftening plastic Substances 0.000 title abstract description 4
- 229920001400 block copolymer Polymers 0.000 title description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical group COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000003999 initiator Substances 0.000 claims abstract description 20
- 239000000178 monomer Substances 0.000 claims abstract description 17
- 229920001577 copolymer Polymers 0.000 claims abstract description 11
- 239000003446 ligand Substances 0.000 claims abstract description 9
- 239000002904 solvent Substances 0.000 claims abstract description 9
- 125000000129 anionic group Chemical group 0.000 claims abstract description 4
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims abstract description 3
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 27
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 21
- 239000004926 polymethyl methacrylate Substances 0.000 claims description 21
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 20
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 9
- 229910052744 lithium Inorganic materials 0.000 claims description 9
- 239000004793 Polystyrene Substances 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 230000009477 glass transition Effects 0.000 claims description 8
- 229920002223 polystyrene Polymers 0.000 claims description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 7
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 6
- GYNXHYIIRNOTNR-UHFFFAOYSA-N CC[O-].COCCO.[Li+] Chemical compound CC[O-].COCCO.[Li+] GYNXHYIIRNOTNR-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 claims description 5
- 239000012429 reaction media Substances 0.000 claims description 5
- 229920002725 thermoplastic elastomer Polymers 0.000 claims description 5
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 4
- 230000001588 bifunctional effect Effects 0.000 claims description 4
- 239000012454 non-polar solvent Substances 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 229910052728 basic metal Inorganic materials 0.000 claims description 3
- 150000003818 basic metals Chemical class 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- -1 phenylbenzene alkadiene Chemical class 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 2
- QHHUCCOZVUZUSR-UHFFFAOYSA-N C=1C=CC=CC=1C([Na])C1=CC=CC=C1 Chemical compound C=1C=CC=CC=1C([Na])C1=CC=CC=C1 QHHUCCOZVUZUSR-UHFFFAOYSA-N 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000001118 alkylidene group Chemical group 0.000 claims description 2
- 238000010539 anionic addition polymerization reaction Methods 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000001273 butane Substances 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 238000001746 injection moulding Methods 0.000 claims description 2
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 claims description 2
- CETVQRFGPOGIQJ-UHFFFAOYSA-N lithium;hexane Chemical compound [Li+].CCCCC[CH2-] CETVQRFGPOGIQJ-UHFFFAOYSA-N 0.000 claims description 2
- XWRJSDBMRJIGSK-UHFFFAOYSA-N lithium;phenylmethylbenzene Chemical compound [Li+].C=1C=CC=CC=1[CH-]C1=CC=CC=C1 XWRJSDBMRJIGSK-UHFFFAOYSA-N 0.000 claims description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000004417 polycarbonate Substances 0.000 claims description 2
- 229920000515 polycarbonate Polymers 0.000 claims description 2
- 239000004800 polyvinyl chloride Substances 0.000 claims description 2
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 2
- IRAPFUAOCHNONS-UHFFFAOYSA-N potassium;phenylmethylbenzene Chemical compound [K+].C=1C=CC=CC=1[CH-]C1=CC=CC=C1 IRAPFUAOCHNONS-UHFFFAOYSA-N 0.000 claims description 2
- 230000035939 shock Effects 0.000 claims description 2
- STILSQWPHFFEBU-UHFFFAOYSA-N CC(CC[Li])CC.C1(=CC=CC=C1)C1=CC=CC=C1 Chemical compound CC(CC[Li])CC.C1(=CC=CC=C1)C1=CC=CC=C1 STILSQWPHFFEBU-UHFFFAOYSA-N 0.000 claims 1
- 230000009977 dual effect Effects 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229920001971 elastomer Polymers 0.000 abstract 1
- 239000000806 elastomer Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000005062 Polybutadiene Substances 0.000 description 6
- 229920002857 polybutadiene Polymers 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 230000002779 inactivation Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 229920000428 triblock copolymer Polymers 0.000 description 2
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- ROGIWVXWXZRRMZ-UHFFFAOYSA-N 2-methylbuta-1,3-diene;styrene Chemical compound CC(=C)C=C.C=CC1=CC=CC=C1 ROGIWVXWXZRRMZ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-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
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229920000359 diblock copolymer Polymers 0.000 description 1
- CJSBUWDGPXGFGA-UHFFFAOYSA-N dimethyl-butadiene Natural products CC(C)=CC=C CJSBUWDGPXGFGA-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005516 engineering process Methods 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
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000003808 methanol extraction Methods 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229910052700 potassium Chemical group 0.000 description 1
- 239000011591 potassium Chemical group 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229920001935 styrene-ethylene-butadiene-styrene Polymers 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 238000003856 thermoforming Methods 0.000 description 1
- 239000012745 toughening agent Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
-
- 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
- C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
- C08F297/02—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type
- C08F297/026—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type polymerising acrylic acid, methacrylic acid or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J153/00—Adhesives based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
- Graft Or Block Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9214318 | 1992-11-27 | ||
| FR9214318A FR2698630B1 (fr) | 1992-11-27 | 1992-11-27 | Procédé de préparation de copolymères séquences élastomères thermoplastiques dérivés de diènes conjugués et de méthacrylate de méthyle, à tenue à la chaleur améliorée et produits obtenus. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1089957A CN1089957A (zh) | 1994-07-27 |
| CN1049666C true CN1049666C (zh) | 2000-02-23 |
Family
ID=9435994
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN93120665A Expired - Fee Related CN1049666C (zh) | 1992-11-27 | 1993-11-27 | 用共轭二烯和甲基丙烯酸甲酯制备高耐热性热塑性弹性体嵌段共聚物的方法及所得的产品 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US5476904A (enExample) |
| EP (1) | EP0599671B1 (enExample) |
| JP (1) | JP2520863B2 (enExample) |
| KR (1) | KR0133492B1 (enExample) |
| CN (1) | CN1049666C (enExample) |
| AT (1) | ATE131501T1 (enExample) |
| AU (1) | AU5193893A (enExample) |
| CA (1) | CA2110080C (enExample) |
| DE (1) | DE69301022T2 (enExample) |
| ES (1) | ES2080598T3 (enExample) |
| FR (1) | FR2698630B1 (enExample) |
| MX (1) | MX9307450A (enExample) |
| TW (1) | TW269695B (enExample) |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101547989B (zh) * | 2006-12-07 | 2011-07-06 | 3M创新有限公司 | 嵌段共聚物和丙烯酸类粘合剂的共混物 |
| US8911971B2 (en) | 2011-02-17 | 2014-12-16 | Purecircle Usa Inc. | Glucosyl stevia composition |
| US8981081B2 (en) | 2010-03-12 | 2015-03-17 | Purecircle Usa Inc. | High-purity steviol glycosides |
| US8993269B2 (en) | 2011-02-17 | 2015-03-31 | Purecircle Usa Inc. | Glucosyl stevia composition |
| US9029426B2 (en) | 2010-12-13 | 2015-05-12 | Purecircle Sdn Bhd | Highly soluble Rebaudioside D |
| US9107436B2 (en) | 2011-02-17 | 2015-08-18 | Purecircle Sdn Bhd | Glucosylated steviol glycoside as a flavor modifier |
| US9243273B2 (en) | 2012-05-22 | 2016-01-26 | Purecircle Sdn Bhd | Method for making rebaudioside X |
| US9386797B2 (en) | 2011-02-17 | 2016-07-12 | Purecircle Sdn Bhd | Glucosyl stevia composition |
| US9392799B2 (en) | 2011-02-17 | 2016-07-19 | Purecircle Sdn Bhd | Glucosyl stevia composition |
| US9427006B2 (en) | 2011-02-10 | 2016-08-30 | Purecircle Sdn Bhd | Highly soluble Stevia sweetener |
| US9474296B2 (en) | 2011-02-17 | 2016-10-25 | Purecircle Sdn Bhd | Glucosyl stevia composition |
| US9510611B2 (en) | 2010-12-13 | 2016-12-06 | Purecircle Sdn Bhd | Stevia composition to improve sweetness and flavor profile |
| US12037356B2 (en) | 2010-03-12 | 2024-07-16 | Purecircle Usa Inc. | Methods of preparing steviol glycosides and uses of the same |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2729669A1 (fr) * | 1995-01-20 | 1996-07-26 | Atochem Elf Sa | Procede de preparation de polymeres de (meth) acrylates d'alkyle par polymerisation anionique |
| FR2762604B1 (fr) * | 1997-04-10 | 2001-01-05 | Atochem Elf Sa | Procede et systeme d'amorcage pour la (co)polymerisation anionique de monomeres (meth)acryliques, vinylaromatiques et/ou dieniques |
| US6734256B1 (en) * | 1998-12-29 | 2004-05-11 | 3M Innovative Properties Company | Block copolymer hot-melt processable adhesives, methods of their preparation, and articles therefrom |
| EP1591507A3 (en) * | 1998-12-29 | 2006-01-25 | Minnesota Mining And Manufacturing Company | Block copolymer hot-melt processable adhesives |
| FR2809741B1 (fr) * | 2000-05-31 | 2002-08-16 | Atofina | Materiaux thermodurs a tenue au choc amelioree |
| JP4554836B2 (ja) * | 2001-02-27 | 2010-09-29 | 株式会社クラレ | ゴム組成物 |
| FR2824834B1 (fr) * | 2001-05-18 | 2005-05-13 | Rhodia Elect & Catalysis | Procede de preparation de copolymeres blocs, copolymeres blocs ainsi obtenus et utilisation comme agents compatibilisants |
| JP2003082167A (ja) * | 2001-09-17 | 2003-03-19 | Kuraray Co Ltd | ゴム組成物 |
| JP4659303B2 (ja) * | 2001-09-18 | 2011-03-30 | 株式会社クラレ | ジエン系ゴム組成物 |
| KR20050057666A (ko) * | 2002-10-21 | 2005-06-16 | 아르끄마 | 무정형 매트릭스 및 블록 공중합체를 함유하는 연성의 투명열가소성 조성물 |
| US7951887B2 (en) | 2003-05-30 | 2011-05-31 | Nippon Soda Co., Ltd. | Process for producing a polymer |
| CN1312197C (zh) * | 2004-07-15 | 2007-04-25 | 复旦大学 | 改性软硬多嵌段共轭聚合物及其制备方法 |
| CN1315888C (zh) * | 2004-09-24 | 2007-05-16 | 奇美实业股份有限公司 | 以甲基丙烯酸甲酯为主成分的聚合物 |
| EP2065442B1 (en) * | 2006-09-15 | 2013-03-27 | Kuraray Co., Ltd. | Methacrylic resin composition, resin modifier, and molded body |
| US8417312B2 (en) | 2007-10-25 | 2013-04-09 | Dexcom, Inc. | Systems and methods for processing sensor data |
| JP5186415B2 (ja) * | 2008-02-28 | 2013-04-17 | 株式会社クラレ | メタクリル系樹脂フィルム |
| JP5186416B2 (ja) * | 2008-02-28 | 2013-04-17 | 株式会社クラレ | 表示窓保護板 |
| JP5227847B2 (ja) * | 2008-02-29 | 2013-07-03 | 株式会社クラレ | メタクリル系樹脂組成物 |
| JP5317768B2 (ja) * | 2008-03-03 | 2013-10-16 | 株式会社クラレ | メタクリル系重合体組成物 |
| JP5237858B2 (ja) * | 2008-03-04 | 2013-07-17 | 株式会社クラレ | メタクリル系樹脂用改質剤 |
| IT1402007B1 (it) * | 2010-10-06 | 2013-08-28 | Polimeri Europa Spa | Procedimento per la preparazione di polimeri dienici o copolimeri statistici vinilarene-diene |
| TWI609912B (zh) * | 2012-06-29 | 2018-01-01 | Kuraray Co., Ltd. | （甲基）丙烯酸樹脂組成物之製造方法、光學構件之製造方法及偏光板之製造方法 |
| FR3029921B1 (fr) * | 2014-12-16 | 2018-06-29 | Arkema France | Procede de controle de la synthese d'un copolymere a blocs contenant au moins un bloc apolaire et au moins un bloc polaire et utilisation d'un tel copolymere a blocs dans des applications de nano-lithographie par auto-assemblage direct. |
| CN110799553B (zh) | 2017-07-14 | 2022-08-16 | 株式会社Lg化学 | 用于生产聚合物的方法 |
| CN110540610B (zh) * | 2018-05-28 | 2021-08-20 | 浙江省化工研究院有限公司 | 一种（甲基）丙烯酸酯类聚合物及其制备方法 |
| CN112480292A (zh) * | 2020-11-30 | 2021-03-12 | 沈阳化工研究院有限公司 | 一种丙烯酸烷基酯类极性单体阴离子聚合制备高分子聚合物的方法 |
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| GB138069A (en) * | 1919-01-11 | 1920-09-02 | Erwin Walter | Improvements in or relating to plaiting machines |
| GB138073A (en) * | 1920-01-17 | 1921-07-18 | George Macnair | Improvements in multiple pulley hoisting gears |
| DE1227235B (de) * | 1962-10-08 | 1966-10-20 | Ceskoslovenska Akademie Ved | Verfahren zur Herstellung von Polymeren oder Copolymeren durch anionische Polymerisation |
| US3285894A (en) * | 1963-10-11 | 1966-11-15 | Ceskoslovenska Akademie Ved | Polymerization initiators comprising alkali metal alcoholates |
| US3439064A (en) * | 1965-01-11 | 1969-04-15 | Exxon Research Engineering Co | Laminating varnish consisting of low viscosity,curable block copolymer |
| FR2387255A1 (fr) * | 1977-04-15 | 1978-11-10 | Anvar | Procede de preparation de copolymeres trisequences ou en etoile |
| ATE121104T1 (de) * | 1989-06-05 | 1995-04-15 | Atochem Elf Sa | Verfahren und anionische polymerisationskatalysatoren für acrylatmonomere. |
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- 1993-10-01 DE DE69301022T patent/DE69301022T2/de not_active Expired - Fee Related
- 1993-10-01 ES ES93402418T patent/ES2080598T3/es not_active Expired - Lifetime
- 1993-10-01 EP EP93402418A patent/EP0599671B1/fr not_active Expired - Lifetime
- 1993-10-01 AT AT93402418T patent/ATE131501T1/de not_active IP Right Cessation
- 1993-11-26 AU AU51938/93A patent/AU5193893A/en not_active Abandoned
- 1993-11-26 KR KR1019930025372A patent/KR0133492B1/ko not_active Expired - Fee Related
- 1993-11-26 CA CA002110080A patent/CA2110080C/fr not_active Expired - Fee Related
- 1993-11-26 JP JP5321278A patent/JP2520863B2/ja not_active Expired - Fee Related
- 1993-11-26 MX MX9307450A patent/MX9307450A/es unknown
- 1993-11-27 CN CN93120665A patent/CN1049666C/zh not_active Expired - Fee Related
- 1993-11-29 US US08/158,395 patent/US5476904A/en not_active Expired - Fee Related
-
1994
- 1994-02-03 TW TW083100901A patent/TW269695B/zh active
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US4461874A (en) * | 1981-10-02 | 1984-07-24 | Cosden Technology, Inc. | Block copolymers of conjugated dienes or vinyl substituted aromatic hydrocarbons and acrylic esters and process for their manufacture |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101547989B (zh) * | 2006-12-07 | 2011-07-06 | 3M创新有限公司 | 嵌段共聚物和丙烯酸类粘合剂的共混物 |
| US12037356B2 (en) | 2010-03-12 | 2024-07-16 | Purecircle Usa Inc. | Methods of preparing steviol glycosides and uses of the same |
| US8981081B2 (en) | 2010-03-12 | 2015-03-17 | Purecircle Usa Inc. | High-purity steviol glycosides |
| US9510611B2 (en) | 2010-12-13 | 2016-12-06 | Purecircle Sdn Bhd | Stevia composition to improve sweetness and flavor profile |
| US9029426B2 (en) | 2010-12-13 | 2015-05-12 | Purecircle Sdn Bhd | Highly soluble Rebaudioside D |
| US9427006B2 (en) | 2011-02-10 | 2016-08-30 | Purecircle Sdn Bhd | Highly soluble Stevia sweetener |
| US9107436B2 (en) | 2011-02-17 | 2015-08-18 | Purecircle Sdn Bhd | Glucosylated steviol glycoside as a flavor modifier |
| US9386797B2 (en) | 2011-02-17 | 2016-07-12 | Purecircle Sdn Bhd | Glucosyl stevia composition |
| US9392799B2 (en) | 2011-02-17 | 2016-07-19 | Purecircle Sdn Bhd | Glucosyl stevia composition |
| US9055761B2 (en) | 2011-02-17 | 2015-06-16 | Purecircle Usa Inc. | Glucosyl Stevia composition |
| US9474296B2 (en) | 2011-02-17 | 2016-10-25 | Purecircle Sdn Bhd | Glucosyl stevia composition |
| US8993269B2 (en) | 2011-02-17 | 2015-03-31 | Purecircle Usa Inc. | Glucosyl stevia composition |
| US11844365B2 (en) | 2011-02-17 | 2023-12-19 | Purecircle Sdn Bhd | Glucosyl Stevia composition |
| US8911971B2 (en) | 2011-02-17 | 2014-12-16 | Purecircle Usa Inc. | Glucosyl stevia composition |
| US9243273B2 (en) | 2012-05-22 | 2016-01-26 | Purecircle Sdn Bhd | Method for making rebaudioside X |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2698630A1 (fr) | 1994-06-03 |
| TW269695B (enExample) | 1996-02-01 |
| MX9307450A (es) | 1994-08-31 |
| KR0133492B1 (ko) | 1998-04-21 |
| CA2110080A1 (fr) | 1994-05-28 |
| EP0599671B1 (fr) | 1995-12-13 |
| JPH06206952A (ja) | 1994-07-26 |
| KR940011511A (ko) | 1994-06-21 |
| AU5193893A (en) | 1994-06-09 |
| CN1089957A (zh) | 1994-07-27 |
| DE69301022D1 (de) | 1996-01-25 |
| US5476904A (en) | 1995-12-19 |
| DE69301022T2 (de) | 1996-09-05 |
| CA2110080C (fr) | 2000-02-15 |
| FR2698630B1 (fr) | 1995-01-06 |
| ATE131501T1 (de) | 1995-12-15 |
| ES2080598T3 (es) | 1996-02-01 |
| EP0599671A1 (fr) | 1994-06-01 |
| JP2520863B2 (ja) | 1996-07-31 |
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