CA1128236A - PROCESS FOR PREPARING GRAFT POLYMERS OF .alpha.,.alpha.-DISUBSTITUTED-.beta.-PROPIOLACTONES ON ISOBUTYLENE-TRIENE COPOLYMERS - Google Patents
PROCESS FOR PREPARING GRAFT POLYMERS OF .alpha.,.alpha.-DISUBSTITUTED-.beta.-PROPIOLACTONES ON ISOBUTYLENE-TRIENE COPOLYMERSInfo
- Publication number
- CA1128236A CA1128236A CA351,014A CA351014A CA1128236A CA 1128236 A CA1128236 A CA 1128236A CA 351014 A CA351014 A CA 351014A CA 1128236 A CA1128236 A CA 1128236A
- Authority
- CA
- Canada
- Prior art keywords
- alpha
- beta
- copolymer
- solvent
- dialkylsubstituted
- 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
Links
- 229920001577 copolymer Polymers 0.000 title claims abstract description 27
- 229920000578 graft copolymer Polymers 0.000 title claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 5
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 9
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 9
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000004185 ester group Chemical group 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 8
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 7
- 150000004291 polyenes Chemical class 0.000 claims abstract description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 6
- 238000005698 Diels-Alder reaction Methods 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims abstract description 6
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical class O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 claims abstract 3
- 241000352333 Amegilla alpha Species 0.000 claims abstract 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 14
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical group [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 8
- ULKFLOVGORAZDI-UHFFFAOYSA-N 3,3-dimethyloxetan-2-one Chemical group CC1(C)COC1=O ULKFLOVGORAZDI-UHFFFAOYSA-N 0.000 claims description 7
- 125000005207 tetraalkylammonium group Chemical group 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical group O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 4
- AFVDZBIIBXWASR-AATRIKPKSA-N (E)-1,3,5-hexatriene Chemical compound C=C\C=C\C=C AFVDZBIIBXWASR-AATRIKPKSA-N 0.000 claims description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 229920005556 chlorobutyl Polymers 0.000 claims description 3
- CGMDPTNRMYIZTM-NKYSMPERSA-N (2e,4e,6e)-octa-2,4,6-triene Chemical compound C\C=C\C=C\C=C\C CGMDPTNRMYIZTM-NKYSMPERSA-N 0.000 claims description 2
- GQVMHMFBVWSSPF-SOYUKNQTSA-N (4E,6E)-2,6-dimethylocta-2,4,6-triene Chemical compound C\C=C(/C)\C=C\C=C(C)C GQVMHMFBVWSSPF-SOYUKNQTSA-N 0.000 claims description 2
- UBFBTMRIJJRZOA-AATRIKPKSA-N (4e)-2,7-dimethylocta-2,4,6-triene Chemical compound CC(C)=C\C=C\C=C(C)C UBFBTMRIJJRZOA-AATRIKPKSA-N 0.000 claims description 2
- USKZHEQYENVSMH-YDFGWWAZSA-N 1,3,5-Heptatriene Chemical compound C\C=C\C=C\C=C USKZHEQYENVSMH-YDFGWWAZSA-N 0.000 claims description 2
- BOBLSBAZCVBABY-WPWUJOAOSA-N 1,6-diphenylhexatriene Chemical compound C=1C=CC=CC=1\C=C\C=C\C=C\C1=CC=CC=C1 BOBLSBAZCVBABY-WPWUJOAOSA-N 0.000 claims description 2
- CGMDPTNRMYIZTM-UHFFFAOYSA-N Sarohornene Natural products CC=CC=CC=CC CGMDPTNRMYIZTM-UHFFFAOYSA-N 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- GQVMHMFBVWSSPF-UHFFFAOYSA-N cis-alloocimene Natural products CC=C(C)C=CC=C(C)C GQVMHMFBVWSSPF-UHFFFAOYSA-N 0.000 claims description 2
- 238000006704 dehydrohalogenation reaction Methods 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims 1
- 125000005396 acrylic acid ester group Chemical group 0.000 claims 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims 1
- 239000002798 polar solvent Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 101100388071 Thermococcus sp. (strain GE8) pol gene Proteins 0.000 description 3
- 150000002596 lactones Chemical class 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 229920005601 base polymer Polymers 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- -1 polyene hydrocarbon Chemical class 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 229960000380 propiolactone Drugs 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- 239000004416 thermosoftening plastic Substances 0.000 description 2
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 description 1
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000861718 Chloris <Aves> Species 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- 230000009102 absorption Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- GPUADMRJQVPIAS-QCVDVZFFSA-M cerivastatin sodium Chemical compound [Na+].COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 GPUADMRJQVPIAS-QCVDVZFFSA-M 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 125000005609 naphthenate group Chemical group 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- GNWXVOQHLPBSSR-UHFFFAOYSA-N oxolane;toluene Chemical compound C1CCOC1.CC1=CC=CC=C1 GNWXVOQHLPBSSR-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 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
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
-
- 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
- C08F8/46—Reaction with unsaturated dicarboxylic acids or anhydrides thereof, e.g. maleinisation
-
- 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
- C08F2800/20—Copolymer characterised by the proportions of the comonomers expressed as weight or mass percentages
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT22641/79A IT1165058B (it) | 1979-05-14 | 1979-05-14 | Processo per la preparazione di polimeri graffati di alfa,alfa' disostituiti beta-propiolattoni su copolieri a base di isobutilene e trieni |
| IT22641A/79 | 1979-05-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1128236A true CA1128236A (en) | 1982-07-20 |
Family
ID=11198742
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA351,014A Expired CA1128236A (en) | 1979-05-14 | 1980-04-30 | PROCESS FOR PREPARING GRAFT POLYMERS OF .alpha.,.alpha.-DISUBSTITUTED-.beta.-PROPIOLACTONES ON ISOBUTYLENE-TRIENE COPOLYMERS |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4282337A (enExample) |
| JP (1) | JPS55157624A (enExample) |
| BE (1) | BE883309A (enExample) |
| CA (1) | CA1128236A (enExample) |
| DE (1) | DE3018473C2 (enExample) |
| FR (1) | FR2456751A1 (enExample) |
| GB (1) | GB2048899B (enExample) |
| IT (1) | IT1165058B (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4753998A (en) * | 1986-06-30 | 1988-06-28 | Union Camp Corporation | Diels-alder adducts of poly(aloocimene) |
| US4690983A (en) * | 1986-11-05 | 1987-09-01 | Union Camp Corporation | Hydrogenated poly(alloocimene) |
| US4690979A (en) * | 1986-11-05 | 1987-09-01 | Union Camp Corporation | Terminally functionalized poly(alloocimene) |
| US4690982A (en) * | 1986-11-05 | 1987-09-01 | Union Camp Corporation | Epoxidized poly(alloocimene) |
| US4694047A (en) * | 1986-11-06 | 1987-09-15 | Union Camp Corporation | Halogenated poly(alloocimene) |
| US4690984A (en) * | 1986-11-25 | 1987-09-01 | Union Camp Corporation | Metal complexes of poly(alloocimene) |
| BRPI1107079A2 (pt) * | 2010-08-31 | 2013-01-22 | Goodyear Tire & Rubber | copolÍmeros de monâmeros de trieno conjugados para interaÇço melhorada com enchimento |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3639519A (en) * | 1968-05-02 | 1972-02-01 | Phillips Petroleum Co | Process for preparing block copolymers by reacting lactone with a polymer |
| US3627837A (en) * | 1968-11-25 | 1971-12-14 | Firestone Tire & Rubber Co | Grafting of preformed polymer side chains on metalated backbone polymer |
| BE786747A (fr) * | 1971-07-26 | 1973-01-26 | Du Pont | Copolymeres greffes statistiques de pivalolactones |
| US3846387A (en) * | 1972-03-29 | 1974-11-05 | Du Pont | Chain saturated copolymers of ethylene, alpha monoolefins, and trienes containing side-chains with non-terminal conjugated unsaturation |
| US4029718A (en) * | 1972-06-30 | 1977-06-14 | E. I. Du Pont De Nemours And Company | Pivalolactone random graft copolymers |
| US3884882A (en) * | 1973-01-10 | 1975-05-20 | Du Pont | Certain EPDM copolymer/maleic anhydride adducts and thermoplastic elastomers therefrom |
| US4031168A (en) * | 1974-09-24 | 1977-06-21 | E. I. Du Pont De Nemours And Company | Copolymers of isobutylene and a vinylbenzene and graft polymers thereof with pivalolactone |
-
1979
- 1979-05-14 IT IT22641/79A patent/IT1165058B/it active
-
1980
- 1980-04-25 US US06/144,170 patent/US4282337A/en not_active Expired - Lifetime
- 1980-04-30 GB GB8014323A patent/GB2048899B/en not_active Expired
- 1980-04-30 CA CA351,014A patent/CA1128236A/en not_active Expired
- 1980-05-12 FR FR8010637A patent/FR2456751A1/fr active Granted
- 1980-05-13 JP JP6234280A patent/JPS55157624A/ja active Pending
- 1980-05-14 BE BE0/200625A patent/BE883309A/fr not_active IP Right Cessation
- 1980-05-14 DE DE3018473A patent/DE3018473C2/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB2048899B (en) | 1983-10-12 |
| FR2456751A1 (fr) | 1980-12-12 |
| BE883309A (fr) | 1980-11-14 |
| FR2456751B1 (enExample) | 1983-01-21 |
| IT7922641A0 (it) | 1979-05-14 |
| US4282337A (en) | 1981-08-04 |
| DE3018473A1 (de) | 1980-11-27 |
| GB2048899A (en) | 1980-12-17 |
| IT1165058B (it) | 1987-04-22 |
| DE3018473C2 (de) | 1983-01-20 |
| JPS55157624A (en) | 1980-12-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1326720C (en) | Impact resistant blends of polar thermoplastic polymers and modified block copolymers | |
| US4868245A (en) | Modified block copolymers having carboxyl groups grafted on the alkenyl arene blocks | |
| US5473034A (en) | Method for producing protein-synthetic polymer conjugate and said conjugate produced thereby | |
| Rzayev | Graft copolymers of maleic anhydride and its isostructural analogues: high performance engineering materials | |
| US5206300A (en) | Functionalized elastomeric polymers | |
| US5239010A (en) | Sulfonated block copolymers | |
| US3976628A (en) | Process for polylithiating unsaturated polymers | |
| Kanaoka et al. | Star-shaped polymers by living cationic polymerization. 3. Synthesis of heteroarm amphiphilic star-shaped polymers of vinyl ethers with hydroxyl or carboxyl pendant groups | |
| US4970254A (en) | Method for hydrogenating functionalized polymer and products thereof | |
| CA1128236A (en) | PROCESS FOR PREPARING GRAFT POLYMERS OF .alpha.,.alpha.-DISUBSTITUTED-.beta.-PROPIOLACTONES ON ISOBUTYLENE-TRIENE COPOLYMERS | |
| JP4057190B2 (ja) | ブロック共重合体 | |
| US3646166A (en) | Butyl rubber reaction products | |
| CA1326103C (en) | Method for preparing functionalized hydrocarbon polymers | |
| EP0355997B1 (en) | Polymerisation process and catalyst system therefor | |
| US4908421A (en) | Production of terminally functional polymer by cationic polymerization | |
| Liu et al. | Synthesis of novel triblock copolymers containing hydrogen-bond interaction groups via chemical modification of hydrogenated poly (styrene-block-butadiene-block-styrene) | |
| GB1589985A (en) | Method for preparation of conjugated diene butyl rubber in absence of solvent | |
| Kennedy | Functional polymers by cationic techniques | |
| CA2080120A1 (en) | Process for direct addition of acid to polymers | |
| DE69614862T2 (de) | Metallisierung und funktionalisierung von polymeren und copolymeren | |
| CA2016180C (en) | Functionalized elastomeric polymers | |
| EP1225186B1 (en) | Saturated hydrocarbon polymer having primary hydroxyl group at its end and process for producing the same | |
| KR20010075583A (ko) | 이소모노올레핀/알릴 스티렌 랜덤 공중합체 및 그의관능화된 유도체 | |
| JP2002535427A (ja) | パラフィン可溶性ポリマーおよびコポリマー | |
| JPH0370706A (ja) | 官能性エラストマーポリマー |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |