CA1080389A - Polymers and copolymers of indene grafted on elastomeric chains and processes for their production - Google Patents
Polymers and copolymers of indene grafted on elastomeric chains and processes for their productionInfo
- Publication number
- CA1080389A CA1080389A CA239,779A CA239779A CA1080389A CA 1080389 A CA1080389 A CA 1080389A CA 239779 A CA239779 A CA 239779A CA 1080389 A CA1080389 A CA 1080389A
- Authority
- CA
- Canada
- Prior art keywords
- indene
- elastomers
- grafted
- process according
- copolymer
- 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
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 title claims abstract description 87
- 229920001577 copolymer Polymers 0.000 title claims abstract description 37
- 229920000642 polymer Polymers 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 title claims description 34
- 238000004519 manufacturing process Methods 0.000 title abstract description 5
- 229920001971 elastomer Polymers 0.000 claims abstract description 40
- 239000000806 elastomer Substances 0.000 claims abstract description 36
- 229920000578 graft copolymer Polymers 0.000 claims abstract description 18
- 239000000470 constituent Substances 0.000 claims abstract description 16
- 239000002904 solvent Substances 0.000 claims abstract description 9
- 150000003440 styrenes Chemical class 0.000 claims abstract description 9
- 125000005843 halogen group Chemical group 0.000 claims abstract description 7
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims abstract 6
- 229920001169 thermoplastic Polymers 0.000 claims description 28
- 239000004416 thermosoftening plastic Substances 0.000 claims description 28
- 229920005556 chlorobutyl Polymers 0.000 claims description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 20
- 239000000178 monomer Substances 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 239000003999 initiator Substances 0.000 claims description 19
- -1 ethylene, propylene Chemical group 0.000 claims description 17
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 16
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 12
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical group CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 claims description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 8
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 8
- 239000002841 Lewis acid Substances 0.000 claims description 6
- 150000007517 lewis acids Chemical class 0.000 claims description 6
- 229910008046 SnC14 Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 239000012836 macromolecular constituent Substances 0.000 claims description 3
- 238000010538 cationic polymerization reaction Methods 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 239000011877 solvent mixture Substances 0.000 claims description 2
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical group CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 claims description 2
- 150000005673 monoalkenes Chemical class 0.000 claims 5
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims 2
- 241000352333 Amegilla alpha Species 0.000 claims 1
- 229910003074 TiCl4 Inorganic materials 0.000 claims 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims 1
- 239000000460 chlorine Substances 0.000 abstract description 9
- 229920002725 thermoplastic elastomer Polymers 0.000 abstract description 7
- 239000003054 catalyst Substances 0.000 abstract description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052801 chlorine Inorganic materials 0.000 abstract description 2
- 125000002091 cationic group Chemical group 0.000 description 6
- 229920001519 homopolymer Polymers 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- 239000005060 rubber Substances 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 3
- 150000001348 alkyl chlorides Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 229920005549 butyl rubber Polymers 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000012815 thermoplastic material Substances 0.000 description 2
- 238000004073 vulcanization Methods 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 229910010066 TiC14 Inorganic materials 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005234 alkyl aluminium group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 244000309464 bull Species 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
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 229910052739 hydrogen Chemical group 0.000 description 1
- 239000001257 hydrogen Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 229920006132 styrene block copolymer Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000006276 transfer reaction Methods 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
- C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Graft Or Block Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7437856A FR2291234A1 (fr) | 1974-11-18 | 1974-11-18 | Polymeres et copolymeres de l'indene greffes sur des chaines elastomeres |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1080389A true CA1080389A (en) | 1980-06-24 |
Family
ID=9145002
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA239,779A Expired CA1080389A (en) | 1974-11-18 | 1975-11-17 | Polymers and copolymers of indene grafted on elastomeric chains and processes for their production |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4105713A (enExample) |
| JP (1) | JPS5173591A (enExample) |
| CA (1) | CA1080389A (enExample) |
| DE (1) | DE2550717A1 (enExample) |
| FR (1) | FR2291234A1 (enExample) |
| GB (1) | GB1517225A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6900273B1 (en) * | 1999-06-28 | 2005-05-31 | Hitachi Chemical Co., Ltd. | Low-hygroscopicity low-birefringence resin compositions, molding material obtained therefrom, sheet or film, and optical part |
| US6384147B1 (en) * | 2001-03-19 | 2002-05-07 | University Of Akron | Poly(vinyl chloride)-g-poly(α-methylstyrene) having a single glass transition temperature |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3904708A (en) * | 1966-07-26 | 1975-09-09 | Joseph P Kennedy | Process for graft polymerization |
-
1974
- 1974-11-18 FR FR7437856A patent/FR2291234A1/fr active Granted
-
1975
- 1975-11-12 DE DE19752550717 patent/DE2550717A1/de not_active Withdrawn
- 1975-11-14 US US05/631,991 patent/US4105713A/en not_active Expired - Lifetime
- 1975-11-17 GB GB47264/75A patent/GB1517225A/en not_active Expired
- 1975-11-17 CA CA239,779A patent/CA1080389A/en not_active Expired
- 1975-11-18 JP JP50137865A patent/JPS5173591A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5173591A (enExample) | 1976-06-25 |
| FR2291234A1 (fr) | 1976-06-11 |
| DE2550717A1 (de) | 1976-05-26 |
| FR2291234B1 (enExample) | 1978-07-07 |
| GB1517225A (en) | 1978-07-12 |
| US4105713A (en) | 1978-08-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |