CA1094246A - Polymerization initiators containing thio bridges - Google Patents
Polymerization initiators containing thio bridgesInfo
- Publication number
- CA1094246A CA1094246A CA277,484A CA277484A CA1094246A CA 1094246 A CA1094246 A CA 1094246A CA 277484 A CA277484 A CA 277484A CA 1094246 A CA1094246 A CA 1094246A
- Authority
- CA
- Canada
- Prior art keywords
- ethane
- tetrakis
- bridges
- hexakis
- polymerization
- 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
- 239000003505 polymerization initiator Substances 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 229920000642 polymer Polymers 0.000 claims abstract description 25
- 239000000178 monomer Substances 0.000 claims abstract description 16
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 14
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- 239000003999 initiator Substances 0.000 claims description 22
- 238000006116 polymerization reaction Methods 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 150000002894 organic compounds Chemical class 0.000 claims description 8
- -1 vinyl compound Chemical class 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 238000012662 bulk polymerization Methods 0.000 claims description 3
- 238000010528 free radical solution polymerization reaction Methods 0.000 claims description 3
- 239000003701 inert diluent Substances 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- TZHXWQOFCBIWTQ-UHFFFAOYSA-N tris(phenylsulfanyl)methylsulfanylbenzene Chemical compound C=1C=CC=CC=1SC(SC=1C=CC=CC=1)(SC=1C=CC=CC=1)SC1=CC=CC=C1 TZHXWQOFCBIWTQ-UHFFFAOYSA-N 0.000 claims description 3
- DYRQMMASBFTLSU-UHFFFAOYSA-N 1,1,1,2,2,2-hexakis(methylsulfanyl)ethane Chemical compound CSC(SC)(SC)C(SC)(SC)SC DYRQMMASBFTLSU-UHFFFAOYSA-N 0.000 claims description 2
- RGAYDQLAHYRDTI-UHFFFAOYSA-N 1,1,2,2,2-pentakis(cyclohexylsulfanyl)ethylsulfanylcyclohexane Chemical compound C1CCCCC1SC(C(SC1CCCCC1)(SC1CCCCC1)SC1CCCCC1)(SC1CCCCC1)SC1CCCCC1 RGAYDQLAHYRDTI-UHFFFAOYSA-N 0.000 claims description 2
- QNYICRWLQNAKCK-UHFFFAOYSA-N [1,2-bis(methylsulfanyl)-1,2,2-tris(phenylsulfanyl)ethyl]sulfanylbenzene Chemical compound C=1C=CC=CC=1SC(C(SC)(SC=1C=CC=CC=1)SC=1C=CC=CC=1)(SC)SC1=CC=CC=C1 QNYICRWLQNAKCK-UHFFFAOYSA-N 0.000 claims description 2
- VIKWCIAIVDLETK-UHFFFAOYSA-N tetrakis(methylsulfanyl)methane Chemical compound CSC(SC)(SC)SC VIKWCIAIVDLETK-UHFFFAOYSA-N 0.000 claims description 2
- FTYIYHNPEXVEAP-UHFFFAOYSA-N 1,1,2,2,2-pentakis(phenylsulfanyl)ethylsulfanylbenzene Chemical compound C=1C=CC=CC=1SC(C(SC=1C=CC=CC=1)(SC=1C=CC=CC=1)SC=1C=CC=CC=1)(SC=1C=CC=CC=1)SC1=CC=CC=C1 FTYIYHNPEXVEAP-UHFFFAOYSA-N 0.000 claims 1
- RCKJHVNFCLHQLP-UHFFFAOYSA-N 1,1,2-tris(phenylsulfanyl)ethylsulfanylbenzene Chemical compound C=1C=CC=CC=1SC(SC=1C=CC=CC=1)(SC=1C=CC=CC=1)CSC1=CC=CC=C1 RCKJHVNFCLHQLP-UHFFFAOYSA-N 0.000 claims 1
- HOXINJBQVZWYGZ-UHFFFAOYSA-N fenbutatin oxide Chemical compound C=1C=CC=CC=1C(C)(C)C[Sn](O[Sn](CC(C)(C)C=1C=CC=CC=1)(CC(C)(C)C=1C=CC=CC=1)CC(C)(C)C=1C=CC=CC=1)(CC(C)(C)C=1C=CC=CC=1)CC(C)(C)C1=CC=CC=C1 HOXINJBQVZWYGZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 238000006011 modification reaction Methods 0.000 claims 1
- 230000003647 oxidation Effects 0.000 abstract description 2
- 238000007254 oxidation reaction Methods 0.000 abstract description 2
- 229920013730 reactive polymer Polymers 0.000 abstract 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- 229960005349 sulfur Drugs 0.000 description 6
- 235000001508 sulfur Nutrition 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 125000004149 thio group Chemical group *S* 0.000 description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 125000005396 acrylic acid ester group Chemical group 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical class ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 206010013457 Dissociation Diseases 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005250 alkyl acrylate group Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 208000018459 dissociative disease Diseases 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000000611 organothio group Chemical group 0.000 description 1
- 150000002976 peresters Chemical class 0.000 description 1
- 125000005634 peroxydicarbonate group Chemical group 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical class C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 239000012748 slip agent Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- XJKDVAABJDYCAO-UHFFFAOYSA-N trimethyl-[1,1,2,2-tetrakis(methylsulfanyl)-2-trimethylsilylethyl]silane Chemical compound CSC(SC)([Si](C)(C)C)C(SC)(SC)[Si](C)(C)C XJKDVAABJDYCAO-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229920001567 vinyl ester resin Polymers 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
- C08F4/00—Polymerisation catalysts
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/20—Incorporating sulfur atoms into the molecule
-
- 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
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
-
- 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
- C08F8/34—Introducing sulfur atoms or sulfur-containing groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762624631 DE2624631A1 (de) | 1976-06-02 | 1976-06-02 | Thiobruecken enthaltende polymerisationsinitiatoren |
| DEP2624631.1 | 1976-06-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1094246A true CA1094246A (en) | 1981-01-20 |
Family
ID=5979563
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA277,484A Expired CA1094246A (en) | 1976-06-02 | 1977-05-03 | Polymerization initiators containing thio bridges |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4121027A (enExample) |
| BE (1) | BE855239A (enExample) |
| CA (1) | CA1094246A (enExample) |
| DE (1) | DE2624631A1 (enExample) |
| FR (1) | FR2353566A1 (enExample) |
| GB (1) | GB1576040A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3504168A1 (de) * | 1985-02-07 | 1986-08-07 | Bayer Ag, 5090 Leverkusen | Verfahren zur quasi-ionischen polymerisation von polaren monomeren mit einer in (alpha)-stellung zur polaren gruppe befindlichen doppelbindung |
| US6372855B1 (en) * | 1998-08-31 | 2002-04-16 | The Yokohama Rubber Co., Ltd. | Polymer containing isobutylene as repeating unit and rubber composition containing the same |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL197603A (enExample) * | 1954-05-28 | |||
| FR1128202A (fr) * | 1954-07-30 | 1957-01-03 | Degussa | Procédé pour polymériser des composés organiques |
| US3337518A (en) * | 1964-01-24 | 1967-08-22 | Exxon Research Engineering Co | Polymerization initiators consisting of halogenated sulfur containing organic compounds having at least one s(o)n functional group |
| US3409565A (en) * | 1964-09-18 | 1968-11-05 | Goodyear Tire & Rubber | Olefin oxide and olefin sulfide polymerization |
| US3555066A (en) * | 1968-12-13 | 1971-01-12 | Dow Corning | Organo-lithium derivatives of alpha-silylmethyl sulfides |
-
1976
- 1976-06-02 DE DE19762624631 patent/DE2624631A1/de not_active Withdrawn
-
1977
- 1977-05-02 US US05/792,881 patent/US4121027A/en not_active Expired - Lifetime
- 1977-05-03 CA CA277,484A patent/CA1094246A/en not_active Expired
- 1977-05-31 BE BE178074A patent/BE855239A/xx not_active IP Right Cessation
- 1977-05-31 FR FR7716492A patent/FR2353566A1/fr active Granted
- 1977-06-01 GB GB23096/77A patent/GB1576040A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2353566A1 (fr) | 1977-12-30 |
| FR2353566B1 (enExample) | 1983-10-14 |
| US4121027A (en) | 1978-10-17 |
| DE2624631A1 (de) | 1977-12-22 |
| BE855239A (fr) | 1977-11-30 |
| GB1576040A (en) | 1980-10-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |