DE2545314A1 - Verfahren zur verbesserung der eigenschaften von dien-elastomeren - Google Patents
Verfahren zur verbesserung der eigenschaften von dien-elastomerenInfo
- Publication number
- DE2545314A1 DE2545314A1 DE19752545314 DE2545314A DE2545314A1 DE 2545314 A1 DE2545314 A1 DE 2545314A1 DE 19752545314 DE19752545314 DE 19752545314 DE 2545314 A DE2545314 A DE 2545314A DE 2545314 A1 DE2545314 A1 DE 2545314A1
- Authority
- DE
- Germany
- Prior art keywords
- polymer
- solution
- properties
- reaction
- xylene
- 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.)
- Pending
Links
- 229920001971 elastomer Polymers 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 6
- 239000000806 elastomer Substances 0.000 title claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 5
- 150000005840 aryl radicals Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- -1 aluminum compound Chemical class 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- 229920003244 diene elastomer Polymers 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 229920000642 polymer Polymers 0.000 description 41
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 22
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 16
- 239000008096 xylene Substances 0.000 description 13
- 239000005062 Polybutadiene Substances 0.000 description 10
- 229920002857 polybutadiene Polymers 0.000 description 10
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229940073608 benzyl chloride Drugs 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000005299 abrasion Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229920003051 synthetic elastomer Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DMHZDOTYAVHSEH-UHFFFAOYSA-N 1-(chloromethyl)-4-methylbenzene Chemical compound CC1=CC=C(CCl)C=C1 DMHZDOTYAVHSEH-UHFFFAOYSA-N 0.000 description 1
- HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical compound CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 description 1
- OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 230000033228 biological regulation Effects 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004455 differential thermal analysis Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920003245 polyoctenamer Polymers 0.000 description 1
- 229920003246 polypentenamer Polymers 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT28208/74A IT1030698B (it) | 1974-10-09 | 1974-10-09 | Procedimento per migliorare le caretteristiche di elastomeri polidienici e elastomeri moduficati cosi ottenuti |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2545314A1 true DE2545314A1 (de) | 1976-04-15 |
Family
ID=11223140
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752545314 Pending DE2545314A1 (de) | 1974-10-09 | 1975-10-09 | Verfahren zur verbesserung der eigenschaften von dien-elastomeren |
Country Status (15)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5938915B2 (ja) * | 2011-10-05 | 2016-06-22 | 宇部興産株式会社 | ポリブタジエンゴムの製造方法 |
| JP5982873B2 (ja) * | 2012-02-29 | 2016-08-31 | 宇部興産株式会社 | ポリブタジエンゴムおよびその製造方法 |
| JP6015758B2 (ja) | 2012-07-30 | 2016-10-26 | 宇部興産株式会社 | 変性シス−１，４−ポリブタジエンの製造方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1495372A1 (de) * | 1964-07-30 | 1969-04-10 | Huels Chemische Werke Ag | Verfahren zur definierten Erhoehung des Molekulargewichtes ungesaettigter polymerer Kohlenwasserstoffe |
| JPS531318B1 (enrdf_load_stackoverflow) * | 1971-06-25 | 1978-01-18 |
-
1974
- 1974-10-09 IT IT28208/74A patent/IT1030698B/it active
-
1975
- 1975-09-22 ZA ZA00756008A patent/ZA756008B/xx unknown
- 1975-09-23 IL IL48160A patent/IL48160A0/xx unknown
- 1975-09-23 AU AU85090/75A patent/AU8509075A/en not_active Expired
- 1975-10-06 BE BE160711A patent/BE834219A/xx unknown
- 1975-10-07 DK DK451575A patent/DK451575A/da unknown
- 1975-10-07 GB GB41113/75A patent/GB1520467A/en not_active Expired
- 1975-10-07 NO NO753377A patent/NO753377L/no unknown
- 1975-10-07 JP JP50120371A patent/JPS5163891A/ja active Pending
- 1975-10-07 FR FR7530688A patent/FR2287456A1/fr active Granted
- 1975-10-07 LU LU73539A patent/LU73539A1/xx unknown
- 1975-10-08 DD DD188749A patent/DD120448A5/xx unknown
- 1975-10-08 SE SE7511280A patent/SE7511280L/xx unknown
- 1975-10-09 DE DE19752545314 patent/DE2545314A1/de active Pending
- 1975-10-09 NL NL7511910A patent/NL7511910A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5163891A (en) | 1976-06-02 |
| DK451575A (da) | 1976-04-10 |
| NO753377L (enrdf_load_stackoverflow) | 1976-04-12 |
| BE834219A (fr) | 1976-04-06 |
| IT1030698B (it) | 1979-04-10 |
| LU73539A1 (enrdf_load_stackoverflow) | 1976-06-11 |
| SE7511280L (sv) | 1976-04-12 |
| GB1520467A (en) | 1978-08-09 |
| NL7511910A (nl) | 1976-04-13 |
| IL48160A0 (en) | 1975-11-25 |
| FR2287456B1 (enrdf_load_stackoverflow) | 1978-03-17 |
| FR2287456A1 (fr) | 1976-05-07 |
| DD120448A5 (enrdf_load_stackoverflow) | 1976-06-12 |
| ZA756008B (en) | 1976-09-29 |
| AU8509075A (en) | 1977-03-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OGA | New person/name/address of the applicant | ||
| OHJ | Non-payment of the annual fee |