DE2010708B2 - Verwendung von alkylenpolyaminen als stabilisatoren in einer hocharomatischen, gekuppelte loesungspolymerisate enthaltenden oelgrundmischung - Google Patents
Verwendung von alkylenpolyaminen als stabilisatoren in einer hocharomatischen, gekuppelte loesungspolymerisate enthaltenden oelgrundmischungInfo
- Publication number
- DE2010708B2 DE2010708B2 DE19702010708 DE2010708A DE2010708B2 DE 2010708 B2 DE2010708 B2 DE 2010708B2 DE 19702010708 DE19702010708 DE 19702010708 DE 2010708 A DE2010708 A DE 2010708A DE 2010708 B2 DE2010708 B2 DE 2010708B2
- Authority
- DE
- Germany
- Prior art keywords
- highly aromatic
- oil base
- stabilizers
- astm
- polymerisates
- 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
- 239000000203 mixture Substances 0.000 title description 26
- 239000010692 aromatic oil Substances 0.000 title description 10
- 229920000768 polyamine Polymers 0.000 title description 10
- 239000003381 stabilizer Substances 0.000 title description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 229920000642 polymer Polymers 0.000 description 30
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 18
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 18
- 239000003921 oil Substances 0.000 description 13
- 229910003902 SiCl 4 Inorganic materials 0.000 description 12
- 239000003999 initiator Substances 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 9
- 150000001993 dienes Chemical class 0.000 description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000007822 coupling agent Substances 0.000 description 6
- 239000000178 monomer Substances 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 241001441571 Hiodontidae Species 0.000 description 4
- 150000001491 aromatic compounds Chemical class 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000005060 rubber Substances 0.000 description 4
- 230000000087 stabilizing effect Effects 0.000 description 4
- 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 3
- 230000007423 decrease Effects 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- -1 3-ethyl-1,4-diaminocyclooctane Chemical compound 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000002993 cycloalkylene group Chemical group 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- SUHREOTWWVNREO-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;lithium Chemical compound [Li].C=CC1=CC=CC=C1C=C SUHREOTWWVNREO-UHFFFAOYSA-N 0.000 description 1
- CORMBJOFDGICKF-UHFFFAOYSA-N 1,3,5-trimethoxy 2-vinyl benzene Natural products COC1=CC(OC)=C(C=C)C(OC)=C1 CORMBJOFDGICKF-UHFFFAOYSA-N 0.000 description 1
- WJNKJKGZKFOLOJ-UHFFFAOYSA-N 1-dodecyl-4-ethenylbenzene Chemical compound CCCCCCCCCCCCC1=CC=C(C=C)C=C1 WJNKJKGZKFOLOJ-UHFFFAOYSA-N 0.000 description 1
- CDVJOHHCJGQSJH-UHFFFAOYSA-N 1-ethenyl-2,3,4,5-tetramethylbenzene Chemical compound CC1=CC(C=C)=C(C)C(C)=C1C CDVJOHHCJGQSJH-UHFFFAOYSA-N 0.000 description 1
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- PDELBHCVXBSVPJ-UHFFFAOYSA-N 2-ethenyl-1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=C(C=C)C(C)=C1 PDELBHCVXBSVPJ-UHFFFAOYSA-N 0.000 description 1
- KWTIARNLEYBFNK-UHFFFAOYSA-N 2-ethenyl-3-ethylnaphthalene Chemical compound C1=CC=C2C=C(C=C)C(CC)=CC2=C1 KWTIARNLEYBFNK-UHFFFAOYSA-N 0.000 description 1
- KXYAVSFOJVUIHT-UHFFFAOYSA-N 2-vinylnaphthalene Chemical compound C1=CC=CC2=CC(C=C)=CC=C21 KXYAVSFOJVUIHT-UHFFFAOYSA-N 0.000 description 1
- OCTVDLUSQOJZEK-UHFFFAOYSA-N 4,5-diethylocta-1,3-diene Chemical compound CCCC(CC)C(CC)=CC=C OCTVDLUSQOJZEK-UHFFFAOYSA-N 0.000 description 1
- MHKLKWCYGIBEQF-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-ylsulfanyl)morpholine Chemical compound C1COCCN1SC1=NC2=CC=CC=C2S1 MHKLKWCYGIBEQF-UHFFFAOYSA-N 0.000 description 1
- RRGRCBYNXFIHGR-UHFFFAOYSA-N 8-butyl-3-ethenyl-1-propylnaphthalene Chemical compound C=CC1=CC(CCC)=C2C(CCCC)=CC=CC2=C1 RRGRCBYNXFIHGR-UHFFFAOYSA-N 0.000 description 1
- IVAHJKXSKBAXHT-UHFFFAOYSA-N C1(CCCC1)C(CCCN)CCCCN Chemical compound C1(CCCC1)C(CCCN)CCCCN IVAHJKXSKBAXHT-UHFFFAOYSA-N 0.000 description 1
- MNJBRSYJNIFBRT-UHFFFAOYSA-N C1=CC=C2C(C)(C=C)CC=CC2=C1 Chemical compound C1=CC=C2C(C)(C=C)CC=CC2=C1 MNJBRSYJNIFBRT-UHFFFAOYSA-N 0.000 description 1
- 229920000818 Catalin Polymers 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241000872198 Serjania polyphylla Species 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
- 238000005299 abrasion Methods 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 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
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- NHWGPUVJQFTOQX-UHFFFAOYSA-N ethyl-[2-[2-[ethyl(dimethyl)azaniumyl]ethyl-methylamino]ethyl]-dimethylazanium Chemical compound CC[N+](C)(C)CCN(C)CC[N+](C)(C)CC NHWGPUVJQFTOQX-UHFFFAOYSA-N 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 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
- 125000001979 organolithium group Chemical group 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- HDBWAWNLGGMZRQ-UHFFFAOYSA-N p-Vinylbiphenyl Chemical compound C1=CC(C=C)=CC=C1C1=CC=CC=C1 HDBWAWNLGGMZRQ-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 229920006216 polyvinyl aromatic Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000004636 vulcanized rubber Substances 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 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
- C08C19/30—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule
- C08C19/42—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups
- C08C19/44—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups of polymers containing metal atoms exclusively at one or both ends of the skeleton
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80535669A | 1969-03-07 | 1969-03-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2010708A1 DE2010708A1 (de) | 1970-09-24 |
| DE2010708B2 true DE2010708B2 (de) | 1973-04-12 |
Family
ID=25191352
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702010708 Pending DE2010708B2 (de) | 1969-03-07 | 1970-03-06 | Verwendung von alkylenpolyaminen als stabilisatoren in einer hocharomatischen, gekuppelte loesungspolymerisate enthaltenden oelgrundmischung |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3640939A (enExample) |
| JP (1) | JPS4833622B1 (enExample) |
| BE (1) | BE746944A (enExample) |
| CA (1) | CA925639A (enExample) |
| DE (1) | DE2010708B2 (enExample) |
| ES (1) | ES377199A1 (enExample) |
| FR (1) | FR2037467A5 (enExample) |
| GB (1) | GB1297193A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3769216A (en) * | 1971-02-26 | 1973-10-30 | Chevron Res | Nitrogenous ethylene/propylene copolymers and lubricants containing them |
| US6279632B1 (en) * | 1999-11-24 | 2001-08-28 | Bridgestone Corporation | Method to control increase in viscosity during aging of siloxane modified polymers |
-
1969
- 1969-03-07 US US805356A patent/US3640939A/en not_active Expired - Lifetime
-
1970
- 1970-02-23 CA CA075594A patent/CA925639A/en not_active Expired
- 1970-02-27 JP JP45016324A patent/JPS4833622B1/ja active Pending
- 1970-03-02 FR FR7007387A patent/FR2037467A5/fr not_active Expired
- 1970-03-06 ES ES377199A patent/ES377199A1/es not_active Expired
- 1970-03-06 BE BE746944D patent/BE746944A/xx unknown
- 1970-03-06 GB GB1297193D patent/GB1297193A/en not_active Expired
- 1970-03-06 DE DE19702010708 patent/DE2010708B2/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4833622B1 (enExample) | 1973-10-16 |
| DE2010708A1 (de) | 1970-09-24 |
| FR2037467A5 (enExample) | 1970-12-31 |
| BE746944A (fr) | 1970-09-07 |
| US3640939A (en) | 1972-02-08 |
| ES377199A1 (es) | 1973-01-01 |
| GB1297193A (enExample) | 1972-11-22 |
| CA925639A (en) | 1973-05-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69333870T2 (de) | Lösliche anionische Polymerisationsinitiatoren | |
| DE69116917T2 (de) | Elastomere und Produkte mit niedriger Hysteresis | |
| DE1520548B1 (de) | Verfahren zur Abwandlung von Polymerisaten konjugierter Diene | |
| DE1169674B (de) | Verfahren zur Herstellung von Umsetzungs-produkten aus hochmolekularen alkalimetall-organischen Verbindungen | |
| DE2131354B2 (de) | Verfahren zur Verbesserung der Rohfestigkeit von Kautschukmischungen | |
| DE2452931A1 (de) | Verfahren zur herstellung von synthetischen kautschukmassen | |
| DE2010708B2 (de) | Verwendung von alkylenpolyaminen als stabilisatoren in einer hocharomatischen, gekuppelte loesungspolymerisate enthaltenden oelgrundmischung | |
| DE1138917B (de) | Verstaerkerfuellstoff enthaltende kautschukartige Copolymerisatmischungen | |
| DE69026692T2 (de) | Verfahren zur Herstellung von thermoplastischen elastomeren Zusammensetzungen | |
| DE1169675B (de) | Verfahren zur Polymerisation von Isopren oder Butadien | |
| DE1795229B2 (de) | Verfahren zur Herstellung eines Polymerengemisches | |
| DE1620836C3 (de) | Kautschukmischung | |
| DE3615979C2 (enExample) | ||
| DE2356656A1 (de) | Chloroprengummi | |
| DE69311646T2 (de) | Kautschukmischung sowie deren Herstellung | |
| DE1233135B (de) | Waermevulkanisierbare Formmassen aus Acrylsaeureesterpolymerisaten | |
| DE1595295C3 (de) | Verfahren zum Behandeln von synthetischem Kautschuk | |
| DE963471C (de) | Verfahren zur Bearbeitung von Kautschuk-Russ-Mischungen | |
| DE677433C (de) | Verfahren zur Herstellung von kautschukartigen Polymerisationsprodukten aus Butadienoder dessen Substitutionsprodukten | |
| DE1520548C2 (de) | Verfahren zur Abwandlung von Polymerisaten konjugierter Diene | |
| DE852904C (de) | Verfahren zum Vulkanisieren eines synthetischen, mit Schwefel vulkanisierbaren, kautschukaehnlichen Mischpolymeren eines Butadien-1, 3-Kohlenwasserstoffs und einer Monovinylverbindung | |
| DE2015855A1 (de) | Polvmensatmischungen | |
| DE1225392B (de) | Verfahren zur Herstellung von Abwandlungs-produkten von Butadien-Polymerisaten | |
| DE1620837A1 (de) | Latexmischung | |
| DEU0002469MA (enExample) |