CN1780859B - 获得沿链含有官能团的接枝弹性体的方法和橡胶组合物 - Google Patents
获得沿链含有官能团的接枝弹性体的方法和橡胶组合物 Download PDFInfo
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- CN1780859B CN1780859B CN200480011490XA CN200480011490A CN1780859B CN 1780859 B CN1780859 B CN 1780859B CN 200480011490X A CN200480011490X A CN 200480011490XA CN 200480011490 A CN200480011490 A CN 200480011490A CN 1780859 B CN1780859 B CN 1780859B
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- 230000002950 deficient Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- DPUXQWOMYBMHRN-UHFFFAOYSA-N hexa-2,3-diene Chemical compound CCC=C=CC DPUXQWOMYBMHRN-UHFFFAOYSA-N 0.000 description 1
- HTDJPCNNEPUOOQ-UHFFFAOYSA-N hexamethylcyclotrisiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O1 HTDJPCNNEPUOOQ-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- CCZVEWRRAVASGL-UHFFFAOYSA-N lithium;2-methanidylpropane Chemical compound [Li+].CC(C)[CH2-] CCZVEWRRAVASGL-UHFFFAOYSA-N 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000004702 methyl esters Chemical group 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000012764 mineral filler Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000000399 optical microscopy Methods 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- 238000002103 osmometry Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 229920003192 poly(bis maleimide) Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 238000003756 stirring 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
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical group O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- NESLVXDUKMNMOG-UHFFFAOYSA-N triethoxy-(propyltetrasulfanyl)silane Chemical compound CCCSSSS[Si](OCC)(OCC)OCC NESLVXDUKMNMOG-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
- B60C1/0016—Compositions of the tread
-
- 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
- C08F279/00—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00
- C08F279/02—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00 on to polymers of conjugated dienes
-
- 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
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
-
- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L51/04—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to rubbers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02T—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO TRANSPORTATION
- Y02T10/00—Road transport of goods or passengers
- Y02T10/80—Technologies aiming to reduce greenhouse gasses emissions common to all road transportation technologies
- Y02T10/86—Optimisation of rolling resistance, e.g. weight reduction
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)
- Mechanical Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
SBR | 加入SBR中的 6-PPD的量 (检验结果) | 硫醇的 加入量 (meq./kg) | 最终门尼 ML(1+4) | Mn 克/摩尔 (SEC) | Ip (SEC) | COOH 基团的量 (meq/kg) (<sup>1</sup>H NMR) | 接枝 收率 (%) |
SBR 1 | 0.4phr (0.39) | - | 33.6 | 130871 | 1.16 | - | - |
SBR 2 | 0 (<0.02) | 80 | 54 | 134603 | 1.22 | 46 | 58% |
SBR 3 | 0.4phr (0.39) | 160 | 40.5 | 133276 | 1.23 | 37 | 23% |
SBR的性质 | 含有0.39phr的6-PPD |
接枝后的处理 | 官能团的量(IR) (meq./kg) |
汽提 | SBR 3a:57 |
汽提和一次凝结 | SBR 3b:54 |
汽提和二次凝结 | SBR 3c:56 |
弹性体 | 100 |
二氧化硅(1) | 80 |
芳香油(“ENERDEX 65”)(5) | 39.5 |
键合剂(2) | 6.4 |
ZnO | 2.5 |
硬脂酸 | 2 |
抗氧化剂(3) | 1.9 |
抗臭氧蜡“C32ST”(6) | 1.5 |
硫 | 1.2 |
次磺酰胺(4) | 2 |
二苯胍 | 1.5 |
最终SBR | 最终 ML(1+4) | Mn 克/摩尔 (SEC) | Ip (SEC) | COOH基团的 量(meq/kg) (<sup>1</sup>H NMR) | 接枝收 率(%) |
SBR 4a | 42 | 132996 | 1.18 | 38 | 25 |
SBR 4b | 41 | 142300 | 1.30 | 80 | 66 |
SBR 5a | 49 | 134796 | 1.29 | 46 | 30.5 |
SBR 5b | 35 | 129978 | 1.14 | 17 | 11 |
弹性体 | 75 |
PB 113 | 25 |
二氧化硅(1) | 80 |
芳香油(“ENERDEX 65”)(5) | 37 |
键合剂(2) | 6.4 |
ZnO | 2.5 |
硬脂酸 | 2 |
抗氧化剂(3) | 1.9 |
抗臭氧蜡“C32ST”(6) | 1.5 |
硫 | 1.2 |
次磺酰胺(4) | 2 |
二苯胍 | 1.5 |
弹性体 | 100 |
二氧化硅(1) | 50 |
键合剂(2) | 8 |
ZnO | 2.5 |
硬脂酸 | 2 |
抗氧化剂(3) | 2 |
石蜡 | 1 |
硫 | 1.2 |
次磺酰胺(4) | 1.2 |
二苯胍 | 1 |
ZBEC(5) | 0.2 |
弹性体 | 100 |
二氧化硅(1) | 50 |
键合剂(2) | 8 |
ZnO | 2.5 |
硬脂酸 | 2 |
抗氧化剂(3) | 2 |
石蜡 | 1 |
硫 | 1.2 |
次磺酰胺(4) | 1.2 |
二苯胍 | 1 |
ZBEC(5) | 0.2 |
弹性体 | 100 |
二氧化硅(1) | 80 |
芳香油(“ENERDEX 65”)(5) | 39.5 |
键合剂(2) | 6.4 |
ZnO | 2.5 |
硬脂酸 | 2 |
抗氧化剂(3) | 1.9 |
抗臭氧蜡“C32ST”(6) | 1.5 |
硫 | 1.2 |
次磺酰胺(4) | 2 |
二苯胍 | 1.5 |
Claims (21)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR03/05305 | 2003-04-29 | ||
FR0305305A FR2854404B1 (fr) | 2003-04-29 | 2003-04-29 | Procede d'obtention d'un elastomere greffe a groupes fonctionnels le long de la chaine et compositions de caoutchouc |
PCT/EP2004/004510 WO2004096865A2 (fr) | 2003-04-29 | 2004-04-29 | Procede d’obtention d’un elastomere greffe a groupes fonctionnels le long de la chaîne et composition de caoutchouc |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1780859A CN1780859A (zh) | 2006-05-31 |
CN1780859B true CN1780859B (zh) | 2010-11-03 |
Family
ID=33155561
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN200480011490XA Expired - Fee Related CN1780859B (zh) | 2003-04-29 | 2004-04-29 | 获得沿链含有官能团的接枝弹性体的方法和橡胶组合物 |
Country Status (10)
Country | Link |
---|---|
US (1) | US7312264B2 (zh) |
EP (1) | EP1620471A2 (zh) |
JP (1) | JP4874791B2 (zh) |
KR (1) | KR101186129B1 (zh) |
CN (1) | CN1780859B (zh) |
AU (1) | AU2004234058A1 (zh) |
BR (1) | BRPI0409806A (zh) |
FR (1) | FR2854404B1 (zh) |
RU (1) | RU2337923C2 (zh) |
WO (1) | WO2004096865A2 (zh) |
Families Citing this family (266)
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WO2021054428A1 (ja) * | 2019-09-20 | 2021-03-25 | 株式会社クラレ | 共役ジエン系グラフト重合体、およびその製造方法 |
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- 2004-04-29 KR KR1020057020539A patent/KR101186129B1/ko not_active IP Right Cessation
- 2004-04-29 AU AU2004234058A patent/AU2004234058A1/en not_active Abandoned
- 2004-04-29 JP JP2006505312A patent/JP4874791B2/ja not_active Expired - Fee Related
- 2004-04-29 BR BRPI0409806-4A patent/BRPI0409806A/pt not_active Application Discontinuation
- 2004-04-29 CN CN200480011490XA patent/CN1780859B/zh not_active Expired - Fee Related
- 2004-04-29 EP EP04730253A patent/EP1620471A2/fr not_active Withdrawn
- 2004-04-29 WO PCT/EP2004/004510 patent/WO2004096865A2/fr active Application Filing
- 2004-04-29 RU RU2005136980/04A patent/RU2337923C2/ru not_active IP Right Cessation
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2005
- 2005-10-25 US US11/256,986 patent/US7312264B2/en not_active Expired - Lifetime
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GB1575115A (en) * | 1976-11-23 | 1980-09-17 | Bayer Ag | Process for the production of polybutadiene |
CN1169151A (zh) * | 1995-10-19 | 1997-12-31 | 埃尔夫·阿奎坦 | 由接枝羧基或酯基官能化的弹性体及其在生产用于制备涂料的官能化弹性体/沥青组合物的用途 |
EP1000971B1 (de) * | 1998-11-16 | 2003-10-15 | Bayer Aktiengesellschaft | Carboxylgruppen-haltige Lösungskautschuke enthaltende Kautschukmischungen |
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Publication number | Publication date |
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AU2004234058A1 (en) | 2004-11-11 |
BRPI0409806A (pt) | 2006-05-09 |
EP1620471A2 (fr) | 2006-02-01 |
US20060089445A1 (en) | 2006-04-27 |
WO2004096865A3 (fr) | 2005-02-10 |
RU2337923C2 (ru) | 2008-11-10 |
WO2004096865A2 (fr) | 2004-11-11 |
JP4874791B2 (ja) | 2012-02-15 |
KR20060008938A (ko) | 2006-01-27 |
FR2854404B1 (fr) | 2005-07-01 |
US7312264B2 (en) | 2007-12-25 |
JP2006524725A (ja) | 2006-11-02 |
KR101186129B1 (ko) | 2012-09-27 |
RU2005136980A (ru) | 2006-03-20 |
CN1780859A (zh) | 2006-05-31 |
FR2854404A1 (fr) | 2004-11-05 |
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