CA1333205C - Agents de vulcanisation et methodes de preparation - Google Patents

Agents de vulcanisation et methodes de preparation

Info

Publication number: CA1333205C
Authority: CA; Canada
Prior art keywords: sulfur; olefin; rubber; weight; adduct
Prior art date: 1986-08-15
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 - Fee Related

Application number

CA000616554A

Other languages

English (en)

Inventor

Charles Lee Bull, Jr.

Howard Anthony Colvin

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Goodyear Tire and Rubber Co

Original Assignee

Goodyear Tire and Rubber Co

Priority date (The priority date 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 date listed.)

1986-08-15

Filing date

1992-12-16

Publication date

1994-11-22

1986-08-15 Priority claimed from US06/896,688 external-priority patent/US4739036A/en

1992-12-16 Application filed by Goodyear Tire and Rubber Co filed Critical Goodyear Tire and Rubber Co

1994-11-22 Application granted granted Critical

1994-11-22 Publication of CA1333205C publication Critical patent/CA1333205C/fr

2007-08-14 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000003795 chemical substances by application Substances 0.000 title claims abstract description 36
238000000034 method Methods 0.000 title claims description 19
238000002360 preparation method Methods 0.000 title description 5
238000013040 rubber vulcanization Methods 0.000 title 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 108
229910052717 sulfur Inorganic materials 0.000 claims abstract description 105
239000011593 sulfur Substances 0.000 claims abstract description 105
239000000203 mixture Substances 0.000 claims abstract description 37
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 32
150000001336 alkenes Chemical class 0.000 claims abstract description 30
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 27
239000002270 dispersing agent Substances 0.000 claims abstract description 14
238000010438 heat treatment Methods 0.000 claims abstract description 14
239000003054 catalyst Substances 0.000 claims abstract description 13
238000013019 agitation Methods 0.000 claims abstract description 10
238000002156 mixing Methods 0.000 claims abstract description 10
238000004519 manufacturing process Methods 0.000 claims abstract description 5
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 36
HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims description 29
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 23
239000000463 material Substances 0.000 claims description 19
238000001816 cooling Methods 0.000 claims description 16
229920001577 copolymer Polymers 0.000 claims description 12
229920001194 natural rubber Polymers 0.000 claims description 12
229910000019 calcium carbonate Inorganic materials 0.000 claims description 11
229920003051 synthetic elastomer Polymers 0.000 claims description 11
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 10
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 10
ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 10
229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 9
239000001768 carboxy methyl cellulose Substances 0.000 claims description 9
235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 9
239000008112 carboxymethyl-cellulose Substances 0.000 claims description 9
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 7
229930195733 hydrocarbon Natural products 0.000 claims description 7
150000002430 hydrocarbons Chemical class 0.000 claims description 7
239000004215 Carbon black (E152) Substances 0.000 claims description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 claims description 5
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 5
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 5
RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 claims description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 4
229920001084 poly(chloroprene) Polymers 0.000 claims description 4
229920002857 polybutadiene Polymers 0.000 claims description 4
229920002451 polyvinyl alcohol Polymers 0.000 claims description 4
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 4
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 3
239000004372 Polyvinyl alcohol Substances 0.000 claims description 3
235000019422 polyvinyl alcohol Nutrition 0.000 claims description 3
IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 claims description 3
229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 2
229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
229920001971 elastomer Polymers 0.000 abstract description 57
239000005060 rubber Substances 0.000 abstract description 53
239000000047 product Substances 0.000 description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
238000003756 stirring Methods 0.000 description 14
239000011324 bead Substances 0.000 description 13
150000001993 dienes Chemical class 0.000 description 11
239000006185 dispersion Substances 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 10
150000001875 compounds Chemical class 0.000 description 8
239000004615 ingredient Substances 0.000 description 7
229920003052 natural elastomer Polymers 0.000 description 7
229910052757 nitrogen Inorganic materials 0.000 description 7
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 6
-1 butene-l Chemical compound 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 5
239000005061 synthetic rubber Substances 0.000 description 5
230000000704 physical effect Effects 0.000 description 4
238000012360 testing method Methods 0.000 description 4
244000043261 Hevea brasiliensis Species 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
239000000806 elastomer Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000000178 monomer Substances 0.000 description 3
229920000642 polymer Polymers 0.000 description 3
238000003860 storage Methods 0.000 description 3
238000004073 vulcanization Methods 0.000 description 3
XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 2
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
DRHABPMHZRIRAH-UHFFFAOYSA-N 2,4,4,6,6-pentamethylhept-2-ene Chemical group CC(C)=CC(C)(C)CC(C)(C)C DRHABPMHZRIRAH-UHFFFAOYSA-N 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
125000005250 alkyl acrylate group Chemical group 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
UAHWPYUMFXYFJY-UHFFFAOYSA-N beta-myrcene Chemical compound CC(C)=CCCC(=C)C=C UAHWPYUMFXYFJY-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
CRPUJAZIXJMDBK-UHFFFAOYSA-N camphene Chemical compound C1CC2C(=C)C(C)(C)C1C2 CRPUJAZIXJMDBK-UHFFFAOYSA-N 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 2
238000013329 compounding Methods 0.000 description 2
238000007334 copolymerization reaction Methods 0.000 description 2
MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
238000000113 differential scanning calorimetry Methods 0.000 description 2
235000021388 linseed oil Nutrition 0.000 description 2
239000000944 linseed oil Substances 0.000 description 2
239000002245 particle Substances 0.000 description 2
150000002978 peroxides Chemical class 0.000 description 2
229920001195 polyisoprene Polymers 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
238000012545 processing Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
229920001897 terpolymer Polymers 0.000 description 2
KEIFWROAQVVDBN-UHFFFAOYSA-N 1,2-dihydronaphthalene Chemical compound C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-UHFFFAOYSA-N 0.000 description 1
JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 1
KFVIYKFKUYBKTP-UHFFFAOYSA-N 2-n-(methoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound COCNC1=NC(N)=NC(N)=N1 KFVIYKFKUYBKTP-UHFFFAOYSA-N 0.000 description 1
YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-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
PXRCIOIWVGAZEP-UHFFFAOYSA-N Primaeres Camphenhydrat Natural products C1CC2C(O)(C)C(C)(C)C1C2 PXRCIOIWVGAZEP-UHFFFAOYSA-N 0.000 description 1
SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 1
VYBREYKSZAROCT-UHFFFAOYSA-N alpha-myrcene Natural products CC(=C)CCCC(=C)C=C VYBREYKSZAROCT-UHFFFAOYSA-N 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
230000003078 antioxidant effect Effects 0.000 description 1
238000013459 approach Methods 0.000 description 1
239000012431 aqueous reaction media Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229930006739 camphene Natural products 0.000 description 1
ZYPYEBYNXWUCEA-UHFFFAOYSA-N camphenilone Natural products C1CC2C(=O)C(C)(C)C1C2 ZYPYEBYNXWUCEA-UHFFFAOYSA-N 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
150000001925 cycloalkenes Chemical class 0.000 description 1
229920003244 diene elastomer Polymers 0.000 description 1
LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 1
229940043276 diisopropanolamine Drugs 0.000 description 1
239000000975 dye Substances 0.000 description 1
239000000945 filler Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000000227 grinding Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000013508 migration Methods 0.000 description 1
230000005012 migration Effects 0.000 description 1
238000003801 milling Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
239000012744 reinforcing agent Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
238000012552 review Methods 0.000 description 1
238000010057 rubber processing Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
150000003463 sulfur Chemical class 0.000 description 1
239000002344 surface layer Substances 0.000 description 1
150000003505 terpenes Chemical class 0.000 description 1
235000007586 terpenes Nutrition 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1

Landscapes

Compositions Of Macromolecular Compounds (AREA)

CA000616554A 1986-08-15 1992-12-16 Agents de vulcanisation et methodes de preparation Expired - Fee Related CA1333205C (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US06/896,688 US4739036A (en)	1986-08-15	1986-08-15	Rubber vulcanization agents and methods for their preparation
US896,688		1986-08-15
CA000544549A CA1324450C (fr)	1986-08-15	1987-08-14	Agents de vulcanisation du caoutchouc, et methode de preparation connexe

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000544549A Division CA1324450C (fr)	1986-08-15	1987-08-14	Agents de vulcanisation du caoutchouc, et methode de preparation connexe

Publications (1)

Publication Number	Publication Date
CA1333205C true CA1333205C (fr)	1994-11-22

Family

ID=25671472

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000616554A Expired - Fee Related CA1333205C (fr)	1986-08-15	1992-12-16	Agents de vulcanisation et methodes de preparation

Country Status (1)

Country	Link
CA (1)	CA1333205C (fr)

1992
- 1992-12-16 CA CA000616554A patent/CA1333205C/fr not_active Expired - Fee Related

Legal Events

Date	Code	Title	Description
1999-11-22	MKLA	Lapsed

Publication	Publication Date	Title
EP0258168B1 (fr)	1995-12-27	Agent de vulcanisation pour caoutchouc et leurs méthodes de préparation
US4752507A (en)	1988-06-21	Rubber vulcanizing agents comprising reaction products of sulfur and unsaturated hydrocarbons
US2989513A (en)	1961-06-20	Curing of rubber with a sulfur-olefinic hydrocarbon interpolymer, and product obtained thereby
US4740559A (en)	1988-04-26	Rubber vulcanizing agents comprising reaction products of sulfur and unsaturated hydrocarbons
EP0066241B1 (fr)	1985-05-08	Caoutchouc de polyisoprène-1,4 cis modifié, un procédé pour sa préparation, une composition de caoutchouc de polyisoprène-1,4 cis modifié et vulcanisé et l'application du caoutchouc de polyisoprène-1,4 cis modifié pour la fabrication d'objets moulés
US2332194A (en)	1943-10-19	Rubberlike composition and process for making the same
EP0775718A2 (fr)	1997-05-28	Procédé de production des compositions d'élastomères de granulats d'élastomères et polymères
US4902775A (en)	1990-02-20	Rubber vulcanization agents of sulfur olefin adduct
US4792589A (en)	1988-12-20	Rubber vulcanization agents of sulfur and olefin
JPS63278948A (ja)	1988-11-16	ベンズイミダゾリノンで変性したゴム組成物
JPS63284240A (ja)	1988-11-21	複素環式ジ‐ｎ‐オキシドで変性したゴム組成物
US3264239A (en)	1966-08-02	Vulcanizing agent prepared from sulfur, linseed oil and dicyclopentadiene
CA1333205C (fr)	1994-11-22	Agents de vulcanisation et methodes de preparation
US4431765A (en)	1984-02-14	Free flowing polybutadiene resin particles and process for the preparation thereof
JP2008214644A (ja)	2008-09-18	架橋性エラストマー組成物を調製するための細分割形態の生成物
US3544492A (en)	1970-12-01	Sulfur-containing curing agents
US2429439A (en)	1947-10-21	Method of producing butadiene styrene copolymer reinforced with calcium silicate
US2656324A (en)	1953-10-20	Method of making rubbery compounds suitable for production of tire treads
US3259598A (en)	1966-07-05	Vulcanizing agent prepared from sulfur, linseed oil and styrene
US5068982A (en)	1991-12-03	Rubber boot containing heat reflecting means
US2895937A (en)	1959-07-21	Process for heat treating butyl rubber with an aromatic nitroso compound and product obtained
US2497458A (en)	1950-02-14	Butadiene-styrene copolymer tackified with isoolefin-diolefin-styrene copolymer
KR20050030952A (ko)	2005-03-31	수소화 중합체의 제조 방법
US5148565A (en)	1992-09-22	Method for making a rubber boot containing heat reflecting means
US3868344A (en)	1975-02-25	Oil extended molecular weight controlled alfin gums