CS272793B2 - Method of rubber vulcanization - Google Patents

Method of rubber vulcanization Download PDF

Info

Publication number: CS272793B2
Authority: CS; Czechoslovakia
Prior art keywords: weight; parts; sulfur; benzothiazyl; alkyl
Prior art date: 1987-07-29

Application number

CS532988A

Other languages

Czech (cs)

English (en)

Other versions

CS532988A2 (en

Inventor

Rudiger Dr Schubart

Ulrich Dr Eholzer

Theo Dr Kempermann

Original Assignee

Bayer Ag

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.)

1987-07-29

Filing date

1988-07-27

Publication date

1991-02-12

1987-07-29 Priority claimed from DE19873725039 external-priority patent/DE3725039A1/de

1987-07-29 Priority claimed from DE19873725041 external-priority patent/DE3725041A1/de

1988-07-27 Application filed by Bayer Ag filed Critical Bayer Ag

1990-05-14 Publication of CS532988A2 publication Critical patent/CS532988A2/cs

1991-02-12 Publication of CS272793B2 publication Critical patent/CS272793B2/cs

Links

238000000034 method Methods 0.000 title claims description 11
238000013040 rubber vulcanization Methods 0.000 title 1
238000004073 vulcanization Methods 0.000 claims abstract description 49
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 41
229920001971 elastomer Polymers 0.000 claims abstract description 38
239000005060 rubber Substances 0.000 claims abstract description 38
LOVVSIULYJABJF-UHFFFAOYSA-N s-(2-nitrophenyl)thiohydroxylamine Chemical compound NSC1=CC=CC=C1[N+]([O-])=O LOVVSIULYJABJF-UHFFFAOYSA-N 0.000 claims abstract description 15
239000011593 sulfur Substances 0.000 claims description 38
229910052717 sulfur Inorganic materials 0.000 claims description 38
150000001875 compounds Chemical class 0.000 claims description 12
QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical compound [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 claims description 11
DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-UHFFFAOYSA-N 0.000 claims description 7
125000004953 trihalomethyl group Chemical group 0.000 claims description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
239000000126 substance Substances 0.000 claims description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
125000002947 alkylene group Chemical group 0.000 claims description 3
125000000732 arylene group Chemical group 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
125000002993 cycloalkylene group Chemical group 0.000 claims 2
125000006713 (C5-C10) cycloalkyl group Chemical group 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
GPNLWUFFWOYKLP-UHFFFAOYSA-N s-(1,3-benzothiazol-2-yl)thiohydroxylamine Chemical compound C1=CC=C2SC(SN)=NC2=C1 GPNLWUFFWOYKLP-UHFFFAOYSA-N 0.000 claims 1
239000005864 Sulphur Substances 0.000 abstract 3
-1 o-methylphenyl Chemical group 0.000 description 10
239000000203 mixture Substances 0.000 description 9
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
UQEDSBAKCOMAEH-UHFFFAOYSA-N n-tert-butylsulfanyl-2-nitroaniline Chemical compound CC(C)(C)SNC1=CC=CC=C1[N+]([O-])=O UQEDSBAKCOMAEH-UHFFFAOYSA-N 0.000 description 8
150000001412 amines Chemical class 0.000 description 7
238000004132 cross linking Methods 0.000 description 7
238000010438 heat treatment Methods 0.000 description 7
239000000047 product Substances 0.000 description 6
239000000243 solution Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
239000012071 phase Substances 0.000 description 4
FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 4
244000043261 Hevea brasiliensis Species 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
239000006229 carbon black Substances 0.000 description 3
229920003052 natural elastomer Polymers 0.000 description 3
229920001194 natural rubber Polymers 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 3
235000012239 silicon dioxide Nutrition 0.000 description 3
229920003051 synthetic elastomer Polymers 0.000 description 3
ZNCAMSISVWKWHL-UHFFFAOYSA-L zinc;butoxy-butylsulfanyl-oxido-sulfanylidene-$l^{5}-phosphane Chemical compound [Zn+2].CCCCOP([O-])(=S)SCCCC.CCCCOP([O-])(=S)SCCCC ZNCAMSISVWKWHL-UHFFFAOYSA-L 0.000 description 3
NTNKNFHIAFDCSJ-UHFFFAOYSA-N (2-nitrophenyl) thiohypochlorite Chemical compound [O-][N+](=O)C1=CC=CC=C1SCl NTNKNFHIAFDCSJ-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
235000021355 Stearic acid Nutrition 0.000 description 2
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
238000005299 abrasion Methods 0.000 description 2
239000012190 activator Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000001816 cooling Methods 0.000 description 2
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 2
150000004985 diamines Chemical class 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
239000000945 filler Substances 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
CMAUJSNXENPPOF-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)-n-cyclohexylcyclohexanamine Chemical compound C1CCCCC1N(C1CCCCC1)SC1=NC2=CC=CC=C2S1 CMAUJSNXENPPOF-UHFFFAOYSA-N 0.000 description 2
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000008117 stearic acid Substances 0.000 description 2
238000010059 sulfur vulcanization Methods 0.000 description 2
239000005061 synthetic rubber Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 2
229960002447 thiram Drugs 0.000 description 2
239000001993 wax Substances 0.000 description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 1
125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
LGBYJXBCVZKJBL-UHFFFAOYSA-N 1-[(2-oxoazepan-1-yl)disulfanyl]azepan-2-one Chemical compound O=C1CCCCCN1SSN1C(=O)CCCCC1 LGBYJXBCVZKJBL-UHFFFAOYSA-N 0.000 description 1
YZMJORJFRMKMFK-UHFFFAOYSA-N 2-methyl-n-(2-nitrophenyl)sulfanylpropan-2-amine Chemical compound CC(C)(C)NSC1=CC=CC=C1[N+]([O-])=O YZMJORJFRMKMFK-UHFFFAOYSA-N 0.000 description 1
QRYFCNPYGUORTK-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-yldisulfanyl)morpholine Chemical compound C1COCCN1SSC1=NC2=CC=CC=C2S1 QRYFCNPYGUORTK-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
239000004604 Blowing Agent Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
239000004338 Dichlorodifluoromethane Substances 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
239000004594 Masterbatch (MB) Substances 0.000 description 1
229920000459 Nitrile rubber Polymers 0.000 description 1
239000005062 Polybutadiene Substances 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
229910000272 alkali metal oxide Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
230000003712 anti-aging effect Effects 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000002585 base Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
230000006835 compression Effects 0.000 description 1
238000007906 compression Methods 0.000 description 1
AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
229920003244 diene elastomer Polymers 0.000 description 1
239000012990 dithiocarbamate Substances 0.000 description 1
150000004659 dithiocarbamates Chemical class 0.000 description 1
239000000975 dye Substances 0.000 description 1
239000003974 emollient agent Substances 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
230000002209 hydrophobic effect Effects 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000004898 kneading Methods 0.000 description 1
239000012263 liquid product Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
ILSQBBRAYMWZLQ-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)-n-propan-2-ylpropan-2-amine Chemical compound C1=CC=C2SC(SN(C(C)C)C(C)C)=NC2=C1 ILSQBBRAYMWZLQ-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
UWAAYUHNBNVRRL-UHFFFAOYSA-N n-phenylsulfanylnitramide Chemical class [O-][N+](=O)NSC1=CC=CC=C1 UWAAYUHNBNVRRL-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000049 pigment Substances 0.000 description 1
229920002857 polybutadiene Polymers 0.000 description 1
229920001195 polyisoprene Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000011814 protection agent Substances 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
ZLIOIJSVMSHZQQ-UHFFFAOYSA-N s-cyclohexylthiohydroxylamine Chemical compound NSC1CCCCC1 ZLIOIJSVMSHZQQ-UHFFFAOYSA-N 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229920003048 styrene butadiene rubber Polymers 0.000 description 1
125000001424 substituent group Chemical group 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
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000010998 test method Methods 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
150000003751 zinc Chemical class 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
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/43—Compounds containing sulfur bound to nitrogen
- C08K5/44—Sulfenamides

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Compositions Of Macromolecular Compounds (AREA)
Processes Of Treating Macromolecular Substances (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CS532988A 1987-07-29 1988-07-27 Method of rubber vulcanization CS272793B2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19873725039 DE3725039A1 (de)	1987-07-29	1987-07-29	Verfahren zur herstellung von 2-nitrophenylsulfenamiden und 2-nitrophenylsulfenamide
DE19873725041 DE3725041A1 (de)	1987-07-29	1987-07-29	Reversionsschutzmittel

Publications (2)

Publication Number	Publication Date
CS532988A2 CS532988A2 (en)	1990-05-14
CS272793B2 true CS272793B2 (en)	1991-02-12

Family

ID=25858045

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS532988A CS272793B2 (en)	1987-07-29	1988-07-27	Method of rubber vulcanization

Country Status (4)

Country	Link
EP (1)	EP0301376A1 (ja)
JP (1)	JPS6448831A (ja)
BR (1)	BR8803751A (ja)
CS (1)	CS272793B2 (ja)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE4036420A1 (de) *	1989-11-18	1991-05-23	Phoenix Ag	Nicht-nitrosamintoxische vulkanisate fuer setzungsarme gummiqualitaeten
JP2013194065A (ja) *	2012-03-16	2013-09-30	Sanshin Chem Ind Co Ltd	ゴム組成物
CN112645900B (zh) *	2020-12-25	2023-03-17	科迈化工股份有限公司	促进剂dcbs的合成方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2460393A (en) *	1945-06-23	1949-02-01	Us Rubber Co	Vulcanization of rubber
DE2918469C3 (de) *	1979-05-08	1982-05-13	Bayer Ag, 5090 Leverkusen	Vulkanisationssystem und dessen Verwendung zur Vulkanisation von Natur- und/oder Synthesekautschuk

1988
- 1988-07-19 EP EP88111580A patent/EP0301376A1/de not_active Withdrawn
- 1988-07-22 JP JP18196788A patent/JPS6448831A/ja active Pending
- 1988-07-27 CS CS532988A patent/CS272793B2/cs unknown
- 1988-07-28 BR BR8803751A patent/BR8803751A/pt unknown

Also Published As

Publication number	Publication date
CS532988A2 (en)	1990-05-14
BR8803751A (pt)	1989-02-14
JPS6448831A (en)	1989-02-23
EP0301376A1 (de)	1989-02-01

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RU2067974C1 (ru)	1996-10-20	Сульфидсодержащие полицитраконимиды и полиитаконимиды
US5130363A (en)	1992-07-14	Rubber vulcanizates having improved hysteresis behavior
US3828002A (en)	1974-08-06	Rubber stabilized with phenylene-diamine-s-triazines
US4621121A (en)	1986-11-04	Vulcanizable mixture containing bis-(2-ethylamino-s-triazin-6-yl)-tetrasulfide
US2321305A (en)	1943-06-08	Accelerator of vulcanization
US2370253A (en)	1945-02-27	Arylene thiazyl sulphenamides
WO1995030665A1 (en)	1995-11-16	Novel sulfenamide accelerators and rubber compositions containing the same
CS272793B2 (en)	1991-02-12	Method of rubber vulcanization
KR930010781B1 (ko)	1993-11-11	가황 촉진 방법
US6646029B1 (en)	2003-11-11	Pyrimidine derivatives as hardness stabilizers
US2343538A (en)	1944-03-07	Thiazyl sulphamine derivative
US3839303A (en)	1974-10-01	Inhibiting premature vulcanization with aminothiopyrimidines
JP3538213B2 (ja)	2004-06-14	ポリスルフィド化合物、ジエン系ゴムの加硫法、加硫系及びジエン系加硫ゴム製造方法
KR20010045644A (ko)	2001-06-05	타이어용 고무조성물
CZ9300779A3 (en)	1994-02-16	Polycitraconimides and polyitacomides containing (poly)-sulfide groups
US4873291A (en)	1989-10-10	Rubber vulcanization system with triazine compounds
US3770707A (en)	1973-11-06	Nitrobenzothiazole alkyl or cycloalkyl disulfides
US4673741A (en)	1987-06-16	Bis-(2-ethylamino-4-diethylamino-s-triazine-6-yl) tetrasulfide, process for its production, use and vulcanizable mixtures containing it
US3634318A (en)	1972-01-11	Rubber formulations comprising phenylenediamines and n-aryl sulfenamides
US2930824A (en)	1960-03-29	Certain n, n'-disubstituted ethylenebisbenzothiazolesulfenamides
US2173732A (en)	1939-09-19	Accelerator of vulcanization
US3689467A (en)	1972-09-05	Benzothiazole sulfenamides
US2809202A (en)	1957-10-08	N-cyanoethyl benzothiazole sulfenamides
US4755320A (en)	1988-07-05	Rubber vulcanization system
JPH0499762A (ja)	1992-03-31	芳香族ジチオカルボン酸のスルフアイド誘導体、その製法及びこれより成る天然−及び合成ゴム用の架橋剤