CA1105918A - Rubber accelerators - Google Patents

Rubber accelerators

Info

Publication number: CA1105918A
Authority: CA; Canada
Prior art keywords: composition according; benzothiazole sulfenamide; oxirane; dimorpholine; benzothiazole
Prior art date: 1977-07-11
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

Application number

CA304,852A

Other languages

English (en)

French (fr)

Inventor

Curtis A. Franz

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.)

Wyeth Holdings LLC

Original Assignee

American Cyanamid 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.)

1977-07-11

Filing date

1978-06-06

Publication date

1981-07-28

1977-07-11 Priority claimed from US05/814,603 external-priority patent/US4129452A/en

1977-07-11 Priority claimed from US05/814,601 external-priority patent/US4160741A/en

1978-06-06 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1981-07-28 Application granted granted Critical

1981-07-28 Publication of CA1105918A publication Critical patent/CA1105918A/en

Status Expired legal-status Critical Current

Links

229920001971 elastomer Polymers 0.000 title claims abstract description 12
239000005060 rubber Substances 0.000 title claims abstract description 12
239000000203 mixture Substances 0.000 claims description 17
229910052757 nitrogen Inorganic materials 0.000 claims description 13
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 13
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 12
-1 inclusive Chemical group 0.000 claims description 11
239000000944 linseed oil Substances 0.000 claims description 7
235000021388 linseed oil Nutrition 0.000 claims description 7
VIHMZNMSEVOOPY-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)propan-2-amine Chemical compound C1=CC=C2SC(SNC(C)C)=NC2=C1 VIHMZNMSEVOOPY-UHFFFAOYSA-N 0.000 claims description 7
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
GPNLWUFFWOYKLP-UHFFFAOYSA-N s-(1,3-benzothiazol-2-yl)thiohydroxylamine Chemical compound C1=CC=C2SC(SN)=NC2=C1 GPNLWUFFWOYKLP-UHFFFAOYSA-N 0.000 claims description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
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 claims description 4
125000000524 functional group Chemical group 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-UHFFFAOYSA-N 0.000 claims description 3
230000000087 stabilizing effect Effects 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
230000002452 interceptive effect Effects 0.000 claims description 2
239000003921 oil Substances 0.000 claims description 2
235000019198 oils Nutrition 0.000 claims description 2
244000068988 Glycine max Species 0.000 claims 1
235000010469 Glycine max Nutrition 0.000 claims 1
150000007942 carboxylates Chemical class 0.000 claims 1
239000003381 stabilizer Substances 0.000 abstract description 8
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 abstract description 8
150000002924 oxiranes Chemical class 0.000 abstract description 5
150000001875 compounds Chemical class 0.000 description 17
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 12
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 10
238000000034 method Methods 0.000 description 10
238000003860 storage Methods 0.000 description 8
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
230000006866 deterioration Effects 0.000 description 6
230000006641 stabilisation Effects 0.000 description 6
238000011105 stabilization Methods 0.000 description 6
239000004593 Epoxy Substances 0.000 description 4
241001441571 Hiodontidae Species 0.000 description 4
239000004594 Masterbatch (MB) Substances 0.000 description 4
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
238000004073 vulcanization Methods 0.000 description 4
ILNGCUVXLQVDTC-UHFFFAOYSA-N 4-chloromorpholine Chemical compound ClN1CCOCC1 ILNGCUVXLQVDTC-UHFFFAOYSA-N 0.000 description 3
OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 3
INWSRBSRCOKSEC-UHFFFAOYSA-N 2-(propoxymethyl)-3-propyloxirane Chemical compound C(CC)OCC1C(CCC)O1 INWSRBSRCOKSEC-UHFFFAOYSA-N 0.000 description 2
QRYFCNPYGUORTK-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-yldisulfanyl)morpholine Chemical compound C1COCCN1SSC1=NC2=CC=CC=C2S1 QRYFCNPYGUORTK-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
239000005062 Polybutadiene Substances 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
230000032683 aging Effects 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
150000001993 dienes Chemical class 0.000 description 2
230000000694 effects Effects 0.000 description 2
SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
238000010348 incorporation Methods 0.000 description 2
230000014759 maintenance of location Effects 0.000 description 2
XKIDASBNXGXGLR-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)-2,4,4-trimethylpentan-2-amine Chemical compound C1=CC=C2SC(SNC(C)(C)CC(C)(C)C)=NC2=C1 XKIDASBNXGXGLR-UHFFFAOYSA-N 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
DJKPPZYJVJJTJO-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)-n-cyclopentylcyclopentanamine Chemical compound C1CCCC1N(C1CCCC1)SC1=NC2=CC=CC=C2S1 DJKPPZYJVJJTJO-UHFFFAOYSA-N 0.000 description 2
CMNFWIMUALZCNG-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)-n-ethylethanamine Chemical compound C1=CC=C2SC(SN(CC)CC)=NC2=C1 CMNFWIMUALZCNG-UHFFFAOYSA-N 0.000 description 2
UZBIEGBACHITGH-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)methanamine Chemical compound C1=CC=C2SC(SNC)=NC2=C1 UZBIEGBACHITGH-UHFFFAOYSA-N 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
229920002857 polybutadiene Polymers 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000003549 soybean oil Substances 0.000 description 2
235000012424 soybean oil Nutrition 0.000 description 2
238000012360 testing method Methods 0.000 description 2
MQCPOLNSJCWPGT-UHFFFAOYSA-N 2,2'-Bisphenol F Chemical compound OC1=CC=CC=C1CC1=CC=CC=C1O MQCPOLNSJCWPGT-UHFFFAOYSA-N 0.000 description 1
MQXNNWDXHFBFEB-UHFFFAOYSA-N 2,2-bis(2-hydroxyphenyl)propane Chemical compound C=1C=CC=C(O)C=1C(C)(C)C1=CC=CC=C1O MQXNNWDXHFBFEB-UHFFFAOYSA-N 0.000 description 1
PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical compound CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 description 1
VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-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
NHJIDZUQMHKGRE-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-yl 2-(7-oxabicyclo[4.1.0]heptan-4-yl)acetate Chemical compound C1CC2OC2CC1OC(=O)CC1CC2OC2CC1 NHJIDZUQMHKGRE-UHFFFAOYSA-N 0.000 description 1
YXALYBMHAYZKAP-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1CC2OC2CC1C(=O)OCC1CC2OC2CC1 YXALYBMHAYZKAP-UHFFFAOYSA-N 0.000 description 1
229930185605 Bisphenol Natural products 0.000 description 1
NJIVFJXLMDTJCA-UHFFFAOYSA-N C1(=CC=C(C=C1)N)N.[S] Chemical compound C1(=CC=C(C=C1)N)N.[S] NJIVFJXLMDTJCA-UHFFFAOYSA-N 0.000 description 1
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical class S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
DKNPRRRKHAEUMW-UHFFFAOYSA-N Iodine aqueous Chemical compound [K+].I[I-]I DKNPRRRKHAEUMW-UHFFFAOYSA-N 0.000 description 1
239000005708 Sodium hypochlorite Substances 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
230000004075 alteration Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000010692 aromatic oil Substances 0.000 description 1
239000006229 carbon black Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000013329 compounding Methods 0.000 description 1
125000002993 cycloalkylene group Chemical group 0.000 description 1
ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
238000011161 development Methods 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
150000002118 epoxides Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000000835 fiber Substances 0.000 description 1
230000006698 induction Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
IUJLOAKJZQBENM-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)-2-methylpropan-2-amine Chemical compound C1=CC=C2SC(SNC(C)(C)C)=NC2=C1 IUJLOAKJZQBENM-UHFFFAOYSA-N 0.000 description 1
229940032017 n-oxydiethylene-2-benzothiazole sulfenamide Drugs 0.000 description 1
125000004433 nitrogen atom Chemical group N* 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
125000000466 oxiranyl group Chemical group 0.000 description 1
229920001568 phenolic resin Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000012545 processing Methods 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
230000000979 retarding effect Effects 0.000 description 1
238000010058 rubber compounding Methods 0.000 description 1
DIFCZTZSUFXWEJ-UHFFFAOYSA-N s-(4-butyl-1,3-benzothiazol-2-yl)thiohydroxylamine Chemical compound CCCCC1=CC=CC2=C1N=C(SN)S2 DIFCZTZSUFXWEJ-UHFFFAOYSA-N 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
229960005076 sodium hypochlorite Drugs 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
229920003048 styrene butadiene rubber Polymers 0.000 description 1
239000004636 vulcanized rubber 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
- 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
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1515—Three-membered rings
- 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
- C08K5/45—Heterocyclic compounds having sulfur in the ring
- C08K5/46—Heterocyclic compounds having sulfur in the ring with oxygen or nitrogen in the ring
- C08K5/47—Thiazoles

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)
Epoxy Resins (AREA)
Thiazole And Isothizaole Compounds (AREA)

CA304,852A 1977-07-11 1978-06-06 Rubber accelerators Expired CA1105918A (en)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US05/814,603 US4129452A (en)	1977-07-11	1977-07-11	Stabilization of N,N'-[(thiocarbonyl)thio]dimorpholine
US814,601		1977-07-11
US814,603		1977-07-11
US05/814,601 US4160741A (en)	1977-07-11	1977-07-11	Benzothiazole accelerators stabilized with oxirane compounds

Publications (1)

Publication Number	Publication Date
CA1105918A true CA1105918A (en)	1981-07-28

Family

ID=27123867

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA304,852A Expired CA1105918A (en)	1977-07-11	1978-06-06	Rubber accelerators

Country Status (11)

Country	Link
JP (1)	JPS5419975A (de)
AR (1)	AR219326A1 (de)
AU (1)	AU3658378A (de)
BR (1)	BR7804438A (de)
CA (1)	CA1105918A (de)
DD (1)	DD137236A5 (de)
DE (1)	DE2827933A1 (de)
FR (1)	FR2397435A1 (de)
GB (1)	GB1599357A (de)
PL (1)	PL208317A1 (de)
SE (1)	SE7807701L (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2161160B (en) *	1984-07-06	1989-05-24	Fisons Plc	Heterocyclic sulphinyl compounds
JP5632592B2 (ja) *	2008-08-19	2014-11-26	株式会社ブリヂストン	ゴム組成物

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3457218A (en) *	1965-05-28	1969-07-22	Bayer Ag	Cis-polybutadiene stabilized with an epoxide
US3658637A (en) *	1969-03-17	1972-04-25	Uniroyal Inc	Dialkyl oxalate stabilization of polyester fiber-rubber laminate against heat and chemical degradation
US3658743A (en) *	1970-04-30	1972-04-25	Uniroyal Inc	Stabilization of unsaturated hydrocarbon elastomers by synergistic combination of a phenolic compound an organic sulfide or thioester and an epoxide or phosphite ester

1978
- 1978-05-29 AU AU36583/78A patent/AU3658378A/en active Pending
- 1978-05-31 GB GB25188/78A patent/GB1599357A/en not_active Expired
- 1978-06-06 CA CA304,852A patent/CA1105918A/en not_active Expired
- 1978-06-07 AR AR272476A patent/AR219326A1/es active
- 1978-06-26 DE DE19782827933 patent/DE2827933A1/de not_active Withdrawn
- 1978-07-10 SE SE7807701A patent/SE7807701L/xx unknown
- 1978-07-10 BR BR7804438A patent/BR7804438A/pt unknown
- 1978-07-11 FR FR7820646A patent/FR2397435A1/fr active Pending
- 1978-07-11 DD DD78206653A patent/DD137236A5/de unknown
- 1978-07-11 JP JP8364778A patent/JPS5419975A/ja active Pending
- 1978-07-11 PL PL20831778A patent/PL208317A1/xx unknown

Also Published As

Publication number	Publication date
SE7807701L (sv)	1979-01-12
BR7804438A (pt)	1979-03-20
PL208317A1 (pl)	1979-07-02
JPS5419975A (en)	1979-02-15
GB1599357A (en)	1981-09-30
DE2827933A1 (de)	1979-01-25
AU3658378A (en)	1979-12-06
FR2397435A1 (fr)	1979-02-09
DD137236A5 (de)	1979-08-22
AR219326A1 (es)	1980-08-15

Legal Events

Date	Code	Title	Description
1998-07-28	MKEX	Expiry

Publication	Publication Date	Title
JPH0517705A (ja)	1993-01-26	充填剤の表面変性法、変性された充填剤及び加硫可能なゴム組成物
JPS6326140B2 (de)	1988-05-28
JPS5921344B2 (ja)	1984-05-19	ハロゲン含有ポリマ−の架橋
CA1266656A (en)	1990-03-13	Bis-(2-ethylamino-4-diethylamino-s-triazin-6-yl) tetrasulfide, process for production, use and containing vulcanisable mixtures
CA1105918A (en)	1981-07-28	Rubber accelerators
US4745147A (en)	1988-05-17	Vulcanizable chlorinated polyethylene compositions
US2731442A (en)	1956-01-17	Sulfur vulcanizable rubber stabilized with a mixture of an alkyl substituted phenol and an alkyl substituted di(hydroxyphenyl) alkane
US4129452A (en)	1978-12-12	Stabilization of N,N'-[(thiocarbonyl)thio]dimorpholine
JP3995346B2 (ja)	2007-10-24	薄板収納搬送容器用ポリカーボネート樹脂
CA1164119A (en)	1984-03-20	Viscosity-stabilized aqueous solutions
CA1314649C (en)	1993-03-16	Ultra violet light resistant carbonate polymers with improved processing stability
US4123411A (en)	1978-10-31	Plasticized composition of copolyetherester elastomer and aromatic sulfonamide
EP0057013A2 (de)	1982-08-04	Verwendung von Triorganophosphinen zur Steigerung der Wirkung von Alkoxysilanpolysulphiden als Kupplungsmittel"
US4160741A (en)	1979-07-10	Benzothiazole accelerators stabilized with oxirane compounds
US5102657A (en)	1992-04-07	Microbiocidal compositions
US4062797A (en)	1977-12-13	Stabilized accelerator compositions
EP0779331B1 (de)	2000-05-03	1,3,4-Thiadiazolether-Härtersysteme für chlorhaltige Polymere
AU623440B2 (en)	1992-05-14	Microbiocidal compositions
US4920165A (en)	1990-04-24	Scorch retarder for halogenated elastomers
CA1043927A (en)	1978-12-05	Low temperature plasticizer composition for natural and synthetic butadiene-styrene rubber
EP0602912B1 (de)	1998-06-10	Mischungen und Vulkanisiermittel für Kautschuk
US4116855A (en)	1978-09-26	Stabilized accelerator composition for rubber
JP2557680B2 (ja)	1996-11-27	硬化型組成物
US4101507A (en)	1978-07-18	Stabilization of polyphosphazenes
CA1072071A (en)	1980-02-19	Polysulphide rubbers