SU856390A3 - Резинова смесь на основе натурального каучука или сочетани бутадиенового и бутадиенстирольного каучуков - Google Patents

Резинова смесь на основе натурального каучука или сочетани бутадиенового и бутадиенстирольного каучуков Download PDF

Info

Publication number: SU856390A3
Authority: SU; USSR - Soviet Union
Prior art keywords: bis; ester; acid; phenylene; cyclohexylthio
Prior art date: 1978-07-31

Application number

SU792790755A

Other languages

English (en)

Russian (ru)

Inventor

Морита Эиихи

Original Assignee

Монсанто Компани (Фирма)

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.)

1978-07-31

Filing date

1979-07-30

Publication date

1981-08-15

1979-07-30 Application filed by Монсанто Компани (Фирма) filed Critical Монсанто Компани (Фирма)

1981-08-15 Application granted granted Critical

1981-08-15 Publication of SU856390A3 publication Critical patent/SU856390A3/ru

Links

239000000203 mixture Substances 0.000 title claims description 20
229920001971 elastomer Polymers 0.000 title claims description 16
239000005060 rubber Substances 0.000 title claims description 16
244000043261 Hevea brasiliensis Species 0.000 title claims description 10
229920003052 natural elastomer Polymers 0.000 title claims description 10
229920001194 natural rubber Polymers 0.000 title claims description 10
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 title claims description 6
MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 title 1
-1 carbamic acid diester Chemical class 0.000 claims description 61
239000002253 acid Substances 0.000 claims description 20
OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 claims description 11
230000002028 premature Effects 0.000 claims description 11
229910052717 sulfur Inorganic materials 0.000 claims description 11
238000004073 vulcanization Methods 0.000 claims description 11
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
239000003112 inhibitor Substances 0.000 claims description 10
239000011593 sulfur Substances 0.000 claims description 10
239000004305 biphenyl Substances 0.000 claims description 9
150000002148 esters Chemical class 0.000 claims description 9
235000010290 biphenyl Nutrition 0.000 claims description 8
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 5
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 4
239000006229 carbon black Substances 0.000 claims description 4
229920003048 styrene butadiene rubber Polymers 0.000 claims description 4
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 3
235000021355 Stearic acid Nutrition 0.000 claims description 3
GIFFWPXVAWPEIV-UHFFFAOYSA-N [2,3-bis(phenylsulfanyl)phenyl]carbamic acid Chemical compound C=1C=CC=CC=1SC=1C(NC(=O)O)=CC=CC=1SC1=CC=CC=C1 GIFFWPXVAWPEIV-UHFFFAOYSA-N 0.000 claims description 3
KKBFCANXQUNJBO-UHFFFAOYSA-N [2,3-bis(propan-2-ylsulfanyl)phenyl]carbamic acid Chemical compound CC(C)SC1=CC=CC(NC(O)=O)=C1SC(C)C KKBFCANXQUNJBO-UHFFFAOYSA-N 0.000 claims description 3
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 3
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 3
229920002857 polybutadiene Polymers 0.000 claims description 3
239000008117 stearic acid Substances 0.000 claims description 3
ABUTWWREKHJQTP-UHFFFAOYSA-N 1-methyl-2,4-bis(phenylsulfanyl)benzene Chemical compound C1(=CC=CC=C1)SC1=C(C=CC(=C1)SC1=CC=CC=C1)C ABUTWWREKHJQTP-UHFFFAOYSA-N 0.000 claims description 2
KGBBDBRJXGILTQ-UHFFFAOYSA-N [3-(2-methylprop-2-enoyloxy)-2,2-bis(2-methylprop-2-enoyloxymethyl)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(COC(=O)C(C)=C)(COC(=O)C(C)=C)COC(=O)C(C)=C KGBBDBRJXGILTQ-UHFFFAOYSA-N 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
239000011787 zinc oxide Substances 0.000 claims description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
AMNPXXIGUOKIPP-UHFFFAOYSA-N [4-(carbamothioylamino)phenyl]thiourea Chemical compound NC(=S)NC1=CC=C(NC(N)=S)C=C1 AMNPXXIGUOKIPP-UHFFFAOYSA-N 0.000 claims 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
239000001569 carbon dioxide Substances 0.000 claims 1
229910002092 carbon dioxide Inorganic materials 0.000 claims 1
239000003921 oil Substances 0.000 claims 1
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 1
239000011701 zinc Substances 0.000 claims 1
229910052725 zinc Inorganic materials 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
239000007787 solid Substances 0.000 description 7
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
230000002401 inhibitory effect Effects 0.000 description 5
239000010802 sludge Substances 0.000 description 5
150000007513 acids Chemical class 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000009864 tensile test Methods 0.000 description 4
238000005292 vacuum distillation Methods 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
XYLDATQNXLXWDJ-UHFFFAOYSA-N [2,3-bis(cyclohexylsulfanyl)phenyl]carbamic acid Chemical compound C1CCCCC1SC=1C(NC(=O)O)=CC=CC=1SC1CCCCC1 XYLDATQNXLXWDJ-UHFFFAOYSA-N 0.000 description 3
239000012043 crude product Substances 0.000 description 3
238000004811 liquid chromatography Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000000047 product Substances 0.000 description 3
239000011347 resin Substances 0.000 description 3
229920005989 resin Polymers 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
229920003051 synthetic elastomer Polymers 0.000 description 3
239000005061 synthetic rubber Substances 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
238000000034 method Methods 0.000 description 2
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 2
CMRIDRQURQKEJY-UHFFFAOYSA-N phenyl(phenylsulfanyl)carbamic acid Chemical compound C=1C=CC=CC=1N(C(=O)O)SC1=CC=CC=C1 CMRIDRQURQKEJY-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000002002 slurry Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 1
DKUMRTLIWHSMAU-UHFFFAOYSA-N 1,4-bis(cyclohexylsulfanyl)benzene Chemical compound C1(CCCCC1)SC1=CC=C(C=C1)SC1CCCCC1 DKUMRTLIWHSMAU-UHFFFAOYSA-N 0.000 description 1
125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
LWGRPXZKPVYNBS-UHFFFAOYSA-N 2-chlorosulfanylethyl thiohypochlorite Chemical compound ClSCCSCl LWGRPXZKPVYNBS-UHFFFAOYSA-N 0.000 description 1
ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical compound C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 description 1
ZZMVLMVFYMGSMY-UHFFFAOYSA-N 4-n-(4-methylpentan-2-yl)-1-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(NC(C)CC(C)C)=CC=C1NC1=CC=CC=C1 ZZMVLMVFYMGSMY-UHFFFAOYSA-N 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
239000004594 Masterbatch (MB) Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
PPQCOLWFUAINDS-UHFFFAOYSA-N [3-(carboxyamino)-4-methylphenyl]carbamic acid Chemical compound CC1=CC=C(NC(O)=O)C=C1NC(O)=O PPQCOLWFUAINDS-UHFFFAOYSA-N 0.000 description 1
238000007605 air drying Methods 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
XRFDWTWFFLOKAV-UHFFFAOYSA-N cyclohexyl thiohypochlorite Chemical compound ClSC1CCCCC1 XRFDWTWFFLOKAV-UHFFFAOYSA-N 0.000 description 1
QKQDGSIGIPUNJB-UHFFFAOYSA-N cyclohexylsulfanyl(phenyl)carbamic acid Chemical compound C=1C=CC=CC=1N(C(=O)O)SC1CCCCC1 QKQDGSIGIPUNJB-UHFFFAOYSA-N 0.000 description 1
LUAGRBPFVZNFMA-UHFFFAOYSA-N cyclohexylsulfanylcarbamic acid Chemical compound OC(=O)NSC1CCCCC1 LUAGRBPFVZNFMA-UHFFFAOYSA-N 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000011049 filling Methods 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
210000002837 heart atrium Anatomy 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
230000003993 interaction Effects 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
RMVRSNDYEFQCLF-UHFFFAOYSA-N phenyl mercaptan Natural products SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 1
PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical compound OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000000126 substance Substances 0.000 description 1
229910021653 sulphate ion Inorganic materials 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
ZUBNXRHITOZMOO-UHFFFAOYSA-N zinc;octadecanoic acid;oxygen(2-) Chemical compound [O-2].[Zn+2].CCCCCCCCCCCCCCCCCC(O)=O ZUBNXRHITOZMOO-UHFFFAOYSA-N 0.000 description 1

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Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Compositions Of Macromolecular Compounds (AREA)

SU792790755A 1978-07-31 1979-07-30 Резинова смесь на основе натурального каучука или сочетани бутадиенового и бутадиенстирольного каучуков SU856390A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US92962178A	1978-07-31	1978-07-31

Publications (1)

Publication Number	Publication Date
SU856390A3 true SU856390A3 (ru)	1981-08-15

Family

ID=25458173

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU792790755A SU856390A3 (ru)	1978-07-31	1979-07-30	Резинова смесь на основе натурального каучука или сочетани бутадиенового и бутадиенстирольного каучуков

Country Status (2)

Country	Link
JP (1)	JPS5521498A (2)
SU (1)	SU856390A3 (2)

1979
- 1979-07-30 SU SU792790755A patent/SU856390A3/ru active
- 1979-07-30 JP JP9804979A patent/JPS5521498A/ja active Granted

Also Published As

Publication number	Publication date
JPS6337785B2 (2)	1988-07-27
JPS5521498A (en)	1980-02-15

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DE69525763T2 (de)	2002-10-02	4,6-DI-t-BUTYL-2,3-DIHYDROBENZOTHIOPHENE, DIE LDL OXIDATION HEMMEN
Soper et al.	1948	Biosynthesis of penicillins. VII. 1 Oxy-and mercaptoacetic acids
SU856390A3 (ru)	1981-08-15	Резинова смесь на основе натурального каучука или сочетани бутадиенового и бутадиенстирольного каучуков
US3927091A (en)	1975-12-16	Carboxylic acid amides
DE2337642B2 (de)	1979-02-08	Phosphorsäureamide und ihre Verwendung bei der Vulkanisation von Kautschuk k
DE2403208C2 (de)	1982-08-05	Thiophosphorsäureamide, Verfahren zu ihrer Herstellung und ihre Verwendung
DE2732994C2 (de)	1995-09-07	Verwendung von N-Sulfonylsulfiliminen und N-Sulfonylsulfilimine als solche
US4271050A (en)	1981-06-02	Vulcanizable rubber compositions inhibited from premature vulcanization by methylene thioethers
US4111933A (en)	1978-09-05	Protection of functional groups during reaction and their subsequent restoration
US4342705A (en)	1982-08-03	Methylene thioethers
EP0007806B1 (en)	1981-08-26	N-sulfenyl derivatives of di(carbamic acid esters) and vulcanizable rubber compositions containing them
US4156680A (en)	1979-05-29	Scorch inhibited vulcanizable rubber compositions containing carbamic acid esters
EP0008177B1 (en)	1981-08-26	Vulcanizable rubber compositions containing substituted carbamic acid esters
US3725361A (en)	1973-04-03	Inhibiting premature vulcanization of rubber with n-thiohydrazodicarboxylate
CA1118782A (en)	1982-02-23	Scorch inhibited vulcanizable rubber compositions
EP0590457A1 (de)	1994-04-06	Benzothiazole-Derivate, zur Einführung von polaren Substituenten geeigneter Vulkanisationsbeschleuniger
US4291141A (en)	1981-09-22	Vulcanizable rubber compositions containing N-(sulfenyl) methacrylamides as scorch inhibitors
US4488985A (en)	1984-12-18	Phosphoramidates containing a p-phenylenediamine group
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
EP0035472A1 (de)	1981-09-09	Mercaptophenole und ihre Verwendung als Stabilisatoren
JP2000239287A (ja)	2000-09-05	ジチオリン酸ポリスルフィド混合物の製造方法
DE4233350A1 (de)	1994-04-07	Verwendung von Thioalkandionen als Aromastoffe
US4311647A (en)	1982-01-19	Process for preparation of (hydrocarbonthio)oxamides
US4311648A (en)	1982-01-19	N-(Sulfenyl) methacrylamides
US4311813A (en)	1982-01-19	N-(α-Alkylbenzylthio)succinimide