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 PDFInfo
- Publication number
- SU856390A3 SU856390A3 SU792790755A SU2790755A SU856390A3 SU 856390 A3 SU856390 A3 SU 856390A3 SU 792790755 A SU792790755 A SU 792790755A SU 2790755 A SU2790755 A SU 2790755A SU 856390 A3 SU856390 A3 SU 856390A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- bis
- ester
- acid
- phenylene
- cyclohexylthio
- Prior art date
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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
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 (enExample) |
| SU (1) | SU856390A3 (enExample) |
-
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 |
|---|---|
| JPS5521498A (en) | 1980-02-15 |
| JPS6337785B2 (enExample) | 1988-07-27 |
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