CS238650B2 - Composite formation containing sulphur-vulcanizable rubber mixture - Google Patents

Composite formation containing sulphur-vulcanizable rubber mixture Download PDF

Info

Publication number: CS238650B2
Authority: CS; Czechoslovakia
Prior art keywords: group; formula; rubber; integer; alkyl
Prior art date: 1982-10-21

Application number

CS837732A

Other languages

Czech (cs)

English (en)

Inventor

Jean-Marc Delseth

Daniel E Mauer

Philippe G Moniotte

Original Assignee

Monsanto Europe Sa

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.)

1982-10-21

Filing date

1983-10-20

Publication date

1985-12-16

1983-10-20 Application filed by Monsanto Europe Sa filed Critical Monsanto Europe Sa

1985-12-16 Publication of CS238650B2 publication Critical patent/CS238650B2/cs

Links

229920001971 elastomer Polymers 0.000 title claims abstract description 71
239000005060 rubber Substances 0.000 title claims abstract description 71
239000000203 mixture Substances 0.000 title claims description 34
239000002131 composite material Substances 0.000 title claims description 7
230000015572 biosynthetic process Effects 0.000 title description 7
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 55
229910052751 metal Inorganic materials 0.000 claims abstract description 32
239000002184 metal Substances 0.000 claims abstract description 32
239000011734 sodium Substances 0.000 claims abstract description 25
229910052708 sodium Inorganic materials 0.000 claims abstract description 23
229910052759 nickel Inorganic materials 0.000 claims abstract description 20
229910001369 Brass Inorganic materials 0.000 claims abstract description 19
239000010951 brass Substances 0.000 claims abstract description 19
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 claims abstract description 18
239000011701 zinc Substances 0.000 claims abstract description 16
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 15
229910017052 cobalt Inorganic materials 0.000 claims abstract description 15
239000010941 cobalt Substances 0.000 claims abstract description 15
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 15
229910052725 zinc Inorganic materials 0.000 claims abstract description 15
-1 2,5-dihydroxyphenyl Chemical group 0.000 claims description 69
150000001875 compounds Chemical class 0.000 claims description 51
239000002318 adhesion promoter Substances 0.000 claims description 45
125000000217 alkyl group Chemical group 0.000 claims description 33
125000004432 carbon atom Chemical group C* 0.000 claims description 31
229910052757 nitrogen Inorganic materials 0.000 claims description 24
125000002947 alkylene group Chemical group 0.000 claims description 18
229910052717 sulfur Inorganic materials 0.000 claims description 16
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 15
239000011593 sulfur Substances 0.000 claims description 15
125000001424 substituent group Chemical group 0.000 claims description 9
150000001768 cations Chemical class 0.000 claims description 8
239000011777 magnesium Substances 0.000 claims description 8
238000004073 vulcanization Methods 0.000 claims description 8
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 7
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 7
125000003342 alkenyl group Chemical group 0.000 claims description 7
229910052788 barium Inorganic materials 0.000 claims description 7
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 7
229910052791 calcium Inorganic materials 0.000 claims description 7
239000011575 calcium Substances 0.000 claims description 7
229910052749 magnesium Inorganic materials 0.000 claims description 7
125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 6
125000004965 chloroalkyl group Chemical group 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
125000004450 alkenylene group Chemical group 0.000 claims description 5
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 5
125000004957 naphthylene group Chemical group 0.000 claims description 4
125000004436 sodium atom Chemical group 0.000 claims description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
125000006734 (C2-C20) alkoxyalkyl group Chemical group 0.000 claims description 2
125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims description 2
125000005197 alkyl carbonyloxy alkyl group Chemical group 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
150000002500 ions Chemical class 0.000 abstract description 9
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract description 7
239000000126 substance Substances 0.000 abstract description 2
230000032683 aging Effects 0.000 description 36
150000003839 salts Chemical class 0.000 description 23
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 20
DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical group [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 18
238000012360 testing method Methods 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000002585 base Substances 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 13
229910052802 copper Inorganic materials 0.000 description 13
239000010949 copper Substances 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
150000001412 amines Chemical class 0.000 description 10
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 9
229920000642 polymer Polymers 0.000 description 9
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 8
229910052783 alkali metal Inorganic materials 0.000 description 8
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 8
GWIKYPMLNBTJHR-UHFFFAOYSA-M thiosulfonate group Chemical group S(=S)(=O)[O-] GWIKYPMLNBTJHR-UHFFFAOYSA-M 0.000 description 8
150000001869 cobalt compounds Chemical class 0.000 description 7
238000000034 method Methods 0.000 description 7
239000000047 product Substances 0.000 description 7
239000007787 solid Substances 0.000 description 7
229910000831 Steel Inorganic materials 0.000 description 6
150000001340 alkali metals Chemical class 0.000 description 6
238000010073 coating (rubber) Methods 0.000 description 6
239000011248 coating agent Substances 0.000 description 6
238000000576 coating method Methods 0.000 description 6
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
238000005755 formation reaction Methods 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
239000003921 oil Substances 0.000 description 6
239000010959 steel Substances 0.000 description 6
239000000654 additive Substances 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
239000006229 carbon black Substances 0.000 description 5
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 5
230000000694 effects Effects 0.000 description 5
125000000623 heterocyclic group Chemical group 0.000 description 5
GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 5
150000002816 nickel compounds Chemical class 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
235000021355 Stearic acid Nutrition 0.000 description 4
239000000853 adhesive Substances 0.000 description 4
230000001070 adhesive effect Effects 0.000 description 4
125000001931 aliphatic group Chemical group 0.000 description 4
125000005119 alkyl cycloalkyl group Chemical group 0.000 description 4
125000000753 cycloalkyl group Chemical group 0.000 description 4
OAUVKSCRGKIWSR-UHFFFAOYSA-L dioxido-oxo-sulfanylidene-$l^{6}-sulfane;nickel(2+) Chemical class [Ni+2].[O-]S([O-])(=O)=S OAUVKSCRGKIWSR-UHFFFAOYSA-L 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 4
125000000962 organic group Chemical group 0.000 description 4
229920001195 polyisoprene Polymers 0.000 description 4
150000003335 secondary amines Chemical class 0.000 description 4
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 4
239000000243 solution Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000008117 stearic acid Substances 0.000 description 4
239000011787 zinc oxide Substances 0.000 description 4
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
MHKLKWCYGIBEQF-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-ylsulfanyl)morpholine Chemical compound C1COCCN1SC1=NC2=CC=CC=C2S1 MHKLKWCYGIBEQF-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
229910021586 Nickel(II) chloride Inorganic materials 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
125000004448 alkyl carbonyl group Chemical group 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
239000004305 biphenyl Substances 0.000 description 3
235000010290 biphenyl Nutrition 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
238000006731 degradation reaction Methods 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
JOSJZPLSVYWPAG-UHFFFAOYSA-L dodecanoate;nickel(2+) Chemical compound [Ni+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O JOSJZPLSVYWPAG-UHFFFAOYSA-L 0.000 description 3
238000011156 evaluation Methods 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
150000004687 hexahydrates Chemical class 0.000 description 3
150000004677 hydrates Chemical class 0.000 description 3
230000006872 improvement Effects 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
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 3
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 3
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
125000003884 phenylalkyl group Chemical group 0.000 description 3
GPNLWUFFWOYKLP-UHFFFAOYSA-N s-(1,3-benzothiazol-2-yl)thiohydroxylamine Chemical class C1=CC=C2SC(SN)=NC2=C1 GPNLWUFFWOYKLP-UHFFFAOYSA-N 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
235000019345 sodium thiosulphate Nutrition 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
239000004636 vulcanized rubber Substances 0.000 description 3
ZRMMVODKVLXCBB-UHFFFAOYSA-N 1-n-cyclohexyl-4-n-phenylbenzene-1,4-diamine Chemical compound C1CCCCC1NC(C=C1)=CC=C1NC1=CC=CC=C1 ZRMMVODKVLXCBB-UHFFFAOYSA-N 0.000 description 2
ZNRLMGFXSPUZNR-UHFFFAOYSA-N 2,2,4-trimethyl-1h-quinoline Chemical compound C1=CC=C2C(C)=CC(C)(C)NC2=C1 ZNRLMGFXSPUZNR-UHFFFAOYSA-N 0.000 description 2
WRGWVXRANTWQOG-UHFFFAOYSA-N 2,4-diethyl-2-methyl-1h-quinoline Chemical compound C1=CC=C2C(CC)=CC(C)(CC)NC2=C1 WRGWVXRANTWQOG-UHFFFAOYSA-N 0.000 description 2
RCPUUVXIUIWMEE-UHFFFAOYSA-N 2-(2,4-dinitrophenyl)sulfanyl-1,3-benzothiazole Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC=C1SC1=NC2=CC=CC=C2S1 RCPUUVXIUIWMEE-UHFFFAOYSA-N 0.000 description 2
125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 description 2
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 2
PPLHJYOTUIILGX-UHFFFAOYSA-N 4-n-(5-methylheptan-3-yl)benzene-1,4-diamine Chemical compound CCC(C)CC(CC)NC1=CC=C(N)C=C1 PPLHJYOTUIILGX-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
244000043261 Hevea brasiliensis Species 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
229920001967 Metal rubber Polymers 0.000 description 2
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
230000002411 adverse Effects 0.000 description 2
125000002877 alkyl aryl group Chemical group 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
230000003078 antioxidant effect Effects 0.000 description 2
125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
125000003710 aryl alkyl group Chemical group 0.000 description 2
230000008901 benefit Effects 0.000 description 2
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
UCGFRIAOVLXVKL-UHFFFAOYSA-N benzylthiourea Chemical compound NC(=S)NCC1=CC=CC=C1 UCGFRIAOVLXVKL-UHFFFAOYSA-N 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
IEJSIQMFHIVOAR-UHFFFAOYSA-N butoxy-hydroxy-oxo-sulfanylidene-$l^{6}-sulfane Chemical compound CCCCOS(O)(=O)=S IEJSIQMFHIVOAR-UHFFFAOYSA-N 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
WUBUHPZTDFJNDA-UHFFFAOYSA-N ethoxy-hydroxy-oxo-sulfanylidene-$l^{6}-sulfane Chemical compound CCOS(O)(=O)=S WUBUHPZTDFJNDA-UHFFFAOYSA-N 0.000 description 2
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000009472 formulation Methods 0.000 description 2
ZRALSGWEFCBTJO-UHFFFAOYSA-O guanidinium Chemical compound NC(N)=[NH2+] ZRALSGWEFCBTJO-UHFFFAOYSA-O 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
XWEBSKRLUGLUTN-UHFFFAOYSA-N hydroxy-oxo-phenylmethoxy-sulfanylidene-$l^{6}-sulfane Chemical compound OS(=O)(=S)OCC1=CC=CC=C1 XWEBSKRLUGLUTN-UHFFFAOYSA-N 0.000 description 2
125000004464 hydroxyphenyl group Chemical group 0.000 description 2
125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
150000002541 isothioureas Chemical class 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000001624 naphthyl group Chemical group 0.000 description 2
229920003052 natural elastomer Polymers 0.000 description 2
229920001194 natural rubber Polymers 0.000 description 2
150000002815 nickel Chemical class 0.000 description 2
125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
230000000704 physical effect Effects 0.000 description 2
229920002857 polybutadiene Polymers 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
230000008569 process Effects 0.000 description 2
230000001737 promoting effect Effects 0.000 description 2
125000005493 quinolyl group Chemical group 0.000 description 2
230000002787 reinforcement Effects 0.000 description 2
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ZSGAVTXPNVXVNQ-UHFFFAOYSA-J dichloronickel Chemical compound Cl[Ni]Cl.Cl[Ni]Cl ZSGAVTXPNVXVNQ-UHFFFAOYSA-J 0.000 description 1
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KNWOCNXXNMLUQO-UHFFFAOYSA-N hydroxy-octadecoxy-oxo-sulfanylidene-lambda6-sulfane Chemical class CCCCCCCCCCCCCCCCCCOS(O)(=O)=S KNWOCNXXNMLUQO-UHFFFAOYSA-N 0.000 description 1
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DLSOILHAKCBARI-UHFFFAOYSA-N n-benzyl-2-methylpropan-2-amine Chemical compound CC(C)(C)NCC1=CC=CC=C1 DLSOILHAKCBARI-UHFFFAOYSA-N 0.000 description 1
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239000008239 natural water Substances 0.000 description 1
229910001453 nickel ion Inorganic materials 0.000 description 1
BMGNSKKZFQMGDH-FDGPNNRMSA-L nickel(2+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ni+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O BMGNSKKZFQMGDH-FDGPNNRMSA-L 0.000 description 1
JFPHVASUYUBBCP-UHFFFAOYSA-L nickel(2+);oxido-oxo-phenylmethoxy-sulfanylidene-$l^{6}-sulfane Chemical compound [Ni+2].[O-]S(=O)(=S)OCC1=CC=CC=C1.[O-]S(=O)(=S)OCC1=CC=CC=C1 JFPHVASUYUBBCP-UHFFFAOYSA-L 0.000 description 1
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125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
- C08J5/10—Reinforcing macromolecular compounds with loose or coherent fibrous material characterised by the additives used in the polymer mixture
- 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
- C08K5/41—Compounds containing sulfur bound to oxygen
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2321/00—Characterised by the use of unspecified rubbers
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31678—Of metal
- Y10T428/31681—Next to polyester, polyamide or polyimide [e.g., alkyd, glue, or nylon, etc.]
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31678—Of metal
- Y10T428/31707—Next to natural rubber
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31725—Of polyamide
- Y10T428/31765—Inorganic-containing or next to inorganic-containing

Landscapes

Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Organic Chemistry (AREA)
Polymers & Plastics (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Materials Engineering (AREA)
Manufacturing & Machinery (AREA)
Engineering & Computer Science (AREA)
Compositions Of Macromolecular Compounds (AREA)
Adhesives Or Adhesive Processes (AREA)
Laminated Bodies (AREA)
Gloves (AREA)

CS837732A 1982-10-21 1983-10-20 Composite formation containing sulphur-vulcanizable rubber mixture CS238650B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB8230136		1982-10-21

Publications (1)

Publication Number	Publication Date
CS238650B2 true CS238650B2 (en)	1985-12-16

Family

ID=10533766

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS837732A CS238650B2 (en)	1982-10-21	1983-10-20	Composite formation containing sulphur-vulcanizable rubber mixture

Country Status (14)

Country	Link
US (2)	US4532080A (de)
EP (1)	EP0109955B1 (de)
JP (1)	JPS5991140A (de)
AT (1)	ATE32084T1 (de)
AU (1)	AU565303B2 (de)
BR (1)	BR8305812A (de)
CA (1)	CA1268476C (de)
CS (1)	CS238650B2 (de)
DD (1)	DD210235A5 (de)
DE (1)	DE3375401D1 (de)
ES (1)	ES8600344A1 (de)
IE (1)	IE54615B1 (de)
SU (1)	SU1398777A3 (de)
ZA (1)	ZA837797B (de)

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US20030220427A1 (en) *	2002-05-09	2003-11-27	Gary Wentworth	Adhesion promoter for cord-reinforced rubber and metal or polymer substrate/rubber composites
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US8334340B2 (en) *	2008-10-30	2012-12-18	Momentive Performance Materials, Inc.	Sulfur-containing cycloaliphatic compound, process for its preparation, filled sulfur-vulcanizable elastomer composition containing same and articles fabricated therefrom
US8124206B2 (en) *	2008-10-30	2012-02-28	Momentive Performance Materials, Inc.	Sulfur-containing cycloaliphatic compound, filled sulfur-vulcanizable elastomer composition containing sulfur-containing cycloaliphatic compound and articles fabricated therefrom
US8470197B2 (en)	2008-10-30	2013-06-25	Momentive Performance Materials Inc.	Crosslinked polysulfide-containing cycloaliphatic compound, process for its preparation, filled sulfur-vulcanizable elastomer composition containing same and articles fabricated therefrom
JP5051274B2 (ja)	2009-06-04	2012-10-17	住友化学株式会社	加硫ゴムが有する粘弾性特性を改善させるためのｓ−（３−アミノプロピル）チオ硫酸および／またはその金属塩の使用
JP5589564B2 (ja) *	2009-06-30	2014-09-17	住友化学株式会社	加硫ゴム及びその製造方法
JP2012012458A (ja) *	2010-06-30	2012-01-19	Sumitomo Chemical Co Ltd	加硫ゴム組成物の製造方法
JP2012012456A (ja) *	2010-06-30	2012-01-19	Sumitomo Chemical Co Ltd	Ｓ−（３−アミノプロピル）チオ硫酸および／またはその金属塩の使用方法
CN103180377A (zh) *	2010-10-29	2013-06-26	住友化学株式会社	硫化橡胶组合物的制造方法
KR20140050617A (ko) *	2011-08-01	2014-04-29	스미또모 가가꾸 가부시키가이샤	가황 고무의 동배율 저하 방법
KR101440099B1 (ko)	2011-12-28	2014-09-17	한국타이어 주식회사	타이어 벨트토핑용 고무 조성물 및 이를 이용하여 제조한 타이어
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WO2020092052A1 (en)	2018-11-01	2020-05-07	Flexsys America L.P.	Triazinanes and methods of making them
US20220298123A1 (en) *	2019-08-29	2022-09-22	Flexsys America L.P.	Triazinane derivatives and methods of making them
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1983
- 1983-10-11 US US06/540,955 patent/US4532080A/en not_active Expired - Lifetime
- 1983-10-18 EP EP83870109A patent/EP0109955B1/de not_active Expired
- 1983-10-18 DE DE8383870109T patent/DE3375401D1/de not_active Expired
- 1983-10-18 AT AT83870109T patent/ATE32084T1/de active
- 1983-10-19 ZA ZA837797A patent/ZA837797B/xx unknown
- 1983-10-19 JP JP58194461A patent/JPS5991140A/ja active Granted
- 1983-10-19 AU AU20409/83A patent/AU565303B2/en not_active Ceased
- 1983-10-20 CA CA 439385 patent/CA1268476C/xx not_active Expired - Lifetime
- 1983-10-20 DD DD83255823A patent/DD210235A5/de not_active IP Right Cessation
- 1983-10-20 SU SU833654051A patent/SU1398777A3/ru active
- 1983-10-20 CS CS837732A patent/CS238650B2/cs unknown
- 1983-10-20 BR BR8305812A patent/BR8305812A/pt not_active IP Right Cessation
- 1983-10-20 IE IE2461/83A patent/IE54615B1/en not_active IP Right Cessation
- 1983-10-20 ES ES526598A patent/ES8600344A1/es not_active Expired
1985
- 1985-04-12 US US06/722,486 patent/US4704334A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
AU2040983A (en)	1984-05-03
ATE32084T1 (de)	1988-02-15
JPH052697B2 (de)	1993-01-13
EP0109955A2 (de)	1984-05-30
IE832461L (en)	1984-04-21
EP0109955B1 (de)	1988-01-20
ES526598A0 (es)	1985-10-01
JPS5991140A (ja)	1984-05-25
CA1246306A (en)	1988-12-13
AU565303B2 (en)	1987-09-10
CA1268476C (fr)	1990-05-01
IE54615B1 (en)	1989-12-06
BR8305812A (pt)	1984-05-29
DE3375401D1 (en)	1988-02-25
EP0109955A3 (en)	1985-08-14
DD210235A5 (de)	1984-06-06
SU1398777A3 (ru)	1988-05-23
ZA837797B (en)	1984-06-27
US4532080A (en)	1985-07-30
ES8600344A1 (es)	1985-10-01
US4704334A (en)	1987-11-03

Publication	Publication Date	Title
CS238650B2 (en)	1985-12-16	Composite formation containing sulphur-vulcanizable rubber mixture
RU2067974C1 (ru)	1996-10-20	Сульфидсодержащие полицитраконимиды и полиитаконимиды
US4417012A (en)	1983-11-22	Organic thiosulphates and thiosulphonates useful as stabilising agents for rubber vulcanisates
JPH0515173B2 (de)	1993-02-26
JPH04275349A (ja)	1992-09-30	ゴム加硫物
US8530549B2 (en)	2013-09-10	Rubber crawler
US20110124787A1 (en)	2011-05-26	Rubber composition
JPH0332576B2 (de)	1991-05-13
US6646029B1 (en)	2003-11-11	Pyrimidine derivatives as hardness stabilizers
US4654271A (en)	1987-03-31	Metal complexes useful as rubber/metal bonding promoters
CA1268476A (en)	1990-05-01	Adhesion promoters containing -s-so2r groups
CA1080874A (en)	1980-07-01	Compositions of unvulcanized conjugated diene polymers antihardeners
CZ9300779A3 (en)	1994-02-16	Polycitraconimides and polyitacomides containing (poly)-sulfide groups
DE2732994A1 (de)	1978-01-26	Einen vulkanisierbaren kautschuk enthaltende masse
US6465604B2 (en)	2002-10-15	Pyrimidine derivatives as hardness stabilizers
EP1335900B1 (de)	2007-04-18	Alkylthio- und aryl(heteroyl)thio-substituierte p-phenylendiamine, deren herstellung und deren verwendung in kautschuk
US2393500A (en)	1946-01-22	Composition of matter
US2256157A (en)	1941-09-16	Vulcanization of rubber
US20040006162A1 (en)	2004-01-08	Alkylthio- and aryl(heteroyl)thio-substituted p-phenylenediamines, their manufacture and their use in rubber
JPH01158058A (ja)	1989-06-21	金属との接着が良好なゴム組成物
JPS61252249A (ja)	1986-11-10	新規なゴム組成物