EP3387060A1 - Kautschukmischungen - Google Patents
KautschukmischungenInfo
- Publication number
- EP3387060A1 EP3387060A1 EP16802056.8A EP16802056A EP3387060A1 EP 3387060 A1 EP3387060 A1 EP 3387060A1 EP 16802056 A EP16802056 A EP 16802056A EP 3387060 A1 EP3387060 A1 EP 3387060A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- rubber
- general formula
- silatran
- mixtures according
- aromatic
- Prior art date
- 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.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 69
- 229920001971 elastomer Polymers 0.000 title claims abstract description 67
- 239000005060 rubber Substances 0.000 title claims abstract description 67
- 229920002379 silicone rubber Polymers 0.000 claims abstract description 5
- 239000004945 silicone rubber Substances 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 9
- 239000000945 filler Substances 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 238000013016 damping Methods 0.000 claims description 2
- 238000000465 moulding Methods 0.000 claims description 2
- 238000007789 sealing Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 150000001343 alkyl silanes Chemical class 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 238000002156 mixing Methods 0.000 abstract description 10
- XBRVPWBNRAPVCC-UHFFFAOYSA-N 4,6,11-trioxa-1-aza-5$l^{3}-silabicyclo[3.3.3]undecane Chemical compound C1CO[Si]2OCCN1CCO2 XBRVPWBNRAPVCC-UHFFFAOYSA-N 0.000 abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 230000000052 comparative effect Effects 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 229910052751 metal Inorganic materials 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 12
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 10
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 8
- 229920003048 styrene butadiene rubber Polymers 0.000 description 8
- 239000006229 carbon black Substances 0.000 description 7
- 235000019241 carbon black Nutrition 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 238000004073 vulcanization Methods 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 150000004760 silicates Chemical class 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 238000005299 abrasion Methods 0.000 description 4
- WITDFSFZHZYQHB-UHFFFAOYSA-N dibenzylcarbamothioylsulfanyl n,n-dibenzylcarbamodithioate Chemical compound C=1C=CC=CC=1CN(CC=1C=CC=CC=1)C(=S)SSC(=S)N(CC=1C=CC=CC=1)CC1=CC=CC=C1 WITDFSFZHZYQHB-UHFFFAOYSA-N 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- -1 metal chlorides Chemical class 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000011085 pressure filtration Methods 0.000 description 4
- 231100000331 toxic Toxicity 0.000 description 4
- 230000002588 toxic effect Effects 0.000 description 4
- 239000011787 zinc oxide Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 150000002357 guanidines Chemical class 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 235000005985 organic acids Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- CBXRMKZFYQISIV-UHFFFAOYSA-N 1-n,1-n,1-n',1-n',2-n,2-n,2-n',2-n'-octamethylethene-1,1,2,2-tetramine Chemical compound CN(C)C(N(C)C)=C(N(C)C)N(C)C CBXRMKZFYQISIV-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
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 229920003244 diene elastomer Polymers 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- RLAWWYSOJDYHDC-BZSNNMDCSA-N lisinopril Chemical compound C([C@H](N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(O)=O)C(O)=O)CC1=CC=CC=C1 RLAWWYSOJDYHDC-BZSNNMDCSA-N 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- MSRJTTSHWYDFIU-UHFFFAOYSA-N octyltriethoxysilane Chemical compound CCCCCCCC[Si](OCC)(OCC)OCC MSRJTTSHWYDFIU-UHFFFAOYSA-N 0.000 description 2
- 229960003493 octyltriethoxysilane Drugs 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000011164 primary particle Substances 0.000 description 2
- 230000001012 protector Effects 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229920003051 synthetic elastomer Polymers 0.000 description 2
- 239000005061 synthetic rubber Substances 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
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 150000003623 transition metal compounds Chemical class 0.000 description 2
- ALVYUZIFSCKIFP-UHFFFAOYSA-N triethoxy(2-methylpropyl)silane Chemical compound CCO[Si](CC(C)C)(OCC)OCC ALVYUZIFSCKIFP-UHFFFAOYSA-N 0.000 description 2
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 2
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 2
- TUQLLQQWSNWKCF-UHFFFAOYSA-N trimethoxymethylsilane Chemical compound COC([SiH3])(OC)OC TUQLLQQWSNWKCF-UHFFFAOYSA-N 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical class C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- DZLQWMNVOBAZGC-UHFFFAOYSA-N 5-methyl-4,6,11-trioxa-1-aza-5-silabicyclo[3.3.3]undecane Chemical compound O1CCN2CCO[Si]1(C)OCC2 DZLQWMNVOBAZGC-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 241001441571 Hiodontidae Species 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Natural products CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
- 229910052779 Neodymium Inorganic materials 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229910020175 SiOH Inorganic materials 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- WOIHABYNKOEWFG-UHFFFAOYSA-N [Sr].[Ba] Chemical compound [Sr].[Ba] WOIHABYNKOEWFG-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000005452 alkenyloxyalkyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 229920003193 cis-1,4-polybutadiene polymer Polymers 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 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
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
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- 125000000524 functional group Chemical group 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- RSKGMYDENCAJEN-UHFFFAOYSA-N hexadecyl(trimethoxy)silane Chemical compound CCCCCCCCCCCCCCCC[Si](OC)(OC)OC RSKGMYDENCAJEN-UHFFFAOYSA-N 0.000 description 1
- TZMQHOJDDMFGQX-UHFFFAOYSA-N hexane-1,1,1-triol Chemical compound CCCCCC(O)(O)O TZMQHOJDDMFGQX-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- TUMMOPTUHGUTLX-UHFFFAOYSA-N hydroxysilylformic acid Chemical compound O[SiH2]C(O)=O TUMMOPTUHGUTLX-UHFFFAOYSA-N 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 229910052976 metal sulfide Inorganic materials 0.000 description 1
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical class CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical class [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000013031 physical testing Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001698 pyrogenic effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical class OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000006234 thermal black Substances 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 150000007944 thiolates Chemical class 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- OYGYKEULCAINCL-UHFFFAOYSA-N triethoxy(hexadecyl)silane Chemical compound CCCCCCCCCCCCCCCC[Si](OCC)(OCC)OCC OYGYKEULCAINCL-UHFFFAOYSA-N 0.000 description 1
- FBBATURSCRIBHN-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyldisulfanyl)propyl]silane Chemical group CCO[Si](OCC)(OCC)CCCSSCCC[Si](OCC)(OCC)OCC FBBATURSCRIBHN-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
- C08K5/54—Silicon-containing compounds
- C08K5/549—Silicon-containing compounds containing silicon in a ring
-
- 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
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
-
- 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
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
-
- 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
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5435—Silicon-containing compounds containing oxygen containing oxygen in a ring
-
- 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
- C08K5/54—Silicon-containing compounds
- C08K5/544—Silicon-containing compounds containing nitrogen
- C08K5/5477—Silicon-containing compounds containing nitrogen containing nitrogen in a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L21/00—Compositions of unspecified rubbers
Definitions
- the present invention relates to rubber mixtures, a process for their preparation and their use.
- EP 2 206 742 discloses silatran-containing particles which are used as coupling agents between silica and rubber.
- silane derivatives of the formula R “'Si (0-CR' R” -CR 'R') 3 N, where at least one R "is an alkenyloxyalkyl group. These silane derivatives can in
- Silicone compounds are used.
- EP 1 045 006, EP 1 045 002 and EP 0 919 558 disclose silatranes for
- Silicone rubber applications are known.
- diphenylguanidine as a secondary accelerator in silica-filled rubber blends is known from various references (for example, H.-D.
- the object of the invention is to prepare rubber mixtures with accelerators which release no toxic aniline or its derivatives.
- the invention relates to rubber mixtures which are characterized in that they comprise at least one rubber, with the exception of silicone rubber, and at least one silatran of the general formula (I),
- X 1 , X 2 and X 3 are each independently hydrogen (-H), straight-chain unsubstituted or branched unsubstituted (C 1 -C 10) -alkyl, preferably straight-chain unsubstituted or branched unsubstituted (C 1 -C 6) -alkyl, particularly preferably methyl or Ethyl, mean.
- the rubber may preferably be a diene rubber.
- G may preferably be CH3CH2CH2-.
- X 1 , X 2 and X 3 may preferably be H.
- the silatran of the general formula (I) can be CH 3 CH 2 CH 2 -Si (-O-CH 2 -CH 2 -) 3N.
- Silatrans of the general formula (I) may be mixtures of silatrans of the general formula (I).
- Silatrans of the general formula (I) may contain partially hydrolyzed silatrane compounds of the general formula (I).
- Silatrans of the general formula (I) can be: CH 3 -CH 2 -si (-O-CH 2 -CH 2 -) 3 N,
- the silatrans of the formula (I) can be prepared by reacting at least one compound of the general formula (I)
- the reaction can be catalyzed or uncatalyzed.
- the alk-OH can from the
- Reaction mixture are separated continuously or discontinuously.
- Examples of compounds of the general formula III may be: triethanolamine,
- a low water content of the compounds of the formula III used can have a favorable effect on the composition and the product properties of the compounds.
- the compounds of the formula III may preferably have a water content of less than 1% by weight, particularly preferably less than 0.2% by weight.
- the reaction can be carried out in typical organic solvents having a boiling point of less than 200 ° C., preferably less than 100 ° C.
- the reaction can be carried out in the absence of organic solvents.
- metal-free or metal-containing catalysts can be used as a catalyst in the process for the preparation of silatrans of the formula (I).
- metal-containing catalysts metal compounds of the 3.-7. Group, the 13.-14. Group and / or the Lanthaniden join be used.
- transition metal compounds can be used as metal-containing catalysts.
- the metal-containing catalysts may be metal compounds such as metal chlorides, metal oxides, metal oxychlorides, metal sulfides, metal sulfochlorides, metal alcoholates, metal thiolates, metal oxyalcoholates, metal amides, metal imides, or multiple bonded ligand transition metal compounds.
- titanium alkoxides can be used as metal-containing catalysts.
- titanates such as, for example, tetra-n-butyl orthotitanate, tetraethyl orthotitanate, tetra-n-propyl orthotitanate or tetraisopropyl orthotitanate, can be used as catalysts.
- organic acids can be used as metal-free catalysts.
- suitable organic acids are trifluoroacetic acid, trifluoromethanesulfonic acid or p-toluenesulfonic acid, trialkylammonium compounds R 3 NH + X " or organic bases such as, for example, trialkylamines NR 3.
- the preparation process can be carried out at atmospheric pressure or reduced pressure, preferably between 1 and 600 mbar, more preferably between 5 and 200 mbar.
- the production process can be carried out in the temperature range between 20 ° C and 200 ° C, preferably between 35 ° C and 150 ° C.
- the reaction mixture may be added before or during the reaction substances that promote the transport of water from the product by forming azeotropic mixtures.
- the corresponding substances can be cyclic or straight-chain aliphatics, aromatics, mixed aromatic-aliphatic compounds, ethers, alcohols or acids.
- hexane, cyclohexane, benzene, toluene, ethanol, propanol, iso-propanol, butanol, ethylene glycol, tetrahydrofuran, dioxane, formic acid, acetic acid, ethyl acetate or Dimetyhlformamid can be used.
- the silatranes of formula (I) can be used as accelerators in filled rubber compounds, for example tire treads.
- the silatrans of the general formula (I) can be used in amounts of 0.1 to 8 parts by weight, preferably 0.2 to 6 parts by weight, more preferably 0.8 to 4 parts by weight, based on 100 wt. - Parts of the rubber used to be used.
- Another object of the invention is a process for the preparation of the rubber mixtures according to the invention, which is characterized in that at least one rubber and a silatrane of the formula (I) is mixed.
- the rubber mixture may contain at least one filler.
- the addition of the silatrans of the general formula (I), as well as the addition of the fillers can be carried out at melt temperatures of 100 to 200 ° C. However, it can also be carried out at lower temperatures of 40 to 100 ° C, for example together with other rubber auxiliaries.
- the silatranes of the formula (I) can be added to the mixing process both in pure form and supported on an inert organic or inorganic carrier, as well as pre-reacted with an organic or inorganic carrier.
- Preferred support materials may be precipitated or pyrogenic silicas, waxes, thermoplastics, natural or synthetic silicates, natural or synthetic oxides, preferably alumina, or carbon blacks.
- silatrans can also be pre-reacted with the filler to be used
- fillers the following fillers can be used for the rubber mixtures according to the invention:
- Carbon black The carbon blacks to be used in this case can be prepared by the flame black, furnace, gas black or thermal black process.
- the carbon blacks may have a BET surface area of 20 to 200 m 2 / g.
- the carbon blacks may also be doped, such as with Si.
- Amorphous silicas preferably precipitated silicas or fumed silicas.
- the amorphous silicas may have a specific surface area of 5 to 1000 m 2 / g, preferably 20 to 400 m 2 / g (BET surface area) and a primary particle size of 10 to 400 nm. If appropriate, the silicas may also be used as mixed oxides with others
- Metal oxides such as Al, Mg, Ca, Ba, Zn and titanium oxides are present.
- Synthetic silicates such as aluminum silicate or alkaline earth silicates, for example
- Magnesium silicate or calcium silicate The synthetic silicates with BET surface areas of 20 to 400 m 2 / g and primary particle diameters of 10 to 400 nm. - Synthetic or natural aluminas and hydroxides.
- Natural silicates such as kaolin and other naturally occurring silicas.
- Glass fiber and glass fiber products (mats, strands) or glass microspheres.
- amorphous silicas particularly preferably precipitated silicas or silicates, particularly preferably precipitated silicas having a BET surface area of from 20 to 400 m 2 / g in amounts of from 5 to 180 parts by weight, based in each case on 100 parts of rubber.
- the fillers mentioned can be used alone or in a mixture.
- 10 to 180 parts by weight of fillers, preferably precipitated silica, optionally together with 0 to 100 parts by weight of carbon black, and 0, 1 to 8 parts by weight of silatrans of the general formula I, respectively based on 100 parts by weight of rubber be used for the preparation of the mixtures.
- Natural rubber also synthetic rubbers.
- Preferred synthetic rubbers are described, for example, in W. Hofmann, Kautschuktechnologie, Genter Verlag, Stuttgart 1980. They include, among others, polybutadiene (BR),
- Styrene / butadiene copolymers for example emulsion SBR (E-SBR) or solution SBR (L-SBR), preferably with a styrene content of 1 to 60 wt .-%, particularly preferably 2 to 50 wt .-%, based on the total polymer, - chloroprene (CR),
- E-SBR emulsion SBR
- L-SBR solution SBR
- styrene content 1 to 60 wt .-%, particularly preferably 2 to 50 wt .-%, based on the total polymer, - chloroprene (CR)
- Butadiene / acrylonitrile copolymers preferably having an acrylonitrile content of 5 to 60% by weight, preferably 10 to 50% by weight, based on the total polymer (NBR), partially hydrogenated or fully hydrogenated NBR rubber (HNBR), ethylene / Propylene / diene copolymers (EPDM) or rubbers mentioned above, which additionally have functional groups, such as Carboxy, silanol or epoxy groups, for example epoxidized NR, carboxy-functionalized NBR or silanol (-SiOH) or siloxy-functionalized (-Si-OR), amino-epoxy, mercapto, hydroxy-functionalized SBR, and mixtures these rubbers.
- NBR total polymer
- HNBR partially hydrogenated or fully hydrogenated NBR rubber
- EPDM ethylene / Propylene / diene copolymers
- functional groups such as Carboxy, silanol or epoxy groups, for example epoxidized NR, carboxy-functional
- the rubber vulcanizates of the invention may comprise further rubber auxiliaries, such as reaction accelerators, anti-aging agents, heat stabilizers, light stabilizers,
- the rubber auxiliaries may be present in known amounts, inter alia, after the
- Usual amounts may be, for example, amounts of 0, 1 to 50 wt .-%, based on rubber.
- crosslinkers peroxides, sulfur or sulfur-donating substances can be used.
- Rubber compounds may also contain vulcanization accelerators.
- suitable vulcanization accelerators may be mercaptobenzothiazoles, sulfenamides, thiurams, dithiocarbamates, thioureas and thiocarbonates.
- the vulcanization accelerators and sulfur can be used in amounts of 0.1 to 10 wt .-%, preferably 0, 1 to 5 wt .-%, based on 100 parts by weight of rubber.
- the vulcanization of the rubber mixtures according to the invention can be carried out at temperatures of 100 to 200 ° C, preferably 120 to 180 ° C, optionally under pressure of 10 to 200 bar.
- the blending of the rubbers with the filler, optionally rubber auxiliaries and the silatrane can be carried out in known mixing units, such as rollers, internal mixers and mixing extruders.
- the rubber mixtures according to the invention can be used for the production of moldings, for example for the production of pneumatic tires, tire treads, cable sheaths, hoses,
- Driving belts conveyor belts, roller coverings, tires, shoe soles, sealing rings and
- the rubber mixtures according to the invention can be carried out without the addition of guanidines.
- the rubber mixture may be free from
- Guanidine derivatives preferably diphenylguanidine.
- silatrans of the general formula (I) can be used as a secondary accelerator.
- guanidine accelerator can be omitted partially or completely.
- Another object of the invention is the use of silatrans of the general formula (i),
- G is a monovalent unbranched or branched, saturated or unsaturated, aliphatic, aromatic or mixed aliphatic / aromatic (C2-Cs) -, preferably (C2-C6) -, particularly preferably (C3-C6) -, very particularly preferably (C3) -, hydrocarbon chain is,
- X 1 , X 2 and X 3 are each independently hydrogen (-H), straight-chain unsubstituted or branched unsubstituted (C 1 -C 10) -alkyl, preferably straight-chain unsubstituted or branched unsubstituted (C 1 -C 6) -alkyl, particularly preferably methyl or Ethyl, mean, in
- triethanolamine from BASF SE isobutyltriethoxysilane, hexadecyltrimethoxysilane, octyltriethoxysilane and propyltriethoxysilane from Evonik Industries AG, sodium hydroxide and phenyltrimethoxysilane from Sigma-Aldrich, ethanol and methanol from Sasol Solvents Germany GmbH, trimethoxymethylsilane from the company Merck, as well as n-hexane and n-pentane from VWR.
- the product has a melting point of 85 ° C and according to analysis by H-NMR
- the product has a melting point of 69 ° C and according to H-NMR analysis contains 98.4 wt .-% 1-Octylsilatran.
- the product has a melting point of 79 ° C and contains according to H-NMR analysis 99.8 wt .-% 1-Hexadecylsilatran.
- the product has a melting point of 55 ° C and according to H-NMR analysis contains 96.0 wt .-% of 1-isobutylsilatran.
- the product has a melting point of 205 ° C and according to H-NMR analysis contains 94.4 wt .-% 1-phenylsilatran.
- Example 5 Rubber Engineering Studies
- the recipe used for the rubber compounds is given in Table 1 below.
- the unit phr means by weight, based on 100 parts of the used
- mixture 2 mixture without secondary accelerator.
- inventive mixture 4 Silatran according to Example 1.
- mixture 5 according to the invention Silatran according to Example 2.
- inventive mixture 8 Silatran according to Example 4.
- Vulkanox ® HS / LG k 1, 5 1, 5 1, 5 1, 5 1, 5 1, 5 1, 5 1, 5 1, 5 1, 5 1, 5
- Si 266 ® Bis (triethoxysilylpropyl) from Evonik Industries AG disulfide.
- Corax® N 330 carbon black from Orion Engineered Carbons GmbH.
- ZnO zinc oxide ZnO RS RAL 844 C from Arnsperger Chemikalien GmbH.
- Perkacit TBzTD Tetrabenzylthiuram disulfide (TBzTD) based on Weber & Schaer (manufacturer: Dalian Richon).
- Vulkacit ® CZ / EG-C A / Rhein Chemie Rheinau GmbH cyclohexyl-2-benzothiazole.
- Sulfur Milling sulfur 80/90 ° from Solvay & CPC Barium Strontium GmbH & Co. KG. The mixtures are prepared in three stages in a 1.5 L internal mixer (E type) at a batch temperature of 155 ° C. according to the mixing instructions described in Table 2.
- the vulcanization takes place at a temperature of 165 ° C in a typical
- Vulcanization press with a holding pressure of 120 bar after t.95%.
- the t.95% time is determined by means of Moving The Rheometer (rotorless Vulkameter) according to ISO 6502 (paragraph 3.2 "rotorless curemeter”) at 165 ° C.
- the rubber test is carried out according to the test methods given in Table 3.
- Table 4 gives the rubber technical data for the raw mixtures and vulcanizates.
- Standard secondary accelerator DPG contains and compared to the comparison mixture 3.
- the comparative mixture 6 however, has weaknesses in the abrasion (DIN abrasion) compared to the mixtures according to the invention 4, 5, 7 and 8.
- Comparative blends Benefits in wet adhesion (ball rebound at 23 ° C) compared to the comparative blends 1, 2, 3 and 6 on.
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)
- Tires In General (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102015224436.9A DE102015224436A1 (de) | 2015-12-07 | 2015-12-07 | Kautschukmischungen |
PCT/EP2016/079023 WO2017097625A1 (de) | 2015-12-07 | 2016-11-28 | Kautschukmischungen |
Publications (1)
Publication Number | Publication Date |
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EP3387060A1 true EP3387060A1 (de) | 2018-10-17 |
Family
ID=57421852
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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EP16802056.8A Withdrawn EP3387060A1 (de) | 2015-12-07 | 2016-11-28 | Kautschukmischungen |
Country Status (15)
Country | Link |
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US (1) | US10781302B2 (ru) |
EP (1) | EP3387060A1 (ru) |
JP (1) | JP6828051B2 (ru) |
KR (1) | KR20180090279A (ru) |
CN (1) | CN108291054B (ru) |
BR (1) | BR112018011508B1 (ru) |
CA (1) | CA3007487C (ru) |
DE (1) | DE102015224436A1 (ru) |
IL (1) | IL259779B (ru) |
MX (1) | MX2018006672A (ru) |
MY (1) | MY187475A (ru) |
RU (1) | RU2736124C2 (ru) |
UA (1) | UA124194C2 (ru) |
WO (1) | WO2017097625A1 (ru) |
ZA (1) | ZA201804383B (ru) |
Families Citing this family (2)
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KR102024758B1 (ko) * | 2018-05-26 | 2019-09-25 | 에스케이이노베이션 주식회사 | 식각액 조성물, 절연막의 식각방법, 반도체 소자의 제조방법 및 실란화합물 |
CN116875064B (zh) * | 2023-07-25 | 2023-12-19 | 广州市佳合硅橡胶有限公司 | 一种耐高温混炼硅橡胶及其制备方法 |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
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SU514841A1 (ru) * | 1974-07-09 | 1976-05-25 | Иркутский Институт Органической Химии Сибирского Отделения Ссср | Способ получени бис(силатранилалкил) сульфидов |
US4048206A (en) | 1975-04-22 | 1977-09-13 | Mikhail Grigorievich Voronkov | Process for the production of 1-organylsilatranes and carbofunctional derivatives thereof |
US5945555A (en) | 1997-11-28 | 1999-08-31 | Dow Corning Toray Silicone Co., Ltd. | Silatrane derivative, method for manufacturing same, adhesion promoter, and curable silicone composition |
JP2000265063A (ja) | 1999-03-16 | 2000-09-26 | Dow Corning Toray Silicone Co Ltd | シリコーンゴム組成物 |
JP2000302977A (ja) | 1999-04-16 | 2000-10-31 | Dow Corning Toray Silicone Co Ltd | シリコーンゴム組成物 |
US6284861B1 (en) * | 1999-12-13 | 2001-09-04 | Dow Corning Toray Silicone, Ltd. | Silicone rubber composition |
DE102005038794A1 (de) * | 2005-08-17 | 2007-02-22 | Degussa Ag | Kautschukmischungen |
DE102006004062A1 (de) * | 2006-01-28 | 2007-08-09 | Degussa Gmbh | Kautschukmischungen |
JP5193470B2 (ja) * | 2007-01-12 | 2013-05-08 | 東レ・ダウコーニング株式会社 | ビス(シラトラニルアルキル)ポリスルフィド等の製造方法およびビス(シラトラニルアルキル)ポリスルフィド等の混合物 |
DE102008054967A1 (de) | 2008-12-19 | 2010-06-24 | Evonik Degussa Gmbh | Silatranhaltige Partikel |
US9109103B2 (en) * | 2013-11-25 | 2015-08-18 | The Goodyear Tire & Rubber Company | Functionalized polymer, rubber composition and pneumatic tire |
US9109073B1 (en) * | 2014-08-19 | 2015-08-18 | The Goodyear Tire & Rubber Company | Bifunctionalized polymer |
US9090730B1 (en) * | 2014-08-19 | 2015-07-28 | The Goodyear Tire & Rubber Company | Rubber composition and pneumatic tire |
US9428628B2 (en) * | 2014-08-20 | 2016-08-30 | The Goodyear Tire & Rubber Company | Functionalized polymer, rubber composition and pneumatic tire |
-
2015
- 2015-12-07 DE DE102015224436.9A patent/DE102015224436A1/de not_active Withdrawn
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2016
- 2016-11-28 MY MYPI2018702193A patent/MY187475A/en unknown
- 2016-11-28 MX MX2018006672A patent/MX2018006672A/es unknown
- 2016-11-28 CN CN201680071584.9A patent/CN108291054B/zh active Active
- 2016-11-28 UA UAA201807362A patent/UA124194C2/uk unknown
- 2016-11-28 JP JP2018548278A patent/JP6828051B2/ja active Active
- 2016-11-28 KR KR1020187015938A patent/KR20180090279A/ko not_active Application Discontinuation
- 2016-11-28 RU RU2018123802A patent/RU2736124C2/ru active
- 2016-11-28 CA CA3007487A patent/CA3007487C/en active Active
- 2016-11-28 BR BR112018011508-8A patent/BR112018011508B1/pt active IP Right Grant
- 2016-11-28 EP EP16802056.8A patent/EP3387060A1/de not_active Withdrawn
- 2016-11-28 US US15/781,257 patent/US10781302B2/en active Active
- 2016-11-28 WO PCT/EP2016/079023 patent/WO2017097625A1/de active Application Filing
-
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- 2018-06-29 ZA ZA2018/04383A patent/ZA201804383B/en unknown
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RU2018123802A (ru) | 2020-01-09 |
MX2018006672A (es) | 2018-11-09 |
CA3007487C (en) | 2022-10-04 |
CN108291054A (zh) | 2018-07-17 |
RU2018123802A3 (ru) | 2020-04-28 |
KR20180090279A (ko) | 2018-08-10 |
IL259779A (en) | 2018-07-31 |
ZA201804383B (en) | 2019-04-24 |
JP6828051B2 (ja) | 2021-02-10 |
UA124194C2 (uk) | 2021-08-04 |
BR112018011508A2 (pt) | 2018-12-04 |
JP2018538427A (ja) | 2018-12-27 |
MY187475A (en) | 2021-09-23 |
IL259779B (en) | 2022-04-01 |
CA3007487A1 (en) | 2017-06-15 |
US20180346696A1 (en) | 2018-12-06 |
US10781302B2 (en) | 2020-09-22 |
DE102015224436A1 (de) | 2017-06-08 |
CN108291054B (zh) | 2020-12-22 |
WO2017097625A1 (de) | 2017-06-15 |
BR112018011508B1 (pt) | 2022-05-17 |
RU2736124C2 (ru) | 2020-11-11 |
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