JP5340605B2 - 充填材含有ゴム用保護化メルカプトシラン・カップリング剤 - Google Patents
充填材含有ゴム用保護化メルカプトシラン・カップリング剤 Download PDFInfo
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- JP5340605B2 JP5340605B2 JP2008020843A JP2008020843A JP5340605B2 JP 5340605 B2 JP5340605 B2 JP 5340605B2 JP 2008020843 A JP2008020843 A JP 2008020843A JP 2008020843 A JP2008020843 A JP 2008020843A JP 5340605 B2 JP5340605 B2 JP 5340605B2
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- Prior art keywords
- reaction
- rubber
- silane
- temperature
- ester
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- 239000005060 rubber Substances 0.000 title claims abstract description 92
- 229920001971 elastomer Polymers 0.000 title claims abstract description 90
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical compound S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 title claims abstract description 71
- 239000000945 filler Substances 0.000 title claims abstract description 35
- 239000007822 coupling agent Substances 0.000 title description 10
- 238000000034 method Methods 0.000 claims abstract description 45
- 238000002156 mixing Methods 0.000 claims abstract description 35
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 12
- 239000000203 mixture Substances 0.000 claims description 81
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 29
- 150000001412 amines Chemical class 0.000 claims description 10
- 239000012351 deprotecting agent Substances 0.000 claims description 9
- 239000011256 inorganic filler Substances 0.000 claims description 8
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 8
- 150000002357 guanidines Chemical class 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 150000002466 imines Chemical class 0.000 claims description 3
- 150000003141 primary amines Chemical class 0.000 claims description 2
- 150000003335 secondary amines Chemical class 0.000 claims description 2
- 244000059549 Borneo rubber Species 0.000 claims 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims 1
- 229920000620 organic polymer Polymers 0.000 abstract description 11
- 229920000642 polymer Polymers 0.000 abstract description 6
- 238000005859 coupling reaction Methods 0.000 abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 5
- 230000008878 coupling Effects 0.000 abstract description 4
- 238000010168 coupling process Methods 0.000 abstract description 4
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical group SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- WTGIOQMHIHCSPZ-UHFFFAOYSA-N sulfanylsilicon Chemical class S[Si] WTGIOQMHIHCSPZ-UHFFFAOYSA-N 0.000 abstract 2
- 230000001960 triggered effect Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 114
- 229910000077 silane Inorganic materials 0.000 description 87
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 84
- -1 siloxanes Chemical class 0.000 description 60
- 150000002148 esters Chemical class 0.000 description 58
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 53
- 239000000047 product Substances 0.000 description 51
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 45
- 239000011593 sulfur Substances 0.000 description 44
- 229910052717 sulfur Inorganic materials 0.000 description 44
- 238000007792 addition Methods 0.000 description 43
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 238000004821 distillation Methods 0.000 description 33
- 150000004756 silanes Chemical class 0.000 description 29
- 239000002904 solvent Substances 0.000 description 29
- 239000003054 catalyst Substances 0.000 description 28
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 27
- 239000002253 acid Substances 0.000 description 26
- 238000010992 reflux Methods 0.000 description 26
- 239000000377 silicon dioxide Substances 0.000 description 25
- 150000003839 salts Chemical class 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 21
- 125000000524 functional group Chemical group 0.000 description 21
- 239000000243 solution Substances 0.000 description 20
- 229910052783 alkali metal Inorganic materials 0.000 description 19
- 239000007788 liquid Substances 0.000 description 17
- 125000006239 protecting group Chemical class 0.000 description 17
- 230000015572 biosynthetic process Effects 0.000 description 15
- 229920003052 natural elastomer Polymers 0.000 description 15
- 229920001194 natural rubber Polymers 0.000 description 15
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 15
- 244000043261 Hevea brasiliensis Species 0.000 description 14
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 14
- 238000010438 heat treatment Methods 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- 230000008569 process Effects 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- 239000002585 base Substances 0.000 description 12
- 239000003153 chemical reaction reagent Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 11
- 238000004817 gas chromatography Methods 0.000 description 11
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 10
- 150000001340 alkali metals Chemical class 0.000 description 10
- 238000009835 boiling Methods 0.000 description 10
- 239000006229 carbon black Substances 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 150000007970 thio esters Chemical class 0.000 description 10
- 239000008096 xylene Substances 0.000 description 10
- 150000008065 acid anhydrides Chemical class 0.000 description 9
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 238000004898 kneading Methods 0.000 description 9
- 238000012545 processing Methods 0.000 description 9
- 239000004594 Masterbatch (MB) Substances 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 8
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 8
- 125000003396 thiol group Chemical class [H]S* 0.000 description 8
- 238000005809 transesterification reaction Methods 0.000 description 8
- 238000005096 rolling process Methods 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 6
- VTXSDKVOHQXOBQ-UHFFFAOYSA-N C1CCS[SiH2]C1 Chemical compound C1CCS[SiH2]C1 VTXSDKVOHQXOBQ-UHFFFAOYSA-N 0.000 description 6
- SMDVDXOWTRMZKF-UHFFFAOYSA-N C1C[SiH2]SC1 Chemical compound C1C[SiH2]SC1 SMDVDXOWTRMZKF-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 239000003963 antioxidant agent Substances 0.000 description 6
- 230000008901 benefit Effects 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 6
- 229920002857 polybutadiene Polymers 0.000 description 6
- 239000011148 porous material Substances 0.000 description 6
- 229920003048 styrene butadiene rubber Polymers 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 150000003609 titanium compounds Chemical class 0.000 description 6
- 229910052723 transition metal Inorganic materials 0.000 description 6
- 150000003624 transition metals Chemical class 0.000 description 6
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 5
- 239000005062 Polybutadiene Substances 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 5
- 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 5
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 5
- 229920003244 diene elastomer Polymers 0.000 description 5
- 239000012990 dithiocarbamate Substances 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
- 229910052753 mercury Inorganic materials 0.000 description 5
- 239000012434 nucleophilic reagent Substances 0.000 description 5
- 239000005077 polysulfide Substances 0.000 description 5
- 229920001021 polysulfide Polymers 0.000 description 5
- 150000008117 polysulfides Polymers 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 229920001897 terpolymer Polymers 0.000 description 5
- 150000003606 tin compounds Chemical class 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 4
- 229910052977 alkali metal sulfide Inorganic materials 0.000 description 4
- 125000000746 allylic group Chemical group 0.000 description 4
- 125000001743 benzylic group Chemical group 0.000 description 4
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 239000000498 cooling water Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 4
- 238000007720 emulsion polymerization reaction Methods 0.000 description 4
- 238000007701 flash-distillation Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- ZVAHTTMDGSREKY-UHFFFAOYSA-N s-(3-triethoxysilylpropyl) ethanethioate Chemical compound CCO[Si](OCC)(OCC)CCCSC(C)=O ZVAHTTMDGSREKY-UHFFFAOYSA-N 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 4
- 229960002447 thiram Drugs 0.000 description 4
- 239000011787 zinc oxide Substances 0.000 description 4
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 239000006087 Silane Coupling Agent Substances 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- 239000002174 Styrene-butadiene Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 150000001993 dienes Chemical class 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- BKBMACKZOSMMGT-UHFFFAOYSA-N methanol;toluene Chemical compound OC.CC1=CC=CC=C1 BKBMACKZOSMMGT-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 230000002028 premature Effects 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- VTDGQIKUNVKXLV-UHFFFAOYSA-N s-(2-trimethoxysilylethyl) ethanethioate Chemical compound CO[Si](OC)(OC)CCSC(C)=O VTDGQIKUNVKXLV-UHFFFAOYSA-N 0.000 description 3
- MOPINAXCCFNGGW-UHFFFAOYSA-N s-(3-trimethoxysilylpropyl) ethanethioate Chemical compound CO[Si](OC)(OC)CCCSC(C)=O MOPINAXCCFNGGW-UHFFFAOYSA-N 0.000 description 3
- AQSMLSJHYWHNRT-UHFFFAOYSA-N s-(3-trimethoxysilylpropyl) propanethioate Chemical compound CCC(=O)SCCC[Si](OC)(OC)OC AQSMLSJHYWHNRT-UHFFFAOYSA-N 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 239000008117 stearic acid Substances 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- 230000000930 thermomechanical effect Effects 0.000 description 3
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 239000003039 volatile agent Substances 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- BIGOJJYDFLNSGB-UHFFFAOYSA-N 3-isocyanopropyl(trimethoxy)silane Chemical group CO[Si](OC)(OC)CCC[N+]#[C-] BIGOJJYDFLNSGB-UHFFFAOYSA-N 0.000 description 2
- DCQBZYNUSLHVJC-UHFFFAOYSA-N 3-triethoxysilylpropane-1-thiol Chemical compound CCO[Si](OCC)(OCC)CCCS DCQBZYNUSLHVJC-UHFFFAOYSA-N 0.000 description 2
- 102100030310 5,6-dihydroxyindole-2-carboxylic acid oxidase Human genes 0.000 description 2
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 2
- 101000773083 Homo sapiens 5,6-dihydroxyindole-2-carboxylic acid oxidase Proteins 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 2
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- 239000006057 Non-nutritive feed additive Substances 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001343 alkyl silanes Chemical class 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
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- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
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- DUYAAUVXQSMXQP-UHFFFAOYSA-M thioacetate Chemical compound CC([S-])=O DUYAAUVXQSMXQP-UHFFFAOYSA-M 0.000 description 1
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- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
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- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
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- BRTXVSVHFSOGED-UHFFFAOYSA-N triethoxy(4-hydroxysulfonothioylbutyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCCS(O)(=O)=S BRTXVSVHFSOGED-UHFFFAOYSA-N 0.000 description 1
- RBDAXWQGOZWYFH-UHFFFAOYSA-N triethoxy(4-hydroxysulfonothioylpentyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCC(C)S(O)(=O)=S RBDAXWQGOZWYFH-UHFFFAOYSA-N 0.000 description 1
- SHQJOFANKPSLCU-UHFFFAOYSA-N triethoxy-(4-hydroxysulfonothioyl-4-propyl-3H-naphthalen-2-yl)silane Chemical compound C1=CC=C2C(CCC)(S(O)(=O)=S)CC([Si](OCC)(OCC)OCC)=CC2=C1 SHQJOFANKPSLCU-UHFFFAOYSA-N 0.000 description 1
- XGCGZQRQPNUUPB-UHFFFAOYSA-N triethoxy-(5-hydroxysulfonothioyl-5-propylcyclohexa-1,3-dien-1-yl)silane Chemical compound CCCC1(S(O)(=O)=S)CC([Si](OCC)(OCC)OCC)=CC=C1 XGCGZQRQPNUUPB-UHFFFAOYSA-N 0.000 description 1
- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 description 1
- HIZCIEIDIFGZSS-UHFFFAOYSA-L trithiocarbonate Chemical compound [S-]C([S-])=S HIZCIEIDIFGZSS-UHFFFAOYSA-L 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- NEYNBSGIXOOZGZ-UHFFFAOYSA-L zinc;butoxymethanedithioate Chemical compound [Zn+2].CCCCOC([S-])=S.CCCCOC([S-])=S NEYNBSGIXOOZGZ-UHFFFAOYSA-L 0.000 description 1
- MBBWTVUFIXOUBE-UHFFFAOYSA-L zinc;dicarbamodithioate Chemical compound [Zn+2].NC([S-])=S.NC([S-])=S MBBWTVUFIXOUBE-UHFFFAOYSA-L 0.000 description 1
Classifications
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- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
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- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4075—Esters with hydroxyalkyl compounds
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
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- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
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- C08J3/203—Solid polymers with solid and/or liquid additives
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K5/5406—Silicon-containing compounds containing elements other than oxygen or nitrogen
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- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
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Description
本発明のシラン類は、そのメルカプト基が保護されている(ブロックされている)メルカプトシラン誘導体である;即ち、そのメルカプト水素原子が他の基(以後“保護化基”として引用する)で置換されている。特に、本発明のシラン類は、その保護化基が一重結合で硫黄に直接化学的に結合している不飽和ヘテロ原子もしくは炭素を含んでいる保護化メルカプトシラン類である。この保護化基は、場合によっては、一種またはそれ以上のカボキシラ−トエステルまたはカルボン酸官能基で置換されていてもよい。無機充填材含有ゴムの製造におけるこれらのシラン類の使用は、脱保護化剤を使用することにより、それら保護化シランがゴム製造工程中に脱保護化されることを示している。
シラン構造物
この保護化メルカプトシラン類は、次の式(1−2)で示される:
[[(ROC(=O))p −(G)j ]k −Y−S]r −G−(SiX3 )s (1)
[(X3 Si)q −G]a −[Y−[S−G−SiX3 ]b ]c (2)
式中:
Yは、望ましくは、以下の基:−C(=NR)−; −SC(=NR)−; −SC(=O)−; (−NR)C(=O)−;(−NR)C(=S)−; −OC(=O)−; −OC(=S)−; −C(=O)−;−SC(=S)−; −C(=S)−; −S(=O)−; −S(=O)2 − ; −OS(=O)2 − ; (−NR)S(=O)2 − ; −SS(=O)−; −OS(=O)−; (−NR)S(=O)−;−SS(=O)2 − ; (−S)2 P(=O)−;(−S)P(=O)−;−P(=O)(−)2 ;(−S)2 P(=S)−; −(−S)P(=S)−; −P(=S)(−)2 ;(−NR)2 P(=O)− ;(−NR)(−S)P(=O)− ; (−O)(−NR)P(=O)− ; (−O)(−S)P(=O)− ; (−O)2 P(=O)−; −(−O)P(=O)−; −(−NR)P(=O)− ; (−NR)2 P(=S)− ; (−NR)(−S)P(=S)− ; (−O)(−NR)P(=S)− ; (−O)(−S)P(=S)− ; (−O)2 P(=S)−; −(−O)P(=S)−;および−(−NR)P(=S)−、から成る群から選ばれる多価の種:(Q)z A(=E)であり、ここで、その不飽和ヘテロ原子(E)に付いている原子Aは、基Gを経由してケイ素原子に連結されている硫黄に付いており;
各Rは、独立に、水素、不飽和結合を含んでいることも含んでいないこともある直鎖、環式あるいは分岐アルキル基、アルケニル基、アリ−ル基およびアラルキル基から選ばれ、各Rは1から18個の炭素原子を含んでおり;
各Gは、独立に、アルキル、アルケニル、アリ−ルまたはアラルキルの置換により誘導される一価もしくは多価の基で、1から18個の炭素原子を含んでおり;Gは、そのシランがチオカルボニル基の次に炭素−炭素二重結合を含むα,β不飽和カルボニルを含んでいるシランとなるものではなく、且つ、若しGが一価なら(即ちP=0なら)、Gは水素原子であることを前提条件とし;
Xは、独立に、−Cl、−Br、RO−、RC(=O)O−、R2 C=NO−、R2 NO−或いはR2 N−、−R、−(OSiR2 )t (OSiR3 )からなる群から選ばれる基であり、ここでRおよびGの各々は、上と同じであり、そして少くとも一つのXは−Rではなく;
Qは、酸素、硫黄もしくは(−NR−)であり;
Aは、炭素、硫黄、リン、もしくはスルホニルであり;
Eは、酸素、硫黄もしくはNRであり;
pは0から5であり;rは1から3であり;zは0から2であり;qは0から6であり;aは0から7であり;bは1から3であり;jは0から1であるが、pが1の場合だけ0であり;cは1から6、望ましくは1から4であり;tは0から5であり;sは1から3であり;kは1から2であって、(A)若しAが炭素、硫黄またはスルホニルであれば、(i)a+b=2そして(ii)k=1であり;(B)若しAがリンであれば、(i)c>1で且つ(ii)b=1(この場合はa=c+1である)でなければ、a+b=3であり;そして(C)若しAがリンであれば、kは2であることが前提条件である。
Gの例は、−(CH2 )n −(式中、nは、1から12である)、ジエチレンシクロヘキサン、1,2,4−トリエチレンシクロヘキサンおよびジエチレンベンゼンである。この分子中のG基中の炭素原子の和は、3から18より望ましくは6から14である。この保護化メルカプトシラン類中の、このような炭素量は、無機充填剤が有機重合体に分散することを容易にし、それによって、その充填材含有硬化ゴムの諸性質のバランスを改善する。
Xの特定例は、メトキシ、エトキシ、イソブトキシ、プロポキシ、イソプロポキシ、アセトキシおよびオキサマ−トである。メトキシ、アセトキシおよびエトキシが推奨される。少くとも一つのXは、反応性(即ち、加水分解性)でなければならない。
保護化メルカプトシラン類の合成法は、適切な離脱基の置換による、または炭素−炭素二重結合を横断する付加反応による、硫黄−含有シラン中の硫黄のエステル化およびシランへのチオエステル基の直接組込みを含んでいる。チオエステルシラン調製のための合成法の実例に含まれるのは:反応1)メルカプトシランと希望する生成物中に存在するチオエステル基に対応する酸無水物との反応;反応2)メルカプトシランのアルカリ金属塩と適切な酸無水物もしくは酸ハライドとの反応;反応3)メルカプトシランとエステルとの間のエステル交換反応(場合により、酸、塩基、スズ化合物、チタン化合物、遷移金属、または、そのエステルに対応する酸の塩のような任意の適した触媒を使用する);反応4)チオエステルシランと他のエステルとの間のエステル交換反応(場合により、酸、塩基、スズ化合物、チタン化合物、遷移金属、または、そのエステルに対応する酸の塩のような任意の適した触媒を使用する);反応5)1−シラ−2−チアシクロペンタンもしくは1−シラ−2−チアシクロヘキサンとエステルとの間のエステル交換反応(場合により、酸、塩基、スズ化合物、チタン化合物、遷移金属、または、そのエステルに対応する酸の塩のような任意の適した触媒を使用する);反応6)紫外線、熱もしくは、適切なラジカル開始剤を触媒とする、アルケン−官能性シランの炭素−炭素二重結合を横断するチオ酸のラジカル付加反応、この場合そのチオ酸がチオカルボン酸なら、この二つの試薬を、どちらが他方に加えられるとしても、その付加が進む前に実質的な反応の進行を保証するような方法で、お互いに接触させる;および反応7)チオ酸のアルカリ金属塩とハロアルキルシランとの反応、である。
本明細書で説明される保護化メルカプトシラン類は、有機重合体(即ちゴム)と無機の充填材のカップリング剤として有用である。この保護化メルカプトシラン類は、普通、メルカプトシランを使用することに関連する、例えば加工時の高い粘度、希望するより悪い充填材の分散、早期硬化(スコ−チ)および臭気などの好ましくない副次的な効果なしに、そのメルカプト基の高い効率を利用できるということで斬新である。これらの利点は、メルカプト基が、その保護基のために最初は非反応性であるので達成される。この保護基は、そのシランが、ゴムの混練中に有機重合体とカップリングすることを実質的に防ぐ。一般に、この混練工程では、シランの−SiX3 基と充填材との反応だけが起こり得る。かくして、その充填材のその重合体への実質的なカップリングは、混合中は排除され、それにより、好ましくない早期硬化(スコ−チ)および、それに関連する好ましくない粘度の増大を最少限に抑える。早期硬化を避けることにより、高いモジュラスと摩耗抵抗性のバランスのような、より良好な充填材含有ゴムの性質が達成される。
(A)(i)100重量部の、共役ジエン単独重合体および共重合体および少くとも一種の共役ジエンと芳香族ビニル化合物との共重合体から選ばれる少くとも一種の硫黄硬化性ゴム、(ii)5から100望ましくは25から80phr(ゴム100部当たりの部)の微粒子状充填材(この充填材は1から85重量パ−セントのカ−ボンブラックを含んでいるのが望ましい)、(iii)0.05から20重量部の少くとも一種の保護化メルカプトシランを、少くとも一つの予備混合工程で、このような混合工程(一工程または複数工程)のために140℃から200℃、或いはまた140℃から190℃の温度で、総混合時間:2から20或いはまた4から15分の間、熱機械的に混合する工程;
(B)次いで、最終熱機械的混合工程で、50℃から130℃の温度で、1から30分、より望ましくは1から3分の間、充填材の約0.05から20重量部の少くとも一種の脱保護化剤および0から5phrの硬化剤、とブレンドする工程;そして、場合によっては、
(C)130℃から200℃の温度で、約5から60分の間、該混合物を硬化する工程。
その孔の5パ−セント或いはそれ未満が、約10nm以下の直径を有し;その孔の60から90パ−セントが約10から約100nmの直径を有し;その孔の10から30パ−セントが約100から約1000nmの直径を有し;そして、その孔の5から20パ−セントが約1000以上の直径を有している。
以下の実施例を参照することにより、本発明はより良く理解されるであろう。実施例中、部およびパ−セントは、特に断らない限り、重量で与えられる。
5−リットルのフラスコに、15段のOldershaw(オ−ルダ−シャウ)蒸留カラム(プレ−トの直径28mm)を取付け、それに凝縮器と、還流比を制御し調節できる蒸留ヘッドを取付けた。電子温度制御装置に連結された調節器で制御された電熱式マントルを用いて、そのフラスコに熱を供給した。そのヘッド中の蒸気温度も監視した。この系を窒素雰囲気下に保持した。真空度の制御は、低温トラップと蒸留ヘッドの間に挿入した吹き出し弁(bleeder valve)により、強化された。
用いた装置は、実施例1の装置と同じであった。5−リットルのフラスコに、1074グラムの3−(トリメトキシシリル)−1−プロピルメルカプタンと561.4グラムの無水酢酸を加えた。この系を脱気し、吹出し弁を殆ど閉めた位置にして用いて、連続的に減圧にし続けた。5−リットルのフラスコ内の温度をゆっくり120℃に上げ、この時点で、<30℃で凝縮物の捕集を始めた。この5−リットルのフラスコで、155℃の温度で、それ以上捕集できなくなるまで蒸留を続け、その時点で加熱を停止し、明瞭に酢酸メチルの臭いがする184グラムの透明で無色の液体を得た。その比重が0.898であることと、炭酸ソ−ダ水溶液に反応しないことを併せて、存在する殆どの部分はメタノ−ルであると推定された。次いで、5−リットルのフラスコの温度をゆっくり195℃に上げ、追加の、全部で266グラムの凝縮物を得た。5−リットルフラスコを225℃までゆっくり加熱しながら、蒸留を続け、吹出し弁を開けた。最高ヘッド温度104℃で、379グラムの透明で無色の液体が捕集された。GC分析は、この留出物の主成分は、出発原料と生成シランの両方であることを示し、臭いから少量の酢酸が検出された。
用いた装置は、実施例1の装置と同じであった。5−リットルのフラスコに、1775グラムの3−(トリメトキシシリル)−1−プロピルメルカプタンを加えた。このメルカプトシランとの反応用に、全部で4719グラムの無水酢酸を用意し、その内の1002グラムはメルカプトシランと共に、5−リットルのフラスコに加えた。この5−リットルのフラスコへの熱流を、ヘッド温度54℃で、留出物の定常的捕集が確立されるまで、徐々に増やした。全部で840グラムの留出物が捕集され、これは、NMR分析により酢酸メチル、酢酸およびメタノ−ルを100/2/2.7モル比で含んでいることが分った。冷却した5−リットルフラスコに、追加の2015グラムの無水酢酸を加え、蒸留を再開し、923グラムの留出物を得た。次いで、701グラムの無水酢酸を加え、この工程の3回目を行い、834グラムの留出物を得た。次いでヘッドに減圧を加え始めた。その真空度は、吹出し弁を経て凝縮器からの熱を除去するために用いる冷却水の温度に近い温度で、その留出物を捕集するのに必要な水準に調整され維持された。この工程中、5−リットルのフラスコ内の温度は170℃までに抑えられた。この吹出し弁を、捕集速度が減少し始めるまで徐々に開いた。追加の896グラムの留出物を捕集し、そのカラムとヘッドの中に残った任意の液体を蒸発させた。最終留出物のGC分析は、無水酢酸より揮発性の小さい物は何も留出していないことを示した。このフラスコの内容物を冷却して得た粘ちょうな黒褐色のオイルを窒素下で貯蔵した。
816グラムの3−メルカプト−1−プロピルトリメトキシシラン、ナトリウムメトキシドの25重量%メタノ−ル溶液871グラムおよび1724グラムのトルエンを5−リットルのフラスコに窒素下で装填した。この混合物を撹拌するとピンクに発色した。このフラスコから、メタノ−ル−トルエン共沸混合物としてメタノ−ルを留去すると、その間にフラスコの内容物は無色に変わった。蒸留ヘッドでの温度が63℃から108℃に上昇するのと符号して、留出物中に密度の大きい流れが現れ、この時点でフラスコからのメタノ−ルの除去が完了したことを示した。続けて撹拌しながら、フラスコの内容物を放冷し、次いで氷水−浴に入れた。このフラスコに、361グラムのプロピオニルクロリドを、滴下により、そして/または少量ずつ加え、反応が完結するまで氷水−浴中での撹拌を続けた。撹拌している混合物の少量を周期的に採取してpH試験紙に着けた。アルカリ性になると反応が完結したことを示す。この最終混合物は、生成物のトルエン溶液中にNaClが懸濁した白い懸濁液であった。この混合物をろ過し、そして溶媒をろ液から除去して、淡褐色の生成物を得た。ガスクロマトグラフィ−は、5パ−セントの3−メルカプト−1−プロピルトリメトキシシラン、25パ−セントの3−(メチルチオ)−1−プロピルトリメトキシシラン、70パ−セントの3−(アセチルチオ)−1−プロピルトリメトキシシラン(生成物)、を示した。1〜2グラムの粉末のナトリウム・メトキシドを加えたフラッシュ蒸留で無色の生成物を得た。このナトリウム・メトキシドは、残留している任意の酸性物の中和を保障するために加えられた。場合によっては、さらに分別蒸留して、純度98%以上(GC法)の生成物を得た。
1035グラムの3−メルカプト−1−プロピルトリメトキシシラン、ナトリウムメトキシドの25重量%メタノ−ル溶液1096グラムおよび1764グラムのトルエンを5−リットルのフラスコに窒素下で装填した。この混合物を撹拌するとピンクに発色した。このフラスコを64℃の温浴に入れた。減圧下で、フラスコから、メタノ−ル−トルエン共沸混合物としてメタノ−ルを留去した。減圧度を、蒸留ヘッドでの温度が30から35℃に維持されるように保ち、その間に、トルエン−メタノ−ル共沸混合物から成る1500mLの留出物が捕集された。その間にフラスコの内容物は無色に変わった。追加のトルエン429グラムを加え、蒸留を再開した。蒸留ヘッドでの温度が35℃から55℃に上昇するのと符号して、留出物中に密度の大きい流れが現れ、そして凝縮器中での液体の表面張力に変化が現れ、この時点でフラスコからのメタノ−ルの除去が完了したことを示した。フラスコの内容物は粘ちょうな液体になった。撹拌を続けながら、フラスコの内容物を放冷した。このフラスコを氷水−浴に入れると、外見的に半固体状のペ−ストになった。このフラスコに、457グラムのプロピオニルクロリドを、滴下により、そして/または少量ずつ加え、反応が完結するまで氷水−浴中での撹拌を続けた。撹拌している混合物の少量を周期的に採取した。アルカリ性になると反応が完結したことを示す。この最終混合物は、生成物のトルエン溶液中にNaClが懸濁した白い懸濁液であった。この混合物をろ過し、そして溶媒をろ液から除去して、殆ど無色の生成物を得た。ガスクロマトグラフィ−は、3(重量)パ−セントの3−メルカプト−1−プロピルトリメトキシシラン、1パ−セントの3−(メチルチオ)−1−プロピルトリメトキシシランおよび96パ−セントの3−(アセチルチオ)−1−プロピルトリメトキシシラン(生成物)、を示した。1〜2グラムの粉末のナトリウム・メトキシドを加えたフラッシュ蒸留で無色の生成物を得た。このナトリウム・メトキシドは、残留している任意の酸性物の中和を保障するために加えられた。場合によっては、さらに分別蒸留して、純度98%以上(GC法)の生成物を得た。
763グラムの3−メルカプト−1−プロピルトリエトキシシランとナトリウムエトキシドの21重量%エタノ−ル溶液1013グラムを、5−リットルのフラスコに窒素下で装填した。この混合物から、48kPaで、最高温度45℃で870グラムのエタノ−ルを蒸留した。このフラスコの内容物に、1550グラムのトルエンを窒素下で加えた。残りのエタノ−ルを、最高温度60℃、最高絶対圧力48kPaで、エタノ−ル−トルエン共沸混合物を留去することにより、フラスコから除去した。減圧度は、蒸留ヘッドでの温度が30から40℃に維持されるように保たれた。蒸留ヘッドでの温度が35℃から約60℃に上昇するのと符号して、留出物中に密度の大きい流れが現れ、そして凝縮器中での液体の表面張力に変化が現れることと符号して、この時点でフラスコからのエタノ−ルの除去が完了したことを示した。この工程の終りに、フラスコの内容物は透明なオレンジ色の液体になった。
2513グラムのビニルトリエトキシシランを5−リットルのフラスコに入れ、撹拌しながら還流するまで加熱した。揮発性の不純物を除去するために、25mLの前カットを留去した。加熱を止め、そして、全量で1005グラムのチオ−ル酢酸を二つに分けた第1の335グラムを、スム−スな還流を維持できる速度で、数分かけて添加した。この添加の終わりに向けて、還流を維持するために必要なら熱を加えた。0.8グラムのジ−t−ブチルペルオキシドを凝縮器を通して加えると、還流速度が加速されることで証明されるように直ちに反応が起きた。加熱マントルの電源を切った。この還流中、数分以内に温度が160℃近くに上がり、その後還流がおさまり、容器内の淡黄色の内容物の温度が下がり始めた。
機械的撹拌機、添加用ロ−ト、熱電対、窒素導入管および温度調節器を備えた12リットルの三つ口丸底フラスコに、1,021グラムの3−メルカプトプロピルトリエトキシシラン(Witco Corp.of Greenwich,CTの子会社:OSi Specialties,Inc.からのSILQUESTR A−1891シラン)と433グラムのトリエチルアミンおよび3,000mLのヘキサンを装填した。この溶液を氷水−浴中で冷却し、そして693グラムのオクタノイルクロリドを添加用ロ−トを通して、2時間かけて添加した。この酸クロリドの添加完了後に、この混合物を、塩を除去するために、加圧ろ過機を用いて二回(第1回目は、0.1μmのフィルタ−を通して、第2回目は、0.01μmのフィルタ−を通して)ろ過した。溶媒を減圧下で除去した。残った黄色の液体を減圧蒸留して、1,349グラムのオクタノイルチオプロピルトリエトキシシランを、透明で極く淡い黄色の液体として得た。収率は87パ−セントであった。
この実施例は、チオ−ルカルボン酸の塩から、シランのアルコキシ基に対応するアルコ−ルを溶媒として用いて、チオカルボキシラ−ト・アルコキシシランを合成する方法を例示している。磁気撹拌棒、温度標識/調節器、加熱マントル、添加用ロ−ト、凝縮器および窒素導入管を備えた250mLの三つ口丸底フラスコに、ナトリウム・エトキシドの21重量パ−セントエタノ−ル溶液63グラムを装填した。温度を65℃以下に保ちながら、15グラムのチオ−ル酢酸をゆっくり添加した。この溶液を室温まで放冷し、そして48グラムのクロロプロピルトリエトキシシランを添加用ロ−トを通して添加した。添加完了後、24時間の間に70℃に加熱すると、白色の固体が生成した。この溶液をガスクロマトグラフィ−で分析し、78パ−セントの収率で、アセチルチオプロピルトリエトキシシランが生成したことを示した。
この実施例は、チオ−ルカルボン酸の塩から、非プロトン溶媒を溶媒として用いて、チオカルボキシラ−ト・アルコキシシランを合成する方法を例示している。磁気撹拌棒、温度標識/調節器、加熱マントル、添加用ロ−ト、凝縮器、窒素導入管および氷水浴を備えた1リットルの三つ口丸底フラスコに、粉末状のナトリウム・エトキシドと600mLのジグライムを装填した。この溶液を8℃に冷却し、温度を60℃以下に保ちながら、105グラムのチオ−ル酢酸を添加用ロ−トを通してゆっくり添加した。この溶液を35℃まで放冷し、そして250グラムのクロロメチルトリエトキシシランを添加用ロ−トを通して添加した。添加完了後、溶液を70℃に加熱すると、短時間、120℃までの発熱が観測された。この溶液を、さらに3時間70℃で加熱した。生成した白い固体を、先ず、0.1μmの加圧フィルタ−を通して、次いで、0.01μmのフィルタ−で、ろ過すると、透明で黒色の溶液が得られた。溶媒を減圧下で除去し、そして残った液体を減圧蒸留して、163グラムの透明で無色の液体を、55パ−セントの収率で得た。
配合処方
表1に記載したようなモデル低ころがり抵抗性乗用車タイヤトレッド配合および混合法を用いて、本発明のシラン類の代表的実施例を評価した。実施例1でのシランが、内容積103inch3 (1690cc)の“B”バンバリ−R (BANBURYR )ミキサ−(Farrell Corp.)中で以下のようにして混合された。このゴムマスタ−バッチの混合は、二工程で行われた。このミキサ−は、回転数120rpmで、冷却水を満たして始動された。このミキサ−にゴム重合体を入れ、30秒押し突き混合した。シリカの半分とエチレンン−酢酸ビニル(EVA)バッグに入れた、そのシリカの約35−40グラムを含むシランの全量を添加し、30秒押し突き混合した。次に、残りのシリカとEVAバッグに入れたオイルを添加し、30秒押し突き混合した。このミキサ−のスロ−トを三回粉付けし(dusted)、そしてこの混合物を各回15秒押し突き混合した。そのゴム・マスタ−バッチの温度を160および165℃の間に上げる必要に応じて、ミキサ−の混合速度を、約1分間で160または240rpmに上げた。このマスタ−バッチを排出し(そのミキサ−から取出す)、約50から60℃にセットしたロ−ルミルでシ−トに成形し、次いで常温まで放冷した。
ころがり抵抗性の小さい乗用車タイヤトレッド用モデル配合物と実施例12の混合法を用いて、N,N'−ジフェニルグアニジン(DPG)の三添加水準で、実施例1のシランを評価した。結果を下の表3に表示した。
配合組成:60ブ−デン1207BR;40SMR−NR;45ゼオシル1165MPシリカ;5カルゾル5550加工脂;3カルボワックス3350PEG;5カドックス720−C酸化亜鉛;1インダストレンRステアリン酸;1BHT酸化防止剤;1サンノライト−240ワックス;1.9ゴム製造業者用硫黄−104;1.3MBTS;0.5MBT;0.2TMTM;シラン−SILQUEST−A1289シラン(TESPT)またはアセチルチオプロピルトリエトキシシラン(アセチル)。各量はphrで示される。“Add Sulfur”(“追加硫黄”)または“Add S”という用語は“アセチル”中の硫黄の量を、TESPT由来の硫黄の量と等しくするために追加の硫黄を加えたことを意味する。結果を下の表4に示した。
低ころがり抵抗性タイヤ配合物中で以下のシラン類を試験した:TESPT(A);TESPM(B);3−アセチルチオ−1−プロピルトリメトキシシラン(C);3−アセチルチオ−1−プロピルトリエトキシシラン(D);3−オクタノイルチオ−1−プロピルトリエトキシシラン(E);3−パルミトイルチオ−1−プロピルトリエトキシシラン(F);3−エチルヘキサノイル−1−プロピルトリエトキシシラン(G);3−プロピオニルチオ−1−プロピルトリメトキシシラン(H);3−ベンゾイルチオ−1−プロピルトリエトキシシラン(I);アセチルチオメチルトリメトキシシラン(J);アセチルチオエチルトリメトキシシラン(K);アセチルチオエチルトリエトキシシラン(L);アセトチオエチルメチルトリメトキシシラン(M);アセチルチオオクチルトリメトキシシラン(N);アセチルチオオクチルトリエトキシシラン(O);アセチルチオシクロヘキシルエチルトリメトキシシラン(P)およびアセトチオノルボルニルエチルトリメトキシシラン(Q)。配合処方(量はphrで与えられる)は、75ソルフレックス(SOLFLEX)1216SSBR;25ブ−デン(Budene)1207BR;80ゼオシル(ZEOSIL)1165MPシリカ;32.5サンデックス(SUNDEX)3125加工オイル;2.5カドックス(KADOX)720−C酸化亜鉛;1.0インダストレン(INDUSTRENE)Rステアリン酸;2.0サントフレックス(SANTOFLEX)13酸化防止剤;1.5M4067マイクロワックス;3.0カ−ボンブラック−N330 ;1.4ゴム製造業者用硫黄−104;1.7CBS;2.0DGP;表に示されているシラン、である。
Claims (5)
- a.ゴム、3-トリメトキシシリル-1-プロピルチオオクトエートおよび3-トリエトキシシリル-1-プロピルチオオクトエートから成る群から選ばれる保護化メルカプトシラン、ならびに無機充填材を混合し;
b.工程(a)の混合物に、そのメルカプトシランを脱保護化するための、水、アルコール、第1アミン類、第2アミン類、イミン類、グアニジン類から成る群から選ばれ、ただし、前記アミンが少なくとも一つのN-H結合を含有する脱保護化剤および硬化剤を混合し、そして
c.その混合物を硬化させる、
工程を含んでなる、充填材含有ゴムの製造方法。 - 該メルカプトシランが3-トリエトキシシリル-1-プロピルチオオクトエートである、請求項1に記載の方法。
- ゴム組成物であり、
a.3-トリメトキシシリル-1-プロピルチオオクトエートおよび3-トリエトキシシリル-1-プロピルチオオクトエートから成る群から選ばれる保護化メルカプトシラン;
b.ゴム;および
c.無機充填材;
を含んでなり、ここで、当該ゴム組成物は、本質的に官能化されたシロキサンを含まない。 - 3-トリメトキシシリル-1-プロピルチオオクトエートおよび3-トリエトキシシリル-1-プロピルチオオクトエートから成る群から選ばれる保護化メルカプトシラン。
- 保護化メルカプトシランが3-トリエトキシシリル-1-プロピルチオオクトエートである、請求項4に記載の保護化メルカプトシラン。
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DE102022203732A1 (de) | 2022-04-13 | 2023-10-19 | Continental Reifen Deutschland Gmbh | Verbindung, Kautschukmischung enthaltend die Verbindung, Fahrzeugreifen, der die Kautschukmischung in wenigstens einem Bauteil aufweist, Verfahren zur Herstellung der Verbindung sowie Verwendung der Verbindung als Alterungsschutzmittel und/oder Antioxidationsmittel |
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FR3144142A1 (fr) | 2022-12-21 | 2024-06-28 | Compagnie Generale Des Etablissements Michelin | Compositions elastomeriques comprenant un noir de carbone de pyrolyse |
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FR3146476A1 (fr) | 2023-03-09 | 2024-09-13 | Compagnie Generale Des Etablissements Michelin | Une composition de caoutchouc |
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1998
- 1998-08-21 EP EP98941025A patent/EP0958298B2/en not_active Expired - Lifetime
- 1998-08-21 CN CNB988015625A patent/CN100376585C/zh not_active Expired - Lifetime
- 1998-08-21 ES ES02019729.9T patent/ES2458563T3/es not_active Expired - Lifetime
- 1998-08-21 AU AU89179/98A patent/AU8917998A/en not_active Abandoned
- 1998-08-21 PT PT98941025T patent/PT958298E/pt unknown
- 1998-08-21 WO PCT/US1998/017391 patent/WO1999009036A1/en active IP Right Grant
- 1998-08-21 AT AT98941025T patent/ATE239737T1/de not_active IP Right Cessation
- 1998-08-21 KR KR1020067013055A patent/KR100825539B1/ko not_active IP Right Cessation
- 1998-08-21 US US09/284,841 patent/US6414061B1/en not_active Expired - Lifetime
- 1998-08-21 KR KR1019997003423A patent/KR100674059B1/ko not_active IP Right Cessation
- 1998-08-21 EP EP06004389A patent/EP1679315A1/en not_active Withdrawn
- 1998-08-21 ES ES98941025T patent/ES2199454T5/es not_active Expired - Lifetime
- 1998-08-21 JP JP51363999A patent/JP2001505225A/ja not_active Withdrawn
- 1998-08-21 EP EP02019729.9A patent/EP1270581B1/en not_active Expired - Lifetime
- 1998-08-21 DE DE69814353T patent/DE69814353T3/de not_active Expired - Lifetime
- 1998-08-21 CN CNA2007101424877A patent/CN101139355A/zh active Pending
- 1998-08-21 BR BRPI9806096-1A patent/BR9806096B1/pt not_active IP Right Cessation
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