TWI713652B - 含矽之偶氮二甲醯胺、其製備及用途 - Google Patents
含矽之偶氮二甲醯胺、其製備及用途 Download PDFInfo
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- TWI713652B TWI713652B TW105141441A TW105141441A TWI713652B TW I713652 B TWI713652 B TW I713652B TW 105141441 A TW105141441 A TW 105141441A TW 105141441 A TW105141441 A TW 105141441A TW I713652 B TWI713652 B TW I713652B
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- rubber
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- alk
- silicon
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- 229910052710 silicon Inorganic materials 0.000 title claims abstract description 34
- 239000010703 silicon Substances 0.000 title claims abstract description 34
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 238000002360 preparation method Methods 0.000 title abstract description 8
- 235000019399 azodicarbonamide Nutrition 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000013016 damping Methods 0.000 claims abstract description 4
- 229920001971 elastomer Polymers 0.000 claims description 75
- 239000005060 rubber Substances 0.000 claims description 74
- 239000000203 mixture Substances 0.000 claims description 52
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 26
- -1 chlorosulfonyl Chemical group 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 26
- 229920000570 polyether Polymers 0.000 claims description 26
- 229920000459 Nitrile rubber Polymers 0.000 claims description 23
- 229920002635 polyurethane Polymers 0.000 claims description 23
- 239000004814 polyurethane Substances 0.000 claims description 22
- 229920001577 copolymer Polymers 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 229920005549 butyl rubber Polymers 0.000 claims description 13
- 239000000945 filler Substances 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 229920000728 polyester Polymers 0.000 claims description 11
- 229920001169 thermoplastic Polymers 0.000 claims description 11
- 239000004416 thermosoftening plastic Substances 0.000 claims description 11
- 229920005557 bromobutyl Polymers 0.000 claims description 10
- 229920005556 chlorobutyl Polymers 0.000 claims description 10
- 239000005038 ethylene vinyl acetate Substances 0.000 claims description 10
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 claims description 10
- 229920003049 isoprene rubber Polymers 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 229920006168 hydrated nitrile rubber Polymers 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 229920002379 silicone rubber Polymers 0.000 claims description 6
- 239000004945 silicone rubber Substances 0.000 claims description 6
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 5
- 239000004698 Polyethylene Substances 0.000 claims description 5
- 150000002430 hydrocarbons Chemical group 0.000 claims description 5
- 229920000573 polyethylene Polymers 0.000 claims description 5
- 229920000642 polymer Polymers 0.000 claims description 5
- VHOQXEIFYTTXJU-UHFFFAOYSA-N Isobutylene-isoprene copolymer Chemical compound CC(C)=C.CC(=C)C=C VHOQXEIFYTTXJU-UHFFFAOYSA-N 0.000 claims description 4
- 229920000800 acrylic rubber Polymers 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- XOZUGNYVDXMRKW-AATRIKPKSA-N azodicarbonamide Chemical compound NC(=O)\N=N\C(N)=O XOZUGNYVDXMRKW-AATRIKPKSA-N 0.000 claims description 4
- 229920002493 poly(chlorotrifluoroethylene) Polymers 0.000 claims description 4
- 239000005023 polychlorotrifluoroethylene (PCTFE) polymer Substances 0.000 claims description 4
- 229920001195 polyisoprene Polymers 0.000 claims description 4
- 125000005248 alkyl aryloxy group Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- DMHFWNCPWYCBJI-UHFFFAOYSA-N 1-bromo-2-methylprop-1-ene;2-methylbuta-1,3-diene Chemical compound CC(C)=CBr.CC(=C)C=C DMHFWNCPWYCBJI-UHFFFAOYSA-N 0.000 claims description 2
- LVRSYEPLVIJQRJ-UHFFFAOYSA-N 3-bromo-2-methylprop-1-ene;2-methylbuta-1,3-diene Chemical compound CC(=C)CBr.CC(=C)C=C LVRSYEPLVIJQRJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000004709 Chlorinated polyethylene Substances 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229920002681 hypalon Polymers 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- HUGXNORHVOECNM-UHFFFAOYSA-N 3-chloro-2-methylprop-1-ene;2-methylbuta-1,3-diene Chemical compound CC(=C)CCl.CC(=C)C=C HUGXNORHVOECNM-UHFFFAOYSA-N 0.000 claims 1
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical class C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 32
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 24
- 239000003381 stabilizer Substances 0.000 description 21
- 239000000047 product Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 239000000377 silicon dioxide Substances 0.000 description 12
- 229910004298 SiO 2 Inorganic materials 0.000 description 11
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 10
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
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- 230000001476 alcoholic effect Effects 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 6
- 229920003048 styrene butadiene rubber Polymers 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 239000012300 argon atmosphere Substances 0.000 description 5
- 239000006229 carbon black Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
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- 238000002156 mixing Methods 0.000 description 5
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- 239000003921 oil Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Natural products CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000001354 calcination Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 229910000077 silane Inorganic materials 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- DKVNPHBNOWQYFE-UHFFFAOYSA-M carbamodithioate Chemical compound NC([S-])=S DKVNPHBNOWQYFE-UHFFFAOYSA-M 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
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- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 239000012990 dithiocarbamate Substances 0.000 description 3
- 239000003365 glass fiber Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 3
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- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
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- 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 description 3
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 3
- 229960002447 thiram Drugs 0.000 description 3
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 2
- FKMWAQFLTKJUHD-UHFFFAOYSA-N 1-chloro-2-methylprop-1-ene;2-methylbuta-1,3-diene Chemical compound CC(C)=CCl.CC(=C)C=C FKMWAQFLTKJUHD-UHFFFAOYSA-N 0.000 description 2
- CMGDVUCDZOBDNL-UHFFFAOYSA-N 4-methyl-2h-benzotriazole Chemical group CC1=CC=CC2=NNN=C12 CMGDVUCDZOBDNL-UHFFFAOYSA-N 0.000 description 2
- ZCFMGIGLXOKMJC-UHFFFAOYSA-N 5-butyl-2h-benzotriazole Chemical compound C1=C(CCCC)C=CC2=NNN=C21 ZCFMGIGLXOKMJC-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- 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
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- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- RDQQCSOIXMZZQR-UHFFFAOYSA-N [methyl(phenyl)carbamothioyl]sulfanyl n-methyl-n-phenylcarbamodithioate Chemical compound C=1C=CC=CC=1N(C)C(=S)SSC(=S)N(C)C1=CC=CC=C1 RDQQCSOIXMZZQR-UHFFFAOYSA-N 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
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- IWCRZZKSGBFRSJ-UHFFFAOYSA-N benzimidazol-1-ylmethanol Chemical compound C1=CC=C2N(CO)C=NC2=C1 IWCRZZKSGBFRSJ-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- QOTYLQBPNZRMNL-UHFFFAOYSA-N bis(2-methylpropyl)carbamothioylsulfanyl n,n-bis(2-methylpropyl)carbamodithioate Chemical compound CC(C)CN(CC(C)C)C(=S)SSC(=S)N(CC(C)C)CC(C)C QOTYLQBPNZRMNL-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
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- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- PGAXJQVAHDTGBB-UHFFFAOYSA-N dibutylcarbamothioylsulfanyl n,n-dibutylcarbamodithioate Chemical compound CCCCN(CCCC)C(=S)SSC(=S)N(CCCC)CCCC PGAXJQVAHDTGBB-UHFFFAOYSA-N 0.000 description 2
- REQPQFUJGGOFQL-UHFFFAOYSA-N dimethylcarbamothioyl n,n-dimethylcarbamodithioate Chemical compound CN(C)C(=S)SC(=S)N(C)C REQPQFUJGGOFQL-UHFFFAOYSA-N 0.000 description 2
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- 238000005516 engineering process Methods 0.000 description 2
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 2
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- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
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- 238000004073 vulcanization Methods 0.000 description 2
- BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- UDYXMTORTDACTG-UHFFFAOYSA-N 1,1,3-tributylthiourea Chemical compound CCCCNC(=S)N(CCCC)CCCC UDYXMTORTDACTG-UHFFFAOYSA-N 0.000 description 1
- UDWCKMMKPOGURO-UHFFFAOYSA-N 1,2-dihydropyrazolo[3,4-b]pyridin-4-one Chemical compound O=C1C=CNC2=C1C=NN2 UDWCKMMKPOGURO-UHFFFAOYSA-N 0.000 description 1
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- C07F7/02—Silicon compounds
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- 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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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- 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
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
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- C—CHEMISTRY; METALLURGY
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- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
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Abstract
本發明關於通式I的含矽之偶氮二甲醯胺(A1)x(A2)(3-x)Si-R1-N(D1)-CO-N=N-CO-N(D1)-R1-Si(A1)x(A2)(3-x) (I)。
該通式I的含矽之偶氮二甲醯胺係藉由下列反應而製得：將通式II的偶氮二羧基化合物Sub1-X1-C(O)-N=N-C(O)-X2-Sub2 (II)與通式III的胺基矽烷反應(A1)x(A2)(3-x)Si-R1-N(D1)H (III)。
該通式I的含矽之偶氮二甲醯胺可用於電纜護套、軟管、傳動帶、輸送帶、捲筒覆蓋物、鞋襪底、環封和阻尼元件。
Description
本發明關於含矽之偶氮二甲醯胺(silicon-containing azodicarboxamide)、與其製備及在橡膠混合物中的用途。
DE 2704506揭示通式Y-X-CO-N=N-CO-X1-Z的化合物及其在含填料之橡膠混合物中的用途。
此外，US 20090234066 A1揭示式A-CO-N=N-CO-Z-G的化合物，其與含硫之矽烷一起用於包含異戊二烯橡膠之橡膠混合物中。
US 20090186961 A1揭示式A-CO-N=N-CO-Z-G的化合物，其與〝塗佈材料〞一起用於包含異戊二烯橡膠之橡膠混合物中。
此外，EP 2508559揭示包含下列之橡膠混合物：
(A)至少一種選自下列群組之橡膠：乙烯-丙烯-二烯共聚物(EPDM)、乙烯-丙烯共聚物(EPM)、氯平橡膠(chloroprene rubber)(CR)、氯化聚乙烯(chloropolyethylene)(CM)、氯異丁烯-異戊二烯
(chloroisobutene-isoprene)(氯化丁基)橡膠(CIIR)、氯磺醯基聚乙烯(chlorosulphonyl-polyethylene)(CSM)、乙烯-乙酸乙烯酯共聚物(EAM)、丙烯酸烷酯共聚物(ACM)、聚酯聚胺甲酸酯(polyester polyurethane)(AU)、聚醚聚胺甲酸酯(polyether polyurethane)(EU)、溴異丁烯-異戊二烯(bromoisobutene-isoprene)(溴化丁基)橡膠(BIIR)、聚氯三氟乙烯(CFM)、異丁烯-異戊二烯橡膠(isobutene-isoprene rubber)(丁基橡膠，IIR)、異丁烯橡膠(IM)、熱塑性聚酯聚胺甲酸酯(YAU)、熱塑性聚醚聚胺甲酸酯(YEU)、在聚合物鏈上具有甲基之矽氧橡膠(silicone rubber)(MQ)、氫化丙烯腈-丁二烯橡膠(hydrogenated acrylonitrile-butadiene rubber)(HNBR)、丙烯腈-丁二烯橡膠(NBR)或羧酸化丙烯腈-丁二烯橡膠(carboxylated acrylonitrile-butadiene rubber)(XNBR)，(B)至少一種氧化物填料，以及(C)至少一種式(R1)3-a(R2)aSi-RI-NH-C(O)-N=N-C(O)-NH-RI-Si(R1)3-a(R2)a的含矽之偶氮雙脲(azodicarbamide)。
EP 2552925揭示製備下式的含矽之偶氮雙脲之方法(R1)3-a(R2)aSi-R1-NH-C(O)-N=N-C(O)-NH-R1-Si(R1)3-a(R2)a，
其係藉由將下式之偶氮雙羧基化合物(azobiscarboxy compound)
R3-X1-C(O)-N=N-C(O)-X1-R4
與下式之胺基矽烷反應(R1)3-a(R2)aSi-R1-NH2。
本發明的一目的係提供適合於含填料之橡膠混合物的不含硫之偶合試劑，該混合物展現改進之模量(modulus)300、δ轉矩(delta torque)及抗撕裂性(tear resistance)。
本發明提供通式I的含矽之偶氮二甲醯胺(A1)x(A2)(3-x)Si-R1-N(D1)-CO-N=N-CO-N(D1)-R1-Si(A1)x(A2)(3-x) (I)，其中A1為烷基聚醚基團-O-((CRI 2)w-O-)v-Alk，較佳為-O-(CH2-CH2-O-)v-Alk或-O-(CH(CH3)-CH2-O-)v-Alk，其中v=1-60、較佳為2-30、更佳為2-20、且非常佳為2-15、極佳為3-10，w=1-20、較佳為2-10、更佳為2-5、非常佳為2，RI在各情況下獨立為H、苯基或非支鏈或支鏈(較佳為C1-C11，更佳為CH3或CH2-CH3)烷基，Alk為支鏈或非支鏈、飽和或不飽和、經取代或未經
取代之脂族、芳族或混合型脂族/芳族單價C1-C35(較佳為C2-C22、更佳為C3-C18、最佳為C5-C13)烴基，A2為相同或不同且為支鏈或非支鏈烷基，較佳為C1-C18烷基，更佳為CH3、CH2-CH3、CH(CH3)-CH3、CH2-CH2-CH3或C4-C14烷基，最佳為CH3，支鏈或非支鏈烷氧基，較佳為C1-C18烷氧基，更佳為-OCH3、-OCH2-CH3、-OCH(CH3)-CH3、-OCH2-CH2-CH3、-OC12H25、-OC13H27、-OC14H29或C15-C18烷氧基，最佳為-OCH2CH3，支鏈或非支鏈C2-C25烯氧基，較佳為C4-C20烯氧基，更佳為C6-C18烯氧基，C6-C35芳氧基，較佳為C9-C30芳氧基，更佳為苯氧基(-OC6H5)或C9-C18芳氧基，支鏈或非支鏈C7-C35烷基芳氧基，較佳為C9-C30烷基芳氧基，更佳為苄氧基(benzyloxy)(-O-CH2-C6H5)或-O-CH2-CH2-C6H5，支鏈或非支鏈C7-C35芳烷氧基，較佳為C7-C25芳烷氧基，更佳為甲苯氧基(-O-C6H4-CH3)或C9-C18芳烷氧基，或羥基(-OH)，D1為相同或不同且為H或Alk’，較佳為-H或-C4H9，其中Alk’為C1-C18(較佳為C1-C10、更佳為C1-C5、最佳為C1-C3)烷基，C5-C18(較佳為C6)環烷基，或C6-C18芳基(較佳為苯基)，
R1為相同或不同且為支鏈或非支鏈、飽和或不飽和之脂族、芳族或混合型脂族/芳族二價C1-C30(較佳為C1-C20、更佳為C1-C15、最佳為C1-C8)烴基，其隨意地(optionally)經F-、Cl-、Br-、I-、-CN或HS-取代，其特徵在於平均聚醚分率(average polyether fraction)x=1.3-1.7，較佳為1.4-1.6。
含矽之偶氮二甲醯胺可為通式I的含矽之偶氮二甲醯胺的混合物。
通式I的含矽之偶氮二甲醯胺可經歷烷氧基矽烷官能基(alkoxysilane function)的水解(hydrolysis)及縮合(condensation)，以形成通式I的含矽之偶氮二甲醯胺的含矽氧烷之寡聚物(siloxane-containing oligomer)。
平均聚醚分率x係根據以下公式計算：
其中M(SiO2)為SiO2之莫耳質量(60.08克/莫耳)，w%(SiO2)為根據下述方法所測定之SiO2的量。上述公式係基於以下假設：
莫耳質量M係由如下組成：M=1011.5(x-1)+636.9(2-x)。此1011.5為下列具有x=2
的參考化合物之平均莫耳質量的一半：[(C13H27(-O-CH2-CH2)5-O-)2.0(EtO)1.0Si-(CH2)3-NH-C(=O)-N=]2，及636.9為下列具有x=1的參考化合物之平均莫耳質量的一半：[(C13H27(-O-CH2-CH2)5-O-)1.0(EtO)2.0Si-(CH2)3-NH-C(=O)-N=]2。
w%(SiO2)的測定：該方法說明藉由以氫氟酸加熱進行二氧化矽之重量測定。
將用於分析之0.2克樣品秤至鉑坩堝(platinum crucible)中。添加10滴濃硫酸，且將坩堝以配件蓋(fitting lid)密閉且在熱板(hotplate)上加熱。添加1毫升濃硝酸及10滴30%之過氧化氫，且將坩堝再以蓋密封。在熱板上於坩堝中進行氧化，重複添加硝酸及過氧化氫，直到坩堝中出現白色殘餘物為止。將坩堝的內容物以Bunsen燃燒器蒸發、排出氣體及煅燒(calcine)。煅燒操作係接著在套爐(muffle furnace)中以1000℃發生1小時。將樣品在乾燥器中冷卻且隨後秤重。
添加數滴硫酸及至多5毫升40%之氫氟酸。進行蒸發及排出氣體，直到不再有硫酸蒸氣出現為止。重複以氫氟酸加熱的步驟。煅燒最初以Bunsen燃燒器進行及接著在
套爐中以1000℃進行1小時。將樣品在乾燥器中冷卻且秤重。
SiO2含量之計算：
m1=以氫氟酸加熱之後的坩堝與煅燒殘餘物之質量，以克計
m2=以氫氟酸加熱之前的坩堝與煅燒殘餘物之質量，以克計
E=樣品初始質量，以克計
Alk較佳地可為-CH3、-CH2-CH3、-C3H7、-C4H9、-C5H11、-C6H13、-C7H15、-C8H17、-C9H19、-C10H21、-C11H23、-C12H25、-C13H27、-C14H29、-C15H31、-C16H33、-C17H35、-C18H37或-C19H39。
R1較佳地可為-CH2-、-CH2CH2-、-CH2CH2CH2-、-CH2CH2CH2CH2-、-CH(CH3)-、-CH2CH(CH3)-、-CH(CH3)CH2-、-C(CH3)2-、-CH(C2H5)-、-CH2CH2CH(CH3)-、-CH(CH3)CH2CH2-、-CH2CH(CH3)CH2-、-CH2CH2CH2CH2CH2-、-CH2CH2CH2CH2CH2CH2-、-CH2CH2CH2CH2CH2CH2CH2-、-CH2CH2CH2CH2CH2CH2CH2CH2-、-CH2CH2CH2CH2CH2CH2CH2CH2CH2-、-CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2-、
-CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2-、-CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2-、-CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2-、-CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2-或-CH2-CH2-C6H4-CH2-。
A1之烷基聚醚基團(alkyl polyether group)的基團((CRI 2)w-O-)可為環氧乙烷(CH2-CH2-O)、環氧丙烷例如(CH(CH3)-CH2-O)或(CH2-CH(CH3)-O)、或環氧丁烷單元例如(-CH2-CH2-CH2-CH2-O)、(-CH(CH2-CH3)-CH2-O)或(-CH2-CH(CH2-CH3)-O)。
基團-O-((CRI 2)w-O-)v較佳地可為：O-(-CH2-CH2-O-)a、O-(-CH(CH3)-CH2-O-)a、O-(-CH2-CH(CH3)-O-)a、O-(-CH2-CH2-O-)a(-CH(CH3)-CH2-O-)、O-(-CH2-CH2-O-)(-CH(CH3)-CH2-O-)a、O-(-CH2-CH2-O-)a(-CH2-CH(CH3)-O-)、O-(-CH2-CH2-O-)(-CH2-CH(CH3)-O-)a、O-(-CH(CH3)-CH2-O-)a(-CH2-CH(CH3)-O-)、O-(-CH(CH3)-CH2-O-)(-CH2-CH(CH3)-O-)a、O-(-CH2-CH2-O-)a(-CH(CH3)-CH2-O-)b(-CH2-CH(CH3)-O-)c或彼此之組合。
下標a、b和c為整數且代表重複單元的數目。下標a、b和c可為1-20，較佳為1至15，更佳為1至8，最
佳為1至5。
具有-O-((CRI 2)w-O-)vAlk之烷基聚醚基團A1可為O-(CH2-CH2O)2-CH3、O-(CH2-CH2O)3-CH3、O-(CH2-CH2O)4-CH3、O-(CH2-CH2O)5-CH3、O-(CH2-CH2O)6-CH3、O-(CH2-CH2O)7-CH3、O-(CH(CH3)-CH2O)2-CH3、O-(CH(CH3)-CH2O)3-CH3、O-(CH(CH3)-CH2O)4-CH3、O-(CH(CH3)-CH2O)5-CH3、O-(CH(CH3)-CH2O)6-CH3、O-(CH2-CH2O)2-CH2-CH3、O-(CH2-CH2O)3-CH2-CH3、O-(CH2-CH2O)4-CH2-CH3、O-(CH2-CH2O)5-CH2-CH3、O-(CH2-CH2O)6-CH2-CH3、O-(CH2-CH2O)7-CH2-CH3、O-(CH(CH3)-CH2O)2-CH3、O-(CH(CH3)-CH2O)3-CH3、O-(CH(CH3)-CH2O)4-CH3、O-(CH(CH3)-CH2O)5-CH3、O-(CH(CH3)-CH2O)6-CH3、O-(CH2-CH2O)2-C3H7、O-(CH2-CH2O)3-C3H7、O-(CH2-CH2O)4-C3H7、O-(CH2-CH2O)5-C3H7、O-(CH2-CH2O)6-C3H7、O-(CH2-CH2O)7-C3H7、O-(CH(CH3)-CH2O)2-C3H7、O-(CH(CH3)-CH2O)3-C3H7、O-(CH(CH3)-CH2O)4-C3H7、O-(CH(CH3)-CH2O)5-C3H7、O-(CH(CH3)-CH2O)6-C3H7、O-(CH2-CH2O)2-C4H9、O-(CH2-CH2O)3-C4H9、O-(CH2-CH2O)4-C4H9、O-(CH2-CH2O)5-C4H9、O-(CH2-CH2O)6-C4H9、O-(CH2-CH2O)7-C4H9、O-(CH(CH3)-CH2O)2-C4H9、O-(CH(CH3)-CH2O)3-C4H9、O-(CH(CH3)-CH2O)4-C4H9、O-(CH(CH3)-CH2O)5-C4H9、O-(CH(CH3)-CH2O)6-C4H9、O-(CH2-CH2O)2-C5H11、
O-(CH2-CH2O)3-C5H11、O-(CH2-CH2O)4-C5H11、O-(CH2-CH2O)5-C5H11、O-(CH2-CH2O)6-C5H11、O-(CH2-CH2O)7-C5H11、O-(CH(CH3)-CH2O)2-C5H11、O-(CH(CH3)-CH2O)3-C5H11、O-(CH(CH3)-CH2O)4-C5H11、O-(CH(CH3)-CH2O)5-C5H11、O-(CH(CH3)-CH2O)6-C5H11、O-(CH2-CH2O)2-C6H13、O-(CH2-CH2O)3-C6H13、O-(CH2-CH2O)4-C6H13、O-(CH2-CH2O)5-C6H13、O-(CH2-CH2O)6-C6H13、O-(CH2-CH2O)7-C6H13、O-(CH(CH3)-CH2O)2-C6H13、O-(CH(CH3)-CH2O)3-C6H13、O-(CH(CH3)-CH2O)4-C6H13、O-(CH(CH3)-CH2O)5-C6H13、O-(CH(CH3)-CH2O)6-C6H13、O-(CH2-CH2O)2-C7H15、O-(CH2-CH2O)3-C7H15、O-(CH2-CH2O)4-C7H15、O-(CH2-CH2O)5-C7H15、O-(CH2-CH2O)6-C7H15、O-(CH2-CH2O)7-C7H15、O-(CH(CH3)-CH2O)2-C7H15、O-(CH(CH3)-CH2O)3-C7H15、O-(CH(CH3)-CH2O)4-C7H15、O-(CH(CH3)-CH2O)5-C7H15、O-(CH(CH3)-CH2O)6-C7H15、O-(CH2-CH2O)2-C8H17、O-(CH2-CH2O)3-C8H17、O-(CH2-CH2O)4-C8H17、O-(CH2-CH2O)5-C8H17、O-(CH2-CH2O)6-C8H17、O-(CH2-CH2O)7-C8H17、O-(CH(CH3)-CH2O)2-C8H17、O-(CH(CH3)-CH2O)3-C8H17、O-(CH(CH3)-CH2O)4-C8H17、O-(CH(CH3)-CH2O)5-C8H17、O-(CH(CH3)-CH2O)6-C8H17、O-(CH2-CH2O)2-C9H19、O-(CH2-CH2O)3-C9H19、O-(CH2-CH2O)4-C9H19、O-(CH2-CH2O)5-C9H19、O-(CH2-CH2O)6-C9H19、
O-(CH2-CH2O)7-C9H19、O-(CH(CH3)-CH2O)2-C9H19、O-(CH(CH3)-CH2O)3-C9H19、O-(CH(CH3)-CH2O)4-C9H19、O-(CH(CH3)-CH2O)5-C9H19、O-(CH(CH3)-CH2O)6-C9H19、O-(CH2-CH2O)2-C10H21、O-(CH2-CH2O)2-C10H21、O-(CH2-CH2O)4-C10H21、O-(CH2-CH2O)5-C10H21、O-(CH2-CH2O)6-C10H21、O-(CH2-CH2O)7-C10H21、O-(CH(CH3)-CH2O)2-C10H21、O-(CH(CH3)-CH2O)3-C10H21、O-(CH(CH3)-CH2O)4-C10H21、O-(CH(CH3)-CH2O)5-C10H21、O-(CH(CH3)-CH2O)6-C10H21、O-(CH2-CH2O)2-C11H23、O-(CH2-CH2O)3-C11H23、O-(CH2-CH2O)4-C11H23、O-(CH2-CH2O)5-C11H23、O-(CH2-CH2O)6-C11H23、O-(CH2-CH2O)7-C11H23、O-(CH(CH3)-CH2O)2-C11H23、O-(CH(CH3)-CH2O)3-C11H23、O-(CH(CH3)-CH2O)4-C11H23、O-(CH(CH3)-CH2O)5-C11H23、O-(CH(CH3)-CH2O)6-C11H23、O-(CH2-CH2O)2-C12H25、O-(CH2-CH2O)3-C12H25、O-(CH2-CH2O)4-C12H25、O-(CH2-CH2O)5-C12H25、O-(CH2-CH2O)6-C12H25、O-(CH2-CH2O)7-C12H25、O-(CH(CH3)-CH2O)2-C12H25、O-(CH(CH3)-CH2O)3-C12H25、O-(CH(CH3)-CH2O)4-C12H25、O-(CH(CH3)-CH2O)5-C12H25、O-(CH2-CH2O)2-C13H27、O-(CH2-CH2O)3-C13H27、O-(CH2-CH2O)4-C13H27、O-(CH2-CH2O)5-C13H27、O-(CH2-CH2O)6-C13H27、O-(CH2-CH2O)7-C13H27、O-(CH(CH3)-CH2O)2-C13H27、O-(CH(CH3)-CH2O)3-
C13H27、O-(CH(CH3)-CH2O)4-C13H27、O-(CH(CH3)-CH2O)5-C13H27、O-(CH2-CH2O)2-C14H29、O-(CH2-CH2O)3-C14H29、O-(CH2-CH2O)4-C14H29、O-(CH2-CH2O)5-C14H29、O-(CH2-CH2O)6-C14H29、O-(CH2-CH2O)7-C14H29、O-(CH(CH3)-CH2O)2-C14H29、O-(CH(CH3)-CH2O)3-C14H29、O-(CH(CH3)-CH2O)4-C14H29、O-(CH(CH3)-CH2O)5-C14H29、O-(CH2-CH2O)2-C15H31、O-(CH2-CH2O)3-C15H31、O-(CH2-CH2O)4-C15H31、O-(CH2-CH2O)5-C15H31、O-(CH2-CH2O)6-C15H31、O-(CH2-CH2O)7-C15H31、O-(CH(CH3)-CH2O)2-C15H31、O-(CH(CH3)-CH2O)3-C15H31、O-(CH(CH3)-CH2O)4-C15H31、O-(CH2-CH2O)2-C16H33、O-(CH2-CH2O)3-C16H33、O-(CH2-CH2O)4-C16H33、O-(CH2-CH2O)5-C16H33、O-(CH2-CH2O)6-C16H33、O-(CH(CH3)-CH2O)2-C16H33、O-(CH(CH3)-CH2O)3-C16H33、O-(CH(CH3)-CH2O)4-C16H33、O-(CH2-CH2O)2-C17H35、O-(CH2-CH2O)3-C17H35、O-(CH2-CH2O)4-C17H35、O-(CH2-CH2O)5-C17H35、O-(CH2-CH2O)6-C17H35、O-(CH(CH3)-CH2O)2-C17H35、O-(CH(CH3)-CH2O)3-C17H35、O-(CH(CH3)-CH2O)4-C17H35、O-(CH(CH3)-CH2O)5-C17H35、O-(CH2-CH2O)2-C18H37、O-(CH2-CH2O)3-C18H37、O-(CH2-CH2O)4-C18H37、O-(CH2-CH2O)5-C18H37、C18H37、O-(CH2-CH2O)6-C18H37、O-(CH(CH3)-CH2O)2-C18H37、O-(CH(CH3)-CH2O)3-C18H37、O-(CH(CH3)-CH2O)4-C18H37、O-(CH(CH3)-
CH2O)5-C18H37、O-(CH2-CH2O)2-C6H4-C9H19、O-(CH2-CH2O)3-C6H4-C9H19、O-(CH2-CH2O)4-C6H4-C9H19、O-(CH2-CH2O)5-C6H4-C9H19、O-(CH2-CH2O)6-C6H4-C9H19、O-(CH2-CH2O)7-C6H4-C9H19、O-(CH(CH3)-CH2O)2-C6H4-C9H19、O-(CH(CH3)-CH2O)3-C6H4-C9H19或O-(CH(CH3)-CH2O)4-C6H4-C9H19。
v=5、RI=H及Alk=C13H27的具有-O-((CRI 2)w-O-)vAlk之烷基聚醚基團A1可為
或
碳鏈Alk之平均支鏈數目(average branching number)可為1至5，較佳為1、2、3或4。平均支鏈數目在此係定義為(CH3基團數目)-1。
其中A1為v=1至40(較佳為v=1至30，更佳為v=1至15)的烷基聚醚基團-O-((CRI 2)w-O-)v Alk(較佳為-
O-(CH2-CH2-O-)v Alk)之通式I的化合物可為下列者：[(C11H23O-(CH2-CH2O)v]x(EtO)(3-x)Si-CH2-NH-CO-N=N-CO-NH-CH2-Si(OEt)(3-x)[O-(CH2-CH2O)v-C11H23]x、[(C12H25O-(CH2-CH2O)V]x(EtO)(3-x)Si-CH2-NH-CO-N=N-CO-NH-CH2-Si(OEt)(3-x)[O-(CH2-CH2O)v-C12H25]x、[(C13H27O-(CH2-CH2O)V]x(EtO)(3-x)Si-CH2-NH-CO-N=N-CO-NH-CH2-Si(OEt)(3-x)[O-(CH2-CH2O)v-C13H27]x、[(C14H29O-(CH2-CH2O)V]x(EtO)(3-x)Si-CH2-NH-CO-N=N-CO-NH-CH2-Si(OEt)(3-x)[O-(CH2-CH2O)v-C14H29]x、[(C15H31O-(CH2-CH2O)V]x(EtO)(3-x)Si-CH2-NH-CO-N=N-CO-NH-CH2-Si(OEt)(3-x)[O-(CH2-CH2O)v-C15H31]x、[(C16H33O-(CH2-CH2O)V]x(EtO)(3-x)Si-CH2-NH-CO-N=N-CO-NH-CH2-Si(OEt)(3-x)[O-(CH2-CH2O)v-C16H33]x、[(C17H35O-(CH2-CH2O)V]x(EtO)(3-x)Si-CH2-NH-CO-N=N-CO-NH-CH2-Si(OEt)(3-x)[O-(CH2-CH2O)v-C17H35]x、[(C18H37O-(CH2-CH2O)V]x(EtO)(3-x)Si-CH2-NH-CO-N=N-CO-NH-CH2-Si(OEt)(3-x)[O-(CH2-CH2O)v-C18H37]x、[(C11H23O-(CH2-CH2O)v]x(EtO)(3-x)Si-CH2-CH2-NH-CO-N=N-CO-NH-CH2-CH2-Si(OEt)(3-x)[O-(CH2-CH2O)v-C11H23]x、[(C12H25O-(CH2-CH2O)v]x(EtO)(3-x)Si-CH2-CH2-NH-CO-N=N-CO-NH-CH2-CH2-Si(OEt)(3-x)[O-(CH2-CH2O)v-C12H25]x、[(C13H27O-(CH2-CH2O)v]x(EtO)(3-x)Si-CH2-CH2-NH-
CO-N=N-CO-NH-CH2-CH2-Si(OEt)(3-x)[O-(CH2-CH2O)v-C13H27]x、[(C14H29O-(CH2-CH2O)v]x(EtO)(3-x)Si-CH2-CH2-NH-CO-N=N-CO-NH-CH2-CH2-Si(OEt)(3-x)[O-(CH2-CH2O)v-C14H29]x、[(C15H31O-(CH2-CH2O)v]x(EtO)(3-x)Si-CH2-CH2-NH-CO-N=N-CO-NH-CH2-CH2-Si(OEt)(3-x)[O-(CH2-CH2O)v-C15H31]x、[(C16H33O-(CH2-CH2O)v]x(EtO)(3-x)Si-CH2-CH2-NH-CO-N=N-CO-NH-CH2-CH2-Si(OEt)(3-x)[O-(CH2-CH2O)v-C16H33]x、[(C17H35O-(CH2-CH2O)v]x(EtO)(3-x)Si-CH2-CH2-NH-CO-N=N-CO-NH-CH2-CH2-Si(OEt)(3-x)[O-(CH2-CH2O)v-C17H35]x、[(C18H37O-(CH2-CH2O)v]x(EtO)(3-x)Si-CH2-CH2-NH-CO-N=N-CO-NH-CH2-CH2-Si(OEt)(3-x)[O-(CH2-CH2O)v-C18H37]x、[(C11H23O-(CH2-CH2O)v]x(EtO)(3-x)Si-CH2-CH2-CH2-NH-CO-N=N-CO-NH-CH2-CH2-CH2-Si(OEt)(3-x)[O-(CH2-CH2O)v-C11H23]x、[(C12H25O-(CH2-CH2O)v]x(EtO)(3-x)Si-CH2-CH2-CH2-NH-CO-N=N-CO-NH-CH2-CH2-CH2-Si(OEt)(3-x)[O-(CH2-CH2O)v-C12H25]x、[(C13H27O-(CH2-CH2O)v]x(EtO)(3-x)Si-CH2-CH2-CH2-
NH-CO-N=N-CO-NH-CH2-CH2-CH2-Si(OEt)(3-x)[O-(CH2-CH2O)v-C13H27]x、[(C14H29O-(CH2-CH2O)v]x(EtO)(3-x)Si-CH2-CH2-CH2-NH-CO-N=N-CO-NH-CH2-CH2-CH2-Si(OEt)(3-x)[O-(CH2-CH2O)v-C14H29]x、[(C15H31O-(CH2-CH2O)v]x(EtO)(3-x)Si-CH2-CH2-CH2-NH-CO-N=N-CO-NH-CH2-CH2-CH2-Si(OEt)(3-x)[O-(CH2-CH2O)v-C15H31]x、[(C16H33O-(CH2-CH2O)v]x(EtO)(3-x)Si-CH2-CH2-CH2-NH-CO-N=N-CO-NH-CH2-CH2-CH2-Si(OEt)(3-x)[O-(CH2-CH2O)v-C16H33]x、[(C17H35O-(CH2-CH2O)v]x(EtO)(3-x)Si-CH2-CH2-CH2-NH-CO-N=N-CO-NH-CH2-CH2-CH2-Si(OEt)(3-x)[O-(CH2-CH2O)v-C17H35]x、[(C18H37O-(CH2-CH2O)v]x(EtO)(3-x)Si-CH2-CH2-CH2-NH-CO-N=N-CO-NH-CH2-CH2-CH2-Si(OEt)(3-x)[O-(CH2-CH2O)v-C18H37]x、[(C11H23O-(CH2-CH2O)v]x(CH3)(3-x)Si-CH2-NH-CO-N=N-CO-NH-CH2-Si(CH3)(3-x)[O-(CH2-CH2O)v-C11H23]x、[(C12H25O-(CH2-CH2O)v]x(CH3)(3-x)Si-CH2-NH-CO-N=N-CO-NH-CH2-Si(CH3)(3-x)[O-(CH2-CH2O)v-C12H25]x、[(C13H27O-(CH2-CH2O)v]x(CH3)(3-x)Si-CH2-NH-CO-N=N-CO-NH-CH2-Si(CH3)(3-x)[O-(CH2-CH2O)v-C13H27]x、[(C14H29O-(CH2-CH2O)v]x(CH3)(3-x)Si-CH2-NH-CO-
N=N-CO-NH-CH2-Si(CH3)(3-x)[O-(CH2-CH2O)v-C14H29]x、[(C15H31O-(CH2-CH2O)v]x(CH3)(3-x)Si-CH2-NH-CO-N=N-CO-NH-CH2-Si(CH3)(3-x)[O-(CH2-CH2O)v-C15H31]x、[(C16H33O-(CH2-CH2O)v]x(CH3)(3-x)Si-CH2-NH-CO-N=N-CO-NH-CH2-Si(CH3)(3-x)[O-(CH2-CH2O)v-C16H33]x、[(C17H35O-(CH2-CH2O)v]x(CH3)(3-x)Si-CH2-NH-CO-N=N-CO-NH-CH2-Si(CH3)(3-x)[O-(CH2-CH2O)v-C17H35]x、[(C18H37O-(CH2-CH2O)v]x(CH3)(3-x)Si-CH2-NH-CO-N=N-CO-NH-CH2-Si(CH3)(3-x)[O-(CH2-CH2O)v-C18H37]x、[(C11H23O-(CH2-CH2O)v]x(CH3)(3-x)Si-CH2-CH2-CH2-NH-CO-N=N-CO-NH-CH2-CH2-CH2-Si(CH3)(3-x)[O-(CH2-CH2O)v-C11H23]x、[(C12H25O-(CH2-CH2O)v]x(CH3)(3-x)Si-CH2-CH2-CH2-NH-CO-N=N-CO-NH-CH2-CH2-CH2-Si(CH3)(3-x)[O-(CH2-CH2O)v-C12H25]x、[(C13H27O-(CH2-CH2O)v]x(CH3)(3-x)Si-CH2-CH2-CH2-NH-CO-N=N-CO-NH-CH2-CH2-CH2-Si(CH3)(3-x)[O-(CH2-CH2O)v-C13H27]x、[(C14H29O-(CH2-CH2O)v]x(CH3)(3-x)Si-CH2-CH2-CH2-NH-CO-N=N-CO-NH-CH2-CH2-CH2-Si(CH3)(3-x)[O-(CH2-CH2O)v-C14H29]x、[(C15H31O-(CH2-CH2O)v]x(CH3)(3-x)Si-CH2-CH2-CH2-NH-CO-N=N-CO-NH-CH2-CH2-CH2-Si(CH3)(3-x)[O-(CH2-CH2O)v-C15H31]x、
[(C16H33O-(CH2-CH2O)v]x(CH3)(3-x)Si-CH2-CH2-CH2-NH-CO-N=N-CO-NH-CH2-CH2-CH2-Si(CH3)(3-x)[O-(CH2-CH2O)v-C16H33]x、[(C17H35O-(CH2-CH2O)v]x(CH3)(3-x)Si-CH2-CH2-CH2-NH-CO-N=N-CO-NH-CH2-CH2-CH2-Si(CH3)(3-x)[O-(CH2-CH2O)v-C17H35]x、[(C18H37O-(CH2-CH2O)v]x(CH3)(3-x)Si-CH2-CH2-CH2-NH-CO-N=N-CO-NH-CH2-CH2-CH2-Si(CH3)(3-x)[O-(CH2-CH2O)v-C18H37]x。
在較佳的通式I的含矽之偶氮二甲醯胺中，基團A1可為-O-((CH2)w-O-)5 C13H27。
通式I的含矽之偶氮二甲醯胺可為下式的含矽之偶氮二甲醯胺：[(C13H27(-O-CH2-CH2)5-O-)1.5(EtO)1.5 Si-(CH2)3-NH-C(=O)-N=]2、[(C13H27(-O-CH2-CH2)5-O-)1.3(EtO)1.7 Si-(CH2)3-NH-C(=O)-N=]2、[(C13H27(-O-CH2-CH2)5-O-)1.4(EtO)1.6 Si-(CH2)3-NH-C(=O)-N=]2、[(C13H27(-O-CH2-CH2)5-O-)1.7(EtO)1.3 Si-(CH2)3-NH-C(=O)-N=]2或[(C13H27(-O-CH2-CH2)5-O-)1.6(EtO)1.4 Si-(CH2)3-NH-C(=O)-N=]2。
本發明進一步提供製備通式I的含矽之偶氮二甲醯胺的方法(A1)x(A2)(3-x)Si-R1-N(D1)-CO-N=N-CO-N(D1)-R1-Si(A1)x(A2)(3-x) (I)，
其特徵在於將通式II的偶氮二羧基化合物Sub1-X1-C(O)-N=N-C(O)-X2-Sub2 (II)
與通式III的胺基矽烷反應(A1)x(A2)(3-x)Si-R1-N(D1)H (III)
其中x、A1、A2、R1和D1具有上文所述之定義，及Sub1和Sub2為相同或不同且為H、C1-C18支鏈或非支鏈烷基，較佳為C3-C12支鏈或非支鏈烷基，較佳為乙基、丙基或異丙基，苄基(-CH2-C6H5)或烷基聚醚(CH2-CH2-O)n-Alk’或(CH(CH3)-CH2-O)n-Alk’，其中n為1至10，較佳為1至8，更佳為1至5，且最佳為1至3，及Alk’具有上文所述之定義，X1和X2為相同或不同且為O或NH。
用作為反應物之通式II的偶氮二羧基化合物可為通式的偶氮二羧基化合物之混合物。
用作為反應物之通式III的胺基矽烷可為通式III的胺基矽烷之混合物。
通式III的胺基矽烷可經歷烷氧基矽烷官能基之水解及縮合，以形成通式III的胺基矽烷之含矽氧烷之寡聚物。
通式III的胺基矽烷可藉由將胺基矽烷(A2)3Si-R1-
N(D1)H與烷基聚醚A1-H以所欲莫耳比進行轉酯化(transesterifying)而製得。
通式II的化合物較佳地可為：烷基-HN-CO-N=N-CO-NH-烷基，例如甲基-HN-CO-N=N-CO-NH-甲基、乙基-HN-CO-N=N-CO-NH-乙基、正丙基-HN-CO-N=N-CO-NH-正丙基、異丙基-HN-CO-N=N-CO-NH-異丙基、正丁基-HN-CO-N=N-CO-NH-正丁基、二級丁基-HN-CO-N=N-CO-NH-二級丁基、三級丁基-HN-CO-N=N-CO-NH-三級丁基、苄基-HN-CO-N=N-CO-NH-苄基或苯基-HN-CO-N=N-CO-NH-苯基。
基本形式烷基-O-C(O)-N=N-C(O)-O-烷基之通式II的化合物較佳地可為：乙基-O-C(O)-N=N-C(O)-O-乙基、丙基-O-C(O)-N=N-C(O)-O-丙基、異丙基-O-C(O)-N=N-C(O)-O-異丙基、正丁基-O-C(O)-N=N-C(O)-O-正丁基、三級丁基-O-C(O)-N=N-C(O)-O-三級丁基、二級丁基-O-C(O)-N=N-C(O)-O-二級丁基、環己基-O-C(O)-N=N-C(O)-O-環己基或苄基-O-C(O)-N=N-C(O)-O-苄基。
其中n=1至10的基本結構Alk’-(O-CH2-CH2)n-O-
C(O)-N=N-C(O)-O-(CH2-CH2-O)n-Alk’之通式II的化合物較佳地可為：甲基-(O-CH2-CH2)n-O-C(O)-N=N-C(O)-O-(CH2-CH2-O)n-甲基、乙基-(O-CH2-CH2)n-O-C(O)-N=N-C(O)-O-(CH2-CH2-O)n-乙基、丙基-(O-CH2-CH2)n-O-C(O)-N=N-C(O)-O-(CH2-CH2-O)n-丙基、異丙基-(O-CH2-CH2)n-O-C(O)-N=N-C(O)-O-(CH2-CH2-O)n-異丙基、正丁基-(O-CH2-CH2)n-O-C(O)-N=N-C(O)-O-(CH2-CH2-O)n-正丁基、三級丁基-(O-CH2-CH2)n-O-C(O)-N=N-C(O)-O-(CH2-CH2-O)n-三級丁基、二級丁基-(O-CH2-CH2)n-O-C(O)-N=N-C(O)-O-(CH2-CH2-O)n-二級丁基、環己基-(O-CH2-CH2)n-O-C(O)-N=N-C(O)-O-(CH2-CH2-O)n-環己基或苄基-(O-CH2-CH2)n-O-C(O)-N=N-C(O)-O-(CH2-CH2-O)n-苄基。
通式III的化合物可為下列者，具有v=1至40、較佳為v=1至30、更佳為v=1至15：[(C11H23O-(CH2-CH2O)v]x(EtO)(3-x)Si-CH2-NH2、[(C12H25O-(CH2-CH2O)V]x(EtO)(3-x)Si-CH2-NH2、
[(C13H27O-(CH2-CH2O)V]x(EtO)(3-x)Si-CH2-NH2、[(C14H29O-(CH2-CH2O)V]x(EtO)(3-x)Si-CH2-NH2、[(C15H31O-(CH2-CH2O)V]x(EtO)(3-x)Si-CH2-NH2、[(C16H33O-(CH2-CH2O)V]x(EtO)(3-x)Si-CH2-NH2、[(C17H35O-(CH2-CH2O)V]x(EtO)(3-x)Si-CH2-NH2、[(C18H37O-(CH2-CH2O)V]x(EtO)(3-x)Si-CH2-NH2、[(C11H23O-(CH2-CH2O)v]x(EtO)(3-x)Si-CH2-CH2-NH2、[(C12H25O-(CH2-CH2O)V]x(EtO)(3-x)Si-CH2-CH2-NH2、[(C13H27O-(CH2-CH2O)V]x(EtO)(3-x)Si-CH2-CH2-NH2、[(C14H29O-(CH2-CH2O)V]x(EtO)(3-x)Si-CH2-CH2-NH2、[(C15H31O-(CH2-CH2O)V]x(EtO)(3-x)Si-CH2-CH2-NH2、[(C16H33O-(CH2-CH2O)V]x(EtO)(3-x)Si-CH2-CH2-NH2、[(C17H35O-(CH2-CH2O)V]x(EtO)(3-x)Si-CH2-CH2-NH2、[(C18H37O-(CH2-CH2O)V]x(EtO)(3-x)Si-CH2-CH2-NH2、[(C11H23O-(CH2-CH2O)v]x(EtO)(3-x)Si-CH2-CH2-CH2-NH2、[(C12H25O-(CH2-CH2O)V]x(EtO)(3-x)Si-CH2-CH2-CH2-NH2、[(C13H27O-(CH2-CH2O)V]x(EtO)(3-x)Si-CH2-CH2-CH2-NH2、[(C14H29O-(CH2-CH2O)V]x(EtO)(3-x)Si-CH2-CH2-CH2-NH2、[(C15H31O-(CH2-CH2O)V]x(EtO)(3-x)Si-CH2-CH2-CH2-NH2、[(C16H33O-(CH2-CH2O)V]x(EtO)(3-x)Si-CH2-CH2-CH2-NH2、[(C17H35O-(CH2-CH2O)V]x(EtO)(3-x)Si-CH2-CH2-CH2-NH2、[(C18H37O-(CH2-CH2O)V]x(EtO)(3-x)Si-CH2-CH2-CH2-NH2、[(C11H23O-(CH2-CH2O)v]x(CH3)(3-x)Si-CH2-NH2、[(C12H25O-(CH2-CH2O)V]x(CH3)(3-x)Si-CH2-NH2、
[(C13H27O-(CH2-CH2O)V]x(CH3)(3-x)Si-CH2-NH2、[(C14H29O-(CH2-CH2O)V]x(CH3)(3-x)Si-CH2-NH2、[(C15H31O-(CH2-CH2O)V]x(CH3)(3-x)Si-CH2-NH2、[(C16H33O-(CH2-CH2O)V]x(CH3)(3-x)Si-CH2-NH2、[(C17H35O-(CH2-CH2O)V]x(CH3)(3-x)Si-CH2-NH2、[(C18H37O-(CH2-CH2O)V]x(CH3)(3-x)Si-CH2-NH2、[(C11H23O-(CH2-CH2O)v]x(CH3)(3-x)Si-CH2-CH2-CH2-NH2、[(C12H25O-(CH2-CH2O)V]x(CH3)(3-x)Si-CH2-CH2-CH2-NH2、[(C13H27O-(CH2-CH2O)V]x(CH3)(3-x)Si-CH2-CH2-CH2-NH2、[(C14H29O-(CH2-CH2O)V]x(CH3)(3-x)Si-CH2-CH2-CH2-NH2、[(C15H31O-(CH2-CH2O)V]x(CH3)(3-x)Si-CH2-CH2-CH2-NH2、[(C16H33O-(CH2-CH2O)V]x(CH3)(3-x)Si-CH2-CH2-CH2-NH2、[(C17H35O-(CH2-CH2O)V]x(CH3)(3-x)Si-CH2-CH2-CH2-NH2或[(C18H37O-(CH2-CH2O)V]x(CH3)(3-x)Si-CH2-CH2-CH2-NH2。
本發明之方法的產物可包含以13C NMR所測定之超過30莫耳%、較佳為超過50莫耳%、更佳為超過75莫耳%、最佳為超過80莫耳%之通式I的含矽之偶氮二甲醯胺。
本發明之方法的產物可包含以13C NMR所測定之少於50莫耳%、較佳為少於25莫耳%、更佳為少於15莫耳%、最佳為少於10莫耳%之通式II的次成分(secondary constituent)。
本發明之方法的產物可包含以13C NMR所測定之少
於50莫耳%、較佳為少於25莫耳%、更佳為少於15莫耳%、最佳為少於10莫耳%之通式III和IV的次成分。
在產物中之通式II的化合物之相對莫耳%的量係以通式II及I的化合物之13C NMR中的羰基C原子之積分(integral)的比來測定。
式II的化合物之相對莫耳%=(在式II中的所有-(C=O)原子之積分)/(在式II中的所有-(C=O)原子之積分)+(在式I中的所有-(C=O)原子之積分))。
本發明之方法的產物可包含通式IV、V、VI和VII的化合物Sub1-X1-C(O)-NH-NH-C(O)-X2-Sub2 (IV)
(A1)x(A2)(3-x)Si-R1-N(D1)-CO-NH-NH-CO-N(D1)-R1-Si(A1)x(A2)(3-x) (V)
(A1)x(A2)(3-x)Si-R1-NH-CO-NH-NH-CO-X2-Sub2 (VI)
(A1)x(A2)(3-x)Si-R1-NH-CO-NH-NH-CO-X1-Sub1 (VII)。
在產物中之通式III和IV的化合物之相對莫耳%係藉由積分(integration)及藉由在13C NMR中之N-相鄰的C原子(NH2-CH2-)對通式I的化合物之N-相鄰的C原子(-(C=O)-NH-CH2-)之莫耳%的比來測定。
式III化合物之相對莫耳%=(在式III中與N相鄰之R1的所有C原子之積分)/((在式III中與N相鄰之R1的所有C原子之積分)+(在式I中與N相鄰之R1的所有C原子之積分))。
本發明之方法可在溶劑中或不在溶劑中進行。
相對於所使用之通式II的化合物，溶劑量可為介於1重量%與5000重量%之間，較佳為介於1重量%與1000重量%之間，更佳為介於50重量%與1000重量%之間，更佳為介於50重量%與500重量%之間。
相對於所使用之通式II的化合物，溶劑量可為超過1重量%，較佳為超過10重量%，更佳為超過50重量%，更佳為超過100重量%。
所使用之溶劑可具有-100℃至250℃、較佳為0-150℃、更佳為20-100℃之沸點。
所使用之溶劑可為醇系(alcoholic)或非醇系化合物。
所使用之溶劑可為醇系及/或非醇系化合物之混合物。
非醇系溶劑可為含鹵素或不含鹵素之溶劑。
非醇系、含鹵素之溶劑較佳地可為CCl4、CHCl3、CH2Cl2、CH3Cl、CCl3-CCl3、CHCl2-CCl3、CHCl2-CHCl2或CH2Cl-CH2Cl。
所使用之非醇系、不含鹵素之溶劑較佳地可為烷烴(alkane)、醚、硫醇(mercaptan)、二烷基硫化物(dialkyl sulphide)或烷基磷烷(alkylphosphane)。
所使用之非醇系、不含鹵素之溶劑最佳地可為烷烴或烷烴之混合物，諸如戊烷、己烷、環己烷、庚烷或辛烷。
所使用之醇系溶劑可為直鏈、環狀或支鏈醇。
所使用之醇亦可為醇之混合物。
尤佳者可能使用相應於式III的化合物之矽上的各個
烷氧基取代基之醇。
最特佳者為可使用甲醇、乙醇、環己醇、正丁醇、三級丁醇或異丙醇。
反應較佳地可排除空氣及水來進行。
反應可在惰性氣體氛圍下進行，例如在氬氣或氮氣下，較佳為氮氣下。
本發明之方法可在大氣壓力、升壓或減壓下進行。
以大氣壓力及減壓較佳。
升壓可為從1.1巴至100巴、較佳為1.5巴至50巴、更佳為2巴至20巴、且最佳為2至10巴之壓力。
減壓可為1毫巴(mbar)至1000毫巴、較佳為1毫巴至500毫巴、更佳為1毫巴至250毫巴、最佳為5毫巴至100毫巴之壓力。
本發明之方法可在介於-100℃與+200℃之間、較佳為介於-25與150℃之間、更佳為介於-10℃與100℃之間、最佳為介於-10與50℃之間的溫度下進行。
用於本發明之方法的通式II的物質可計量加至通式III的物質中。
用於本發明之方法的通式III的物質可計量加至通式II的物質中。
用於本發明之方法的穩定劑可在反應之前、期間或之後添加。
可添加穩定劑之混合物。
穩定劑可抑制或延緩熱誘發(thermally induced)之偶
氮化合物分解。
穩定劑可為自由基捕獲劑(radical scavenger)。
穩定劑可為螯合劑(chelating agent)。
穩定劑可抑制或延緩光誘發(light-induced)之偶氮化合物分解。
穩定劑可為UV穩定劑。
穩定劑可抑制或延緩氧化反應。
穩定劑可為陰離子(anionic)或陽離子(cationic)化合物。
穩定劑可包含雜原子，諸如氧、硫、氮或磷。
穩定劑可為羧酸，較佳為二羧酸或三羧酸。較佳者為1,2,4-苯三甲酸(trimellitic acid)(CAS 528-44-9)、1,2,4,5-苯四甲酸(pyromellitic acid)(CAS 89-05-4)、酞酸(phthalic acid)、氮基三乙酸(nitrilotriacetic acid)(CAS 139-13-9)、α-羥基琥珀酸(alpha-hydroxysuccinic acid)(CAS 6915-15-7)、己二酸、反丁烯二酸和順丁烯二酸。
穩定劑可為羧酸酐(carboxylic anhydride)，較佳為環羧酸酐(cyclic carboxylic anhydride)。特佳者為1,2,4-苯三甲酸酐(trimellitic anhydride)(TMSA，CAS 552-30-7)、1,2,4,5-苯四甲酸二酐(pyromellitic dianhydride)(CAS 89-32-7)、四氫-2,5-呋喃二醚(tetrahydro-2,5-furandione)(CAS 108-30-5)、酞酸酐(phthalic anhydride)和順丁烯二酸酐(maleic anhydride)。
穩定劑可為醇，較佳為二醇或三醇。優先選擇為對苯
二酚(hydroquinone)、二乙醇胺(diethanolamine)和三乙醇胺。
穩定劑可為苯并三唑(benzotriazole)(CAS 95-14-7)及其衍生物。優先選擇為
基三唑(tolyltriazole)(CAS 29385-43-1)、5-丁基苯并三唑(5-butylbenzotriazole)(CAS 3663-24-9)、1-(羥甲基)苯并三唑(1-(hydroxymethyl)benzotriazole)(CAS 28539-02-8)。
苯并三唑衍生物可相當於US 5 441 563、US 5 548 003和FR 2722205中具體指出的那些衍生物。
穩定劑可為苯并咪唑及其衍生物。優先選擇為1-羥甲基苯并咪唑(1-hydroxymethylbenzimidazole)(CAS 19541-99-2)、CAS 13786-58-8、CAS 18249-94-0和CAS 81247-25-8。
用於根據本發明之式I的化合物之穩定劑可為橡膠工業中慣用且已知為加速劑及活化劑之物質。
穩定劑可為硫脲(thiocarbamide)。
穩定劑較佳地可為2-巰基苯并噻唑(2-mercaptobenzothiazole)、二苯并噻唑基二硫化物(dibenzothiazyl disulphide)、2-(N-
啉基硫基)苯并噻唑(2-(morpholinothio)benzothiazole)、二異丙基苯并噻唑基次磺醯胺(diisopropylbenzothiazylsulphenamide)、N-環己基-2-苯并噻唑基次磺醯胺、N,N-二環己基-2-苯并噻唑基次磺醯胺、N-三級丁基-2-苯并噻唑基次磺醯胺、苯并噻唑基-2-碸烯
啉化物(benzothiazyl-2-sulphene
morpholide)、N-二環己基-2-苯并噻唑基次磺醯胺、四甲基秋蘭姆單硫化物(tetramethylthiuram monosulphide)、四甲基秋蘭姆二硫化物(tetramethylthiuram disulphide)、四乙基秋蘭姆二硫化物、四丁基秋蘭姆二硫化物、四苄基秋蘭姆二硫化物(tetrabenzylthiuram disulphide)、四異丁基秋蘭姆二硫化物、N,N’-二甲基-N,N’-二苯基秋蘭姆二硫化物、二-五亞甲基秋蘭姆二硫化物(dipentamethylenethiuram disulphide)和二-五亞甲基秋蘭姆四/六硫化物。
於本發明之方法，可使用以所使用之通式II的物質質量為基準計為0.001至100重量%、較佳為0.01至50重量%、更佳為0.01至10重量%、最佳為0.1至5重量%之穩定劑。
於本發明之方法，可使用以所使用之通式II的物質質量為基準計為超過0.001重量%、較佳為超過0.01重量%、更佳為超過0.1重量%、最佳為超過1重量%之穩定劑。
於本發明之方法，可使用以所使用之通式II的物質質量為基準計為少於100重量%、較佳為少於25重量%、更佳為少於10重量%、最佳為少於1重量%之穩定劑。
本發明進一步提供製備橡膠混合物之方法，其特徵在於將至少一種橡膠、至少一種填料與至少一種通式I的含矽之偶氮二甲醯胺混合，該橡膠係選自下列群組：乙烯-丙烯-二烯共聚物(EPDM)、乙烯-丙烯共聚物(EPM)、氯平
橡膠(chloroprene rubber)(CR)、氯化聚乙烯(chloropolyethylene)(CM)、氯異丁烯-異戊二烯(chloroisobutene-isoprene)(氯化丁基)橡膠(CIIR)、氯磺醯基聚乙烯(chlorosulfonyl polyethylene)(CSM)、乙烯-乙酸乙烯酯共聚物(EAM)、丙烯酸烷酯共聚物(ACM)、聚酯聚胺甲酸酯(polyester polyurethane)(AU)、聚醚聚胺甲酸酯(polyether polyurethane)(EU)、溴-異丁烯-異戊二烯(溴化丁基)橡膠(BIIR)、聚氯三氟乙烯(CFM)、異丁烯-異戊二烯橡膠(isobuteneisoprene rubber)(丁基橡膠、IIR)、異丁烯橡膠(IM)、聚異戊二烯(IR)、熱塑性聚酯聚胺甲酸酯(YAU)、熱塑性聚醚聚胺甲酸酯(YEU)、在聚合物鏈上具有甲基之矽氧橡膠(silicone rubber)(MQ)、氫化丙烯腈-丁二烯橡膠(hydrogenated acrylonitrile-butadiene rubber)(HNBR)、丙烯腈-丁二烯橡膠(NBR)或羧酸化丙烯腈-丁二烯橡膠(carboxylated acrylonitrile-butadiene rubber)(XNBR)，較佳為乙烯-丙烯-二烯共聚物(EPDM)。
本發明另外提供橡膠混合物，其特徵在於其包含(a)至少一種選自下列群組之橡膠：乙烯-丙烯-二烯共聚物(EPDM)、乙烯-丙烯共聚物(EPM)、氯平橡膠(CR)、氯化聚乙烯(CM)、氯異丁烯-異戊二烯(氯化丁基)橡膠(CIIR)、氯磺基聚乙烯(CSM)、乙烯-乙酸乙烯酯共聚物(EAM)、丙烯酸烷酯共聚物(ACM)、聚酯聚胺甲酸酯(AU)，聚醚聚胺甲酸酯(EU)、溴-異丁烯-異戊二烯(溴化丁基)橡膠(BIIR)、聚氯三氟乙烯(CFM)、異丁烯-異戊二烯橡
膠(丁基橡膠、IIR)、異丁烯橡膠(IM)、聚異戊二烯(IR)、熱塑性聚酯聚胺甲酸酯(YAU)、熱塑性聚醚聚胺甲酸酯(YEU)、在聚合物鏈上具有甲基之矽氧橡膠(MQ)、氫化丙烯腈-丁二烯橡膠(HNBR)、丙烯腈-丁二烯橡膠(NBR)或羧酸化丙烯腈-丁二烯橡膠(XNBR)，較佳為乙烯-丙烯-二烯共聚物(EPDM)，(b)至少一種填料，及(c)通式I的含矽之偶氮二甲醯胺。
用於製備本發明之橡膠混合物的較佳橡膠為乙烯-丙烯-二烯共聚物(EPDM)，其可含有第三單體(乙烯丙烯-三聚物(ethylenepropylene-terpolymer))。
本發明之橡膠混合物可含有額外的天然橡膠或合成橡膠。較佳的合成橡膠說明於例如W.Hofmann,Kautschuktechnologie[Rubber Technology],Genter Verlag,Stuttgart 1980中。該等橡膠尤其包括- 聚丁二烯(BR)；- 苯乙烯/丁二烯共聚物(SBR)，例如乳液-SBR(E-SBR)或溶液-SBR(S-SBR)。苯乙烯/丁二烯共聚物可具有1至60重量%、較佳為2至50重量%、更佳為10至40重量%、最佳為15至35重量%之苯乙烯含量；- 氯平(chloroprene)(CR)；- 異戊二烯橡膠(IR)；- 異丁烯/異戊二烯共聚物(丁基-IIR)；- 苯乙烯/異戊二烯共聚物(SIR)；
- 丁二烯/異戊二烯共聚物(BIR)；- 苯乙烯/丁二烯/異戊二烯共聚物(SBIR)；- 丁二烯/丙烯腈共聚物，具有丙烯腈含量為5至60，較佳為10至50重量%(NBR)，更佳為10至45重量%(NBR)，最佳為19至45重量%(NBR)；- 部分氫化或完全氫化NBR橡膠(HNBR)；- 乙烯/丙烯/二烯共聚物(EPDM)；- 另外具有官能基(諸如羧基、矽烷醇基(silanol)或環氧基)的上述橡膠，例如實例為環氧化NR、羧基官能化NBR或矽烷醇-(-SiOH)及/或矽基烷氧基官能化(silylalkoxy-functionalized)(-Si-OR)SBR；及該等橡膠之混合物。
橡膠混合物可包含天然橡膠及/或異戊二烯橡膠與其他二烯橡膠之混合物作為其橡膠。
所使用之異戊二烯橡膠較佳地可為1,4型。高含量的順式-1,4鍵可能較佳，通常超過90莫耳%，更佳為超過95莫耳%，最佳為超過98莫耳%。
用於橡膠混合物之填料可為下列者：
- 碳黑，例如燈黑(lamp black)、爐黑(furnace black)、氣黑(gas black)或熱碳黑(thermal black)。碳黑可具有20至200平方公尺/克(m2/g)之BET表面積。碳黑亦可隨意地(optionally)包括雜原子例如，諸如Si。碳黑可經部分氧化且可包含(-OH)基團或(-COOH)基團。
- 非晶形矽石(Amorphous silica)，其係例如藉由沉
澱矽酸鹽溶液(沈澱矽石(precipitated silica))或藉由鹵化矽(silicon halide)之火燄水解(flame hydrolysis)(熱解(pyrogenic)或發煙(fumed)矽石)而製得。沈澱及發煙矽石可具有5至1000平方公尺/克、較佳為20至400平方公尺/克之比表面積(BET表面積)。沈澱及發煙矽石可具有5至1000平方公尺/克、較佳為20至400平方公尺/克之比表面積(BET表面積)及0.1至1000微米(μm)、較佳為0.1至500微米之以篩分(sieving)測量的粒徑分布(particle size distribution)。沈澱及發煙矽石可具有關於彼等粒徑分布之高斯分布(Gaussian distribution)。矽石亦可隨意地呈與其他的金屬氧化物(諸如Al、Mg、Ca、Ba、Zn和鈦氧化物)之混合型氧化物的形式。
- 合成矽酸鹽(synthetic silicate)，諸如矽酸鋁、鹼土金屬矽酸鹽(例如矽酸鎂或矽酸鈣)。合成矽酸鹽可具有20至400平方公尺/克之BET表面積及10至400奈米(nm)之初級粒徑(primary particle diameter)。
- 合成或天然的鋁氧化物和鋁氫氧化物。
- 天然矽酸鹽，諸如高嶺土和其他天然生成矽石。
- 碳酸鹽，較佳為碳酸鈣。
- 玻璃纖維和玻璃纖維產品(蓆(mat)、線(strand))或玻璃微珠(glass microbead)。
較佳為可使用藉由沉澱矽酸鹽之溶液而製得的非晶形矽石(沈澱矽石)，其具有20至400平方公尺/克、較佳為50至300平方公尺/克、更佳為80至220平方公尺/克之
BET表面積；及發煙矽石，其具有20至400平方公尺/克、較佳為50至300平方公尺/克、更佳為80至220平方公尺/克之BET表面積。沈澱矽石(precipitated silica)及發煙矽石(fumed silica)可在各例子中以1至300重量份、較佳為5至200重量份、更佳為5至150重量份之量(以100份橡膠(phr)為基準計)使用。
非晶形矽石可為例如來自Evonik Industries AG之Ultrasils或Sipernats、或來自Rhodia之Zeosils。
發煙矽石可為例如來自Evonik Industries AG之Aerosil產品、來自Cabot之Cabosils、或來自Wacker之HDK矽石。
所述及之填料可單獨或以混合物使用。
在一個較佳的型式中，橡膠混合物可包含10至150重量份氧化物(oxidic)或矽酸鹽(silicatic)填料、隨意地與0至100重量份碳黑、以及1至50(較佳為2至30，更佳為3至20)重量份根據本發明之通式I的含矽之偶氮二甲醯胺(在各例子中以100重量份橡膠為基準計)。
橡膠混合物可包含其他的橡膠輔助劑、諸如例如反應加速劑、老化抑制劑、熱穩定劑、光穩定劑、抗臭氧劑、加工輔助劑、塑化劑、膠黏劑、發泡劑、染料、顏料、蠟、增量劑(extender)、有機酸、阻滯劑(retardant)、金屬氧化物還有活化劑諸如三乙醇胺或己三醇(hexanetriol)。
其他的橡膠輔助劑可為下列者：聚乙二醇及/或聚丙二醇及/或聚丁二醇，具有介於50
與50 000克/莫耳(g/mol)之間、較佳為介於50與20 000克/莫耳之間、更佳為介於200與10 000克/莫耳之間、最佳為介於400與6000克/莫耳之間、極佳為介於500與3000克/莫耳之間的莫耳重量(molar weight)，以烴為末端之聚乙二醇(hydrocarbon-terminated polyethylene glycol)Alk”-O-(CH2-CH2-O)yI-H或Alk”-(CH2-CH2-O)yI-Alk”，以烴為末端之聚丙二醇Alk”-O-(CH2-CH(CH3)-O)yI-H或Alk”-O-(CH2-CH(CH3)-O)yI-Alk”，以烴為末端之聚丁二醇Alk”-O-(CH2-CH2-CH2-CH2-O)yI-H、Alk”-O-(CH2-CH(CH3)-CH2-O)yI-H、Alk”-O-(CH2-CH2-CH2-CH2-O)yI-Alk”或Alk”-O-(CH2-CH(CH3)-CH2-O)yI-Alk”，其中yI平均為2至25，yI平均較佳為2至15，yI平均更佳為3至8及10至14，yI平均最佳為3至6及10至13；以及Alk”為具有1至35、較佳為4至25、更佳為6至20、最佳為10至20、極佳為11至14個碳原子的支鏈或非支鏈、未經取代或經取代、飽和或不飽和單價烴，經聚乙二醇醚化(polyethylene glycol-etherified)、經聚丙二醇醚化或經聚丁二醇醚化(或經其混合物醚化之每一下列者)之新戊二醇(neopentyl glycol)HO-CH2-C(Me)2-CH2-OH、新戊四醇(pentaerythritol)C(CH2-OH)4或三羥甲丙烷CH3-CH2-C(CH2-OH)3，其中在經醚化之多醇
(etherified polyalcohol)中的乙二醇、丙二醇及/或丁二醇之重複單元可為介於2與100之間，較佳為介於2與50之間，更佳為介於3與30之間，最佳為介於3與15之間。
至於計算yI之平均值，可形成聚伸烷基二醇單元(polyalkylene glycol unit)的分析可測定量(analytically determinable amount)對-Alk”的分析可測定量之比[(聚伸烷基二醇單元量)/(-Alk”量)]。該等量可使用例如1H及13C核磁共振光譜法來測定。
可使用已知量的橡膠輔助劑，該等量係以包括意欲用途的因素決定。所使用之各加工輔助劑(processing auxiliary)的慣用量可為以橡膠為基準計(phr)為0.001至50重量%、較佳為0.001至30重量%、更佳為0.01至30重量%、最佳為0.1至30重量%之量。
橡膠混合物可為硫可硫化(sulphur-vulcanizable)的橡膠混合物。
橡膠混合物可為可過氧化交聯(peroxidically crosslinkable)的橡膠混合物。
所使用之交聯劑可為硫本身或硫供體(sulphur donor)。硫可以0.1至10重量%、較佳為0.1至5重量%之量(以橡膠為基準計)使用。
所使用之加速劑(accelerator)可為2-巰基苯并噻唑、二苯并噻唑基二硫化物、巰基苯并噻唑鋅(zinc mercaptobenzothiazole)、2-(N-
啉基硫基)苯并噻唑、二
異丙基苯并噻唑基碸烯醯胺(diisopropylbenzothiazylsulpheneamide)、N-環己基-2-苯并噻唑基碸烯醯胺、N,N-二環己基-2-苯并噻唑基碸烯醯胺、N-三級丁基-2-苯并噻唑基碸烯醯胺、苯并噻唑基-2-碸烯
啉化物、N-二環己基-2-苯并噻唑基次磺醯胺(N-dicyclohexyl-2-benzothiazylsulphenamide)、四甲基秋蘭姆單硫化物、四甲基秋蘭姆二硫化物、四乙基秋蘭姆二硫化物、四丁基秋蘭姆二硫化物、四苄基秋蘭姆二硫化物、四異丁基秋蘭姆二硫化物、N,N’-二甲基-N,N’-二苯基秋蘭姆二硫化物、二-五亞甲基秋蘭姆二硫化物、二-五亞甲基秋蘭姆四/六硫化物、N,N’-乙基硫脲(N,N‘-ethylthiourea)、N,N’-二乙基硫脲、N,N’-二苯基硫脲、N’-(3,4-二氯苯基)-N,N’-二甲基硫脲、N,N’-二丁基硫脲、N,N,N’-三丁基硫脲、二甲基二硫胺甲酸鋅(zinc dimethyldithiocarbamate)、二乙基二硫胺甲酸鋅、二丁基二硫胺甲酸鋅、二異丁基二硫胺甲酸鋅、二苄基二硫胺甲酸鋅、乙基苯基二硫胺甲酸鋅、五亞甲基二硫胺甲酸鋅、二異壬基二硫胺甲酸鋅、二戊基二硫胺甲酸鋅、二乙基二硫胺甲酸碲、二甲基二硫胺甲酸銅、二丁基二硫胺甲酸銅、二甲基二硫胺甲酸鉍、二乙基二硫胺甲酸鎘、二乙基二硫胺甲酸硒、哌啶五亞甲基二硫胺甲酸酯(piperidinepentamethylenedithiocarbamate)、二甲基二硫胺甲酸鎳、二乙基二硫胺甲酸鎳、二丁基二硫胺甲酸鎳、二異丁基二硫胺甲酸鎳、二苄基二硫胺甲酸鎳、二戊基二硫胺甲酸鉛、二甲基二硫胺甲酸鈉、二乙基
二硫胺甲酸鈉、二丁基二硫胺甲酸鈉、二異丁基二硫胺甲酸鈉或二苄基二硫胺甲酸鈉。
所使用之輔助加速劑可為二苯基胍、二-鄰-
基胍(di-o-tolylguanidine)、鄰-
基雙胍(o-tolylbiguanidine)、N,N’-二苯基胍、六亞甲四胺(hexamethylenetetramine)、均勻的丙烯醛(homologous acrolein)與芳族鹼之縮合產物(condensation product)、或醛與胺之縮合產物。
通式I的含矽之偶氮二甲醯胺可用作為無機材料(例如玻璃珠、玻璃片、玻璃表面、玻璃纖維、金屬表面、氧化物填料(例如矽石))與有機聚合物(例如熱固物、熱塑物或彈性體)之間的黏著促進劑，以及作為氧化物表面的交聯劑和表面改質劑。
通式I的含矽之偶氮二甲醯胺可作為偶合試劑(coupling reagent)用於經填充之橡膠混合物中，實例為例如工業橡膠物件(諸如阻尼元件(damping element))中或鞋襪底(footwear sole)中。
在混合操作中，通式I的含矽之偶氮二甲醯胺的添加，以及填料和添加劑的添加可發生在50至200℃、較佳為70至180℃、更佳為90至160℃之批組溫度(batch temperature)下。通式I的含矽之偶氮二甲醯胺的添加可在計量添加其他橡膠輔助劑之前、期間或之後進行。
橡膠與填料、隨意的(optionally)橡膠輔助劑及通式I的含矽之偶氮二甲醯胺之混合可在已知的混合組件中進行，諸如滾筒、內部混合器和混合擠壓器。
橡膠混合物之硫化(vulcanization)可發生在90至230℃、較佳為110至210℃、更佳為120至190℃之溫度下，隨意地(optionally)在10至200巴之壓力下。
橡膠混合物可用於製造成形物件，例如用於製造電纜護套(cable sheathing)、軟管(hose)、傳動帶(drive belt)、輸送帶、捲筒覆蓋物(roll covering)、鞋襪底(footwear sole)、環封(ring seal)或阻尼元件(damping element)。
化合物(C13H27(-O-CH2-CH2)5-O-)x(EtO)3-xSi-(CH2)3-NH2係藉由(EtO)3Si-(CH2)3-NH2與C13H27(-O-CH2-CH2)5-OH之轉酯化反應(transesterification)而製得，類似於EP 0085831或DE 3203688及EP 1683801中的說明，沒有絕對需要觸媒。
用於實施例的原料係如下：來自Novasep之偶氮二羧酸二異丙酯(diisopropyl azodicarboxylate)、來自Evonik Industries AG之3-胺基丙基(三乙氧基矽烷)(3-aminopropyl(triethoxysilane))、來自Sasol之Marlosol TA 3050(乙氧基化異三癸醇(ethoxylated isotridecanol))。
使用來自VWR之戊烷作為溶劑。
將戊烷(300毫升)中的[(C13H27(-O-CH2-CH2)5-O-)1.0(EtO)2.0Si-(CH2)3-NH2(286克)在-3℃、氬氛圍下引入燒瓶中且攪拌。將偶氮二羧酸二異丙酯(48.5克)在-5至+5℃下經15分鐘期間逐滴添加至此混合物中。接著移除冷卻浴且將溶液攪拌180分鐘，混合物在此期間溫熱至室溫。接著在下降至0.2毫巴之壓力下移除所有的揮發性成分(戊烷、異丙醇)。分離出成為透明紅色油的產物(307克)。
上文記述之方法得到w%(SiO2)=9.4%及因此計算之x=1.0。
將戊烷(300毫升)中的[(C13H27(-O-CH2-CH2)5-O-)2.0(EtO)1.0Si-(CH2)3-NH2(251克)在0℃、氬氛圍下引入燒瓶中且攪拌。將偶氮二羧酸二異丙酯(26.1克)在-5至+5℃下經15分鐘期間逐滴添加至此混合物中。接著移除冷卻浴且將溶液攪拌180分鐘，混合物在此期間溫熱至室溫。接著在下降至0.2毫巴之壓力下移除所有的揮發性成分(戊烷、異丙醇)。分離出成為透明紅色油的產物(322克)。
上文記述之方法得到w%(SiO2)=5.9%及因此計算之
x=2.0。
將戊烷(300毫升)中的[(C13H27(-O-CH2-CH2)5-O-)1.3(EtO)1.7Si-(CH2)3-NH2(246克)在0℃、氬氛圍下引入燒瓶中且攪拌。將偶氮二羧酸二異丙酯(35.1克)在-5至+8℃下經15分鐘期間逐滴添加至此混合物中。接著移除冷卻浴且將溶液攪拌180分鐘，混合物在此期間溫熱至室溫。接著在下降至0.2毫巴之壓力下移除所有的揮發性成分(戊烷、異丙醇)。分離出成為透明紅色油的產物(262克)。
上文記述之方法得到w%(SiO2)=8.0%及因此計算之x=1.3。
製備[(C13H27(-O-CH2-CH2)5-O-)1.5(EtO)1.5Si-(CH2)3-NH-C(=O)-N=]2
將戊烷(300毫升)中的[(C13H27(-O-CH2-CH2)5-O-)1.5(EtO)1.5Si-(CH2)3-NH2(276克)在0℃、氬氛圍下引入燒瓶中且攪拌。將偶氮二羧酸二異丙酯(35.9克)在-5至+5℃下經10分鐘期間逐滴添加至此混合物中。接著移除冷卻浴且將溶液攪拌180分鐘，混合物在此期間溫熱至室
溫。接著在下降至0.2毫巴之壓力下移除所有的揮發性成分(戊烷、異丙醇)。分離出成為透明紅色油的產物(291克)。
上文記述之方法得到w%(SiO2)=7.3%及因此計算之x=1.5。
將戊烷(300毫升)中的[(C13H27(-O-CH2-CH2)5-O-)1.7(EtO)1.3Si-(CH2)3-NH2(305克)在0℃、在氬氛圍下引入燒瓶中且攪拌。將偶氮二羧酸二異丙酯(40.0克)在-5至+5℃下經15分鐘期間逐滴添加至此混合物中。接著移除冷卻浴且將溶液攪拌180分鐘，混合物在此期間溫熱至室溫。接著在下降至0.2毫巴之壓力下移除所有的揮發性成分(戊烷、異丙醇)。分離出成為透明紅色油的產物(263克)。
上文記述之方法得到w%(SiO2)=6.6%及因此計算之x=1.7。
用於橡膠混合物之調配物列示於以下表1中。單位phr意指以100份所使用之原料橡膠為基準計的重量份。矽烷係以等莫耳(equimolarly)計量，換言之與物質相同的
量。用於製備橡膠混合物及其硫化橡膠(vulcanizate)之通用方法說明於以下書籍中："Rubber Technology Handbook",W.Hofmann,Hanser Verlag 1994。
聚合物Buna® EP G 5455為來自Lanxess之乙烯-丙烯-5三聚物，具有平均不飽和度(ENB含量)=4.3，含有50phr石蠟油(paraffinic oil)。孟納黏度(Mooney viscosity)(UML(1+4)125℃)為46。
Ultrasil 7000 GR為來自Evonik Industries AG之可輕易分散的矽石且具有170平方公尺/克之BET表面積。
來自Sasol之Lipoxol 4000為聚乙二醇4000。
來自Holly Corporation之Sunpar 150為石蠟油。
來自Lanxess之Vulkacit Mercapto C為2-巰基苯并噻唑(MBT)。Perkacit TBzTD(四苄基秋蘭姆四硫化物)為來自Flexsys N.V.之產品；Rhenocure TP/S係來自RheinChemie且為結合至33%之矽石的67%之二烷基二硫磷酸鋅(zinc dialkyldithiophosphate)。
橡膠混合物係在內部混合器(internal mixer)中根據表2中的混合方法製得。
表3總結橡膠測試之方法。
表4顯示技術性橡膠測試結果。硫化係在155℃下發生30分鐘。
如表4可看出，相對於混合物1、2和6(比較混合物)，具有本發明之矽烷的本發明混合物3、4和5顯現出優點。相對於包含具有平均聚醚分率小於及大於所界定之範圍(claimed range)的矽烷之橡膠混合物，以等莫耳計量(equimolar metering)的例子觀察到明顯改進的模量300、δ轉矩及抗撕裂性。
Claims (8)
- 一種通式I的含矽之偶氮二甲醯胺(A1)x(A2)(3-x)Si-R1-N(D1)-CO-N=N-CO-N(D1)-R1-Si(A1)x(A2)(3-x) (I),其中A1為烷基聚醚基團-O-((CRI 2)w-O-)v-Alk，其中v=1-60，w=1-20，RI在各情況下獨立為H、苯基或非支鏈或支鏈烷基，Alk為支鏈或非支鏈、飽和或不飽和、經取代或未經取代之脂族、芳族或混合型脂族/芳族單價C1-C35烴基，A2為相同或不同且為支鏈或非支鏈烷基、支鏈或非支鏈烷氧基、支鏈或非支鏈C2-C25烯氧基、C6-C35芳氧基、支鏈或非支鏈C7-C35烷基芳氧基、支鏈或非支鏈C7-C35芳烷氧基或羥基(-OH)，D1為相同或不同且為H或Alk’，其中Alk’為C1-C18烷基、C5-C18環烷基或C6-C18芳基，R1為相同或不同且為支鏈或非支鏈、飽和或不飽和之脂族、芳族或混合型脂族/芳族二價C1-C30烴基，其隨意地經F-、Cl-、Br-、I-、-CN或HS-取代，其特徵在於平均聚醚分率x=1.3-1.7。
- 根據申請專利範圍第1項的含矽之偶氮二甲醯胺，其中，A1為-O-((CH2)w-O-)5C13H27。
- 根據申請專利範圍第1項的含矽之偶氮二甲醯胺，其中，該含矽之偶氮二甲醯胺為[(C13H27(-O-CH2- CH2)5-O-)1.5(EtO)1.5Si-(CH2)3-NH-C(=O)-N=]2、[(C13H27(-O-CH2-CH2)5-O-)1.3(EtO)1.7Si-(CH2)3-NH-C(=O)-N=]2、[(C13H27(-O-CH2-CH2)5-O-)1.4(EtO)1.6Si-(CH2)3-NH-C(=O)-N=]2、[(C13H27(-O-CH2-CH2)5-O-)1.7(EtO)1.3Si-(CH2)3-NH-C(=O)-N=]2或[(C13H27(-O-CH2-CH2)5-O-)1.6(EtO)1.4Si-(CH2)3-NH-C(=O)-N=]2。
- 一種製備根據申請專利範圍第1項的含矽之偶氮二甲醯胺的方法，其特徵在於將通式II的偶氮二羧基化合物Sub1-X1-C(O)-N=N-C(O)-X2-Sub2 (II)與通式III的胺基矽烷反應(A1)x(A2)(3-x)Si-R1-N(D1)H (III)其中x、A1、A2、R1和D1具有如前所述之定義，及Sub1和Sub2為相同或不同且為H、支鏈或非支鏈C1-C18烷基、苄基(-CH2-C6H5)或烷基聚醚(CH2-CH2-O)n-Alk’或(CH(CH3)-CH2-O)n-Alk’，其中n為1至10，且Alk’具有如前所述之定義，X1和X2為相同或不同且為O或NH。
- 一種製備橡膠混合物之方法，其特徵在於將至少一種選自下列群組之橡膠：乙烯-丙烯-二烯共聚物 (EPDM)、乙烯-丙烯共聚物(EPM)、氯平橡膠(ehloroprene rubber)(CR)、氯化聚乙烯(chloropolyethylene)(CM)、氯異丁烯-異戊二烯(chloroisobutene-isoprene)(氯化丁基)橡膠(CIIR)、氯磺醯基聚乙烯(chlorosulfonyl polyethylene)(CSM)、乙烯-乙酸乙烯酯共聚物(EAM)、丙烯酸烷酯共聚物(ACM)、聚酯聚胺甲酸酯(polyester polyurethane)(AU)、聚醚聚胺甲酸酯(polyether polyurethane)(EU)、溴異丁烯-異戊二烯(bromo-isobutene-isoprene)(溴化丁基)橡膠(BIIR)、聚氯三氟乙烯(CFM)、異丁烯-異戊二烯橡膠(isobuteneisoprene rubber)(丁基橡膠，IIR)、異丁烯橡膠(IM)、聚異戊二烯(IR)、熱塑性聚酯聚胺甲酸酯(YAU)、熱塑性聚醚聚胺甲酸酯(YEU)、在聚合物鏈上具有甲基之矽氧橡膠(silicone rubber)(MQ)、氫化丙烯腈-丁二烯橡膠(hydrogenated acrylonitrile-butadiene rubber)(HNBR)、丙烯腈-丁二烯橡膠(NBR)或羧酸化丙烯腈-丁二烯橡膠(carboxylated acrylonitrile-butadiene rubber)(XNBR)，至少一種填料，以及至少一種根據申請專利範圍第1項的含矽之偶氮二甲醯胺混合。
- 一種橡膠混合物，其特徵在於其包含(a)至少一種選自下列群組之橡膠：乙烯-丙烯-二烯共聚物(EPDM)、乙烯-丙烯共聚物(EPM)、氯平橡膠(CR)、氯化聚乙烯(CM)、氯異丁烯-異 戊二烯(氯化丁基)橡膠(CIIR)、氯磺醯基聚乙烯(CSM)、乙烯-乙酸乙烯酯共聚物(EAM)、丙烯酸烷酯共聚物(ACM)、聚酯聚胺甲酸酯(AU)、聚醚聚胺甲酸酯(EU)、溴異丁烯-異戊二烯(溴化丁基)橡膠(BIIR)、聚氯三氟乙烯(CFM)、異丁烯-異戊二烯橡膠(丁基橡膠，IIR)、異丁烯橡膠(IM)、聚異戊二烯(IR)、熱塑性聚酯聚胺甲酸酯(YAU)、熱塑性聚醚聚胺甲酸酯(YEU)、在聚合物鏈上具有甲基之矽氧橡膠(MQ)、氫化丙烯腈-丁二烯橡膠(HNBR)、丙烯腈-丁二烯橡膠(NBR)或羧酸化丙烯腈-丁二烯橡膠(XNBR)，(b)至少一種填料，以及(c)根據申請專利範圍第1項的含矽之偶氮二甲醯胺。
- 根據申請專利範圍第6項的橡膠混合物，其中，該橡膠為乙烯-丙烯-二烯共聚物(EPDM)。
- 一種根據申請專利範圍第6項之橡膠混合物的用途，其係用於電纜護套(cable sheathing)、軟管、傳動帶(drive belt)、輸送帶、捲筒覆蓋物(roll covering)、鞋襪底(footwear sole)、環封(ring seal)和阻尼元件(damping element)。
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| US5441563A (en) | 1993-07-06 | 1995-08-15 | Armstrong World Industries, Inc. | Highly insoluble azole embossing inhibitor and the use thereof |
| FR2722205B1 (fr) | 1995-04-11 | 2001-07-06 | Armstrong World Ind Inc | Encre d'imprimerie contenant un inhibiteur de gaufrage azolique, derive de benzotriazole et de benzimidazole |
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| DE102010003387A1 (de) * | 2010-03-29 | 2011-09-29 | Evonik Degussa Gmbh | Verfahren zur Herstellung von siliciumhaltigen Azodicarbamiden |
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