WO2017063419A1 - Organosilicone chain extender and application - Google Patents
Organosilicone chain extender and application Download PDFInfo
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- WO2017063419A1 WO2017063419A1 PCT/CN2016/090645 CN2016090645W WO2017063419A1 WO 2017063419 A1 WO2017063419 A1 WO 2017063419A1 CN 2016090645 W CN2016090645 W CN 2016090645W WO 2017063419 A1 WO2017063419 A1 WO 2017063419A1
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- carbon atoms
- alkyl group
- chain extender
- alkyl
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- 239000004970 Chain extender Substances 0.000 title claims abstract description 38
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 63
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 125000003118 aryl group Chemical group 0.000 claims abstract description 15
- 229920002379 silicone rubber Polymers 0.000 claims abstract description 11
- 239000004945 silicone rubber Substances 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 5
- 229920001296 polysiloxane Polymers 0.000 claims description 25
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical group OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 9
- 125000003368 amide group Chemical group 0.000 claims description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
- 150000001924 cycloalkanes Chemical class 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims description 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000005343 heterocyclic alkyl group Chemical group 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 13
- 230000000694 effects Effects 0.000 description 12
- 150000002431 hydrogen Chemical class 0.000 description 10
- -1 ketone oxime Chemical class 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 239000003208 petroleum Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000000921 elemental analysis Methods 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000003566 sealing material Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 239000012295 chemical reaction liquid Substances 0.000 description 5
- XGLLBUISUZEUMW-UHFFFAOYSA-N chloromethyl-diethoxy-methylsilane Chemical compound CCO[Si](C)(CCl)OCC XGLLBUISUZEUMW-UHFFFAOYSA-N 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- ZYBZYDVRLQSWGG-UHFFFAOYSA-N 2,2-dimethyloct-7-enoic acid Chemical compound OC(=O)C(C)(C)CCCCC=C ZYBZYDVRLQSWGG-UHFFFAOYSA-N 0.000 description 4
- GAURFLBIDLSLQU-UHFFFAOYSA-N diethoxy(methyl)silicon Chemical compound CCO[Si](C)OCC GAURFLBIDLSLQU-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000565 sealant Substances 0.000 description 4
- WHIVNJATOVLWBW-PLNGDYQASA-N (nz)-n-butan-2-ylidenehydroxylamine Chemical compound CC\C(C)=N/O WHIVNJATOVLWBW-PLNGDYQASA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- 230000001588 bifunctional effect Effects 0.000 description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 0 *N(*)C[Si](*)(*)* Chemical compound *N(*)C[Si](*)(*)* 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 229920005601 base polymer Polymers 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 2
- ZXZMFKUGAPMMCJ-UHFFFAOYSA-N chloromethyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(CCl)OC ZXZMFKUGAPMMCJ-UHFFFAOYSA-N 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 150000004759 cyclic silanes Chemical class 0.000 description 2
- JZLCKKKUCNYLDU-UHFFFAOYSA-N decylsilane Chemical compound CCCCCCCCCC[SiH3] JZLCKKKUCNYLDU-UHFFFAOYSA-N 0.000 description 2
- JAYBZWYBCUJLNQ-UHFFFAOYSA-N dichloro-(chloromethyl)-methylsilane Chemical compound C[Si](Cl)(Cl)CCl JAYBZWYBCUJLNQ-UHFFFAOYSA-N 0.000 description 2
- PKTOVQRKCNPVKY-UHFFFAOYSA-N dimethoxy(methyl)silicon Chemical compound CO[Si](C)OC PKTOVQRKCNPVKY-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- ZLNAFSPCNATQPQ-UHFFFAOYSA-N ethenyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C=C ZLNAFSPCNATQPQ-UHFFFAOYSA-N 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 229920001174 Diethylhydroxylamine Polymers 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical group CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- ICXXXLGATNSZAV-UHFFFAOYSA-N butylazanium;chloride Chemical compound [Cl-].CCCC[NH3+] ICXXXLGATNSZAV-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000027832 depurination Effects 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- FVCOIAYSJZGECG-UHFFFAOYSA-N diethylhydroxylamine Chemical compound CCN(O)CC FVCOIAYSJZGECG-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/544—Silicon-containing compounds containing nitrogen
Definitions
- the invention belongs to the field of polymer organic materials, and particularly relates to a silicone chain extender and an application thereof.
- Low modulus, high elongation silicone sealing materials have excellent bonding properties, high deformation properties under low stress, excellent high temperature resistance, weather resistance, etc., and gap filling connections in roads, bridges, airport runways, etc.
- a bifunctional chain extender matched with a silicone sealing material is selected to control the crosslinking speed, thereby achieving a decrease in modulus and elongation after curing of the sealant. The rate increases the effect.
- US5053442 uses a bifunctional alkoxysilane as a chain extender to produce a low modulus silicone sealing material, but the material has poor storage and long curing time.
- US3996184, US4978706, US5246980, CN1597828, CN1618915 use amidosilane as a chain extender to obtain a low modulus silicone sealing material.
- the amide easily bleeds out of the surface after curing, resulting in reduced adhesion, seal failure, and environmental pollution. , limiting its scope of use.
- CN1597828 uses a bifunctional ketooxime silane as a chain extender to prepare a low modulus silicone sealing material, but the base polymer used in the process still needs a high viscosity base polymer, and the ketone oxime type chain extender activity The problem of long drying time and low elongation of the sealant is low. The activity of the dealcoholized chain extender is very low, and no application in silicone rubber has been reported.
- the silane chain extender used at home and abroad is mainly a deamidated chain extender, so that the amide substance produced after curing tends to pollute the environment. Therefore, the purpose of the present invention is to provide a silicone chain extender with adjustable activity and to be used in silicone rubber, which can be used for the preparation of low modulus sealant, which can significantly improve the elongation of the sealant without reducing the silicon. The adhesion of rubber without polluting the environment.
- the object of the present invention is to provide a novel silicone chain extender which has adjustable activity, including depurination type, dealcoholization type, dehydroxylamine type, etc., on the one hand, by improving the type of hydrolysis group
- the activity is active, while on the other hand the activity of the compound is controlled by changing the organic groups on the ammonia.
- the invention is based on the introduction of an electron withdrawing group, a carbonyl compound (ester group, urea group) or an electron donating group such as diethyl, phenyl, etc. in the nitrogen atom of the a-aminomethylsilane chain extender, which greatly increases the expansion.
- the activity of the chain agent on the other hand, by using different hydrolyzable groups, such as mercapto groups, alcohols, hydroxylamines, etc., further adjusting the activity of the chain extender, making it more active than the cross-linking agent, and being applied to the silicone rubber, Significantly increase the elongation of silicone rubber.
- the present invention provides a silicone chain extender having the structure of Formula I:
- R 1 is an alkyl group having 1 to 6 carbon atoms
- R 4 is selected from the group consisting of hydrogen, an alkyl group, an aryl group, a formate group-containing group, an amide group-containing group or a heterocycloalkyl group;
- R 5 is selected from hydrogen, an alkyl group, an aryl group, a formate group-containing group, an amide group-containing group or a heterocycloalkyl group; and R 4 and R 5 are the same or different;
- R 6 , R 7 , R 8 or R 9 is an alkyl group or a cyclic alkyl group.
- R 1 is a linear alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 1 to 6 carbon atoms, and a cyclic alkane having 1 to 6 carbon atoms.
- R 4 or R 5 is a group containing a formate group, and the group has the structure of the formula II: Formula II wherein R 10 is an alkyl group having 1 to 18 carbon atoms.
- R 4 or R 5 is an amide group-containing group having the structure of the formula III: Formula III wherein R 11 or R 12 is selected from the group consisting of hydrogen, an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 carbon atoms, and a benzyl group.
- R 4 or R 5 is a heterocycloalkyl group having the structure of the formula IV: Formula IV wherein R 13 is an alkyl group having 1 to 12 carbon atoms, and the alkyl group is one of a linear alkyl group, a branched alkyl group, and a cyclic alkane.
- the R 13 is an alkyl group having 1 to 12 carbon atoms, and the alkyl segment contains one or more of N, O, S or a carbonyl group and a hydroxyl group.
- the R 4 or R 5 is selected from the group consisting of pyrrole, imidazole, oxazole, piperidine, morpholine and oxazine.
- the R 4 or R 5 is selected from one of hydrogen, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, phenyl, benzyl.
- R 10 is selected from one of methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, benzyl, dodecyl and octadecyl.
- R 10 is selected from one of methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, benzyl, dodecyl and octadecyl.
- the invention also provides the use of the silicone chain extender in silicone rubber.
- R 1 is an alkyl group having 1 to 6 carbon atoms
- R 4 is selected from the group consisting of hydrogen, an alkyl group, an aryl group, a formate group-containing group, an amide group-containing group or a heterocycloalkyl group;
- R 5 is selected from hydrogen, an alkyl group, an aryl group, a formate group-containing group, an amide group-containing group or a heterocycloalkyl group; and R 4 and R 5 are the same or different;
- R 6 , R 7 , R 8 or R 9 is an alkyl group or a cyclic alkyl group.
- R 1 is a linear alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 1 to 6 carbon atoms, a ring having 1 to 6 carbon atoms One of an alkane, an aromatic alkyl group having 1 to 6 carbon atoms or an alkanearyl group having 1 to 6 carbon atoms.
- said R 1 is selected from the group consisting of methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl; in accordance with a preferred embodiment of the invention, The R 1 is selected from one of a methyl group and an ethyl group.
- R 2 or R 3 is selected from an alkyl group having 1 to 6 carbon atoms, and specifically R 2 or R 3 is selected from the group consisting of methyl, ethyl, n-propyl and n-butyl groups.
- R 2 or R 3 is methyl, ethyl, n-propyl or n-butyl.
- the R 6 or R 7 is selected from one of a methyl group, an ethyl group, a propyl group, a butyl group, an isopropyl group, an isobutyl group, and a cyclic silane.
- said R 6 or R 7 is selected from one of methyl, ethyl, n-propyl and n-butyl.
- R 2 or R 3 is -NR 8 (R 9 ), wherein R 8 and R 9 are alkyl or cyclic alkyl.
- R 8 or R 9 is selected from one of a methyl group, an ethyl group, a propyl group, a butyl group, an isopropyl group, an isobutyl group, and a cyclic silane.
- said R 8 or R 9 7 is selected from one of methyl, ethyl, n-propyl and n-butyl.
- said R 4 or R 5 is selected from the group consisting of hydrogen, alkyl, aryl; according to a more specific embodiment of the invention, said R 4 or R 5 is selected from the group consisting of hydrogen, methyl, One of ethyl, n-propyl, n-butyl, isopropyl, isobutyl, phenyl, benzyl. According to a preferred embodiment of the invention, said R 4 or R 5 is selected from propyl or n-butyl.
- said R 4 or R 5 is a formate group-containing group having the structure of formula II: Formula II wherein R 10 is an alkyl group having 1 to 18 carbon atoms.
- R 10 is selected from the group consisting of methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, benzyl, dodecyl, octadecyl One kind.
- said R 10 is methyl or ethyl.
- said R 4 or R 5 is an amide group-containing group having the structure of formula III: Formula III wherein R 11 or R 12 is selected from the group consisting of hydrogen, an alkyl group having 1 to 18 carbon atoms, an aryl group, and a benzyl group. According to a preferred embodiment of the invention, said R 11 or R 12 is selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, aryl, benzyl, twelve One of the alkyl groups. According to a more preferred embodiment of the invention, said R 11 or R 12 is hydrogen.
- said R 4 or R 5 is heterocycloalkyl, said heterocycloalkyl having the structure of formula IV: Formula IV wherein R 13 is an alkyl group having 1 to 12 carbon atoms, and the alkyl group is one of a linear alkyl group, a branched alkyl group, and a cyclic alkane.
- the R 13 is an alkyl group having 1 to 12 carbon atoms, and the alkyl segment contains one or more of N, O, S or a carbonyl group and a hydroxyl group.
- said R 4 or R 5 is selected from the group consisting of pyrrole, imidazole, oxazole, piperidine, morpholine, oxazine. According to a preferred embodiment of the invention, said R 4 or R 5 is morpholine.
- the silicone rubber chain extender tests the silicone rubber elongation as follows:
- the nanofiller is a fumed silica having a specific surface area of 300 m 2 /g, and the crosslinking agent is methyltributyrin mercaptosilane or methyltrimethoxysilane.
- the catalyst is dibutyltin dilaurate, and the plasticizer is ⁇ , ⁇ -dimethylpolydimethylsiloxane.
- the invention has the following beneficial effects:
- the silicone chain extender of the invention has high activity, and is first extended and crosslinked in the curing process, and the elongation of the chain extender applied to the silicone rubber is 430-820%.
- anhydrous ethanol may be replaced by a different combination of one or more of methanol, propanol, isopropanol, butanol, isobutanol, butanone oxime, and N,N-diethylhydroxylamine.
- reaction liquid was distilled to remove low-boiling substances, and a product of 212-218 ° C / 6 mmHg was collected to obtain a pale yellow transparent N-n-propyl-N-amido- ⁇ -(aminomethyl)methyldimethoxysilane 92.3 g. Product, yield 41.9%.
- the chain extenders obtained in Examples 1 to 7 were applied to silicone rubber with methylvinyldimethoxysilane, methylvinyldibutanonesulfonylsilane and methylvinyldihexanoylaminosilane.
- the elongation at break and tensile strength of the procedure described in the Summary of the Invention are shown in Table 1.
- Example 4 820% 1.30
- Example 5 580% 1.40
- Example 6 620% 1.39
- Example 7 480% 1.42 Methylvinyldimethoxysilane 230% 1.56
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Abstract
Disclosed is an organosilicone chain extender. The organosilicone chain extender has a structure of formula I, R1 being alkyl containing 1 to 6 carbon atoms, R2 being one selected from alkyl containing 1 to 6 carbon atoms, -N=CR6(R7) and -NR8(R9), R3 being one selected from alkyl containing 1 to 6 carbon atoms, -N=CR6(R7) and -NR8(R9), R2 and R3 being same or different, R4 or R5 being one selected from hydrogen, alkyl, aryl, a perssad containing a formiate base, a perssad containing an acylamino or heterocyclic alkyl, R4 and R5 being same or different, and R6, R7, R8 or R9 being alkyl or cyclic alkyl. After the chain extender is applied to silicone rubber, the elongation is 430% to 820%.
Description
本发明属于高分子有机材料领域,具体涉及一种有机硅扩链剂及其应用。The invention belongs to the field of polymer organic materials, and particularly relates to a silicone chain extender and an application thereof.
低模量、高伸长率有机硅密封材料具有优异的粘接性能、低应力下高形变性能、优异的耐高低温、耐候性等性能,在道路、桥梁、机场跑道等场合的缝隙填充连接中有广泛的应用。为了制备低模量有机硅密封材料,一般需要降低交联度,选用与有机硅密封材料相匹配的二官能团扩链剂来控制交联速度,从而达到密封胶固化后的模量下降、伸长率增加的效果。Low modulus, high elongation silicone sealing materials have excellent bonding properties, high deformation properties under low stress, excellent high temperature resistance, weather resistance, etc., and gap filling connections in roads, bridges, airport runways, etc. There are a wide range of applications. In order to prepare a low modulus silicone sealing material, it is generally required to reduce the degree of crosslinking, and a bifunctional chain extender matched with a silicone sealing material is selected to control the crosslinking speed, thereby achieving a decrease in modulus and elongation after curing of the sealant. The rate increases the effect.
US5053442以双官能的烷氧基硅烷为扩链剂,制得低模量有机硅密封材料,但该材料存储性差,固化时间长。US3996184、US4978706、US5246980、CN1597828、CN1618915以酰氨基硅烷为扩链剂,制得低模量有机硅密封材料,由于固化后该酰胺易渗出表面,造成粘接力降低,密封失效,同时环境污染,限制了其使用范围。CN1597828以双官能的酮肟硅烷为扩链剂,制备得到低模量有机硅密封材料,但工艺中所采用的基础聚合物仍需用高粘度的基础聚合物,且酮肟型扩链剂活性较低存在表干时间长、密封胶伸长率低的问题,脱醇型扩链剂由于活性很低,未见在硅橡胶中应用的报道。US5053442 uses a bifunctional alkoxysilane as a chain extender to produce a low modulus silicone sealing material, but the material has poor storage and long curing time. US3996184, US4978706, US5246980, CN1597828, CN1618915 use amidosilane as a chain extender to obtain a low modulus silicone sealing material. The amide easily bleeds out of the surface after curing, resulting in reduced adhesion, seal failure, and environmental pollution. , limiting its scope of use. CN1597828 uses a bifunctional ketooxime silane as a chain extender to prepare a low modulus silicone sealing material, but the base polymer used in the process still needs a high viscosity base polymer, and the ketone oxime type chain extender activity The problem of long drying time and low elongation of the sealant is low. The activity of the dealcoholized chain extender is very low, and no application in silicone rubber has been reported.
目前,国内外使用的硅烷扩链剂以脱酰胺型扩链剂为主,使固化后产生的酰胺物质易污染环境。因此本方明的目的在于提供活性可调的有机硅扩链剂,并应用于有机硅橡胶中,可用于低模量密封胶的制备,可显著提高密封胶的伸长率,不会降低硅橡胶的粘接力,同时不会污染环境。At present, the silane chain extender used at home and abroad is mainly a deamidated chain extender, so that the amide substance produced after curing tends to pollute the environment. Therefore, the purpose of the present invention is to provide a silicone chain extender with adjustable activity and to be used in silicone rubber, which can be used for the preparation of low modulus sealant, which can significantly improve the elongation of the sealant without reducing the silicon. The adhesion of rubber without polluting the environment.
发明内容
Summary of the invention
本发明的目的是提供一种新型有机硅扩链剂,该有机硅扩链剂的活性可调,包括脱肟型、脱醇型、脱羟胺型等,一方面通过改进水解基团的种类调节反应活性,而另一方面通过改变氨上的有机基团来控制化合物的活性。The object of the present invention is to provide a novel silicone chain extender which has adjustable activity, including depurination type, dealcoholization type, dehydroxylamine type, etc., on the one hand, by improving the type of hydrolysis group The activity is active, while on the other hand the activity of the compound is controlled by changing the organic groups on the ammonia.
本发明是基于在a-氨甲基硅烷扩链剂的氮原子引入吸电子基团,羰基化合物(酯基、脲基)或供电子基团,如二乙基、苯基等,大幅提升扩链剂的活性,另一方面,通过采用不同的水解基团,如肟基、醇、羟胺等,进一步调节扩链剂的活性,使其活性高于交联剂,应用在硅橡胶中,可显著提升硅橡胶的伸长率。The invention is based on the introduction of an electron withdrawing group, a carbonyl compound (ester group, urea group) or an electron donating group such as diethyl, phenyl, etc. in the nitrogen atom of the a-aminomethylsilane chain extender, which greatly increases the expansion. The activity of the chain agent, on the other hand, by using different hydrolyzable groups, such as mercapto groups, alcohols, hydroxylamines, etc., further adjusting the activity of the chain extender, making it more active than the cross-linking agent, and being applied to the silicone rubber, Significantly increase the elongation of silicone rubber.
为了达到上述的技术效果,本发明采取以下技术方案:In order to achieve the above technical effects, the present invention adopts the following technical solutions:
本发明提供了一种有机硅扩链剂,具有式I的结构:The present invention provides a silicone chain extender having the structure of Formula I:
R1为含1-6个碳原子的烷基;R 1 is an alkyl group having 1 to 6 carbon atoms;
R2选自含1-6个碳原子的烷基、-N=CR6(R7)、-NR8(R9)中的一种;R 2 is selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, -N=CR 6 (R 7 ), and -NR 8 (R 9 );
R3选自含1-6个碳原子的烷基、-N=CR6(R7)、-NR8(R9)中的一种;R2、R3相同或不同;R 3 is selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, -N=CR 6 (R 7 ), and -NR 8 (R 9 ); and R 2 and R 3 are the same or different;
R4选自氢、烷基、芳基、含甲酸酯基的基团、含酰胺基的基团或杂环烷基中的一种;R 4 is selected from the group consisting of hydrogen, an alkyl group, an aryl group, a formate group-containing group, an amide group-containing group or a heterocycloalkyl group;
R5选自氢、烷基、芳基、含甲酸酯基的基团、含酰胺基的基团或杂环烷基中的一种;R4、R5相同或不同;R 5 is selected from hydrogen, an alkyl group, an aryl group, a formate group-containing group, an amide group-containing group or a heterocycloalkyl group; and R 4 and R 5 are the same or different;
R6、R7、R8或R9为烷基或环状烷基。R 6 , R 7 , R 8 or R 9 is an alkyl group or a cyclic alkyl group.
进一步的技术方案是,所述的R1为含1-6个碳原子的直链烷基、含1-6个
碳原子的带支链烷基、含1-6个碳原子的环状烷烃、含1-6个碳原子的芳香烷基或含1-6个碳原子的烷烃芳基中的一种。A further technical solution is that R 1 is a linear alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 1 to 6 carbon atoms, and a cyclic alkane having 1 to 6 carbon atoms. One of an aromatic alkyl group having 1 to 6 carbon atoms or an alkanearyl group having 1 to 6 carbon atoms.
进一步的技术方案是,所述的R4或R5为含甲酸酯基的基团,该基团具有式II的结构:式II,其中,R10为含1~18个碳原子的烷基。In a further technical solution, the R 4 or R 5 is a group containing a formate group, and the group has the structure of the formula II: Formula II wherein R 10 is an alkyl group having 1 to 18 carbon atoms.
进一步的技术方案是,所述的R4或R5为含酰胺基的基团,该基团具有式III的结构:式III,其中,R11或R12选自氢、含1~18个碳原子的烷基、含6~18个碳原子的芳基、苄基中的一种。In a further technical solution, the R 4 or R 5 is an amide group-containing group having the structure of the formula III: Formula III wherein R 11 or R 12 is selected from the group consisting of hydrogen, an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 carbon atoms, and a benzyl group.
进一步的技术方案是,所述的R4或R5为杂环烷基,该杂环烷基具有式IV的结构:式IV,其中,R13为含1~12个碳原子的烷基,所述的烷基为直链烷基、带支链烷基、环状烷烃中的一种。In a further technical solution, the R 4 or R 5 is a heterocycloalkyl group having the structure of the formula IV: Formula IV wherein R 13 is an alkyl group having 1 to 12 carbon atoms, and the alkyl group is one of a linear alkyl group, a branched alkyl group, and a cyclic alkane.
进一步的技术方案是,所述的R13为含1~12个碳原子的烷基,烷基链段中含有N、O、S或羰基、羟基中的一种或多种。In a further technical solution, the R 13 is an alkyl group having 1 to 12 carbon atoms, and the alkyl segment contains one or more of N, O, S or a carbonyl group and a hydroxyl group.
进一步的技术方案是,所述的R4或R5选自吡咯、咪唑、噁唑、哌啶、吗啉、噁嗪中的一种。In a further technical solution, the R 4 or R 5 is selected from the group consisting of pyrrole, imidazole, oxazole, piperidine, morpholine and oxazine.
进一步的技术方案是,所述的R4或R5选自氢、甲基、乙基、正丙基、正丁基、异丙基、异丁基、苯基、苄基中的一种。In a further technical solution, the R 4 or R 5 is selected from one of hydrogen, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, phenyl, benzyl.
进一步的技术方案是,所述的R10选自甲基、乙基、正丙基、正丁基、异丙基、异丁基、苄基、十二烷基、十八烷基中的一种。A further technical solution is that R 10 is selected from one of methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, benzyl, dodecyl and octadecyl. Kind.
本发明还提供了所述的有机硅扩链剂在硅橡胶中的应用。The invention also provides the use of the silicone chain extender in silicone rubber.
下面对本发明做进一步的说明。The invention will be further described below.
一种有机硅扩链剂,具有式I的结构:
A silicone chain extender having the structure of Formula I:
R1为含1-6个碳原子的烷基;R 1 is an alkyl group having 1 to 6 carbon atoms;
R2选自含1-6个碳原子的烷基、-N=CR6(R7)、-NR8(R9)中的一种;R 2 is selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, -N=CR 6 (R 7 ), and -NR 8 (R 9 );
R3选自含1-6个碳原子的烷基、-N=CR6(R7)、-NR8(R9)中的一种;R2、R3相同或不同;R 3 is selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, -N=CR 6 (R 7 ), and -NR 8 (R 9 ); and R 2 and R 3 are the same or different;
R4选自氢、烷基、芳基、含甲酸酯基的基团、含酰胺基的基团或杂环烷基中的一种;R 4 is selected from the group consisting of hydrogen, an alkyl group, an aryl group, a formate group-containing group, an amide group-containing group or a heterocycloalkyl group;
R5选自氢、烷基、芳基、含甲酸酯基的基团、含酰胺基的基团或杂环烷基中的一种;R4、R5相同或不同;R 5 is selected from hydrogen, an alkyl group, an aryl group, a formate group-containing group, an amide group-containing group or a heterocycloalkyl group; and R 4 and R 5 are the same or different;
R6、R7、R8或R9为烷基或环状烷基。R 6 , R 7 , R 8 or R 9 is an alkyl group or a cyclic alkyl group.
根据本发明的具体实施例,所述的R1为含1-6个碳原子的直链烷基、含1-6个碳原子的带支链烷基、含1-6个碳原子的环状烷烃、含1-6个碳原子的芳香烷基或含1-6个碳原子的烷烃芳基中的一种。根据本发明更具体的实施例,所述的R1选自甲基、乙基、正丙基、正丁基、异丙基、异丁基中的一种;根据本发明优选的实施例,所述的R1选自甲基、乙基中的一种。According to a particular embodiment of the invention, R 1 is a linear alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 1 to 6 carbon atoms, a ring having 1 to 6 carbon atoms One of an alkane, an aromatic alkyl group having 1 to 6 carbon atoms or an alkanearyl group having 1 to 6 carbon atoms. According to a more specific embodiment of the invention, said R 1 is selected from the group consisting of methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl; in accordance with a preferred embodiment of the invention, The R 1 is selected from one of a methyl group and an ethyl group.
在本发明的实施例中,所述的R2或R3选自含1-6个碳原子的烷基、-N=CR6(R7)、-NR8(R9)中的一种。进一步的技术方案是,R2或R3选自含1-6个碳原子的烷基,具体为所述的R2或R3选自甲基、乙基、正丙基、正丁基、异丙基、异丁基、苯基、苄基中的一种。根据本发明的更优选实施例,所述的R2或R3为甲基、乙基、正丙基、正丁基。In an embodiment of the invention, the R 2 or R 3 is selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, -N=CR 6 (R 7 ), and -NR 8 (R 9 ) . A further technical solution is that R 2 or R 3 is selected from an alkyl group having 1 to 6 carbon atoms, and specifically R 2 or R 3 is selected from the group consisting of methyl, ethyl, n-propyl and n-butyl groups. One of isopropyl, isobutyl, phenyl, benzyl. According to a more preferred embodiment of the invention, said R 2 or R 3 is methyl, ethyl, n-propyl or n-butyl.
进一步的技术方案是,R2或R3为-N=CR6(R7),其中R6、R7为烷基或环状
烷基。根据本发明具体的实施例,所述的R6或R7选自甲基、乙基、丙基、丁基、异丙基、异丁基、环状硅烷中的一种。根据本发明的更优选实施例,所述的R6或R7选自甲基、乙基、正丙基、正丁基中的一种。A further technical solution is that R 2 or R 3 is -N=CR 6 (R 7 ), wherein R 6 and R 7 are alkyl or cyclic alkyl. According to a particular embodiment of the invention, the R 6 or R 7 is selected from one of a methyl group, an ethyl group, a propyl group, a butyl group, an isopropyl group, an isobutyl group, and a cyclic silane. According to a more preferred embodiment of the invention, said R 6 or R 7 is selected from one of methyl, ethyl, n-propyl and n-butyl.
进一步的技术方案是,R2或R3为-NR8(R9),其中R8、R9为烷基或环状烷基。根据本发明具体的实施例,所述的R8或R9选自甲基、乙基、丙基、丁基、异丙基、异丁基、环状硅烷中的一种。根据本发明的更优选实施例,所述的R8或R97选自甲基、乙基、正丙基、正丁基中的一种。根据本发明的具体实施例,所述的R4或R5选自氢、烷基、芳基;根据本发明更具体的实施例,所述的R4或R5选自氢、甲基、乙基、正丙基、正丁基、异丙基、异丁基、苯基、苄基中的一种。根据本发明的优选实施例,所述的R4或R5选自丙基或正丁基。A further technical solution is that R 2 or R 3 is -NR 8 (R 9 ), wherein R 8 and R 9 are alkyl or cyclic alkyl. According to a particular embodiment of the invention, the R 8 or R 9 is selected from one of a methyl group, an ethyl group, a propyl group, a butyl group, an isopropyl group, an isobutyl group, and a cyclic silane. According to a more preferred embodiment of the invention, said R 8 or R 9 7 is selected from one of methyl, ethyl, n-propyl and n-butyl. According to a particular embodiment of the invention, said R 4 or R 5 is selected from the group consisting of hydrogen, alkyl, aryl; according to a more specific embodiment of the invention, said R 4 or R 5 is selected from the group consisting of hydrogen, methyl, One of ethyl, n-propyl, n-butyl, isopropyl, isobutyl, phenyl, benzyl. According to a preferred embodiment of the invention, said R 4 or R 5 is selected from propyl or n-butyl.
根据本发明的具体实施例,所述的R4或R5为含甲酸酯基的基团,该基团具有式II的结构:式II,其中,R10为含1~18个碳原子的烷基。根据本发明的优选实施例,所述的R10选自甲基、乙基、正丙基、正丁基、异丙基、异丁基、苄基、十二烷基、十八烷基中的一种。根据本发明的更优选实施例,所述的R10为甲基或乙基。According to a particular embodiment of the invention, said R 4 or R 5 is a formate group-containing group having the structure of formula II: Formula II wherein R 10 is an alkyl group having 1 to 18 carbon atoms. According to a preferred embodiment of the invention, said R 10 is selected from the group consisting of methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, benzyl, dodecyl, octadecyl One kind. According to a more preferred embodiment of the invention, said R 10 is methyl or ethyl.
根据本发明的具体实施例,所述的R4或R5为含酰胺基的基团,该基团具有式III的结构:式III,其中,R11或R12选自氢、含1~18个碳原子的烷基、芳基、苄基中的一种。根据本发明的优选实施例,所述的R11或R12选自氢、甲基、乙基、正丙基、正丁基、异丙基、异丁基、芳基、苄基、十二烷基中的一种。根据本发明的更优选实施例,所述的R11或R12为氢。According to a particular embodiment of the invention, said R 4 or R 5 is an amide group-containing group having the structure of formula III: Formula III wherein R 11 or R 12 is selected from the group consisting of hydrogen, an alkyl group having 1 to 18 carbon atoms, an aryl group, and a benzyl group. According to a preferred embodiment of the invention, said R 11 or R 12 is selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, aryl, benzyl, twelve One of the alkyl groups. According to a more preferred embodiment of the invention, said R 11 or R 12 is hydrogen.
根据本发明的具体实施例,所述的R4或R5为杂环烷基,该杂环烷基具有式
IV的结构:式IV,其中,R13为含1~12个碳原子的烷基,所述的烷基为直链烷基、带支链烷基、环状烷烃中的一种。According to a particular embodiment of the invention, said R 4 or R 5 is heterocycloalkyl, said heterocycloalkyl having the structure of formula IV: Formula IV wherein R 13 is an alkyl group having 1 to 12 carbon atoms, and the alkyl group is one of a linear alkyl group, a branched alkyl group, and a cyclic alkane.
根据本发明的具体实施例,所述的R13为含1~12个碳原子的烷基,烷基链段中含有N、O、S或羰基、羟基中的一种或多种。According to a specific embodiment of the present invention, the R 13 is an alkyl group having 1 to 12 carbon atoms, and the alkyl segment contains one or more of N, O, S or a carbonyl group and a hydroxyl group.
根据本发明的具体实施例,所述的R4或R5选自吡咯、咪唑、噁唑、哌啶、吗啉、噁嗪中的一种。根据本发明的优选实施例,所述的R4或R5为吗啉。According to a particular embodiment of the invention, said R 4 or R 5 is selected from the group consisting of pyrrole, imidazole, oxazole, piperidine, morpholine, oxazine. According to a preferred embodiment of the invention, said R 4 or R 5 is morpholine.
在本发明中,有机硅扩链剂对硅橡胶伸长率的测试步骤如下:In the present invention, the silicone rubber chain extender tests the silicone rubber elongation as follows:
α,ω-二羟基聚二甲基硅氧烷200g质量份,纳米填料180质量份,于120℃,真空度0.06Mpa下脱水共混60min.,移入高速分散机内冷至室温制得基料;在室温下将有机硅扩链剂4质量份,交联剂8质量份,催化剂0.1质量份,填料5质量份和增塑剂50质量份加入到真空的搅拌机中搅拌均匀后后出胶,在室温下相对湿度50±5%条件下检测。在发明的测试步骤中,所述的纳米填料为比表面积为300m2/g的气相法白炭黑,所述的交联剂为甲基三丁酮肟基硅烷或甲基三甲氧基硅烷,所述的催化剂为二月桂酸二丁基锡,所述的增塑剂为α,ω-二甲基聚二甲基硅氧烷。200 g parts by mass of α,ω-dihydroxypolydimethylsiloxane, 180 parts by mass of nano-filler, dehydrated and blended at 120 ° C, vacuum degree 0.06 Mpa for 60 min., transferred into a high-speed disperser and cooled to room temperature to obtain a base material. 4 parts by mass of a silicone chain extender, 8 parts by mass of a crosslinking agent, 0.1 parts by mass of a catalyst, 5 parts by mass of a filler, and 50 parts by mass of a plasticizer are added to a vacuum mixer and stirred, and then discharged. Detected at a relative humidity of 50 ± 5% at room temperature. In the testing step of the invention, the nanofiller is a fumed silica having a specific surface area of 300 m 2 /g, and the crosslinking agent is methyltributyrin mercaptosilane or methyltrimethoxysilane. The catalyst is dibutyltin dilaurate, and the plasticizer is α,ω-dimethylpolydimethylsiloxane.
拉伸强度和断裂伸长率按照GT/T 528-2009方法测试。Tensile strength and elongation at break were tested in accordance with the GT/T 528-2009 method.
本发明与现有技术相比,具有以下的有益效果:Compared with the prior art, the invention has the following beneficial effects:
本发明的有机硅扩链剂具有较高的活性,在固化过程中会先扩链后交联,该扩链剂应用于硅橡胶后伸长率为430~820%。The silicone chain extender of the invention has high activity, and is first extended and crosslinked in the curing process, and the elongation of the chain extender applied to the silicone rubber is 430-820%.
下面结合本发明的实施例对本发明作进一步的阐述和说明。The invention is further illustrated and described below in conjunction with the embodiments of the invention.
原料的制备:Preparation of raw materials:
将209.9g(4.58mol)无水乙醇和500mL石油醚加入3L三口烧瓶中,保
持氮气流速为0.1ml/min,在冰水浴中搅拌均匀后,控制内温在10℃左右,然后逐滴加入300g(1.85mol)(氯甲基)甲基二氯硅烷,约1h滴加完毕后在40℃继续反应3h。然后在真空度为0.05Mpa下蒸除溶剂和未反应的乙醇后再常压精馏,收集94-95℃产品,得到无色透明(氯甲基)甲基二乙氧基硅烷320g,收率96%。Add 209.9 g (4.58 mol) of absolute ethanol and 500 mL of petroleum ether to a 3 L three-necked flask.
Hold the nitrogen flow rate at 0.1ml/min, stir evenly in an ice water bath, control the internal temperature at about 10 °C, then add 300g (1.85mol) (chloromethyl)methyldichlorosilane dropwise, about 1h The reaction was then continued at 40 ° C for 3 h. Then, the solvent and the unreacted ethanol were distilled off under a vacuum of 0.05 Mpa, and then subjected to atmospheric distillation, and the product was collected at 94-95 ° C to obtain 320 g of colorless transparent (chloromethyl)methyldiethoxysilane. 96%.
(氯甲基)甲基乙氧基丁酮肟基硅烷的制备Preparation of (chloromethyl)methylethoxybutanone decylsilane
将300g(1.85mol)(氯甲基)甲基二氯硅烷、500ml石油醚和387.2g(3.83mol)三乙胺加入到3L三口烧瓶中,在冰水浴中搅拌均匀后,控制内温在10℃左右,然后逐滴加入85.1g(1.85mol)无水乙醇,约2h滴加完毕后再缓慢滴入161.1g(1.85mol)丁酮肟,约2h滴加完毕后再在40℃继续反应3h。然后在真空度为0.05Mpa下蒸除溶剂和未反应的乙醇和丁酮肟后再精馏,收集93-99℃/10mmHg产品,得到浅黄色透明氯甲基)甲基乙氧基丁酮肟基硅烷310g,收率75.1%。300 g (1.85 mol) of (chloromethyl)methyldichlorosilane, 500 ml of petroleum ether and 387.2 g (3.83 mol) of triethylamine were added to a 3 L three-necked flask, and after stirring evenly in an ice water bath, the internal temperature was controlled at 10 After about °C, 85.1g (1.85mol) of absolute ethanol was added dropwise. After about 2h, the addition of 161.1g (1.85mol) of butanone oxime was slowly added. After about 2h, the reaction was continued at 40 °C for 3 hours. . Then, the solvent and the unreacted ethanol and butanone oxime were distilled off under a vacuum of 0.05 MPa, and then rectified, and 93-99 ° C/10 mmHg product was collected to obtain pale yellow transparent chloromethyl)methyl ethoxybutanone oxime. The base silane was 310 g, and the yield was 75.1%.
根据上述方法无水乙醇可以选用甲醇、丙醇、异丙醇、丁醇、异丁醇、丁酮肟、N,N-二乙基羟胺的一种或多种的不同组合方式代替。According to the above method, anhydrous ethanol may be replaced by a different combination of one or more of methanol, propanol, isopropanol, butanol, isobutanol, butanone oxime, and N,N-diethylhydroxylamine.
实施例1:Example 1:
将290.8g(1.59mol)(氯甲基)甲基二乙氧基硅烷、152.2g(1.75mol)吗啉、178.2g(1.75mol)三乙胺、0.4gKI和800mL石油醚投入3L三口烧瓶中,在氮气保护下60℃反应4h后。过滤除去生成的三乙胺盐酸盐,将滤液旋蒸除溶剂和未反应的三乙胺、吗啉后精馏,收集125-132℃/10mmHg产品,得到橙黄色透明的(吗啉甲基)甲基二乙氧基硅烷294.1g,收率79.4%。290.8 g (1.59 mol) of (chloromethyl)methyldiethoxysilane, 152.2 g (1.75 mol) of morpholine, 178.2 g (1.75 mol) of triethylamine, 0.4 g of KI and 800 mL of petroleum ether were placed in a 3 L three-necked flask. After reacting at 60 ° C for 4 h under nitrogen atmosphere. The resulting triethylamine hydrochloride was removed by filtration, and the filtrate was evaporated to remove the solvent and unreacted triethylamine and morpholine, followed by distillation, and the product was collected at 125-132 ° C/10 mmHg to obtain an orange-yellow transparent (morpholinylmethyl group). 294.1 g of methyldiethoxysilane, the yield was 79.4%.
1H NMR(300MHz,CDCl3),δ3.67(4H),3.60(4H),2.45(4H),2.20(2H),1.10(6H),0.16(3H)
1 H NMR (300MHz, CDCl 3 ), δ 3.67 (4H), 3.60 (4H), 2.45 (4H), 2.20 (2H), 1.10 (6H), 0.16 (3H)
元素分析:C% 51.39,H% 9.88,N% 5.94。Elemental analysis: C% 51.39, H% 9.88, N% 5.94.
实施例2:Example 2:
将132g(0.5mol)(氯甲基)甲基二丁酮肟基硅烷、46.2g(0.53mol)吗啉、53.6g(0.53mol)三乙胺、0.2gKI和300ml石油醚投入1L三口烧瓶中,在氮气保护下75℃下反应6h后,过滤除去生成的三乙胺盐酸盐,将滤液旋转蒸除溶剂和未反应的三乙胺、吗啉后精馏,收集143-150℃/8mmHg产品,得到橙黄色透明的(吗啉甲基)甲基二丁酮肟基硅烷118.2g,收率74.9%。132 g (0.5 mol) of (chloromethyl)methyldibutanone decylsilane, 46.2 g (0.53 mol) of morpholine, 53.6 g (0.53 mol) of triethylamine, 0.2 g of KI and 300 ml of petroleum ether were placed in a 1 L three-necked flask. After reacting at 75 ° C for 6 h under nitrogen atmosphere, the resulting triethylamine hydrochloride was removed by filtration, and the filtrate was rotary evaporated to remove the solvent and unreacted triethylamine and morpholine, followed by distillation to collect 143-150 ° C / 8 mmHg. The product obtained 118.2 g of orange-yellow transparent (morpholinylmethyl)methyldibutanone decylsilane in a yield of 74.9%.
1H NMR(300MHz,CDCl3),δ3.63(4H),2.40(14H),2.18(2H),1.08(6H),0.18(3H) 1 H NMR (300MHz, CDCl 3 ), δ 3.63 (4H), 2.40 (14H), 2.18 (2H), 1.08 (6H), 0.18 (3H)
元素分析:C% 53.31,H% 9.25,N% 13.29。Elemental analysis: C% 53.31, H% 9.25, N% 13.29.
实施例3:Example 3:
将182.1g(1.0mol)(氯甲基)甲基二乙氧基硅烷、124.2g(1.05mol)正丙胺、0.1gKI、300ml石油醚投入1L三口烧瓶中,在氮气保护下75℃下反应8h后,过滤除去生成的正丙胺盐酸盐,将滤液旋转蒸除溶剂和未反应的正丙胺后,加入90g(1.0mol)碳酸二甲酯,在85℃反应2h。将反应液蒸馏除去低沸物和未反应的碳酸二甲酯后,收集185-192℃/6mmHg产品,得到浅黄色透明的N-正丙基-N-甲酸甲酯基-α-(氨甲基)甲基二乙氧基硅烷185.3g产品,收率70.4%。182.1 g (1.0 mol) of (chloromethyl)methyldiethoxysilane, 124.2 g (1.05 mol) of n-propylamine, 0.1 g of KI, 300 ml of petroleum ether were placed in a 1 L three-necked flask, and reacted under nitrogen for 7 h at 75 ° C. Thereafter, the resulting n-propylamine hydrochloride was removed by filtration, and the filtrate was evaporated to remove solvent and unreacted n-propylamine. Then, 90 g (1.0 mol) of dimethyl carbonate was added, and the mixture was reacted at 85 ° C for 2 h. After the reaction liquid was distilled off to remove the low-boiling and unreacted dimethyl carbonate, the product was collected at 185-192 ° C / 6 mmHg to obtain a pale yellow transparent N-n-propyl-N-carboxymethyl ester-α- (carbamoyl) 18) g of methyl diethoxysilane product, the yield was 70.4%.
1H NMR(300MHz,CDCl3),δ3.75(7H),2.83(2H),2.15(2H),1.58(2H),1.13(6H),0.85(3H),0.20(3H) 1 H NMR (300MHz, CDCl 3 ), δ3.75 (7H), 2.83 (2H), 2.15 (2H), 1.58 (2H), 1.13 (6H), 0.85 (3H), 0.20 (3H)
元素分析:C% 50.10,H% 9.53,N% 5.30。Elemental analysis: C% 50.10, H% 9.53, N% 5.30.
实施例4:Example 4:
将154g(1.0mol)(氯甲基)甲基二甲氧基硅烷、124.2g(1.05mol)正丙胺、0.1gKI、300ml石油醚投入1L三口烧瓶中,在氮气保护下75℃下反应8h后,
过滤除去生成的正丙胺盐酸盐,将滤液旋转蒸除溶剂和未反应的正丙胺后,加入90g(1.0mol)碳酸二甲酯,在85℃反应2h。将反应液蒸馏除去低沸物和未反应的碳酸二甲酯后,收集178-184℃/6mmHg产品,得到浅黄色透明的N-正丙基-N-甲酸甲酯基-α-(氨甲基)甲基二甲氧基硅烷179.1g产品,收率76.2%。154 g (1.0 mol) of (chloromethyl)methyldimethoxysilane, 124.2 g (1.05 mol) of n-propylamine, 0.1 g of KI, 300 ml of petroleum ether were placed in a 1 L three-necked flask, and reacted at 75 ° C for 8 h under a nitrogen atmosphere. ,
The resulting n-propylamine hydrochloride was removed by filtration, and the filtrate was evaporated to remove solvent and unreacted n-propylamine. Then, 90 g (1.0 mol) of dimethyl carbonate was added and reacted at 85 ° C for 2 h. After the reaction liquid was distilled off to remove the low-boiling and unreacted dimethyl carbonate, the product was collected at 178-184 ° C / 6 mmHg to obtain a pale yellow transparent N-n-propyl-N-formic acid methyl ester-α- (carbamoyl) 179.1 g of methyl dimethoxysilane, the yield was 76.2%.
1H NMR(300MHz,CDCl3),δ3.82(3H),3.68(6H),2.78(2H),2.18(2H),1.56(2H),0.87(3H),0.18(3H) 1 H NMR (300MHz, CDCl 3 ), δ3.82 (3H), 3.68 (6H), 2.78 (2H), 2.18 (2H), 1.56 (2H), 0.87 (3H), 0.18 (3H)
元素分析:C% 45.89,H% 8.95,N% 6.02。Elemental analysis: C% 45.89, H% 8.95, N% 6.02.
实施例5:Example 5:
将182.1g(1.0mol)(氯甲基)甲基二乙氧基硅烷、76.8g(1.05mol)正丁胺、0.1gKI、300ml石油醚投入1L三口烧瓶中,在氮气保护下75℃下反应8h后,过滤除去生成的正丁胺盐酸盐,将滤液旋转蒸除溶剂和未反应的正丁胺后,加入90g(1.0mol)碳酸二甲酯,在85℃反应2h。将反应液蒸馏除去低沸物和未反应的碳酸二甲酯后,收集190-196℃/6mmHg产品,得到浅黄色透明的N-正丁基-N-甲酸甲酯基-α-(氨甲基)甲基二乙氧基硅烷150.3g产品,收率54.2%。182.1 g (1.0 mol) of (chloromethyl)methyldiethoxysilane, 76.8 g (1.05 mol) of n-butylamine, 0.1 g of KI, 300 ml of petroleum ether were placed in a 1 L three-necked flask and reacted at 75 ° C under nitrogen atmosphere. After 8 h, the resulting n-butylamine hydrochloride was removed by filtration, and the solvent was evaporated to remove solvent and unreacted n-butylamine. Then, 90 g (1.0 mol) of dimethyl carbonate was added and reacted at 85 ° C for 2 h. After the reaction liquid was distilled off to remove low-boiling and unreacted dimethyl carbonate, the product was collected at 190-196 ° C / 6 mmHg to obtain a pale yellow transparent N-n-butyl-N-formic acid methyl ester-α- (carbamoyl) 150.3 g of methyldiethoxysilane product, the yield was 54.2%.
1H NMR(300MHz,CDCl3),δ3.75(7H),2.83(2H),2.15(2H),1.54(2H),1.34(2H),1.13(6H),0.85(3H),0.20(3H) 1 H NMR (300MHz, CDCl 3 ), δ3.75 (7H), 2.83 (2H), 2.15 (2H), 1.54 (2H), 1.34 (2H), 1.13 (6H), 0.85 (3H), 0.20 (3H )
元素分析:C% 51.60,H% 9.80,N% 5.02。Elemental analysis: C% 51.60, H% 9.80, N% 5.02.
实施例6:Example 6
将182.1g(1.0mol)(氯甲基)甲基二乙氧基硅烷、124.2g(1.05mol)正丙胺、0.1gKI、300ml石油醚投入1L三口烧瓶中,在氮气保护下75℃下反应8h后,过滤除去生成的正丙胺盐酸盐,将滤液旋转蒸除溶剂和未反应的正丙胺后,加入118.1g(1.0mol)碳酸二乙酯,在90℃反应2h。将反应液蒸馏除去低沸物和未反应的碳酸二乙酯后,收集193-198℃/6mmHg产品,得到浅黄色透明的N-
正丙基-N-甲酸乙酯基-α-(氨甲基)甲基二乙氧基硅烷128.3g产品,收率46.3%。182.1 g (1.0 mol) of (chloromethyl)methyldiethoxysilane, 124.2 g (1.05 mol) of n-propylamine, 0.1 g of KI, 300 ml of petroleum ether were placed in a 1 L three-necked flask, and reacted under nitrogen for 7 h at 75 ° C. Thereafter, the resulting n-propylamine hydrochloride was removed by filtration, and the filtrate was evaporated to remove solvent and unreacted n-propylamine. Then, 118.1 g (1.0 mol) of diethyl carbonate was added and reacted at 90 ° C for 2 h. After the reaction liquid was distilled off to remove low-boiling and unreacted diethyl carbonate, 193-198 ° C / 6 mmHg product was collected to obtain a pale yellow transparent N-
n-propyl-N-carboxylate-α-(aminomethyl)methyldiethoxysilane 128.3 g product, yield 46.3%.
1H NMR(300MHz,CDCl3),δ3.93(6H),2.75(2H),2.20(2H),1.48(11H),0.89(3H),0.17(3H) 1 H NMR (300MHz, CDCl 3 ), δ 3.93 (6H), 2.75 (2H), 2.20 (2H), 1.48 (11H), 0.89 (3H), 0.17 (3H)
元素分析:C% 51.92,H% 9.78,N% 5.02。Elemental analysis: C% 51.92, H% 9.78, N% 5.02.
实施例7:Example 7
将154g(1.0mol)(氯甲基)甲基二甲氧基硅烷、124.2g(1.05mol)正丙胺、0.1gKI、300ml石油醚投入1L三口烧瓶中,在氮气保护下75℃下反应8h后,过滤除去生成的正丙胺盐酸盐,将滤液旋转蒸除溶剂和未反应的正丙胺后,加入60g(1.0mol)尿素,在90℃反应3h。将反应液蒸馏除去低沸物,收集212-218℃/6mmHg产品,得到浅黄色透明的N-正丙基-N-酰胺基-α-(氨甲基)甲基二甲氧基硅烷92.3g产品,收率41.9%。154 g (1.0 mol) of (chloromethyl)methyldimethoxysilane, 124.2 g (1.05 mol) of n-propylamine, 0.1 g of KI, 300 ml of petroleum ether were placed in a 1 L three-necked flask, and reacted at 75 ° C for 8 h under a nitrogen atmosphere. The resulting n-propylamine hydrochloride was removed by filtration, and the filtrate was evaporated to remove solvent and unreacted n-propylamine. Then, 60 g (1.0 mol) of urea was added and reacted at 90 ° C for 3 h. The reaction liquid was distilled to remove low-boiling substances, and a product of 212-218 ° C / 6 mmHg was collected to obtain a pale yellow transparent N-n-propyl-N-amido-α-(aminomethyl)methyldimethoxysilane 92.3 g. Product, yield 41.9%.
1H NMR(300MHz,CDCl3),δ5.63(2H),3.65(6H),2.68(2H),2.15(2H),1.52(2H),0.87(3H),0.14(3H) 1 H NMR (300MHz, CDCl 3 ), δ5.63 (2H), 3.65 (6H), 2.68 (2H), 2.15 (2H), 1.52 (2H), 0.87 (3H), 0.14 (3H)
元素分析:C% 43.58,H% 9.16,N% 12.68。Elemental analysis: C% 43.58, H% 9.16, N% 12.68.
实施例8:Example 8
将实施例1~7所得的扩链剂与甲基乙烯基二甲氧基硅烷、甲基乙烯基二丁酮肟基硅烷、甲基乙烯基二己内酰氨基硅烷应用于硅橡胶中,按照发明内容中记载的步骤测定其断裂伸长率和拉伸强度,其结果见表1。The chain extenders obtained in Examples 1 to 7 were applied to silicone rubber with methylvinyldimethoxysilane, methylvinyldibutanonesulfonylsilane and methylvinyldihexanoylaminosilane. The elongation at break and tensile strength of the procedure described in the Summary of the Invention are shown in Table 1.
表1不同扩链剂对断裂伸长率的影响Table 1 Effect of different chain extenders on elongation at break
扩链剂Chain extender | 断裂伸长率Elongation at break | 拉伸强度(Mpa)Tensile strength (Mpa) |
不加do not add | 200%200% | 1.581.58 |
实施例1Example 1 | 430%430% | 1.451.45 |
实施例2Example 2 | 650%650% | 1.381.38 |
实施例3Example 3 | 720%720% | 1.351.35 |
实施例4Example 4 | 820%820% | 1.301.30 |
实施例5Example 5 | 580%580% | 1.401.40 |
实施例6Example 6 | 620%620% | 1.391.39 |
实施例7Example 7 | 480%480% | 1.421.42 |
甲基乙烯基二甲氧基硅烷Methylvinyldimethoxysilane | 230%230% | 1.561.56 |
甲基乙烯基二丁酮肟基硅烷Methyl vinyl dibutyl ketone sulfonyl silane | 260%260% | 1.531.53 |
甲基乙烯基二己内酰氨基硅烷Methylvinyldihexanoylaminosilane | 460%460% | 1.431.43 |
尽管这里参照本发明的解释性实施例对本发明进行了描述,上述实施例仅为本发明较佳的实施方式,本发明的实施方式并不受上述实施例的限制,应该理解,本领域技术人员可以设计出很多其他的修改和实施方式,这些修改和实施方式将落在本申请公开的原则范围和精神之内。
Although the present invention has been described herein with reference to the preferred embodiments of the present invention, the embodiments of the present invention are only preferred embodiments of the present invention, and the embodiments of the present invention are not limited by the above embodiments, and it should be understood that those skilled in the art Many other modifications and embodiments can be devised which fall within the scope and spirit of the principles disclosed herein.
Claims (10)
- 一种有机硅扩链剂,其特征在于所述的有机硅扩链剂具有式I的结构:A silicone chain extender characterized in that the silicone chain extender has the structure of Formula I:R1为含1-6个碳原子的烷基;R 1 is an alkyl group having 1 to 6 carbon atoms;R2选自含1-6个碳原子的烷基、-N=CR6(R7)、-NR8(R9)中的一种;R 2 is selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, -N=CR 6 (R 7 ), and -NR 8 (R 9 );R3选自含1-6个碳原子的烷基、-N=CR6(R7)、-NR8(R9)中的一种;R2、R3相同或不同;R 3 is selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, -N=CR 6 (R 7 ), and -NR 8 (R 9 ); and R 2 and R 3 are the same or different;R4选自氢、烷基、芳基、含甲酸酯基的基团、含酰胺基的基团或杂环烷基中的一种;R 4 is selected from the group consisting of hydrogen, an alkyl group, an aryl group, a formate group-containing group, an amide group-containing group or a heterocycloalkyl group;R5选自氢、烷基、芳基、含甲酸酯基的基团、含酰胺基的基团或杂环烷基中的一种;R4、R5相同或不同;R 5 is selected from hydrogen, an alkyl group, an aryl group, a formate group-containing group, an amide group-containing group or a heterocycloalkyl group; and R 4 and R 5 are the same or different;R6、R7、R8或R9为烷基或环状烷基。R 6 , R 7 , R 8 or R 9 is an alkyl group or a cyclic alkyl group.
- 根据权利要求1所述的有机硅扩链剂,其特征在于所述的R1为含1-6个碳原子的直链烷基、含1-6个碳原子的带支链烷基、含1-6个碳原子的环状烷烃、含1-6个碳原子的芳香烷基或含1-6个碳原子的烷烃芳基中的一种。The silicone chain extender according to claim 1, wherein said R 1 is a linear alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 1 to 6 carbon atoms, and the like One of a cyclic alkane of 1 to 6 carbon atoms, an aromatic alkyl group having 1 to 6 carbon atoms or an alkanearyl group having 1 to 6 carbon atoms.
- 根据权利要求1所述的有机硅扩链剂,其特征在于所述的R4或R5为含酰胺基的基团,该基团具有式III的结构:式III,其中,R11或R12 选自氢、含1~18个碳原子的烷基、芳基、苄基中的一种。The silicone chain extender according to claim 1, wherein said R 4 or R 5 is an amide group-containing group having a structure of formula III: Formula III wherein R 11 or R 12 is selected from the group consisting of hydrogen, an alkyl group having 1 to 18 carbon atoms, an aryl group, and a benzyl group.
- 根据权利要求1所述的有机硅扩链剂,其特征在于所述的R4或R5为杂环烷基,该杂环烷基具有式IV的结构:式IV,其中,R13为含1~12个碳原子的烷基,所述的烷基为直链烷基、带支链烷基、环状烷烃中的一种。The silicone chain extender according to claim 1, wherein said R 4 or R 5 is a heterocycloalkyl group having a structure of formula IV: Formula IV wherein R 13 is an alkyl group having 1 to 12 carbon atoms, and the alkyl group is one of a linear alkyl group, a branched alkyl group, and a cyclic alkane.
- 根据权利要求5所述的有机硅扩链剂,其特征在于所述的R13为含1~12个碳原子的烷基,烷基链段中含有N、O、S或羰基、羟基中的一种或多种。The silicone chain extender according to claim 5, wherein R 13 is an alkyl group having 1 to 12 carbon atoms, and the alkyl segment contains N, O, S or a carbonyl group or a hydroxyl group. One or more.
- 根据权利要求1所述的有机硅扩链剂,其特征在于所述的R4或R5选自吡咯、咪唑、噁唑、哌啶、吗啉、噁嗪中的一种。The silicone chain extender according to claim 1, wherein said R 4 or R 5 is one selected from the group consisting of pyrrole, imidazole, oxazole, piperidine, morpholine, and oxazine.
- 根据权利要求1所述的有机硅扩链剂,其特征在于所述的R4或R5选自氢、甲基、乙基、正丙基、正丁基、异丙基、异丁基、苯基、苄基中的一种。The silicone chain extender according to claim 1, wherein said R 4 or R 5 is selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, One of a phenyl group and a benzyl group.
- 根据权利要求3所述的有机硅扩链剂,其特征在于所述的R10选自甲基、乙基、正丙基、正丁基、异丙基、异丁基、苄基、十二烷基、十八烷基中的一种。The silicone chain extender according to claim 3, wherein said R 10 is selected from the group consisting of methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, benzyl, and twelfth. One of an alkyl group and an octadecyl group.
- 权利要求1-9任一项所述的有机硅扩链剂在硅橡胶中的应用。 Use of the silicone chain extender of any of claims 1-9 in silicone rubber.
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