CN1211583A - 具有二烷氧基有机基硅氧基端基的聚有机硅氧烷 - Google Patents
具有二烷氧基有机基硅氧基端基的聚有机硅氧烷 Download PDFInfo
- Publication number
- CN1211583A CN1211583A CN98109851A CN98109851A CN1211583A CN 1211583 A CN1211583 A CN 1211583A CN 98109851 A CN98109851 A CN 98109851A CN 98109851 A CN98109851 A CN 98109851A CN 1211583 A CN1211583 A CN 1211583A
- Authority
- CN
- China
- Prior art keywords
- organopolysiloxane
- siloxy
- logical formula
- dialkoxy
- silica
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 100
- 239000000377 silicon dioxide Substances 0.000 claims description 50
- 229920001296 polysiloxane Polymers 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- OLLZXQIFCRIRMH-UHFFFAOYSA-N n-methylbutanamide Chemical compound CCCC(=O)NC OLLZXQIFCRIRMH-UHFFFAOYSA-N 0.000 claims description 15
- 101100301546 Arabidopsis thaliana REM19 gene Proteins 0.000 claims description 14
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 claims description 12
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 229910052710 silicon Inorganic materials 0.000 claims description 9
- 239000010703 silicon Substances 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 150000001282 organosilanes Chemical class 0.000 claims description 4
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 claims description 4
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 229920000260 silastic Polymers 0.000 claims description 3
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 3
- 229910004283 SiO 4 Inorganic materials 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- -1 polydimethylsiloxane Polymers 0.000 description 26
- 239000000126 substance Substances 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 20
- 239000004205 dimethyl polysiloxane Substances 0.000 description 16
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 16
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 8
- 230000000903 blocking effect Effects 0.000 description 7
- 238000004132 cross linking Methods 0.000 description 7
- CWAFVXWRGIEBPL-UHFFFAOYSA-N ethoxysilane Chemical compound CCO[SiH3] CWAFVXWRGIEBPL-UHFFFAOYSA-N 0.000 description 7
- 229920002379 silicone rubber Polymers 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 6
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 6
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 229910000077 silane Inorganic materials 0.000 description 5
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 4
- 239000004902 Softening Agent Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000005242 forging Methods 0.000 description 4
- 230000002209 hydrophobic effect Effects 0.000 description 4
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- NHXVNEDMKGDNPR-UHFFFAOYSA-N zinc;pentane-2,4-dione Chemical compound [Zn+2].CC(=O)[CH-]C(C)=O.CC(=O)[CH-]C(C)=O NHXVNEDMKGDNPR-UHFFFAOYSA-N 0.000 description 3
- XUXJHBAJZQREDB-UHFFFAOYSA-N 2-methylbutanamide Chemical compound CCC(C)C(N)=O XUXJHBAJZQREDB-UHFFFAOYSA-N 0.000 description 2
- 238000005133 29Si NMR spectroscopy Methods 0.000 description 2
- QQXVZGWCVOCPDR-UHFFFAOYSA-N 4-ethylisoindole-1,3-dione Chemical compound CCC1=CC=CC2=C1C(=O)NC2=O QQXVZGWCVOCPDR-UHFFFAOYSA-N 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- GHAZCVNUKKZTLG-UHFFFAOYSA-N N-ethylsuccinimide Chemical compound CCN1C(=O)CCC1=O GHAZCVNUKKZTLG-UHFFFAOYSA-N 0.000 description 2
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000013522 chelant Substances 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 230000037305 epidermis formation Effects 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 238000010079 rubber tapping Methods 0.000 description 2
- 239000004945 silicone rubber Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000005987 sulfurization reaction Methods 0.000 description 2
- RSNQKPMXXVDJFG-UHFFFAOYSA-N tetrasiloxane Chemical compound [SiH3]O[SiH2]O[SiH2]O[SiH3] RSNQKPMXXVDJFG-UHFFFAOYSA-N 0.000 description 2
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- KWEKXPWNFQBJAY-UHFFFAOYSA-N (dimethyl-$l^{3}-silanyl)oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)C KWEKXPWNFQBJAY-UHFFFAOYSA-N 0.000 description 1
- WGRZHLPEQDVPET-UHFFFAOYSA-N 2-methoxyethoxysilane Chemical compound COCCO[SiH3] WGRZHLPEQDVPET-UHFFFAOYSA-N 0.000 description 1
- UGAHQGBVQJDSNG-UHFFFAOYSA-N 3-ethyl-1,3-dihydropyrrol-2-one Chemical compound CCC1C=CNC1=O UGAHQGBVQJDSNG-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- JJLKTTCRRLHVGL-UHFFFAOYSA-L [acetyloxy(dibutyl)stannyl] acetate Chemical class CC([O-])=O.CC([O-])=O.CCCC[Sn+2]CCCC JJLKTTCRRLHVGL-UHFFFAOYSA-L 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- BTHCBXJLLCHNMS-UHFFFAOYSA-N acetyloxysilicon Chemical compound CC(=O)O[Si] BTHCBXJLLCHNMS-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- BVCZEBOGSOYJJT-UHFFFAOYSA-N ammonium carbamate Chemical compound [NH4+].NC([O-])=O BVCZEBOGSOYJJT-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 239000011243 crosslinked material Substances 0.000 description 1
- SCKIOUVUHLMUPY-UHFFFAOYSA-N dimethoxy(propan-2-yloxy)silicon Chemical compound CO[Si](OC)OC(C)C SCKIOUVUHLMUPY-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 235000012204 lemonade/lime carbonate Nutrition 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 description 1
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/70—Siloxanes defined by use of the MDTQ nomenclature
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Silicon Polymers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
本发明涉及具有二烷氧基有机基硅氧基的聚有机硅氧烷,该有机基是被取代的酰氨基烷基。
Description
叙述
本发明涉及具有二烷氧基有机基硅氧基的聚有机硅氧烷,该有机基是被取代的酰氨基烷基。该新型聚二有机基硅氧烷可用于RTV1硅氧烷橡胶混合物。
目前有一种已知的单组分硅橡胶混合物(RTV1),如果被脱除水则它能够贮存并在室温下在水存在下硫化得到弹性体。它们一般包括聚合物(通常为线性硅氧烷),具有交联作用的一种化合物(它必须含有容易水解的基团),增塑剂(通常是甲基封端的聚二甲基硅氧烷),和其它所需添加剂,如固化促进剂,颜料,加工助剂和填料。混合物的硫化可以在酸性条件下,例如在乙酰氧基硅烷存在下,在碱性条件下,例如通过使用氨基硅烷,或在中性条件下,例如借助于具有肟基或烷氧基的化合物,来进行。在中性条件下交联的RTV1体系是尤为需要的,如果基质不受混合物固化过程中(例如在混凝土或金属材料的接合中)产生的消去反应产物所影响。
具有OH基团的聚合物常常用于配制RTV1材料。这一操作程序例如是用乙酸酯、肟和胺交联混合物进行的。然而,对于烷氧基交联型材料来说这一方法不是成功的,因为如果使用OH-端基聚合物的话该材料会在混合的早期阶段发生固化。为避免这种情况,含有烷氧基端基的聚合物用于烷氧基交联型RTV1体系。这一制备是已知的并一般通过有一定粘度的羟基-封端聚二有机基硅氧烷与烷氧基硅烷在催化剂存在下进行反应来实现。此时所进行的缩合反应(醇的消去)将形成所需产物。α,ω-二羟基二甲基硅氧烷常常用于这一反应,原因在于它们容易能够以工业用的量获得和在于它们的高反应活性(尤其EP137883,EP304701和EP559045)。所使用的烷氧基硅烷常常是二甲基三甲氧基硅烷。还有一种已知的方法,其中使用诸如氨基丙基三甲氧基硅烷,氨基乙基氨丙基三甲氧基硅烷,缩水甘油氧基丙基三甲氧基硅烷和甲基丙烯酰氧基丙基三甲氧基硅烷的化合物。这些化合物甚至在没有催化剂的情况下(DE4405851)与羟基封端的聚二甲基硅氧烷反应。
在所述方法中,重要的是在OH端基与烷氧基硅烷之间有完全的反应。如果OH基团保留在聚合物中,则当制备RTV1混合物时仍然发生早期交联,而这正是应该由OH封端聚合物与烷氧基硅烷反应所要避免的。然而,在所述方法中,只有甲氧基硅烷的使用得到没有残留OH基团的聚合物。因为甲醇是毒性的,理想的是制备具有非甲氧基端基的基团的聚合物,例如具有乙氧基端基的聚合物。
在迄今已知的羟基封端聚有机硅氧烷与乙氧基硅烷的反应中,在OH基和乙氧基硅烷之间的反应进行得不太完全或非常缓慢。带有二乙氧基氢硅氧基端基的聚合物是例外的。这些可以例如通过羟基封端聚合物与三乙氧基硅烷反应来制备(DE4113554)。这一方法的缺点是,三乙氧基硅烷被处理起来非常困难,并在贮存中分解成自燃的化合物。还有一种可能性是,在聚合物或从其制备的成品RTV1混合物的贮存中挥发出氢。
另一种获得具有乙氧基端基的聚硅氧烷的方法是水解。例如,根据US4772675,1-(2-三乙氧基甲硅基乙基)-1,1,3,3-四甲基二硅氧烷(可从乙烯基三乙氧基硅烷和1,1,3,3-四甲基二硅氧烷得到)能够与乙烯基封端的聚二甲基硅氧烷反应。US4962174描述了H封端聚二甲基硅氧烷与乙烯基三乙氧基硅烷的反应。而且有可能让羟基封端聚二甲基硅氧烷与1,1,3,3-四甲基二硅氧烷在铂化合物存在下反应和同时消除氢,得到H封端的聚合物,然后同样与乙烯基三乙氧基硅烷反应。然而,这些方法总是需要作为起始原料的含二甲基氢基团的化合物,和这些方法很难获得或具有复杂的制备物。
本发明的目的是提供具有二烷氧基有机基硅氧基的聚有机硅氧烷,它能够用作烷氧基交联型RTV1硅橡胶混合物中的聚合物,由于所键接的烷氧基的多样性,除乙氧基交联型体系外的各种交联型体系也应该是可能的。
本发明提供具有二烷氧基有机基硅氧基的聚有机硅氧烷,该有机基是取代的酰氨基烷基。
该新型聚有机硅氧烷含有至少一个具有通式(Ⅰ)的二烷基有机基硅氧基:其中R1各自独立地是未取代的和/或取代的烷基和/或甲硅基,R2各自独立地是未取代的和/或取代的,饱和的和/或不饱和的烷基和/或芳基和/或氢,R3是未取代的或取代的,饱和的或不饱和的烷基,芳基或酰基或者氢,R4是未取代的或取代的,饱和的或不饱和的烷基-或芳基或者氢以及X是氧或硫,其中基团R3和R4可以形成脂族环或杂环,和m是1或2。
通式(Ⅰ)的优选二烷氧基有机基硅氧基是1-(吡咯烷-2-酮-1-基)烷基二烷氧基硅氧基和/或2-(吡咯烷-2-酮-1-基)烷基二烷氧基硅氧基,和1-(N-甲基乙酰氨基)烷基二烷氧基硅氧基和/或2-(N-甲基乙酰氨基)烷基二烷氧基硅氧基。
具有二烷氧基有机基硅氧基的聚有机硅氧烷对应于例如通式(Ⅱ)(SiZR5 2O1/2)a(SiZR5O2/2)b(SiZO3/2)c(SiR5 2O2/2)d(SiR5O3/2)e(SiO4/2)f (Ⅱ)其中R5各自独立地是未取代的和/或取代的,饱和的和/或不饱和的烷基和/或芳基,Z是R5或具有通式(Ⅰ)的二烷氧基有机基硅氧基,前提条件是至少一个二烷氧基有机基硅氧基被键接在每一分子内,a具有1-10中的值,b和c各自独立地具有0-100中的值,d具有20-2000中的值,以及e和f各自独立地具有0-100的值。具有通式(Ⅱ)的聚有机硅氧烷(从它们的制备中得到)仍然含有少量的键接于硅的羟基。
其中R1-R5以及X和m如以上所定义和n取100-1600中的值。
具有通式(Ⅰ)的二烷氧基有机基硅氧基的新型聚有机硅氧烷可通过具有至少一个与硅键接的羟基的聚有机硅氧烷与通式(Ⅳ)的烷氧基硅烷反应来获得:其中R1-R4和X以及m如以上所定义,和/或这些聚合物的部分水解物。
所使用的具有至少一个与硅键接的羟基的聚有机硅氧烷优选是具有通式(Ⅴ)的羟基封端聚二有机基硅氧烷:
HO(SiR5 2O)nH (Ⅴ)其中R5和n如以上所定义。
所使用的具有至少一个与硅键接的羟基的聚有机硅氧烷,尤其具有通式(Ⅴ)的那些,是已知的。它们常常通过在强碱性催化剂和少量水存在下让环状硅氧烷聚合或通过短链线性齐聚物与OH端基进行缩聚反应来制备。由于用于合成的起始化合物,除关键需要的二官能度单元外,还含有三和四官能度单元,聚合物总是还含有在分子中有一个或多个分支的化合物。在起始原料中三或四官能度单元的含量越大和聚合物的分子量越大,则可能性更大的是分子含有分支点。优选的取代基R5是甲基,乙基,苯基,乙烯基和三氟丙基。由于其容易购得,特别优选的是通式(Ⅴ)中n取自100-1600中的值的α,ω-二羟基聚二甲基硅氧烷。虽然纯线性聚合物的使用是优选的,还有可能的是使用含有分支点的聚合物。
具有通式(Ⅴ)的所用烷氧基硅烷是没有作为基团R1键接的甲硅基的化合物,和/或这些化合物的部分水解物。这里优选的是N-1-(三乙氧基甲硅基)乙基-2-吡咯烷酮,N-2-(三乙氧基甲硅基)乙基-2-吡咯烷酮,N-1-(三乙氧基甲硅基)乙基-N-甲基乙酰胺或N-2-(三乙氧基甲硅基)乙基-N-甲基乙酰胺,或这些化合物的混合物。具有通式(Ⅳ)的烷氧基硅烷的可使用的部分水解物的例子是1,3-双(1′-N-甲基乙酰氨基乙基)-1,1,3,3-四乙氧基二硅氧烷。
具有通式(Ⅳ)的所用烷氧基硅烷另外还可以是不含甲硅基的具有通式(Ⅳ)的烷氧基硅烷和/或这些化合物的部分水解物,与具有通式(Ⅵ)的有机基硅烷或与其部分水解物的反应产物:
R5 xSi(OR1)4-x (Ⅵ)
其中R1和R5如以上所定义和x取自0-3中的值,例如1-N-[(甲基二乙氧基硅氧基)二乙氧基甲硅基]乙基-2-吡咯烷酮。
在RTV1体系中也作为交联剂的有机基三乙氧基硅烷和/或四乙氧基硅烷是优选作为具有通式(Ⅵ)的有机硅烷。
具有通式(Ⅳ)的烷氧基硅烷的其它例子是:
N-1-(三乙氧基甲硅基)乙基琥珀酰亚胺R1=CH2CH3,R2=CH3,R3-R4=-CO(CH2)2-,X=O,m=1N-2-(三乙氧基甲硅基)乙基琥珀酰亚胺R1=CH2CH3,R2=H,R3-R4=-CO(CH2)2-,X=O,m=2N-1-(三乙氧基甲硅基)乙基邻苯二甲酰亚胺R1=CH2CH3,R2=CH3,R3-R4=-COC6H4-,X=O,m=1N-2-(三乙氧基甲硅基)乙基邻苯二甲酰亚胺R1=CH2CH3,R2=H,R3-R4=-COC6H4-,X=O,m=2N-1-(三甲氧基甲硅基)乙基-2-吡咯烷酮R1=R2=CH3,R3-R4=-(CH2)3-,X=O,m=1N-2-(三甲氧基甲硅基)乙基-2-吡咯烷酮R1=CH3,R2=H,R3-R4=-(CH2)3-,X=O,m=2N-1-(三正丙氧基甲硅基)乙基-N-甲基乙酰胺R1=CH2CH2CH3,R2=R3=R4=CH3,X=O,m=1N-2-(三正丙氧基甲硅基)乙基-N-甲基乙酰胺R1=CH2CH2CH3,R2=H,R3=R4=CH3,X=O,m=2N-1-(三(2-甲氧基乙氧基)甲硅基)乙基-N-甲基硫代乙酰胺R1=CH2CH2OCH3,R2=R3=R4=CH3,X=S,m=1N-2-(三(2-甲氧基乙氧基)甲硅基)乙基-N-甲基硫代乙酰胺R1=CH2CH2OCH3,R2=H,R3=R4=CH3,X=S,m=2
这些化合物也可以以混合物形式使用。
它们例如可以通过相应三烷氧基硅烷与相应N-乙烯基-取代的酰胺的加成反应而获得。
通式(Ⅳ)的烷氧基硅烷的用量取决于聚有机硅氧烷中键接于硅的羟基的含量并由本技术领域中熟练人员容易地与具体的环境匹配来选择。通式(Ⅳ)的烷氧基硅烷一般以0.1-10wt%,优选1-5wt%的量使用(基于用作反应参与者的聚有机硅氧烷)。在反应结束后保留下来的多余烷氧基硅烷能够保留在产物或被分离出并用于另一反应中。
在烷氧基硅烷和含有键接于硅的羟基的聚有机硅氧烷之间的反应在没有添加催化剂的情况下也能够进行,甚至在室温下。该温度可被提高以加速反应。优选的温度是在20-130℃,在80-11O℃范围内的温度是特别优选的。为了进一步加速反应,还有可能添加能够催化羟基封端聚有机硅氧烷和烷氧基硅烷之间反应的已知化合物。此类化合物的例子是NaOH或KOH,锂化合物,如LiOH,硅烷醇锂,碱金属醇盐(已与CO2或羧酸混合以减少它们的反应活性),路易斯酸(例如铝螯合物),酸和胺的混合物或氨基甲酸铵。
具有二烷氧基有机基硅氧基的新型聚有机硅氧烷可以作为聚合物用于RTV1硅橡胶混合物中。
RTV1混合物的其它常规组分是交联剂,例如具有通式(Ⅶ)的烷氧基硅烷和这些化合物的部分水解物:
R6 rSi(OR1)4-r (Ⅶ)其中R1如以上所定义和R6是取代的或未取代的烷基,链烯基或芳基或以下结构的基团:其中R2,R3,R4,X和m如以上所定义。优选的烷氧基硅烷是甲基三乙氧基硅烷,乙烯基三乙氧基硅烷,四乙氧基硅烷,苯基三乙氧基硅烷,四(2-甲氧基乙氧基)硅烷,四(2-丁氧基乙氧基)硅烷,N-1-(三乙氧基甲硅基)乙基-2-吡咯烷酮,N-1-(三乙氧基甲硅基)乙基-N-甲基乙酰胺,N-2-(三乙氧基甲硅基)乙基-2-吡咯烷酮和N-2-(三乙氧基甲硅基)乙基-N-甲基乙酰胺。作为交联剂还有可能使用以上所述烷氧基硅烷的任何所需混合物。用以上所述化合物的一种或混合物的低聚水解物/缩合物也能够获得同样的效果。
在RTV1体系中特别优选的增塑剂是具有粘度为0.1-1Pas的三甲基甲硅基封端的聚二甲基硅氧烷。还有可能使用其中一些甲基已被其它有机基团如苯基、乙烯基或三氟丙基替换的甲基封端聚二甲基硅氧烷。还有可能使用支化化合物,它是当用于合成增塑剂的硅烷含有三-或四-官能度硅烷时所生产的化合物。另外还有可能的是使用其它有机化合物,例如,某些烃混合物,作为增塑剂。
为了获得足够高的交联速度,将交联催化剂加入到体系中。常规的化合物是二烷基锡化合物,例如二月桂酸一或二乙酸二丁基锡,和/或钛化合物,如钛酸四丁基酯或钛螯合物。还有可能使用催化剂混合物。
为了获得某些机械性能,也有可能向RTV1体系中加入高比表面积的填料,如煅制硅石或沉淀碳酸钙。也有可能使用低表面积的填料作为增量剂。对于此目的来说研磨好的碳酸钙是优选的。
还可以混合除以上所述化合物外的已知添加剂,如颜料、偶联剂和杀菌剂,这取决于RTV1体系的应用。
具有二烷氧基有机基硅氧基的新型聚有机硅氧烷可以用来制备快速固化和无粘性的RTV1硅橡胶混合物。产物的机械性能对应于由现有甲氧基交联型体系所获得的值。具体的优点是现在有可能产生一种体系,该体系的交联只产生完全不含毒性甲醇的消去产物。
实施例
实施例1
2000g具有粘度50,000mPas的α,ω-二羟基聚二甲基硅氧烷与其中已溶解了1g乙酰丙酮锌的100g N-1-(三乙氧基甲硅基)乙基-2-吡咯烷酮混合。在80℃下2小时的反应时间过后,中止反应。蒸除过量的乙氧基硅烷。留下粘度为57,000mPas和OH含量<30mg/kg的聚合物。
实施例2
2000g具有粘度50,000mPas的α,ω-二羟基聚二甲基硅氧烷与100g N-1-(三乙氧基甲硅基)乙基-N-吡咯烷酮混合。在130℃下2小时的反应时间过后,中止反应。蒸除过量的乙氧基硅烷。留下粘度为53,500mPas和OH含量<30mg/kg的聚合物。
实施例3
2000g具有粘度50,000mPas的α,ω-二羟基聚二甲基硅氧烷与其中已溶解了1g乙酰丙酮锌的100g N-1-(三乙氧基甲硅基)乙基-2-甲基乙酰胺混合。在80℃下2小时的反应时间过后,中止反应。蒸除过量的乙氧基硅烷。留下粘度为57,000mPas和OH含量<30mg/kg的聚合物。
实施例4
2g的1,7-二羟基-1,1,3,3,5,5,7,7-八甲基四硅氧烷与其中已溶解了20mg乙酸锌的3.5g N-1-(三乙氧基甲硅基)乙基-N-甲基乙酰胺混合。该反应可借助于29SiNMR谱跟踪来进行。在室温下24小时的反应时间过后,OH基团已定量反应。所形成的端基绝无例外地是所需1-(N-甲基乙酰氨基)乙基二乙氧基硅氧基。没有观察到通过OH基团与乙醇反应所形成的乙氧基二甲基硅氧基。同样没有检测到通过从所用N-1-(三乙氧基甲硅基)乙基-N-甲基乙酰胺中消去N-甲基乙酰胺所产生的三乙氧基硅氧基端基。
实施例5
重复实施例4的实验,使用N-1-(三乙氧基甲硅基)乙基-2-吡咯烷酮。在这一反应,所形成的端基同样是无例外地为所需二乙氧基有机基硅氧基。
实施例6
2g的1,7-二羟基-1,1,3,3,5,5,7,7-八甲基四硅氧烷与3.5g N-1-(三正丙氧基甲硅基)乙基-2-甲基乙酰胺混合。在室温下24小时的反应时间过后,OH基团已定量反应。从29Si NMR谱数据得到,所形成的端基绝无例外地是所需1-(N-甲基乙酰氨基)乙基二正丙氧基硅氧基。没有观察到通过OH基团与正丙醇反应所形成的正丙氧基二甲基硅氧基。同样没有检测到通过从所用N-1-(三正丙氧基甲硅基)乙基-N-甲基乙酰胺中消去N-甲基乙酰胺所产生的三正丙氧基硅氧基端基。
实施例7
11.8g的甲基三乙氧基硅烷和14.9g N-1-(三乙氧基甲硅基)乙基-N-甲基乙酰胺的混合物与1.1g水在10ml乙醇中的溶液混合。在24小时后,所形成的乙醇与作为溶剂所添加的乙醇一起被蒸除。保留了20.5g的低聚水解物,它由34wt%的甲基三乙氧基硅烷,8wt%的N-1-(三乙氧基甲硅基)乙基-N-甲基乙酰胺,27wt%的N-1-[(二乙氧基甲基硅氧基)二乙氧基甲硅基]乙基-N-甲基乙酰胺,8wt%的1,3-双(1′-(N-甲基乙酰氨基)乙基-1,1,3,3-四乙氧基二硅氧烷和23wt%的N-1-(三乙氧基甲硅基)乙基-N-甲基乙酰胺的高级低聚水解物/缩合产物组成。由29Si NMR谱测定其组成。
20g的这一低聚混合物与100g的粘度为20,000mPas的α,ω-二羟基二甲基硅氧烷混合。在110℃下2小时的反应时间后,中止反应。保留了粘度为27,000mPas和OH含量<30mg/kg的的聚合物。
实施例8
473g与在实施例1中一样制备的聚合物,350g粘度为100mPas的甲基封端的聚二甲基硅氧烷,103g已用六甲基二硅氮烷作疏水处理的且具有比表面积约200m2/g的煅制硅石,41g甲基三乙氧基硅烷和12g的双(乙酰基乙酸乙酯)二异丁氧基钛[bis(ethylacetoacetato)diisobutoxy titanate]用溶解器进行处理,得到坚固稠性浆,经暴露于大气湿气后交联得到硅橡胶。该产物的性能列于表1中。
实施例9
473g与在实施例1中一样制备但没有除去多余乙氧基硅烷的聚合物,350g粘度为100mPas的甲基封端的聚二甲基硅氧烷,164g已用六甲基二硅氮烷作疏水处理的且具有比表面积约200m3/g的煅制硅石,25g甲基三乙氧基硅烷和37g的双(乙酰基乙酸乙酯)二异丁氧基钛[bis(ethylacetoacetato)diisobutoxy titanate]用溶解器进行处理,得到坚固稠性浆,经暴露于大气湿气后交联得到硅橡胶。该产物的性能列于表1中。
实施例10
473g与在实施例3中一样制备但没有除去多余乙氧基硅烷的聚合物,350g粘度为100mPas的甲基封端的聚二甲基硅氧烷,103g已用六甲基二硅氮烷作疏水处理的且具有比表面积约200m2/g的煅制硅石,25g甲基三乙氧基硅烷和37g的双(乙酰基乙酸乙酯)二异丁氧基钛[bis(ethylacetoacetato)diisobutoxy titanate]用溶解器进行处理,得到坚固稠性浆,经暴露于大气湿气后交联得到硅橡胶。该产物的性能列于表1中。
对比实施例11
为了能够将在以上实施例中制备的物质的性能进行对比,制备包括目前已知的原料的混合物,但它是甲氧基交联型的,即在其固化过程中产生较大量的甲醇。
1150g甲氧基封端的聚合物(通过让粘度为50,000mPas的α,ω-二羟基聚二甲基硅氧烷和甲基三甲氧基硅烷在乙酰丙酮锌存在下于80℃下反应所制备),850g粘度为100mPas的甲基封端聚二甲基硅氧烷,400g的已用六甲基二硅氮烷作疏水处理的且具有比表面积约200m2/g的煅制硅石,80g甲基三甲氧基硅烷和30g的双(乙酰基乙酸乙酯)二异丁氧基钛[bis(ethylacetoacetato)diisobutoxy titanate]用溶解器进行处理,得到坚固稠性浆,经暴露于大气湿气后交联得到硅橡胶。该产物的性能列于表1中。
表1
性能 | 方法 | Ex.8 | Ex.9 | Ex.10 | 对比Ex.11 |
表皮形成时间(分钟) | 20 | 30 | 30 | 20 | |
拉伸强度[MPa] | DIN 53504 S2 | 1.28 | 1.26 | 0.87 | 1.45 |
断裂伸长率[%] | DIN 53504 S2 | 883 | 650 | 473 | 630 |
在100%伸长率下的拉伸强度[MPa] | DIN 53504 S2 | 0.25 | 0.41 | 0.29 | 0.32 |
肖氏A硬度 | DIN 53505 | 13 | 23 | 13 | 17 |
在制备产物后立即测量表皮形成时间。在23℃下和50%相对湿度下固化7天后测量机械性能(拉伸强度,断裂伸长率,在100%伸长率下的拉伸强度,和硬度)。
Claims (15)
2.根据权利要求1所要求的具有二烷氧基有机基硅氧基的聚有机硅氧烷,其中二烷氧基有机基硅氧基是1-(吡咯烷-2-酮-1-基)烷基二烷氧基硅氧基或2-(吡咯烷-2-酮-1-基)烷基二烷氧基硅氧基。
3.根据权利要求1所要求的具有二烷氧基有机基硅氧基的聚有机硅氧烷,其中二烷氧基有机基硅氧基是1-(N-甲基乙酰氨基)烷基二烷氧基硅氧基或2-(N-甲基乙酰氨基)烷基二烷氧基硅氧基。
4.根据权利要求1所要求的具有二烷氧基有机基硅氧基的聚有机硅氧烷,其中聚有机硅氧烷对应于通式(Ⅱ)(SiZR5 2O1/2)a(SiZR5O2/2)b(SiZO3/2)c(SiR5 2O2/2)d(SiR5O3/2)e(SiO4/2)f (Ⅱ)其中R5各自独立地是未取代的和/或取代的,饱和的和/或不饱和的烷基和/或芳基,Z是R5或具有通式(Ⅰ)的二烷氧基有机基硅氧基,前提条件是至少一个二烷氧基有机基硅氧基被键接在每一分子内,a具有1-10中的值,b和c各自独立地具有0-100中的值,d具有20-2000中的值,以及e和f各自独立地具有0-100的值。
5.根据权利要求1所要求的具有二烷氧基有机基硅氧基的聚有机硅氧烷,其特征在于它对应于通式(Ⅲ)
其中R1-R5以及X和m如以上所定义和n取100-1600中的值。
7.根据权利要求6所要求的聚有机硅氧烷,其中具有至少一个与硅键接的羟基的聚有机硅氧烷对应于通式(Ⅴ)
HO(SiR5 2O)nH (Ⅴ)
其中R5和n如以上所定义。
8.根据权利要求6所要求的聚有机硅氧烷,其中作为具有通式(Ⅱ)的烷氧基硅烷是没有作为基团R1键接的甲硅基的化合物,和/或这些化合物的部分水解物。
9.根据权利要求8所要求的聚有机硅氧烷,其中作为具有通式(Ⅳ)的烷氧基硅烷是N-1-(三乙氧基甲硅基)乙基-吡咯烷-2-酮或N-2-(三乙氧基甲硅基)乙基-吡咯烷-2-酮或它们的混合物。
10.根据权利要求8所要求的聚有机硅氧烷,其中具有通式(Ⅳ)的所用烷氧基硅烷是N-1-(三乙氧基甲硅基)乙基-N-甲基乙酰胺或N-2-(三乙氧基甲硅基)乙基-N-甲基乙酰胺,或这些化合物的混合物。
11.根据权利要求6所要求的聚有机硅氧烷,其中具有通式(Ⅳ)的所用烷氧基硅烷是不含甲硅基的具有通式(Ⅳ)的烷氧基硅烷和/或这些化合物的部分水解物,与具有通式(Ⅵ)的有机硅烷或与其部分水解物的反应产物:
R5 xSi(OR1)4-x (Ⅵ)
其中R1和R5如以上所定义和x取自0-3中的值。
12.根据权利要求11所要求的聚有机硅氧烷,其中有机基三乙氧基硅烷和/或四乙氧基硅烷用作通式(Ⅵ)的有机硅烷。
13.根据权利要求11所要求的聚有机硅氧烷,其中具有通式(Ⅳ)的所用烷氧基硅烷是N-1-[(甲基二乙氧基硅氧基)二乙氧基甲硅基]乙基-吡咯烷-2-酮。
14.根据权利要求6所要求的聚有机硅氧烷,使用0.1-10wt%的具有通式(Ⅳ)的烷氧基硅烷,基于具有至少一个键接于硅的羟基的聚有机硅氧烷计。
15.具有通式(Ⅰ)的二烷氧基有机基硅氧基的聚有机硅氧烷在RTV1硅橡胶混合物中的用途。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19725518A DE19725518A1 (de) | 1997-06-17 | 1997-06-17 | Polyorganosiloxane mit Dialkoxyorganosiloxy-Gruppen |
DE19725518.3 | 1997-06-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN1211583A true CN1211583A (zh) | 1999-03-24 |
Family
ID=7832692
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN98109851A Pending CN1211583A (zh) | 1997-06-17 | 1998-06-15 | 具有二烷氧基有机基硅氧基端基的聚有机硅氧烷 |
Country Status (7)
Country | Link |
---|---|
US (1) | US6018011A (zh) |
EP (1) | EP0885915A3 (zh) |
JP (1) | JPH1112360A (zh) |
KR (1) | KR19990007008A (zh) |
CN (1) | CN1211583A (zh) |
CA (1) | CA2240310A1 (zh) |
DE (1) | DE19725518A1 (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1095466C (zh) * | 1999-09-10 | 2002-12-04 | 王继峰 | 大豆总黄酮及其制备方法和药物新用途 |
CN101899159A (zh) * | 2010-07-23 | 2010-12-01 | 深圳市安品有机硅材料有限公司 | 单组分led封装材料用硅树脂及其制备方法 |
Families Citing this family (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7858818B2 (en) * | 2001-01-31 | 2010-12-28 | Momentive Performance Materials Inc. | Nanosized copper catalyst precursors for the direct synthesis of trialkoxysilanes |
US7339068B2 (en) | 2001-01-31 | 2008-03-04 | Momentive Performance Materials Inc. | Nanosized copper catalyst precursors for the direct synthesis of trialkoxysilanes |
CN100381448C (zh) * | 2001-04-30 | 2008-04-16 | 通用电气公司 | 用于填充弹性体组合物的含杂化硅偶联剂 |
AU2003287087A1 (en) * | 2002-10-23 | 2004-05-13 | Henkel Corporation | Fast moisture curing and uv-moisture dual curing compositions |
DE10259613A1 (de) | 2002-12-19 | 2004-07-08 | Wacker-Chemie Gmbh | Organopolysiloxanzusammensetzungen und deren Einsatz in bei Raumtemperatur vernetzbaren niedermoduligen Massen |
US20050234208A1 (en) * | 2004-04-14 | 2005-10-20 | Matthias Koch | Fast curing polydiorganosiloxanes |
DE102004037043A1 (de) * | 2004-07-29 | 2006-03-23 | Degussa Ag | Blockkondensate organofunktioneller Siloxane, deren Herstellung, Verwendung sowie deren Eigenschaften |
DE102004037044A1 (de) * | 2004-07-29 | 2006-03-23 | Degussa Ag | Mittel zur Ausstattung von auf Cellulose und/oder Stärke basierenden Substraten mit Wasser abweisenden und gleichzeitig pilz-, bakterien-, insekten- sowie algenwidrigen Eigenschaften |
DE102004037045A1 (de) * | 2004-07-29 | 2006-04-27 | Degussa Ag | Wässrige Silan-Nanokomposite |
DE102004049427A1 (de) | 2004-10-08 | 2006-04-13 | Degussa Ag | Polyetherfunktionelle Siloxane, polyethersiloxanhaltige Zusammensetzungen, Verfahren zu deren Herstellung und deren Verwendung |
US7452937B2 (en) * | 2005-11-28 | 2008-11-18 | Henkel Corporation | Highly elongated single component, non-corrosive RTV silicone compositions |
JP4868135B2 (ja) * | 2006-04-18 | 2012-02-01 | 信越化学工業株式会社 | 光反応性基含有シロキサン化合物、その製造方法及び光硬化性樹脂組成物、その硬化皮膜を有する物品 |
TWI472595B (zh) * | 2006-08-22 | 2015-02-11 | Mitsubishi Chem Corp | Semiconductor component components and semiconductor light emitting components |
AU2008244254B2 (en) * | 2007-05-01 | 2013-06-27 | Akzo Nobel Coatings International B.V. | Anti-fouling coating compositions containing a carboxyl-functional organosilicone |
CN103890045A (zh) | 2011-10-19 | 2014-06-25 | 3M创新有限公司 | 硬涂层组合物 |
CN103819680B (zh) * | 2014-02-25 | 2016-05-25 | 宁波润禾化学工业有限公司 | 一种甲氧基封端氨基改性硅油的制备方法 |
KR101789311B1 (ko) | 2017-05-31 | 2017-10-23 | 정의우 | 경계석용 라텍스개질 콘크리트 조성물 |
KR102016991B1 (ko) * | 2017-10-16 | 2019-09-02 | 정의우 | 콘크리트 조성물 |
WO2023069840A1 (en) * | 2021-10-21 | 2023-04-27 | Dow Global Technologies Llc | Composition and method for synthesis of an alkoxy-functional organosiloxane oligomer |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4460739A (en) * | 1983-07-01 | 1984-07-17 | General Electric Company | Composition for promoting adhesion of curable silicones to substrates |
US4772675A (en) * | 1986-03-03 | 1988-09-20 | Dow Corning Corporation | Methods of improving shelf life of silicone elastomeric sealant |
US4657967A (en) * | 1986-04-07 | 1987-04-14 | Dow Corning Corporation | Room temperature curing compositions containing tetrafunctional ethoxy-ketoximo silane crosslinkers |
CA1293836C (en) * | 1986-06-30 | 1991-12-31 | Robert S. Neale | Polyorganosiloxane cross-linkers for rtv sealants |
JPH0699868B2 (ja) * | 1990-08-01 | 1994-12-07 | 信越化学工業株式会社 | 繊維処理剤 |
US5409963A (en) * | 1993-12-28 | 1995-04-25 | Three Bond Co., Ltd. | Curable silicone composition |
DE19515947A1 (de) * | 1995-05-02 | 1996-11-07 | Huels Silicone Gmbh | Lagerstabile, alkoxyvernetzende RTV1-Systeme |
-
1997
- 1997-06-17 DE DE19725518A patent/DE19725518A1/de not_active Withdrawn
-
1998
- 1998-06-10 EP EP98110603A patent/EP0885915A3/en not_active Withdrawn
- 1998-06-11 CA CA002240310A patent/CA2240310A1/en not_active Abandoned
- 1998-06-15 JP JP10167035A patent/JPH1112360A/ja active Pending
- 1998-06-15 CN CN98109851A patent/CN1211583A/zh active Pending
- 1998-06-16 KR KR1019980022464A patent/KR19990007008A/ko not_active Application Discontinuation
- 1998-06-17 US US09/098,644 patent/US6018011A/en not_active Expired - Fee Related
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1095466C (zh) * | 1999-09-10 | 2002-12-04 | 王继峰 | 大豆总黄酮及其制备方法和药物新用途 |
CN101899159A (zh) * | 2010-07-23 | 2010-12-01 | 深圳市安品有机硅材料有限公司 | 单组分led封装材料用硅树脂及其制备方法 |
Also Published As
Publication number | Publication date |
---|---|
JPH1112360A (ja) | 1999-01-19 |
CA2240310A1 (en) | 1998-12-17 |
EP0885915A3 (en) | 1999-02-03 |
DE19725518A1 (de) | 1998-12-24 |
EP0885915A2 (de) | 1998-12-23 |
KR19990007008A (ko) | 1999-01-25 |
US6018011A (en) | 2000-01-25 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN1183201C (zh) | 烷氧基交联型rtv1硅橡胶混合物 | |
CN1211583A (zh) | 具有二烷氧基有机基硅氧基端基的聚有机硅氧烷 | |
CA1266940A (en) | Acrylic polymers containing hydrolyzable moieties from organosilane compounds | |
US5079324A (en) | Lioh catalyzed preparation of alkoxylated diorganopolysiloxanes | |
EP3119847B1 (en) | Alkoxy group-containing silicones with reactive functional groups of defined reactivity | |
CN1246365C (zh) | 通过烷氧基交联的rtv-1硅橡胶混合物 | |
CN1202506A (zh) | 烷氧基交联型rtv1硅橡胶混合物 | |
WO1991016371A1 (de) | Organo(poly)siloxane mit organyloxy- und hydrogengruppen aufweisenden, endständigen siloxaneinheiten | |
CN1522271A (zh) | 液态烷氧基甲硅烷基官能的硅氧烷树脂,其制备方法,及可固化硅氧烷树脂组合物 | |
CN101027342A (zh) | 含氮的有机聚硅氧烷及其在可交联组合物中的用途 | |
AU616947B2 (en) | organopolysiloxane compositions which crosslink at a room temperature to form paint-compatible to overcoatable elastomers | |
RU2189995C2 (ru) | Органополисилоксановые материалы, которые могут быть поперечно сшиты расщепляющими спиртами в эластомеры | |
KR100344475B1 (ko) | 오가노실록산화합물 | |
CN112094434B (zh) | 一种含硅烷氧基硼硅氧烷改性白炭黑的制备方法及其应用 | |
US6803409B2 (en) | Organopolysiloxane copolymer and method of preparing | |
JP2716679B2 (ja) | エラストマーに架橋可能なオルガノポリシロキサン材料、有機珪素化合物、およびその製造方法 | |
JPH1067935A (ja) | 硬化性オルガノポリシロキサン組成物 | |
NO311089B1 (no) | Organopolysiloksanforbindelser som under alkoholavspaltning tverrbinder og danner elastomerer, fremgangsmåte for fremstillingog anvendelse av disse | |
JP3067953B2 (ja) | 末端ヒドロキシ基停止オルガノハイドロジェンポリシロキサンの製造方法 | |
KR20050019089A (ko) | 오가노폴리실록산 공중합체 및 이의 제조방법 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C53 | Correction of patent of invention or patent application | ||
COR | Change of bibliographic data |
Free format text: CORRECT: APPLICANT; FROM: HUELS SILICONE GMBH TO: WACKER CHEMIE CO., LTD. |
|
CP03 | Change of name, title or address |
Address after: Munich, Germany Applicant after: Wacker Chemical GmbH Address before: German new Entelizi Applicant before: Huels Silicone GmbH |
|
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
WD01 | Invention patent application deemed withdrawn after publication |