CN1046527C - 具有亲水基团的硅烷及基制备方法和应用 - Google Patents
具有亲水基团的硅烷及基制备方法和应用 Download PDFInfo
- Publication number
- CN1046527C CN1046527C CN94107819A CN94107819A CN1046527C CN 1046527 C CN1046527 C CN 1046527C CN 94107819 A CN94107819 A CN 94107819A CN 94107819 A CN94107819 A CN 94107819A CN 1046527 C CN1046527 C CN 1046527C
- Authority
- CN
- China
- Prior art keywords
- group
- value
- silane
- general formula
- carbon atom
- 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.)
- Expired - Fee Related
Links
- 229910000077 silane Inorganic materials 0.000 title claims description 25
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 title claims description 24
- 238000002360 preparation method Methods 0.000 title claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 24
- 239000007864 aqueous solution Substances 0.000 claims abstract description 10
- 229920000570 polyether Polymers 0.000 claims abstract description 7
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 10
- 239000013543 active substance Substances 0.000 claims description 9
- 238000006459 hydrosilylation reaction Methods 0.000 claims description 8
- 239000012736 aqueous medium Substances 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229910052697 platinum Inorganic materials 0.000 claims description 6
- 239000002841 Lewis acid Substances 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 150000007517 lewis acids Chemical class 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 230000000655 anti-hydrolysis Effects 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 150000004756 silanes Chemical class 0.000 abstract description 3
- 230000007062 hydrolysis Effects 0.000 abstract description 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 239000000047 product Substances 0.000 description 17
- -1 siloxanes Chemical class 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 10
- 239000004094 surface-active agent Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 239000004743 Polypropylene Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000002209 hydrophobic effect Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229920001155 polypropylene Polymers 0.000 description 5
- FTIUOYWRXKQYNI-UHFFFAOYSA-N 6-trimethylsilylhexan-1-ol Chemical compound C[Si](C)(C)CCCCCCO FTIUOYWRXKQYNI-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- IKXDEFIEGAVNOZ-UHFFFAOYSA-N [SiH4].[C] Chemical compound [SiH4].[C] IKXDEFIEGAVNOZ-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000003301 hydrolyzing effect Effects 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 4
- 229940094989 trimethylsilane Drugs 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000007259 addition reaction Methods 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000005702 oxyalkylene group Chemical group 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 125000001118 alkylidene group Chemical group 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- KTOQFRSUBIJCIG-UHFFFAOYSA-N 11-trimethylsilylundecan-1-ol Chemical compound C[Si](C)(C)CCCCCCCCCCCO KTOQFRSUBIJCIG-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 description 1
- LSWYGACWGAICNM-UHFFFAOYSA-N 2-(prop-2-enoxymethyl)oxirane Chemical compound C=CCOCC1CO1 LSWYGACWGAICNM-UHFFFAOYSA-N 0.000 description 1
- 238000005133 29Si NMR spectroscopy Methods 0.000 description 1
- YNUUCDHAZGAVEZ-UHFFFAOYSA-N 3-trimethylsilylpropan-1-ol Chemical compound C[Si](C)(C)CCCO YNUUCDHAZGAVEZ-UHFFFAOYSA-N 0.000 description 1
- 125000006042 4-hexenyl group Chemical group 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 239000004831 Hot glue Substances 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229910002808 Si–O–Si Inorganic materials 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000006065 biodegradation reaction Methods 0.000 description 1
- VQLYBLABXAHUDN-UHFFFAOYSA-N bis(4-fluorophenyl)-methyl-(1,2,4-triazol-1-ylmethyl)silane;methyl n-(1h-benzimidazol-2-yl)carbamate Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1.C=1C=C(F)C=CC=1[Si](C=1C=CC(F)=CC=1)(C)CN1C=NC=N1 VQLYBLABXAHUDN-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001768 cations Chemical group 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000009713 electroplating Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000003311 flocculating effect Effects 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical group C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000000413 hydrolysate Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical group 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 238000002444 silanisation Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 229960004249 sodium acetate Drugs 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 229940125725 tranquilizer Drugs 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/54—Silicon compounds
-
- 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
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
-
- 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
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0825—Preparations of compounds not comprising Si-Si or Si-cyano linkages
- C07F7/0827—Syntheses with formation of a Si-C bond
- C07F7/0829—Hydrosilylation reactions
-
- 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
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0825—Preparations of compounds not comprising Si-Si or Si-cyano linkages
- C07F7/083—Syntheses without formation of a Si-C bond
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
- C11D1/146—Sulfuric acid esters
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/29—Sulfates of polyoxyalkylene ethers
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/82—Compounds containing silicon
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/162—Organic compounds containing Si
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/03—Organic sulfoxy compound containing
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Materials Engineering (AREA)
- Silicon Polymers (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Biological Depolymerization Polymers (AREA)
- Detergent Compositions (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Polyethers (AREA)
Abstract
下列通式所示的硅烷
式中，R1、R2、和R3为甲基，R4为具有4-14个碳原子的两价烃基，R5为通式-O(CH2)b-所示的一个基团或通式-(OCnH2n)c-所示的一个聚醚基团，其中b的值为1-6，n的平均值为2，c的值为1-10，a为0或1，并且满足该硅烷表面活性剂可以将1%(重量)水溶液的表面张力值降到≤25mN/m的条件。该硅烷可生物降解、抗水解并具有显著的表面活性特性。
Description
本发明涉及一类新的具有亲水基团的硅烷及其制备方法和作为水基介质表面活性剂的应用。本发明尤其涉及可大大降低水基介质表面张力、具抗水解稳定性的硅烷表面活性剂。本发明中的“水基”介质还应包括那些主要由水组成的并可另外含有可溶于水的或可与水混溶的有机溶剂的介质。
由现有技术已知，取代基上具有阴离子基团、阳离子基团或两性基团的有机改性硅氧烷，例如聚醚硅氧烷或聚硅氧烷，在结构选择适当并且亲水基团与疏水基团比例得当的情况下，可以显著地降低水溶液的表面张力。
在DE-PS4141046中，对至少具有3个硅原子的表面活性剂作了描述。这类表面活性剂的通式如下：式中，
R1为甲基或苯基，但其中至少有90％的R1基团是甲基；
R2与R1相同或为-(CH2)6-OSO3-·M+,M+为碱金属离子、1/2碱土金属离子或被烷基取代的铵离子；
R3与R1或R2相同，条件是：平均每个分子中至少有一个R2基团或R3基团为-(CH2)6-OSO3 -·M+基团；
a为0-5，并且
b为0-5。
所选出的含有3个硅原子的三硅氧烷己基硫酸盐，在中性水基介质中具有良好的降低表面张力的作用，可以使表面张力值降到21mN/m左右。但它们在酸性和碱性溶液中，由于Si-O-Si键的水解，并且水解产物又被重新缩合成高分子齐聚物，因此很快丧失其功效，加之还有一部分会变成水基介质中的不溶解物，故其性能不稳定。
此外，在EP-OS0367381(A2)和英国专利1520421中对低硅原子含量的表面活性剂做了进一步的描述。
EP-OS0367381(A2)涉及一类有机硅化合物，其通式如下：
式中，R分别独立地为至多具有18个碳原子的烷基、芳基、囟代烷基或囟代芳基；每个R’代表亚烷基，它们用至多6个碳原子把相邻的硅原子隔开；R”分别独立地代表R，或者当a=0时，为R3SiR’-基团；Z是一个含有硫、氮或磷的亲水取代基、羧基官能团或其盐，a的值为0、1或2。
由此得出，硅有机基团按定义至少含有两个硅原子。制备这类碳硅烷(Carbosilane)所花代价较高，例如采用类似于格利尼雅反应的方法来制备。根据此方法，通过烯丙基缩水甘油醚或烯丙基胺的氢化硅烷化和已公知的第二步反应就可合成具有季磺酸盐结构或季甜菜碱结构的碳硅烷表面活性剂。采用此方法制得的物质可将1％的蒸馏水溶液的表面张力降低到23-25mN/m。
英国专利1520421中记述了碳硅烷表面活性剂及其制备方法。其通式如下：式中，
R为甲基、乙基、丙基或三氟丙基，但其中至少有50％的R为甲基；
R’为具有1-6个碳原子的烷基；
R”为具有2-6个碳原子的两价脂族烃基，它以一个至少由两个碳原子构成的桥键把Q和邻近的硅原子连接起来；
Q为-O(C2H4O)cX基团，其中c的值为3-12,X为氢；R为
或
式中R为一个具有1-5个碳原子的烷基；以及a为1或2,b为2或3。
根据定义，此时也必须至少有两个硅原子。应用试验结果表明，这类化合物具有明显的起泡特性。
同时，本领域专业人员也已知道，这些具有类似结构的已知的碳硅烷的一组化合物中，随着硅原子数的减少，特别是当硅原子数量由4减至3或2时，这些化合物的表面活性性质将变差。此研究结果在诺伊曼的理论中有所反映(A.W.诺伊曼，D.伦佐夫，物理化学杂志，新版68,11(1969))，该理论阐明了水溶液表面张力被降低到30-40mN/m以下是由于硅氧烷构架的全甲基化的表面所致。
此外还请参见H.Maki等人1970年在日本出版物UKAGAKU19，第4期，51页起和YUKAGAKU19，第11期，23页起发表的文章，在这两篇文章中记述了下式定义的化合物：(CH3)3Si(CH2)3(C2H4O)nH和((CH2)4)3Si(CH2)3(C2H4O)mH式中，n=4.0或7.7,m=10或17。但这两种化合物在1％(重量)溶液中只能将界面张力降低到≥26.5mN/m。
在这两篇日本公开文献中，同时还介绍了下式所示的季氮化合物Bu3M(CH2)3N+(CH3)3Cl-(Bu=丁基，M=Sn,Si)该化合物虽然有抗菌活性，但其表面活性剂特性却不太强。最佳的具有代表性的这种季氮化合物也只能将1％水溶液的表面张力值降到32mN/m。
本发明基于下述出乎预料的发现：与譬如诺伊曼理论所反映出的普通专业知识相反，所选择的硅烷只带有一个硅原子，并且其分子的亲水部分和疏水部分比例得当，这样的化合物可以非常有效地降低水的表面张力，并且与硅氧烷表面活性剂相反，甚至在酸性和碱性介质中经数日、数周后仍能保持其抗水解稳定性。本发明硅烷的另一个而且是未预料到的优点，是它具有可完全生物降解的特性，该特性使本发明的硅烷特别适合用作表面活性剂。从现有技术中是绝不会推导出这种特性，并且与迄今通常就硅有机化合物为了拥有降低含水体系中界面张力的性能而必须满足的结构方面要求的看法完全相反。
所以，本发明的一个主题为下列通式所示的硅烷：
式中，R1、R2和R3为甲基，R4为具有4-14个碳原子的两价烃基，R5为通式-O(CH2)b-所示的基团或通式-(OCnH2n)c-所示的聚醚基团，其中b的值为1-6，n的平均值为2，c的值为1-10，a为0或1，并且满足该硅烷表面活性剂可以将1％(重量)水溶液的表面张力值降到≤25mN/m(25℃时用Du-Nouy张力计测得)的条件。
R4是具有4-14个碳原子的两价烃基，例如-C4H8-,-C5H10-,-C6H12-或-C11H22-基团。R4可以被例如支链烷基或囟原子取代。但特别选用直链烃基。
R4基的其它例子是下式所示的基团：
R4优选是具有4-9个碳原子的，特别是具有4-6个碳原子的两价脂族烃基。
R5是通式-O(CH2)b-所示的基团或通式-(OCnH2n)c-所示的聚醚基团，其中b的值为1-6,n的平均值为2,c的值为1-10。这种基团的例子为-OCH2-、-O(CH2)4-、-O(CH2)6-、-(OC2H4)8-和-(OCH(CH3)CH2)5-。
n的值优选为2.0，使得此时亚氧烷基单元均为亚氧乙基单元。下标c用于“说明该单元的数量”，c的值为1-10，优选为3-6。
a的值为0或1。
本发明硅烷的例子为(CH3)3Si(CH2)3-OCH2CH2-OH；(CH3)3Si(CH2)6-O-[CH2CH2O-]4H；(CH3)3Si(CH2)6-O-[CH2CH2O-]2H；(CH3)3Si(CH2)6-O-[CH2CH2O-]6H，
本发明的另一主题是本发明化合物的制备方法。制备此种化合物的方法如下：在已知的氢化硅烷化(hydrosilylation)催化剂的存在下，对下列通式所示的硅烷
与a)下列通式所示的化合物发生加成反应
CH2=CH-R6-(R5)a-OH式中R6为一个具有2-12个碳原子的两价脂族烃基，或与b)下列通式所示的化合物发生加成反应
CH2=CH-R6-OH，并且在采用工艺方案b)时，在碱性催化剂存在下或路易斯酸存在下，将cmol的下列通式所示的环氧烷加到端部的羟基上
式中，R7是氢或具有1或2个碳原子的烷基，而且环氧烷平均具有2-2.5个碳原子。
R6优选是具有1-7个碳原子，特别是1-4个碳原子的两价烃基。
环氧烷优选是采用环氧乙烷和环氧丙烷。所以，上述两种环氧烷的等摩尔混合物产生n值为2.5的产物。也可以与少量的环氧丁烷一起使用，但须满足n不得大于2.5的条件。
已知的催化剂适用于环氧烷与硅烷端部OH基的加成反应。可以采用NaOH或KOH或其醇化物，特别是甲醇钠或甲醇钾作为碱性催化剂。最好选用BF3-醚化物作为路易斯酸。如果要加成多种不同的环氧烷，则可以采用相应的环氧烷混合物并获得亚氧烷基单元统计分布的产物。也可以把多种不同的环氧烷按先后顺序陆续加成，从而可以分批排布亚氧烷基单元。环氧烷的加成，最好在高压密封容器内进行。
为了使本发明化合物的界面活性特性最佳化，其亲水和疏水的分子部分的比例必须得当。R1、R2、R3和R4基可以影响其疏水特性。这些基团中碳原子越多，本发明的硅烷就越疏水。其亲水特性是由(R5)a，特别由下标n和c的数值决定。在给定的范围内，n值越小，c值越大，则硅烷表面活性剂就越亲水。在实施例中还将对这一表面活性特性的影响做进一步阐述，以便本领域的熟练技术人员易于理解。因此，为了获得所需要的特性，特别是为了获得所需的降低水基介质表面张力的特性，仅需进行少许相应的初步试验，但这些试验绝不包括发明性步骤。
优选在最高约130℃的温度和有催化剂存在下进行氢化硅烷化。适用的催化剂尤其以铂催化剂为佳。这类氢化硅烷化反应，对本领域的熟练技术人员来说是非常熟知的。
本发明的另一个主题，是本发明硅烷在水基介质中作表面活性剂的应用。就此而言，可以通过添加1％(重量)的本发明的化合物将水溶液表面张力值降到约22mN/m。同时，本发明化合物的生物降解特性具有非常重大的意义。此外该硅烷类表面活性剂还具有抗水解稳定性。
本发明硅烷表面活性剂的重要用途如下：用作润湿剂：
在处理植物用的制品(农艺配方)中；用于改善低表面自由能的基质如聚乙烯表面或聚丙烯表面的润湿性；用于制漆工业；制造感光胶片；用于电镀技术；用作分散剂：
用于分散染料、颜料和填料；在纺织工业中用作制备纺织助剂、软化剂、润滑剂、防静电制品时的乳化剂或添加剂；作为染色助剂；作为一般表面活性剂：
用于灭火剂；作为泡沫安定剂；用于快速印刷油墨、粘合剂、分散粘合剂、热熔性粘合剂的表面活性添加剂；用于洗涤剂；用作工业洗涤剂的添加剂；作为原料用于诸如护肤品、洗发液和浴液等化妆品；在工业生产和家庭日常生活中的应用：作为防雾助剂；用于餐具洗洁剂、洗涤剂、厕所清洁剂、自增光乳剂。
在下述实施例中，将对本发明化合物的制备方法及其特性作进一步的阐述。实施例是用来说明本发明而不是限制本发明。
实施例1
a)[6-羟己基]三甲基硅烷(中间体，非本发明)的制备
在300毫升实验室高压釜中称入28.7克1-己烯-5-醇(0.287mol)和3毫克铂催化剂。此后，将高压釜连同内容物，在氩保护气体蒸发条件下，置于丙酮/干冰浴中，使之冷却，并将22.4克冷凝态三甲基硅烷(0.299mol，沸点6.7℃)虹吸至高压釜中。将高压釜关闭，并加热至130℃。此时，内压上升到13.7巴，然后又降到约5.7巴，这标志着反应已开始。
然后冷却到室温，使高压釜释压，释压后滤除铂催化剂，分离出内容物(称量：50.7克，质量损耗：0.9克)。
羟基数量：理论值321.7，实际值306
经29Si-NMR谱和1H-NMR谱分析，得下列产物结构：
(CH3)3Si(CH2)6OH
该产物在20℃油泵真空中，从低挥发组分中分离出来。
b)经[羟己基]三甲基硅烷的乙氧基化制备[聚氧亚乙基]三甲基硅烷(本发明)
在一个装设有强力冷却器、温度计、冷却套滴液漏斗及氮气连接管的三颈烧瓶中，装入20.0克(0.11mol)[羟己基]三甲基硅烷和0.82克50％的三氟化硼的醚溶液。然后，缓慢滴入21.1克(0.48mol)冷凝环氧乙烷。为使内部温度不超过20-30℃，用冰浴来冷却放热反应。而后，在室温下再搅拌两小时，在用1.50克碳酸氢钠和0.41克水(1％(重量))中和后，在90℃喷水空气泵真空中将挥发性组分从产物中分离掉。
接着在预加助滤剂的条件下进行过滤，得淡黄色透明产物，该产物经1H-NMR谱及凝胶渗透色谱分析，表明其具有4.2个氧亚乙基单元，据此，可用下列平均式表示：(CH3)3Si-(CH2)6-O-[CH2CH2O14.2-H
将该产物以1％(重量)或0.1％(重量)的比例与蒸馏水混合成溶液，经24小时放置后，在聚丙烯薄膜上试验其铺展性(50微升滴液)。
表1
| 浓度[重量百分比] | 在聚丙烯薄膜上的铺展[毫米] |
| 10.1 | 6575 |
根据上述方法，采用[羟己基]三甲基硅烷、[羟丙基]三甲基硅烷及[羟十一基]三甲基硅烷作原料，通过改变氧亚烷基单元的数量和种类，就可以制备出本发明的化合物，该化合物的特性如下表：
表2
[羟己基]三甲基硅烷的烷氧基化产物
| 环氧乙烷/环氧丙烷 | 铺展[毫米][0.1％(重量)] | 表面张力[mN/m](0.1％(重量)溶液) |
| 1.5/02.8/04.0/04.7/08.3/00/5.04.0/1.0(无规的)4.0/1.0(1．环氧乙烷；2．环氧丙烷 | 8080757520不溶解5520(混浊溶液) | 23.122.423.022.725.2n.b.23.824.9 |
表中“无规的”表示环氧乙烷和环氧丙烷以混合物形式加成，使环氧烷统计分布。
“1、环氧乙烷；2、环氧丙烷”表示首先加成一定量的环氧乙烷，然后再加成一定量的环氧丙烷。
“n.b.”表示“不能测定”。
表3
[羟丙基]三甲基硅烷的烷氧基化产物
| 环氧乙烷/环氧丙烷 | 铺展[毫米][1％(重量)] | 表面张力[mN/m](1％(重量)溶液) |
| 2.4/04.3/08.3/010.5/00/5.05/1(1．环氧乙烷；2．环氧丙烷)5/2(1．环氧乙烷；2．环氧丙烷)5/1(无规的 | 60752015不溶解603060 | 23.123.124.125.3n.b.23.924.923.2 |
表4
[羟十一基]三甲基硅烷的烷氧基化产物
| 环氧乙烷/环氧丙烷 | 铺展[毫米][1％(重量)] | 表面张力[mN/m](1％(重量)溶液) |
| 5/0 | 40 | 23.9 |
实施例2
用氢化硅烷化法制备通式(CH3)3Si(CH2)6[OCH2CH2]4OH所示的[聚氧亚烷基]三甲基硅烷
在300毫升的实验室高压釜中称入88.14克通式CH2=CH(CH2)4[OCH2CH2]4OH所示的己烯基聚醚(0.3mol，羟基数203.4，碘数量86.4)和5毫克铂催化剂。尔后，将高压釜连同内容物，在氩保护气体蒸发条件下，置于丙酮/干冰浴中，使之冷却，并将23.34克三甲基硅烷(0.315mol)虹吸至高压釜中。将高压釜关闭，并加热到130℃。此时，内压升到8巴，然后又大约降到3.5巴。
冷却到室温，使高压釜释压，然后滤除掉铂催化剂，分离出内容物(称量：109.0克，质量损耗：0.6克)。
表5
表面张力降低与水溶液浓度的关系
| 浓度(％(重量)) | 表面张力[mN/m],25℃ |
| 1.00.40.30.150.090.07 | 23.023.023.123.830.734.7 |
表6
铺展能力与水溶液浓度的关系
| 浓度[重量百分比] | 铺展[毫米] |
| 0.010.10.30.51.0 | 885736148 |
上表表明，在浓度为0.1％(重量)时有一个取决于浓度的最大铺展值。
实施例3
本发明其它化合物的制备及这些化合物的性质
下述化合物的制备方法与上述两个实施例中所述的方法相同：
TMS-PE1=TMS-C3-O-CH2CH2OH
TMS=三甲基甲硅烷基
TMS-PE2=TMS-C6-O-[CH2CH2O]2H
TMS-PE3=TMS-C6-O-[CH2CH2O]4H
TMS-PE4=TMS-C6-O-[CH2CH2O]6H
首先准备好浓度为1％(重量)产物的水溶液，并采用Du-Nouy方法测定其表面张力。为了测定润湿力，在聚丙烯薄膜上测量1％表面活性剂溶液50微升液滴的最大铺展表面。在此种条件下纯净水的空白试验值为8毫米。同时通过对1％溶液润湿特性的观察，跟踪调查长时间抗水解稳定性。
表7
| 产物 | 溶液 | 表面张力[mN/m] | 聚丙烯薄膜上的铺展(毫米) |
| TMS-PE1TMS-PE2TMS-PE3TMS-PE4 | 混浊混浊混浊混浊 | 23.723.223.024.7 | 28704835 |
实施例4
本发明化合物的可生物降解性
按经济合作发展组织基准(OECD 301D)对实施例1b)的产物的可生物降解性进行检验。
在采用的检验方法条件下，28天后其可生物降解性为：生物需氧量(BOD)是化学需氧量(COD)的88％。在相同的时间内被检物醋酸钠有60％以上被分解，这一事实毫无疑问地证实了此结果的有效性。
Claims (9)
1、通式
所示的硅烷，式中，R1、R2和R3为甲基，R4为具有4-14个碳原子的两价烃基，R5为通式-O(CH2)b-所示的基团或通式-(OCnH2n)c-所示的聚醚基团，其中b的值为1-6，n的平均值为2，c的值为1-10，a为0或1，并且所述的硅烷具有这样的性质：其1％(重量)水溶液的表面张力值降到≤25mN/m(25℃时用Du-Nouy张力计测得)。
2、依照权利要求1所述的硅烷，其特征是：R4基团是具有4-14个碳原子的两价脂族烃基。
3、依照权利要求2所述的硅烷，其特征是：R4基团是具有4-9个碳原子的两价脂族烃基。
4、依照权利要求3所述的硅烷，其特征是：R4基团是具有4-6个碳原子的两价脂族烃基。
5、依照上述任一个权利要求所述的硅烷，其特征是：R5基团是聚醚基团，其中n值为2,c值为3-6。
6、权利要求1-7所述硅烷的制备方法，其特征是：在已知的氢化硅烷化催化剂存在下，对下列通式所示的硅烷
加成a)下列通式所示的化合物
CH2=CH-R6-(R5)a-OH式中，R6为具有2-12个碳原子的两价脂族烃基，或加成b)下列通式所示的化合物
CH2=CH-R6-OH并且在采用制备方法b)时，在碱性催化剂存在下或路易斯酸存在下，将cmol的下列通式所示环氧烷加到端部烃基上式中，R7是氢或具有1或2个碳原子的烷基并且环氧烷平均具有2-2.5个碳原子。
7、依照权利要求6所述的方法，其特征是：氢化硅烷化在加温下和/或在溶剂存在下进行。
8、依照权利要求6或7所述的方法，其特征是：氢化硅烷化在铂催化剂存在下进行。
9、依照权利要求1所述硅烷作水基介质中可生物降解的、抗水解的表面活性剂的应用。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4320920A DE4320920C1 (de) | 1993-06-24 | 1993-06-24 | Silane mit hydrophilen Gruppen, deren Herstellung und Verwendung als Tenside in wäßrigen Medien |
| DEP4320920.3 | 1993-06-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1106413A CN1106413A (zh) | 1995-08-09 |
| CN1046527C true CN1046527C (zh) | 1999-11-17 |
Family
ID=6491067
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN94107819A Expired - Fee Related CN1046527C (zh) | 1993-06-24 | 1994-06-24 | 具有亲水基团的硅烷及基制备方法和应用 |
| CN94107821A Expired - Fee Related CN1044708C (zh) | 1993-06-24 | 1994-06-24 | 具有亲水基团的硅烷及其制备方法和应用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN94107821A Expired - Fee Related CN1044708C (zh) | 1993-06-24 | 1994-06-24 | 具有亲水基团的硅烷及其制备方法和应用 |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US5430166A (zh) |
| EP (2) | EP0630901B1 (zh) |
| JP (2) | JP2749520B2 (zh) |
| CN (2) | CN1046527C (zh) |
| AU (2) | AU667436B2 (zh) |
| BR (2) | BR9402517A (zh) |
| CA (2) | CA2124876C (zh) |
| DE (3) | DE4320920C1 (zh) |
| DK (2) | DK0630901T3 (zh) |
| ES (2) | ES2128460T3 (zh) |
| MX (2) | MX9404815A (zh) |
| NZ (2) | NZ260770A (zh) |
Families Citing this family (81)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4330059C1 (de) * | 1993-09-06 | 1994-10-20 | Goldschmidt Ag Th | Silane mit hydrophilen Gruppen, deren Herstellung und Verwendung als Tenside in wäßrigen Medien |
| US5496830A (en) * | 1994-09-14 | 1996-03-05 | Johns Hopkins University | Inhibition of hemoflagellates by camptothecin compounds |
| DE4433139A1 (de) * | 1994-09-16 | 1996-03-21 | Thera Ges Fuer Patente | Hydrophilierte Zahnabdruckmassen |
| DE4439598A1 (de) * | 1994-11-05 | 1996-05-09 | Goldschmidt Ag Th | Tensidgemische aus Silantensiden und Polyalkylenoxiden und deren Verwendung |
| GB2331457B (en) * | 1997-11-12 | 2001-07-04 | Graviner Ltd Kidde | Fire or explosion suppressants and methods |
| CN1065762C (zh) * | 1998-05-15 | 2001-05-16 | 常子元 | 调胰降糖胶囊 |
| WO2000038721A1 (en) | 1998-12-23 | 2000-07-06 | G.D. Searle Llc | Combinations of cholesteryl ester transfer protein inhibitors and nicotinic acid derivatives for cardiovascular indications |
| KR100377405B1 (ko) * | 2000-08-31 | 2003-03-26 | 주식회사피죤 | 김 서림 방지용 코팅 조성물 및 이로부터 얻어지는 코팅제품 |
| JP4906203B2 (ja) * | 2001-09-20 | 2012-03-28 | 東レ・ダウコーニング株式会社 | 高純度ポリオキシアルキレン変性ポリシロキサン及びその製造法 |
| US6900257B2 (en) * | 2002-08-06 | 2005-05-31 | General Electric Company | Antistatic agents and polymer compositions derived therefrom |
| US6841598B2 (en) * | 2002-08-16 | 2005-01-11 | General Electric Company | Antistatic and antidust agents, compositions thereof, and methods of manufacture |
| US7405002B2 (en) * | 2004-08-04 | 2008-07-29 | Agency For Science, Technology And Research | Coated water-soluble nanoparticles comprising semiconductor core and silica coating |
| US7534489B2 (en) * | 2004-09-24 | 2009-05-19 | Agency For Science, Technology And Research | Coated composites of magnetic material and quantum dots |
| US7645720B2 (en) * | 2005-12-13 | 2010-01-12 | Momentive Performance Materials Inc. | Extreme environment surfactant compositions comprising hydrolysis resistant organomodified disiloxane surfactants |
| US7507775B2 (en) * | 2005-10-13 | 2009-03-24 | Momentive Performance Materials Inc. | Hydrolysis resistant organomodified disiloxane surfactants |
| US20070131611A1 (en) * | 2005-12-13 | 2007-06-14 | General Electric Company | Membrane-based article and associated method |
| US20070134283A1 (en) * | 2005-12-13 | 2007-06-14 | General Electric Company | Surfactant-based composition and associated methods |
| US20070131610A1 (en) * | 2005-12-13 | 2007-06-14 | General Electric Company | Membrane-based apparatus and associated method |
| US7601680B2 (en) * | 2005-12-13 | 2009-10-13 | Momentive Performance Materials | Gemini silicone surfactant compositions and associated methods |
| US7935842B2 (en) * | 2006-02-09 | 2011-05-03 | Momentive Performance Materials Inc. | Hydrolysis resistant organomodified trisiloxane surfactants |
| US20070197394A1 (en) * | 2006-02-17 | 2007-08-23 | General Electric Company | Hydrolysis resistant organomodified trisiloxane surfactants |
| US20070249560A1 (en) * | 2006-04-21 | 2007-10-25 | Leatherman Mark D | Hydrolysis resistant organomodified silyated surfactants |
| US7700797B2 (en) * | 2006-05-22 | 2010-04-20 | Momentive Performance Materials Inc. | Use of hydrolysis resistant organomodified silylated surfactants |
| US7259220B1 (en) * | 2006-07-13 | 2007-08-21 | General Electric Company | Selective hydrosilylation method |
| US7678859B2 (en) * | 2006-09-14 | 2010-03-16 | 3M Innovative Properties Company | Preparation and stabilization of fluoropolymer dispersions |
| US7399350B2 (en) * | 2006-10-17 | 2008-07-15 | Momentive Performance Materials Inc. | Fluorine-free disiloxane surfactant compositions for use in coatings and printing ink compositions |
| US7964032B2 (en) * | 2006-10-17 | 2011-06-21 | Momentive Performance Materials Inc. | Fluorine-free trisiloxane surfactant compositions for use in coatings and printing ink compositions |
| US20080167269A1 (en) * | 2006-12-11 | 2008-07-10 | Momentive Performance Materials Inc. | Hydrolysis resistant organomodified silylated ionic surfactants |
| CN101631456B (zh) * | 2006-12-11 | 2014-04-30 | 莫门蒂夫性能材料股份有限公司 | 抗水解的有机改性硅烷化离子表面活性剂 |
| CN101003008B (zh) * | 2006-12-29 | 2010-12-08 | 南京四新科技应用研究所有限公司 | 一种提高乳液稳定性的方法 |
| CN101186702B (zh) * | 2007-11-16 | 2011-04-20 | 北京化工大学 | 多乙烯多醇有机硅水溶性聚合物及其制备方法 |
| DE102007055484A1 (de) * | 2007-11-21 | 2009-05-28 | Evonik Goldschmidt Gmbh | Verfahren zur Herstellung von Polydimethylsiloxanen an sulfonsauren Kationenaustauscherharzen |
| DE102007055485A1 (de) * | 2007-11-21 | 2009-06-04 | Evonik Goldschmidt Gmbh | Verfahren zur Herstellung verzweigter SiH-funktioneller Polysiloxane und deren Verwendung zur Herstellung SiC- und SiOC-verknüpfter, verzweigter organomodifizierter Polysiloxane |
| CN101205299B (zh) * | 2007-11-30 | 2011-04-20 | 北京化工大学 | 多乙烯多醇有机硅阳离子聚合物及其制备方法 |
| DE102008002713A1 (de) * | 2008-06-27 | 2009-12-31 | Evonik Goldschmidt Gmbh | Neue Polyethersiloxane enthaltende Alkoxylierungsprodukte durch direkte Alkoxylierung organomodifizierter alpha, omega-Dihydroxysiloxane an Doppelmetallcyanid (DMC)-Katalysatoren, sowie Verfahren zu deren Herstellung |
| DE102008041601A1 (de) | 2008-08-27 | 2010-03-04 | Evonik Goldschmidt Gmbh | Verfahren zur Herstellung verzweigter SiH-funtioneller Polysiloxane und deren Verwendung zur Herstellung flüssiger, SiC- oder SiOC-verknüpfter, verzweigter organomodifizierter Polysiloxane |
| DE102008043218A1 (de) * | 2008-09-24 | 2010-04-01 | Evonik Goldschmidt Gmbh | Polymere Werkstoffe sowie daraus bestehende Kleber- und Beschichtungsmittel auf Basis multialkoxysilylfunktioneller Präpolymerer |
| DE102008043245A1 (de) * | 2008-10-29 | 2010-05-06 | Evonik Goldschmidt Gmbh | Siliconpolyether-Copolymersysteme sowie Verfahren zu deren Herstellung durch Alkoxylierungsreaktion |
| DE102009022628A1 (de) * | 2008-12-05 | 2010-06-10 | Evonik Goldschmidt Gmbh | Verfahren zur Modifizierung von Oberflächen |
| EP2389417B1 (en) * | 2009-01-20 | 2017-03-15 | Cabot Corporation | Compositons comprising silane modified metal oxides |
| BRPI1008036B1 (pt) | 2009-02-25 | 2018-11-13 | Momentive Performance Mat Inc | "composições de revestimentos aguosa, substrato revestido, composição de tinta de impressão e substrato impresso" |
| DE102009003274A1 (de) * | 2009-05-20 | 2010-11-25 | Evonik Goldschmidt Gmbh | Zusammensetzungen enthaltend Polyether-Polysiloxan-Copolymere |
| DE102009022631A1 (de) | 2009-05-25 | 2010-12-16 | Evonik Goldschmidt Gmbh | Härtbare Silylgruppen enthaltende Zusammensetzungen und deren Verwendung |
| DE102009022630A1 (de) | 2009-05-25 | 2010-12-02 | Evonik Goldschmidt Gmbh | Emulsionen auf Basis Silylgruppen tragender Hydroxylverbindungen |
| DE102009034607A1 (de) * | 2009-07-24 | 2011-01-27 | Evonik Goldschmidt Gmbh | Neuartige Siliconpolyethercopolymere und Verfahren zu deren Herstellung |
| DE102009028636A1 (de) * | 2009-08-19 | 2011-02-24 | Evonik Goldschmidt Gmbh | Neuartige Urethangruppen enthaltende silylierte Präpolymere und Verfahren zu deren Herstellung |
| DE102010001350A1 (de) | 2010-01-29 | 2011-08-04 | Evonik Goldschmidt GmbH, 45127 | Neuartige lineare Polydimethylsiloxan-Polyether-Copolymere mit Amino- und/oder quaternären Ammoniumgruppen und deren Verwendung |
| DE102010001531A1 (de) | 2010-02-03 | 2011-08-04 | Evonik Goldschmidt GmbH, 45127 | Neuartige organomodifizierte Siloxane mit primären Aminofunktionen, neuartige organomodifizierte Siloxane mit quaternären Ammoniumfunktionen und das Verfahren zu deren Herstellung |
| DE102010002180A1 (de) * | 2010-02-22 | 2011-08-25 | Evonik Goldschmidt GmbH, 45127 | Stickstoffhaltige silizium-organische Pfropfmischpolymere |
| DE102010002178A1 (de) * | 2010-02-22 | 2011-08-25 | Evonik Goldschmidt GmbH, 45127 | Verfahren zur Herstellung von Amin-Amid-funktionellen Siloxanen |
| US8318037B2 (en) * | 2010-04-30 | 2012-11-27 | Wisconsin Alumni Research Foundation | Organosilicon glycol-based electrolytes with a hydroxy terminus |
| DE102010062156A1 (de) | 2010-10-25 | 2012-04-26 | Evonik Goldschmidt Gmbh | Polysiloxane mit stickstoffhaltigen Gruppen |
| TWI479956B (zh) * | 2010-12-09 | 2015-04-01 | Hon Hai Prec Ind Co Ltd | 具有高速差分訊號佈線結構的印刷電路板 |
| DE102011076019A1 (de) | 2011-05-18 | 2012-11-22 | Evonik Goldschmidt Gmbh | Alkoxylierungsprodukte und Verfahren zu ihrer Herstellung mittels DMC-Katalysatoren |
| DE102011088787A1 (de) | 2011-12-16 | 2013-06-20 | Evonik Industries Ag | Siloxannitrone und deren Anwendung |
| DE102012202521A1 (de) | 2012-02-20 | 2013-08-22 | Evonik Goldschmidt Gmbh | Verzweigte Polysiloxane und deren Verwendung |
| DE102013102239A1 (de) | 2013-03-06 | 2014-09-11 | Universität Zu Köln | Carbosilanhaltiger Feuerlöschschaum |
| TWI601738B (zh) * | 2013-05-08 | 2017-10-11 | 道康寧公司 | 親水性有機矽烷 |
| DE102013214081A1 (de) | 2013-07-18 | 2015-01-22 | Evonik Industries Ag | Neue aminosäuremodifizierte Siloxane, Verfahren zu ihrer Herstellung und Anwendung |
| DE102014209408A1 (de) | 2014-05-19 | 2015-11-19 | Evonik Degussa Gmbh | Ethoxylatherstellung unter Verwendung hoch aktiver Doppelmetallcyanid-Katalysatoren |
| US10913921B2 (en) * | 2014-06-18 | 2021-02-09 | HEX Performance, LLC | Performance gear, textile technology, and cleaning and protecting systems and methods |
| EP3020749B1 (de) | 2014-11-12 | 2020-09-30 | Evonik Operations GmbH | Verfahren zur herstellung von platin enthaltenden zusammensetzungen |
| US10899937B2 (en) | 2014-12-22 | 2021-01-26 | U.S.A. As Represented By The Administrator Of The National Aeronautics And Space Administration | Hydrogen-bonding surfaces for ice mitigation |
| EP3168273B1 (de) | 2015-11-11 | 2018-05-23 | Evonik Degussa GmbH | Härtbare polymere |
| CN109068634B (zh) | 2016-03-31 | 2021-11-02 | 莫门蒂夫性能材料股份有限公司 | 包含有机硅润湿剂的基于卵磷脂的喷雾佐剂 |
| JP6651968B2 (ja) * | 2016-04-21 | 2020-02-19 | 日清紡ホールディングス株式会社 | ケイ素含有硫酸エステル塩 |
| EP3321304B1 (de) | 2016-11-15 | 2019-06-19 | Evonik Degussa GmbH | Mischungen zyklischer-verzweigter siloxane vom d/t-typ und deren folgeprodukte |
| CN108164693B (zh) * | 2016-12-07 | 2019-11-29 | 上海东大化学有限公司 | 一种硅改性聚醚及其制备方法、应用 |
| CN106750327B (zh) * | 2016-12-29 | 2019-10-11 | 中国石油天然气股份有限公司 | 一种改性聚醚及其制备方法和应用 |
| EP3415548B1 (de) | 2017-06-13 | 2020-03-25 | Evonik Operations GmbH | Verfahren zur herstellung sic-verknüpfter polyethersiloxane |
| EP3415547B1 (de) | 2017-06-13 | 2020-03-25 | Evonik Operations GmbH | Verfahren zur herstellung sic-verknüpfter polyethersiloxane |
| EP3438158B1 (de) | 2017-08-01 | 2020-11-25 | Evonik Operations GmbH | Herstellung von sioc-verknüpften polyethersiloxanen |
| US10233200B2 (en) | 2017-08-21 | 2019-03-19 | Momentive Performance Matericals Inc. | Organomodified monosilyl compound, its preparation and applications thereof |
| US10918109B2 (en) | 2017-09-25 | 2021-02-16 | Momentive Performance Materials Inc. | Lecithin-based spray adjuvant containing organosilicon wetting agents |
| EP3467006B1 (de) | 2017-10-09 | 2022-11-30 | Evonik Operations GmbH | Mischungen zyklischer-verzweigter siloxane vom d/t-typ und deren folgeprodukte |
| US10428229B2 (en) | 2017-12-28 | 2019-10-01 | Industrial Technology Research Institute | Aqueous coating material and method for manufacturing the same |
| EP3611214A1 (de) | 2018-08-15 | 2020-02-19 | Evonik Operations GmbH | Sioc-verknüpfte, lineare polydimethylsiloxan-polyoxyalkylen-blockcopolymere |
| EP3611215A1 (de) | 2018-08-15 | 2020-02-19 | Evonik Operations GmbH | Verfahren zur herstellung acetoxygruppen-tragender siloxane |
| EP3663346B1 (de) | 2018-12-04 | 2023-11-15 | Evonik Operations GmbH | Reaktivsiloxane |
| CN110003477B (zh) * | 2019-05-20 | 2021-09-14 | 胡海明 | 一种聚二甲基硅烷安全生产设备 |
| ES2977903T3 (es) | 2020-03-27 | 2024-09-02 | Evonik Operations Gmbh | Reciclaje de materiales de estructuras planas siliconizadas |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2039512A (en) * | 1978-12-05 | 1980-08-13 | Oreal | Surface-active polysiloxanes |
| US4847397A (en) * | 1987-05-26 | 1989-07-11 | Dow Corning Kabushiki Kaisha | Method for the production of silyl group containing amine compounds |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2872434A (en) * | 1959-02-03 | mezsio | ||
| US2582568A (en) * | 1947-08-26 | 1952-01-15 | Dow Corning | Silicon-containing esters |
| US2640064A (en) * | 1950-06-08 | 1953-05-26 | Dow Corning | Bromoalkylsilanes and their preparation |
| US2629727A (en) * | 1950-07-26 | 1953-02-24 | Dow Corning | Organosilyl alcohols |
| US2983745A (en) * | 1956-07-18 | 1961-05-09 | Dow Corning | Silpropoxanes |
| US2924588A (en) * | 1957-04-22 | 1960-02-09 | Dow Corning | Organosiloxane alcohols |
| US3109012A (en) * | 1959-06-12 | 1963-10-29 | Goldschmidt Ag Th | Method of producing organo-silicon compounds and products therefrom |
| US3161611A (en) * | 1960-07-06 | 1964-12-15 | Goldschmidt Ag Th | Aqueous solutions of hydroxypropyl silanols and their preparation |
| US3159496A (en) * | 1960-08-29 | 1964-12-01 | Goldschmidt Ag Th | Process for the preparation of aqueous solutions of organosilicon compounds |
| US3141898A (en) * | 1961-01-03 | 1964-07-21 | Minnesota Mining & Mfg | 2, 2-dimethyl-2-silaalkane-sulfonic acids and their salts |
| BE754332A (fr) * | 1969-08-05 | 1971-02-03 | Dow Corning | Copolymeres de siloxanes a fonctionnalite carboxyle utiles comme agent d'encollage et papier encolle a l'aide de ces copolymeres |
| GB1520421A (en) * | 1975-10-09 | 1978-08-09 | Dow Corning Ltd | Organosilicon compounds |
| US4152165A (en) * | 1978-04-11 | 1979-05-01 | Minnesota Mining And Manufacturing Company | One-part hydrophilic treatment compositions |
| US4235638A (en) * | 1978-04-11 | 1980-11-25 | Minnesota Mining And Manufacturing Company | Sulfonato-organosilanol compounds and aqueous solutions |
| JPS6170551A (ja) * | 1984-09-14 | 1986-04-11 | Hitachi Ltd | レジスト現像液 |
| GB8708552D0 (en) * | 1987-04-09 | 1987-05-13 | Dow Corning Ltd | Surface active silicone compound |
| GB8819567D0 (en) * | 1988-08-17 | 1988-09-21 | Dow Corning Ltd | Carbosilane surfactants |
| JPH0678345B2 (ja) * | 1989-04-25 | 1994-10-05 | 信越化学工業株式会社 | 含フッ素界面活性剤及びその製造方法 |
| US5113005A (en) * | 1991-06-07 | 1992-05-12 | Abbott Laboratories | Process for synthesis of silyl alcohols |
| US5159095A (en) * | 1991-06-07 | 1992-10-27 | Abbott Laboratories | Substituted silyl alcohols |
| JPH0625615A (ja) * | 1992-04-07 | 1994-02-01 | Shin Etsu Chem Co Ltd | プライマー組成物 |
| CA2129773C (en) * | 1993-09-02 | 2007-05-01 | Michael Klaus | Aromatic carboxylic acid derivatives |
-
1993
- 1993-06-24 DE DE4320920A patent/DE4320920C1/de not_active Expired - Fee Related
-
1994
- 1994-06-01 CA CA002124876A patent/CA2124876C/en not_active Expired - Fee Related
- 1994-06-01 CA CA002124877A patent/CA2124877C/en not_active Expired - Fee Related
- 1994-06-15 DK DK94109141T patent/DK0630901T3/da active
- 1994-06-15 DE DE59407622T patent/DE59407622D1/de not_active Expired - Fee Related
- 1994-06-15 NZ NZ260770A patent/NZ260770A/en unknown
- 1994-06-15 AU AU64753/94A patent/AU667436B2/en not_active Ceased
- 1994-06-15 DE DE59407623T patent/DE59407623D1/de not_active Expired - Fee Related
- 1994-06-15 AU AU64752/94A patent/AU668041B2/en not_active Ceased
- 1994-06-15 DK DK94109144T patent/DK0630902T3/da active
- 1994-06-15 EP EP94109141A patent/EP0630901B1/de not_active Expired - Lifetime
- 1994-06-15 ES ES94109141T patent/ES2128460T3/es not_active Expired - Lifetime
- 1994-06-15 EP EP94109144A patent/EP0630902B1/de not_active Expired - Lifetime
- 1994-06-15 NZ NZ260771A patent/NZ260771A/en unknown
- 1994-06-15 ES ES94109144T patent/ES2128461T3/es not_active Expired - Lifetime
- 1994-06-20 JP JP6137398A patent/JP2749520B2/ja not_active Expired - Fee Related
- 1994-06-23 JP JP6141904A patent/JPH0733782A/ja active Pending
- 1994-06-23 BR BR9402517A patent/BR9402517A/pt not_active IP Right Cessation
- 1994-06-23 BR BR9402516A patent/BR9402516A/pt not_active IP Right Cessation
- 1994-06-24 US US08/265,078 patent/US5430166A/en not_active Expired - Fee Related
- 1994-06-24 CN CN94107819A patent/CN1046527C/zh not_active Expired - Fee Related
- 1994-06-24 MX MX9404815A patent/MX9404815A/es not_active IP Right Cessation
- 1994-06-24 US US08/265,075 patent/US5430167A/en not_active Expired - Fee Related
- 1994-06-24 CN CN94107821A patent/CN1044708C/zh not_active Expired - Fee Related
- 1994-06-24 MX MX9404816A patent/MX9404816A/es not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2039512A (en) * | 1978-12-05 | 1980-08-13 | Oreal | Surface-active polysiloxanes |
| US4847397A (en) * | 1987-05-26 | 1989-07-11 | Dow Corning Kabushiki Kaisha | Method for the production of silyl group containing amine compounds |
Non-Patent Citations (3)
| Title |
|---|
| YUKAGAGU 19,NO.11,23 1970.1.1 牧宏久.堀口恭伸.菅 * |
| YUKAGAGU 19,NO.11,23 1970.1.1 牧宏久.堀口恭伸.菅;YUKAGAGU 19,NO.4,51 1970.1.1 牧宏久.菅孝明.池田 * |
| YUKAGAGU 19,NO.4,51 1970.1.1 牧宏久.菅孝明.池田 * |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2128460T3 (es) | 1999-05-16 |
| EP0630902A1 (de) | 1994-12-28 |
| EP0630901B1 (de) | 1999-01-13 |
| AU6475394A (en) | 1995-01-05 |
| NZ260770A (en) | 1995-12-21 |
| BR9402517A (pt) | 1995-03-14 |
| JP2749520B2 (ja) | 1998-05-13 |
| NZ260771A (en) | 1995-12-21 |
| EP0630901A1 (de) | 1994-12-28 |
| US5430167A (en) | 1995-07-04 |
| CA2124877C (en) | 1999-02-02 |
| CN1106413A (zh) | 1995-08-09 |
| DK0630902T3 (da) | 1999-08-30 |
| CA2124877A1 (en) | 1994-12-25 |
| AU6475294A (en) | 1995-01-05 |
| CN1107477A (zh) | 1995-08-30 |
| DE59407622D1 (de) | 1999-02-25 |
| DE4320920C1 (de) | 1994-06-16 |
| JPH0710884A (ja) | 1995-01-13 |
| CA2124876A1 (en) | 1994-12-25 |
| AU667436B2 (en) | 1996-03-21 |
| ES2128461T3 (es) | 1999-05-16 |
| JPH0733782A (ja) | 1995-02-03 |
| US5430166A (en) | 1995-07-04 |
| DE59407623D1 (de) | 1999-02-25 |
| EP0630902B1 (de) | 1999-01-13 |
| DK0630901T3 (da) | 1999-08-30 |
| MX9404815A (es) | 1995-01-31 |
| BR9402516A (pt) | 1995-03-14 |
| MX9404816A (es) | 1995-01-31 |
| AU668041B2 (en) | 1996-04-18 |
| CN1044708C (zh) | 1999-08-18 |
| CA2124876C (en) | 1998-12-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1046527C (zh) | 具有亲水基团的硅烷及基制备方法和应用 | |
| CN1043895C (zh) | 具有亲水基团的硅烷及其制备方法和应用 | |
| US20200385528A1 (en) | Composition containing platinum | |
| US5475127A (en) | Organosilyl and organosiloxanyl derivatives of glycerin ethers and their use | |
| US6717019B2 (en) | Glycidyl ether-capped acetylenic diol ethoxylate surfactants | |
| JP4319711B2 (ja) | シロキサン−ポリオキシアルキレンコポリマーの製造法 | |
| EP2168970B1 (en) | Method of formulating a coating composition comprising a hydrolysis resistant organomodified silylated surfactant | |
| US6313182B1 (en) | Acetylenic diol ethylene oxide/propylene oxide adducts and processes for their manufacture | |
| CN105585595A (zh) | 制备含铂组合物的方法 | |
| EP2676986A1 (de) | Siliconpolyether und Verfahren zu deren Herstellung aus Methylidengruppen tragenden Polyethern | |
| DE102005039398A1 (de) | Verfahren zur Herstellung von Anlagerungsprodukten aus SiH-Gruppen enthaltenden Verbindungen an Olefingruppen aufweisende Reaktionspartner in wässrigen Medien | |
| DE69306698T2 (de) | Polydiorganosiloxan mit Alkoxyendgruppen und von diesem abgeleitete, bei Umgebungstemperatur vulkanisierbare Siliconelastomere | |
| EP1294459B1 (en) | Defoamers for aqueous systems | |
| DE69411122T2 (de) | Verfahren zur Herstellung von Epoxigruppen-enthaltenden Polysiloxanen | |
| CN111234255B (zh) | 一种水性聚氨酯用超支化有机硅润湿剂及其制备方法 | |
| CN1140491C (zh) | 基于原酸酯的表面活性剂及其制备和应用 | |
| EP2528927B1 (en) | Silicon polyethers and method of producing the same | |
| CN1317257C (zh) | 含氮的原酸酯基表面活性剂、其制备及用途 | |
| EP3986957B1 (en) | Silicone polyether foam control agent | |
| JP4503777B2 (ja) | 変性ビニルエーテル重合体の製造方法 | |
| CN1849377A (zh) | 固体无水复合材料 | |
| CN1126716A (zh) | 具有低动态表面张力的乙氧基化炔二醇 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CI01 | Correction of invention patent gazette |
Correction item: Denomination of Invention Correct: Silane having hydrophilic group and preparation method and application thereof False: Silane with hydrophilic group and base, preparation method and Application Number: 46 Volume: 15 |
|
| ERR | Gazette correction |
Free format text: CORRECT: INVENTION NAME; FROM: SILICANE AND GROUP PREPARATION METHOD AND APPLICATION WITH HYDROPHILIC GROUP TO: SILICANE WITH HYDROPHILIC GROUP, ITS PREPARATION METHOD AND APPLICATION |
|
| C19 | Lapse of patent right due to non-payment of the annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |