US2729572A - Stable solution of an aluminum salt of a methyl silane triol - Google Patents
Stable solution of an aluminum salt of a methyl silane triol Download PDFInfo
- Publication number
- US2729572A US2729572A US290318A US29031852A US2729572A US 2729572 A US2729572 A US 2729572A US 290318 A US290318 A US 290318A US 29031852 A US29031852 A US 29031852A US 2729572 A US2729572 A US 2729572A
- Authority
- US
- United States
- Prior art keywords
- solution
- alkali
- salt
- aluminum
- water
- 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 - Lifetime
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- ZJBHFQKJEBGFNL-UHFFFAOYSA-N methylsilanetriol Chemical compound C[Si](O)(O)O ZJBHFQKJEBGFNL-UHFFFAOYSA-N 0.000 title claims description 22
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 title description 20
- 239000000243 solution Substances 0.000 claims description 60
- -1 ALKALI-METAL SALT Chemical class 0.000 claims description 59
- 229910052783 alkali metal Inorganic materials 0.000 claims description 42
- 239000007864 aqueous solution Substances 0.000 claims description 14
- 239000012736 aqueous medium Substances 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 150000003839 salts Chemical class 0.000 description 17
- 159000000000 sodium salts Chemical class 0.000 description 17
- FKNKOPQPFGPJBL-UHFFFAOYSA-N sodium;trihydroxy(methyl)silane Chemical compound [Na].C[Si](O)(O)O FKNKOPQPFGPJBL-UHFFFAOYSA-N 0.000 description 14
- BNGXYYYYKUGPPF-UHFFFAOYSA-M (3-methylphenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].CC1=CC=CC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BNGXYYYYKUGPPF-UHFFFAOYSA-M 0.000 description 13
- 239000004753 textile Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000011449 brick Substances 0.000 description 7
- 239000004744 fabric Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 238000006386 neutralization reaction Methods 0.000 description 7
- 229920001296 polysiloxane Polymers 0.000 description 7
- 229910000077 silane Inorganic materials 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 5
- 239000005871 repellent Substances 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 230000003472 neutralizing effect Effects 0.000 description 4
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 4
- 238000004078 waterproofing Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000007605 air drying Methods 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 238000009877 rendering Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- HDYRYUINDGQKMC-UHFFFAOYSA-M acetyloxyaluminum;dihydrate Chemical compound O.O.CC(=O)O[Al] HDYRYUINDGQKMC-UHFFFAOYSA-M 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 229940009827 aluminum acetate Drugs 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(3+);trinitrate Chemical compound [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000002940 repellent Effects 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 229940089952 silanetriol Drugs 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 230000003313 weakening effect Effects 0.000 description 2
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 2
- DWUHNIIHCHDPFT-UHFFFAOYSA-N 1-(2,6-diphenylphenyl)naphthalene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1C1=CC=CC2=CC=CC=C12 DWUHNIIHCHDPFT-UHFFFAOYSA-N 0.000 description 1
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
- XNDZQQSKSQTQQD-UHFFFAOYSA-N 3-methylcyclohex-2-en-1-ol Chemical compound CC1=CC(O)CCC1 XNDZQQSKSQTQQD-UHFFFAOYSA-N 0.000 description 1
- ZUGAOYSWHHGDJY-UHFFFAOYSA-K 5-hydroxy-2,8,9-trioxa-1-aluminabicyclo[3.3.2]decane-3,7,10-trione Chemical compound [Al+3].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O ZUGAOYSWHHGDJY-UHFFFAOYSA-K 0.000 description 1
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229940037003 alum Drugs 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical compound O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- GNFVJWIAXUKASD-UHFFFAOYSA-N benzyl(trihydroxy)silane Chemical class O[Si](O)(O)CC1=CC=CC=C1 GNFVJWIAXUKASD-UHFFFAOYSA-N 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
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010981 drying operation Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- KEYRRLATNFZVGW-UHFFFAOYSA-N ethyl(trihydroxy)silane Chemical class CC[Si](O)(O)O KEYRRLATNFZVGW-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 239000007863 gel particle Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 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
- 230000001771 impaired effect Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 159000000014 iron salts Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 235000019988 mead Nutrition 0.000 description 1
- 239000005055 methyl trichlorosilane Substances 0.000 description 1
- UIUXUFNYAYAMOE-UHFFFAOYSA-N methylsilane Chemical compound [SiH3]C UIUXUFNYAYAMOE-UHFFFAOYSA-N 0.000 description 1
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000005054 phenyltrichlorosilane Substances 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 125000005625 siliconate group Chemical group 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical class Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 1
- FCVNATXRSJMIDT-UHFFFAOYSA-N trihydroxy(phenyl)silane Chemical compound O[Si](O)(O)C1=CC=CC=C1 FCVNATXRSJMIDT-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/20—Macromolecular organic compounds
- D21H17/33—Synthetic macromolecular compounds
- D21H17/46—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D21H17/59—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon
-
- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C17/00—Surface treatment of glass, not in the form of fibres or filaments, by coating
- C03C17/28—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material
- C03C17/30—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material with silicon-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
- C04B41/45—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements
- C04B41/46—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements with organic materials
- C04B41/49—Compounds having one or more carbon-to-metal or carbon-to-silicon linkages ; Organo-clay compounds; Organo-silicates, i.e. ortho- or polysilicic acid esters ; Organo-phosphorus compounds; Organo-inorganic complexes
- C04B41/4905—Compounds having one or more carbon-to-metal or carbon-to-silicon linkages ; Organo-clay compounds; Organo-silicates, i.e. ortho- or polysilicic acid esters ; Organo-phosphorus compounds; Organo-inorganic complexes containing silicon
- C04B41/4922—Compounds having one or more carbon-to-metal or carbon-to-silicon linkages ; Organo-clay compounds; Organo-silicates, i.e. ortho- or polysilicic acid esters ; Organo-phosphorus compounds; Organo-inorganic complexes containing silicon applied to the substrate as monomers, i.e. as organosilanes RnSiX4-n, e.g. alkyltrialkoxysilane, dialkyldialkoxysilane
- C04B41/4927—Alkali metal or ammonium salts
-
- 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
- C07F7/0834—Compounds having one or more O-Si linkage
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/50—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with organometallic compounds; with organic compounds containing boron, silicon, selenium or tellurium atoms
- D06M13/51—Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond
- D06M13/513—Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond with at least one carbon-silicon bond
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21J—FIBREBOARD; MANUFACTURE OF ARTICLES FROM CELLULOSIC FIBROUS SUSPENSIONS OR FROM PAPIER-MACHE
- D21J1/00—Fibreboard
- D21J1/08—Impregnated or coated fibreboard
Definitions
- This invention is concerned with aluminum salts of hydrocarbon-substituted silane triols having reduced alkalinity. More particularly, the object of this invention is the product formed by a process for reducing the pH of aqueous solutions of alkali-metal salts of hydrocarbonsubstituted silane triols which process comprises adding to the said solution a single aluminum salt in an amount sufficient to reduce the pH of the aforesaid alkali-metal salt.
- Alkali-metal salts of hydrocarbon-substituted silane triols have been disclosed as being eminently useful for rendering various bodies water-repellent.
- the use of such alkali-metal salts for the aforesaid stated purpose is more particularly described in Krieble and Elliott Patent 2,507,200, issued May 9, 1950, and assigned to the same assignee as the present invention as Well as in the application of William S. Kather, Serial No. 290,313, filed concurrently herewith and assigned to the same assignee as the present invention.
- alkali-metal salts of hydrocarbon-substituted silane triols
- Elliott and Krieble Patents 2,441,422 and 2,441,423 are disclosed in Elliott and Krieble Patents 2,441,422 and 2,441,423.
- the salts in treating materials such as textiles or paper with the alkali-metal salt, it is desirable to use the salts in the form of aqueous solutions in which to dip the textile or paper. Good water repellency is obtained on such sheet materials by merely drying the treated cloth whereby the carbon dioxide and moisture in the air form a mildly acidic environment which causes condensation of the alkali-metal salt to the hydrocarbon-substituted polysiloxane.
- alkali-metal salts of hydrocarbon-substituted silane triols in the form of aqueous solutions can be readily neutralized to any degree desired down to a pH of about 6.8 to 7.0 by employing as the neutralizing agent a single aluminum salt in an amount sufiicient to give the desired degree of neutralization while at the same time maintaining the stability of the solution.
- the neutralized compositions thereby obtained are effective as Water repellents on various materials including textiles, paper, masonry, etc., and can be used for many applications without necessitating the use of elevated temperatures during drying operations.
- the alkali-metal salt with which the present invention is concerned may be prepared from mono-organosilane triols or their condensation products and are described, for example, by Meads and Kipping, Journal of the Chemical Society, 105, page 679.
- the metallic salts can be prepared, for instance, by hydrolyzing derivatives of a monohydrocarbon-substituted silane containing three hydrolyzable radicals, for instance, halogen atoms, alkoxy radicals, etc., connected to silicon, recovering the hydrolysis products and dissolving these products in an aqueous solution of an alkali-metal hydroxide in such proportion that there is preferably, although not neces sarily, present at least one equivalent of base per silicon atom.
- the resultant solution containing the soluble metallic salt is diluted to the desired concentration, with water or water-soluble alcohols, e. g., ethanol, etc., or both.
- the hydrolyzable monohydrocarhon-substituted silanes mentioned above and used in making the alkali-metal salt maybe considered as having the formula RSiXs Where R is a monovalent hydrocarbon radical, for example, alkyl (e. g., methyl, ethyl, propyl, isopropyl, butyl, hexyl, decycl, etc.), aryl (e.
- sbstituents are, for example, halogens, e. g., chlorine, bromine, fluorine, etc.
- X may be a halogen, for instance, chlorine, bromine, fluorine, etc.; alkoxy, e. g., methoxy ethoxy, propoxy, etc., amino groups, e. g., the -NH2 grouping.
- X is a halogen, particularly chlorme.
- inorganic bases which may be employed in making the alkali-metal salts may be mentioned, for example, potassium hydroxide, sodium hydroxide, cesium hydroxide, etc. 1
- the aqueous alkali-metal salt solution it is desirable when making the aqueous alkali-metal salt solution to obtain it in a concentrated form, for example, in concentrations of the order of about 20 to 50 per cent total solids content (alkali-metal salt) and thereafter dilute it with Water to the desired concentration applicable for the neutralization step.
- the solution contains the alkali-metal salt of the hydrocarbonsubstituted silane triol on a Weight basis of less than 6 per cent organopolysiloxane calculated as RSiO1.s (e. g., CHsSiO1.5) where R is a monovalent hydrocarbon radical.
- single aluminum salt or aluminum salt employed herein is intended to mean single aluminum salts, preferably soluble in water, but necessarily soluble inthe aqueous solution of the alkali-metal salt of the hydrocarbon-substituted silanetriol.
- such salts hydrated or non-hydrated salts
- aluminum halides e. g., aluminum chloride, aluminum bromide, etc.
- aluminum sulfate aluminum nitrate, basic aluminum acetate, aluminum citrate, etc.
- aluminum nitrate would form, e. g., sodium nitrate,'with the alkali-metal salt
- aluminum sulfate would form, e. g., sodium sulfate with the alkali-metal salt, etc.
- Aluminum phosphate would not be satisfactory because in most concentrations in solution it would form a salt with the alkali-metal salt which would be only slightly less basic than the original alkali-metal salt. I have found that the simple aluminum salts are best for the purpose, and if one' employs complex aluminum salts, for example, alum, KAl(SO4)2, the stability of the neutralized solution is materially impaired so that there may be gelation and precipitation after addition of the complex aluminum salt.
- the aluminum salts are unique for the purpose as' far as metallic salts in general are concerned.
- iron salts for instance, ferric nitrate
- metallic salts of tin for instance, stannic chloride
- Zinc salts for instance, zinc nitrate, showed better stability in the neutralized iron or tin solutions, but because of the more expensive nature ofzinc salts, the use of the latter materials is impractical.
- the ratio of the aluminum salt to the alkali-metal salt can be varied widely, depending on the particular alkalimetalsalt employed, the aluminum salt used, the conthe aluminum salt isnot deleterious to the stability of the solution nor to the water-repellency properties of such neutralized solutions.
- optimum molar ratios of the ingredients are those described above.
- EXAMPLE 1 The sodium salt of methylsilane trial was prepared by hydrolyzingl mol of methyltric'hlorosilane by-iadding it, rapidly with stirring to a large excess of water.
- solution 4 amount of water present was substantially in excess over that required to effect complete hydrolysis of all the silicon-bonded chlorine in the methyltrichlorosilane.
- the resultant solution was allowed to stand until substantially all the methylpolysiloxane had precipitated in the form of a fine powder. This powder was filtered from the remaining solution, washed to remove acid, filtered and dried. The solid gel particles were dissolved by stirring in a 50 per cent, by weight, aqueous sodium hydroxide solution. Generally, 1 mol of the methylpolysiloxane is allowed to react with about 1 to 1.05 mols of sodium hydroxide to give the alkali-metal salt, namely, the sodium salt of methylsilane triol.
- the resultant alkaline solution had a total solids content of about 4-67 per cent of which about 14.3 per cent was titrated as sodium oxide and contained about 30 per cent methylpolysiloxane solids calculated as CH3SiO1.5.
- the com position had a specific gravity of about 1.35 to 25 C. and a pH of about 13.
- This sodium salt of methylsilanetriol (which is also known as sodium methyl siliconate) is believed to have structure I in dilute aqueous solution, and it can be dried to a white solid having the structure II asits molecular formula:
- a neutralized solution of the sodium salt of methyl sila'ne triol containing 4.6 per cent methyl polysiloxane (calculatedas 'CHsSiOLs) was prepared by using an aqueous solution of 3.7 mols sodium methyl siliconate to 1 mol of aluminum nitrate. This particular neutralized solution had a pH of 9.
- EXAMPLE 3 This example illustrates another method for preparing the neutralized solutions (that is, solutions of varying pH and lower than the initial sodium methyl siliconate More particularly, 3.75 grams (0.01 mol)- aluminum nitrate nonahydratewere dissolved in 50 ml. water, and 6.6 grams 0.03 mol CHsSiOzNa) of the aqueous sodium methyl siliconate solution prepared as in Example l were also dissolved in 50 ml. water. The two solutions were heated to about C. and thereafter the aluminum nitrate solution was poured into the sodium methylsiliconate solution with stirring to give a clear solution having a pH of about 6.8.
- EXAMPLE 4 A portion of the sodium methyl siliconate solution prepared in Exa'mpleglwas diluted with water to give a solution containing 2.1 per cent methyl polysiloxane calculated as CH3SiO1.5. Varying amounts of this solution were added to a, solution composed of 2.82 grams aluminum nitrate nonahydrate dissolved in grams water. The following Table I shows the effect in pH change of adding the sodium methyl siliconate solution to the aluminum nitrate solution. The solution of aluminum nitrate in each instance'contained 0.0074 mol aluminum nitrate nonahydr'ate.
- EXAMPLE 5 EXAMPLE 6 In this example 38 grams of basic aluminum acetate were added to a solution consisting of 100 grams (0.44 mol CI-IsSiO1.5) sodium methyl siliconate (30 per cent CH3SiO1.5) dissolved in 900 grams water. This gave a solution having a p H of 8 and contained 2.9 per cent by weight thereof. methyl polysiloxane calculated as CHsSiO1.5
- the sodium salt of methylsilane triol and the neutral ized sodium salt of methylsilane triol (both diluted with water to contain about 1.9 per cent, by weight, of the sodium salt, the said weight being calculated as CH3SlOL5) prepared as in Example 3 were used to treat various textiles by dipping the latter in the solutions of the Water repellent and then air-drying in the case of the sodium methyl siliconate solution and oven-curing the aluminum nitrate neutralized solutions at C. for 5 minutes.
- the invention is not limited to the particular organosilane triols described in the foregoing examples, but other hydrocarbon-substituted silane triol salts may be employed as, for example, the metallic salts of phenylsilane triol (which may be prepared by hydrolyzing phenyltrichlorosilane and dissolving the hydrolysis product in a strong inorganic base), ethylsilane triol, benzylsilane triol, tolylsilane triol, etc.., salts.
- phenylsilane triol which may be prepared by hydrolyzing phenyltrichlorosilane and dissolving the hydrolysis product in a strong inorganic base
- ethylsilane triol which may be prepared by hydrolyzing phenyltrichlorosilane and dissolving the hydrolysis product in a strong inorganic base
- ethylsilane triol which may be prepared by hydrolyzing phenylt
- the concentrations of the alkali-metal salts in water described above prior to neutralization are not intended to be limiting and lower or higher concentrations of such alkali-metal salts may be employed Within the scope of the invention.
- the particular water-soluble single aluminum salt employed may also be varied as long as it maintains the stability of the solution without causing undesirable precipitation or gelation.
- the concentration of the aluminum salt added to the alkali-metal salt for neutralization purposes may be varied within wide limits depending, as pointed out above, on the type of alkali-metal salt employed, the specific aluminum salt used for the purpose, the degree of neutralization desired, etc.
- compositions herein defined are eminently suitable for rendering water-repellent all kinds of solid bodies including textiles, paper, porcelain, glass, ceramics, and various types of masonry, for instance, concrete, gypsum, etc.
- the disadvantage of weakening the paper or cloth which is inherent in the use of the alkali-metal salts, is materially obviated so that no diiference in the strength of the paper tqxti s is apna entbeiore or after treatm nt i h; the qu r lized -m .ta1 a1 What I c as new; and desire to secure by Letters Patent gof; the United States; is:
- A- stable solutionhaving a pH of from 6.8 to 10 comprising the product oi reaction in an aqueous medium of.
- a stable solution having a pH of from 6.8. to 10 comprising the product of reaction in an aqueous medium of (1) an aqueous solution of a Water-soluble alkalimetal salt of methyl silanetriol having the formula wherein the concentration in the aqueous solution ofthe alkali-metal salt when calculated as CHsSiO1.5 is less than 6%, by Weight, and (2) aluminum nitrate which is present in an amount equal to from 0.001 to 0.4 mol of the latter for each mol ofthe aforesaid sodium salt.
- a stable solution having-gag pH of from 6.8 to 10 comprising the product of reaction in an aqueous medium of (l a water-soluble alkali-metal salt of methyl silanetriol having the-formula wherein the concentration in the aqueous solution of the alkali-metal salt When calculated as CH3SiO1.5 is less than 6%, by weight, and (2) aluminum sulfate which is present in an amount equal to from. 0.001 to 0.4 mol for each mol of the sodium salt.
- a stable solution having a pH- of from 6.8 to 10 comprising the product of reaction in an aqueous medium of (1) an aqueous, solution of a sodium salt of methyl silanetriol having the formula OH 3HaS i -ON11 wherein the'concentration in the aqueous solution of the latter sodium salti'when calculated as'CHsSiO1.5 is less than 6%; by'weight and (2) aluminum nitrate, there beings present from- 0:0,01' to (M mol of the aluminum nitrate'ror each mol of? the sodium salt of the methyl silanetriol;
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Ceramic Engineering (AREA)
- Materials Engineering (AREA)
- Textile Engineering (AREA)
- Structural Engineering (AREA)
- Inorganic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Geochemistry & Mineralogy (AREA)
- Silicon Polymers (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Curing Cements, Concrete, And Artificial Stone (AREA)
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BE520123D BE520123A (xx) | 1952-05-27 | ||
US290318A US2729572A (en) | 1952-05-27 | 1952-05-27 | Stable solution of an aluminum salt of a methyl silane triol |
GB14316/53A GB738693A (en) | 1952-05-27 | 1953-05-21 | Improvements in and relating to neutralized solutions of alkali-metal salts of hydrocarbon-substituted silane triols |
DEG11844A DE1028077B (de) | 1952-05-27 | 1953-05-27 | Stabile waessrige Loesungen von Siliconaten zur Wasserfestimpraegnierung von festen Gegenstaenden aller Art |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US290318A US2729572A (en) | 1952-05-27 | 1952-05-27 | Stable solution of an aluminum salt of a methyl silane triol |
Publications (1)
Publication Number | Publication Date |
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US2729572A true US2729572A (en) | 1956-01-03 |
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ID=23115456
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US290318A Expired - Lifetime US2729572A (en) | 1952-05-27 | 1952-05-27 | Stable solution of an aluminum salt of a methyl silane triol |
Country Status (4)
Country | Link |
---|---|
US (1) | US2729572A (xx) |
BE (1) | BE520123A (xx) |
DE (1) | DE1028077B (xx) |
GB (1) | GB738693A (xx) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4281147A (en) * | 1979-03-05 | 1981-07-28 | Th. Goldschmidt Ag | Process for the production of aqueous solutions of alkali organosiliconates |
EP0058818A1 (de) * | 1981-02-24 | 1982-09-01 | Hüls Troisdorf Aktiengesellschaft | Imprägnierungsmittel für cellulosehaltiges Material |
US4565577A (en) * | 1983-07-26 | 1986-01-21 | Dynamit Nobel Ag | Pollutant-resistant sealing composition |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1572397A (en) * | 1976-06-11 | 1980-07-30 | Dow Corning Ltd | Fibre treatment composition and process |
JPS5826892A (ja) * | 1981-08-06 | 1983-02-17 | ミネソタ・マイニング・アンド・マニユフアクチユアリング・コンパニ− | 被覆および接着剤組成物 |
DE3370360D1 (en) * | 1982-12-08 | 1987-04-23 | Giulini Chemie | Agent and process for neutral sizing |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2438055A (en) * | 1947-01-10 | 1948-03-16 | Corning Glass Works | Preparation of salts of monoorgano silanols |
US2507200A (en) * | 1945-02-10 | 1950-05-09 | Gen Electric | Process for rendering materials water-repellent and compositions therefor |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2441422A (en) * | 1945-02-10 | 1948-05-11 | Gen Electric | Organosilicon-silica sols, gels, and aerogels |
DE831292C (de) * | 1950-12-31 | 1952-02-11 | Wacker Chemie Gmbh | Verfahren zur Beschleunigung der Kondensation von Polysiloxanen |
-
0
- BE BE520123D patent/BE520123A/xx unknown
-
1952
- 1952-05-27 US US290318A patent/US2729572A/en not_active Expired - Lifetime
-
1953
- 1953-05-21 GB GB14316/53A patent/GB738693A/en not_active Expired
- 1953-05-27 DE DEG11844A patent/DE1028077B/de active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2507200A (en) * | 1945-02-10 | 1950-05-09 | Gen Electric | Process for rendering materials water-repellent and compositions therefor |
US2438055A (en) * | 1947-01-10 | 1948-03-16 | Corning Glass Works | Preparation of salts of monoorgano silanols |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4281147A (en) * | 1979-03-05 | 1981-07-28 | Th. Goldschmidt Ag | Process for the production of aqueous solutions of alkali organosiliconates |
EP0058818A1 (de) * | 1981-02-24 | 1982-09-01 | Hüls Troisdorf Aktiengesellschaft | Imprägnierungsmittel für cellulosehaltiges Material |
US4424075A (en) | 1981-02-24 | 1984-01-03 | Dynamit Nobel Ag | Impregnating compositions for cellulose containing materials |
US4565577A (en) * | 1983-07-26 | 1986-01-21 | Dynamit Nobel Ag | Pollutant-resistant sealing composition |
Also Published As
Publication number | Publication date |
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DE1028077B (de) | 1958-04-17 |
GB738693A (en) | 1955-10-19 |
BE520123A (xx) |
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