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 PDF

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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
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solution
alkali
salt
aluminum
water
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Torkelson Arnold
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General Electric Co
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General Electric Co
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Priority to US290318A priority patent/US2729572A/en
Priority to GB14316/53A priority patent/GB738693A/en
Priority to DEG11844A priority patent/DE1028077B/de
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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)
US290318A 1952-05-27 1952-05-27 Stable solution of an aluminum salt of a methyl silane triol Expired - Lifetime US2729572A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
BE520123D BE520123A (de) 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

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US290318A US2729572A (en) 1952-05-27 1952-05-27 Stable solution of an aluminum salt of a methyl silane triol

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BE (1) BE520123A (de)
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Cited By (3)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Patent Citations (2)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

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DE1028077B (de) 1958-04-17
GB738693A (en) 1955-10-19

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