US2588365A - Method of rendering fabrics waterrepellent and product resulting therefrom - Google Patents

Method of rendering fabrics waterrepellent and product resulting therefrom Download PDF

Info

Publication number
US2588365A
US2588365A US126690A US12669049A US2588365A US 2588365 A US2588365 A US 2588365A US 126690 A US126690 A US 126690A US 12669049 A US12669049 A US 12669049A US 2588365 A US2588365 A US 2588365A
Authority
US
United States
Prior art keywords
fabrics
mixture
parts
fabric
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
Application number
US126690A
Inventor
Firth L Dennett
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dow Silicones Corp
Original Assignee
Dow Corning Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to BE498183D priority Critical patent/BE498183A/xx
Application filed by Dow Corning Corp filed Critical Dow Corning Corp
Priority to US126690A priority patent/US2588365A/en
Priority to GB21987/50A priority patent/GB680265A/en
Priority to FR1025150D priority patent/FR1025150A/en
Priority to DED6426A priority patent/DE925225C/en
Application granted granted Critical
Publication of US2588365A publication Critical patent/US2588365A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • 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
    • D06M15/6436—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing amino groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/12—Polysiloxanes containing silicon bound to hydrogen
    • 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
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/01—Silicones
    • 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
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2164—Coating or impregnation specified as water repellent
    • Y10T442/218—Organosilicon containing

Description

Patented Mar. 11, 1952 METHOD OF RENDERING FABRICS WATER-e REPELLENT AND PRODUCT RESULTING THEREFROM 'Firth L. Bennett, Midland, Mich., assignor to Dow Corning Corporation, Midland, Mich.,. a
corporation of Michigan No Drawing. Application November 10, 1949, Serial No. 126,690
3 Claims.
This invention relates to a method of rendering fabrics water-repellent.
Siloxanes for treating fabrics to renderthem water-repellent have heretofore been known. Mark-off is a serious problem in connection with the heretofore known compositions. Marl:- off is the appearance of lines when the treated fabric is folded or otherwise wrinkled. Mark-01f appears especially in such fabrics as nylon, orlon and rayon of either viscose or acetate type. Heretofore, when the treated fabric was laundered or dry cleaned, a considerable amount of the objectional mark-off was noted.
It is an object of the present invention to provide a method whereby fabrics are rendered substantially water-repellent even after laundering and dry cleaning.
It is another oject of the present invention to eliminate or materially reduce mark-oil in fabrics rendered water-repellent, such as nylon, orlon and rayon of either viscose or acetate type.
It is a further object of the present invention to render fabrics water-repellent whereby the fabrics after treatment possess good hand and drape, and are of better crease resistance.
In accord with the present invention, fabrics are rendered water-repellent by wetting the fabrics with a mixture of two organosiloxane polymers. The fabrics so wetted are then heated at a temperature ranging from 100 to 475 F. for a period of from seconds to 1 hour.
The fabrics which may be treated in accord with the method of the present invention include fabrics of natural materials such as cotton, linen, silk or wool and fabrics. of artificial material such as nylon, orlon and rayon of either viscose or acetate type.
One of the siloxane polymers used in the above stated mixture is a methylhydrogenpolysiloxane fluid which contains between 1.0 and 1.5 methyl radicals and between 0.75 and 1.25 hydrogen atomsbonded to silicon per silicon atom, there being a total of 2 to 2.25 methyl radicals and hydrogen atoms per silicon atom. Fluids of this type may be produced by the hydrolysis and con densation of CH3HS1C12 alone or by cohydrolyzing and condensing it with a chlorosilane, such as (CH3)3SiCl; (Cl-mzl-lsiCl; and (CH3)2SiC1z.
The other siloxane polymer used in the above stated mixture is a methylpolysiloxane fluid which contains between 2 and 2.1 methyl radicals per silicon atom and which has a viscosity of at least 1,000 centistokes and preferably less than 100,000 centistokes. Such fluids and their preparation have been described in the art and are now well-known commercially. They may be produced by cohydrolyzing and condensing a mixture of methyl chlorosilanes of the general average formula (CHs)nSiCl4 n where n has a value of from 2 to 2.1.
From 20 to '70 per cent by weight of the total mixture consists of the methylpolysiloxane and the remaining to 30 per cent consists of the methylhydrogenpolysiloxane.
Catalysts may be added to the mixture of organosiloxanes, and the mixturethen used to wet the fabric. Alternatively the fabric may be wetted with the organosiloxane mixture and the fabric dippedin a solution of the catalyst. Such catalysts include metallic salts such as sodium bicarbonate, sodium aluminate and iron, cobalt, manganese, lead and zinc salts of carboxylic acids such as acetates, octoates and naphthenates.
This organosiloxane mixture may be applied directly to the fabric.- However, it is preferred to extend the organosiloxane mixture by diluting with a liquid hydrocarbon, chlorohydrocarbon, ether or alcohol, such as benzene, dioxane, ethanol or the like inorder to minimize the amount employed.
The organosiloxane mixture may likewise be extended by the preparation of an aqueous emulsion, which emulsion preferably contains an emulsifying agent decomposible by heating. The quaternary ammonium halides are examples of such emulsifying agents. They are decomposed on heating for a brief period before the fabric is damaged by the heating. Examples of such halides are the alkylarylammonium chlorides, such as trimethylbenzylammonium chloride and hexadecyldimethylbenzylanimonium chloride. If desired, the siloxane mixture may be thinned with any of the above indicated solvents in order to facilitate emulsification. After emulsification, the solvent may be removed under vacuum, if desired.
Emulsions of methylhydrogenpolysiloxanes frequently liberate hydrogen upon standing. In order to avoid this effect, it is accordingly desirable to add an organic acid such as acetic acid to the emulsion in order to inhibit the evolution of hydrogen. The quaternary ammonium salts function well as emulsifying agents in such acid syfiilfims.
The siloxane mixture either straight or as a solution or emulsion may be applied to the fabric in any appropriate manner. Thus, the fabric may be dipped in the mixture. The mixture may be applied to the fabric by the use of conven tional equipment such as a padder or ql etch.
The fabric may then be dried to remove water or solvent.
The material should be applied to the fabric in such amount that there is between 1 and 5 per cent of the organosiloxane mixture based upon the weight of the fabric.
The fabric is then heated to between 100 and 475 F. for from 5 seconds to 1 hour. This heating efifects liberation of a major portion of the hydrogen which is bonded to the silicon in the methylhydrogenpolysiloxane. The decomposition product is polymerized to an insoluble polymer in the fabric, whereby the fabric is rendered permanently hydrophobic. When a heat decomposable emulsifying agent is employed, it is also decomposed during thisheating.
The present invention is of particular importance in the hydrophobing of nylon and acetate rayon. In manufacturing filaments of these materials, the filaments are extruded in a molten state and the extrusion stretched while soft.
This results in a strain in the filaments. Frequently the fabrics are woven without the strain in the filaments being relaxed. Such a fabric may be wetted with a siloxane in accord with this invention. After wetting, the fabric is contacted with a hot surface at a temperature of 400 to 475 F. for from 5 to 80 seconds. This heat treatment serves a dual purpose, first, to set the siloxane polymer and second, to effect relaxation of the filament. The use of the siloxane improves the ironability of the fabric, since the coated fabric does not adhere to the iron nor do the fibers cohere even when slightly softened.
Fabrics treated in accord herewith are substantially water-repellent both after laundering and after dry cleaning. The contact angle between a drop of water and the surface of a fabric so treated is about 110. Treated fabrics of cotton, linen, wool, nylon, orlon and rayon are soft to the touch and have a good hand. Nylon, orlon and rayon fabrics so treated have a reduced tendency to show mark-off.
The following polysiloxanes were prepared:
A mixture of, 9.3 parts by weight of decamethyltetrasiloxane and 735 parts of octamethylcyclotetrasiloxane was prepared. To this mixture there were added .56 part of KOH. This mixtures was then heated at 160 C. for 8 hours. The mixture was then cooled to about 100 C. and CO2 in the form of Dry Ice was added over a period of 30 minutes. This mixture was then filtered and flash distilled to 250 C. at 1 mm. pressure. There were obtained 625 parts of a trimethylsiloxy end-blocked dimethylpolysiloxane fluid having a viscosity of 1,000 centistokes, which is referred to as product I in the examples.
A mixture was prepared of 1.5 parts by weight of decamethyltetrasiloxane and 735 parts of octamethylcyclotetrasiloxane. To this mixture there were then added .56 part of KOH. This mixture was'then agitated and heated at 160 C. for 8 hours. The mixture was then cooled to about 100 C. and CO2 in the form of Dry Ice added over a period of 30 minutes. The mixture was then filtered and flash distilled to 250 C. at 1 mm. pressure. There were obtained 630 parts of a trimethylsiloxy end-blocked dimethylpolysiloxane fluid having a viscosity of 12,500 centistokes, which is referred to as product II in the examples.
A mixture was prepared of 1.2 parts by weight of decamethyltetrasiloxane and 735 parts of octamethylcyclotetrasiloxane. To this mixture there was then added .56 part of KOH. The mixture was then agitated-and heated at 160 C. for
8 hours. The mixture was then cooled to C.
To this mixture 675 parts of isopropyl alcohol were added over a period of 10 minutes and then 783 parts of water were added over a period of 1 hour, whereby to effect hydrolysis. An additional 750 parts of benzene were then added to the reaction mixture. The product was washed six times with water and strip distilled at 3 mm. pressure to C. to remove the benzene and the lower boiling products. There were obtained 475 parts of a trimethylsiloxy end-blocked methylhydrogenpolysiloxane, which is referred to as product IV in the examples.
In the following examples, which are illustrative only, the spray rating was determined by standard test method 22-41 of the American Association of Textile Chemists and Colorists.
Example 1 A mixture was prepared of 24 parts by weight of product IV and 6 parts of product I. To this siloxane mixture there were added 3 parts of hexadecyldimethylbenzylammonium chloride and Example 2 A mixture was prepared of 24 parts by weight of product IV and 6 parts of product II. To this siloxane mixture there were then added 3 parts of hexadecyldimethyl-benzylammonium chloride and 0.1049 of acetic acid. The resulting mixture was then emulsified with 967 parts of water using a colloid mill. This produced an emulsion containing 3 per cent siloxane. The emulsion was employed for treating acetate rayon. One sample of the fabric was heated aftertreating at a temperature of C. for 5 minutes. Following this the fabric had a spray rating of 90. The fabric was next Washed with soap, following which it had a spray ratin of 80 to 90. It was noted that the fabric was free of objectionable mark-off.
Example 3 A mixture was prepared of 18 parts by weight of product IV, 15 parts of water, 19 parts of toluene and 12 parts of product II. To this siloxane mixture there were then added 3 parts of hexadecyldimethylbenzylammonium chloride. The resulting mixture was then emulsified with 942 parts of water using a colloid mill. The emulsion produced contained 3 per cent of siloxane. This emulsion was employed for treating the following fabrics for and minutes at 150 C. giving the spray rating indicated.
5 min./ 10 min./ 150 C. 150 C ('1?) Muslin 90 90 (2) Plaid Twill 90 100 (3) Acetate Sharkskin 90 100 The rayon fabric was free of objectionable marl;- off.
Example 4 ing in the indicated spray ratings:
(1) Muslin 100 (2) Olive elkskin (cotton and viscose rayon) 100 (3) W001 twill 90 (4) Acetate sharkskin 100 (5) Acetate French crepe 70 (6) Acetate satin 70 (7) Acetate and rayon faille 90-100 (8) Viscose rayon suiting 100 The treated fabrics had a good hand, and the rayon fabrics were free of objectionable markoff.
Example 5 A mixture was prepared of 354 parts by weight of methylene chloride, 248.5 parts of water and 177 parts of product III. To this mixture there were then added 17 parts of hexadecyldimethylbenzylammonium chloride, and the mixture emulsified using a colloid mill. This emulsion was added to 154 parts of product IV. 10,000 parts of water were then added to the emulsion. The mixture was then emulsified using a colloid mill. The following fabrics Were treated for 5 minutes at 150 C. after which time the fabrics had the spray ratings indicated:
(1) Muslin 80 (2) Cotton twill 80 (3) Acetate rayon 90 (4) Nylon tenting M 100 The fabrics all had a good hand and the rayon and nylon fabrics were free of objectionable mark-off.
Example 6 A solution was prepared of 194 parts by weight of toluene, 3.6 parts of product IV and 2.4 parts of product II. Acetate rayon twill fabric was coated with this solution and the fabric cured for 10 minutes at 450 F. Following this, the fabric had a spray rating of 80. The fabric had a good hand and was free of objectionable markoff.
Example 7 A solution was prepared of 194 parts by weight of toluene, 2.4 parts of product IV and 3.6 parts of product II. An acetate rayon twill was coated with this solution and cured for 10 minutes at 150 0. Following this, the spray rating was 80.
The fabric was soft and was free of objectionable mark-off.
Example 8 A solution was prepared of 194 parts by weight of toluene, .78 part of product IV and 5.22 parts of product II. Acetate rayon twill was coated with this solution and cured for 10 minutes at 150 C. Following this, the spray rating of the fabric was 90. The fabric had a good hand. The fabric was" free of objectionable mark-off. Following dry cleaning the fabric had a spray rating of 70.
Example 9 A mixture was prepared of 1405 parts by weight of product IV, 935 parts of product II and 1260 parts of methylene chloride. To this siloxane mixture there were then added 234 parts of hexadecyldimethylbenzylammonium chloride. The resulting mixture was then emulsified with 2016 parts of water using a colloid mill. The emulsion produced was diluted with 52,650 parts of Water. This gave an emulsion containing 4 per cent of siloxane. This emulsion was employed for treating the following fabrics for 5 minutes at 150 C. giving the spray rating indicated:
(1) Muslin 100 (2) Cotton twill 100 (3) Orlon 100 (4) Nylon 100 (5) Nylontenting 100 (6) W001 100 (7) Acetate twill 100 (8) Acetate sharkskin 100 All of the above fabrics had a soft hand, and the rayon, nylon and orlon fabrics were free of objectionable mark-off.
That which is claimed is:
1. The method of rendering organic fabrics l. water-repellent, which comprises wetting the fabrics with a mixture of from 20 to '70 per cent by Weight of a methylpolysiloxane containing between 2 and 2.1 methyl radicals per silicon atom and having a viscosity of at least 1,000 centistokes v and less than 100,000 centistokes, and from 80 to 30 per cent of a methylhydrogenpolysiloxane containing between 1.0 and 1.5 methyl radicals and between 0.75 and 1.25 hydrogen atoms bonded to silicon per silicon atom, there being a total of 2 to 2.25 methyl radicals and hydrogen atoms per silicon atom, and heating the wetted fabrics at a temperature of from to 475 F. for a period of from 5 seconds to 1 hour, whereby the fabrics are rendered water-repellent.
2. The method of rendering organic fabrics water-repellent, which comprises wetting the fabrics with an aqueous emulsion of a mixture of from 20 to 70 per cent by weight of a methylpolysiloxane containing between 2 and 2.1 methyl radicals per silicon atom and having a viscosity of at least 1,000 centistokes and less than 100,000 centistokes, and from 80 to 30 per cent of a methylhydrogenpolysiloxane containing between 1.0 and 1.5 methyl radi als and between 0.75 and 1.25 hydrogen atoms bonded to silicon per silicon atom, there being a total of 2 to 2.25 total methyl radicals and hydrogen atoms bonded to silicon per silicon atom, which emulsion contains a trialkylbenzylammonium chloride as an emulsifying agent, and heating the wetted fabric at a temperature of from 100 to 475 F. for a period of from 5 seconds to 1 hour, whereby the fabrics are rendered water-repellent and the emulsifying agent is decomposed.
3. An organic textile fabric coated with between 1 and 5 per cent based upon the weight of the fabric of a polymerized mixture of from 20 to 70 per cent by weight of a methylpolysiloxane containing between 2 and 2.1 methyl radicals per silicon atom and having a viscosity of at least 1,000 centistokes and less than 100,000 centistokes, and from 80 to 30 per cent of a methylhydrogenpolysiloxane containing between 1.0 and 1.5 methyl radicals and between 0.75 and 1.25 hydrogen atoms bonded to silicon per silicon atom, there being a total of 2 to 2.25 methyl radicals and hydrogen atoms per silicon atom.
FIRTH L. DENNETT.
REFERENCES CITED The following references are of record in the file of this patent:
Number 8 UNITED STATES PATENTS Name Date Rochow Oct. '7, 1941 Britton June 9, 1942 Patnode Dec. 22, 1942 Tucker Mar, 16, 1943 McGregor Sept. 4, 1945 Morton Oct. 9, 1945 Hyde Dec. 4, 1945 Biefeld Jan. 15, 1946 Sarbach Feb.- 19, 1946 West Mar. 26, 1946 Tanis, Jr. Oct. 8, 1946 Hyde Apr. 13, 1948 Welsh Sept. 21, 1948 Wilcox Dec. 20, 1949 Warrick Jan. 17, 1950 MacKenzie Mar. 14, 1950 Rust Nov. 7, 1950

Claims (1)

1. THE METHOD OF RENDERING ORGANIC FABRIC WATER-REPELLENT, WHICH COMPRISES WETTING THE FABRICS WITH A MIXTURE OF FROM 20 TO 70 PER CENT BY WEIGHT OF A METHYLPOLYSILOXANE CONTAINING BETWEEN 2 TO 2.1 METHYL RADICALS PER SILICON ATOM AND HAVING A VISCOSITY OF AT LEAST 1,000 CENTISTOKES AND LESS THAN 100,000 CENTISTOKES, AND FROM 80 TO 30 PER CENT OF A METHYLHYDROGENPOLYSILOXANE CONTAINING BETWEEN 1.0 AND 1.5 METHYL RADICALS AND BETWEEN 0.75 AND 1.25 HYDROGEN ATOMS BONDED TO SILICON PER SILICON ATOM, THERE BEING A TOTAL OF 2 TO 2.25 METHYL RADICALS AND HYDROGEN ATOMS PER SILICON ATOM, AND HEATING THE WETTED FABRICS AT A TEMPERATURE OF FROM 100* TO 475* F. FOR A PERIOD OF FROM 5 SECONDS TO 1 HOUR, WHEREBY THE FABRICS ARE RENDERED WATER-REPELLENT.
US126690A 1949-11-10 1949-11-10 Method of rendering fabrics waterrepellent and product resulting therefrom Expired - Lifetime US2588365A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
BE498183D BE498183A (en) 1949-11-10
US126690A US2588365A (en) 1949-11-10 1949-11-10 Method of rendering fabrics waterrepellent and product resulting therefrom
GB21987/50A GB680265A (en) 1949-11-10 1950-09-06 Improvements in or relating to rendering fabrics water-repellent
FR1025150D FR1025150A (en) 1949-11-10 1950-09-14 Fabric waterproofing process
DED6426A DE925225C (en) 1949-11-10 1950-09-30 Impregnating agents and processes for finishing, in particular for making fabrics water-repellent

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US126690A US2588365A (en) 1949-11-10 1949-11-10 Method of rendering fabrics waterrepellent and product resulting therefrom

Publications (1)

Publication Number Publication Date
US2588365A true US2588365A (en) 1952-03-11

Family

ID=22426204

Family Applications (1)

Application Number Title Priority Date Filing Date
US126690A Expired - Lifetime US2588365A (en) 1949-11-10 1949-11-10 Method of rendering fabrics waterrepellent and product resulting therefrom

Country Status (5)

Country Link
US (1) US2588365A (en)
BE (1) BE498183A (en)
DE (1) DE925225C (en)
FR (1) FR1025150A (en)
GB (1) GB680265A (en)

Cited By (39)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2702276A (en) * 1951-04-10 1955-02-15 Du Pont Water-dispersible emulsions of polysiloxanes
US2738290A (en) * 1951-10-01 1956-03-13 Deering Milliken Res Corp Process of treating textiles and textile treating compound
US2757152A (en) * 1952-09-23 1956-07-31 Gen Electric Water-repellent compositions comprising a polysiloxane, a urea-or melamine-formaldehyde resin and a curing agent
US2758946A (en) * 1952-09-23 1956-08-14 Gen Electric Silicone water-repellent compositions
US2774690A (en) * 1951-04-16 1956-12-18 Bradford Dyers Ass Ltd Water repellent treatment utilizing a methylhydrogenpolysiloxane and a titanium compound
US2789956A (en) * 1952-07-09 1957-04-23 Wacker Chemie Gmbh Methylhydrogenpolysiloxane composition for treating textile
US2803614A (en) * 1954-03-15 1957-08-20 Gen Electric Tin compound as a curing agent for organopolysiloxanes
US2807601A (en) * 1954-04-29 1957-09-24 Dow Corning Compositions for treating organic fabrics and a method of applying them
US2854424A (en) * 1955-11-22 1958-09-30 Gen Electric Silicone water-repellents containing stannous salts and process of treating textiles therewith
US2911324A (en) * 1955-01-04 1959-11-03 Bradford Dyers Ass Ltd Treatment of materials to improve water-repellency
US2914836A (en) * 1957-06-25 1959-12-01 Dow Corning Method of making synthetic pile fabrics
US2927870A (en) * 1956-08-28 1960-03-08 Dow Corning Zirconium acetate-zinc acetate catalyzed organohydrogenosiloxane emulsions and the treatment of fabrics therewith
US2952892A (en) * 1956-07-19 1960-09-20 Bancroft & Sons Co J Cellulosic fabric finishing
US2976185A (en) * 1955-12-12 1961-03-21 Du Pont Coated polymeric thermoplastic dielectric film
US3009833A (en) * 1958-03-07 1961-11-21 Ici Ltd Rendering fibrous materials water-repellent
US3024081A (en) * 1956-05-28 1962-03-06 Dow Chemical Co Process for preparing coated synthetic fibers from normally crystalline polymers
US3032442A (en) * 1955-04-15 1962-05-01 American Cyanamid Co Process of finishing textiles with silicone-colloidal melamine resin mixtures, composition and resultant article
US3058936A (en) * 1956-09-24 1962-10-16 Ucb Sa Waterproofing emulsion containing a hydrogen silicone and a catalyst and method of waterproofing therewith
US3077460A (en) * 1955-08-17 1963-02-12 Celanese Corp Composition comprising an organopolysiloxane and colloidal silica, and textile treated therewith
US3167448A (en) * 1961-08-23 1965-01-26 Monsanto Co Process of treating fabrics with ethylene carbonate and article produced therefrom
US3211580A (en) * 1959-11-21 1965-10-12 Bayer Ag Process for the treatment of materials with silicones
US3251794A (en) * 1962-07-13 1966-05-17 Celanese Corp Treating vehicle for polyester filamentary material and method of improving the properties of such material
US3271189A (en) * 1962-03-02 1966-09-06 Beaunit Corp Process of treating synthetic fibers
US3361586A (en) * 1964-10-01 1968-01-02 Du Pont Process of treating polyimide surface with polyalkylenimines and polyalkylene polyamines
US3419423A (en) * 1964-10-09 1968-12-31 Dow Corning Adducts of silicon hydride polysiloxanes and hydrolyzable silanes having alkenyl radicals useful for rendering substrates water repellent
US3423236A (en) * 1964-10-09 1969-01-21 Dow Corning Adducts of silicon hydride polysiloxanes and silanes having alkenyl radicals
US3433667A (en) * 1964-01-22 1969-03-18 Dow Corning Polishing cloth
US3436251A (en) * 1964-08-04 1969-04-01 Midland Silicones Ltd Process for rendering paper abrasion resistant,adhesive and water-repellent employing siloxane composition
US3445276A (en) * 1965-08-04 1969-05-20 Union Carbide Corp Textile materials coated with hydrolytically stable siloxane-oxyalkylene block copolymers containing sih
US3454422A (en) * 1964-03-13 1969-07-08 Du Pont Organopolysiloxane coated filling materials and the production thereof
US3485661A (en) * 1966-09-16 1969-12-23 Dow Corning Polyamide and polyester fabrics treated with isocyanate functional siloxanes
US3488217A (en) * 1968-02-29 1970-01-06 Du Pont Process for imparting a soft feel to textile fiber and the resulting fiber
US3494788A (en) * 1967-04-26 1970-02-10 Dow Corning Antisoiling treatment of a fibrous material and the treated material
US3639154A (en) * 1968-07-20 1972-02-01 Kanegafuchi Spinning Co Ltd Process for manufacturing fibrous structure having excellent recovery from extension by treatment with polyorganosiloxane and a polyethylene glycol or derivative thereof
US3989545A (en) * 1974-04-11 1976-11-02 Kanebo, Ltd. Separators for a storage battery
US4098572A (en) * 1976-06-11 1978-07-04 Dow Corning Limited Curable polysiloxane aqueous emulsion with Na or Mg sulfate, and treating of keratinous fibres
US4137179A (en) * 1976-07-21 1979-01-30 Th. Goldsmith Ag Process for the production of an aqueous preparation for shrink-proofing wool
US4456542A (en) * 1980-10-29 1984-06-26 Wacker Chemie Gmbh Method for imparting hydrophobic properties to fibers
US5171464A (en) * 1988-08-31 1992-12-15 Bayer Aktiengesellschaft Lubricant based on polyorganosiloxanes

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE553033A (en) * 1955-11-30
US2911327A (en) * 1956-08-07 1959-11-03 Dow Corning Leather article
DE1287918B (en) * 1958-03-26 1900-01-01
FR2624873B1 (en) * 1987-12-18 1992-01-10 Rhone Poulenc Chimie MAGNETISABLE COMPOSITE PARTICLES BASED ON CROSSLINKED ORGANOPOLYSILOXANE, THEIR PREPARATION PROCESS AND THEIR APPLICATION IN BIOLOGY
WO2009106718A1 (en) 2007-12-20 2009-09-03 Bluestar Silicones France Room-temperature vulcanisable organopolysiloxane compound to give an elastomer and novel organopolysiloxane polycondensation catalysts
FR2946657A1 (en) 2009-06-12 2010-12-17 Bluestar Silicones France METHOD FOR SEALING AND ASSEMBLING COMPONENTS OF A MOTOR-PROPELLER GROUP
FR2946656A1 (en) 2009-06-12 2010-12-17 Bluestar Silicones France METHOD FOR SEALING AND ASSEMBLING COMPONENTS OF A MOTOR-PROPELLER GROUP
FR2946654A1 (en) 2009-06-15 2010-12-17 Bluestar Silicones France PROCESS FOR COATING A SILICONE COMPOSITION CONTAINING NO TIN ON A FLEXIBLE SUPPORT
FR2946655A1 (en) 2009-06-15 2010-12-17 Bluestar Silicones France PROCESS FOR COATING A SILICONE COMPOSITION CONTAINING NO TIN ON A FLEXIBLE SUPPORT
EP2729533B1 (en) 2011-07-07 2020-10-14 ELKEM SILICONES France SAS Uses of carbenes in solution as organopolysiloxane polycondensation catalysts
FR3000090A1 (en) 2012-12-20 2014-06-27 Bluestar Silicones France METHOD AND COMPOSITIONS USEFUL FOR SEALING AND ASSEMBLING COMPONENTS OF A MOTOR-PROPELLER GROUP
CN104981524B (en) 2012-12-20 2020-03-13 埃肯有机硅法国简易股份公司 Organopolysiloxane compositions vulcanizable at ambient temperature into elastomers and novel organopolysiloxane polycondensation catalysts
US9512294B2 (en) 2012-12-20 2016-12-06 Bluestar Silicones France Sas Organopolysiloxane composition suitable for vulcanisation into an elastomer at room temperature and new organopolysiloxane polycondensation catalysts
JP6134006B2 (en) 2012-12-20 2017-05-24 ブルースター・シリコーンズ・フランス・エスアエス Articles with antifouling properties intended for underwater applications, especially marine applications
FR2999980A1 (en) 2012-12-20 2014-06-27 Bluestar Silicones France ARTICLE HAVING ANTIFOULING PROPERTIES AND INTENDED FOR USE IN AQUATIC APPLICATIONS, IN PARTICULAR MARINE
FR3014107A1 (en) 2013-12-03 2015-06-05 Bluestar Silicones France ARTICLE HAVING ANTIFOULING PROPERTIES AND INTENDED FOR USE IN AQUATIC APPLICATIONS, IN PARTICULAR MARINE
FR3014106B1 (en) 2013-12-03 2017-03-10 Bluestar Silicones France CURABLE SILICONE COMPOSITION IN THE PRESENCE OF WATER OR HUMIDITY IN THE AIR
FR3020067A1 (en) 2014-04-18 2015-10-23 Bluestar Silicones France METHOD FOR COATING A SILICONE COMPOSITION ON A FLEXIBLE SUPPORT
ES2939273T3 (en) 2017-06-29 2023-04-20 Elkem Silicones France S A S Procedure for manufacturing silicone elastomer molds

Citations (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2258218A (en) * 1939-08-01 1941-10-07 Gen Electric Methyl silicones and related products
US2285562A (en) * 1939-07-29 1942-06-09 Dow Chemical Co Styrene copolymer composition
US2306222A (en) * 1940-11-16 1942-12-22 Gen Electric Method of rendering materials water repellent
US2314111A (en) * 1940-10-29 1943-03-16 Standard Oil Co Coating mineral aggregates
US2384384A (en) * 1942-02-26 1945-09-04 Corning Glass Works Polymeric silicone and methods of making it
US2386259A (en) * 1942-07-30 1945-10-09 Gen Electric Waterproofing treatment of materials
US2390370A (en) * 1943-10-11 1945-12-04 Corning Glass Works Manufacture of glass yarn
US2392805A (en) * 1943-10-11 1946-01-15 Owens Corning Fiberglass Corp Glass fiber strand
US2395070A (en) * 1943-06-10 1946-02-19 Goodrich Co B F Chlorine containing carbonic estersynthetic rubber composition
US2397451A (en) * 1943-02-12 1946-03-26 American Cyanamid Co Textile finishing
US2408822A (en) * 1942-07-30 1946-10-08 Gen Electric Electrical discharge device
US2439689A (en) * 1948-04-13 Method of rendering glass
US2449572A (en) * 1944-08-11 1948-09-21 Gen Electric Polysiloxane resins
US2491843A (en) * 1946-03-21 1949-12-20 Gen Electric Liquid linear methylpolysiloxanes
US2494920A (en) * 1945-07-25 1950-01-17 Corning Glass Works Method of coating with organopolysiloxanes
US2500842A (en) * 1944-02-08 1950-03-14 Montclair Res Corp Aminotriazine-organosilicon composition
US2528554A (en) * 1943-11-03 1950-11-07 Montclair Res Corp Water-repellent textiles and process of making same

Patent Citations (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2439689A (en) * 1948-04-13 Method of rendering glass
US2285562A (en) * 1939-07-29 1942-06-09 Dow Chemical Co Styrene copolymer composition
US2258218A (en) * 1939-08-01 1941-10-07 Gen Electric Methyl silicones and related products
US2314111A (en) * 1940-10-29 1943-03-16 Standard Oil Co Coating mineral aggregates
US2306222A (en) * 1940-11-16 1942-12-22 Gen Electric Method of rendering materials water repellent
US2384384A (en) * 1942-02-26 1945-09-04 Corning Glass Works Polymeric silicone and methods of making it
US2386259A (en) * 1942-07-30 1945-10-09 Gen Electric Waterproofing treatment of materials
US2408822A (en) * 1942-07-30 1946-10-08 Gen Electric Electrical discharge device
US2397451A (en) * 1943-02-12 1946-03-26 American Cyanamid Co Textile finishing
US2395070A (en) * 1943-06-10 1946-02-19 Goodrich Co B F Chlorine containing carbonic estersynthetic rubber composition
US2392805A (en) * 1943-10-11 1946-01-15 Owens Corning Fiberglass Corp Glass fiber strand
US2390370A (en) * 1943-10-11 1945-12-04 Corning Glass Works Manufacture of glass yarn
US2528554A (en) * 1943-11-03 1950-11-07 Montclair Res Corp Water-repellent textiles and process of making same
US2500842A (en) * 1944-02-08 1950-03-14 Montclair Res Corp Aminotriazine-organosilicon composition
US2449572A (en) * 1944-08-11 1948-09-21 Gen Electric Polysiloxane resins
US2494920A (en) * 1945-07-25 1950-01-17 Corning Glass Works Method of coating with organopolysiloxanes
US2491843A (en) * 1946-03-21 1949-12-20 Gen Electric Liquid linear methylpolysiloxanes

Cited By (39)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2702276A (en) * 1951-04-10 1955-02-15 Du Pont Water-dispersible emulsions of polysiloxanes
US2774690A (en) * 1951-04-16 1956-12-18 Bradford Dyers Ass Ltd Water repellent treatment utilizing a methylhydrogenpolysiloxane and a titanium compound
US2738290A (en) * 1951-10-01 1956-03-13 Deering Milliken Res Corp Process of treating textiles and textile treating compound
US2789956A (en) * 1952-07-09 1957-04-23 Wacker Chemie Gmbh Methylhydrogenpolysiloxane composition for treating textile
US2757152A (en) * 1952-09-23 1956-07-31 Gen Electric Water-repellent compositions comprising a polysiloxane, a urea-or melamine-formaldehyde resin and a curing agent
US2758946A (en) * 1952-09-23 1956-08-14 Gen Electric Silicone water-repellent compositions
US2803614A (en) * 1954-03-15 1957-08-20 Gen Electric Tin compound as a curing agent for organopolysiloxanes
US2807601A (en) * 1954-04-29 1957-09-24 Dow Corning Compositions for treating organic fabrics and a method of applying them
US2911324A (en) * 1955-01-04 1959-11-03 Bradford Dyers Ass Ltd Treatment of materials to improve water-repellency
US3032442A (en) * 1955-04-15 1962-05-01 American Cyanamid Co Process of finishing textiles with silicone-colloidal melamine resin mixtures, composition and resultant article
US3077460A (en) * 1955-08-17 1963-02-12 Celanese Corp Composition comprising an organopolysiloxane and colloidal silica, and textile treated therewith
US2854424A (en) * 1955-11-22 1958-09-30 Gen Electric Silicone water-repellents containing stannous salts and process of treating textiles therewith
US2976185A (en) * 1955-12-12 1961-03-21 Du Pont Coated polymeric thermoplastic dielectric film
US3024081A (en) * 1956-05-28 1962-03-06 Dow Chemical Co Process for preparing coated synthetic fibers from normally crystalline polymers
US2952892A (en) * 1956-07-19 1960-09-20 Bancroft & Sons Co J Cellulosic fabric finishing
US2927870A (en) * 1956-08-28 1960-03-08 Dow Corning Zirconium acetate-zinc acetate catalyzed organohydrogenosiloxane emulsions and the treatment of fabrics therewith
US3058936A (en) * 1956-09-24 1962-10-16 Ucb Sa Waterproofing emulsion containing a hydrogen silicone and a catalyst and method of waterproofing therewith
US2914836A (en) * 1957-06-25 1959-12-01 Dow Corning Method of making synthetic pile fabrics
US3009833A (en) * 1958-03-07 1961-11-21 Ici Ltd Rendering fibrous materials water-repellent
US3211580A (en) * 1959-11-21 1965-10-12 Bayer Ag Process for the treatment of materials with silicones
US3167448A (en) * 1961-08-23 1965-01-26 Monsanto Co Process of treating fabrics with ethylene carbonate and article produced therefrom
US3271189A (en) * 1962-03-02 1966-09-06 Beaunit Corp Process of treating synthetic fibers
US3251794A (en) * 1962-07-13 1966-05-17 Celanese Corp Treating vehicle for polyester filamentary material and method of improving the properties of such material
US3433667A (en) * 1964-01-22 1969-03-18 Dow Corning Polishing cloth
US3454422A (en) * 1964-03-13 1969-07-08 Du Pont Organopolysiloxane coated filling materials and the production thereof
US3436251A (en) * 1964-08-04 1969-04-01 Midland Silicones Ltd Process for rendering paper abrasion resistant,adhesive and water-repellent employing siloxane composition
US3361586A (en) * 1964-10-01 1968-01-02 Du Pont Process of treating polyimide surface with polyalkylenimines and polyalkylene polyamines
US3423236A (en) * 1964-10-09 1969-01-21 Dow Corning Adducts of silicon hydride polysiloxanes and silanes having alkenyl radicals
US3419423A (en) * 1964-10-09 1968-12-31 Dow Corning Adducts of silicon hydride polysiloxanes and hydrolyzable silanes having alkenyl radicals useful for rendering substrates water repellent
US3445276A (en) * 1965-08-04 1969-05-20 Union Carbide Corp Textile materials coated with hydrolytically stable siloxane-oxyalkylene block copolymers containing sih
US3485661A (en) * 1966-09-16 1969-12-23 Dow Corning Polyamide and polyester fabrics treated with isocyanate functional siloxanes
US3494788A (en) * 1967-04-26 1970-02-10 Dow Corning Antisoiling treatment of a fibrous material and the treated material
US3488217A (en) * 1968-02-29 1970-01-06 Du Pont Process for imparting a soft feel to textile fiber and the resulting fiber
US3639154A (en) * 1968-07-20 1972-02-01 Kanegafuchi Spinning Co Ltd Process for manufacturing fibrous structure having excellent recovery from extension by treatment with polyorganosiloxane and a polyethylene glycol or derivative thereof
US3989545A (en) * 1974-04-11 1976-11-02 Kanebo, Ltd. Separators for a storage battery
US4098572A (en) * 1976-06-11 1978-07-04 Dow Corning Limited Curable polysiloxane aqueous emulsion with Na or Mg sulfate, and treating of keratinous fibres
US4137179A (en) * 1976-07-21 1979-01-30 Th. Goldsmith Ag Process for the production of an aqueous preparation for shrink-proofing wool
US4456542A (en) * 1980-10-29 1984-06-26 Wacker Chemie Gmbh Method for imparting hydrophobic properties to fibers
US5171464A (en) * 1988-08-31 1992-12-15 Bayer Aktiengesellschaft Lubricant based on polyorganosiloxanes

Also Published As

Publication number Publication date
DE925225C (en) 1955-03-17
BE498183A (en) 1900-01-01
FR1025150A (en) 1953-04-10
GB680265A (en) 1952-10-01

Similar Documents

Publication Publication Date Title
US2588365A (en) Method of rendering fabrics waterrepellent and product resulting therefrom
US2588366A (en) Method of rendering fabrics waterrepellent and composition therefor
US2807601A (en) Compositions for treating organic fabrics and a method of applying them
DE60014811T2 (en) Fiber treatment agent containing siloxanes with amine and polyol functionality
CA1129158A (en) Treatment of textile fabrics with epoxy-polyoxyalkylene modified organosilicones
EP0342834B1 (en) Treatment of fibrous materials
CA1322433C (en) Fiber treatment agent composition
US2927870A (en) Zirconium acetate-zinc acetate catalyzed organohydrogenosiloxane emulsions and the treatment of fabrics therewith
US3208971A (en) Bis-silyl ureas and copolymers thereof
JP3007711B2 (en) Fiber treatment agent
KR20110070888A (en) Silicate shell microcapsules for treating textiles
US3268465A (en) Composition and method of treating fabrics
JPH0469669B2 (en)
JP2001226878A (en) Composition for treating fiber
CA1299823C (en) Fiber-treatment composition
US2637623A (en) Textile treating compounds and method of applying them to textiles
US2789956A (en) Methylhydrogenpolysiloxane composition for treating textile
JPS6233250B2 (en)
JPH07179762A (en) Organopolysiloxane emulsion and fiber treated with the same emulsion
US3445267A (en) Treatment of glass with silsesquioxanes to improve durability of subsequent silicone treatments to washing
US20020161116A1 (en) Water repellent textile finishes and method of making
US3445276A (en) Textile materials coated with hydrolytically stable siloxane-oxyalkylene block copolymers containing sih
US3209053A (en) Organosilicon cyclic urea derivatives and coatings thereof
US3455878A (en) Adducts of silicon hydrides polysiloxanes and hydrolyzable silanes having alkenyl radicals
JPS60215874A (en) Higher alkyl modified epoxy terpolymer silicones as fiber finish agent