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Publication numberUS2807601 A
Publication typeGrant
Publication dateSep 24, 1957
Filing dateSep 7, 1954
Priority dateApr 29, 1954
Publication numberUS 2807601 A, US 2807601A, US-A-2807601, US2807601 A, US2807601A
InventorsDennett Firth L
Original AssigneeDow Corning
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Compositions for treating organic fabrics and a method of applying them
US 2807601 A
Abstract  available in
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Claims  available in
Description  (OCR text may contain errors)

Patented Sept. 24, 1957 COMPOSITIONS FOR TREATING ORGANIC FAB- RICS AND A METHOD OF APPLYING'THEM Firth L. Dennett, Midland, Mich., assignor to Dow Corning Corporation, Midland, Mich., a corporation of Michigan N Drawing. Application September 7, 1954, Serial No. 454,613

12 Claims. (Cl. 260-42) This invention relates to an improved organosilicon treatment of organic fabrics.

This application is a continuation-in-part of .applican-ts copending application Serial No. 426,602, filed April 29, 1954 now abandoned, entitled, Compositions for Treating Organic Fabrics and a Method of Applying Them.

It is known in the art that various types of organosilicon compounds render textiles water repellent. In the past one of the methods employed is the use of hydrolyzable silanes such as methylchlorosilanes. Whereas this method gives improved water repellency, it is not satisfactory because of the acid given off during hydrolysis which interferes with the commercial use of the material. Another method known to the art is that of using alkali metal salts of organosilanols. This method produces water repellency but it requires a neutralization of the alkali. This means that an acid rinse is needed and thus adds an extra step in the treatment of the fabric.

The best previously known method of rendering fabrics water repellent has been the treatment of the fabrics with mixtures of hydrogen containing siloxanes and trimethyl end-blocked dimethylsilox'anes as is described in U. S. Patents 2,588,365 and 2,588,366. Briefly this method comprises applying .a mixture of the two siloxanes to the fabric and thereafter heating the treated material until the siloxane has become set. This method has met with great commercial success because it gives a combination of excellent water-repellency, the proper hand and drape and lack of mark off needed for fabric use. This method gives excellent water repellency on practically any kind of fabric and the water repellency remains essentially unchanged after repeated dry cleanings and launderings. However, it has been found that these products described in the aforesaid patents do not prevent shrinkage of wool during laundering even though the water repellency of the wool remains good.

Furthermore, it has been found that fabrics treated with the above materials although resistant to dry cleanmg were not resistant to grease spotting, that is, spots of grease could not'be removed from the fabric by merely cleaning with a solvent Without leaving an unsightly spot. This spot appeared to be due to several factors such as migration of the fabric dye and the siloxane with the solvent as it spreads out from the affected area. When the, solvent evaporates a permanent stain is left on the fabric.

The problem of grease spotting is quite serious with respect to upholstery fabrics such as are used on automobile seats and furniture. When a grease spot occurs on the upholstery of furniture or an automobile seat it is obviously impossible 'to d-ryclean the entire fabric. The only solution is to take a solvent-saturated cloth and attempt to remove the spot in that manner. With a large number of fabrics this inevitably leaves a permanent stain. Often times an even worse stain is produced when the fabric has been treated with the siloxane water repellents described in the aforesaid patents. The staining of fabrics under these conditions is quite a problem in the automotive industry since a certain number of cars will always get grease on the upholstery as they pass down the assembly line. Some of these stains are so pronounced that it is necessary to remove the car from the assembly line and reupholster the seat. This, of course, is quite expensive and it would be highly desirable to have a fabric which could be cleaned by hand in a few seconds.

The applicant has found most unexpectedly that by employing hydroxylated siloxanes as one of the ingredients in the siloxane Water repellents hereinafter described that the spotting of fabrics described above is entirely eliminated.

It is the primary object of this invention to provide a siloxane Water repellent for organic fabrics which while retaining all of the beneficial properties of previously employed siloxane water repellents has the added advantages of preventing grease spotting and solvent spotting of fabrics and of substantially preventing the shrinking of wool during laundering.

This invention relates to compositions of matter composed essentially of (-1) from 5 to by weight of a hydrocarbon soluble polysiloxane in which there is on the average from .05 to 1 silicon bonded H atoms per silicon atom, the remainder of the valences of the silicon atoms being satisfied by oxygen atoms, aliphatic hydrocarbon radicals of less than 6 carbon atoms and up to on the average .1 aryl hydrocarbon radicals per silicon atom, there being an average of from 1.6 to 2.5 inclusive total hydrocarbon radicals and hydrogen atoms per silicon atom, and (2) from 25 to by weight of a hydroxylated poly siloxane having a viscosity of less than 1,000,000 cs. and having an average of from 1.4 to 2 monovalent hydrocarbon radicals per silicon atom.

In accordance with this invention these compositions are applied to any organic fabric by any suitable means and the fabric is thereafter heated until the siloxane is cured. In general, organosilicon compositions are applied to the fabric in amount so that the pick up ranges from .1 to 5% With the preferred range being from 1 to'2% by Weight both ranges being based on the weight of the fabric.

The compositions of this invention may be applied to the organic fabrics in any desired manner such as by dipping or spraying. The compositions can be applied either per se or in the form of solutions or emulsions. In general, for commercial operations, the emulsions are preferred since most fabric makers are not set up to handle solvent solutions. In fact one of the primary advantages of the composition of this invention is that they can be readily emulsified.

After application of the organosilicon compositions of this invention, the fabric is heated to remove any solvent or water and to cure the siloxane. In general the preferred heating temperatures are from to 475 F. Heating at these temperatures for from 5 seconds to 1 hour is usually sufilcient to obtain a satisfactory cure of the siloxane.

If desired curing catalysts such as zinc or iron octoate, lead 2-ethylhexoate, and the like, may be employed to aid the cure of the siloxane,

Hydrogen containing siloxanes (l) which are operattive in this invention must be either liquid or hydrocarbon soluble materials. For the purpose of this invention at least 5 mol percent of the silicon atoms in the siloxane should contain at least one hydrogen atom attached thereto and in general there should be an average of not more than 1 hydrogen atom per silicon atom. The remaining substituent groups on the silicon atoms are any aliphatic hydrocarbon radical having less than 6 carbon atoms. Thus the siloxane may be substituted with methyl, ethyl, vinyl, allyl,.propyl or amyl radicals. The hydrogen atoms may be substituted on a silicon atom containing 1" or more of the, defined hydrocarbon radicals or the hydrogen may be on a silicon atom which contains no hydrocarbon radicals.

Specific examples of siloxanes exemplary of siloxane 1) are methyl hydrogen polysiloxane, ethyl hydrogen polysiloxane; copolymers of methyl hydrogen polysiloxane anddimethylphenylsiloxane; copolymers obtained by cohydrolyzing diethyldichlorosilane, trichlorosilane, and ethyldimethylchlorosilane; copolymers obtained by cohydrolyzing silicon tetrachloride, methyldichlorosilane, dimethyldichlorosilane and triethylchlorosilane; copolymers obtained by cohydrolyzing dimethylmonochlorosilane and ethyldichlorosilane; copolymers obtained by cohydrolyzing vinylmethyldichlorosilane, methyldichlorosilane and ethylmethyldichlorosilane; copolymers obtained by cohydrolyzing monomethylmonochlorosilane, trimethylchlorosilane and methyldichlorosilane; copolymers obtained by cohydrolyzing trimethylchlorosilane, dichlorosilane and dimethyldiclilorosilane; and copolymers obtained by cohydrolyzing phenylmethylmonochlorosilane and methyldichlorosilane. Preferably the siloxane (1) should be substituted with methyl radicals and hydrogen atoms.

Siloxane (2) employed in this invention must be a hydroxylated fluid. These siloxanes contain on the average from 1.4 to '2, preferably from 1.98 to 2, inclusive hydrocarbon radicals per Siatom. Preferably the radicals are aliphatic hydrocarbon radicals of less than 6 carbon atoms such as methyl, ethyl, propyl, amyl, vinyl and allyl. In those fluids having essentially 2 organic radicals per silicon atom the hydroxyl groups are presumably attached to the end Si atoms i. e.,

I! H[sl0],rr When an appreciable amount of monoorganosilicon units are present, some of the OH groups may be along the chains, i. e.,

R: R1 R2 ntosiosiosmon 0H In any case, viscosity of these fluids must be less than 1,000,000 cs. but the lower limit of the viscosity is not critical. In general the fluids contain at least .02% by weight OH groups.

The composition employed in this invention is obtained by merely mixing siloxanes (1) and (2). This may be done by employing a mutual solvent, if desired. Suitable solvents include benzene, toluene and petroleum hydrocarbons. If desired, bothsiloxanes (l) and (2) may contain limited amounts of aromatic hydrocarbon radicals but the presence of large amounts of such radicals should be avoided since they produce inferior water repellency when present in amounts above 10 mol percent.

Siloxanes (1) and (2) may be prepared by any of the methods known to the art. Siloxane (2) is best prepared by the method set forth in the application of 1. Franklin Hyde et al., Serial Number 426,5 60, now Patent No. 2,779,776 filed April 29, 1954. Briefly this method comprises maintaining a siloxane in contact with certain monobasic aqueous acids in a closed system until a constant viscosity of the siloxane is obtained and thereafter washing the siloxane free of acid.

The compositions and method of this invention are applicable to any organic fabric such as, for example, nylon, cotton, wool, linen, rayon, paper, polyacrylonitrile fabrics, vinylchloride-vinylidene chloride fabrics and terephthalic acid-ethylene glycol fabrics. In all cases the fabrics have excellent water vrepellency, hand, drape and freedomfrom mark-off and grease spotting. In addition the compositions prevent wool fabrics from shrinking during laundering and are easily emulsified. The above combinationof properties is not inherent to any other known compositions either organosilicon or organic.

The procedure employed to test the shrinkage of wool fabrics in the following examples comprises-placing. the fabric in water at 140 F. in a standard reversing wheel washing machine. The water was added to the machine 4 until it reached a level of 4 inches above the bottom of the inside cylinder. The water was maintained at 140 F. and the machine was operated for 1 hour. The fabric was then removed and centrifuged in a 20 inch diameter extractor for 5 minutes at a speed of 1750 R. P. M. and thereafter dried in a tumbler drier at a stack temperature of 130 F. for 30 minutes. The fabric was then removed from the drier, sprinkled with water, allowed to stand for 5 minutes and pressed in a fiat bed press until it was dry. The fabric was then measured to the nearest 16th of an inch in order to ascertain the shrinkage.

The term composed esesntially of as employed in the claims means that siloxanes (1) and (2) are the essential ingredients of the compositions of this invention. However other nonessential ingredients may be included in these compositions without departing from the scope of the present invention. For example, monoorganosiloxane resins may be added in minor amounts in order to modify the hand of the fabrics asdesired or organic resins such as urea-formaldehdye, melamine-formaldehyde, vinyl acetate and acrylonitrile resins may be used in conjunction with the instant compositions in order to increase the crease resistance of the fabric, weather resistance and other specific properties.

The following. examples are illustrative only and should not be construed as limiting the invention which is properly delineated in the appended claims.

Example 1 This example shows the superiority of the compositions of this invention over previously employed trimethyl end blocked polysiloxane fluids. Siloxane A. employed below was a mixture of by weight of hydroxyl. end-blocked dimethylpolysiloxane having a viscosity of 13,742 es. and 10% by weight of a trimethyl end-blocked methyl hydrogen polysiloxane having a viscosity of about 25 cs. Siloxane B was a mixture of 90% by Weight of a hydroxyl end-blocked polysiloxane fluid having a viscosity of 400; 000 cs. and 10% by weight of a trimethyl end-blocked methyl hydrogen polysiloxane having a viscosity of about 25 cs. Siloxane C was a mixture of 90% by weight of trimethyl end-blocked dimethylpolysiloxane fluid having a viscosity of 12,500 cs. and 10% by weight trimethyl end-blocked methyl hydrogen polysiloxane having a viscosity of 25 cs: Siloxane D was a mixture of 90% by weight of a trimethyl end-blocked dimethylpolysiloxane having a viscosity of 400,000 cs. and 10% by weight of a. trimethyl end-blocked methyl hydrogen polysiloxane having a viscosity of about 25 cs. Thus it can be seen that siloxanes A and B are within the scope of this invention while siloxanes C and D are not.

Each of the above siloxane mixtures contained 2% by weight of lead Z-ethylhexoate. A 2% by weight xylene solution was prepared from each of the above siloxanes and a piece of O. D. 10 /2 ounce wool flannel shirting was immersed in each solution for a sui'licient time to give a pick up of 1.4% by weight organosiloxane. Each of the wool samples was then air dried and cured 10 minutes at 300 F. Each sample was then subjected to the laundering shown above and the shrinkage after the first and sixth laundering is given in the table below.

First laundering, Sixth laundering, percent shrinkage total percent Siloxane shrinkage Warp Fill Warp F111 Example 2 The siloxane employed in this example was a mixture of 40% by weight of a hydroxy end-blocked dimethyl- Example 3 This example shows the protection of fabric against spotting which is characteristic of the compositions of this invention. A series of hydroxy end-blocked dimethylpolysiloxane fluids having viscosities of 1700 cs., 5000 cs., 25,000 es. and 42,00 cs. respectively were each mixed with a trimethyl end-blocked methyl hydrogen polysiloxane having a viscosity of about 25 es. in amount such that in each case the weight ratio was 40% hydroxyl endblocked fluid and 60% methyl hydrogen fluid. An aqueous emulsion was prepared from each composition employing polyvinyl alcohol and sodium lauryl sulphates as emulsifying agents. The emulsion was diluted until the concentration of the siloxane was about 4% by weight. A piece of upholstery fabric having a nylon face and a cotton back was dipped into each emulsion for a time suflicient to give a 2% by weight siloxane pick up. Each fabric was then passed through drying rolls and thereafter heated minutes at 300 F. In each case a spot of asphalt cement was applied to the fabric and allowed to remain thereon for 5 minutes. In each case the spot was completely removed in about 30 seconds by swabbing the fabric with a piece of cheese cloth impregnated with a standard fabric cleaning solvent. The fabric was then allowed to air dry and no trace of a spot due either to the asphalt or the solvent was observed.

The above procedure was found to be effective on upholstery fabrics composed of 100% cotton, 100% nylon, combinations of rayon and viscose, 100% viscose, combinations of nylon and wool, 100% wool, combinations of polyacrylonitrile fibers and cotton, and combinations of nylon, viscose and metallic thread. Some of the fabrics tested had rubber backing and in all cases complete removal of the grease stain was obtained without spotting.

Example 4 The composition employed in this invention was a 2% by weight petroleum naphtha solution of a mixture of 40% by weight of a hydroxyl end-blocked dimethylpolysiloxane fluid having a viscosity of 129 cs. and 60% by weight of a trimethyl end-blocked methyl hydrogen polysiloxane fluid of 25 cs. viscosity which solution contained 2% by weight of Zinc octoate based on the total Weight of the siloxanes. This solution was applied to a blue nylon upholstery fabric in such a manner that the siloxane pick up was 1.6% by weight. The fabric was air dried and cured 10 minutes at 300 F. Asphalt cement was then placed on the sample and it was completely removed in about 30 seconds by swabbing the fabric with a cloth impregnated with a standard cleaning solvent. No spot remained on the fabric.

Untreated fabrics identical with those employed in Examples 3 and 4 were severely and permanently stained by asphalt cement. This was also true of identical fabrics which had been treated in an identical manner with a mixture of 40% by weight of a trimethyl end-blocked dimethylpolysiloxane fluid of 12,500 cs. viscosity and 60% by weight of a trimethyl end-blocked methylhydrogenpolysiloxane fluid of 25 cs. viscosity.

Example 5 Equivalent results are obtained when liquid copolymers of 90 mol percent MezSiO, 9.5 mol percent HSiOa z and .5 mol percent CaH5Me2SiO1 2; 99.5 mol percent PrHSiO and .5 mol percent Me2HSiO1 2 and .1 mol percent AmMe2SiO1 2, 55 mol percent EtaSiO and 44.9 mol percent MeHSiO are each substituted for the methylhydrogen-polysiloxane in the procedure of Example 3.

Example 6 Equivalent results are obtained when hydroxyl endblocked fluids each having a viscosity of 3000 cs. and having the following compositions; diethylsiloxane, diamylsiloxane, ethylmethylsiloxane and a copolymer of 95 mol percent dimethylsiloxane and 5 mol percent diphenylsiloxane are each substituted for the hydroxyl end blocked dimethylpolysiloxane in the procedure of Example 3.

Example 7 First Tenth laundering, laundering,

percent total shrinkage percent shrinkage Warp 5. 9 6. 7 Fill 3.1 l 1. 4

1 W001 elongated after first wash.

Example 8 Example 7 was repeated except that siloxane (1) was a fluid copolymer of 43.5 mol percent dimethylsiloxane and 56.5 mol percent monomethylsiloxane having a viscosity of 4,692 cs. and containing 37% by weight silicon bonded OH groups. The wool shrinkage was as follows:

That which is claimed is:

1. Composition of matter composed essentially of 1) from 5 to by weight of a hydrocarbon soluble poly siloxane in which there is on the average from .05 to 1 inclusive Si bonded H atoms per silicon atom, the remainder of the valences of the silicon atoms being satisfied by oxygen atoms, aliphatic hydrocarbon radicals of less than 6 carbon atoms and up to on the average of .1 aryl hydrocarbon radicals per silicon atom, there being an average of from 1.6 to 2.5 inclusive total hydrocarbon radicals and hydrogen atoms per silicon atom and (2) from 25 to by weight of a hydroxylated polysiloxane having a viscosity of less than 1,000,000 es. and having an average of from 1.4 to 2 inclusive hydrocarbon radicals per silicon atom of which radicals up to on the average of .1 per silicon atom are aryl hydrocarbon radicals and the remainder are aliphatic hydrocarbon radicals of less than 6 carbon atoms.

2. A composition in accordance with claim 1 wherein all of the hydrocarbon radicals in siloxanes 1) and (2) are methyl radicals.

3. A composition of matter composed essentially of (1) from 5 to 75 by weight of a liquid trimethyl endblocked methylhydrogenpolysiloxane and (2) 25 to 95 by weight of a hydroxylated methylpolysiloxane having on the average from 1.4 to 2 inclusive methyl groups per silicon atom, said hydroxylated siloxanc having a vis cosity of less than 1,000,000 cs. 1

4. A composition of matter composed essentially of (1) from to 75% by weight of a liquid trirnethyl endblocked methylhydrogenpolysiloxane and (2) 25 to 95 by weight of a hydroxylated methylpolysiloxane having on the average from 1.98 to 2 inclusive methyl groups per silicon atom, said hydroxylated siloxane having a viscosity of less than 1,000,000 cs.

5. A method of rendering an organic fabric water repellent and spot resistant which comprises impregnating the fabric with an organosiliconcomposition composed essentially of (1) from 5 to 75% by weight of a hydrocarbon soluble polysiloxane in which there is on the average from .05 to 1 inclusive Si bonded H atoms per silicon atom, the remainder of the 'valences of the silicon atoms being satisfied byv oxygen atoms, aliphatic hydrocarbon radicals of less than 6 carbon'atoms and up to on the average of .1 aryl hydrocarbon radicals per silicon atom, there being an average of from 1.6 to 2.5 inclusive total hydrocarbon radicals and hydrogen atoms per silicon atom and (2) from 25 to 95% by weight of a hydroxylated polysiloxane having a viscosity of less than 1,000,000 cs. and having anaverage of from 1.4 to 2 inclusive hydrocarbon radicals per silicon atom of which radicals up to on the average of .1 per silicon atom are aryl hydrocarbon radicals and the remainder are aliphatic hydrocarbon radicals of less than 6 carbon atoms.

6. A method in accordance with claim 5 in which all of the hydrocarbon radicals in both siloxanes (l) and (2) are methyl radicals.

7. A method in accordance with claim 5 in which siloxane (1) is a liquid copolymer of trimethylsiloxane and methylhydrogensiloxane and siloxane (2) is hydroxylated methylpolysiloxane having a viscosity of less than 1,000,000 es. and having an average of from 1.4 to 2 inclusive methyl radicals per silicon atom.

8. Amethod in accordance with claim 5 in which siloxane (1) is a liquid copolymer of trimethylsiloxane and methylhydrogensiloxane and siloxane (2) is hydroxylated methylpolysiloxane having a viscosity of less than 1,000,000 cs. and having an average of from 1.98

to 2 inclusive methyl radicals per silicon atom.

there is from .05 to 1 inclusive Sibonded H atoms per silicon atom, the remainder of the valences of the silicon atoms being satisfied by oxygen atoms, aliphatic hydrocarbon radicals of less than 6 carbon atoms and up to on the average of .1 arylhydrocarbon radicals per silicon atom, there being an average of from 1.6 to 2.5 inclusive total hydrocarbon radicals and hydrogen atoms per silicon atom and (2) from 25 to by weight of a hydroxylated polysiloxane having a viscosity of less than 1,000,000 cs. and having an average of from 1.4 to 2 inclusive hydrocarbon radicals per silicon atom of which radicals up to on the average of .1 per silicon atom are aryl hydrocarbon radicals and the remainder are aliphatic hydrocarbon radicals of lessthan 6 carbon atoms.

10. A fabric in accordance with claim 9 in which all of the hydrocarbon radicals in both siloxanes (l) and (2) are methyl radicals.

11. A fabric in accordance with claim 9 in which siloxane (1) is a liquid copolymer of trimethylsiloxane and methylhydrogensiloxane and siloxane (2) is a hydroxylated methylpolysiloxane having a viscosity of less than 1,000,000 cs. and having an average of from 1.4 to 2 inclusive methyl radicals per silicon atom.

12. A fabric in accordance with claim 9 in which siloxane (1) is a liquid copolymer of trimethylsiloxane and methylhydrogensiloxane and siloxane (2) is a hydroxylated methylpolysiloxane having a viscosity of less than 1,000,000 cs. and having an average of from 1.98 to 2 inclusive methyl radicals per silicon atom.

References Cited in the file of this patent UNITED STATES PATENTS 2,482,276 Hyde et al. Sept. 20, 1949 2,588,365 Dennett Mar. 11, 1952 2,588,393 Kauppi Mar. 11, 1952 2,607,792 Warrick Aug. 19, 1952 2,612,482 Rasmussen Sept. 30, 1952

Patent Citations
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US2588365 *Nov 10, 1949Mar 11, 1952Dow CorningMethod of rendering fabrics waterrepellent and product resulting therefrom
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US2607792 *Apr 27, 1949Aug 19, 1952Dow CorningMethod of preparing dimethylpolysiloxane diols
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Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US2920985 *Feb 3, 1956Jan 12, 1960Du PontCoated polymeric thermoplastic dielectric film
US2940875 *Jun 19, 1956Jun 14, 1960Union Carbide CorpSilicone-coated fibrous products and process therefor
US2970363 *Mar 29, 1957Feb 7, 1961Edward LiebmanPile fabric water-repelling and finishing process
US2980557 *Jan 16, 1958Apr 18, 1961Deering Milliken Res CorpNon-felting wool and methods for preparing the same
US2985545 *Mar 26, 1958May 23, 1961Gen ElectricMethod of rendering cellulosic material non-adherent and article produced thereby
US3028347 *Jul 31, 1959Apr 3, 1962Societe des Usines ChimlUhiiccl
US3038821 *Aug 28, 1958Jun 12, 1962Dan River Mills IncWash-fast water-repellent cotton fabric and method
US3042549 *Nov 4, 1958Jul 3, 1962Ralph A ArnoldSilicone treated cotton
US3061567 *Nov 28, 1958Oct 30, 1962Dow CorningAqueous dispersions of a mixture of siloxanes and an aminoplast resin, method of coating, and article obtained
US3065111 *May 7, 1959Nov 20, 1962Chance Leon HSilane-silicone mixture, method of producing the mixture; textile treated with the mixture; and method of impregnating textile with the mixture
US3081193 *Jan 12, 1961Mar 12, 1963Ucb SaProcess for the treatment of polyamide fabrics
US3194680 *Apr 13, 1962Jul 13, 1965Bayer AgProcess for the production of siloxanecoated separating paper
US3251794 *Jul 13, 1962May 17, 1966Celanese CorpTreating vehicle for polyester filamentary material and method of improving the properties of such material
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US3423236 *Oct 9, 1964Jan 21, 1969Dow CorningAdducts of silicon hydride polysiloxanes and silanes having alkenyl radicals
US3433667 *Jan 22, 1964Mar 18, 1969Dow CorningPolishing cloth
US3485661 *Sep 16, 1966Dec 23, 1969Dow CorningPolyamide and polyester fabrics treated with isocyanate functional siloxanes
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US4098572 *May 27, 1977Jul 4, 1978Dow Corning LimitedShrinkage inhibition
US4306990 *Jul 18, 1980Dec 22, 1981Edward GoodmanCleaning and protective composition and method
US5439677 *Feb 24, 1993Aug 8, 1995The Dial Corp.Compositions and methods for treating hair using a mixture of polysiloxanes
US5543082 *Sep 13, 1993Aug 6, 1996Dow Corning CorporationPolysiloxanes
US5585094 *Aug 4, 1995Dec 17, 1996The Dial CorpCompositions and methods for treating hair using a mixture of polysiloxanes
US5629095 *May 18, 1995May 13, 1997Dow Corning CorporationRelease coatings
US5824761 *Jan 16, 1997Oct 20, 1998Dow Corning CorporationRadiation curable compositions containing vinyl ether functionality and methods for their preparation
US5861467 *May 18, 1993Jan 19, 1999Dow Corning CorporationRadiation curable siloxane compositions containing vinyl ether functionality and methods for their preparation
DE1266920B *Jul 18, 1959Apr 25, 1968Bayer AgVerfahren zum Hydrophobieren von Leder
DE1276594B *Jan 31, 1961Sep 5, 1968Midland Silicones LtdVerfahren zum Hydrophobieren von poroesen und faserigen Materialien
Classifications
U.S. Classification528/31, 528/43, 524/267, 442/81, 525/478, 528/18, 428/447
International ClassificationD06L1/04, D06M15/37, D06L1/00, D06M15/643
Cooperative ClassificationD06M15/643, D06L1/04
European ClassificationD06L1/04, D06M15/643