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Publication numberUS3423235 A
Publication typeGrant
Publication dateJan 21, 1969
Filing dateNov 23, 1964
Priority dateNov 23, 1964
Also published asDE1469335A1
Publication numberUS 3423235 A, US 3423235A, US-A-3423235, US3423235 A, US3423235A
InventorsJames Kermit Campbell
Original AssigneeDow Corning
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Organosiloxane-containing finishes for organic fibers
US 3423235 A
Abstract  available in
Previous page
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Claims  available in
Description  (OCR text may contain errors)

United States Patent ORGANOSILOXANE-CONTAINING FINISHES FOR ORGANIC FIBERS James Kermit Campbell, Midland, Mich, assignor to Dow Corning Corporation, Midland, Mich, a corporation of Michigan No Drawing. Filed Nov. 23, 1964, Ser. No. 413,304

U.S. Cl. 117138.8 3 Claims Int. Cl. B06111 15/66 ABSTRACT OF THE DISCLOSURE Certain organosiloxanes are shown compatible with most organic oils and waxes and possessing excellent fiber lubricating properties of conventional silicone fluids. The silicone compositions include waxy materials as well as fluids and are superior to organic fiber finishes. An illustrative example being:

paraflin and hexane placed upon cotton and allowed to dry.

This application relates to organosiloxane-containing finishes for organic fibers.

Dimethylpolysiloxane is a known finish for organic fibers such as thread and yarn. It imparts superior and long lasting lubricity to the fibers, even when high temperatures and loads that would destroy organic finishes are generated on the fiber surface through friction.

For this reason dimethylpolysiloxane-finished threads and yarns are often used in high speed sewing and weaving machines where high friction can cause frequent fiber breakage is nonsilicone fiber finishes are used.

It would be deeirable to dilute siloxane fiber finishes with organic oils and waxes to obtain improved lubricity over pure organic finishes at a reduced cost. Dimethylsiloxane, however, is incompatible with most organic oils and waxes, which makes it difficult to mix with organic materials,

It would further be desirable to develop waxy silicone fiber finishes, but in its usable forms dimethylpolysiloxane is a fluid. Waxy fiber finishes can be used to hold fibers together in a thread or yarn.

This application discloses new silicone compositions that possess the excellent fiber lubricating properties of dimethylpolysiloxane, yet which are compatible with almost all organic oils and waxes. When even minor quantities of the silicone of this application are added to organic oils and waxes, improved organic fiber finishes are obtained at low cost, showing superiority over nonsilicone fiber finishes.

The silicone compositions of this invention include waxy materials as well as fluids, and are superior to organic fiber finishes whether used alone or in com-bination with other materials.

This invention relates to the process of applying to an 3,423,235 Patented Jan. 21, 1969 organic fiber a composition comprising a polymeric siloxane consisting essentially of r (-Si 0-) units and (b) at least one unit per molecule, where R is an alkyl radical with an average of at least 14 carbon atoms and n has a value of 1 to 2, there being an average of from 1 to 12 (b) units for every 20 (a) units present, and there being an average of 4 to (a) units per polymer molecule, whereby a lubricated fiber is formed.

R can be any alkyl radical of at least 14 carbon atoms such as the tetradecyl, octadecyl, eicosyl, and myricyl radicals. Compositions containing mixtures of R groups are acceptable for use in this invention.

If desired, the silicone of this invention can be diluted with an organic diluent in any proportion, though it is preferred to have at least one weight percent of the sillcone of this invention present based on the weight of the diluted composition.

The organic diluent can be a material suitable for use as a fiber lubricant, e.g. any nondrying organic oil such as naphthenic base, paraifinic base, or mixed base petroleum lubricating oils, other hydrocarbon lubricants, such as lubricating oils derived from coal products and synthetic oils, e.g. alkylene polymers (such as polymers of propylene, butylene, etc., and mixtures thereof). Also, alkylene oxide-type polymers, dicarboxylic acid esters, liquid esters of acids of phosphorus, alkyl aromatic hydrocarbons, and synthetic oils of the alkylene oxide-type polymers may be used, eg propylene oxide polymers produced by polymerizing propylene oxide in the presence of water or alcohols such as ethyl alcohol. Esters of ethylene oxide-type polymers, such as acetylated propylene oxide polymers prepared by acetylating propylene oxide polymers containing hydroxyl groups, polyethers prepared from alkylene glycols such as ethylene glycol, fatty acid esters, and other organic oils are all suitable.

The polymeric products prepared from the various alkylene oxides and alkylene glycols may be polyoxyalkylene diols or polyalkylene glycol derivatives; that is, the terminal hydroxy group can remain as such, or one or both of the terminal hydroxy groups can be removed during the polymerization reaction by esterification or etherification.

Synthetic oils of the dicarboxyli acid ester type include those which are prepared by esterification such dicarboxylic acids as adipic acid, azelaic acid, suberic acid, sebacic acid, alkenyl succinic acid, fumaric acid, maleic acid, etc., with alcohols such as :butyl alcohol, hexyl alcohol, 2-ethylhexyl alcohol, dodecyl alcohol, etc. Examples of dibasic (dicarboxylic) acid ester syntheti oils include dibutyl adipate, dihexyl adipate, di-Z-ethylhexyl sebacate, di-n-hexylfumaric polymer.

Synthetic oils of the alkyl aromatic type include those which are prepared by alkylating benzene (e.g., dodecylbenzene, tetradecylbenzene, didodecylbenzene, etc.).

Polyhydric alcohol esters such as esters of trimethylol propane and pentaerythritol are also usable.

Organic waxes such as paraffin, beeswax, r carnauba wax can also be used as the diluent.

It may be desirable to use volatile solvents as part or all of the organic diluent to assist in the application of the composition to the fibers and to enhance the dispersability of the composition. Examples of suitable solvents are isopropanol, benzene, heptane, cyclo hexane, acetone, diethylether, naphtha, trifluorotrichloroethane, dichlorobenzene and carbon tetrachloride.

Mixtures of organic diluents can be used. For example, to weight percent of the silicone of this invention there can be added 45 weight percent of paraffin dissolved in 50 weight percent of heptane. A uniform, fluid dispersion will result that is easily applied to fibers, and which imparts superior lubricity.

It is preferred for the organic diluent, if present at all, to be present in the amount of 50 to 99 weight percent, based on the total weight of the composition, and for essentially all of the rest of the composition to be the silicone of this invention.

If R has an average of at least 20 carbon atoms, the silicones of this invention will tend to be waxy, which is preferred. If R has an average of less than 20 carbon atoms, the silicones of this invention will tend to be fluids, which may be desirable in many circumstances.

The silicones of this invention can be made by equilibrating octamethylcyclotetrasiloxane and (CH3)3SlO SiO units for every 20 units presnt, and the degree of polymerization should not exceed 100 units per molecule, preferably there being no more than 40 of such units per molecule. The degree of polymerization can be controlled by the amount of endblocking units that are present, e.g. [(CH SiO].

The above copolymeric product is then reacted with one or more types of alpha olefin having an average of at least 14 carbon atoms per molecule, the reaction being in the presence of a platinum catalyst with heating to about 100 to 150 C.

The product will be a copoly-mer of i t SltiO and Eli O 0 H3 C 113 where R is defined above. This is the silicone of this invention.

Another method of making the silicones of this invention is to equilibrate octamethylcyclotetrasiloxane with CH3 CH3 RSlOSiR I13 CH3 in the presence of a catalyst such as NaOH. The above disiloxane can be made by reacting tetramethyldisiloxane with the appropriate alpha olefine in the presence of platinum.

The products made by this partaicular process possess higher alkyl groups only on the terminal silicon atoms of each molecule.

The fluid compositions of this invention can be applied to fibers by means of spraying, running the fibers over a pad soaked with the composition, or any other known Way of applying fluids to fibers. The waxy compositions of this invention can be applied by melteing the composition to the fluid form and then applying it, or by running the fibers across the waxy substance, etc.

Any organic fiber can be used in this invention. For example, any yarn or thread made of wool, cotton, rayon, hemp, silk, polypropylene, polyesters such as Dacron, polyamides such as nylon, polyethylene, or cellulose acetate is operative.

The geratest improvements in lubricity tend to occur when cellulosic fibers such as cotton, or acrylic (polyacrylonitrile) fibers are used.

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 Various yarns were areated with 10% toluene solutions of various silicone finishing agents to achieve 1.0% solids on the yarn, based on the weight of the yarn, and allowed to dry.

These yarns were then tested for frictional characteristics against either a ceramic or steel spindle. The yarn was looped over the spindle with a tension at rest of about grams. During the test the yarn traveled over the spindle at yards per minute. Two strain gauges recorded the difference in tension on the yarn before and after passing the spindle to yield a relative measure of the frictional force between the yarn and the spindle. This relative friction was expressed as a number, the lower frictions being expressed by lower numbers.

5 6 The results are shown below:

Relative trlctlon Finishing agent for yarn Cotton yarn Acrylic yarn Steel Ceramic Steel Ceramic spindle spindle spindle spindle None- 12 12 20 4 CH CH OH; R Eli( iOh-a SiR R=C22 and above 7 7 4. 5

C 3 C 3 C 3 R CH (CH SiO( !SIO) SlO)24Sl(CH:)3 R=C z and above 7 7 4. 5 6

H H; I

CH (CH SiO(R SiO) SiO)24Si(CH R=Cis 8 8 5. 5 8


CH CH (CH SiO(R SiO) SiO).-t( SiO 2ASi(CH3)3 R=C 12 6 8.5

H3 H H (CH SiO(R Si0)%a5Si(CH;) R=C1 1 11 8 8 Dimethylpolysiloxane, 350 cs.

This composition is outside of the claims of this invention, and is shown for comparison.

Example 2 When a dispersion of 10 grams of E (CzaHuSlO (S10) CH3 2 (EH3 40 grams of paraffin, and grams of hexane is placed on a cotton thread and allowed to dry, the lubricity of the thread is greatly enhanced, and the heat stability of the lubricating coat is greater than that of a cotton fiber coated with paraffin alone.

Example 3 When a dispersion of 10 g. of

. C 2 C H3 12 5 3 2o units, and

(b) at least one unit per molecule, where R is an alkyl radical with an average of at least 14 carbon atoms,

and n has a value of 1 to 2, there being an average of 1 to 12 (b) units for every 20 (:1) units present, and there being an average of 4 to 100 (a) units present per polymer molecule, and (2) from 99 to 50 weight percent of a compatible diluent selected from the group consisting of nondrying organic oil and wax. 2. The article of claim 1 wherein the fiber is cotton. 3. The article of claim 1 where the fiber is acrylic.

References Cited UNITED STATES PATENTS 2,486,162 10/1949 Hyde 260-4482 X 2,698,817 1/1955 Guenther 117-138.8 2,735,791 2/1956 Peyrot et al 117138.8 X 2,872,356 2/1959 Bull et al 117-1395 3,187,752 6/1965 Glick ll7138.8 X

WILLIAM D. MARTIN, Primary Examiner.

. E. MILLER, J R., Assistant Examiner.

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US2486162 *Feb 26, 1942Oct 25, 1949Corning Glass WorksOrgano-siloxanes
US2698817 *Feb 28, 1951Jan 4, 1955Coats & ClarkSewing thread and method for producing same
US2735791 *Aug 2, 1954Feb 21, 1956 Waterproofing compositions and their
US2872356 *Jun 2, 1955Feb 3, 1959Dow Chemical CoLubrication of synthetic cellulose fibers
US3187752 *Apr 27, 1962Jun 8, 1965American Cyanamid CoNon-absorbable silicone coated sutures and method of making
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US3493425 *Feb 1, 1967Feb 3, 1970Dow CorningLubricated fibers
US3837022 *Mar 30, 1973Sep 24, 1974Phillips Petroleum CoFibers for pillow stuffing
US3844826 *Dec 7, 1972Oct 29, 1974Bayer AgDressing sewing thread to reduced friction
US3853607 *Oct 18, 1973Dec 10, 1974Du PontSynthetic filaments coated with a lubricating finish
US3983272 *Jan 24, 1975Sep 28, 1976Wacker-Chemie GmbhMethod for improving the lubricating properties and imparting antistatic properties to organic fibers
US4035550 *Dec 23, 1974Jul 12, 1977Massachusetts Institute Of TechnologyFiber reinforced composite of high fracture toughness
US4105569 *Feb 7, 1977Aug 8, 1978George A. Goulston Co., Ltd.Yarn finish formulation
US4169905 *Nov 7, 1977Oct 2, 1979Rhone-Poulenc IndustriesProcess for lubricating textile threads
US4171267 *Oct 30, 1978Oct 16, 1979Sws Silicones CorporationOrganopolysiloxane-hydrocarbon oil solutions
US4394414 *May 29, 1981Jul 19, 1983Ppg Industries, Inc.Aqueous sizing composition for glass fibers for use on chopped glass fibers
US4477524 *Sep 23, 1982Oct 16, 1984Ppg Industries, Inc.Aqueous sizing composition for glass fibers for use on chopped glass fibers
US6051316 *Jun 6, 1996Apr 18, 2000Vetrotex FranceSizing composition for composite yarns and composite yarns coated with this composition
US20060280939 *Jun 23, 2006Dec 14, 2006Gale Pacific LimitedPolymeric plastics material and manufacture thereof
U.S. Classification428/391, 528/10, 528/25
International ClassificationD06M15/643, C08G77/04
Cooperative ClassificationD06M2200/40, D06M15/643, C08G77/04, D06M7/00
European ClassificationD06M7/00, D06M15/643, C08G77/04