US2575399A - Textile lubricant - Google Patents

Textile lubricant Download PDF

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US2575399A
US2575399A US53377A US5337748A US2575399A US 2575399 A US2575399 A US 2575399A US 53377 A US53377 A US 53377A US 5337748 A US5337748 A US 5337748A US 2575399 A US2575399 A US 2575399A
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parts
weight
cellulose
conditioning
ester
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US53377A
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George W Seymour
Duke Marshall
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Celanese Corp
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Celanese Corp
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    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/244Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
    • D06M13/282Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing phosphorus
    • D06M13/292Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M7/00Treating fibres, threads, yarns, fabrics, or fibrous goods made of other substances with subsequent freeing of the treated goods from the treating medium, e.g. swelling, e.g. polyolefins
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/40Reduced friction resistance, lubricant properties; Sizing compositions

Definitions

  • This invention relates to the treatment of textile materials and relates more. particularly to the lubrication and conditioning of fibers and filaments having a basis of cellulose acetate or other organic derivative of cellulose to render the same more amenable to textile operations such as carding, drafting, spinning, twisting, coning, pirning, hanking, Weaving, knitting, and the like.
  • An object of this invention is the provision of an improved conditioning agent for the treatment of textile materials such as filaments and fibers having a basis of cellulose acetate or other organic derivative of cellulose to render said textile materials more amenable to textile operations.
  • Another object of this invention is the provision of a single-application conditioning agent adapted to be applied to cellulose acetate or other organic derivative of cellulose filaments as said filaments emerge from the spinning cabinet in which they are formed, for lubricating and conditioning the same for the numerous textile operations to which said materials are subjected, either in continuous-filament or staple fiber form, prior to being processed to a finished fabric.
  • a further object of this invention is the conditioning of cellulose acetate or other organic derivative of cellulose staple fibers with a new and improved conditioning agent which renders the cellulose acetate or other organic derivative of cellulose staple fibers treated therewith antistatic and eminently suitable for processing into spun yarns on the cotton system.
  • compositions comprising vegetable, animal and mineral oils, both normal and specially treated, in combination with various other substances have been employed for lubricating and conditioning filaments and staple fibers having a basis of cellulose acetate or other organic derivatives of cellulose to render the same more amenable to the various textile operations generally employed in forming said materials into fabrics.
  • the continuous filaments are usually treated with a suitable lubricant composition as they emerge from the spinning cabinet or metier in which they are formed and then, after a plurality of said lubricated continuous filaments are asso- 2 ciated together in the tom of a bundle or tow, a separate conditioning agent is applied thereto in the desired amount.
  • a separate conditioning agent is applied thereto in the desired amount.
  • the lubricated and conditioned continuous filaments thus obtained are then severed into staple fibers of the desired length.
  • the lubricating composition is applied to impart a suitable degree of flexibility as well 'as desirable frictional qualities so that the staple fibers obtained when the continuous filaments are cut may be processed satisfactorily into fine spun yarns.
  • the conditioning agent is applied to said filaments to render the staple fibers anti- .static so as to avoid the generation of excessive static electricity which would render processing exceedingly difiicult if not impossible.
  • the lubricating and conditioning compositions are applied separately because they are incompatible and, if said compositions are mixed prior to application, they do not produce the desired lubricating and conditioning action. The separate application of each of said compositions is not only uneconomical but is also quite inconvenient.
  • staple fibers of cellulose acetate or other organic derivative of cellulose materials may be satisfactorily lubricated and conditioned for spinning operations by the application thereto of a single-application lubrieating and conditioning composition
  • a single-application lubrieating and conditioning composition comprising a partial ester of phosphoric acid with a long chain aliphatic alcohol, an alkylolamino ester of a long chain aliphatic acid, an alkylolamine such as triethanolamine, diethanolamine, triiso propanolamine or 2-amino-2-methyl-I-propandl and an alkyl phenol such as diamyl phenol; triamyl phenol or dibutyl-m-cresol all mixed into mineral oil in suitable proportions.
  • our novel composition isfree of sulfonated and/or sulfated compounds, not only is the composition thoroughly dispersed over the fibers on application thereto but the fibers obtained are completely anti-static so that a superior degree of lubrication and conditioning is achieved.
  • the long chain aliphatic acid alkylolamino essac-mace tor which we employ in our novel composition is obtained by reaction of an alkylolamine, such as triethanolamine, diethanolamine. triisopropanolamine or 2-amino-2-methyl-l-propanol with a mixture of straight chain aliphatic acids comprising essentially lauric acid and having an average of about 11 to 12 carbon atomain the alkyl chain, exclusive of the carboxyl group present.
  • the carbon chain length usually varies from about to 18 carbon atoms.
  • This aliphatic acid mixture may be obtained as a product of the saponiflcation of commercial cocoanut oil.
  • the saponiflcation reaction yields glycerin and the desired mixture of long chain aliphatic acids which may be separated from the glycerin in a suitable manner and then esteriiled to yield the desired alkylolamine ester.
  • the hydroxy radical of the carboxyl group of the long chain aliphatic acids reacts with one of the hydroxy groups of the triethanolamine, for example, splitting of! water and forming the diethanolamine-ethyl ester of the long chain aliphatic acid.
  • the reaction may be effected employing the necessary stoichiometric proportions of the long chain aliphatic acid mixture and triethanolamine at a temperature of about 110 C.
  • the reaction may be effected at temperatures up to about 200 C. employing any alkylolamine and fatty acid or mixture of fatty acids which is not volatile at the temperature employed.
  • the viscosity is determined in the Saybolt Universal viscometer at 100 F. and,
  • viscosity is embodied hereinafter, it is to be understood as being that obtained in the Saybolt Universal viscometer at a temperature of 100 F.
  • the desired alcohol such as lauryl alcohol, n-octyl alcohol, n-decanol, n-nonyl alcohol or n-undecyl alcohol for example, is reacted with a slight stoichiometric excess of phosphorus pentoxide to form a primary phosphoric acid ester.
  • the temperature is'preferably maintained at about 110 C. with stirring until reaction is completed.
  • n-decanol in forming the primary phosphoric acid ester since the n-decyl phosphoric acid, surprisingly enough, has a lower viscosity than the other corresponding esters, and, therefore, yields a composition of a more desirable viscosity.
  • Our novel composition preferably comprises from 5 to 15 parts by weight of the partial ester of phosphoric acid with n-decanol, 10 to parts by weight of the diethanolamine-ethyl ester of lauric acid, 1 to 4 parts by weight of triethanolamine and 1 to 4 parts by weight of diamyl phenol blended into 50 to 70 parts by weight of acid refined, white mineral oil having a viscosity of
  • the components are preferably combined by adding the n-decyl phosphoric acid partial ester to the mineral oil, with stirring, followed by the addition of the diethanolaminoethyl ester of the long chain aliphatic acids, the triethanolamine and the diamyl phenol. Stirring is continued until a smooth homogeneous blend is obtained.
  • Example I a mixture of coo parts by weight of mixed uct levels of! to about 320 to 340. Cold water is then circulated through the jacket of the vessel and the reaction prod-uct is cooled to room temperature.
  • the product obtained comprises essentially the diethanolamino-ethyl ester of lauric acid.
  • Example 11 parts by weight of n-decanol are introduced into a jacketed reaction vessel provided with a steam coil. With cold water flowing through the jacket, 30 parts by weight of phosphorus pentoxide are introduced into the reaction vessel over the course of about 15 minutes while stirring continuously. The reaction temperature rises to about 120 C. and then gradually goes down to about to C. The reaction mixture is maintained at this temperature by the intermittent use of steam in the heating coil. Reaction is continued at this temperature for about 3 hours while circulating the mixture through the vessel, the mixture being continuously withdrawn from the base of the vessel and reintroduced at the top. The product obtained at the end of the reaction is a clear solution of medium brown color comprising essentially the primary phosphoric acid ester of n-decancl, the alcohol radical replacing one of the hydrogens of the phosphoric acid.
  • Example III The novel lubricating and conditioning agent of our invention is prepared by blending the compounds prepared in accordance with Examples I and II into mineral oil in suitable proportion together with the desired amount of triethanol-.
  • Our novel composition may be applied directly to continuous filaments of cellulose acetate or The lubri- -'sive and its lubricating and conditioning action is-unafiected and unchanged over widely diflerq 'ing conditions of temperature and humidity.
  • Our novel composition may also be employed for lubricating and conditioning other textile materials.
  • a lubricating and conditioning composition comprising essentially of a mixture of 9 parts by weight of the primary ester of phosphoric acid with n-decanol, 20 parts by weight of the diethanolamino-ethyl ester of lauric acid, 2.5 parts by weight of triethanolamine and 2.5 parts by weight of diamyl phenol blended into parts by weight of mineral oil.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Description

Patented Nov. 20, 1951 TEXTILE LUBBJCAN T George W. Seymour, Maplewood, N. .L, and Marshall Duke, Cumberland, Md., asaignors to Celanese Corporation of America, a corporation of Delaware No Drawing. Application October 7, 1948, Serial No. 53,377
2 Claims.
This invention relates to the treatment of textile materials and relates more. particularly to the lubrication and conditioning of fibers and filaments having a basis of cellulose acetate or other organic derivative of cellulose to render the same more amenable to textile operations such as carding, drafting, spinning, twisting, coning, pirning, hanking, Weaving, knitting, and the like.
An object of this invention is the provision of an improved conditioning agent for the treatment of textile materials such as filaments and fibers having a basis of cellulose acetate or other organic derivative of cellulose to render said textile materials more amenable to textile operations.
Another object of this invention is the provision of a single-application conditioning agent adapted to be applied to cellulose acetate or other organic derivative of cellulose filaments as said filaments emerge from the spinning cabinet in which they are formed, for lubricating and conditioning the same for the numerous textile operations to which said materials are subjected, either in continuous-filament or staple fiber form, prior to being processed to a finished fabric.
A further object of this invention is the conditioning of cellulose acetate or other organic derivative of cellulose staple fibers with a new and improved conditioning agent which renders the cellulose acetate or other organic derivative of cellulose staple fibers treated therewith antistatic and eminently suitable for processing into spun yarns on the cotton system.
Other objects of this invention will appear from the following detailed description.
Various compositions comprising vegetable, animal and mineral oils, both normal and specially treated, in combination with various other substances have been employed for lubricating and conditioning filaments and staple fibers having a basis of cellulose acetate or other organic derivatives of cellulose to render the same more amenable to the various textile operations generally employed in forming said materials into fabrics. In order to process continuous filaments of cellulose acetate or other organic derivative of cellulose material into staple fiber suitable for the production of fine spun yarns, the continuous filaments are usually treated with a suitable lubricant composition as they emerge from the spinning cabinet or metier in which they are formed and then, after a plurality of said lubricated continuous filaments are asso- 2 ciated together in the tom of a bundle or tow, a separate conditioning agent is applied thereto in the desired amount. The lubricated and conditioned continuous filaments thus obtained are then severed into staple fibers of the desired length.
The lubricating composition is applied to impart a suitable degree of flexibility as well 'as desirable frictional qualities so that the staple fibers obtained when the continuous filaments are cut may be processed satisfactorily into fine spun yarns. The conditioning agent is applied to said filaments to render the staple fibers anti- .static so as to avoid the generation of excessive static electricity which would render processing exceedingly difiicult if not impossible. The lubricating and conditioning compositions are applied separately because they are incompatible and, if said compositions are mixed prior to application, they do not produce the desired lubricating and conditioning action. The separate application of each of said compositions is not only uneconomical but is also quite inconvenient. The development of a'single composition which could be applied, for example, to continuous filaments of cellulose or other organic derivatives of cellulose as they emerge from the spinning cabinet or metier where they are Iormed', which will produce the desired lubricating and conditioning action on cellulose acetate or other organic derivative of cellulose staple fiber materials and which is prepared with only a limited number of easily available components has long been sought.
We have now found that staple fibers of cellulose acetate or other organic derivative of cellulose materials may be satisfactorily lubricated and conditioned for spinning operations by the application thereto of a single-application lubrieating and conditioning composition comprising a partial ester of phosphoric acid with a long chain aliphatic alcohol, an alkylolamino ester of a long chain aliphatic acid, an alkylolamine such as triethanolamine, diethanolamine, triiso propanolamine or 2-amino-2-methyl-I-propandl and an alkyl phenol such as diamyl phenol; triamyl phenol or dibutyl-m-cresol all mixed into mineral oil in suitable proportions. Although our novel composition isfree of sulfonated and/or sulfated compounds, not only is the composition thoroughly dispersed over the fibers on application thereto but the fibers obtained are completely anti-static so that a superior degree of lubrication and conditioning is achieved.
The long chain aliphatic acid alkylolamino essac-mace tor which we employ in our novel composition is obtained by reaction of an alkylolamine, such as triethanolamine, diethanolamine. triisopropanolamine or 2-amino-2-methyl-l-propanol with a mixture of straight chain aliphatic acids comprising essentially lauric acid and having an average of about 11 to 12 carbon atomain the alkyl chain, exclusive of the carboxyl group present. The carbon chain length usually varies from about to 18 carbon atoms. This aliphatic acid mixture may be obtained as a product of the saponiflcation of commercial cocoanut oil. The saponiflcation reaction yields glycerin and the desired mixture of long chain aliphatic acids which may be separated from the glycerin in a suitable manner and then esteriiled to yield the desired alkylolamine ester. In forming the aliphatic acid alkylolamine ester, the hydroxy radical of the carboxyl group of the long chain aliphatic acids reacts with one of the hydroxy groups of the triethanolamine, for example, splitting of! water and forming the diethanolamine-ethyl ester of the long chain aliphatic acid. The reaction may be effected employing the necessary stoichiometric proportions of the long chain aliphatic acid mixture and triethanolamine at a temperature of about 110 C. and continuing the reaction until the viscosity of the reaction product is reduced to about 320 to 340. The reaction may be effected at temperatures up to about 200 C. employing any alkylolamine and fatty acid or mixture of fatty acids which is not volatile at the temperature employed. The viscosity is determined in the Saybolt Universal viscometer at 100 F. and,
where the term "viscosity is embodied hereinafter, it is to be understood as being that obtained in the Saybolt Universal viscometer at a temperature of 100 F.
In forming the desired phosphoric acid partial ester of along chain aliphatic alcohol, the desired alcohol. such as lauryl alcohol, n-octyl alcohol, n-decanol, n-nonyl alcohol or n-undecyl alcohol for example, is reacted with a slight stoichiometric excess of phosphorus pentoxide to form a primary phosphoric acid ester. In carrying out the reaction the temperature is'preferably maintained at about 110 C. with stirring until reaction is completed. We preferably employ n-decanol in forming the primary phosphoric acid ester since the n-decyl phosphoric acid, surprisingly enough, has a lower viscosity than the other corresponding esters, and, therefore, yields a composition of a more desirable viscosity.
Our novel composition preferably comprises from 5 to 15 parts by weight of the partial ester of phosphoric acid with n-decanol, 10 to parts by weight of the diethanolamine-ethyl ester of lauric acid, 1 to 4 parts by weight of triethanolamine and 1 to 4 parts by weight of diamyl phenol blended into 50 to 70 parts by weight of acid refined, white mineral oil having a viscosity of In forming said lubricating and conditioning compositions, the components are preferably combined by adding the n-decyl phosphoric acid partial ester to the mineral oil, with stirring, followed by the addition of the diethanolaminoethyl ester of the long chain aliphatic acids, the triethanolamine and the diamyl phenol. Stirring is continued until a smooth homogeneous blend is obtained.
In order further to illustrate our invention, but without being limited thereto, the following examples are given:
Example I a mixture of coo parts by weight of mixed uct levels of! to about 320 to 340. Cold water is then circulated through the jacket of the vessel and the reaction prod-uct is cooled to room temperature. The product obtained comprises essentially the diethanolamino-ethyl ester of lauric acid.
Example 11 parts by weight of n-decanol are introduced into a jacketed reaction vessel provided with a steam coil. With cold water flowing through the jacket, 30 parts by weight of phosphorus pentoxide are introduced into the reaction vessel over the course of about 15 minutes while stirring continuously. The reaction temperature rises to about 120 C. and then gradually goes down to about to C. The reaction mixture is maintained at this temperature by the intermittent use of steam in the heating coil. Reaction is continued at this temperature for about 3 hours while circulating the mixture through the vessel, the mixture being continuously withdrawn from the base of the vessel and reintroduced at the top. The product obtained at the end of the reaction is a clear solution of medium brown color comprising essentially the primary phosphoric acid ester of n-decancl, the alcohol radical replacing one of the hydrogens of the phosphoric acid.
Example III The novel lubricating and conditioning agent of our invention is prepared by blending the compounds prepared in accordance with Examples I and II into mineral oil in suitable proportion together with the desired amount of triethanol-.
amine and diamyl phenol.
Thus, 60 parts by weight of acid-refined white mineral oil having a viscosity of 50 are introduced into a blending vessel, 9 parts by weight of the primary n-decyl phosphate, prepared in accordance with Example II, then added followed by the addition of 20 parts by weight of the diethanolamino-ethyl ester of lauric acid prepared in accordance with Example I. To the mixture obtained are then added 2.5 parts byweight of triethanolamine and 2.5 parts by weight of diamyl phenol and the whole stirred until a smooth, homogeneous mixture is obtained. The resulting mixture comprises the improved single action lubricating and conditioning agent of our invention.
Our novel composition may be applied directly to continuous filaments of cellulose acetate or The lubri- -'sive and its lubricating and conditioning action is-unafiected and unchanged over widely diflerq 'ing conditions of temperature and humidity.
Examples of other organic derivative of cellulose materials which may be lubricated-and conditioned with said composition are cellulose' esters such as cellulose propionate, cellulose butyrate, cellulose acetate-propionate and cellulose =acetate-butyrate and cellulose ethers, such as *ethyl cellulose and benzyl cellulose. Our novel composition may also be employed for lubricating and conditioning other textile materials.
It is to be understood that the foregoing detailed description is given merely by way illustration and that many variations may be made therein without departing from the spirit of our invention.
Having described our invention, what we deconsisting essentially of a mixture of 5 to parts by weight 01 the primary ester of phosphoric acid with n-decanol, 10 to parts by weight of the diethanolamino-ethyl ester of lauric acid, 1 to 4 parts by weight of triethanolamine and 1 to 4 parts by weight of diamyl phenol blended into to 70 parts by weight of mineral oil.
2. A lubricating and conditioning composition comprising essentially of a mixture of 9 parts by weight of the primary ester of phosphoric acid with n-decanol, 20 parts by weight of the diethanolamino-ethyl ester of lauric acid, 2.5 parts by weight of triethanolamine and 2.5 parts by weight of diamyl phenol blended into parts by weight of mineral oil.
GEORGE W.-SEYMOUR. MARSHALL DUKE.
REFERENCES CITED The following references are of record in the file of this patent:
UIiI'I'ED STATES PATENTS Number Name Date 1,914,331 Nusslein June 13, 1933' 2,079,803 Holtzclaw May 11. 1937 2,205,042 Lenker et al June 18, 1940 2,278,747 Swezey et al. Apr. 11, 1942 2,385,423 Seymour et al. Sept. 25, 1945 2,479,644" Seymour et a1. Aug. 23, 1949

Claims (1)

1. A LUBRICATING AND CONDITIONING COMPOSITION CONSISTING ESSENTIALLY OF A MIXTURE OF 5 TO 15 PARTS BY WEIGHT OF THE PRIMARY ESTER OF PHOSPHORIC ACID WITH N-DECANOL, 10 TO 30 PARTS BY WEIGHT OF THE DIETHANOLAMINO-ETHYL ESTER OF LAURIC ACID, 1 TO 4 PARTS BY WEIGHT OF TRIETHANOLAMINE AND 1 TO 4 PARTS BY WEIGHT OF DIAMYL PHENOL BLENDED INTO 50 TO 70 PARTS BY WEIGHT OF MINERL OIL.
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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2676924A (en) * 1952-06-04 1954-04-27 Celanese Corp Textile lubricant
US2727860A (en) * 1952-03-07 1955-12-20 Celanese Corp Textile lubricants
US2730498A (en) * 1952-01-09 1956-01-10 Celanese Corp Textile lubricants
US2807864A (en) * 1954-06-24 1957-10-01 Eastman Kodak Co Composition and process for treating yarn
US2831813A (en) * 1954-06-22 1958-04-22 Exxon Research Engineering Co Complex ester synthetic lubricant
US2956949A (en) * 1955-10-19 1960-10-18 Eastman Kodak Co Fiber treating compositions
US3297570A (en) * 1964-05-28 1967-01-10 Eastman Kodak Co Yarn treating compositions
US3308826A (en) * 1961-03-09 1967-03-14 Celanese Corp Sanitary napkins
US3357919A (en) * 1964-09-18 1967-12-12 Celanese Corp Finish compositions for textile materials

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1914331A (en) * 1929-12-18 1933-06-13 Ig Farbenindustrie Ag Treatment of textile materials with aqueous liquids
US2079803A (en) * 1934-05-11 1937-05-11 Standard Oil Dev Co Soluble oil
US2205042A (en) * 1937-10-26 1940-06-18 Du Pont Softening of textile materials and compositions therefor
US2278747A (en) * 1940-05-23 1942-04-07 Du Pont Chemical composition
US2385423A (en) * 1942-10-03 1945-09-25 Celanese Corp Treatment of textile materials
US2479644A (en) * 1947-03-29 1949-08-23 Celanese Corp Conditioning agent

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1914331A (en) * 1929-12-18 1933-06-13 Ig Farbenindustrie Ag Treatment of textile materials with aqueous liquids
US2079803A (en) * 1934-05-11 1937-05-11 Standard Oil Dev Co Soluble oil
US2205042A (en) * 1937-10-26 1940-06-18 Du Pont Softening of textile materials and compositions therefor
US2278747A (en) * 1940-05-23 1942-04-07 Du Pont Chemical composition
US2385423A (en) * 1942-10-03 1945-09-25 Celanese Corp Treatment of textile materials
US2479644A (en) * 1947-03-29 1949-08-23 Celanese Corp Conditioning agent

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2730498A (en) * 1952-01-09 1956-01-10 Celanese Corp Textile lubricants
US2727860A (en) * 1952-03-07 1955-12-20 Celanese Corp Textile lubricants
US2676924A (en) * 1952-06-04 1954-04-27 Celanese Corp Textile lubricant
US2831813A (en) * 1954-06-22 1958-04-22 Exxon Research Engineering Co Complex ester synthetic lubricant
US2807864A (en) * 1954-06-24 1957-10-01 Eastman Kodak Co Composition and process for treating yarn
US2956949A (en) * 1955-10-19 1960-10-18 Eastman Kodak Co Fiber treating compositions
US3308826A (en) * 1961-03-09 1967-03-14 Celanese Corp Sanitary napkins
US3297570A (en) * 1964-05-28 1967-01-10 Eastman Kodak Co Yarn treating compositions
US3357919A (en) * 1964-09-18 1967-12-12 Celanese Corp Finish compositions for textile materials

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