US2103497A - Artificial textile material and method of preparing the same - Google Patents

Artificial textile material and method of preparing the same Download PDF

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Publication number
US2103497A
US2103497A US84479A US8447936A US2103497A US 2103497 A US2103497 A US 2103497A US 84479 A US84479 A US 84479A US 8447936 A US8447936 A US 8447936A US 2103497 A US2103497 A US 2103497A
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para
cellulose
yarns
filaments
oils
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US84479A
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Schneider George
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Celanese Corp
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Celanese Corp
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Priority claimed from US723844A external-priority patent/US2067951A/en
Priority to GB12855/35A priority Critical patent/GB454666A/en
Application filed by Celanese Corp filed Critical Celanese Corp
Priority to US84479A priority patent/US2103497A/en
Application granted granted Critical
Publication of US2103497A publication Critical patent/US2103497A/en
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating 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 oxygen
    • D06M13/224—Esters of carboxylic acids; Esters of carbonic acid
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F2/00—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof
    • D01F2/24—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from cellulose derivatives
    • D01F2/28—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from cellulose derivatives from organic cellulose esters or ethers, e.g. cellulose acetate
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating 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 oxygen
    • D06M13/152—Treating 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 oxygen having a hydroxy group bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/022—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms containing at least two hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/284—Esters of aromatic monocarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/285—Esters of aromatic polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/402—Castor oils
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/46—Textile oils

Definitions

  • This invention relates to the preparation or treatment of artificial materials particularly textile materials, such as yarns or filaments made of organic derivatives of cellulose, whereby the Same are rendered more amenable to textile operations or have other improved properties.
  • An object of my invention is to prepare or treat textile materials, particularly yarns or filaments containing cellulose acetate or other organic derivatives ofcellulose by the employment of oils or fatty acids in conjunction with a parabenzene derivative, whereby the yarns or fila ments are rendered more pliable and can there- I and gummy bodies.
  • I employ the animal or vegetable oils or the fatty. acids derived therefrom in conjunction with para derivatives of phenol in the preparation or' treatment of artificial materials particularly those contain- I-llowever, when ing cellulose acetate or other organic derivatives of cellulose.
  • the animal or vegetable oils employed may be any suitable one such as olive oil, teaseed oil, peanut oil, castor oil, cocoanut oil, neatsfoot oil and in general the glycerides of the higher fatty acids such as oleic acid, palmitic acid or stearic acid.
  • One of such oils or a mixture of two or more such oils may be employed.
  • the fatty acids themselves may be employed.
  • These oils may be used alone or in conjunction with mineral lubricating oils and sulphonated oils as well asin conjunction with bodies having a beneficial effect such as diethylene glycol, glycerine, etc.
  • phenol Any suitable para derivative of, phenol may be ,employed, for example hydroquinone, methyl ester of paraoxy benzoic acid, propyl ester of paraoxy benzoic acid and other like derivatives of benzol.
  • the para derivatives of benzene may have the graphic formula where R. is OH or COOR wherein R is an alkyl group such as methyl, ethyl, butyl and propyl radicals.
  • the amount of para derivative of phenol employed may be any suitable. one being usually small and on the order of 0.2 to 4.% of the weight of the oils or fatty acids employed.
  • the vegetable or animal oils or the fatty acids in admixture with the para derivative of benzol may be added to the spinning dope or solution from which the yarns, filaments, artificial bristles or straw and the like are formed, and such solution may then be extruded through orifices to an evaporative atmosphere as in dry spinning or into the precipitating bath as in wet spinning, or thin foils or thinfilms may be made from such solutions by casting the same on to a film casting wheel or by other known methods.
  • the mixture of oils or fatty acids and the para derivative of phenol may be applied to the yarns, filaments, fabrics, films or foils after their formation. They may be applied either alone or in admixture with other materials as a lubricant or finish.
  • the lubricant or finish may also contain softening agents such as the polyhydric alcohols, their derivatives and substitution products, the examples of which are diethylene glycol and glycerine.
  • the textile materials or other artificial materials to be prepared or treated in accordance with this invention preferably contain organic derivatives of cellulose which may be organic esters of cellulose or cellulose ethers.
  • organic esters of cellulose are cellulose acetate, cellulose formate, cellulose propionate and cellulose butyrate, while examples of such cellulose ethers are ethyl cellulose, methyl cellulose and benzyl cellulose.
  • Example A finish is prepared as follows:
  • para derivative of phenol lpart by weight the para derivative of phenol may be the methyl ester of parahydroxy benzoic acid, or the propyl ester of parahydroxy benzoic acid.
  • the above mixture is applied to a yarn consisting wholly of acetone soluble cellulose acetate filaments, by causing such yarn. to pass over wicks, rollers or other furnishing devices for applying such mixture, in their transit from the dry spinning machine in which they are formed to a winding device.
  • the amount of finish applied is from 1 to 6% on the weight of the yarn.
  • the para derivatives of phenol greatly reduce the tendency of the olive oil to polymerize upon ageing and inhibits oxidation. Moreover while cellulose acetate yarns or fabrics treated with olive oil alone after a period of time tend to deluster more readily when treated with hot aqueous fluids the presence of the para derivative of phenol greatly reduces this tendency of delustering. Moreover, the above type of finish has the property of maintaining a finish, over the entire yarn or fabric, of the same consistency. Thus when the material is subjected to dyeing, washing or other hot aqueous liquid treatments there ,is no streakiness produced as in the case where the lubricant finish tends to change its chemical composition in one place more than in another.
  • Process of improving the properties of filaments or yarns containing cellulose acetate comprising applying thereto a finish containing a fatty material selected from the group consisting of higher fatty acids and their glycerides and an alkyl ester of a para hydroxy benzoic acid.
  • meme? 1'8 Artificial material of'cellulose acetate containing a fatty material selected from the group consisting of higher fatty acids and their glyc-' erides and the propyl ester of a para lmdroxy benmic acid.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Description

ARMMCHMA inhuman or raarnra 'r s George Schneider, Monte @elanese Gorporation of tion. of Delaware N. it, assignor-to *l -w a cora- No mrag. flrlginal application y ll, 19%,
Serial No. 723,8M. Divided and this applicatilon .l'e 310', 1936,5031 No. $4.479
18 Claims.
This invention relates to the preparation or treatment of artificial materials particularly textile materials, such as yarns or filaments made of organic derivatives of cellulose, whereby the Same are rendered more amenable to textile operations or have other improved properties.
-s application is a division of my application s. No. 723,844 filed May 4, 1934.
An object of my invention is to prepare or treat textile materials, particularly yarns or filaments containing cellulose acetate or other organic derivatives ofcellulose by the employment of oils or fatty acids in conjunction with a parabenzene derivative, whereby the yarns or fila ments are rendered more pliable and can there- I and gummy bodies.
I have found that if para-benzene derivatives 7 applied, remain soft and not sticky when exposed to the air for'long periods of time. Moreover the presence of these para-benzene derivatives greatly retard the development in such oils of free acidity, prevent oxidation and largely overcome the tendency of such oils upon ageing to render cellulose acetate yarns less resistant to the delustering action of hot aqueous liquids. All phenol derivatives have some preservative power in oils. I have found, however, that outstanding in eflectiveness in this respect, are the para derivatives of phenol such as hydroquinone.
In accordance with my invention I employ the animal or vegetable oils or the fatty. acids derived therefrom in conjunction with para derivatives of phenol in the preparation or' treatment of artificial materials particularly those contain- I-llowever, when ing cellulose acetate or other organic derivatives of cellulose.
The animal or vegetable oils employed may be any suitable one such as olive oil, teaseed oil, peanut oil, castor oil, cocoanut oil, neatsfoot oil and in general the glycerides of the higher fatty acids such as oleic acid, palmitic acid or stearic acid. One of such oils or a mixture of two or more such oils may be employed. If desired the fatty acids themselves may be employed. These oils may be used alone or in conjunction with mineral lubricating oils and sulphonated oils as well asin conjunction with bodies having a beneficial effect such as diethylene glycol, glycerine, etc.
In order to prevent such oils and fatty acids from oxidizing, hydrolyzing, polymerizing or otherwise becoming sticky and thus imparting harshness to the textile material, I add a para derivative of phenol. Any suitable para derivative of, phenol may be ,employed, for example hydroquinone, methyl ester of paraoxy benzoic acid, propyl ester of paraoxy benzoic acid and other like derivatives of benzol. The para derivatives of benzene may have the graphic formula where R. is OH or COOR wherein R is an alkyl group such as methyl, ethyl, butyl and propyl radicals.
The amount of para derivative of phenol employed may be any suitable. one being usually small and on the order of 0.2 to 4.% of the weight of the oils or fatty acids employed.
In one form of myinvention, the vegetable or animal oils or the fatty acids in admixture with the para derivative of benzol may be added to the spinning dope or solution from which the yarns, filaments, artificial bristles or straw and the like are formed, and such solution may then be extruded through orifices to an evaporative atmosphere as in dry spinning or into the precipitating bath as in wet spinning, or thin foils or thinfilms may be made from such solutions by casting the same on to a film casting wheel or by other known methods.
In another form of my invention the mixture of oils or fatty acids and the para derivative of phenol may be applied to the yarns, filaments, fabrics, films or foils after their formation. They may be applied either alone or in admixture with other materials as a lubricant or finish. Thus the lubricant or finish may also contain softening agents such as the polyhydric alcohols, their derivatives and substitution products, the examples of which are diethylene glycol and glycerine.
The textile materials or other artificial materials to be prepared or treated in accordance with this invention preferably contain organic derivatives of cellulose which may be organic esters of cellulose or cellulose ethers. Examples of such organic esters of cellulose are cellulose acetate, cellulose formate, cellulose propionate and cellulose butyrate, while examples of such cellulose ethers are ethyl cellulose, methyl cellulose and benzyl cellulose.
Yarns, artificial straw or filaments when prepared or treated in accordance with this invention have great pliability due to the presence of the animal or vegetable oils or the free fatty acids, as shown by the fact'that such yarns may be readily knitted into fabric containing many stitches per unit length and artificial bristles, horsehair and straw may be knotted quite tightly .and bent quite severely without breaking. Moreover when such yarns are exposed to the air for long periods of time, because of the presence of the para derivative of phenol, they retain their softness and pliability and can be readily knitted. In order to further illustrate my invention but without being limited thereto the following specific example is given.
Example A finish is prepared as follows:
Para derivative of phenol lpart by weight In the above mixture, the para derivative of phenol may be the methyl ester of parahydroxy benzoic acid, or the propyl ester of parahydroxy benzoic acid. The above mixture is applied to a yarn consisting wholly of acetone soluble cellulose acetate filaments, by causing such yarn. to pass over wicks, rollers or other furnishing devices for applying such mixture, in their transit from the dry spinning machine in which they are formed to a winding device. The amount of finish applied is from 1 to 6% on the weight of the yarn.
The para derivatives of phenol greatly reduce the tendency of the olive oil to polymerize upon ageing and inhibits oxidation. Moreover while cellulose acetate yarns or fabrics treated with olive oil alone after a period of time tend to deluster more readily when treated with hot aqueous fluids the presence of the para derivative of phenol greatly reduces this tendency of delustering. Moreover, the above type of finish has the property of maintaining a finish, over the entire yarn or fabric, of the same consistency. Thus when the material is subjected to dyeing, washing or other hot aqueous liquid treatments there ,is no streakiness produced as in the case where the lubricant finish tends to change its chemical composition in one place more than in another.
It is to be understood that the foregoing de-' scription is given merely by way of illustration and that many variations may be made therein,
without departing from the spirit of myinvention.
Having described my invention, what I desire to secure by Letters Patent is:
1. Process of improving the properties of filaments or yarns containing organic derivatives of cellulose comprising applying thereto a finish containing a fatty material selected from the group consisting of higher fatty acids and their glycerides and an alkyl ester of a para hydroxy benzoic acid. l
2. Process of improving the properties of filaments or yarns containing cellulose acetate comprising applying thereto a finish containing a fatty material selected from the group consisting of higher fatty acids and their glycerides and an alkyl ester of a para hydroxy benzoic acid.
3. Process of improving the properties of filaments or yarns containing organic derivatives of cellulose comprising applying thereto a finish containing a glyceride of a higher fatty acid and an alkyl ester of para hydroxy benzoic acid.
4. Process of improving the properties of filaments or yarns containing cellulose acetate comprising applying thereto a finish containing a glyceride of a higher fatty acid and an alkyl ester of para hydroxy benzoic acid.
5. Process of improving the properties of filaments or yarns of cellulose acetate comprising apments or yarns of cellulose acetate comprising applying thereto a finish containing olive oil and the propyl ester of para hydroxy benzoic acid.
, 8. Artificial material of organic derivatives of cellulose containing a fatty material selected from the group consisting of higher fatty acids and their glycerides and an alkyl ester of a para hydroxy benzoic acid. I
9. Artificial material of cellulose acetate containing a fatty material selected from the group consisting of higher fatty acids and their glycerides and an alkyl ester of a para hydroxy benzoic acid.
10. Artificial yarns and filaments of organic derivatives of cellulose containing a glyceride of a higher fatty acid and an alkyl ester of para hydroxy benzoic acid.
11. Artificial yarns and filaments of cellulose acetate containing a glyceride of a higher fatty acid and an alkyl ester of para hydroxy benzoic acid.
12. Artificial yarns and filaments of cellulose acetate containing a vegetable oil and an alkyl ester of para hydroxy benzoic acid.
13. Artificial yarns and filaments of cellulose ments or yarns containing cellulose acetate comprising applying thereto a finish containing a erldes and the methyl ester of a. para hydrom benzoic acid.
meme? 1'8. Artificial material of'cellulose acetate containing a fatty material selected from the group consisting of higher fatty acids and their glyc-' erides and the propyl ester of a para lmdroxy benmic acid.
V l GEORGE ecmmmm
US84479A 1934-05-04 1936-06-10 Artificial textile material and method of preparing the same Expired - Lifetime US2103497A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB12855/35A GB454666A (en) 1934-05-04 1935-04-30 Improvements in dressing textile materials
US84479A US2103497A (en) 1934-05-04 1936-06-10 Artificial textile material and method of preparing the same

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US723844A US2067951A (en) 1933-07-03 1934-05-04 Artificial textile materials and method of preparing the same
US84479A US2103497A (en) 1934-05-04 1936-06-10 Artificial textile material and method of preparing the same

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2444307A (en) * 1945-04-27 1948-06-29 Frederic H Penn Emulsified food fats of improved keeping qualities
US3247018A (en) * 1961-10-25 1966-04-19 Bayer Ag Process for treating textile materials
US3296020A (en) * 1964-08-27 1967-01-03 Bibb Mfg Co Process for producing antistatic characteristic in nylon fibers

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2444307A (en) * 1945-04-27 1948-06-29 Frederic H Penn Emulsified food fats of improved keeping qualities
US3247018A (en) * 1961-10-25 1966-04-19 Bayer Ag Process for treating textile materials
US3296020A (en) * 1964-08-27 1967-01-03 Bibb Mfg Co Process for producing antistatic characteristic in nylon fibers

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Publication number Publication date
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