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US2976186A - Treated textile fiber - Google Patents

Treated textile fiber Download PDF

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Publication number
US2976186A
US2976186A US699165A US69916557A US2976186A US 2976186 A US2976186 A US 2976186A US 699165 A US699165 A US 699165A US 69916557 A US69916557 A US 69916557A US 2976186 A US2976186 A US 2976186A
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US
United States
Prior art keywords
fibers
weight
parts
lauryl
textile
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Expired - Lifetime
Application number
US699165A
Inventor
Howard A Thompson
Raymond E Donaldson
White Charles Clayton
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eastman Kodak Co
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Eastman Kodak Co
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Publication date
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Priority to US699165A priority Critical patent/US2976186A/en
Application granted granted Critical
Publication of US2976186A publication Critical patent/US2976186A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M7/00—Treating 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
    • 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
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/40—Reduced friction resistance, lubricant properties; Sizing compositions
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S260/00—Chemistry of carbon compounds
    • Y10S260/15—Antistatic agents not otherwise provided for
    • Y10S260/16—Antistatic agents containing a metal, silicon, boron or phosphorus
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913—Rod, strand, filament or fiber
    • Y10T428/2933—Coated or with bond, impregnation or core
    • Y10T428/2964—Artificial fiber or filament
    • Y10T428/2965—Cellulosic
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913—Rod, strand, filament or fiber
    • Y10T428/2933—Coated or with bond, impregnation or core
    • Y10T428/2964—Artificial fiber or filament
    • Y10T428/2967—Synthetic resin or polymer
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913—Rod, strand, filament or fiber
    • Y10T428/2933—Coated or with bond, impregnation or core
    • Y10T428/2964—Artificial fiber or filament
    • Y10T428/2967—Synthetic resin or polymer
    • Y10T428/2969—Polyamide, polyimide or polyester

Definitions

  • This invention relates to compositions for the treatment of artificial fibers, filaments and yarns, to render them more amenable to textile operations such as drafting, relaxing, spinning, twisting, winding, reeling, carding, combing, warping, weaving, knitting and the like.
  • the fibers which may advantageously be treated with our compositions include both those composed of cellulose esters, such as cellulose acetate, cellulose triacetate, cellulose acetate-butyrate, and cellulose acetate-propionate, and those composed of synthetic polymers, such, for instance, as polyesters and acrylic polymers.
  • cellulose esters such as cellulose acetate, cellulose triacetate, cellulose acetate-butyrate, and cellulose acetate-propionate
  • synthetic polymers such, for instance, as polyesters and acrylic polymers.
  • agents which have been indicated in the art as suitable for W001, viscose, or cellulose acetate do not necessarily produce the desired efiects on hydrophobic non-cellulosic fibers.
  • the antistatic agent must be compatible with lubricants, sizes and other agents applied to fibers in the textile mill. It must allow proper running tensions of filaments during drawing and twisting operations. It must be noncorrosive to the equipment in which the fiber will be worked, and it must be non-toxic and have no injurious dermatological effects upon the worker or upon the ultimate wearer.
  • R is an alkyl radical of from 1 to 17 carbon atoms
  • R is an aliphatic radical selected from the group consisting of lauryl and oleyl
  • R" is a radical selected from the group consisting of lauryl, oleyl and hydrogen.
  • They are formed when 2-alkyl-4,4-dimethyl-Z-oxazolines are added to lauryl or oleyl partial esters of phosphoric acid.
  • the partial esters of phosphoric acid are mixtures of the monoand di-esters.
  • the lubricating compositions containing these oxazoline salts preferably "ice also contain mineral oil and a long-chain aliphatic alcohol or alicyclic alcohol.
  • compositions may, if desired, be applied to the filaments as the filaments emerge from the spinning cabinet in which they are formed.
  • Cellulose ester fibers treated with the lubricants of our invention have especially high resistance to abrasion when sized with materials such as gelatin and copolymers of maleic anhydride and styrene, which are commonly used in the trade.
  • Both cellulose ester fibers and synthetic polymeric fibers may be satisfactorily lubricated and conditioned for spinning operations by the application thereto of a single application of our novel lubricating and conditioning compositions, Our compositions are thoroughly dispersed over the fibers in application thereto, and the fibers thus treated are completely antistatic, so that a superior degree of lubrication and conditioning is achieved.
  • Our novel compositions preferably comprise from 10 to 20 parts by weight of the lauryl or oleyl partial ester of phosphoric acid combined with from 2 to 15 parts by weight of a 2-alkyl-4,4-dimethyl-2-oxazoline, 5 to 15 parts by weight of a long-chain fatty alcohol or alicyclic alcohol, and from 40 to 70 parts by weight of mineral oil having a viscosity of from 45 to 135 (Saybolt Universal seconds of F.). Other components may also be present.
  • the components are preferably combined by adding the lauryl or oleyl partial ester of phosphoric acid to the mineral oil with stirring, followed by the addition of the 2-alkyl-4,4-dimethyl-2-oxazoline and the addition of the long-chain fatty alcohol or alicyclic alcohol. After the components are mixed, gentle agitation is continued until a smooth homogeneous blend is obtained.
  • Example 1 One-hundred-fifty denier, 38 filament bright cellulose acetate yarn was lubricated and conditioned by applying to it by means of an applicator roll, as the filaments left the spinning cabinet, 2.5%, on the weight of the dry yarn, of the following composition:
  • Percent Mineral oil 45 Lauryl partial esters of phosphoric acid ...E. 25 2-alkyl-4,4-dimethyl-Z-oxazoline 20 Lauryl alcohol 10 applied as a 25% emulsion in water. The yarn thus lubricated performed satisfactorily in all twisting, winding, sizing and weaving operations.
  • Example 2 An acrylic yarn was lubricated with 0.4% of the oil composition described in Example 1 by passing over an applicator roll wet with the lubricant composition as the filaments emerged from the spinning cabinet. The yarn was drafted, crimped and cut into suitable lengths.
  • This cut staple was carded and spun into yarn, and was found to process well in all operations.
  • Example 3 --A polyester yarn was lubricated with 0.4% of the oil composition described in Example 1 by passing over an applicator roll wet with the lubricant composition as the filaments emerged from the spinning cabinet. The yarn was drafted, crimped and cut into suitable lengths. This cut staple was carded and spun into yarn, and was found to process Well in all operations.
  • the lubricant was applied by means of an applicator roll as the filaments left the spinning cabinet; however, the composition may equally well be applied at other stages of processing and in other operations such as twisting, winding, and reeling, or they may be applied to cut staple fibers during any of the processes to which such fibers are subjected. Moreover, although we have indicated that the lubricant may be applied by passing the filaments over a roll, other devices which serve to deposit oil on filaments or fibers, such as wicks, spray or both, may be used.
  • lubricant compositions we may use another non-aromatic alcohol of at least six carbon atoms, such as, for example, oleyl, cyclohexyl myristyl, cetyl, stearyl, linolyl or n'cinolyl alcohol or mixtures of these, in place of the lauryl alcohol added as the fourth component of the composition.
  • another non-aromatic alcohol of at least six carbon atoms such as, for example, oleyl, cyclohexyl myristyl, cetyl, stearyl, linolyl or n'cinolyl alcohol or mixtures of these, in place of the lauryl alcohol added as the fourth component of the composition.
  • a textile fiber selected from the group consisting of cellulose ester fibers and hydrophobic synthetic polymer fibers, carrying a textile lubricant composition comprising from 40 to 70 parts by weight of mineral oil, from 5 to 15 parts by weight of a non-aromatic alcohol of from 6 to 18 carbon atoms, and from 12 to 35 parts by Weight of a compound having the structural formula CH3 OR in which R is an alkyl radical of from 1 to 17 carbon atoms, R is an aliphatic radical selected from the group consisting of lauryl and oleyl, and R" is a radical selected from the group consisting of lauryl, oleyl and hydrogen.
  • a cellulose ester textile fiber carrying a textile lubricant composition comprising from 40 to 70 parts by weight of mineral oil, from to 15 parts by weight of a non-aromatic alcohol of from 6 to 18 carbon atoms, and from 12 to 35 parts by weight of a compound having the structural formula in which R is an alkyl radical of from 1 to 17 carbon atoms, R is an aliphatic radical selected from the group consisting of lauryl and oleyl, and R" is a radical selected from the group consisting of lauryl, oleyl and hydrogen.
  • a hydrophobic synthetic polymer textile fiber carrying a textile lubricant composition comprising from 40 to parts by weight of mineral oil, from 5 to 15 parts by weight of a non-aromatic alcohol of from 6 to 18 carbon atoms, and from 12 to 35 parts by weight of a compound having the structural formula in which R is an alkyl radical of from 1 to 17 carbon atoms, R is an aliphatic radical selected from the group consisting of lauryl and oleyl, and R" is a radical selected from the group consisting of lauryl, oleyl and hydrogen.

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

Description

TREATED TEXTILE FIBER Howard A. Thompson, Raymond E. Donaldson, and Charles Clayton White, Kingsport, Tenn., assignors to Eastman Kodak Company, Rochester, N.Y., a corporation of New Jersey No Drawing. Filed Nov. 27, 1957, Ser. No. 699,165 3 Claims. (Cl. 117-1395) This invention relates to compositions for the treatment of artificial fibers, filaments and yarns, to render them more amenable to textile operations such as drafting, relaxing, spinning, twisting, winding, reeling, carding, combing, warping, weaving, knitting and the like. The fibers which may advantageously be treated with our compositions include both those composed of cellulose esters, such as cellulose acetate, cellulose triacetate, cellulose acetate-butyrate, and cellulose acetate-propionate, and those composed of synthetic polymers, such, for instance, as polyesters and acrylic polymers.
As is well known in the textile industry, it is necessary to treat yarns and fibers with lubricating compositions, in order to reduce the tendency toward breakage of the individual filaments when they are subjected to various mechanical stresses and strains and to facilitate handling in textile operations. Lubricating compositions freatent O quently contain an antistatic agent, to prevent electrical attraction of the filaments to each other and to the equipment on which they are being handled. Although the general idea of treating textile fibers with antistatic agents is old, the problem of selecting a proper agent is by no means a simple one. In the first place, the nature of the fiber to be treated must be taken into account. Thus, agents which have been indicated in the art as suitable for W001, viscose, or cellulose acetate do not necessarily produce the desired efiects on hydrophobic non-cellulosic fibers. Further, the antistatic agent must be compatible with lubricants, sizes and other agents applied to fibers in the textile mill. It must allow proper running tensions of filaments during drawing and twisting operations. It must be noncorrosive to the equipment in which the fiber will be worked, and it must be non-toxic and have no injurious dermatological effects upon the worker or upon the ultimate wearer.
We have found that the 2-alkyl-4,4-dimethyl-2-oxazoline salts of lauryl or oleyl phosphoric acid partial esters, where the alkyl group may contain from 1 to 17 carbon atoms, are excellent anti-static agents for use in lubricating compositions for both cellulose .ester yarns and hydrophobic synthetic polymer yarns. These compounds are free-flowing liquids. They have the following structural formula:
in which R is an alkyl radical of from 1 to 17 carbon atoms, R is an aliphatic radical selected from the group consisting of lauryl and oleyl, and R" is a radical selected from the group consisting of lauryl, oleyl and hydrogen. They are formed when 2-alkyl-4,4-dimethyl-Z-oxazolines are added to lauryl or oleyl partial esters of phosphoric acid. Usually the partial esters of phosphoric acid are mixtures of the monoand di-esters. The lubricating compositions containing these oxazoline salts preferably "ice also contain mineral oil and a long-chain aliphatic alcohol or alicyclic alcohol.
Our novel compositions may, if desired, be applied to the filaments as the filaments emerge from the spinning cabinet in which they are formed. The compositions-are non-tacky on heated processing rolls, and are color-stable when processed on heated rolls. They do not undergo chemical reaction with the fibers or the spinning solvent to form colored products which mar the desired shade of the fibers. They may be used on both continuous filament and cut staple fibers.
Cellulose ester fibers treated with the lubricants of our invention have especially high resistance to abrasion when sized with materials such as gelatin and copolymers of maleic anhydride and styrene, which are commonly used in the trade.
Both cellulose ester fibers and synthetic polymeric fibers may be satisfactorily lubricated and conditioned for spinning operations by the application thereto of a single application of our novel lubricating and conditioning compositions, Our compositions are thoroughly dispersed over the fibers in application thereto, and the fibers thus treated are completely antistatic, so that a superior degree of lubrication and conditioning is achieved.
Our novel compositions preferably comprise from 10 to 20 parts by weight of the lauryl or oleyl partial ester of phosphoric acid combined with from 2 to 15 parts by weight of a 2-alkyl-4,4-dimethyl-2-oxazoline, 5 to 15 parts by weight of a long-chain fatty alcohol or alicyclic alcohol, and from 40 to 70 parts by weight of mineral oil having a viscosity of from 45 to 135 (Saybolt Universal seconds of F.). Other components may also be present.
In forming said lubricating and conditioning compositions, the components are preferably combined by adding the lauryl or oleyl partial ester of phosphoric acid to the mineral oil with stirring, followed by the addition of the 2-alkyl-4,4-dimethyl-2-oxazoline and the addition of the long-chain fatty alcohol or alicyclic alcohol. After the components are mixed, gentle agitation is continued until a smooth homogeneous blend is obtained.
As illustrating but not limiting our invention, we give the following examples. 7
Example 1.-One-hundred-fifty denier, 38 filament bright cellulose acetate yarn was lubricated and conditioned by applying to it by means of an applicator roll, as the filaments left the spinning cabinet, 2.5%, on the weight of the dry yarn, of the following composition:
Percent Mineral oil 45 Lauryl partial esters of phosphoric acid ...E. 25 2-alkyl-4,4-dimethyl-Z-oxazoline 20 Lauryl alcohol 10 applied as a 25% emulsion in water. The yarn thus lubricated performed satisfactorily in all twisting, winding, sizing and weaving operations.
Example 2.-An acrylic yarn Was lubricated with 0.4% of the oil composition described in Example 1 by passing over an applicator roll wet with the lubricant composition as the filaments emerged from the spinning cabinet. The yarn was drafted, crimped and cut into suitable lengths.
This cut staple was carded and spun into yarn, and was found to process well in all operations.
Example 3.--A polyester yarn was lubricated with 0.4% of the oil composition described in Example 1 by passing over an applicator roll wet with the lubricant composition as the filaments emerged from the spinning cabinet. The yarn was drafted, crimped and cut into suitable lengths. This cut staple was carded and spun into yarn, and was found to process Well in all operations.
Although in the above examples we have indicated certain percentages of lubricant composition applied to fibers for use as out staple 'fibers or continuous filament yarns, our invention is not restricted to these percentages.
'In the above examples we have stated that the lubricant was applied by means of an applicator roll as the filaments left the spinning cabinet; however, the composition may equally well be applied at other stages of processing and in other operations such as twisting, winding, and reeling, or they may be applied to cut staple fibers during any of the processes to which such fibers are subjected. Moreover, although we have indicated that the lubricant may be applied by passing the filaments over a roll, other devices which serve to deposit oil on filaments or fibers, such as wicks, spray or both, may be used.
In formulating our lubricant compositions, we may use another non-aromatic alcohol of at least six carbon atoms, such as, for example, oleyl, cyclohexyl myristyl, cetyl, stearyl, linolyl or n'cinolyl alcohol or mixtures of these, in place of the lauryl alcohol added as the fourth component of the composition.
What we claim as our invention and desire to be secured by Letters Patent of the United States is:
1. A textile fiber selected from the group consisting of cellulose ester fibers and hydrophobic synthetic polymer fibers, carrying a textile lubricant composition comprising from 40 to 70 parts by weight of mineral oil, from 5 to 15 parts by weight of a non-aromatic alcohol of from 6 to 18 carbon atoms, and from 12 to 35 parts by Weight of a compound having the structural formula CH3 OR in which R is an alkyl radical of from 1 to 17 carbon atoms, R is an aliphatic radical selected from the group consisting of lauryl and oleyl, and R" is a radical selected from the group consisting of lauryl, oleyl and hydrogen.
2. A cellulose ester textile fiber carrying a textile lubricant composition comprising from 40 to 70 parts by weight of mineral oil, from to 15 parts by weight of a non-aromatic alcohol of from 6 to 18 carbon atoms, and from 12 to 35 parts by weight of a compound having the structural formula in which R is an alkyl radical of from 1 to 17 carbon atoms, R is an aliphatic radical selected from the group consisting of lauryl and oleyl, and R" is a radical selected from the group consisting of lauryl, oleyl and hydrogen.
3. A hydrophobic synthetic polymer textile fiber carrying a textile lubricant composition comprising from 40 to parts by weight of mineral oil, from 5 to 15 parts by weight of a non-aromatic alcohol of from 6 to 18 carbon atoms, and from 12 to 35 parts by weight of a compound having the structural formula in which R is an alkyl radical of from 1 to 17 carbon atoms, R is an aliphatic radical selected from the group consisting of lauryl and oleyl, and R" is a radical selected from the group consisting of lauryl, oleyl and hydrogen.
References Cited in the file of this patent UNITED STATES PATENTS 2,274,617 Remy Feb. 24, 1942 2,442,582 Bishop June 1, 1948 2,622,045 Ester Dec. 16, 1952 2,676,122 McCarthy Apr. 20, 1954 2,727,860 Duke Dec. 20, 1955 2,730,464 Winsor Jan. 10, 1956 FOREIGN PATENTS 585,803 Great Britain Feb. 25, 1947

Claims (1)

1. A TEXTILE FIBER SELECTED FROM THE GROUP CONSISTING OF CELLULOSE ESTER FIBERS AND HYDROPHOBIC SYNTHETIC POLYMER FRIBERS, CARRYING A TEXTILE LIBRICANT COMPOSITION COMPRISING FROM 40 TO 70 PARTS BY WEIGHT OF MINERAL OIL, FROM 5 TO 15 PARTS BY WEIGHT OF NON-AROMATIC ALCOHOL OF FROM 6 TO 18 CARBON ATOMS, AND FROM 12 TO 35 PARTS BY WEIGHT OF A COMPOUND HAVING THE STRUCTURAL FORMULA
US699165A 1957-11-27 1957-11-27 Treated textile fiber Expired - Lifetime US2976186A (en)

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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3306850A (en) * 1964-12-17 1967-02-28 Du Pont Composition
US4496631A (en) * 1982-05-26 1985-01-29 Toray Industries, Inc. Acrylic fibers for producing carbon fibers
WO1986002369A1 (en) * 1984-10-09 1986-04-24 Interface Research Corporation Microbiocidal composition and method of preparation thereof
US4908209A (en) * 1983-08-16 1990-03-13 Interface, Inc. Biocidal delivery system of phosphate ester and method of preparation thereof
US4935232A (en) * 1983-08-16 1990-06-19 Interface Research Corporation Microbiocidal composition and method of preparation thereof
US4957948A (en) * 1988-05-05 1990-09-18 Interface, Inc. Biocidal protective coating for heat exchanger coils
US5024840A (en) * 1984-03-08 1991-06-18 Interface, Inc. Antimicrobial carpet and carpet tile
US5032310A (en) * 1983-08-16 1991-07-16 Interface, Inc. Microbiocidal cleansing and disinfecting formulations and preparation thereof
US5133933A (en) * 1983-08-16 1992-07-28 Interface Research Corporation Microbiocidal preservative
US5474739A (en) * 1978-02-04 1995-12-12 Interface, Inc. Microbiocidal composition
US5587407A (en) * 1988-09-09 1996-12-24 Interface, Inc. Biocidal polymeric coating for heat exchanger coils
US5635192A (en) * 1988-05-05 1997-06-03 Interface, Inc. Biocidal polymeric coating for heat exchanger coils
US20040131790A1 (en) * 2003-01-07 2004-07-08 Voegtli Leo Paul Method for using an ethoxylated alkyl phosphate ester additive as plugmaker processing aid
US20050202993A1 (en) * 2003-01-07 2005-09-15 Voegtli Leo P. Method for using an ethoxylated alkyl phosphate ester additive as a plugmaker processing aid

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2274617A (en) * 1938-04-27 1942-02-24 Theron P Remy Lubricating oil composition
GB585803A (en) * 1943-10-12 1947-02-25 Standard Oil Dev Co Improvements in or relating to addition agents for mineral lubricating oils
US2442582A (en) * 1946-08-10 1948-06-01 Tide Water Associated Oil Comp Oxazoline reaction products
US2622045A (en) * 1948-07-30 1952-12-16 Eastman Kodak Co Process of conditioning cellulose acetate yarn and product resulting therefrom
US2676122A (en) * 1951-01-09 1954-04-20 Du Pont Antistatic treatment of hydrophobic fiber
US2727860A (en) * 1952-03-07 1955-12-20 Celanese Corp Textile lubricants
US2730464A (en) * 1951-05-17 1956-01-10 Shell Dev Antistatic treatment of textile yarns

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2274617A (en) * 1938-04-27 1942-02-24 Theron P Remy Lubricating oil composition
GB585803A (en) * 1943-10-12 1947-02-25 Standard Oil Dev Co Improvements in or relating to addition agents for mineral lubricating oils
US2442582A (en) * 1946-08-10 1948-06-01 Tide Water Associated Oil Comp Oxazoline reaction products
US2622045A (en) * 1948-07-30 1952-12-16 Eastman Kodak Co Process of conditioning cellulose acetate yarn and product resulting therefrom
US2676122A (en) * 1951-01-09 1954-04-20 Du Pont Antistatic treatment of hydrophobic fiber
US2730464A (en) * 1951-05-17 1956-01-10 Shell Dev Antistatic treatment of textile yarns
US2727860A (en) * 1952-03-07 1955-12-20 Celanese Corp Textile lubricants

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3306850A (en) * 1964-12-17 1967-02-28 Du Pont Composition
US5474739A (en) * 1978-02-04 1995-12-12 Interface, Inc. Microbiocidal composition
US4496631A (en) * 1982-05-26 1985-01-29 Toray Industries, Inc. Acrylic fibers for producing carbon fibers
US5133933A (en) * 1983-08-16 1992-07-28 Interface Research Corporation Microbiocidal preservative
US4935232A (en) * 1983-08-16 1990-06-19 Interface Research Corporation Microbiocidal composition and method of preparation thereof
US5032310A (en) * 1983-08-16 1991-07-16 Interface, Inc. Microbiocidal cleansing and disinfecting formulations and preparation thereof
US4908209A (en) * 1983-08-16 1990-03-13 Interface, Inc. Biocidal delivery system of phosphate ester and method of preparation thereof
US5024840A (en) * 1984-03-08 1991-06-18 Interface, Inc. Antimicrobial carpet and carpet tile
WO1986002369A1 (en) * 1984-10-09 1986-04-24 Interface Research Corporation Microbiocidal composition and method of preparation thereof
US4957948A (en) * 1988-05-05 1990-09-18 Interface, Inc. Biocidal protective coating for heat exchanger coils
US5635192A (en) * 1988-05-05 1997-06-03 Interface, Inc. Biocidal polymeric coating for heat exchanger coils
US5639464A (en) * 1988-05-05 1997-06-17 Interface, Inc. Biocidal polymeric coating for heat exchanger coils
US5587407A (en) * 1988-09-09 1996-12-24 Interface, Inc. Biocidal polymeric coating for heat exchanger coils
US20040131790A1 (en) * 2003-01-07 2004-07-08 Voegtli Leo Paul Method for using an ethoxylated alkyl phosphate ester additive as plugmaker processing aid
US20050202179A1 (en) * 2003-01-07 2005-09-15 Voegtli Leo P. Method for using an ethoxylated alkyl phosphate ester additive as a plugmaker processing aid
US20050202993A1 (en) * 2003-01-07 2005-09-15 Voegtli Leo P. Method for using an ethoxylated alkyl phosphate ester additive as a plugmaker processing aid

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