US3212927A - Antistatic coating for synthetic fabrics - Google Patents

Antistatic coating for synthetic fabrics Download PDF

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US3212927A
US3212927A US400919A US40091964A US3212927A US 3212927 A US3212927 A US 3212927A US 400919 A US400919 A US 400919A US 40091964 A US40091964 A US 40091964A US 3212927 A US3212927 A US 3212927A
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Earl P Williams
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GAF Chemicals Corp
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
    • C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B20/00—Use of materials as fillers for mortars, concrete or artificial stone according to more than one of groups C04B14/00 - C04B18/00 and characterised by shape or grain distribution; Treatment of materials according to more than one of the groups C04B14/00 - C04B18/00 specially adapted to enhance their filling properties in mortars, concrete or artificial stone; Expanding or defibrillating materials
    • C04B20/10—Coating or impregnating
    • C04B20/1018—Coating or impregnating with organic materials
    • C04B20/1022—Non-macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B24/00—Use of organic materials as active ingredients for mortars, concrete or artificial stone, e.g. plasticisers
    • C04B24/12—Nitrogen containing compounds organic derivatives of hydrazine
    • C04B24/128—Heterocyclic nitrogen compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
    • C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
    • C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3415—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
    • C09K8/58—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids
    • C09K8/584—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids characterised by the use of specific surfactants
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
    • C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
    • C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
    • C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
    • C23F11/14—Nitrogen-containing compounds
    • C23F11/149—Heterocyclic compounds containing nitrogen as hetero atom
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
    • C23G1/00—Cleaning or pickling metallic material with solutions or molten salts
    • C23G1/02—Cleaning or pickling metallic material with solutions or molten salts with acid solutions
    • C23G1/04—Cleaning or pickling metallic material with solutions or molten salts with acid solutions using inhibitors
    • C23G1/06—Cleaning or pickling metallic material with solutions or molten salts with acid solutions using inhibitors organic inhibitors
    • C23G1/063—Cleaning or pickling metallic material with solutions or molten salts with acid solutions using inhibitors organic inhibitors heterocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25D—PROCESSES FOR THE ELECTROLYTIC OR ELECTROPHORETIC PRODUCTION OF COATINGS; ELECTROFORMING; APPARATUS THEREFOR
    • C25D3/00—Electroplating: Baths therefor
    • C25D3/02—Electroplating: Baths therefor from solutions
    • 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
    • D06M13/322—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 nitrogen
    • D06M13/402—Amides imides, sulfamic acids
    • D06M13/418—Cyclic amides, e.g. lactams; Amides of oxalic acid
    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B2103/00—Function or property of ingredients for mortars, concrete or artificial stone
    • C04B2103/0068—Ingredients with a function or property not provided for elsewhere in C04B2103/00
    • C04B2103/0074—Anti-static agents
    • 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
    • Y10S260/19—Non-high polymeric antistatic agents/n
    • 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 synthetic fabrics containing fatty acid esters of N-hydroxyalkyl-pynrolidones as antistatic coatings thereon.
  • N-hydroxyalkyl-pyrrolidone esters of saturated and unsaturated fatty acids of from 6 to 24 carbon atoms are excellent antistatic coatings for synthetic fabrics such as Acrilan, Dacron, nylon, Orion, etc., when employed in an antistatic coating amount varying from 0.5 to 2.5% by weight of the fabric.
  • the fabric may be dyed or undyed.
  • R and R represent either hydrogen, methyl or ethyl groups
  • R represents an alkylene radical containing from 1 to 6 carbon atoms
  • R represents a hydrocarbon residue of a fatty acid of 6 to 24 carbon atoms.
  • the esters are prepared by esterifying 1 mole of a fatty acid of 6 to 24 carbon atoms with 1 mole of an N-hydroxyalkyl-pyrrolidone by conventional means, preferably in the presence of an acid catalyst such as p-toluene sulfonic acid monohydrate.
  • the N-hydroxyalkyl-pyrrolidones are prepared in the well known manner by reacting at 250 C.
  • alkanolamine 1 to 6 carbon atoms with 1 mole of either butyrolactone, S-methyl butyrolactone, 4methyl butyrolactone, 4-ethyl butyrolactone, S-methyl butyrolacto-ne, S-ethyl butyrolactone or 3.3-dimethyl butyrolactone.
  • the alkanolamines utilized in such preparation consist of methanolamine, ethanolamine, 3-amino-propanol-l, 4-amino-butano1-1, S-aminopentano -1 or 6-arnino-hexanol-1.
  • the fatty acids of 6 to 24 carbon atoms that are esterified with the N-hydroxyalkyl-pynrolidones may be either saturated or unsaturated, aliphatic or aromatic.
  • the nature or character of the acid is immaterial so long as it is capable of esterification with a hydroxyl group.
  • Acids of this type include caproic, capry-llic, capric, lauric, myristic, palmitic, stearic, oleic, linoleic, behenic, tetracosanic, tall oil, hydrogenated tall oil, napthanic or abietic acid, phenoxyalkylcarboxylic, halogenated phenoxylalkylcarboxylic acids, o-p'hthalic acid, alkyl benzoic acids, such as dodecyl-benzoic acid, nonylbenzoic acid, octylbenzoic acid; acids from oxo alcohols and aldehydes, acids from oxidized petroleum fractions; acid mixtures from various natural plant and animal oils such as olive, palm, tallow, castor, peanut, coconut, soybean, cottonseed, ucuhuba, linseed; fish oils such as cod, herring, menhaden, etc.; neatsfoot, sperm, corn, butter,
  • esters prepared as above, are not only effective antistatic coating agents for synthetic fabrics, but are also useful in many diversified applications. For instance, they can be used as wetting, frothing or washing agents in the treatment and refining of textiles; for converting liquid or solid substances, which per se are insoluble in water, into creamy emulsions; for carbonizing; for dyeing; for the pasting of dyestuffs; for fulling; sizing; impregnating and bleaching treatments; as cleansing agents in hard Water; in tanning and mordanting processes; for dyeing acetate with insoluble dyestuffs; for producing foam in fire extinguishers; as a means for improving the absorption power of fibrous bodies; and as an aid in softening baths for hides and skins.
  • esters are valuable emulsifiers for insecticide compositions and agricultural sprays, such as DDT, 2-4-D, toxaphene, chlorodane. These esters are valuable for use as additions to petroleum products, as additives for fuel oils, hydraulic fluids, lubricating oils, cutting oils, greases, as additives to the water or brine used for oil recovery from oil-bearing strata by flooding techniques.
  • metal cleaning compositions dry cleaning compositions
  • additives for rubber latices foam inhibitors for synthetic rubber latex emulsions
  • froth flotation agents additives for road building materials, as air entraining agents for concrete or cement
  • additives to asphalt compositions for incorporation into adhesives, paint, linoleum, for use in bonding agents used in various insulating and building materials, as refining aids in wood digesters to prepare pulp, as additives to pulp slurries in beating operations to prevent foaming and also to aid the beating operation in paper making.
  • esters are also useful as emulsifiers for emulsion polymerization, as mercerizing assistants, wetting agents, rewetting agents, dispersing agents, detergents, penetrating agents, softening agents, cutting oils, lime soap dispersants, dishwashing agents, disinfectants, insecticides, herbicides, mothproofing agents, bacteriocides, fungicides and biocides.
  • esters are especially useful in breaking petroleum emulsions. They may be used to break emulsions of crude petroleum and salt water as obtained from oil wells by introducing the agent into the well, or to break or prevent emulsions which would result from the water flooding process for recovering oil from oil bearing strata. They may also be used to break emulsions encountered in a petroleum refining process.
  • They are useful as corrosion inhibitors, as rust inhibitors, in the protection of metals especially ferrous metals, in acid pickling baths, in acid cleaning compositions and in electroplating baths.
  • esters are valuable in the preparation of skin creams, lotions, salves and other cosmetic preparations such as home hairwave sets, shampoos, toothpastes, etc.
  • The may also be of value in food .products as foaming agents, emulsifying agents, and softening agents.
  • EXAMPLE I In a 500 cc. 4-necked flask equipped with a stirrer, thermometer and downward condenser to receiver EXAMPLE II 63.3 grams (0.4 mole) of pelargonic acid, 51.6 grams (0.4 mole) of N-hydroxyethyl-pyrrolidone and 1.1 grams of p-toluenesulfonic acid monohydrate were heated together at 125160 C./30 mm. for a total of 3% hours during which time a total distillate of 7.3 grams was removed. The final product was neutralized by the addition of 1.0 gram of diethanolamine. Ester No.:199 or 95.3%.
  • EXAMPLE IV 84.8 grams (0.4 mole) of double distilled coconut fatty acids, 51.6 grams (0.4 mole) of N-hydroxyethylpyrrolidone and 1.3 grams of p-toluenesulfonic acid monohydrate were reacted together at 120l60 C./ 30 mm. over a period of 5 hours during which time a total of 8.0 grams of distillate were distilled otf. The final product was neutralized by the addition of 1.0 gram of diethanolamine.
  • EXAMPLE V 68.8 grams (0.4 mole of capric acid, 51.6 grams (0.4 mole) of N-hydroxyethyl-pyrrolidone and 1.2 grams of p-toluenesulfonic acid monohydrate were reacted at 112- 166 C./30 mm. over a period of five hours during which time a total of 7.5 grams of distillate were removed. The final product was neutralized by the addition of 1.2 grams of diethanolamine. Ester No. :201.
  • Example I was repeated with the exception that 51.6 grams of N-hydroxyethyl-pyrrolidone were replaced by 57.2 grams of N-hydroxypropyl-pyrrolidone. After neutralization with diethanolamine the ester No. was 162 or 93.9%.
  • a ten gram swatch each of nylon, Orlon, Dacron and Acrilan fabrics were separately immersed into a (1% aqueous solution of the ester of Example I to obtain a 100% pick-up of the solution of the fabric, i.e., until each of the wetted swatches weighs 20 grams.
  • the wetted (coated) fabrics were dried in an oven at 50 C. and then conditioned for the testing in the testing chamber at a relative humidity of 40% and a temperature of 75 F. for about 25-35 minutes. The same procedure was repeated with the esters of Examples II to X.
  • Synthetic fibers selected from the class consisting of linear superpolyamides, polyacrylonitrile, and polyethylgrams (0.4 mole) of N-hydroxyethyl-pyrrolidone and ene tetraphthalate having from 0.5% to 2.5% by weight 6 of an antistatic agent as a coating thereon, said agent hav- 5.
  • R1HC-(I3R 5 R1HO ⁇ /C O H210 [CH2 H 0 0:0 l (I) 10 (CHM 1:0 R3 (3:0 wherein R and R represent a member selected from the ((13K) BCHS class consisting of hydrogen, methyl and ethyl groups, 15 2 1 R represents an alkylene radical of from 1 to 6 carbon atoms, and R represents a hydrocarbon residue of a fatty acid of from 5 to 23 carbon atoms.

Description

United States Patent 3,212,927 ANTISTATIC COATING FOR SYNTHETIC FABRICS Earl P. Williams, Pen Argyl, Pa., assignor to General Aniline & Film Corporation, New York, N.Y., a corporation of Delaware No Drawing. Filed Oct. 1, 1964, Ser.No. 400,919 6 Claims. (Cl. 117138.8)
This application is a continuation-in-part of application Serial No. 270,202, filed on- April 3, 1963, now abandoned.
This invention relates to synthetic fabrics containing fatty acid esters of N-hydroxyalkyl-pynrolidones as antistatic coatings thereon.
I have discovered that N-hydroxyalkyl-pyrrolidone esters of saturated and unsaturated fatty acids of from 6 to 24 carbon atoms are excellent antistatic coatings for synthetic fabrics such as Acrilan, Dacron, nylon, Orion, etc., when employed in an antistatic coating amount varying from 0.5 to 2.5% by weight of the fabric. The fabric may be dyed or undyed.
The esters are characterized by the following general formula:
wherein R and R represent either hydrogen, methyl or ethyl groups, R represents an alkylene radical containing from 1 to 6 carbon atoms and R represents a hydrocarbon residue of a fatty acid of 6 to 24 carbon atoms.
The esters are prepared by esterifying 1 mole of a fatty acid of 6 to 24 carbon atoms with 1 mole of an N-hydroxyalkyl-pyrrolidone by conventional means, preferably in the presence of an acid catalyst such as p-toluene sulfonic acid monohydrate. The N-hydroxyalkyl-pyrrolidones are prepared in the well known manner by reacting at 250 C. 1 mole of an alkanolamine of 1 to 6 carbon atoms with 1 mole of either butyrolactone, S-methyl butyrolactone, 4methyl butyrolactone, 4-ethyl butyrolactone, S-methyl butyrolacto-ne, S-ethyl butyrolactone or 3.3-dimethyl butyrolactone. The alkanolamines utilized in such preparation consist of methanolamine, ethanolamine, 3-amino-propanol-l, 4-amino-butano1-1, S-aminopentano -1 or 6-arnino-hexanol-1.
The fatty acids of 6 to 24 carbon atoms that are esterified with the N-hydroxyalkyl-pynrolidones may be either saturated or unsaturated, aliphatic or aromatic. The nature or character of the acid is immaterial so long as it is capable of esterification with a hydroxyl group. Acids of this type include caproic, capry-llic, capric, lauric, myristic, palmitic, stearic, oleic, linoleic, behenic, tetracosanic, tall oil, hydrogenated tall oil, napthanic or abietic acid, phenoxyalkylcarboxylic, halogenated phenoxylalkylcarboxylic acids, o-p'hthalic acid, alkyl benzoic acids, such as dodecyl-benzoic acid, nonylbenzoic acid, octylbenzoic acid; acids from oxo alcohols and aldehydes, acids from oxidized petroleum fractions; acid mixtures from various natural plant and animal oils such as olive, palm, tallow, castor, peanut, coconut, soybean, cottonseed, ucuhuba, linseed; fish oils such as cod, herring, menhaden, etc.; neatsfoot, sperm, corn, butter, babasse, kapok, hempseed, mustard, nape, safliower, sesame, etc., as well as Emery dimer acids and trimer acids.
3,212,927 Patented Oct. 19, 1965 The esters, prepared as above, are not only effective antistatic coating agents for synthetic fabrics, but are also useful in many diversified applications. For instance, they can be used as wetting, frothing or washing agents in the treatment and refining of textiles; for converting liquid or solid substances, which per se are insoluble in water, into creamy emulsions; for carbonizing; for dyeing; for the pasting of dyestuffs; for fulling; sizing; impregnating and bleaching treatments; as cleansing agents in hard Water; in tanning and mordanting processes; for dyeing acetate with insoluble dyestuffs; for producing foam in fire extinguishers; as a means for improving the absorption power of fibrous bodies; and as an aid in softening baths for hides and skins.
In addition, these esters are valuable emulsifiers for insecticide compositions and agricultural sprays, such as DDT, 2-4-D, toxaphene, chlorodane. These esters are valuable for use as additions to petroleum products, as additives for fuel oils, hydraulic fluids, lubricating oils, cutting oils, greases, as additives to the water or brine used for oil recovery from oil-bearing strata by flooding techniques.
Other valuable uses are in the metal cleaning compositions, dry cleaning compositions, additives for rubber latices, foam inhibitors for synthetic rubber latex emulsions, froth flotation agents, additives for road building materials, as air entraining agents for concrete or cement, additives to asphalt compositions, for incorporation into adhesives, paint, linoleum, for use in bonding agents used in various insulating and building materials, as refining aids in wood digesters to prepare pulp, as additives to pulp slurries in beating operations to prevent foaming and also to aid the beating operation in paper making.
These esters are also useful as emulsifiers for emulsion polymerization, as mercerizing assistants, wetting agents, rewetting agents, dispersing agents, detergents, penetrating agents, softening agents, cutting oils, lime soap dispersants, dishwashing agents, disinfectants, insecticides, herbicides, mothproofing agents, bacteriocides, fungicides and biocides.
They are valuable as antifogging agents for use on glass and other surfaces where the accumulation of an aqueous fog is detrimental. They are useful in the rayon industry as additives to the dope and as aids in clarifying viscose rayon.
These esters are especially useful in breaking petroleum emulsions. They may be used to break emulsions of crude petroleum and salt water as obtained from oil wells by introducing the agent into the well, or to break or prevent emulsions which would result from the water flooding process for recovering oil from oil bearing strata. They may also be used to break emulsions encountered in a petroleum refining process.
They are useful as corrosion inhibitors, as rust inhibitors, in the protection of metals especially ferrous metals, in acid pickling baths, in acid cleaning compositions and in electroplating baths.
Other valuable uses are as solvents, as cleaning agents, for paint brushes, as additives for paints, lacquers, and varnishes, as lubricants, as greases and stufiing agents.
These esters are valuable in the preparation of skin creams, lotions, salves and other cosmetic preparations such as home hairwave sets, shampoos, toothpastes, etc.
The may also be of value in food .products as foaming agents, emulsifying agents, and softening agents.
The following are examples of the preparation of the esters and their application as antistatic agents for synthetic fabrics.
EXAMPLE I In a 500 cc. 4-necked flask equipped with a stirrer, thermometer and downward condenser to receiver EXAMPLE II 63.3 grams (0.4 mole) of pelargonic acid, 51.6 grams (0.4 mole) of N-hydroxyethyl-pyrrolidone and 1.1 grams of p-toluenesulfonic acid monohydrate were heated together at 125160 C./30 mm. for a total of 3% hours during which time a total distillate of 7.3 grams was removed. The final product was neutralized by the addition of 1.0 gram of diethanolamine. Ester No.:199 or 95.3%.
EXAMPLE III In a similar manner 113.7 grams (0.4 mole) of stearic acid, 51.6 grams (0.4 mole) of N-hydroxyethyl-pyrrolidone and 1.6 grams of p-toluenesulfonic acid mono hydrate were heated at l30-l60 C./30 mm. over a period of 2% hours during which time a total of 6.9 grams of distillate were removed. The final product was neutralized by the addition of 1.5 grams of diethanolamine. Ester No.:110.
EXAMPLE IV 84.8 grams (0.4 mole) of double distilled coconut fatty acids, 51.6 grams (0.4 mole) of N-hydroxyethylpyrrolidone and 1.3 grams of p-toluenesulfonic acid monohydrate were reacted together at 120l60 C./ 30 mm. over a period of 5 hours during which time a total of 8.0 grams of distillate were distilled otf. The final product was neutralized by the addition of 1.0 gram of diethanolamine.
EXAMPLE V 68.8 grams (0.4 mole of capric acid, 51.6 grams (0.4 mole) of N-hydroxyethyl-pyrrolidone and 1.2 grams of p-toluenesulfonic acid monohydrate were reacted at 112- 166 C./30 mm. over a period of five hours during which time a total of 7.5 grams of distillate were removed. The final product was neutralized by the addition of 1.2 grams of diethanolamine. Ester No. :201.
' EXAMPLE VI 102.4 grams (0.4 mole) of palmitic acid, 51.6 grams (0.4 mole) of N-hydroxyethyl-pyrrolidone and 1.5 grams of p-toluenesulfonic acid monohydrate were reacted at 110-170 C./ 30 mm. over a period of 4 /2 hours during which time a total of 7.2 grams of distillate were removed. The final product was then neutralized by the addition of 1.2 grams of diethanolamine.
1.7 grams of p-toluenesulfonic acid monohydrate were reacted at 120-155 C./30 mm. over a period of 4 hours during which time a total of 7.2 grams of distillate were removed. The final product was then neutralized by the addition of 1.7 grams of diethanolamine. Ester No.:137.
EXAMPLE VIII Example I was repeated with the exception that 51.6 grams of N-hydroxyethyl-pyrrolidone were replaced by 57.2 grams of N-hydroxypropyl-pyrrolidone. After neutralization with diethanolamine the ester No. was 162 or 93.9%.
EXAMPLE IX Example III was repeated with the exception that 51.6 grams of N-hydroxyethyl-pyrrolidone were replaced by 62.8 grams of N-hydroxybutyl-pyrrolidone. After neutralization with diethanolamine the ester No. was 106 or 80%.
EXAMPLE X Example III was repeated with the exception that 51.6 grams of N-hydroxyethyl-pyrrolidone were replaced by 74.0 grams of N-hydroxyhexyl-pyrrolidone. After neutralization with diethanolamine the product was obtained with an ester No. of 105 or 84.3%.
The method used in determining the antistatic activity of the esters of Examples I to X inclusive is described in the 1957 Technical Manual and Year Book of the American Association of Textile Chemists and Colorists, vol. 33, page 128, titled Antistatic Finish Materials, Determination of the Electrical Resistivity of Fabrics test method 76-1954. In employing this method, the standard procedure is to immerse a ten gram swatch of the synthetic fabric in a 1% solution of the ester antistatic coating agentto 100% pick-up of the solution so that the wetted (coated or sized) fabric weighs twice as much. The wetted (coated) fabric is then dried and conditioned for -the test in the manner described in the Manual.
The esters of Examples I to X were evaluated as follows:
A ten gram swatch each of nylon, Orlon, Dacron and Acrilan fabrics were separately immersed into a (1% aqueous solution of the ester of Example I to obtain a 100% pick-up of the solution of the fabric, i.e., until each of the wetted swatches weighs 20 grams. The wetted (coated) fabrics were dried in an oven at 50 C. and then conditioned for the testing in the testing chamber at a relative humidity of 40% and a temperature of 75 F. for about 25-35 minutes. The same procedure was repeated with the esters of Examples II to X.
. The results of the foregoing test method are shown in Table I.
Table I.'Antistatic activity (log ohms/sq), based on 1 0f antistatic agent by weight of fiber Antistatic Agent of Examples Fiber I II III IV V VI VII VIII IX X Nylon 10. 89 10. 83 10.80 10. 79 10. 69 10.87 10. 80 10. 68 10. 80 10. 88 Orlon- 9. 42 10. 38 10. 40 10. 10. 52 9. 10. 21 10. 57 10. 22 9. Dacrorn 10. 46 I0. 97 10. 90 10. 92 10. 93 10. 44 9. 89 I0. 95 9. 90 10. 56 Acr1lan 10. 20 10. 74 10. 72 10. 80 10. 79 10. 20 9. 79 10. 83 9. 85 10. 30
Average 10. 24 10. 68 10. 10. 74 10. 73 10. 27 10. 17 10. 76 10. 19 10. 34
For controls all of the foregoing fibers were treated with water alone and had resistivities in log ohms/sq.
greater than 14.0 for each fiber.
EXAMPLE VII 118.4 grams (0.2 mole) of Emerys Dimer Acids, 51.6
I claim: 1. Synthetic fibers selected from the class consisting of linear superpolyamides, polyacrylonitrile, and polyethylgrams (0.4 mole) of N-hydroxyethyl-pyrrolidone and ene tetraphthalate having from 0.5% to 2.5% by weight 6 of an antistatic agent as a coating thereon, said agent hav- 5. A synthetic fiber as defined in claim 1 wherein the ing the following general formula: antistatic agent has the formula:
/R R1HC-(I3R 5 R1HO\ /C=O H210 [CH2 H 0 0:0 l (I) 10 (CHM 1:0 R3 (3:0 wherein R and R represent a member selected from the ((13K) BCHS class consisting of hydrogen, methyl and ethyl groups, 15 2 1 R represents an alkylene radical of from 1 to 6 carbon atoms, and R represents a hydrocarbon residue of a fatty acid of from 5 to 23 carbon atoms.
2. A synthetic fiber as defined in claim 1 wherein the A Synthet1 fiber as definad 1n damn I Wherem the antistatic agent has the formula: antstatlc agent has the formula:
Hz(|3CHz H2O C=O .bll' H2? CH2 (CHM 25 H2O\ /C=O f (1 0 (OHM 2)10CHa (l 3. A synthetic fiber as defined in claim 1 wherein the antistatic agent has the formula: ((BHMOHS 112C CH2 1112): I References Cited by the Examiner 5 UNITED STATES PATENTS (5:0 2,718,478 9/55 Fluck etal 117-1395 ((IJHWCH, 2,882,262 4/59 Smith et a1. 260-805 h 2,892,820 6/59 Stewart et a1. 26080.5 4 A synthet1c fiber 3S defined 111 6131111 1 Whfil'fim t e B et 1 antlstatic agent has the formula:
H FOREIGN PATENTS 2C$H2 6 0:0 7,780 11/57 Japan.
OTHER REFERENCES Yakahama et al.: Chemical Abstracts, vol. 52, page 13802d, 1958. E=o WILLIAM D. MARTIN, Primary Examiner.

Claims (1)

1. SYNTHETIC FIBERS SELECTED FROM THE CLASS CONSISTING OF LINEAR SUPERPOLYAMIDES, POLYACRYLONITRILE, AND POLYETHYLENE TETRAPHTHALATE HAVING FROM 0.5% TO 2.5% BY WEIGHT OF AN ANTISTATIC AGENT AS A COATING THEREON, SAID AGENT HAVING THE FOLLOWING GENERAL FORMULA:
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3353993A (en) * 1964-04-28 1967-11-21 Asahi Chemical Ind Method for imparting antistantic properties to textile materials

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2718478A (en) * 1954-01-27 1955-09-20 American Cyanamid Co Antistatic treatment of fibrous materials
US2882262A (en) * 1956-05-14 1959-04-14 Eastman Kodak Co N-(acryloxyalkyl)- and n-(methacryloxyalkyl)-2-pyrrolidones and polymers thereof
US2892820A (en) * 1956-03-29 1959-06-30 California Research Corp Oil soluble polymers containing polyalkylene glycol side-chains
US2945863A (en) * 1958-06-24 1960-07-19 Gen Aniline & Film Corp Amides of aminoalkyl pyrrolidones

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2718478A (en) * 1954-01-27 1955-09-20 American Cyanamid Co Antistatic treatment of fibrous materials
US2892820A (en) * 1956-03-29 1959-06-30 California Research Corp Oil soluble polymers containing polyalkylene glycol side-chains
US2882262A (en) * 1956-05-14 1959-04-14 Eastman Kodak Co N-(acryloxyalkyl)- and n-(methacryloxyalkyl)-2-pyrrolidones and polymers thereof
US2945863A (en) * 1958-06-24 1960-07-19 Gen Aniline & Film Corp Amides of aminoalkyl pyrrolidones

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3353993A (en) * 1964-04-28 1967-11-21 Asahi Chemical Ind Method for imparting antistantic properties to textile materials

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