US3247018A - Process for treating textile materials - Google Patents

Process for treating textile materials Download PDF

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Publication number
US3247018A
US3247018A US232275A US23227562A US3247018A US 3247018 A US3247018 A US 3247018A US 232275 A US232275 A US 232275A US 23227562 A US23227562 A US 23227562A US 3247018 A US3247018 A US 3247018A
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United States
Prior art keywords
textile materials
acid
parts
carbon atoms
reaction product
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
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US232275A
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English (en)
Inventor
Hagge Walter
Dusing Josef
Kolbe Joachim
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Bayer AG
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Bayer AG
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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
    • 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
    • D06M13/46—Compounds containing quaternary nitrogen atoms
    • 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
    • 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
    • D06M13/405—Acylated polyalkylene polyamines
    • 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

Definitions

  • the present invention relates to the treatment of textile materials; more particularly it concerns a process in which the textile materials are treated with reaction products prepared by reacting (A) esters of higher fatty acids containing 12 to 20 carbon atoms condensed with alcohols containing 4 to 12 carbon atoms and/or polyhydric alcohols containing 2 to 6 hydroxyl groups with (B) amide amines in the form of salts or quaternization products, such as are obtainable by the action 1-l.7 mole of a carboxylic acid containing 62() carbon atoms or a functional derivative thereof on 1 mol of a diamine of the formula in which R and R stand independently from one another for an alkyl radical containing 1 to 8 carbon atoms and n is a number from 2-4, the amount of diamine employed being not more than 8 percent by weight of the reaction product.
  • A esters of higher fatty acids containing 12 to 20 carbon atoms condensed with alcohols containing 4 to 12 carbon atoms and/or polyhydric alcohols containing 2
  • esters on which the reaction products to be used according to the present invention can be based there may be mentioned, for example, tallow, coconut fat, olive oil, castor oil, palm kernel oil, lanolin, sperm oil and Wool fat; there may further be mentioned the esters obtainable from polyglycerol and higher fatty acids containing 12 to 20 carbon atoms, and the esters which result on heating polvglycerol or sorbitol with fats, for example beef taliow or coconut fat, in the presence of caustic alkalies.
  • amide amines there may be considered the products which are obtained when carboxylic acids with 6 to 20 carbon atoms, such as caprylic acid, lauric acid, coconut fatty acid, palmitic acid or palm kernel fatty acid, stearic acid or oleic acid or their chlorides or methyl esters are treated dropwise with diamines of the given formula, such as diethylamino ethylamine, dimethylamino propylamine, methylethylamino propylamine or diethylamino butylamine, at about 170-180 C., and then held for two hours in vacuum and a further two hours Without vacuum at this temperature.
  • diamines of the given formula such as diethylamino ethylamine, dimethylamino propylamine, methylethylamino propylamine or diethylamino butylamine
  • the amide-amines formed are then converted into salts at about 100-130" C., with for example sulfuric acid, phosphoric -acid, formic acid, acetic acid, or lactic acid.
  • sulfuric acid for example sulfuric acid, phosphoric -acid, formic acid, acetic acid, or lactic acid.
  • amide amines for example, dimethylor diethyl-sulfate, ethyl bromide, benzyl chloride, epichiorohydrin, chloracetamide or N-rnethylol chioracetamide.
  • reaction of the esters with the salts or quaternization products of the amide amines is expediently carried out by heating for one or two hours at l130 C.
  • reaction products can contain up to 70 percent by weight of the ester component, without the stability of the aqueous liquor produced suffering.
  • the process of the present invention may be applied to textile materials of the most various kinds, e.g., on fibers or threads of wool, cotton, regenerated cellulose, cellulose acetate, polyurethanes, polyamides, polyesters, polyoleilnes, polyacrylonitrile, and/ or mixed polymers of acrylonitrile with other vinyl compounds, or on fabrics or knitted goods produced thereform.
  • the treatment of the textile materials can proceed in the customary manner, for example by agitating the materials in aqueous baths which contain the reaction products and are adjustecl as desired to neutral, alkaline or acid reaction, for some time, expediently at 3060 C., and then drying at about 7090 C.
  • the present process may also be applied to yarns in vats and packing machines, on conical cross-wound bobbins and on piece goods of any kind, on the reel and on the foulard.
  • reaction product in the treatment bath is about 2-20 g./ litre.
  • reaction products are especially suitable which were made with the use of Wool fat, lanolin, or mixtures of wool fat and tallow or of lanolin and castor oil.
  • the stockings and socks treated with these products possess a soft and full handle and the stockings can also be very readily shaped, since they are simultaneously rendered antistatic.
  • reaction products which are produced with the use of quaternization products of the amide amines are outstandingly suitable for finishing and impregnating purposes in combination with paramn or wax emulsions containing aluminum or zirconium salts or in combination with water-soluble urea or melamine formaldehyde precondensates.
  • reaction products of the present invention can be employed also with other textile assistants, eg' with wetting agents or optical brighteners.
  • the textile materials treated according to the invention in general have no unpleasant amine odour.
  • reaction products prepared from salts or quaternization products of amide amines in the presence of polyglycerol; such reaction products are odourless and the textile materials treated therewith likewise possess no undesirable amine smell.
  • Example 1 A fabric of polyacrylonitrile fibres was agitated for 30 minutes at a liquor-to-goods ratio of 20:1 at 40 C., in an aqueous bath which contained per litre 2.5 g. of the paste described below. The fabric was then centrifuged and dried at 80 C. The fabric thus treated which possessed no unpleasant smell, had a full and soft handle; it showed at the same time an antistatic finish.
  • the paste used was prepared in the following manner:
  • tallow fatty acid glycerol ester obtained by heating 1 mol of tallow and 2 mols of polyglycerol of molecular weight 170 in the presence of 1% by weight of potassium hydroxide to 18Q200 C., were stirred for 2% hours at 100 C. with 20 parts of Vaseline and 300 parts of the acetate of an amide amine which had been produced, according to col. 1, lines 41-59 of the specification, by heating 152 parts of a fatty acid mixture which contained altogether 98% by weight of saturated fatty acids, i.e., 62% of stearic acid, 32% of palmitic acid and 4% of myristic acid, to a temperature of 170180 C.
  • Example 2 Fibers of polymeric e-caprolactam (thickness 1.4/30 mm.) were treated in the manner described in Example 1 in an aqueous bath which contained 1 g. per litre of the paste there described. The fibres thus treated had a soft and pleasant handle; the further working up proceeded without trouble.
  • Example 3 Stocking of threads, or socks of fibers, produced from polymeric e-caprolactam, were treated in the manner described in Example 1 with an aqueous liquor containing 3 g. per litre of the paste described below. The stockings and socks thus treated then possessed a full, soft and smooth handle; they no longer felt rough. At the same time they acquired an antistatic finish.
  • the paste employed was produced in the following manner:
  • Example 4 Hanks or piece goods produced from 50 parts of polyester fibres and 50 parts of wool, were agitated for 30 minutes at 45 C. at a liquor-to-goods ratio of :1 in an aqueous bath containing per litre 3 g. of the paste described below. After centrifuging and drying, the goods possessed a clearly improved feel; furthermore, they were given an antistatic finish.
  • the paste employed was produced in the following manner:
  • a process for treating textile materials comprising impregnating said materials with an active amount of the reaction product of (A) an ester obtained by condensing a higher fatty acid containing 12-20 carbon atoms with a member selected from the group consisting of a monohydric alcohol of 412 carbon atoms, and a polyhydric alcohol containing 26 hydroxyl groups; with (B) a member selected from the group consisting of the salt and the quaternization product of an amide amine obtained by reacting a diamine of the formula wherein R and R stand independently defined as alkyl having 18 carbon atoms and n is an integer of 2-4, with a reactive amount of (b) carboxylic acid having 6-20 carbon atoms,
  • the amount of diamine being not more than 8% by weight of the reaction product of (A) and (B).
  • the textile materials contain a substantial amount of at least one member of the group consisting of regenerated cellulose, cellulose acetate, polyurethane, polyamide, polyester, poly olefine, polyacrylonitrile, and wool.
  • the (B) amide amine is obtained by reacting carboxylic acid selected from the group consisting of caprylic acid, lauric acid, coconut fatty acid, palmitic acid, palm kernel fatty acid, stearic acid, oleic acid, and the corresponding chlorides and methylesters, with an amine selected from the group consisting of diethylamino-ethylamine, dimethylamino propylamine, methylethylamino propylamine, and diethylamino butylamine.
  • carboxylic acid selected from the group consisting of caprylic acid, lauric acid, coconut fatty acid, palmitic acid, palm kernel fatty acid, stearic acid, oleic acid, and the corresponding chlorides and methylesters
  • reaction product of (A) and (B) is obtained by employing the quaternization product of the amide amine in the presence of an effective amount of polyglycerol.
  • polyacrylonitrile material is agitated in an aqueous bath containing 2-20 gm. per liter of active ingredient in a liquor-to-goods ratio of about 20:1, at about 3060 C., and thereafter drying the material at a temperature of about 70-90 C.
  • a process for treating textile materials comprising impregnating said materials with an active amount of the reaction product of (A) an ester obtained by condensing a fatty acid containing 12-20 carbon atoms with a member selected from the group consisting of tallow, coconut fat, olive oil, caster oil; palm kernel oil, lanolin, sperm oil and wool fat; with (B) a member selected from the group consisting of the salt and the quaternization product of an amide amine obtained by reacting a diamine of the formula wherein R and R stand independently defined as alkyl having 1-8 carbon atoms and n is an integer of 2-4, with a reactive amount of (b) carboxylic acid having 6-20 carbon atoms, the amount of diarnine being not more than 8% by weight of the reaction product of (A) and (B).

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US232275A 1961-10-25 1962-10-22 Process for treating textile materials Expired - Lifetime US3247018A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF35208A DE1149687B (de) 1961-10-25 1961-10-25 Verfahren zur Behandlung, insbesondere antistatischen Ausruestung von Textilmaterialien

Publications (1)

Publication Number Publication Date
US3247018A true US3247018A (en) 1966-04-19

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US232275A Expired - Lifetime US3247018A (en) 1961-10-25 1962-10-22 Process for treating textile materials

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US (1) US3247018A (is")
AT (1) AT238134B (is")
BE (1) BE623927A (is")
DE (1) DE1149687B (is")
GB (1) GB962421A (is")
NL (1) NL284615A (is")

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3390009A (en) * 1964-08-21 1968-06-25 Standard Chem Products Inc Process for rendering hydrophobic fibers containing textile antistatic and the treating composition
US4082887A (en) * 1976-05-14 1978-04-04 E. I. Du Pont De Nemours And Company Coating composition for a fibrous nonwoven sheet of polyolefin
US4360437A (en) * 1980-01-11 1982-11-23 The Proctor & Gamble Company Concentrated textile treatment compositions and method for preparing them
WO2014035921A1 (en) * 2012-08-27 2014-03-06 Pcc Chemax, Inc. Anti-static agent for polymer resins

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH667362GA3 (is") 1981-03-23 1988-10-14

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2103497A (en) * 1934-05-04 1937-12-28 Celanese Corp Artificial textile material and method of preparing the same
US2201041A (en) * 1938-03-01 1940-05-14 Warwick Chemical Company Fatty derivatives of alkylated amines
US2205042A (en) * 1937-10-26 1940-06-18 Du Pont Softening of textile materials and compositions therefor
US2964470A (en) * 1956-03-19 1960-12-13 American Viscose Corp Tire cord fiber lubricant

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2103497A (en) * 1934-05-04 1937-12-28 Celanese Corp Artificial textile material and method of preparing the same
US2205042A (en) * 1937-10-26 1940-06-18 Du Pont Softening of textile materials and compositions therefor
US2201041A (en) * 1938-03-01 1940-05-14 Warwick Chemical Company Fatty derivatives of alkylated amines
US2964470A (en) * 1956-03-19 1960-12-13 American Viscose Corp Tire cord fiber lubricant

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3390009A (en) * 1964-08-21 1968-06-25 Standard Chem Products Inc Process for rendering hydrophobic fibers containing textile antistatic and the treating composition
US4082887A (en) * 1976-05-14 1978-04-04 E. I. Du Pont De Nemours And Company Coating composition for a fibrous nonwoven sheet of polyolefin
US4360437A (en) * 1980-01-11 1982-11-23 The Proctor & Gamble Company Concentrated textile treatment compositions and method for preparing them
WO2014035921A1 (en) * 2012-08-27 2014-03-06 Pcc Chemax, Inc. Anti-static agent for polymer resins

Also Published As

Publication number Publication date
DE1149687B (de) 1963-06-06
NL284615A (is")
AT238134B (de) 1965-01-25
GB962421A (en) 1964-07-01
BE623927A (is")

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