US3038820A - Process for imparting a soft feel to textile fibers - Google Patents

Process for imparting a soft feel to textile fibers Download PDF

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US3038820A
US3038820A US800968A US80096859A US3038820A US 3038820 A US3038820 A US 3038820A US 800968 A US800968 A US 800968A US 80096859 A US80096859 A US 80096859A US 3038820 A US3038820 A US 3038820A
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fibers
parts
carbon atoms
ethylene oxide
imparting
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Albrecht Otto
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BASF Schweiz AG
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Ciba AG
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/13—Fugitive dyeing or stripping dyes
    • D06P5/138—Fugitive dyeing or stripping dyes fugitive dyeing
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2618—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen
    • C08G65/2621—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen containing amine groups
    • C08G65/2624—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen containing amine groups containing aliphatic amine groups
    • 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
    • D06M13/372—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 containing etherified or esterified hydroxy groups ; Polyethers of low molecular weight
    • 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
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/60—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing polyethers
    • D06P1/607—Nitrogen-containing polyethers or their quaternary derivatives
    • D06P1/6073—Nitrogen-containing polyethers or their quaternary derivatives containing CON=, OCON=, SO2N=, OSO2N= groups
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/60—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing polyethers
    • D06P1/607—Nitrogen-containing polyethers or their quaternary derivatives
    • D06P1/6076—Nitrogen-containing polyethers or their quaternary derivatives addition products of amines and alkylene oxides or oxiranes
    • 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

  • This invention provides a new process for imparting a soft feel to organic textile fibers which comprises applying to said fibers in an aqueous bath a polyglycol ether derivative, in which each carbon atom bound to an oxygen atom is bound to a single oxygen atom, and which contains the radical of an amine of the formula 1 H N-Alkylene-ENH-AlkyleneH- NH in which in represents a small whole number, and in which there are bound to nitrogen atoms of the amine radical at least two acyl radicals together containing at least 20 carbon atoms and derived from fatty acid.
  • the aforesaid polyglycolether derivative can be made by introducing a polyglycol ether chain, advantageously with the aid of ethylene oxide, into an acyl-compound which is derived from an amine of the Formula 1 and contains at least two acyl radicals which are derived from fatty acids and together contain at least 20 carbon atoms, and in which acyl compound each carbon atom bound to an oxygen atom is bound to a single oxygen atom.
  • this invention provides a process for imparting a soft feel to organic textile fibers which comprises treating said fibers with an aqueous bath which contains a compound which in its free base state is a reaction product of 8-30 mols of ethylene oxide and 1 mol of an N-acylated alkylene polyamine which contains 2 to 4 nitrogen atoms separated from each other by alkylene groups containing 2 to 3 carbon atoms, in which N-acylated alkylene polyamine at least 2 nitrogen atoms are acylated by a saturated aliphatic monocarboxylic acid containing 12 to 18 carbon atoms, and drying the fibers.
  • an aqueous bath which contains a compound which in its free base state is a reaction product of 8-30 mols of ethylene oxide and 1 mol of an N-acylated alkylene polyamine which contains 2 to 4 nitrogen atoms separated from each other by alkylene groups containing 2 to 3 carbon atoms, in which N-acylated alkylene polyamine at least 2 nitrogen atoms are
  • starting materials for making the ethylene oxide reaction products there may be used, for example, amines of the kind defined above which are diacylated with fatty acids, advantageously acylamino-compounds of the formula I I "1 l](-O CR1)p in which the radicals R are saturated aliphatic hydrocarbon radicals containing 1-17 carbon atoms, 11 represents an integer from 1 to 2, m represents an integer from 1 to 3, p is an integer from 2 to 4 and is greater than m by at most 1, and the radicals CO--R together contain at least 20 carbon atoms.
  • N-acylamino compounds corresponding to the general formula 3,038,820 Patented June 12, 1962 wherein n, p, q, k and In each represent an integer from 1 to 2, R R R and R each represent a saturated aliphatic hydrocarbon radical containing 1 to 7 carbon atoms, at least two of the acyl radicals containing 12 to 18 carbon atoms each.
  • the acyl-compounds are derived from aliphatic alkylene polyamines which contain 2 to 4 nitrogen atoms separated from each other by at least one divalent alkylene group containing 2 to 3 carbon atoms, preferably by at least one ethylene group, for example, from ethylene diamine, propylene diamine, diethylene triamine or triethylene tetramine. Especially advantageous are the acyl compounds of diethylene triamine.
  • acyl compounds derived from diethylene triamine correspond to the formula in which R represents a saturated aliphatic hydrocarbon radical containing 1 to 17, preferably 11-17, carbon atoms, 17 represents an integer from 2 to 3, and the acyl radicals OCR together contain at least 20 carbon atoms, at least 2 acyl radicals each containing at least 8 carbon atoms.
  • acyl compounds derived from diethylene triamine correspond to the formula wherein 11 represents an integer from 1 to 2, R R and R each represent a saturated aliphatic hydrocarbon radical containing 1 to 17 carbon atoms, at least two of the acyl radicals containing 12 to 18 carbon atoms each.
  • the acyl compounds used as starting materials for making the polyglycol ether derivatives therefore contain at least two Nacyl radicals, the acyl radicals must together contain at least 20 carbon atoms, and it is generally advantageous that there should be present in the molecule at least two acyl radicals each containing at least 8 carbon atoms.
  • the acyl radicals of the compounds of the Formulae 2, 3, 4 and 5 contain from 1 to 22, preferably from 12 to 18, carbon atoms. Accordingly, the acyl radicals are derived, for example, from advantageously unbranched saturated fatty acids of high molecular weight, such as lauric acid (for example, in the form of coconut oil fatty acid), myristic acid, palmitic acid, arachic acid or behenic acid. Especially advantageous are, for example, acyl compounds derived from stearic acid, and especially those of which the acyl radicals are those of so-called commercial stearic acid consisting for the greater part of stearic acid. It the acyl radicals are derived from fatty acids of low molecular weight they consist, for example, of an acetyl, propionyl or butyryl radical.
  • acyl-compounds used as starting materials for mak- O m-l ing the polyglycol ether derivatives can be prepared in produced fibers to be subjected to the process of this inknown manner from the appropriate polyamines and carvention are those of polyacrylonitrile, polyesters, polyboxylic acids, or, if desired, functional derivatives of these amides or polyurethanes; chemically modified cellulosic acids, such as their acid halides, especially their acid fibers are those of cellulose acetate. or cellulose ether; chlorides, or acid anhydrides.
  • acyl radicals of low and regenerated cellulosic fibers are those of rayon.
  • Bemolecular weight are introduced in addition to acyl radisides these synthetically produced or semi-synthetically cals of high molecular weight, it is of advantage to introproduced fibers there come into consideration animal prise the former acyl radicals last. fibers, such as wool or silk and natural cellulosic fibers,
  • the acylamino-compounds are reacted with ethylene such as cotton or linen.
  • ethylene such as cotton or linen.
  • Especially good softening effects oxide advantageously at a raised temperature
  • the aqueous treating bath contains the described softentity of an alkali metal or alkali metal hydroxide, carbonate ing agents in such an amount that the treated fibers may or acetate. contain 008 to 1.2, preferably 0.1 to l or 0.15 to 0.8 pet-
  • the amount of additively combined ethylene oxide is cent of the softening agent.
  • the fibers may be treated critical.
  • Useful softening agents are obtained when 1 with the bath in the usual exhaust process or by the padmol of the acylamino-compound is reacted with about ding process. 8-30, advantageously about 15-20 mole of ethylene oxide.
  • polyacrylonitrile, poly- In general these products possess good resistance to heat ester, polyamide, or cellulose acetate fibers are to be and have little or no yellowing afiinity on the textile fibers treated, the bath contains 0.1-02 percent of the softening treated therewith.
  • the agent when applied to dyed material, the agent; in the case of cotton it contains about 0.2-0.4; and fastness to light of the dyeing is usually not impaired at in the case of wool fibers about 0.8-1.2 percent, calall or only to an inconsiderable extent.
  • the temperature of the treating bath may vary within anti-creasing treatment baths, so as to impart to the wide limits, for example, between 20 C. and 100 C. treated material an anti-crease resistant dressing and also As a rule, the fibers are treated at temperatures between a soft feel. 20 and 40 C. After the treating with the bath the fibers From the foregoing description it will be apparent that are dried, usually without previous rinsing, at temperaespecially valuable softening agents are the products of tures ranging from 20 to 160 C., preferably at elevated the formula temperatures i.e. at a temperature between 60 and 120 C. I I (PROD The following examples illustrate theinvention, the [$-OH2CHI-CH2CHZ1 ⁇ II]( A)5 parts and percentages being by weight:
  • Example 1 in which the radicals R are saturated aliphatic hydrocarbon radicals containing 1-17, preferably 11-17 carbon Defatted yarn of viscose artificial silk is Worked at a atoms and the radicals A corresponds to the formula liquor ratio of 1:30 for /2 hour at 20 C. in a solution,
  • p represents an integer from 1 to 2
  • k, r and s C. in the presence of about 1 percent of sodium calcueach represents an integer from 1 to 29, the sum of lated on the acylation product.
  • the polyglycol ether dek-l-r+s being at least 8 and at the most 30, and R R rivative is a soft mass which is easily soluble in water.
  • R each represent a saturated aliphatic hydrocarbon '(b) 92.7 parts (1 molecular proportion) of diethylradical containing 1 to 17 carbon atoms, at least two of ene triamine and 729 parts (3 molecular proportions) of these acyl radicals containing 12 to 18 carbon atoms each, commercial stearic acid are heated in a current of nitrothe treated fibers containing said compound in an amount gen at 140 C., and then the mixture is first heated for 3 of 008-12, preferably of 0.1-1 percent, calculated on hours at 140-l45 C. and thereafter for a further 4 /2 the Weight of the fibers, and drying the fibers at elevated hours at l60-l65 C. Nitrogen is continuously passed tempera-tures.
  • Example 2 100 parts of defatted yarn of viscose artificial silk are treated for /2 hour at 20 C. in a solution containing 0.3 part of the acetate (d) (50 percent amine content) described below in 3000 parts of distilled water. This treatment imparts a soft feel to the yarn.
  • the acetate of the condensation product (a) described above in Example 1 can be prepared by mixing 15 parts of the condensation product with 4.4 parts of acetic acid of 20 percent strength and 10.6 parts of water. In this manner there is obtained a paste having a calculated content of 50 percent of amine.
  • Example 3 100 parts of fibers of polyacrylonitrile are treated for 20-30 minutes at 20 C. in a solution containing 0.15 part of the softening agents (2), (f), (g) or (It) described below in 3000 parts of water. The fibers are dried, with out rinsing, at temperatures between 6080 C. This treatment imparts a soft feel to the yarn.
  • ethoxylation products are solid masses, which are almost clearly soluble in warm water.
  • Example 4 Fibers mentioned in the table below are worked at a liquor ratio of 1:30 for 1030 minutes at a temperature between 30-55 C. in a solution containing the indicated percentage of condensation product (0) of Example 1, calculated on the weight of the fibers.
  • the textile fibers are dried, without rinsing, at temperatures from 60-80 C.
  • Fiber Percent softening agent Polyacrylonitrile 0.15 Polyester 0.15 Polyamide 0.15 Cellulose-2 /2-acetate 0.15
  • a process for imparting a soft feel to organic textile fibers which comprises treating said fibers with an aqueous solution of a compound which in its free base state is a reaction product of 10-25 mols of ethylene oxide and 1 mol of an N-acylated alkylene polyamine which corresponds to the formula wherein n, p, q, k and m each represent an integer from 1 to 2, R R R and R each represent a saturated aliphatic hydrocarbon radical containing 1 to 17 carbon atoms, at least two of the acyl radicals containing 12 to 18 carbon atoms each, the treated fibers containing said reaction product in an amount of 0.08-12 percent, calculated on the weight of the fibers, and drying the fibers at elevated temperatures.
  • a process for imparting a soft feel to organic textile fibers which comprises treating said fibers with an aqueous solution of a compound which in its free base state is a reaction product of 1025 mols of ethylene oxide and 1 mol of an N-acylated alkylene polyamine which corresponds to the general formula wherein n, p and k each represent an integer from 1 to 2, R R and R each represent a saturated aliphatic hydrocarbon radical containing 1 to 17 carbon atoms and, at least two of the acyl radicals containing 12 to 18 carbon atoms, the treated fibers containing said reaction product in an amount of 0.081.2 percent, calculated on the weight of the fibers, and drying the fibers at elevated temperatures.
  • a process for imparting a soft feel to organic textile fibers which comprises treating said fibers with an aqueous solution of a compound which in its free base state is a reaction product of 1025 mols of ethylene oxide and 1 mol of an N-acylated alkylene polyamine which corresponds to the general formula wherein p represents an integer from 1 to 2, R R and R each represent a saturated aliphatic hydrocarbon radical containing 1 to 17 carbon atoms each, at least two of the acyl radicals containing 12 to 18 carbon atoms, the treated fibers containing said reaction product in an amount of 0.081.2 percent, calculated on the weight of the fibers, and drying the fibers at elevated temperatures.
  • a process for imparting a soft feel to organic textile fibers selected from the group consisting of animal fibers, cellulosic fibers and synthetic fibers which comprises treating said fibers with an aqueous solution of a compound which in its free base state is a reaction product of 10-25 mols of ethylene oxide and 1 mol of an N-acylated alkylene polyamine which corresponds to the general formula wherein R and R each represent a saturated aliphatic hydrocarbon radical containing 1117 carbon atoms, the treated fibers containing said reaction product in an amount of 0.081.2 percent, calculated on the weight of the fibers, and drying the fibers at elevated temperatures.
  • R R and R each represent a saturated aliphatic hydrocarbon radical containing 11-17 carbon atoms, the treated fibers containing said reaction product in an amount of 0.081.2 percent, calculated on the weight of the fibers, and drying the fibers at elevated temperatures.
  • a process for imparting a soft feel to organic textile fibers selected from the group consisting of animal fibers, cellulosic fibers and synthetic fibers which comprises treating said fibers with an aqueous solution of a compound which in its free base state is a reaction product of l025 mols of ethylene oxide and 1 mol of an N- acylated alkylene polyamine which corresponds to the formula the treated fibers containing said reaction product in an amount of 0.1-1 percent, calculated on the weight of the fibers, and drying the fibers at elevated temperatures.
  • a process for imparting a soft feel to organic textile fibers selected from the group consisting of animal fibers, cellulosic fibers and synthetic fibers which comprises treating said fibers with an aqueous solution of a compound which in its free base state is a reaction product of 10-25 mols of ethylene oxide and 1 mol of an N- acylated alkylene polyamine which corresponds to the formula the treated fibers containing said reaction product in an amount of 0.1-1 percent, calculated on the weight of the fibers, and drying the fibers at elevated temperatures.
  • a process for impatring a soft feel to cellulose triacetate fibers which comprises treating said fibers with an aqueous solution of a compound which in its free base state is a reaction product of 15 mols of ethylene oxide and 1 mol of an N-acylated alkylene polyamine which corresponds to the formula the treated fibers containing said reaction product in an amount of 0.1-1 percent, calculated on the weight of the fibers and drying the fibers at elevated temperatures.
  • a process for imparting a soft feel to cellulose triacetate fibers which comprises treating said fibers with an aqueous solution of a compound which in its free base state is a reaction product of 15 mols of ethylene oxide and 1 mol of an N-acylated alkylene polyamine which corresponds to the formula C17H35fi NHCH2CH2-1? CH2OH1 NH%-C"H35 0 O
  • 0 0 the treated fibers containing said reaction product in an amount of 0.l-1 percent, calculated on the weight of the fibers and drying the fibers at elevated temperatures.

Description

United States Patent 3,038,820 PROCESS FUR IMPARTING A SOFT FEEL Ti) TEXTILE FIBERS Otto Albrecht, Munchenstein, Switzerland, assignor t Ciba Limited, Basel, Switzerland N0 Drawing. Filed Mar. 23, 1959, Ser. No. $410,968 Claims priority, application Switzerland July 15, 1955 9 Claims. (Cl. 117-1395) The present application is a continuation-in-part of my application Serial No. 666,782, filed June 19, 1957, which is a division of my copending application Serial No. 596,444, filed July 9, 1956 (both of which applications are now abandoned).
This invention provides a new process for imparting a soft feel to organic textile fibers which comprises applying to said fibers in an aqueous bath a polyglycol ether derivative, in which each carbon atom bound to an oxygen atom is bound to a single oxygen atom, and which contains the radical of an amine of the formula 1 H N-Alkylene-ENH-AlkyleneH- NH in which in represents a small whole number, and in which there are bound to nitrogen atoms of the amine radical at least two acyl radicals together containing at least 20 carbon atoms and derived from fatty acid.
The aforesaid polyglycolether derivative can be made by introducing a polyglycol ether chain, advantageously with the aid of ethylene oxide, into an acyl-compound which is derived from an amine of the Formula 1 and contains at least two acyl radicals which are derived from fatty acids and together contain at least 20 carbon atoms, and in which acyl compound each carbon atom bound to an oxygen atom is bound to a single oxygen atom.
Particularly, this invention provides a process for imparting a soft feel to organic textile fibers which comprises treating said fibers with an aqueous bath which contains a compound which in its free base state is a reaction product of 8-30 mols of ethylene oxide and 1 mol of an N-acylated alkylene polyamine which contains 2 to 4 nitrogen atoms separated from each other by alkylene groups containing 2 to 3 carbon atoms, in which N-acylated alkylene polyamine at least 2 nitrogen atoms are acylated by a saturated aliphatic monocarboxylic acid containing 12 to 18 carbon atoms, and drying the fibers.
As starting materials for making the ethylene oxide reaction products there may be used, for example, amines of the kind defined above which are diacylated with fatty acids, advantageously acylamino-compounds of the formula I I "1 l](-O CR1)p in which the radicals R are saturated aliphatic hydrocarbon radicals containing 1-17 carbon atoms, 11 represents an integer from 1 to 2, m represents an integer from 1 to 3, p is an integer from 2 to 4 and is greater than m by at most 1, and the radicals CO--R together contain at least 20 carbon atoms.
More particularly, there may be used N-acylamino compounds corresponding to the general formula 3,038,820 Patented June 12, 1962 wherein n, p, q, k and In each represent an integer from 1 to 2, R R R and R each represent a saturated aliphatic hydrocarbon radical containing 1 to 7 carbon atoms, at least two of the acyl radicals containing 12 to 18 carbon atoms each.
The acyl-compounds are derived from aliphatic alkylene polyamines which contain 2 to 4 nitrogen atoms separated from each other by at least one divalent alkylene group containing 2 to 3 carbon atoms, preferably by at least one ethylene group, for example, from ethylene diamine, propylene diamine, diethylene triamine or triethylene tetramine. Especially advantageous are the acyl compounds of diethylene triamine. The acyl compounds derived from diethylene triamine correspond to the formula in which R represents a saturated aliphatic hydrocarbon radical containing 1 to 17, preferably 11-17, carbon atoms, 17 represents an integer from 2 to 3, and the acyl radicals OCR together contain at least 20 carbon atoms, at least 2 acyl radicals each containing at least 8 carbon atoms.
Still more particularly the acyl compounds derived from diethylene triamine correspond to the formula wherein 11 represents an integer from 1 to 2, R R and R each represent a saturated aliphatic hydrocarbon radical containing 1 to 17 carbon atoms, at least two of the acyl radicals containing 12 to 18 carbon atoms each.
The acyl compounds used as starting materials for making the polyglycol ether derivatives therefore contain at least two Nacyl radicals, the acyl radicals must together contain at least 20 carbon atoms, and it is generally advantageous that there should be present in the molecule at least two acyl radicals each containing at least 8 carbon atoms. Preferably there are used compounds containing the same number of acyl radicals as there are amino groups. These products are present when, for example, p in the Formula 4 is 3 and when p in the Formula 5 is 1.
The acyl radicals of the compounds of the Formulae 2, 3, 4 and 5 contain from 1 to 22, preferably from 12 to 18, carbon atoms. Accordingly, the acyl radicals are derived, for example, from advantageously unbranched saturated fatty acids of high molecular weight, such as lauric acid (for example, in the form of coconut oil fatty acid), myristic acid, palmitic acid, arachic acid or behenic acid. Especially advantageous are, for example, acyl compounds derived from stearic acid, and especially those of which the acyl radicals are those of so-called commercial stearic acid consisting for the greater part of stearic acid. It the acyl radicals are derived from fatty acids of low molecular weight they consist, for example, of an acetyl, propionyl or butyryl radical.
The acyl-compounds used as starting materials for mak- O m-l ing the polyglycol ether derivatives can be prepared in produced fibers to be subjected to the process of this inknown manner from the appropriate polyamines and carvention are those of polyacrylonitrile, polyesters, polyboxylic acids, or, if desired, functional derivatives of these amides or polyurethanes; chemically modified cellulosic acids, such as their acid halides, especially their acid fibers are those of cellulose acetate. or cellulose ether; chlorides, or acid anhydrides. When acyl radicals of low and regenerated cellulosic fibers are those of rayon. Bemolecular weight are introduced in addition to acyl radisides these synthetically produced or semi-synthetically cals of high molecular weight, it is of advantage to introproduced fibers there come into consideration animal duce the former acyl radicals last. fibers, such as wool or silk and natural cellulosic fibers,
The acylamino-compounds are reacted with ethylene such as cotton or linen. Especially good softening effects oxide advantageously at a raised temperature With the are obtained by treating fibers from polyacrylonitrile, exclusion of atmospheric oxygen and preferably in the polyamides, rayon and cellulose triacetate. presence of a suitable catalyst, for example, a small quan- The aqueous treating bath contains the described softentity of an alkali metal or alkali metal hydroxide, carbonate ing agents in such an amount that the treated fibers may or acetate. contain 008 to 1.2, preferably 0.1 to l or 0.15 to 0.8 pet- The amount of additively combined ethylene oxide is cent of the softening agent. The fibers may be treated critical. Useful softening agents are obtained when 1 with the bath in the usual exhaust process or by the padmol of the acylamino-compound is reacted with about ding process. 8-30, advantageously about 15-20 mole of ethylene oxide. When, in the exhaust process, polyacrylonitrile, poly- In general these products possess good resistance to heat ester, polyamide, or cellulose acetate fibers are to be and have little or no yellowing afiinity on the textile fibers treated, the bath contains 0.1-02 percent of the softening treated therewith. When applied to dyed material, the agent; in the case of cotton it contains about 0.2-0.4; and fastness to light of the dyeing is usually not impaired at in the case of wool fibers about 0.8-1.2 percent, calall or only to an inconsiderable extent. The polyglycol culated on the weight of the fibers.
ether compounds are very suitable for incorporation in The temperature of the treating bath may vary within anti-creasing treatment baths, so as to impart to the wide limits, for example, between 20 C. and 100 C. treated material an anti-crease resistant dressing and also As a rule, the fibers are treated at temperatures between a soft feel. 20 and 40 C. After the treating with the bath the fibers From the foregoing description it will be apparent that are dried, usually without previous rinsing, at temperaespecially valuable softening agents are the products of tures ranging from 20 to 160 C., preferably at elevated the formula temperatures i.e. at a temperature between 60 and 120 C. I I (PROD The following examples illustrate theinvention, the [$-OH2CHI-CH2CHZ1\II]( A)5 parts and percentages being by weight:
Example 1 in which the radicals R are saturated aliphatic hydrocarbon radicals containing 1-17, preferably 11-17 carbon Defatted yarn of viscose artificial silk is Worked at a atoms and the radicals A corresponds to the formula liquor ratio of 1:30 for /2 hour at 20 C. in a solution,
prepared with water of 20 German hardness and con- TCm-OH -O/ CHgCH2-OH taming 0.1 percent of the condensation product (a), (b)
or (c) described below, calculated on the weight of the Which k is a Wh01e P is all integfif from 2 yarn. After separating the excess of liquor and drying to 3, and the a a s 1 together contam at least the material, the yarn so treated has a soft slippery feel.
20 carbon atoms at least two of these radicals each con- (a) 103 parts (1 mol) of diethylene triamine are heattaining at least 8 carbon atoms, and the molecule of the d i a current of it t 140 C, under a descending product contains about 8-30 CH CH O- groups. condenser, and 540 parts (2 mols) of commercial ste- Still more particularly the invention provides a process aric acid are added in the course of 4 hours. The mixfor imparting soft feel to ganic textile fibers which ture is stirred for a further 4 hours in a current of nitrocomprises treating said fibers with an aqueous solution of gen at 160165 C. One molecular proportion of the a compound which in its free base state corresponds to condensation product so obtained is then reacted with the general formula 25 molecular proportions of ethylene oxide at ll0-130 R! R2 l: 0H OH 07 -0112011;0H1
wherein p represents an integer from 1 to 2, k, r and s C. in the presence of about 1 percent of sodium calcueach represents an integer from 1 to 29, the sum of lated on the acylation product. The polyglycol ether dek-l-r+s being at least 8 and at the most 30, and R R rivative is a soft mass which is easily soluble in water. and R each represent a saturated aliphatic hydrocarbon '(b) 92.7 parts (1 molecular proportion) of diethylradical containing 1 to 17 carbon atoms, at least two of ene triamine and 729 parts (3 molecular proportions) of these acyl radicals containing 12 to 18 carbon atoms each, commercial stearic acid are heated in a current of nitrothe treated fibers containing said compound in an amount gen at 140 C., and then the mixture is first heated for 3 of 008-12, preferably of 0.1-1 percent, calculated on hours at 140-l45 C. and thereafter for a further 4 /2 the Weight of the fibers, and drying the fibers at elevated hours at l60-l65 C. Nitrogen is continuously passed tempera-tures. through the apparatus. There are obtained 776 parts Those polyglycol ether derivatives which contain at of a pale Wax-like condensation product. least one basic nitrogen atom can be converted in known 60 parts 1 molecular proportion) of the reaction prodmanner into salts, for example, acetates, or, if desired, not so obtained are melted in a current of nitrogen, then into quaternary ammonium salts, and used in this form. 0.15 part of sodium is added, and ethylene oxide is in- In the process of the invention there are treated syntroduced as a finely distributed gas stream at ISO-160 thetically produced or chemically modified cellulosic C. until 92 parts (30 molecular proportions) of ethylene fibers or regenerated cellulosic fibers the manufacturing oxide have been taken up. The hydroxyethylation prodprocess of which has been completed. synthetically uct so obtained is a light colored solid mass, which yields an opalescent solution when taken up in warm water.
(0) 92.7 parts (1 molecular proportion) of diethylene triamine and 729 parts (3 molecular proportions) of commercial stearic acid are heated in a current of nitrogen to 140 C., and then the mixture is first heated for 3 hours at 140-145 C. and then for a further 4 /2 hours at 160-165 C. Nitrogen is continuously passed through the apparatus. There are obtained 776 parts of a pale wax-like condensation product.
60 parts (1 molecular proportion) of the reaction product so obtained are melted in a current of nitrogen, and then 0.15 part of sodium is added and ethylene oxide is introduced as a finely distributed gas stream at ISO-160 C. until 46 parts (15 molecular proportions) of ethylene oxide have been taken up. In this marner the hydroxyethylation product is obtained in the form of a light colored solid mass which when taken up in warm water yields an opalescent solution.
Example 2 100 parts of defatted yarn of viscose artificial silk are treated for /2 hour at 20 C. in a solution containing 0.3 part of the acetate (d) (50 percent amine content) described below in 3000 parts of distilled water. This treatment imparts a soft feel to the yarn.
A similar result is obtained by treating the yarn on a foulard with a solution containing 2.5 grams of the aforesaid acetate in one liter of water.
(d) The acetate of the condensation product (a) described above in Example 1 can be prepared by mixing 15 parts of the condensation product with 4.4 parts of acetic acid of 20 percent strength and 10.6 parts of water. In this manner there is obtained a paste having a calculated content of 50 percent of amine.
Example 3 100 parts of fibers of polyacrylonitrile are treated for 20-30 minutes at 20 C. in a solution containing 0.15 part of the softening agents (2), (f), (g) or (It) described below in 3000 parts of water. The fibers are dried, with out rinsing, at temperatures between 6080 C. This treatment imparts a soft feel to the yarn.
(e) 103 parts (1 mol) of diethylene triamine are heated to 140 C. in a current of nitrogen, and 540 parts (2 mols) of commercial stearic acid are added in small portions in the course of 4 hours. The whole is then stirred for a further 4 hours at 160-165 C. Throughout the reaction nitrogen is passed through the apparatus continuously in order to prevent discoloration as far as possible.
121.4 parts (1 molecular proportion) of the condensation product so obtained are melted in a boiling water bath and 22.4 parts (1 molecular proportion) of acetic anhydride are run in the course of one hour. The whole is then stirred for 2 hours in a boiling water bath. The reaction product is then treated with a dilute solution of sodium carbonate, taken up in an organic solvent, and then freed from solvent.
20 parts (1 molecular proportion) of the acylation product so obtained are melted in a current of nitrogen, 0.2 part of metallic sodium is added, and ethylene oxide is introduced in a finely distributed gas stream at 160 -.170 C. until 13.5 parts molecular proportions) of ethylene oxide have been absorbed. In another sample, 20 parts of the acylation product are reacted with 10.8 parts (8 molecular proportions) of ethylene oxide. The
ethoxylation products are solid masses, which are almost clearly soluble in warm water.
(f) Diethylene triamine is diacylated in commercial stearic acid as described in the first paragraph of Example 1. parts (1 molecular proportion) of the resulting distearyldiethylene triamine (from commercial stearic acid) are melted in a current of nitrogen, and then 0.8 part or" sodium is added and ethylene oxide is intro duced as a finely distributed gas stream until 180 parts (18 molecular proportions) thereof have been taken up. The condensation product, which is a rather soft mass, is soluble in water.
(g) 243 parts (3 molecular proportions) of commercial stearic acid are heated in a current of nitrogen until they melt, and 43.8 parts (1 molecular proportion) of triethylene tetramine are added to the melt having a temperature of about C. The reaction mass is then heated at l40-145 C. for 3 hours, and then at 160-165 C. for 4%. hours with stirring. During this time nitrogen is passed through the apparatus.
100 parts (1 molecular proportion) of the condensation product so obtained are heated to C. in a cur rent of nitrogen, whereupon ethylene oxide is introduced as a finely distributed gas stream until 109.4 parts (22 molecular proportions) are taken up. The resulting polyglycol ether derivative is a wax-like mass which is soluble in water.
(it) 74 parts of propylene diamine (1 mol) and 540 parts (2 mol) of commercial stearic acid are heated to 140 C. in a current of nitrogen, whereupon the reaction mass is heated first at l40145 C. for 3 hours and then at -165" C. for 4 hours. During this time, nitrogen is passed through the apparatus. 60 parts (1 molecular proportion) of the reaction product so obtained are melted in a current of nitrogen, and 0.15 part of sodium added, and at l50160 C. ethylene oxide is introduced as a finely distributed gas stream until 70 parts (15 molecular proportions) are taken up.
Example 4 Fibers mentioned in the table below are worked at a liquor ratio of 1:30 for 1030 minutes at a temperature between 30-55 C. in a solution containing the indicated percentage of condensation product (0) of Example 1, calculated on the weight of the fibers. The textile fibers are dried, without rinsing, at temperatures from 60-80 C.
Fiber: Percent softening agent Polyacrylonitrile 0.15 Polyester 0.15 Polyamide 0.15 Cellulose-2 /2-acetate 0.15
Cellulose-tri-acetate 0.15
Rayon 0.08 Cotton 0.3 Wool 1.2
Especially good softening results are obtained with fibers of cellulose-tri-acetate and also with fibers of polyacrylonitrile, polyamides and rayon.
What is claimed is:
1. A process for imparting a soft feel to organic textile fibers which comprises treating said fibers with an aqueous solution of a compound which in its free base state is a reaction product of 10-25 mols of ethylene oxide and 1 mol of an N-acylated alkylene polyamine which corresponds to the formula wherein n, p, q, k and m each represent an integer from 1 to 2, R R R and R each represent a saturated aliphatic hydrocarbon radical containing 1 to 17 carbon atoms, at least two of the acyl radicals containing 12 to 18 carbon atoms each, the treated fibers containing said reaction product in an amount of 0.08-12 percent, calculated on the weight of the fibers, and drying the fibers at elevated temperatures.
2. A process for imparting a soft feel to organic textile fibers which comprises treating said fibers with an aqueous solution of a compound which in its free base state is a reaction product of 1025 mols of ethylene oxide and 1 mol of an N-acylated alkylene polyamine which corresponds to the general formula wherein n, p and k each represent an integer from 1 to 2, R R and R each represent a saturated aliphatic hydrocarbon radical containing 1 to 17 carbon atoms and, at least two of the acyl radicals containing 12 to 18 carbon atoms, the treated fibers containing said reaction product in an amount of 0.081.2 percent, calculated on the weight of the fibers, and drying the fibers at elevated temperatures.
3. A process for imparting a soft feel to organic textile fibers which comprises treating said fibers with an aqueous solution of a compound which in its free base state is a reaction product of 1025 mols of ethylene oxide and 1 mol of an N-acylated alkylene polyamine which corresponds to the general formula wherein p represents an integer from 1 to 2, R R and R each represent a saturated aliphatic hydrocarbon radical containing 1 to 17 carbon atoms each, at least two of the acyl radicals containing 12 to 18 carbon atoms, the treated fibers containing said reaction product in an amount of 0.081.2 percent, calculated on the weight of the fibers, and drying the fibers at elevated temperatures.
4. A process for imparting a soft feel to organic textile fibers selected from the group consisting of animal fibers, cellulosic fibers and synthetic fibers which comprises treating said fibers with an aqueous solution of a compound which in its free base state is a reaction product of 10-25 mols of ethylene oxide and 1 mol of an N-acylated alkylene polyamine which corresponds to the general formula wherein R and R each represent a saturated aliphatic hydrocarbon radical containing 1117 carbon atoms, the treated fibers containing said reaction product in an amount of 0.081.2 percent, calculated on the weight of the fibers, and drying the fibers at elevated temperatures.
wherein R R and R each represent a saturated aliphatic hydrocarbon radical containing 11-17 carbon atoms, the treated fibers containing said reaction product in an amount of 0.081.2 percent, calculated on the weight of the fibers, and drying the fibers at elevated temperatures.
6. A process for imparting a soft feel to organic textile fibers selected from the group consisting of animal fibers, cellulosic fibers and synthetic fibers which comprises treating said fibers with an aqueous solution of a compound which in its free base state is a reaction product of l025 mols of ethylene oxide and 1 mol of an N- acylated alkylene polyamine which corresponds to the formula the treated fibers containing said reaction product in an amount of 0.1-1 percent, calculated on the weight of the fibers, and drying the fibers at elevated temperatures.
7. A process for imparting a soft feel to organic textile fibers selected from the group consisting of animal fibers, cellulosic fibers and synthetic fibers which comprises treating said fibers with an aqueous solution of a compound which in its free base state is a reaction product of 10-25 mols of ethylene oxide and 1 mol of an N- acylated alkylene polyamine which corresponds to the formula the treated fibers containing said reaction product in an amount of 0.1-1 percent, calculated on the weight of the fibers, and drying the fibers at elevated temperatures.
8. A process for impatring a soft feel to cellulose triacetate fibers which comprises treating said fibers with an aqueous solution of a compound which in its free base state is a reaction product of 15 mols of ethylene oxide and 1 mol of an N-acylated alkylene polyamine which corresponds to the formula the treated fibers containing said reaction product in an amount of 0.1-1 percent, calculated on the weight of the fibers and drying the fibers at elevated temperatures. 9. A process for imparting a soft feel to cellulose triacetate fibers which comprises treating said fibers with an aqueous solution of a compound which in its free base state is a reaction product of 15 mols of ethylene oxide and 1 mol of an N-acylated alkylene polyamine which corresponds to the formula C17H35fi NHCH2CH2-1? CH2OH1 NH%-C"H35 0 O|=0 0 the treated fibers containing said reaction product in an amount of 0.l-1 percent, calculated on the weight of the fibers and drying the fibers at elevated temperatures.
References Cited in the file of this patent UNITED STATES PATENTS 1,924,698 Neelmeier et al. Aug. 29, 1933 2,085,706 Schoeller et al June 29, 1937 2,103,872 Schoeller et al Dec. 28, 1937 2,201,041 Katz May 14, 1940 2,340,881 Kelly et al Feb. 8, 1944 2,596,985 Cook et a1. May 20, 1952 2,681,354 Kelly et al. June 15, 1954 2,901,430 Chiddix et al. Aug. 25, 1959

Claims (1)

1. A PROCES FOR IMPARTING A SOFT FEEL TO ORGANIC TEXTILE FIBERS WHICH COMPRISES TREATING SAID FIBERS WITH AN AQUEOUS SOLUTION OF A COMPOUND WHICH IN ITS FREE BASE STATE IS A REACTION PRODUCT OF 10-25 MOLS OF ETHYLENE OXIDE AND 1 MOL OF AN N-ACYLATED ALKYLENE POLYAMINE WHICH CORRESPONDS TO THE FORMULA
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US3257233A (en) * 1963-04-08 1966-06-21 Gen Mills Inc Textile fabric treated with ditertiary amine obtained from a secondary amine and polyoxyethylene glycol and the quaternary obtained therefrom
US3451844A (en) * 1965-01-20 1969-06-24 Bayer Ag Cationic active agent and a method for softening a washable textile fabric therewith
US3457213A (en) * 1967-05-04 1969-07-22 Du Pont Coapplication of softeners with an acid halide containing polymeric shrinkproofing agent to textile fibers
US4600606A (en) * 1979-04-18 1986-07-15 White Chemical Corporation Process for rendering non-thermoplastic fibrous materials flame resistant to molten materials by application thereto of a flame resistant composition, and related articles and compositions
US4623583A (en) * 1979-04-18 1986-11-18 White Chemical Corporation Flame retardant textile fabrics
WO1992007132A1 (en) * 1990-10-15 1992-04-30 Precision Processes Textiles Softening agents
US5133885A (en) * 1989-10-16 1992-07-28 Colgate-Palmolive Company New softening compositions and methods for making and using same
US5858023A (en) * 1990-10-15 1999-01-12 Precision Processes Textiles Softening agents

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US4161482A (en) * 1977-03-02 1979-07-17 The Indian Space Research Organisation Production of polyols containing basic nitrogen
DE3238395A1 (en) * 1982-10-16 1984-04-19 Henkel KGaA, 4000 Düsseldorf SMOOTHING AGENT FOR TEXTILE FIBER MATERIAL
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US3257233A (en) * 1963-04-08 1966-06-21 Gen Mills Inc Textile fabric treated with ditertiary amine obtained from a secondary amine and polyoxyethylene glycol and the quaternary obtained therefrom
US3451844A (en) * 1965-01-20 1969-06-24 Bayer Ag Cationic active agent and a method for softening a washable textile fabric therewith
US3457213A (en) * 1967-05-04 1969-07-22 Du Pont Coapplication of softeners with an acid halide containing polymeric shrinkproofing agent to textile fibers
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