US3554784A - Softening of textile materials - Google Patents

Softening of textile materials Download PDF

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US3554784A
US3554784A US643343A US3554784DA US3554784A US 3554784 A US3554784 A US 3554784A US 643343 A US643343 A US 643343A US 3554784D A US3554784D A US 3554784DA US 3554784 A US3554784 A US 3554784A
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oxide
bis
softening
softener
fabrics
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Warren I Lyness
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Procter and Gamble Co
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/53—Polyethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C309/07—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton
    • C07C309/12—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing esterified hydroxy groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C309/13—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
    • C07F9/5304—Acyclic saturated phosphine oxides or thioxides
    • 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
    • C08G65/2603—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 oxygen
    • C08G65/2606—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 oxygen containing hydroxyl groups
    • C08G65/2609—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 oxygen containing hydroxyl groups containing aliphatic hydroxyl groups
    • 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
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
    • C08G65/326—Polymers modified by chemical after-treatment with inorganic compounds containing sulfur
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/29—Sulfates of polyoxyalkylene ethers
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/001—Softening compositions
    • C11D3/0015—Softening compositions liquid
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/34—Organic compounds containing sulfur
    • C11D3/3472—Organic compounds containing sulfur additionally containing -COOH groups or derivatives thereof
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
    • D06L4/60—Optical bleaching or brightening
    • D06L4/657—Optical bleaching or brightening combined with other treatments, e.g. finishing, bleaching, softening, dyeing or pigment printing
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
    • D06L4/60—Optical bleaching or brightening
    • D06L4/664—Preparations of optical brighteners; Optical brighteners in aerosol form; Physical treatment of optical brighteners
    • 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
    • D06M13/244—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 sulfur or phosphorus
    • D06M13/248—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 sulfur or phosphorus with compounds containing sulfur
    • 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
    • D06M13/244—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 sulfur or phosphorus
    • D06M13/248—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 sulfur or phosphorus with compounds containing sulfur
    • D06M13/256—Sulfonated compounds esters thereof, e.g. sultones
    • 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
    • D06M13/244—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 sulfur or phosphorus
    • D06M13/248—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 sulfur or phosphorus with compounds containing sulfur
    • D06M13/262—Sulfated compounds thiosulfates
    • 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
    • D06M13/244—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 sulfur or phosphorus
    • D06M13/282—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 sulfur or phosphorus with compounds containing phosphorus
    • D06M13/285—Phosphines; Phosphine oxides; Phosphine sulfides; Phosphinic or phosphinous acids or derivatives thereof
    • 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
    • D06M13/325—Amines
    • D06M13/342—Amino-carboxylic acids; Betaines; Aminosulfonic acids; Sulfo-betaines
    • 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
    • D06M13/388—Amine oxides
    • 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

Definitions

  • This invention relates to the treatment of textile materials and, more particularly, it concerns a process for softening textile materials in a repetitious but generally discontinuous cycle which involves soiling, laundering, rinsing, soiling, etc.
  • softening agents to improve softness or hand of textile materials is well known. Aside from imparting softness, the treatment of textile materials with softening agents generally prevents the accumulation of static electric charges and makes the ironing of such materials easier. Only in the past two decades have softening agents become generally known by the housewife. Prior to this time, soap residues provided the same effect of improved hand or softness. With the advent of synthetic detergents which effectively remove fatty residues from the textile material, this benefit disappeared.
  • Synthetic detergents are generally used in conjunction with builder materials such as alkali metal carbonates, silicates and/or phosphates. These so-called builder materials tend to react with the metal ions present in the wash liquor, precipitating out salts which deposit on the fibers of the textile material being laundered. Deposited mineral salts weaken the laundered fabrics, particularly at those points where the fabric is exposed to friction and creasing such as at the collar and cuffs. It has been found that treatment of these laundered textiles with softening agents not only soften the textiles, but also prolong their useful life.
  • builder materials such as alkali metal carbonates, silicates and/or phosphates.
  • softening agents Most of the softening agents presently used in home laundry situations are cationic surface active agents having at least one long alkyl radical usually containing from 16 to 18 carbon atoms. These softening compounds are not compatible with anionic synthetic detergents which are used in most heavy-duty detergents and, thus, are employed only during the rinse cycle. After a Wash cycle in which an anionic synthetic detergent is used, variable amounts of such detergent compound remain on the textile. This residual anionic detergent compound will react, during the rinse cycle, with any cationic soften- .ing additive causing precipitation and, thus, inactivation .of'the softener. Any interaction between the detergent compound and softener makes it difficult to achieve a uniform desirable degree of softening. Additionally, this interaction can result in a degree of deposition on the ,textile, material which causes waterproofing and reduced absorbency.
  • cationic softening agents Another disagreeable feature of cationic softening agents is that those which have adsorbed to the softened textile can interact upon subsequent laundering with an Due to yellowing associated with the use of cationic softeners and the discoloration which inherently develops in cotton fabrics on aging, it is desirable to add a brightening agent to softener formulations. "These brighteners counteract the yellow hue of the fabric by giving off a blue-white fluorescence. Addition of brighteners to textile softener formulations intended for household use is common. Such brightener/softener formulations are greatly preferred by the average housewife.
  • R-IL 0 a textile softene having the formula R-IL 0 wherein R is a straight or branched carbon chain containing 20 to 30 carbon atoms selected from the group consisting of alkyl and alkenyl groups and wherein said alkyl and alkenyl groups contain 0-2 hydroxyl substituents, 0-5 ether linkages, 0-2 chlorine atoms and 0-1 amide linkage, R is an alkyl group containing from 1 to 20 carbon atoms and wherein said alkyl group contains 0-2 hydroxyl substituents, 0-5 ether linkages, 0-2 chlorine atoms and 0-1 amide linkage, and R is an alkyl group containing 1 to 3 carbon atoms selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, 2-hydroxyethyl and 2-hydroxypropyl, and wherein R and R can be joined to form a heterocyclic group containing 4 to 6 hydrocarbon
  • the softening agents described above can be added, alone i'o'rgin combination, in small amounts to the usual rinsing 'b tli. Where the softening agents are so added, it is'prefe ed that the rinse solution, contain from aboutl0 .00l%, ⁇ to
  • the rinse solution should contain from about 0.002% to about 0.01% softening agent by weight.
  • the softening agents described above can be used, alone or in combination, for treatment of textile materials in mill operation, as for example by padding on.
  • the fabrics are dipped into an equeous dispersion of from about 0.05% to about 2% by weight of the softening agents of this invention; preferably from about 0.2% to about 1%.
  • excess liquid is squeezed out between a pair of rolls.
  • the fabric is then dried, whereupon the softening agent which is entrained in the wet fabric remains on the fabric.
  • the agents demonstrate many advantages not obtainable with the cationic softening agents.
  • the softening agents of the present invention do not interact with anionic detergents and are easily removed by subsequent laundering. Therefore they do not cause waterproofing or bulidup of hydrophobic material on the treated textile material.
  • Softening agents of this invention which are preferably employed, alone or in combination, in the process of this invention are generically described as follows:
  • R is a straight or branched carbon chain containing 20 to 26 carbon atoms selected from the group consisting of alkyl and alkenyl groups and wherein said alkyl and alkenyl groups contain -2 hydroxyl substituents, and R and R are alkyl groups containing 1 to 3 carbon atoms selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, 2-hydroxyethyl and 2-hydroxypropyl.
  • softening agents which can be used most effectively in the process of this invention, alone or in combination, are as follows:
  • Examples of other preferred softening agents which can suitably be employed in the process of the present invention, alone or in combination are as follows: fl-hydroxyeicosyldimethylamine oxide Eicosylmethylethylamine oxide Eicosyldiethylamine oxide 2-eicosyldiethylamine oxide Heneicosyldimethylamine oxide Heneicosyldiethylamine oxide 6-docosylmethylethylamine oxide Docosyldiethylamine oxide Tricosyldimethylamine oxide Tricosyldiethylamine oxide Tetracosylmethylethylamine oxide 12-tetracosyldimethylamine oxide Tetracosyldiethylamine oxide B-hydroxytetracosyldimethylamine oxide Pentacosyldimethylamine oxide Pentacosyldiethylamine oxide Hexacosyldiethylamine oxide.
  • the textiles which are to be softened are laundered prior to being treated with the softening agents described above.
  • softening agents as Well as additives such as stabilizers can be used in conjunction with the softening agents employed in the process of this invention.
  • softeners which may be employed in combination with the softening agents of this invention appear in Chwala, Textilosstoff, Vienna 1939, particularly pages 61 to 64, March An Introduction to Textile Finishing, London, 1948, particularly Chapter X, and Schwartz-Perry, Surface Active Agents, New York, 1949, particularly pages 435 to 437.
  • Softening agents which may be used in conjunction with the softening agents of the present invention are characterized as follows: Ester, etheror amide-like condensation products containing polyalcohol, polyglycol, or polyglycerol radicals and suitable higher molecular, preferably long-chain aliphatic radicals with 12 to 18 carbon atoms, such as for instance fatty acid or fatty alcohol condensation products of the general formula R(C H O)NH wherein R stands for the monovalent radical of an aliphatic alcohol or an aliphatic acid or amide with 12 to 18 .cgu ooocn cu cn so m acylated or alkylated'alkyl polyamines and higher alkylolaniinesyandquaternary ammonium compounds such as 'cetylpyridinium chloride, cetyltrimethylammonium bromide and tetradecyldimethylbenzylammonium chloride, and mono-or polyester of long-chain fatty acids with monoor polyoxyamines
  • Examples'of'brightener compounds which may be used in conjunction with. the softening agents of the present invention include those disclosed in Stensby, Optical Brighteners in Fabric Softeners, Soap Chem. Specialties, 41, No. 5, 858 (May 1965), Netherland Pat. 6,408,162 (Jan. 18, 1965), U.S. Pat. 2,950,253 (Aug. 23, 1960) and Kirk et al., Optical Brighteners, Encyclopedia Chem. Tech. 3, 737-50 (1964).
  • *Other brightener compounds which can be used are those which are especially suitable for brightening synthetic fibers.
  • these brighteners include the bis-azoles such as 1,2-bis(-methyl-2-benzoxazolyl)ethylene, bis(S-methyl-Z-benzoxazolyl)thiophene and N-hydrox yethyl 1,2-bis(benzimidazoly1) ethylene; monoazole types such as 2- (m-chlorostyryl) -naphth- 1,2-d] -oxazole and 2-styryl-benzoxazole; the pyrazoline type such as l-psulfo'namidophenyl-3 -p-chlorophenyl 2 pyrazoline; and
  • the coumarin type such as 4-methyl-7-dimethylaminocoumarin and 3-phenyl-7-(diamino-sym-triazinylamino) coumarin.
  • Non-expert panels of ten persons were employed. Each panel member was presented with four pairs of cloth swatches. The panelists were asked to handle each pair of swatches in turn and select the softer of the two cloths if a difference could be discerned. Two pairs of test swatches were comprised of the treated cloth and the control cloth presented in such a way that the treated cloth was handled first in one case and the control cloth in the other. The other two pairs of test swatches were comprised of control cloths exclusively and were designed to serve as a bench-mark for random selection between cloths of identical character. The order of presentation of pairs to the panelists was varied from person to person.
  • Sets of fabrics comprised by four pairs of swatches were handled by no more than two persons each to avoid spurious results arising from pickup of skin oils, etc.
  • the test swatches were coded in such a way that the panelist was unable to distinguish whether a particular cloth had been softened.
  • the sets .of test swatches the number of panelists expressing a preference for the treated fabric was obtained and compared to the number of panelists unable to distinguish the test fabric from the control fabric.
  • EXAMPLE IV This example shows the ability of the amine oxide softener to be essentially completely removed by a single wash in-a typical heavy-duty anionic detergent formulation. This very desirable feature thus prevents the buildup "of the"softener on the fabric with consequent waterproofin'gand yellowing of the fabric due to breakdown of the quaternary ammonium compound.
  • the fabrics were 'fsoft'e ried as before (Procedures A and C), then washed i'n a nautomatic washer with anionic detergent for'mulationone-o'r more times. The fabrics were present'e' the panel members both after application of the "'s'oftenerand after each subsequent wash to determine the softness impression.
  • EXAMPLE v This example shows that the cloths softened with the amine oxide softeners having an alkyl radical of greater than 20 carbon atoms are such more absorbent than those which have been treated, with the quaternary ammonium salts which are ordinarily used.
  • the cloths were exposed to 50 partsper million of the softener compounds in the usual way (Procedures A and C), washed in a standard anionic heavy-duty detergent formulation, then reexposed to 50 parts per million of softener in the rinse cycle. Washing and application of softener were repeated through a total of four cycles of softener application.
  • brightener compounds which can be used are those which are especially suitable for brightening synthetic fibers.
  • these brighters include 1,2'-bis (5 methyI-Z-benzoxazolyl)ethylene, bis(5 methyl 2- benzoxolyl)thiophene and N hydroxyethyl 1,2 bis (benzimidazolyl)ethylene, 2 (m chlorostyryl-naptho- [l,2-d]oxazole and Z-styryl-benzoxazole; l p sulfonamidophenyl-3-p-chlorophenyl 2 pyrazoline; 4 methyl- 7-dimethylaminocoumarin and 3-phenyl-7-(diamino-symtriazinylamino coumarin.
  • EXAMPLE VII Sufficient docosyldimethylamine oxide to produce a level of 50 parts per million or 0.005% by weight of solution is introduced into the final the final rinse solution of a stnadard home automatic washing machine containing a load of mixed cotton fabrics from normal family usage. After completion of the rinse cycle, that is, exposure for about 5 minutes and then spin drying, the load is dried in an automatic dryer. Upon panel grading essentially like that of Procedure C, the fabrics are judged to be much softer and more desirable than fabrics which have not been treated with the amine oxide.
  • Example VIII When the conditions of Example VII are repeated using a mixed family load containing fine fabrics such as nylon and polyester and using a 50-50 mixture of eicosyldimethylamine oxide and docosyldimethylamine oxide it is seen that the fine fabrics are rendered largely antistatic and are much more desirable when worn than are the control fine fabrics which are not given a treatment with the amine oxide compound.
  • EXAMPLE IX This example shows the usefulness of a 50-50 mixture of eicosyldimethylamine oxide and docosyldimethylamine oxide when used in a padding-on process.
  • Test swatches of terry cloth treated in accordance with Procedure A are completely submerged in an aqueous dispersion containing 0.7% of the softening mixture by weight.
  • the cloth load comprised about 2% of the aqueous bath by weight.
  • the test cloths are exposed to the foregoing dispersion of softening agents for a period of about seconds.
  • the test cloths are then removed and passed between rubber rolls forcing out excess solution.
  • the weight of the test cloths at this point is about 3 times their original dry weight.
  • the test cloths are then dried in a standard automatic drier. Upon panel grading similar to that described in Procedure C, it is judged that the dried test cloths are much softer to the touch and fuller in appearance than in the absence of treatment with the foregoing mixture.
  • the process of treating textile materials which comprises the steps of: first, laundering with a detergent, and second, rinsing with an aqueous solution or dispersion consisting essentially of (A) from 0.001% to about 2.0% of a textile softener having the formula wherein R is a straight or branched carbon chain of about 22 carbon atoms selected from the group consisting of alkyl and alkenyl groups, R is an alkyl group containing from 1 to 20 carbon atoms and wherein said alkyl group contains not more than 2 hydroxyl substituents, not more than 5 ether linkages, not more than 2 chlorine atoms and not more than 1 amide linkage, and R is an alkyl group containing 1 to 3 carbon atoms selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, 2-hydroxyethyl and 2-hydroxypropyl, and wherein R and R can be joined to form a heterocyclic group containing 4
  • component (A) is docosyldimethylamine oxide.
  • component (A) is docosyl-bis-(fi-hydroxyethyl) amine oxide.
  • the aqueous solution contains from about 0.0001% to about 0.001% by weight of a brightening agent selected from the group consisting of 4,4 bis[4 anilino-6-di(hydroxyethyl)amino symtriazin-2-ylamino] 2,2 stilbenedisulfonic acid, disodium, 4,4-bis(4-anilino-6-morpholino sym triazin 2 ylamino) 2,2 stilbenedisulfonate, disodium 4,4 bis(4, 6-dianilino sym triazin 2 ylamino) 2,2 stilbenedisulfonate, disodium 4,4 bis(4 anilino-6-ethylaminosym triazin 2 ylamino) 2,2 stilbenedisulfonate, disodium, 4,4 bis(4 anilino 6 N methylethanolamino sym triazin 2 ylamino) 2,2 stilbenedisulfonic acid, dis

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Abstract

A PROCESS FOR SOFTENING TEXTILES IN AQUEOUS SOLUTION WITH CRITICAL AMOUNTS OF TRIALKYLAMINE OXIDE HAVING ONE ALKYL CHAIN CONTAINING AT LEAST 20 CARBON ATOMS.

Description

United States Patent US. Cl. 117-47 9 Claims ABSTRACT OF THE DISCLOSURE A process for softening textiles in aqueous solution with critical amounts of trialkylamine oxide having one alkyl chain containing at least 20 carbon atoms.
BACKGROUND OF INVENTION (1) Field of invention This invention relates to the treatment of textile materials and, more particularly, it concerns a process for softening textile materials in a repetitious but generally discontinuous cycle which involves soiling, laundering, rinsing, soiling, etc.
The use of softening agents to improve softness or hand of textile materials is well known. Aside from imparting softness, the treatment of textile materials with softening agents generally prevents the accumulation of static electric charges and makes the ironing of such materials easier. Only in the past two decades have softening agents become generally known by the housewife. Prior to this time, soap residues provided the same effect of improved hand or softness. With the advent of synthetic detergents which effectively remove fatty residues from the textile material, this benefit disappeared.
Synthetic detergents are generally used in conjunction with builder materials such as alkali metal carbonates, silicates and/or phosphates. These so-called builder materials tend to react with the metal ions present in the wash liquor, precipitating out salts which deposit on the fibers of the textile material being laundered. Deposited mineral salts weaken the laundered fabrics, particularly at those points where the fabric is exposed to friction and creasing such as at the collar and cuffs. It has been found that treatment of these laundered textiles with softening agents not only soften the textiles, but also prolong their useful life.
Most of the softening agents presently used in home laundry situations are cationic surface active agents having at least one long alkyl radical usually containing from 16 to 18 carbon atoms. These softening compounds are not compatible with anionic synthetic detergents which are used in most heavy-duty detergents and, thus, are employed only during the rinse cycle. After a Wash cycle in which an anionic synthetic detergent is used, variable amounts of such detergent compound remain on the textile. This residual anionic detergent compound will react, during the rinse cycle, with any cationic soften- .ing additive causing precipitation and, thus, inactivation .of'the softener. Any interaction between the detergent compound and softener makes it difficult to achieve a uniform desirable degree of softening. Additionally, this interaction can result in a degree of deposition on the ,textile, material which causes waterproofing and reduced absorbency.
' Another disagreeable feature of cationic softening agents is that those which have adsorbed to the softened textile can interact upon subsequent laundering with an Due to yellowing associated with the use of cationic softeners and the discoloration which inherently develops in cotton fabrics on aging, it is desirable to add a brightening agent to softener formulations. "These brighteners counteract the yellow hue of the fabric by giving off a blue-white fluorescence. Addition of brighteners to textile softener formulations intended for household use is common. Such brightener/softener formulations are greatly preferred by the average housewife.
The best and most commonly used brighteners, however, are inefficicnt when used in conjunction with cationic softeners. The reasons for this are not entirely understood, but it has been shown that the brightness conferred to cotton by a given amount of brightener when used in conjunction with a cationic softener is only onequarter to one-third as much as that given by the same amount of brightener when it is applied to the cloth from an anionic detergent formulation or from distilled water. Since brightener compounds are extremely expensive, a softener formulation which permits more eflicient brightener usage is highly desirable.
Another problem encountered in using the common cotton brighteners in softener formulations is that there is an upper limit to the amount of brightener which can be incorporated into such a formulation. This severely limits the degree of brightening which can be conferred to the cloth by cationic softener formulations.
(2) Description of the prior art The lower homologs of the softening agents which have been found to be useful in the process of the present invention are well known as synthetic detergent compounds being disclosed in the following patents: See US. Pat. 3,007,784 (Nov. 7, 1961), US. Pat. 3,047,579 (July 3, 1962) and US. Pat. 3,252,979 (May 24, 1966). There is nothing in the art that indicates that the higher homologs of these detergent compounds would have softening characteristics.
SUMMARY OF INVENTION It has been discovered that excellent results can be obtained by employing a softening process comprising the step of treating textile materials, which have been previously laundered with a synthetic detergent, with an aqueous solution consisting'essentially of:
(a) from 0.001% to about 2.0% of a textile softene having the formula R-IL 0 wherein R is a straight or branched carbon chain containing 20 to 30 carbon atoms selected from the group consisting of alkyl and alkenyl groups and wherein said alkyl and alkenyl groups contain 0-2 hydroxyl substituents, 0-5 ether linkages, 0-2 chlorine atoms and 0-1 amide linkage, R is an alkyl group containing from 1 to 20 carbon atoms and wherein said alkyl group contains 0-2 hydroxyl substituents, 0-5 ether linkages, 0-2 chlorine atoms and 0-1 amide linkage, and R is an alkyl group containing 1 to 3 carbon atoms selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, 2-hydroxyethyl and 2-hydroxypropyl, and wherein R and R can be joined to form a heterocyclic group containing 4 to 6 hydrocarbon groups, and p (b) the balance being water, all percentages. being weight. I
As an embodiment of the present invention, the softening agents described above can be added, alone i'o'rgin combination, in small amounts to the usual rinsing 'b tli. Where the softening agents are so added, it is'prefe ed that the rinse solution, contain from aboutl0 .00l%, }to
about 0.05% softening agent by weight. For best softening results, it is preferred that the rinse solution should contain from about 0.002% to about 0.01% softening agent by weight.
As another embodiment of the present invention, the softening agents described above can be used, alone or in combination, for treatment of textile materials in mill operation, as for example by padding on. In such processes, the fabrics are dipped into an equeous dispersion of from about 0.05% to about 2% by weight of the softening agents of this invention; preferably from about 0.2% to about 1%. As the fabric emerges from the aqueous dispersion, excess liquid is squeezed out between a pair of rolls. The fabric is then dried, whereupon the softening agent which is entrained in the wet fabric remains on the fabric.
It has been discovered that when filaments, fibers, threads, skeins, hanks, yarns, woven fabrics, etc., either synthetic as nylon, acrylics and polyesters or cellulosic such as cotton, viscose rayon, cuprammonium rayon and cellulose acetate and like materials, are treated with aqueous solutions or dispersions containing small amounts of the softening agents of this invention, they are softened to a marked degree and in general the useful life of the material is prolonged. It has also been discovered that when non-woven fabrics and papers, e.g., tissues, napkins, and paper towels, are treated with small amounts of the softening agents of this invention that they also become softened to a marked degree.
Besides the softening properties demonstrated by the softening agents of the present invention, the agents demonstrate many advantages not obtainable with the cationic softening agents. The softening agents of the present invention do not interact with anionic detergents and are easily removed by subsequent laundering. Therefore they do not cause waterproofing or bulidup of hydrophobic material on the treated textile material.
It has been discovered that formulations containing brightener compounds and the softening agents of the present invention effectively brighten fabrics whereas corresponding cationic softener formulations containing brighteners at the same level do not effectively brighten. Using the softening agents of the present invention, it has also been found that the brightening level is not limited as it is in cationic softening brightener formulations.
Softening agents of this invention which are preferably employed, alone or in combination, in the process of this invention are generically described as follows:
wherein R is a straight or branched carbon chain containing 20 to 26 carbon atoms selected from the group consisting of alkyl and alkenyl groups and wherein said alkyl and alkenyl groups contain -2 hydroxyl substituents, and R and R are alkyl groups containing 1 to 3 carbon atoms selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, 2-hydroxyethyl and 2-hydroxypropyl.
Specific examples of the softening agents which can be used most effectively in the process of this invention, alone or in combination, are as follows:
Eicosyl-bis-(B-hydrOXyethyDamine oxide Eicosyldimethylamine oxide Eicosyldiethylamine oxide Docosyldimethylamine oxide Docosyldiethylamine oxide Docosyl-bis-(fi-hydroxyethyl)amine oxide Tetracosyldimethylamine oxide "Ietracosyl-bis (fi-hydroxycthyl amine oxide Hexacosyldimethylamine oxide Hexacosyl-bis (,B-hydroxyethyl) amine oxide.
4 Examples of other preferred softening agents which can suitably be employed in the process of the present invention, alone or in combination are as follows: fl-hydroxyeicosyldimethylamine oxide Eicosylmethylethylamine oxide Eicosyldiethylamine oxide 2-eicosyldiethylamine oxide Heneicosyldimethylamine oxide Heneicosyldiethylamine oxide 6-docosylmethylethylamine oxide Docosyldiethylamine oxide Tricosyldimethylamine oxide Tricosyldiethylamine oxide Tetracosylmethylethylamine oxide 12-tetracosyldimethylamine oxide Tetracosyldiethylamine oxide B-hydroxytetracosyldimethylamine oxide Pentacosyldimethylamine oxide Pentacosyldiethylamine oxide Hexacosyldiethylamine oxide.
Examples of other softening agents which are useful in the process of this invention, alone or in combination, are as follows:
fl-Methoxydocosyldimethylamine oxide ,H-Chlorotricosyldimethylamine oxide Heptacosyldimethylamine oxide Heptacosyldiethylamine oxide Octacosyldimethylamine oxide Octacosylmethylethylamine oxide Octacosyl-bisfi-hydroxyethyl amine oxide Octacosyldiethylamine oxide Nonacosyldimethylamine oxide Nonacosyldiethylamine oxide Triacontyldimethylamine oxide Triacontyldiethylamine oxide 3,5-dioxatetracosyldimethylamine oxide 2-hydroxy-4-oxatetracosyldimethylamine oxide N-eicosylmorpholine-N-oxide 'N-docosylmorpholine-N-oxide 6-stearamidohexyldirnethylamine oxide B-Behenamindoethyldimethylamine oxide Behenylglyceryl (fl-hydroxyethyl methylamine oxide N-docosylpyrrolidine-N-oxide N-eicosylpiperidine-N-oxide N-tetracosylpyridine-N-oxide.
In the practice of the process of the present invention the textiles which are to be softened are laundered prior to being treated with the softening agents described above.
A list of synthetic detergents and builders which can be used to formulate detergent compositions useful in laundering these textile materials are disclosed in U.S. Pats. 3,159,581 (Dec. 19, 1964), col. 3, line 70 to col. 5, line 60 and 3,235,506 (Feb. 15, 1966), e.g. col. 3, line 40 to col. 4, line 54.
Other types of softening agents as Well as additives such as stabilizers can be used in conjunction with the softening agents employed in the process of this invention. Examples of other softeners which may be employed in combination with the softening agents of this invention appear in Chwala, Textilhilfsmittel, Vienna 1939, particularly pages 61 to 64, March An Introduction to Textile Finishing, London, 1948, particularly Chapter X, and Schwartz-Perry, Surface Active Agents, New York, 1949, particularly pages 435 to 437. Other softening agents which may be used in conjunction with the softening agents of the present invention are characterized as follows: Ester, etheror amide-like condensation products containing polyalcohol, polyglycol, or polyglycerol radicals and suitable higher molecular, preferably long-chain aliphatic radicals with 12 to 18 carbon atoms, such as for instance fatty acid or fatty alcohol condensation products of the general formula R(C H O)NH wherein R stands for the monovalent radical of an aliphatic alcohol or an aliphatic acid or amide with 12 to 18 .cgu ooocn cu cn so m acylated or alkylated'alkyl polyamines and higher alkylolaniinesyandquaternary ammonium compounds such as 'cetylpyridinium chloride, cetyltrimethylammonium bromide and tetradecyldimethylbenzylammonium chloride, and mono-or polyester of long-chain fatty acids with monoor polyoxyamines.
Examples'of'brightener compounds which may be used in conjunction with. the softening agents of the present invention include those disclosed in Stensby, Optical Brighteners in Fabric Softeners, Soap Chem. Specialties, 41, No. 5, 858 (May 1965), Netherland Pat. 6,408,162 (Jan. 18, 1965), U.S. Pat. 2,950,253 (Aug. 23, 1960) and Kirk et al., Optical Brighteners, Encyclopedia Chem. Tech. 3, 737-50 (1964). Specific examples of brightener -=compounds are cotton brighteners of the bis-triazinylstil bene type" such as 4,4'-bis-[4-anilino-6-di(hydroxyethyl)amino sym triazin-2-ylamino]-2,2-stilbenedisulfonic acid, disodium 4,4'-bis(4-anilino-6-morpholino-symtriazin 2 ylamino)-2,2-stilbenedisulfonate, disodium 4,4'-bis-(4,6 dianilino sym-triazin-Z-ylamino)-2,2-stilbenedisulfonate, disodium 4,4-bis(4-ani1ino-6-ethylaminosym-triazin 2 ylamino)-2,2-stilbenedisulfonate and disodium 4,4 bis(4 anilino-6-N-methylethanolaminosym triazin-2 ylamino)-2,2-stilbenedisulfonate; the his- N-a'cylstilbene type such as bis-benzoy1-, bis-p-aminobenzoyl and bis-dimethoxybenzoyl-derivatives of 4,4-diaminostilbene-2,2-disulfonic acids; the stilbene-triazole type such as s'odium-4-(2H-naphtho[1,2-d]triazol-2-yl)-2-stilbenes'ulfon'ate; and the dibenzothiophenedioxide type such as 3,7 bis(p-methoxybenzoylamido)-dibenzothiophene- 2,8-disulfonic acid-5,5-dioxide.
*Other brightener compounds which can be used are those which are especially suitable for brightening synthetic fibers. Examples of these brighteners include the bis-azoles such as 1,2-bis(-methyl-2-benzoxazolyl)ethylene, bis(S-methyl-Z-benzoxazolyl)thiophene and N-hydrox yethyl 1,2-bis(benzimidazoly1) ethylene; monoazole types such as 2- (m-chlorostyryl) -naphth- 1,2-d] -oxazole and 2-styryl-benzoxazole; the pyrazoline type such as l-psulfo'namidophenyl-3 -p-chlorophenyl 2 pyrazoline; and
the coumarin type such as 4-methyl-7-dimethylaminocoumarin and 3-phenyl-7-(diamino-sym-triazinylamino) coumarin.
When-the foregoing brightening agents are employed in the processes of the present invention, it has been found that good results are obtained when the brightener is present in the rinse solution in the amount of about .0001% to about 0.001% by weight of the solution and most preferably from about .0002% to about 0.005% by weight. Generally, these brightening agents are used in combination for'best brightening results.
1 .The softening. agents of this invention were found ,to be surprisingly more effective as softening agents than their lower homologs. The reason for this unexpected TESTING PROCEDURES (A) Preparation of test clothes.This method was used to prepare the fabrics used in Examples I-VIII. Commercial fabrics of the following specifications were used:
(1) Terry cloth (Style 1313 washclothes from Cannon);
(2) Crash cloth (Style 1035, 18" width bolts from Standard Textile Company); and
(3) Muslin cloth (Style 400 obtained from Test Fabrics Incorporated, N.Y.).
These cloths were de-sized and washed twice with a typical heavy-duty built anionic detergent composition in a standard automatic washing machine, and then rinsed four times in water (20 parts water per 1 part of cloth). Thereafter the cloths were dried and equilibrated at 45% relative humidity at 70 F. for two weeks before use. Pieces of cloth 5" square were cut for use in the softness testing, in determination of adsorption of softeners, and in determination of minimum levels of the compounds required for softening. Full size washcloths of the above description were used when additional testing of softness was desired. All cloths were discarded after the test results had been obtained.
(B) Adsorption studies.-Five gram swatches of cloth were exposed with moderate stirring for ten minutes to ml. of an aqueous solution containing the softener at the appropriate concentration. After ten minutes the solution was separated from the fabrics by decantation and the concentration of unadsorbed softener remaining in the solution was determined by titration with a standard solution of sodium alkylbenzenesulfonate. The amount of softener adsorbed from the solution by the fabric was determined by comparing the amount of softener found in the solution after exposure to the cloth with that present in the solution initially.
(C) Determination of softener effectiveness.0ne set of cloth switches was treated by exposing the swatches for ten minutes at 70 F. to an aqueous solution of a known concentration of softening agent with moderate stirring. The ratio of the cloth weight to that of the solution was 1:20. At the end of this time, the swatches were spun for six minutes in a spin cycle of a standard automatic home washer and then dried in a rotary dryer, also a household model. A second control set of test cloths of the same composition was treated by exactly the same method except that water was used in place of the softening solution. After drying, the two sets of fabrics were allowed to equilibrate for 24 hours at 45 relative humidity and 70 F. before presenting them to the panel for softness rating.
Non-expert panels of ten persons (both male and female) were employed. Each panel member was presented with four pairs of cloth swatches. The panelists were asked to handle each pair of swatches in turn and select the softer of the two cloths if a difference could be discerned. Two pairs of test swatches were comprised of the treated cloth and the control cloth presented in such a way that the treated cloth was handled first in one case and the control cloth in the other. The other two pairs of test swatches were comprised of control cloths exclusively and were designed to serve as a bench-mark for random selection between cloths of identical character. The order of presentation of pairs to the panelists was varied from person to person. Sets of fabrics comprised by four pairs of swatches were handled by no more than two persons each to avoid spurious results arising from pickup of skin oils, etc. The test swatches were coded in such a way that the panelist was unable to distinguish whether a particular cloth had been softened. Thus, after all ten panel members had handled the sets .of test swatches the number of panelists expressing a preference for the treated fabric was obtained and compared to the number of panelists unable to distinguish the test fabric from the control fabric.
(D) Determination of minimum level of a compound required for softening.Once a solution-concentration level of softener had been found at which a panel could distinguish unanimously between softened and unsoftened swatches the level of softener in solution in subsequent softening treatments was reduced by suitable stages until only one-half of the panelists repeatedly expressed a preference for the softened fabric as compared to the control fabric. This point was found to be surprisingly reproducible.
('E) Determination of softener level on cloth by extraction and analysis.Known weights of air-dried softened fabric swatches were placed in a large size Soxhlet extractor and extracted for 24 hours with a chloroform methanol axeotrope. After evaporation of solvent from the extract, the residue was made to known volume in a small volume of chloroform and an aliquot was added to 35 ml. of distilled water in a 100 ml. glass-stoppered cylinder containing methylene blue indicator. After addition of ml. of chloroform, analysis for the amine oxide was carried out by titration with a standard solution of alkylbenzenesulfonate to a methylene blue end point.
EXAMPLE I Test swatches of terry cloth treated in accordance with Procedure A were exposed to solutions of known concentrations of octadecyldimethylamine oxide and docosyldimethylamine oxide, respectively, using Procedure C. The results of panel grading of the softened cloths after the standard exposure and drying techniques are shown in the table.
It can be seen from the results of these paired comparisons that nearly three times as much of the octadecyldimethylamine oxide is required to soften the cloth to a level where 7 out of 10 panelists can distinguish the softness as is the case with the docosyldimethylamine oxide. This surprising result obtains even though there is a difference in molecular structure of only 4 methylene groups. It is also seen that the docosyldimethylamine oxide has appreciable softening activity in the range below parts per million where octadecyldimethylamine oxide is completely valueless. Additional softness testing studies with these compounds by Procedure D showed that the minimum level of compounds required in the rinse solution to produce noticeable softness (reproducibly detectable by half the panelists) was 67 parts per million in the case of the C18 amine oxide and only 29 parts per million in the case of the C22 amine oxide. Similar results to those above can be obtained by using eicosyl-bis- (fl-hydroxyethyUamine oxide, eicosyldimethylamine oxide, eicosyldiethylamine oxide, docosyl-bis-(fi-hydroxyethyl)amine oxide, docosyldimethylamine oxide, docosyldimethylamine oxide, tetracosyldimethylamine oxide, tetracosyl-bis-(fi-hydroxyethyDamine oxide, hexacosyldimethylamine oxide and hexacosyl-bis-(B-hydroxyethyl)- amine oxide, n-eicosylmorpholine-N-Oxide and N-docosylpyrrolidine-N-oxide.
EXAMPLE II This example shows the surprising effectiveness of the C amine oxide as compared to C and C amine oxides on muslin and on crash toweling, two fabrics which are much more difficult than terry cloth to render noticeably soft. In these tests, both the minimum level required to produce noticeable softening as judged by panel grading (Procedure D) and the weight percent of the amine oxide remaining on cloth as judged by the extraction experiments followed by analysis (Procedure E) were determined and are shown in the table. These results show that with these fabrics, the C amine oxide demonstrates a surprising superiority in softening over those compounds having a tallow length (C and C chain. The superiority is demonstrated both in the requirements for the amount of compound dissolved in the treating solution and also in the amount of compound which must be on the surface of the fibers in order to give the effect which the non-expert panelists can notice.
by fabrics upon exposure to the amine oxides having an alkyl radical of 20 to 30 carbon atoms is fully equivalent to that produced by the best commercial softeners. This degree of softening is not normally attained with dilute solutions except by using the cationic quaternary ammonium compounds. Separate applications of the cationic compound and the amine oxide to cloth were made in the manner described in Procedure C. The treated and control fabrics were presented to panel members in the same way as described except that in this case the panel members were asked to designate the degree of difference between the test swatches on a 0 to 4 scale (0=no difference; 1=the cloth indicated may be softer than the other one; 2=distinctly softer; 3=much softer; and 4=very much softer). Furthermore, to simulate as closely as possible the conditions which prevail when a softener is used in the home laundry situation, the fabrics were Washed with a typical heavy-duty anionic detergent formulation, softened in the rinse and again submitted to a panel for evaluation of the softness. The results of these studies are shown in the table for an amine oxide (A a 5050 mixture of eicosyldimethylamine oxide and docosyldimethylamine oxide) and a typical cationic softener (Bditallowdimethylammonium chloride).
Similar results to those above can be obtained by subsitituting on a molar basis the following compounds for the amine oxide softener in the above Example: eicosylbis- (18 'hydroxyethyDamine oxide, eicosyldimethylamine oxide eicosyldiethylamine oxide, docosyl bis (,8 hydroxyethyDamine' oxide, docosyl dimethylamine oxide, dojcosyldiethylamine oxide, tetracosyldimethylamine oxide,
r brs-(fl-hydroxyethyl)amine oxide, hexacosyl- ,diinetliyl'amine-oxide, hexacosyl bis-(fl-hydroxyethyl) airlineoxide,*N eicosylmorpholine-N-oxide and N-docosylpyrrolidiiie N ox'ide.
EXAMPLE IV This example shows the ability of the amine oxide softener to be essentially completely removed by a single wash in-a typical heavy-duty anionic detergent formulation. This very desirable feature thus prevents the buildup "of the"softener on the fabric with consequent waterproofin'gand yellowing of the fabric due to breakdown of the quaternary ammonium compound. In this test the fabrics were 'fsoft'e ried as before (Procedures A and C), then washed i'n a nautomatic washer with anionic detergent for'mulationone-o'r more times. The fabrics were present'e' the panel members both after application of the "'s'oftenerand after each subsequent wash to determine the softness impression. The softness impression (on a to 4 scale-'21s in Example-.111) gave an indication of the level of softener with fabric at each stage. The results are "reported-in the following table for the same amine oxide (A)"and quaternary ammonium (B) softeners de- Example III.
Number of panelists, out of ten preferring treated cloth and (in parentheses) average de gree of softening noticed on 0 if It is seen that the amine oxide softener is virtually completely removed by one wash step whereas substantial softener remains on the fabric after two washes when the cationic softener is used, even when only half the level of cationic softener is applied. Continued washing, through {5. washes, of fabrics to which had been added the cationic K (B) at 50 parts per million failed to completely remove (the cationic softener.
EXAMPLE v This example shows that the cloths softened with the amine oxide softeners having an alkyl radical of greater than 20 carbon atoms are such more absorbent than those which have been treated, with the quaternary ammonium salts which are ordinarily used. In this test, the cloths were exposed to 50 partsper million of the softener compounds in the usual way (Procedures A and C), washed in a standard anionic heavy-duty detergent formulation, then reexposed to 50 parts per million of softener in the rinse cycle. Washing and application of softener were repeated through a total of four cycles of softener application. After each application of softener was made, the cloths (after drying in the usual way) were tested for rewetability by the use of a standard sinking test. In this test the cloths were carefully placed on the surface of a large container of water at a standard temperature of 70 F. The time elapsed before the test fabric sank below the water surface was recorded. Control fabrics which had not been treated with softener of any kind normally required 5 to 6 seconds before sinking. The results of the sinking test on fabrics treated with either the amine oxide softener (A) or cationic softener (B) which are described in Example III are shown in the following table.
This example shows that the efiiciency of a typical cotton brightener in a softening composition is much better when amine oxide is used as the softening compound than when a typical cationic compound is used. In this test, 50 parts per million dispersions of (A) the C dimethylamine oxide or (B) ditallow-dimethylammonium chloride which comprises 0.005% of the solution by weight, into which were incorporated 2 parts per million of a bis-triazinylstilbene type cotton brightener 4,4'-bis[4- anilino-6-di(hydroxyethyl)amino sym triazin 2 ylamino] 2,2 stilbenedisulfonic acid which comprises 0.0002% of the solution of weight, were used to treat standard muslin test swatches. After ten minutes exposure time (as in Procedure C) followed by rinsing in distilled Water and drying, the muslin test swatches were placed in a fluorimeter to determine the extent of fluorescence conferred to the fabric, the following results were obtained: Y Formulation: Fluorimeter reading 50 p.p.m. A (amine oxide) +2 p.p.m. brightener 86 50 p.p.m. B (cationic)+2 p.p.m. brightener 33 Water+2 p.p.m. brightener 98 Thus, the interference with brightening by the amine oxide is very slight while the interference given by the quaternary ammonium salt is very extensive.
Results similar to the above are observed when the brightener used in the foregoing test is replaced with any of the following brighterers: 4,4-bis(4-anilino-6-dimor- 'pholine-sym-triazin-Z-ylamino) 2,2 stilbenedisulfonate and disodium 4,4-bis(4,6-dianilino sym triazin 2 ylamino) 2,2 stilbenedisulfonate, disodium 4,4-bis(4- anilino-6-ethylamino-sym-triazin-Z-ylamino) 2,2 stilbenedisulfonate and disodium 4,4'-bis(4-anilino 6 N- methylethanolamino sym triazin 2 ylamino)-2,2'- stilbenedisulfonate; bis benzoyl-, bis p aminobenzoyland bis-dimethoxybenzoylderivatives of 4,4 diaminostilbene-2,2' disulfonic acids; sodium 4(2H naphtho [1,2-d1triazol 2 yl) 2 stilbenesulfonate; 3,7-bis-pmethoxybenzoylamide)-dibenzothiophene 2,8 disulfonic acid-5,5-dioxidje'.
Other brightener compounds which can be used are those which are especially suitable for brightening synthetic fibers. Examples of these brighters include 1,2'-bis (5 methyI-Z-benzoxazolyl)ethylene, bis(5 methyl 2- benzoxolyl)thiophene and N hydroxyethyl 1,2 bis (benzimidazolyl)ethylene, 2 (m chlorostyryl-naptho- [l,2-d]oxazole and Z-styryl-benzoxazole; l p sulfonamidophenyl-3-p-chlorophenyl 2 pyrazoline; 4 methyl- 7-dimethylaminocoumarin and 3-phenyl-7-(diamino-symtriazinylamino coumarin.
EXAMPLE VII Sufficient docosyldimethylamine oxide to produce a level of 50 parts per million or 0.005% by weight of solution is introduced into the final the final rinse solution of a stnadard home automatic washing machine containing a load of mixed cotton fabrics from normal family usage. After completion of the rinse cycle, that is, exposure for about 5 minutes and then spin drying, the load is dried in an automatic dryer. Upon panel grading essentially like that of Procedure C, the fabrics are judged to be much softer and more desirable than fabrics which have not been treated with the amine oxide. It is also seen that fabrics such as washcloths and towels which have been treated with docosyldimethylamine oxide, while much softer than in the absence of the C amine oxide, are nevertheless very absorbent when used in the normal way and are easily rewet in the sinking test described in Example V.
EXAMPLE VIII When the conditions of Example VII are repeated using a mixed family load containing fine fabrics such as nylon and polyester and using a 50-50 mixture of eicosyldimethylamine oxide and docosyldimethylamine oxide it is seen that the fine fabrics are rendered largely antistatic and are much more desirable when worn than are the control fine fabrics which are not given a treatment with the amine oxide compound.
EXAMPLE IX This example shows the usefulness of a 50-50 mixture of eicosyldimethylamine oxide and docosyldimethylamine oxide when used in a padding-on process. Test swatches of terry cloth treated in accordance with Procedure A are completely submerged in an aqueous dispersion containing 0.7% of the softening mixture by weight. The cloth load comprised about 2% of the aqueous bath by weight. The test cloths are exposed to the foregoing dispersion of softening agents for a period of about seconds. The test cloths are then removed and passed between rubber rolls forcing out excess solution. The weight of the test cloths at this point is about 3 times their original dry weight. The test cloths are then dried in a standard automatic drier. Upon panel grading similar to that described in Procedure C, it is judged that the dried test cloths are much softer to the touch and fuller in appearance than in the absence of treatment with the foregoing mixture.
Similar results to those above can be obtained by substituting a like amount of the following compounds and mixtures thereof in, e.g., a 1:1 ratio by weight: eicosylbis-(,S-hydroxyethyl)amine oxide, eicosyldimethylamine oxide, eicosyldiethylamine oxide, tetracosyldimethylamine oxide, tetracosyl-bis-(p-hydroxyethyhamine oxide, hexacosyldimethylamine oxide, hexacosyl-bis-(B-hydroxyethyl) amine oxide, N eicosylmorpholine N oxide and N- docosylpyrrolidine-N-oxide.
The invention having been described, what is claimed 1. The process of treating textile materials which comprises the steps of: first, laundering with a detergent, and second, rinsing with an aqueous solution or dispersion consisting essentially of (A) from 0.001% to about 2.0% of a textile softener having the formula wherein R is a straight or branched carbon chain of about 22 carbon atoms selected from the group consisting of alkyl and alkenyl groups, R is an alkyl group containing from 1 to 20 carbon atoms and wherein said alkyl group contains not more than 2 hydroxyl substituents, not more than 5 ether linkages, not more than 2 chlorine atoms and not more than 1 amide linkage, and R is an alkyl group containing 1 to 3 carbon atoms selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, 2-hydroxyethyl and 2-hydroxypropyl, and wherein R and R can be joined to form a heterocyclic group containing 4 to 6 hydrocarbon groups, and
(B) the balance being water, all percentages being by weight.
2. The process of claim 1 wherein the aqueous solution contains from about 0.001% to about 0.05% textile softener.
3. The process of claim 2 wherein the aqueous solution contains from about 0.002% to about 0.01% textile softener.
4. The process of claim 1 wherein the aqueous solution contains from about 0.05% to about 2.0% textile softener.
S. The process of claim 4 wherein the aqueous solution contains from about 0.2% to about 1.0% textile softener.
6. The process of claim 1 wherein component (A) is docosyldimethylamine oxide.
7. The process of claim 1 wherein component (A) is docosyl-bis-(fi-hydroxyethyl) amine oxide.
8. The process of claim 1 wherein the aqueous solution contains from about 0.0001% to about 0.001% by weight of a brightening agent selected from the group consisting of 4,4 bis[4 anilino-6-di(hydroxyethyl)amino symtriazin-2-ylamino] 2,2 stilbenedisulfonic acid, disodium, 4,4-bis(4-anilino-6-morpholino sym triazin 2 ylamino) 2,2 stilbenedisulfonate, disodium 4,4 bis(4, 6-dianilino sym triazin 2 ylamino) 2,2 stilbenedisulfonate, disodium 4,4 bis(4 anilino-6-ethylaminosym triazin 2 ylamino) 2,2 stilbenedisulfonate, disodium, 4,4 bis(4 anilino 6 N methylethanolamino sym triazin 2 ylamino) 2,2 stilbenedisulfonate, sodium 4(2H naphtho[1,2-d]triazol-2-yl)-2- stilbenesulfonate, 2-(m-chlorostyryl) naphth [1,2-d]- oxazole, 1 p sulfonamidophenyl 3 p chlorophenyl- 2-pyrazoline, and 1,2 bis (5 methyl-Z-benzoxazolyl) ethylene, and mixtures thereof.
9. The process of claim 8 where in the aqueous solution contains from about 0.0002% to about 0.0005 of the brightening agent.
References Cited UNITED STATES PATENTS 2,734,830 2/1956 Hagge et al. 11733.5X 2,875,089 2/1959 Ackermann et al. 11733.5 2,977,319 3/1961 Ackermann et al. 252-301.2 3,202,714 8/1965 Zimmerer et al 260584 3,296,512 9/ 1965 Koebner et al 2528.8X 3,296,145 1/1967 Findlan et al. 252106 WILLIAM D. MARTIN, Primary Examiner T. G. DAVIS, Assistant Examiner U.S. Cl. X.R.
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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2230790A1 (en) * 1973-05-26 1974-12-20 Hoechst Ag
US4000077A (en) * 1972-05-04 1976-12-28 Colgate-Palmolive Company Enhancement of cationic softener
US4053992A (en) * 1970-10-20 1977-10-18 Colgate-Palmolive Company Apparatus and method for conditioning fibrous materials, utilizing and abradable conditioning agent fastened to the interior of an automatic laundry dryer door
US4057673A (en) * 1974-10-09 1977-11-08 Colgate Palmolive Company Fabric conditioning with improved composition containing a plasticizer
US4428846A (en) 1980-07-24 1984-01-31 Hoechst Aktiengesellschaft Dressing agents for synthetic fibers and their use
US4795032A (en) * 1987-12-04 1989-01-03 S. C. Johnson & Son, Inc. Wash-added, rinse-activated fabric conditioner and package
US4970008A (en) * 1988-12-20 1990-11-13 Kandathil Thomas V Fabric conditioner comprising a mixture of quaternary ammonium compounds and select tertiary amines
US20080229513A1 (en) * 2007-03-23 2008-09-25 John Michael Ogden Method of obtaining effective transfer of liquid fabric treatment compositions containing limited amounts of cationic compounds to clothing in washing machines

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3956302A (en) 1974-05-24 1976-05-11 The Upjohn Company Substituted pyrimidines
NZ201857A (en) * 1982-09-09 1985-09-13 Wool Res Organisation An antistatic composition containing a water insoluble quaternary ammonium salt and a nonionic surfactant
ES2065367T3 (en) * 1988-01-28 1995-02-16 Unilever Nv COMPOSITION FOR THE TREATMENT OF TISSUES AND THEIR PREPARATION.
DE19829787A1 (en) * 1998-07-03 2000-01-05 Henkel Kgaa Finishing agent

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4053992A (en) * 1970-10-20 1977-10-18 Colgate-Palmolive Company Apparatus and method for conditioning fibrous materials, utilizing and abradable conditioning agent fastened to the interior of an automatic laundry dryer door
US4000077A (en) * 1972-05-04 1976-12-28 Colgate-Palmolive Company Enhancement of cationic softener
FR2230790A1 (en) * 1973-05-26 1974-12-20 Hoechst Ag
US4057673A (en) * 1974-10-09 1977-11-08 Colgate Palmolive Company Fabric conditioning with improved composition containing a plasticizer
US4428846A (en) 1980-07-24 1984-01-31 Hoechst Aktiengesellschaft Dressing agents for synthetic fibers and their use
US4795032A (en) * 1987-12-04 1989-01-03 S. C. Johnson & Son, Inc. Wash-added, rinse-activated fabric conditioner and package
US4970008A (en) * 1988-12-20 1990-11-13 Kandathil Thomas V Fabric conditioner comprising a mixture of quaternary ammonium compounds and select tertiary amines
US20080229513A1 (en) * 2007-03-23 2008-09-25 John Michael Ogden Method of obtaining effective transfer of liquid fabric treatment compositions containing limited amounts of cationic compounds to clothing in washing machines

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