US3862045A - Antistatic softening composition - Google Patents

Antistatic softening composition Download PDF

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Publication number
US3862045A
US3862045A US304859A US30485972A US3862045A US 3862045 A US3862045 A US 3862045A US 304859 A US304859 A US 304859A US 30485972 A US30485972 A US 30485972A US 3862045 A US3862045 A US 3862045A
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US
United States
Prior art keywords
carbon atoms
antistatic
alkyl group
weight
softening composition
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US304859A
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English (en)
Inventor
Toshio Sato
Mamoru Katsumi
Natsuko Tsuda
Akira Yoshida
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Kao Corp
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Kao Corp
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Filing date
Publication date
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Publication of US3862045A publication Critical patent/US3862045A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • 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
    • D06M13/372—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
    • D06M13/46—Compounds containing quaternary nitrogen atoms

Definitions

  • At least one antistatic agent selected from compounds expressed by the following formula (CH CH O) H wherein R, is an alkyl group having 14 to 22 carbon atoms, R stands for an alkyl group having 1 to 3 carbon atoms of a benzyl group, X designates Cl, Br or C H SO and the sum of m and n is from 5 to 20,
  • Softening agents have heretofore been used frequently as finishing agents for textile fabrics. They are utilized mainly for-finishing underwears and diapers after washing thereof to impart soft touch to these textile fabrics. Important properties required of softening agents are as follows.
  • Fabric softening agents of various compositions are known in the art, but most of them' comprise as a main ingredient a quaternary, ammonium salt having two long-chain alkyl groups.
  • non-ionic surfactants such as alkylphenol-ethylene oxide adducts and solvents such as alcohols and/or glycols are added to such main ingredient so as to improve the solution stability and other properties.
  • non-ionic surfactants such as alkylphenol-ethylene oxide adducts and solvents such as alcohols and/or glycols are added to such main ingredient so as to improve the solution stability and other properties.
  • a fabric softening agent In order to impart antistatic activity-to a fabric softening agent, it may at first be considered to incorporate into the composition an antistatic agent.
  • an antistatic agent when for instance, stearyl trimethyl ammonium chloride, which is an antistatic agent broadly used, is incorporated into a fabric softening agent comprising as a 5 main ingredient a quaternary ammonium salt having two long-chain alkyl groups, an antistatic effect may be attained, but the stability of an aqueous solution of the agent is extremely lowered, with the result that the agent is no longer applicable to practical use.
  • this invention provides a softening composition which exhibits an excellent softening effect to fabrics and a sufficient solution stability even at a high concentration and which can impart an excellent antistatic property to the treated textile fabrics.
  • an antistatic softening composition comprising the following four ingredients (I) to-(IV):
  • At least one antistatic agent selected from compounds expressed by 'the following formula- (ea ca m R -'N R X and compounds expressed by the following formula 3 wherein R is an alkyl group havnig l6 to 22 carbon atoms, R, and R stand independently for an alkyl group having 1 to 3 carbon atoms, and p is a number of from 1 to 4; having lll.
  • IV 2 percent by weight of at least one additive selected from the group consisting of alcohols having l to 3 carbon atoms, glycols having 2 to 3 carbon atoms. glycerol. sorbitol and urea.
  • the balance of the composition is water.
  • the quaternary ammonium salt (I) there may be preferably mentioned, distearyl dimethyl ammonium chloride and di-halogenatcd-tallt)walkyl dimethyl ammonium chloride.
  • the non-ionic surfactant (lll) include R,;()(CH CH Ol,,,H (in which R.; is an alkyl group having l2 to 18 carbon atoms),
  • composition of this invention comprising the above ingredients alone can fully attain the intended objects of this invention, but in order to ensure the stability on storage for a long period. it is preferred that the composition is incorporated with a small amount of an inorganic salt such as NaCl and Na SO,. usually ().()l to 0.5 percent by weight.
  • the composition of this invention is further characterized in that. when a fluorescent dye of the distilbene or diaminostilbene type is incorporated in the composition ofthis invention. the fluorescent dye exhausts on the fabrics and acts effectively.
  • EXAMPLE l Antistatic agents were incorporated into a softening composition, and the solution stability, and the antistatic effect and other properties of treated products were 7 (in WhlCh R7 iS an alkyl group having 8 IO 12 carbon Distearyl dimethyl ammonium 6.4% by weight atoms) and R,,COO(CH CH O),,,H.(in which R, is an zl gi by weight alkyl group having 1 l to 17 carbon atoms), in each of Nrmylphenol polyoxyethylenc 1:07! by weight which it is preferred that m is a number of from to E l e s U h h 90.
  • EO means C H O and Rcoco indicates a coconut alkyl (cocoyl) group.
  • the viscosity is expressed in the cps unit.
  • R indicates an alkyl group ofC,H and R shows the presence of a double bond.
  • compositions incorporated with anionic antistatic agents H to K and non-ionic antistatic agents L and P fail to impart intended antistatic performance to treated products, and other performances and stability are also insufficient.
  • Compositions incorporated with cationic antistatic agents A to D can impart sufficient antistatic property. but compositions incorporated with antistatic agents A, B, B and D are defective in solution stability and whiteness of the treated fabrics and they are not usable for practical applications.
  • the composition incorporated with antistatic agent C is not completely satisfactory, it can be put into practical use.
  • the composition incorporated with antistatic agent C is especially excellent in various properties.
  • Compositions incorporated with amphoteric antistatic agents E to G can impart sufficient antistatic property, but compositions incorporated with antistatic agents F and G are defective in stability and whiteness of the treated product and they cannot be put into practical use.
  • the sample was allowed to stand in a thermostat chamber maintained at 50C. for 1 month, and the state i of the sample was examined as to whether the phase separation was caused.
  • compositions were allowed to stand at room temperature for l month after blending, and the viscosities were measured at 30C.. each value being expressed in the cps unit.
  • a cotton towel cloth, a bleached cotton diaper cloth and an acrylic blanket were respectively washed according to an ordinary method, and treated with a ().l or 0.3 percent solution of the softening composition, followed by drying.
  • Each sample was subjected to the touch test by 5 men and 5 women, and the softness was evaluated based on points given to the sample.
  • Each value shown in Table 4 is the sum of points given by each tester. Thus, a higher value means a higher softness.
  • a cotton broadcloth was treated with a ().l or 0.3 percent solution of the softening composition and dried.
  • the resulting cloth was used'as a test sample.
  • the water absorption was measured according to Klemm method (the method in which the sample cloth is kept in the vertical state, the bottom 'is'dipped in water, and the rate of water rise is measured).
  • Klemm method the method in which the sample cloth is kept in the vertical state, the bottom 'is'dipped in water, and the rate of water rise is measured.
  • Table 4' the position of water rising within 1 minute from dipping was expressed in the cm unit.
  • ammonium chloride dipolyoxyethylene (8) pol-yoxyethylene (7.0%) ammonium chloride (85) ether (0.9%)
  • ammonium chloride 8 di-hy'droQenated- CH nonylphenol ethylene NaCl 1 beef-tallow-alkyl R 4 6 6) polyoxyethylene glycol (0.02%)
  • An antistatic fabric softening composition com-- tca ca m a R-N-R X I (ca cn o) I-l wherein R, is an alkyl group having l4 to 22 carbon atoms. R stands for an alkyl group having I to 3 carbon atoms or a benzyl group. X designates Cl, Br or C H SO and the sum of m and n is from 5 to 20,

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US304859A 1971-11-15 1972-11-08 Antistatic softening composition Expired - Lifetime US3862045A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP46091342A JPS5010439B2 (zh) 1971-11-15 1971-11-15

Publications (1)

Publication Number Publication Date
US3862045A true US3862045A (en) 1975-01-21

Family

ID=14023733

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Application Number Title Priority Date Filing Date
US304859A Expired - Lifetime US3862045A (en) 1971-11-15 1972-11-08 Antistatic softening composition

Country Status (6)

Country Link
US (1) US3862045A (zh)
JP (1) JPS5010439B2 (zh)
AU (1) AU468135B2 (zh)
DE (1) DE2255260C3 (zh)
ES (1) ES408371A1 (zh)
GB (1) GB1410790A (zh)

Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4038196A (en) * 1975-03-12 1977-07-26 Kao Soap Co., Ltd. Softening agent for woven fabrics
US4102825A (en) * 1976-10-01 1978-07-25 Kao Soap Co., Ltd. Liquid light-duty detergent composition
US4139477A (en) * 1978-03-16 1979-02-13 E. I. Du Pont De Nemours And Company Fabric conditioning compositions
US4144367A (en) * 1977-05-09 1979-03-13 Minnesota Mining And Manufacturing Company Carpet-treating compositions
US4160823A (en) * 1976-03-29 1979-07-10 Kao Soap Co., Ltd. Transparent hair rinsing composition
US4203872A (en) * 1975-08-01 1980-05-20 Flanagan John J Surfactant system
US4222905A (en) * 1978-06-26 1980-09-16 The Procter & Gamble Company Laundry detergent compositions having enhanced particulate soil removal performance
US4228044A (en) * 1978-06-26 1980-10-14 The Procter & Gamble Company Laundry detergent compositions having enhanced particulate soil removal and antiredeposition performance
US4259217A (en) * 1978-03-07 1981-03-31 The Procter & Gamble Company Laundry detergent compositions having enhanced greasy and oily soil removal performance
US4264479A (en) * 1978-12-18 1981-04-28 Flanagan John J Surfactant system
US4268401A (en) * 1975-07-02 1981-05-19 Blendax-Werke R. Schneider Gmbh & Co. Liquid detergent compositions having washing and softening properties
US4284435A (en) * 1979-11-28 1981-08-18 S. C. Johnson & Son, Inc. Method for spray cleaning painted surfaces
US4369134A (en) * 1980-02-05 1983-01-18 Kao Soap Co., Ltd. Creamy cleansing compositions
US4391605A (en) * 1980-08-07 1983-07-05 Wool Development International Limited Textile treatment
US4493773A (en) * 1982-05-10 1985-01-15 The Procter & Gamble Company Low phosphate, softening laundry detergent containing ethoxylated nonionic, alkylpolysaccharide and cationic surfactants
US4540521A (en) * 1984-01-16 1985-09-10 National Distillers And Chemical Corporation Liquid quaternary ammonium antistatic compositions
FR2586425A1 (fr) * 1985-08-20 1987-02-27 Colgate Palmolive Co Compositions detergentes liquides contenant des agents stabilisants en suspension et un additif du type uree et procedes pour nettoyer des tissus les utilisant
US4789496A (en) * 1985-08-20 1988-12-06 Colgate-Palmolive Company Built nonaqueous liquid nonionic laundry detergent composition containing
US4844822A (en) * 1987-07-06 1989-07-04 The Dial Corporation Softener/antistat compositions
US4895667A (en) * 1988-05-24 1990-01-23 The Dial Corporation Fabric treating compositions
US4917842A (en) * 1988-02-12 1990-04-17 The Standard Oil Company Process of making ceramics
US5336447A (en) * 1990-11-30 1994-08-09 Lever Brothers Company, Division Of Conopco, Inc. Process and composition for treating fabrics
US6369159B1 (en) 1987-05-13 2002-04-09 Pdm Holdings Corp. Antistatic plastic materials containing epihalohydrin polymers
US20060138380A1 (en) * 2003-06-26 2006-06-29 Torsten Kulke Aqueous liquid compositions of cyclodextrine or cyclodextrine derivatives and a process using the said composition
US20160215237A1 (en) * 2013-10-10 2016-07-28 Akzo Nobel Chemicals International B.V. Fabric Softener Composition and The Use Thereof
WO2023239891A1 (en) 2022-06-10 2023-12-14 Lubrizol Advanced Materials, Inc. Thermoplastic polyurethanes with high temperature stability and uses thereof
WO2024102687A1 (en) 2022-11-08 2024-05-16 Lubrizol Advanced Materials, Inc. High resilient thermoplastic polyurethanes and uses thereof

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2525610C2 (de) * 1975-06-09 1985-04-11 Henkel KGaA, 4000 Düsseldorf Kationische Avivagemittel mit verbesserter Kaltwasserlöslichkeit
JPS52141446U (zh) * 1976-04-17 1977-10-26
JPS5619846Y2 (zh) * 1979-06-27 1981-05-12
SE464139B (sv) * 1983-05-11 1991-03-11 Colgate Palmolive Co Koncentrerad textilmjukgoerande komposition och foerfaranden foer tillverkning av densamma
JPS61102481A (ja) * 1984-10-25 1986-05-21 ライオン株式会社 柔軟剤組成物
JP2660205B2 (ja) * 1988-06-03 1997-10-08 ミヨシ油脂株式会社 繊維処理剤の製造方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3578592A (en) * 1967-09-15 1971-05-11 American Cyanamid Co Imidazoline quaternary salts as soil retardants
US3681241A (en) * 1968-03-04 1972-08-01 Lever Brothers Ltd Fabric softening
US3703480A (en) * 1970-11-16 1972-11-21 Colgate Palmolive Co Fabric-softener compositions
US3756950A (en) * 1971-03-08 1973-09-04 Lever Brothers Ltd Fabric softening compositions

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3578592A (en) * 1967-09-15 1971-05-11 American Cyanamid Co Imidazoline quaternary salts as soil retardants
US3681241A (en) * 1968-03-04 1972-08-01 Lever Brothers Ltd Fabric softening
US3703480A (en) * 1970-11-16 1972-11-21 Colgate Palmolive Co Fabric-softener compositions
US3756950A (en) * 1971-03-08 1973-09-04 Lever Brothers Ltd Fabric softening compositions

Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4038196A (en) * 1975-03-12 1977-07-26 Kao Soap Co., Ltd. Softening agent for woven fabrics
US4268401A (en) * 1975-07-02 1981-05-19 Blendax-Werke R. Schneider Gmbh & Co. Liquid detergent compositions having washing and softening properties
US4203872A (en) * 1975-08-01 1980-05-20 Flanagan John J Surfactant system
US4160823A (en) * 1976-03-29 1979-07-10 Kao Soap Co., Ltd. Transparent hair rinsing composition
US4102825A (en) * 1976-10-01 1978-07-25 Kao Soap Co., Ltd. Liquid light-duty detergent composition
US4144367A (en) * 1977-05-09 1979-03-13 Minnesota Mining And Manufacturing Company Carpet-treating compositions
US4259217A (en) * 1978-03-07 1981-03-31 The Procter & Gamble Company Laundry detergent compositions having enhanced greasy and oily soil removal performance
US4139477A (en) * 1978-03-16 1979-02-13 E. I. Du Pont De Nemours And Company Fabric conditioning compositions
US4222905A (en) * 1978-06-26 1980-09-16 The Procter & Gamble Company Laundry detergent compositions having enhanced particulate soil removal performance
US4228044A (en) * 1978-06-26 1980-10-14 The Procter & Gamble Company Laundry detergent compositions having enhanced particulate soil removal and antiredeposition performance
US4264479A (en) * 1978-12-18 1981-04-28 Flanagan John J Surfactant system
US4284435A (en) * 1979-11-28 1981-08-18 S. C. Johnson & Son, Inc. Method for spray cleaning painted surfaces
US4369134A (en) * 1980-02-05 1983-01-18 Kao Soap Co., Ltd. Creamy cleansing compositions
US4391605A (en) * 1980-08-07 1983-07-05 Wool Development International Limited Textile treatment
US4493773A (en) * 1982-05-10 1985-01-15 The Procter & Gamble Company Low phosphate, softening laundry detergent containing ethoxylated nonionic, alkylpolysaccharide and cationic surfactants
US4540521A (en) * 1984-01-16 1985-09-10 National Distillers And Chemical Corporation Liquid quaternary ammonium antistatic compositions
FR2586425A1 (fr) * 1985-08-20 1987-02-27 Colgate Palmolive Co Compositions detergentes liquides contenant des agents stabilisants en suspension et un additif du type uree et procedes pour nettoyer des tissus les utilisant
US4789496A (en) * 1985-08-20 1988-12-06 Colgate-Palmolive Company Built nonaqueous liquid nonionic laundry detergent composition containing
US6369159B1 (en) 1987-05-13 2002-04-09 Pdm Holdings Corp. Antistatic plastic materials containing epihalohydrin polymers
US4844822A (en) * 1987-07-06 1989-07-04 The Dial Corporation Softener/antistat compositions
US4917842A (en) * 1988-02-12 1990-04-17 The Standard Oil Company Process of making ceramics
US4895667A (en) * 1988-05-24 1990-01-23 The Dial Corporation Fabric treating compositions
US5336447A (en) * 1990-11-30 1994-08-09 Lever Brothers Company, Division Of Conopco, Inc. Process and composition for treating fabrics
US20060138380A1 (en) * 2003-06-26 2006-06-29 Torsten Kulke Aqueous liquid compositions of cyclodextrine or cyclodextrine derivatives and a process using the said composition
US20160215237A1 (en) * 2013-10-10 2016-07-28 Akzo Nobel Chemicals International B.V. Fabric Softener Composition and The Use Thereof
WO2023239891A1 (en) 2022-06-10 2023-12-14 Lubrizol Advanced Materials, Inc. Thermoplastic polyurethanes with high temperature stability and uses thereof
WO2024102687A1 (en) 2022-11-08 2024-05-16 Lubrizol Advanced Materials, Inc. High resilient thermoplastic polyurethanes and uses thereof

Also Published As

Publication number Publication date
AU4891572A (en) 1974-05-16
AU468135B2 (en) 1976-01-08
ES408371A1 (es) 1975-11-01
JPS5010439B2 (zh) 1975-04-21
DE2255260B2 (de) 1978-10-26
DE2255260A1 (de) 1973-05-24
GB1410790A (en) 1975-10-22
DE2255260C3 (de) 1979-06-21
JPS4854300A (zh) 1973-07-30

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