WO1988000990A1 - Composition adoucissante de textiles sous forme de poudre hydrosoluble a haute fluidite et procede de fabrication de ladite composition - Google Patents

Composition adoucissante de textiles sous forme de poudre hydrosoluble a haute fluidite et procede de fabrication de ladite composition Download PDF

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Publication number
WO1988000990A1
WO1988000990A1 PCT/US1986/001582 US8601582W WO8800990A1 WO 1988000990 A1 WO1988000990 A1 WO 1988000990A1 US 8601582 W US8601582 W US 8601582W WO 8800990 A1 WO8800990 A1 WO 8800990A1
Authority
WO
WIPO (PCT)
Prior art keywords
processing aid
composition
alkyl group
polyoxyalkylene derivative
formula
Prior art date
Application number
PCT/US1986/001582
Other languages
English (en)
Inventor
Leonard Hughes
James G. Fuller
William J. Zeman
Original Assignee
Leonard Hughes
Fuller James G
Zeman William J
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Leonard Hughes, Fuller James G, Zeman William J filed Critical Leonard Hughes
Priority to EP19860905056 priority Critical patent/EP0274468A4/fr
Priority to JP50441686A priority patent/JPH01500282A/ja
Priority to PCT/US1986/001582 priority patent/WO1988000990A1/fr
Publication of WO1988000990A1 publication Critical patent/WO1988000990A1/fr

Links

Classifications

    • 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
    • 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
    • C11D1/66—Non-ionic compounds
    • C11D1/835—Mixtures of non-ionic with cationic compounds
    • 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
    • D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
    • D06M13/188—Monocarboxylic acids; Anhydrides, halides or salts 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
    • D06M13/46—Compounds containing quaternary nitrogen atoms
    • D06M13/467—Compounds containing quaternary nitrogen atoms derived from polyamines
    • 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
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds
    • 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
    • C11D1/66—Non-ionic compounds
    • C11D1/72—Ethers of polyoxyalkylene glycols
    • 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
    • C11D1/66—Non-ionic compounds
    • C11D1/72—Ethers of polyoxyalkylene glycols
    • C11D1/721—End blocked 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/74—Carboxylates or sulfonates esters of polyoxyalkylene glycols

Definitions

  • This invention relates to water dispersible, free flowing solid softening compositions for textiles and textile fibers, and a process for their manufacture.
  • Aqueous pastes are by their nature incapable of being incorporated into powdered laundry products, without deleteriously affecting the free flowing characteristics of such products. Further, aqueous pastes or dispersions suffer from handling, storing, packaging, and shipping disadvantages.
  • aqueous dispersions suffer from the inherent problems of aqueous pastes, and in addition, require the use of bulkier rigid metal or plastic shipping containers, which increases the cost of storage and transportation.
  • dialkyldiamido quaternary fabric softeners in particulate or powder form.
  • the physical properties of dialkyldiamido quaternary compounds e.g. ; high viscosity in the molten state; melting range, on the order of 100°C; and a decomposition temperature of about 120°C; are not conducive to preparation of particulates or powders.
  • the present invention is directed to a particulate, water dispersible, free flowing fabric softener composition.
  • a composition may be obtained by admixing an effective quantity of a processing aid, such as a polyoxyalkylene derivative, with a dialkyldiamido quaternary compound, melting them, and atomizing the molten mixture in conventional equipment appropriate for obtaining particulate material from a molten mixture.
  • the particulate product obtained permits the use of dialkyldiamido quaternary fabric softening compound in solid laundry products without altering their free flowing characteristics. Being a solid, the particulate product does not suffer from the physical handling drawbacks associated with pastes of dialkyldiamido quaternary compounds, while at the same time, being easily dispersed in water.
  • dialkyldiamido quaternary fabric softening compositions in the form of free flowing, water dispersable particulates or powders.
  • the art in the field of dialkyldiamido quatenary compounds which function well as fabric softeners is directed to non—powders, i.e., aqueous pastes or dispersions.
  • the physical properties of dialkyldiamido quaternary compounds are conducive to their preparation as aqueous pastes or dispersions and they are marketed and shipped to for ulators in these forms. _ , _
  • dialkyldiamido quaternary fabric softening compounds of this invention is taught e.g. , by U.S. Patent number 3,492,324.
  • fatty acids are reacted with diethylenetriamine in a mole ratio of 2:1.
  • the resulting dialkyldiamidoamine is methylated by reaction with formic acid and/or formaldehyde, and the resulting dialkylamidoethyl methylamine is quaternized with conventional reagents, e.g. , dimethyl sulfate.
  • benzyl chloride, methyl chloride and dimethylsulfate are suitable quaternizing agents for tertiary amines, such as the dialkyldiamidomethylamine described above.
  • methyl chloride may be reacted with secondary amines such as the dialkyldiamidoamine described above, in a mole ratio of 2:1 respectively, to produce a quaternary compound useful for fabric softening.
  • dialkyldiamido quaternary compounds In order for dialkyldiamido quaternary compounds to be more widely useful as fabric softeners, especially in free flowing laundry detergent compositions, and to overcome the problems inherent in shipment, storage and use as aqueous pastes and dispersions, a particulate form of the dialkyldiamido quaternary compound is desirable.
  • Conventional atomizing equipment to produce such particulates includes spray drying, spray congealing, and prilling devices among others. Spray drying and spray congealing, for example, necessitate pumping liquified quaternary compounds through narrow orifices under sufficient pressure to produce fine droplets; these processes have proven to be relatively expensive and operationally difficult.
  • the viscosity of the molten dialkyldiamido quaternary compound is such that it is incapable of being pumped neat at the maximum allowable temperature, i.e., the temperature of incipient decomposition. That is, at the maximum permissible temperature, the viscosity of the dialkyldiamido quaternary compound itself exceeds the physical limitations of conventional pumps, within the limits of economic practicality. Thus the pump cavitates or otherwise fails to transfer- the molten material from the input reservoir to the output. This condition is exacerbated when the output is a narrow constriction or orifice, as is the case in conventional atomization equipment.
  • Conventional atomization equipment includes devices such as spray nozzles, rotating disks, or shot towers. Some of these devices function by forcing a liquid through narrow orifices to produce fine droplets. The droplets solidify to form the particulate. Cooling, e.g., by means of refrigerated air or other gasses, may be provided to aid solidifcation of said droplets.
  • the range of particles in the particulate thus produced is nominally from 10 to 900 microns in diameter, with the preferred range for the use of this invention averaging from 100 to 300 microns in diameter.
  • the orifice sizes may range from about 0.1 to 5 millimeters in diameter.
  • fatty acid derived dialkyldiamido quaternary compounds which are ordinarily solids at room temperature, must be liquified to utilize atomization equipment and thus form a particulate.
  • Liquification of fatty acid derived dialkyldiamido quaternary compounds may be accomplished by heating to 100 to 120°C. Higher temperatures usually result in degradation of the product as evidenced by discoloration or browning.
  • the viscosity i.e., the ability to pass through an orifice, of di (hard tallow) dia ido quaternary compounds is extremely high, and has been measured at over 160,000 centipoises.
  • This viscosity is such as to incapacitate conventional mechanical pumps, within the limits of economic practicality, necessary to the atomization process, as has been described in the foregoing.
  • Attempts to reduce viscosity by means of increasing the temperature results in decomposition of the quaternary compound itself.
  • water could be added to dilute the molten mass, and thus reduce the viscosity.
  • additional water sufficient to facilitate pumping results in products with unacceptably high water content.
  • Tack may be evaluated by determining the force, in pounds, necessary to break a formed cake of the respective material. The cake is formed by compacting 450ml of product in a circular mold, 8.57cm in diamter and 12.7cm high, with a 9.98kg piston, at room temperature for 2 minutes.
  • Solvents other than water for example isopropyl alcohol, may be added to reduce the viscosity of the molten quaternary compound. Sufficient quantities of isopropyl alcohol to facilitate pumping also result in unacceptably high levels of "tack". Further, isopropyl alcohol, being flammable, presents additional problems in commercial scale equipment. There is an inherent explosion hazard, and the vaporized isopropyl alcohol must be recovered from the vapor state in an environmentally acceptable manner. The equipment required to accomplish this recovery, i.e. , by condensation, is both costly and cumbersome.
  • a particulate, free flowing water dispersible fabric softener composition may be obtained by conventional atomization techniques.
  • the addition of polyoxylalkylene derivatives significantly reduces the viscosity of the molten quaternary compound, facilitating atomization with conventional equipment, while not decreasing the free flowing characteristics or the dispersibility of the resultant particulate. This is evidenced by little significant change in either "tack" or dispersibility, when the polyoxyalkylene processing aid is incorporated into the dialkyldiamido quaternary compound.
  • the polyoxyalkylene derivative that we have found most advantageous as a processing aid is the reaction product of approximately 30 moles of ethylene oxide with one mole of the monoglyceryl ester of coconut fatty acids.
  • the preferred amount of this polyoxyalkylene derivative processing aid is 10" by weight of the quaternary compound. More or less of the polyoxyalkylene derivative may be effective as a processing aid; from about 3 percent to about 15 percent of the dialkyldiamido quaternary compound. Less than these amounts would tend to be ineffective in reducing viscosity and more would tend to increase the "tack" of the particulate.
  • polyoxyalkylene derivatives which have been shown to be advantageous as processing aids in varying percentages from about 3 to about 15 by weight of dialkyldiamido quaternary compound, include commercially available ethoxylated sorbitan oleate derivatives, and ethoxylated fatty alcohols.
  • the preferred fatty acid derived dialkyldiamido quaternary compound is that derived from hardened tallow fatty acids as in Example I below.
  • Dialkyldiaraidoethyl methyl ammonium methosulfate compound prepared from hardened tallow fatty acids was melted at 110°C and atomized through a nozzle having an orifice 1.2 microns in diameter at a pressure of 2000 psi.
  • the atomized droplets were congealed, in air., at a temperature of 15 to 21°C and a relative humidity of 50%.
  • the congealed particulate having a particle size range averaging from 100 to 300 microns in diameter was subsequently vacuum dried at 40°C to remove residual isopropanol, from the preparation of the quaternary compound.
  • Example 3 Chemical Company, Dublin, OH). The mixture was melted at 110°C and atomized through the identical equipment of Example 1. Only a small quantity of particulate was obtained before pumps and lines became plugged, rendering the equipment inoperable. Residual isopropanol from preparation of the quaternary compound was removed as in Example 1. E XAMPLE 3
  • Example 1 To 90 parts of the quaternary compound of the Example 1 were added 10 parts of isopropyl alcohol and 10 parts of ethoxylated sorbitan mono oleate, (Tween ® 80, ICI Americas, Wilmington, DL; 20 moles of ethylene oxide per mole of sorbitan mono oleate). The mixture was melted at 110°C, and atomized, congealed and vacuum dried as in Example 1.
  • Example 1 90 parts of the quaternary compound of Example I were admixed with 10 parts of ethoxylated isostearyl alcohols (Arosurf ® AA 66E-20, Sherex Chemical Company, Dublin, OH 20 moles of ethylene oxide per mole of isostearyl alcohol), and 10 parts of isopropyl alcohol. The mixture was melted at 110°C, atomized, congealed and dried as in Example 1.
  • ethoxylated isostearyl alcohols Rosurf ® AA 66E-20, Sherex Chemical Company, Dublin, OH 20 moles of ethylene oxide per mole of isostearyl alcohol
  • Example 1 without processing aid, overwhelmed the physical capability of the spray congealing equipment (See Example 1) .
  • Example 1 to 4 were determined by visual inspection of a mixture of 0.3 grams of product in 100 grams of water, after agitation at 32°C for 10 minutes. The results are presented in Table 2:
  • Unaccep able dispersions contain solid clumps and clear areas
  • the dispersibility of the particulate obtained by the use of a processing aid is significantly better than when no processing aid is present as in Example 1.
  • the "tack" of the particulate of Example 1 to 4 was evaluated by determining the force in kilograms necessary to break a formed cake of the resepective material.
  • the cake is formed by compacting 450 ml of product in a circular mold 8.57cm in diameter and 12.7cm high, with a 9.98kg piston, at room temperature for 2 minutes.
  • the results are presented in Table 3.
  • isopropanol significantly increases the "tack" i.e., reduces the ability of the particulate to flow freely while the preferred processing aids do not.

Landscapes

  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Textile Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

En ajoutant jusqu'à 15 % en poids d'un dérivé de polyoxyalkylène à un composé quaternaire de dialkylamidométhylamino dérivé d'acides gras, on obtient l'atomisation dudit composé dans des équipements traditionnels. Le produit adoucissant de textiles qui en résulte se présente sous la forme désirée d'une poudre solide hydrosoluble à haute fluidité.
PCT/US1986/001582 1986-08-04 1986-08-04 Composition adoucissante de textiles sous forme de poudre hydrosoluble a haute fluidite et procede de fabrication de ladite composition WO1988000990A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP19860905056 EP0274468A4 (fr) 1986-08-04 1986-08-04 Composition adoucissante de textiles sous forme de poudre hydrosoluble a haute fluidite et procede de fabrication de ladite composition.
JP50441686A JPH01500282A (ja) 1986-08-04 1986-08-04 粒子の水分散をさせることができる易流動性の布帛軟化剤組成物及びそれを作る方法
PCT/US1986/001582 WO1988000990A1 (fr) 1986-08-04 1986-08-04 Composition adoucissante de textiles sous forme de poudre hydrosoluble a haute fluidite et procede de fabrication de ladite composition

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US1986/001582 WO1988000990A1 (fr) 1986-08-04 1986-08-04 Composition adoucissante de textiles sous forme de poudre hydrosoluble a haute fluidite et procede de fabrication de ladite composition

Publications (1)

Publication Number Publication Date
WO1988000990A1 true WO1988000990A1 (fr) 1988-02-11

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PCT/US1986/001582 WO1988000990A1 (fr) 1986-08-04 1986-08-04 Composition adoucissante de textiles sous forme de poudre hydrosoluble a haute fluidite et procede de fabrication de ladite composition

Country Status (3)

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EP (1) EP0274468A4 (fr)
JP (1) JPH01500282A (fr)
WO (1) WO1988000990A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992018593A1 (fr) * 1991-04-22 1992-10-29 The Procter & Gamble Company Compositions assouplissantes granulaires pour tissus, formant des concentres sous forme d'emulsions aqueuses
US5468398A (en) * 1993-05-20 1995-11-21 Colgate-Palmolive Company Liquid fabric softening composition
US5536421A (en) * 1992-09-28 1996-07-16 The Procter & Gamble Company Method for using solid particulate fabric softener in automatic dosing dispenser

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3492324A (en) * 1963-04-26 1970-01-27 I C I Organics Inc Quaternary salts of tertiary amines
US3933871A (en) * 1973-11-12 1976-01-20 Armstrong Chemical Company, Inc. Fabric softener compound and processes for preparing and using the same
US4102795A (en) * 1976-04-30 1978-07-25 Kao Soap Co., Ltd. Softener composition for fabrics or hair
US4155710A (en) * 1978-03-30 1979-05-22 Kewanee Industries, Inc. Process for preventing fading in textiles
US4239631A (en) * 1979-12-11 1980-12-16 Finetex Incorporated Cationic surfactant compositions compatible with anionic surfactants
US4399045A (en) * 1980-11-18 1983-08-16 The Procter & Gamble Company Concentrated fabric softening compositions
US4439335A (en) * 1981-11-17 1984-03-27 The Procter & Gamble Company Concentrated fabric softening compositions

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4497716A (en) * 1982-12-23 1985-02-05 Lever Brothers Company Fabric softening composition

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3492324A (en) * 1963-04-26 1970-01-27 I C I Organics Inc Quaternary salts of tertiary amines
US3933871A (en) * 1973-11-12 1976-01-20 Armstrong Chemical Company, Inc. Fabric softener compound and processes for preparing and using the same
US4102795A (en) * 1976-04-30 1978-07-25 Kao Soap Co., Ltd. Softener composition for fabrics or hair
US4155710A (en) * 1978-03-30 1979-05-22 Kewanee Industries, Inc. Process for preventing fading in textiles
US4239631A (en) * 1979-12-11 1980-12-16 Finetex Incorporated Cationic surfactant compositions compatible with anionic surfactants
US4399045A (en) * 1980-11-18 1983-08-16 The Procter & Gamble Company Concentrated fabric softening compositions
US4439335A (en) * 1981-11-17 1984-03-27 The Procter & Gamble Company Concentrated fabric softening compositions

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP0274468A4 *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992018593A1 (fr) * 1991-04-22 1992-10-29 The Procter & Gamble Company Compositions assouplissantes granulaires pour tissus, formant des concentres sous forme d'emulsions aqueuses
US5185088A (en) * 1991-04-22 1993-02-09 The Procter & Gamble Company Granular fabric softener compositions which form aqueous emulsion concentrates
US5536421A (en) * 1992-09-28 1996-07-16 The Procter & Gamble Company Method for using solid particulate fabric softener in automatic dosing dispenser
US5792219A (en) * 1992-09-28 1998-08-11 The Procter & Gamble Company Method for using solid particulate fabric softener in automatic dosing dispenser
US5468398A (en) * 1993-05-20 1995-11-21 Colgate-Palmolive Company Liquid fabric softening composition

Also Published As

Publication number Publication date
EP0274468A4 (fr) 1989-08-22
EP0274468A1 (fr) 1988-07-20
JPH01500282A (ja) 1989-02-02

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