WO1992022535A1 - Fabric softening agents and compositions thereof - Google Patents

Fabric softening agents and compositions thereof Download PDF

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Publication number
WO1992022535A1
WO1992022535A1 PCT/US1992/004905 US9204905W WO9222535A1 WO 1992022535 A1 WO1992022535 A1 WO 1992022535A1 US 9204905 W US9204905 W US 9204905W WO 9222535 A1 WO9222535 A1 WO 9222535A1
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Prior art keywords
ion pair
alkyl
bisimidazoline
pair complex
acids
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PCT/US1992/004905
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English (en)
French (fr)
Inventor
Michael Peter Siklosi
Charles Albert Hensley
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The Procter & Gamble Company
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Publication of WO1992022535A1 publication Critical patent/WO1992022535A1/en

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    • 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
    • C11D1/65—Mixtures of anionic with cationic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • C07D233/08—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms
    • C07D233/12—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D233/16—Radicals substituted by nitrogen atoms
    • 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
    • C11D1/58—Heterocyclic 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
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/04—Carboxylic acids or 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
    • C11D1/04—Carboxylic acids or salts thereof
    • C11D1/08—Polycarboxylic acids containing no nitrogen or 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
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • 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
    • C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic compounds

Definitions

  • This invention relates to bisimidazoline ion pair complexes which are used as fabric softening agents.
  • the ion pair complexes are used with or without cosoftening agents usually in an aqueous fabric softening composition to treat fabrics during the rinse cycle of laundering operations.
  • the composition can be substantially concen ⁇ trated.
  • Liquid fabric softening compositions have long been known in the art and are widely utilized by consumers during the rinse cycles of laundry operations. To satisfy the consumer's need for convenience and the growing environmental concerns, there is an increasing need for fabric softening agents that can be used in concentrated formulas with equivalent softening performance.
  • This invention discloses fabric softening agents which have excellent softening performance, and which can be formulated into a substantially concentrated aqueous fabric softening composition.
  • Fabric softeners impart a smooth, pliable, and fluffy texture to laundered fabrics. Consumers tend to prefer fabric softeners which give more softness.
  • fabric softening refers to a process whereby a desirably soft and fluffy appearance is imparted to fabrics. The practical methods of how to measure softness are explained in the examples.
  • rinse-added fabric softening compositions contain, as the active component, substantially water-insoluble cationic materials having two long alkyl chains. Typical of such materials ar ditallow dimethyl ammonium chloride, and imidazoliniu complexe substituted with two tallow groups.
  • Other compounds known for having excellent softening performance are bisi idazolines. These compounds are disclosed in U.S. Patents 3,855,235 (issued Dec. 17, 1974), 3,887,476 (issued June 3, 1975), and 3,898,244 (Aug. 5, 1975).
  • these bisimidazoline compounds are highly viscous even in conventionally prepared products, and thus difficult to incorporate into concentrated products.
  • the term "conventional product” refers to fabric softening products having about 5% to 8% active softening agent concentration, whereas "concentrated product” has higher concentrations, usually 2 to 3 times this level.
  • Another method is to "ion pair" the fabric softening agent, forming a complex which is easily dispersed in water.
  • the term “ion pair” is used for situations where the fabric softening agents, usually amines, are dispersed with any kind of anion such as surfactant fatty acids, thus creating an ammonium/anion pair.
  • U.S. Patent No. 4,756,850 discloses dryer-added fabric conditioning articles and methods utiliz ⁇ ing imidazoline-anionic surfactant ion pair complexes as fabric condi ⁇ tioning agents.
  • the composition containing these actives are commin ⁇ gled with the fabrics and provide a soft, antistatic finish concurrent ⁇ ly with the drying operation.
  • U.S. Patent No. 4,915,854 (issued Apr. 10, 1990) discloses an amine-anionic compound ion pair complex particles having an average particle diameter of from about 10 microns to about 300 microns. These particles provide excellent through-the-wash softening without signifi ⁇ cantly impairing cleaning performance.
  • U.S. Patent No. 4,915,854 discloses that ion pair particles which are made from lower chain length amines impart improved processing characteristics and improved chemical stability in liquid detergents.
  • ion pairs are basically stoichiometric; i.e., the amine and anion pairs are on a 1:1 basis.
  • A A bisimidazoline of the formula
  • Rl Rl wherein n is 2 - 4 and Rl is independently selected from C6-22 alkyl groups;
  • Organic acids selected from the group consisting of carboxylic acids having a C6-22 alkyl or C7-C22 alkyl aryl chain, alkyl or alkyl aryl sulfonic acids having a Ci-22 alkyl chain, dicarboxylic acids having a C2-C8 alkyl chain, and mixtures thereof;
  • the ion pair complex is included in an aqueous fabric softening composition at a concentration up to about 23%, wherein optionally viscosity controlling agents are added to the composition.
  • the ion pair complex can be mixed with cosofteners to provide a composition with excellent fabric softening performance wherein the bisimidazoline in the ion pair complex is more than 25% by weight of the total softening active agents.
  • the components of the unique non-stoichiometric ion pair complex and the method of ion pairing of the present invention are described in detail below. Further described are the preferred compositions for the ion pair complex as fabric softening agents and optional ingredients such as cosofteners.
  • the bisimidazoline compounds can be prepared by the reaction of a higher fatty acid with a polya ine.
  • polyamines are those having the following structural formula; NH2CH2CH2NH(CH2) n NHCH2CH2NH2 wherein n is 2 - 4, preferably 2.
  • the preferred polyamine is triethylenetetra ine.
  • the bridge portion (CH2)n of the bisimidazoline compound should not be longer than propyl, for longer chains are thought to cause physicochemical property problems.
  • the bridge also should not include nitrogen (N), for those derivatives are thought to cause yellowing when applied to fabrics.
  • the Rl substituent of the respective imidazoline rings represents the alkyl group attached to the carboxyl group of the fatty acid from whence it is derived. Accordingly, when a mixture of fatty acids is used, the R 1 substituent collectively represents the mixture of alkyl residues associated with carboxyl groups of said fatty acids.
  • fatty acids include; caproic, caprylic, capric, lauric, myristic, yristoleic, palmitic, pal itoleic, stearic, oleic, elaidic, ricinoleic, linoleic, linolenic, eleostearic, arachidonic, behenic, and erucic acid.
  • the fatty acids can be derived from naturally occurring or synthetic fatty acids.
  • Suitable sources of naturally occurring fatty acids include tallow fatty acids, corn oil fatty acids, cottonseed oil fatty acids, peanut oil fatty acids, soybean oil fatty acids, canola oil fatty acids (i.e. fatty acids derived from low erucic acid rapeseed oil), sunflower seed oil fatty acids, sesame seed oil fatty acids, safflower oil fatty acids, palm kernel oil fatty acids, palm oil fatty acids, and coconut oil fatty acids.
  • the fatty acids can be saturated or unsaturated, including positional or geometrical isomers, e.g., cis- or trans-isomers.
  • Preferred fatty acids are oleic acid, tallow acid, hardened tallow acid and mixtures thereof.
  • the fatty acid reactant can take the form of a free fatty acid, an alkyl ester thereof or the naturally occurring glyceride esters.
  • the glyceride ester form of the fatty acid will readily split in the course of the initial condensation of the acid and the polyamine reactant and the glycerol by-product can be removed from the reaction mixture.
  • triglycerides which can be used to prepare the bisimidazolines of this invention: Animal fats such as lard, tallow, oleo oil, oleo stock, oleo stearin and the like, which are solid at room temperature can be utilized as a mixture with liquid oils. Also, liquid oils, e.g., unsaturated vegetable oils, can be used. These oils can be partially hydrogenated to convert some of the unsaturated double bonds of the fatty acid constituents into saturated bonds.
  • Vegetable oils include unhydrogenated or partially hydrogenated soybean oil, hazelnut oil, linseed oil, olive oil, peanut oil, canola oil, coconut oil, safflower oil, rapeseed oil, cottonseed oil, corn oil and sunflower seed oil can also be used herein.
  • Solid vegetable oils useful herein include palm oil, palm kernel oil, cocoa butter and hydrogenated vegetable oils.
  • low molecular weight synthetic fats which are certain tri- or diglycerides in which one or two of the hydroxyl groups of the glycerine have been esterified with acetic, propionic, butyric or caprionic acids and one or two of the remaining hydroxyl groups of the glycerine have been esterified with higher molecular weight fatty acids having from 12 to 22 carbon atoms.
  • Other common types of triglycerides include: cocoa butter and cocoa butter substitutes, such as shea and illipe butter; milk fats, such as butter fat; and marine oils which can be converted into plastic or solid fats such as menhaden, pilcherd, sardine, whale and herring oils.
  • Preferred triglycerides include partially hydrogenated and unhydrogenated animal or vegetable oils which are liquid or semi-solid at room temperature, and the like.
  • fatty acids are substantially saturated, as unsaturated fatty acids tend to oxidize.
  • the next step in deriving the bisimidazolines involves cyclizing the polyamido amine. This reaction is accomplished by heating the polyamido amine at a temperature between about 125°C and 250°C under vacuum from 1 to 300 mm Hg.
  • the extent of cyclization can be noted by analyzing tertiary amine content, generally referred to as the TAN value of the reaction mixture. The extent of. cyclization is an important factor, for remaining acylic amines can cause yellowing and malodor when applied to fabrics.
  • the most preferred bisimidazoline compound (1-ethylene bis [2-hydrogenated tallow imidazoline]) is commercially available from Sherex Co., Dublin, OH, in the form of free amine.
  • the organic acids, component B, used for ion pairing the bisimidazoline compound, component A are selected from a variety of acids.
  • the group of acids consists of carboxylic acids with a C ⁇ -22 alkyl or C7-C22 alkyl aryl chain, alkyl or alkyl aryl sulfonic acids having a Ci-22 alkyl chain, dicarboxylic acids having a C2-8 alkyl chain, and mixtures thereof.
  • Ion pair complexes made of any of the above mentioned acids can be used to formulate a fabric softening composition of 5%-8% active component concentration when further reacted with component C, the Bronstedt acid.
  • the preferred acids are C ⁇ -18 alkyl fatty acids, C ⁇ -3 alkyl sulfonic acids, and C -i ⁇ alkyl aryl sulfonic acids.
  • the ion pairs made with these acids can be formulated up to 18% concentration.
  • Most preferred acids are C ⁇ -12 carboxylic acids and methanesulfonic acid. Ion pairs made of these acids can be formulated up to 23% concentration in the compositions herein.
  • the ratio of the bisimidazoline compounds and organic acids is a key factor of the present invention. It is known that the ion pairing of bisimidazoline compounds with organic acids reduces the viscosity of the original bisimidazoline.
  • the Bronstedt acid useful for completing the ion pairing are those having a pKa value of not greater than 6, provided that the pH of a dispersion of the acid is not greater than 5. These acids stabilize the electric charge of the ion pair structure obtained by the bisimidazoline compounds and organic acids, resulting in a unique non-stoichiometric ion pair complex. These Bronstedt acids also contribute in keeping the ion pair complex within a certain pH range, which is also critical for stabilization.
  • Preferred Bronstedt acids are HC1, HBr, H2SO4, H3PO4, formic acid, acetic acid, methanesulfonic acid, and ethanesulfonic acid. Most preferred is HC1.
  • the Ion Pair Complex is prepared by combining the above mentioned components A, B, and C at a non-stoichiometric mole ratio, wherein A : B : C is from about 1.0 : 1.8 : 1.4 to about 1.0 : 0.1 : 2.0, when component B is a monoacid, and from about 1.0 : 0.9 : 1.4 to about 1.0 : 0.1 : 2.0 when component B is a diacid.
  • the preferred ratio is about 1.0 : 0.5 : 2.0 for monoacids and 1.0 : 0.25 : 2.0 for diacids.
  • the ion pair complex is prepared by first melting component A, bisimidazoline, followed by addition of melted component B, organic acid, followed by the addition of the combined A and B components to an aqueous solution of component C, Bronstedt acid.
  • the bisimidazoline is heated to slightly above its melting point in a vessel equipped with a stirrer or other mixing device.
  • the organic acid is added to the bisimidazoline as a liquid melt, slowly with stirring. In general, temperatures of from 80°C to 120°C are used for this stirring process.
  • a nitrogen or other inert gas purge can be used to prevent hydrolysis and/or oxidation.
  • the bisimidazoline-organic acid mixture is formed.
  • cosoftener When a cosoftener is used, it is preferably mixed with the melted bisimidazoline-organic acid mixture before adding them to the Bronstedt acid.
  • the cosofteners are solid at room temperature and thus are easier to incorporate if they are melted and mixed after the bisimidazoline-organic acid mixture is formed.
  • the bisimidazoline-organic acid mixture or optionally the mixture of bisimidazoline-organic acid and cosoftener as obtained above is then added to the Bronstedt acid aqueous solution of component C.
  • the Bronstedt acid is usually at a concentration of from about 0.3% to about 10% in water. The exact amount of water used and of the acid depends upon the particular ratio of ion pair complex to be formed, the pH of the ion pair complex and the final concentration of the softener composition.
  • the ion pair complex of the present invention is unique in that it is non-stoichiometric.
  • the stoichiometric ratio of the bisimidazoline to organic acids is 1 : 2 since there are two secondary amines present in each molecule of the bisimidazoline. These amines are thought to react with the acids.
  • diacids are used for component B, one molecule of diacid is believed to react with two amine sites, and therefore included by half the ratio of monoacids.
  • components B and C are thought to pair with the two secondary amines, forming in part an ion pair of the following formula; (CH 2 )2 (CH 2 )2 / ⁇ / ⁇ Y- H-N N-H—-X"
  • HX component B (in case it is a monoacid)
  • HY component C
  • the non-stoichiometric ion pairing would render a mixture of free, partially, and fully ion paired bisimidazolines, which as a whole is regarded as the ion pair complex in the present invention.
  • the ion pair complex thus obtained is useful for treating textiles, especially fabric softening.
  • the ion pair complex is stable and flowable in a pH range of 2.5 - 4, preferably about 3.5.
  • Another important factor for stabilizing and dispersing the ion pair complex is the particle size.
  • the desired particle sizes can be achieved by use of in-line high shear mixing instruments such as the Tekmar Mill produced by the Ika-Works Co., Cincinnati, OH.
  • the ideal particle made from an ion pair complex is sufficiently small so as to be readily dispersed when formulated in an aqueous fabric softening composition.
  • Preferably more than 80% of the ion pair complex has a particle size smaller than about 5 microns, more preferably smaller than about 1 micron.
  • the ion pair complex can also be processed to larger particles and appl ied to a dispensing means for release to fabrics in the dryer operation.
  • compositions may include the ion pair complex particles as the only fabric softening agent, or combined with cosofteners.
  • the active components of the composition are primarily fabric softening agents, but may also include ingredients such as those disclosed herein, and may include other ingredients not specifically listed herein.
  • Preferred compositions contain cosofteners.
  • cosofteners are added in order to enhance softening performance.
  • the cosofteners are restricted to those which are solid at room temperature, for cosofteners of such nature are known to increase softening performance.
  • quaternary ammonium salts and fatty acid esters are tallow substituted quaternary ammonium salts such as those known as MTTMAC (monotallow trimethyl ammonium chloride) and DTDMAC (ditallow dimethyl ammonium chloride) are well known in the art as fabric softener agents usually formulated in liquid compositions.
  • MTTMAC monotallow trimethyl ammonium chloride
  • DTDMAC disitallow dimethyl ammonium chloride
  • Another type is the fatty acid esters of sorbitan or glycerol. Sorbitan monostearate is most pre ⁇ ferred among this type. This type is well known in the art as dryer- added fabric softening agents in sheet form. Among those mentioned above, DTDMAC is the most preferred.
  • the ratio of the ion pair complex to the cosoftener is al so important to softening performance.
  • the preferred ratio of the ion pair compound is wherein the ion pair complex is more than 25% by weight of the total active softening agents, preferably wherein the bisimidazoline in the ion pair complex to cosoftener is about 1.6 : 1 to about 2 : 1 by weight.
  • a viscosity controll ing agent is usually present in the composi ⁇ tion at a level not more than about 2.5%, especially when a concentrated formula is prepared. Viscosity controll ing agents can be organic or inorganic in nature.
  • organic viscosity controll ing agents are fatty acids and esters such as fatty acid esters of sorbitan or glycerol , fatty alcohols, water-mi scible solvents such as short chain alcohols and ammonium salts such as TTMMAC (tritallow monomethyl ammonium chloride) obtained as Adogen 440 (Sherex Co. ) .
  • inorganic viscosity control agents are water-soluble ionizable salts. A wide variety of ionizable salts can be used. Examples of suitable salts are the hal ides of the group IA and IIA metal s of the Periodic Table of the Elements, e.g.
  • the ionizable salts are particularly useful during the process of mixing the ingredients to make the compositions herein, and later to obtain the desired viscosity.
  • TTMMAC is preferred to be included when tallow substituted quaternary ammonium salts are contained as cosofteners in the composition at a substantially concentrated level .
  • the amount of viscosity controlling agents used depends on the level of active ingredients used in the compositions and can be adjusted according to the desire of the formul ator.
  • the viscosity controll ing agent is usually included in the formula in a flowable form either concurrently with or after the combined A and B components are added to an aqueous solution of component C.
  • the present compositions can contain sil icones to provide addi - tional benefits such as ease of ironing and improved fabric feel .
  • the preferred silicones are polydimethylsiloxanes at a viscosity of from about 100 centistokes (cs) to about 100,000 cs, preferably from about 200 cs to about 60,000 cs. These silicones can be used as is, or they can be conveniently added to the softener compositions in a preemulsified form which is obtainable directly from the suppliers.
  • silicones examples include 55% emulsion of polydimethylsiloxane (350cs) sold by Dow Corning Corporation under the trade name DOW CORNING 1157 Fluid and 50% emulsion of polydimethyl : siloxane (10,000cs) sold by General Electric Company under the trade name General Electric R SM 2140 Silicones.
  • the optional silicone component can be used in an amount of from about 0.1% to about 6% by weight of the composition.
  • silicone can be contained as antifoa ing agents. Examples of such is the 20% emulsion of DOW CORNING 1520 FLUID available from Dow Corning. This silicone can be used in an amount of from about 0.005% to about 0.05% of the composition.
  • short chain alcohols such as ethanol and isopropanol which are often present in the commercially available quaternary ammonium compounds used as cosofteners.
  • the short chain alcohols are normally present at less than about 3% by weight of the composition when quaternary ammonium compounds are selected as a cosoftener.
  • ingredients can be added to the composition herein for their known purposes.
  • Such ingredients include, but are not limited to, perfumes, emulsifiers, preservatives, antioxidants, bacteriocides, fungicides, colorants, dyes, fluorescent dyes, brighteners, opacifiers, freeze-thaw control agents, shrinkage control agents, and agents to provide ease of ironing.
  • perfumes emulsifiers
  • bacteriocides fungicides
  • colorants fungicides
  • dyes e.g., fungicides
  • dyes e.g., fungicides
  • colorants e.g., fungicides, colorants, dyes, fluorescent dyes, brighteners, opacifiers, freeze-thaw control agents, shrinkage control agents, and agents to provide ease of ironing.
  • dyes emulsifiers
  • fungicides fungicides
  • colorants fungicides
  • dyes e.g., fungicides
  • the aqueous fabric softening compositions of the present invention can be prepared by conventional methods.
  • a convenient and satisfactory method is to prepare the softening active pre ix of the ion pair complex and cosoftener at about 100°C.
  • the premix is injected into a heated aqueous solution of the Bronstedt acid, and mixed with agitation and high shearing, if the latter is necessary to achieve a certain particle size.
  • Ingredients such as viscosity controlling agents can be added in the Bronstedt acid solution while mixing with the active premix, or can be added after the injection is completed.
  • TTMMAC When TTMMAC is to be incorporated in the formula as a viscosity controlling agent, it is usually co elted with the softening active premix prior to mixing with the Bronstedt acid solution. Temperature-sensitive optional ingredients can be added after the fabric softening composition is cooled to a lower temperature.
  • the aqueous fabric softening compositions of this invention are usually used by adding to the rinse cycle of conventional home laundry operations. Generally, rinse water has a temperature of from about 5° to about 30°C.
  • the concentration of the fabric softener actives of this invention is generally from about 10 ppm to about 200 ppm, prefer- ably from about 25 ppm to about 100 ppm by weight of the aqueous rinsing bath.
  • the present invention in its fabric softening method aspect comprises the steps of (1) washing fabrics in a conventional washing machine with a detergent composition; and (2) rinsing the fabrics in a bath which contains the above-described amounts of the fabric softeners; and (3) drying the fabrics.
  • the fabric softening composition is preferably added to the final rinse. Fabric drying can take place either in an automatic dryer or in the open air.
  • DTDMAC a blend of di (hydrogenated) tallow dimethyl ammonium chloride, onotal low tri ethyl ammonium chloride, and ethanol in a nominal ratio of 76: 11 :13.
  • Adogen 440 blend of tri tal low mono ethyl ammonium chloride (TTMMAC) and isppropanol at a nominal ratio of 80:20.
  • Kathon a blend of tri tal low mono ethyl ammonium chloride (TTMMAC) and isppropanol at a nominal ratio of 80:20.
  • Example I contains as fabric softening active 7.0% of DTDMAC and the reaction product of 14.0% of bisimidazoline and 1.63% of octanoic acid and 1.65% of HCl.
  • the mole ratio of bisimidazoline : octanoic acid : HCl is 1.0 : 0.5 : 2.0. It is prepared as follows: about 14.0 parts of molten bisimidazoline (melted under a dry nitrogen purge to prevent hydrolysis) is added to a heated premix vessel. To this, 1.69 parts of octanoic acid is added slowly and the mixture is stirred for 5 minutes.
  • Example II contains as fabric softening active 8.7% of sorbitan monostearate and the reaction product of 14.3% of bisimidazoline and 1.67% of octanoic acid and 1.69% of HCl.
  • the mole ratio of bisimida ⁇ zoline : octanoic acid : HCl is 1.0: 0.5 : 2.0. It is prepared as follows : About 14.3 parts of molten bisimidazoline (melted under a dry nitrogen purge to prevent hydrolysis) is added to a heated premix vessel. To this, 1.67 parts of octanoic acid is added slowly and the mixture is stirred for 5 minutes.
  • Example III contains as fabric softening active 2.5% of DTDMAC and 15 the reaction product of 5.0% of bisimidazoline and 0.58% of octanoic acid and 0.6% of HCl.
  • the mole ratio of bisimidazoline : octanoic acid : HCl is 1.0: 0.5 : 2.0. It is prepared as follows : About 5.0 parts of molten bisimidazoline (melted under a dry nitrogen purge to prevent hydrolysis) is added to a heated premix vessel. To this, 0.58 parts of 20 octanoic acid is added slowly and the mixture is stirred for 5 minutes.
  • Example IV contains as fabric softening active 2.5% of DTDMAC and
  • Example V contains as fabric softening active 7.5% of DTDMAC. It is prepared as follows: About 9.0 parts of molten DTDMAC is added to a heated premix vessel maintained at 100°C and stirred for 1 minute. The premix is then added with agitation, to a mix vessel containing deionized water and 0.032 parts of HCl solution which had been heated to 57°C. At this point, CaCl2 solution can be added for viscosity control, if needed. This is followed by addition of 0.025 parts of Tenox S-l, and 0.033 parts of Kathon. The mixture is cooled to 43°C with continued agitation and addition of perfume and 0.005 parts of DC 1520 fluid.
  • Deionized Water Example VI contains as fabric softening active 15.0% of DTDMAC. It is prepared as follows: About 18.1 parts of molten DTDMAC is added to a heated premix vessel maintained at 100°C and stirred for 1 minute. The premix is then added, with agitation, to a mix vessel containing
  • Example VII contains as fabric softening active 7.7% of DTDMAC and the reaction product of 15.3% of bisimidazoline and 1.07% of octanoic 0 acid and 1.81% of HCl.
  • the mole ratio of bisimidazoline : octanoic acid : HCl is 1.0 : 0.3 : 2.0. It is prepared as follows: About 15.3 parts of molten bisimidazoline (melted under a dry nitrogen purge to prevent hydrolysis) is added to a heated premix vessel. To this, 1.07 parts of octanoic acid is added slowly and the mixture is stirred for 5 5 minutes.
  • a total of 1.1 kg of fabric composed of 0.2 kg test fabrics (6-100% cotton terry face cloths) and 0.9 kg of ballast fabrics (8-U.S. cotton medium t-shirts) are placed in twin tub washers (National W102) at normal agitation setting with 25g of powder laundry detergent (Attack, Kao Co.).
  • a total of 30 liters of 20°C water (3 grains/gallon hardness, Ca/Mg ratio 3/1) is added, followed by the test fabrics and ballast fabrics.
  • the wash cycle is started and is allowed to proceed for 10 minutes, after which the fabric is transferred to the spinner compartment and spun for 2 minutes.
  • the fabric is transferred back to the main washer compartment, and is rinsed for 10 minutes using an overflow rinse with a water flow rate of 9 liters/minute.
  • the fabric is transferred again to the spinner compartment and spun for 2 minutes.
  • 30 liters of 3 grain/gallon water is added, the agitator is started, and the fabric softener is added.
  • the fabrics from the spinner are placed in with the fabric softener, and are rinsed with agitation for 3 minutes.
  • the amount of fabric softener added depends on the concentration of the fabric softeners used.
  • the in-rinse is 50 ppm of softener actives, i.e., bisimidazoline ion pair complex or bisimidazoline ion pair complex plus cosoftener, depending on the system being studied.
  • the active agent of the ion pair complex here is calculated on the bisimidazoline basis.
  • the fabrics are placed back in the spinner for two minutes.
  • the terries are then removed from the spinner and line dried on a clothes rack overnight. They are graded blind the following day for softness by expert judges. The following scale is used:
  • Table VIII shows the results for the softening performance of compositions prepared in Examples I and II compared to Example VI, and Examples III and IV compared to Example V.
  • DTDMAC which is adequately formulated into a practical composition in Examples V and VI
  • a procedure of 2 to 4 cycles of wash, rinse, soften, dry and grade were used.
  • a positive PSU value indicates that the given composition softened better than the standard DTDMAC control compositions, Examples V and VI, which for simplicity is normalized to 0.0 PSU.
  • compositions prepared in Examples I, II, III and IV of the present invention show superior softening activity and are statistically significant at the 95% confidence level for each cycle tested, compared with Example V or VI, as indicated.

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  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
PCT/US1992/004905 1991-06-19 1992-06-11 Fabric softening agents and compositions thereof WO1992022535A1 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US71756391A 1991-06-19 1991-06-19
US717,563 1991-06-19
US74830491A 1991-08-21 1991-08-21
US748,304 1991-08-21

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AU (1) AU2266592A (enrdf_load_stackoverflow)
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MX (1) MX9203013A (enrdf_load_stackoverflow)
NZ (1) NZ243195A (enrdf_load_stackoverflow)
PT (1) PT100612A (enrdf_load_stackoverflow)
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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994001523A1 (en) * 1992-07-06 1994-01-20 Unilever Plc Fabric conditioning compositions and process for making them
US5470986A (en) * 1994-06-27 1995-11-28 E. I. Du Pont De Nemours And Company Imidazolium hardeners for hydrophilic colloid
US7371718B2 (en) * 2005-04-22 2008-05-13 The Dial Corporation Liquid fabric softener
WO2015100032A1 (en) * 2013-12-27 2015-07-02 Dow Global Technologies Llc Textile treatment compositions including quternary bis-imidazoline compounds derived from linear tetramines useful to improve moisture management and provide antimicrobial protection

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2360723A1 (de) * 1972-12-15 1974-06-20 Ciba Geigy Ag Verfahren zum flammfestmachen von organischem fasermaterial
US4756850A (en) * 1987-06-10 1988-07-12 The Procter & Gamble Company Articles and methods for treating fabrics

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2360723A1 (de) * 1972-12-15 1974-06-20 Ciba Geigy Ag Verfahren zum flammfestmachen von organischem fasermaterial
US4756850A (en) * 1987-06-10 1988-07-12 The Procter & Gamble Company Articles and methods for treating fabrics

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994001523A1 (en) * 1992-07-06 1994-01-20 Unilever Plc Fabric conditioning compositions and process for making them
US5470986A (en) * 1994-06-27 1995-11-28 E. I. Du Pont De Nemours And Company Imidazolium hardeners for hydrophilic colloid
US5591863A (en) * 1994-06-27 1997-01-07 Sterling Diagnostic Imaging, Inc. Imidazolium hardeners for hydrophilic colloids
US7371718B2 (en) * 2005-04-22 2008-05-13 The Dial Corporation Liquid fabric softener
WO2015100032A1 (en) * 2013-12-27 2015-07-02 Dow Global Technologies Llc Textile treatment compositions including quternary bis-imidazoline compounds derived from linear tetramines useful to improve moisture management and provide antimicrobial protection
JP2017502178A (ja) * 2013-12-27 2017-01-19 ダウ グローバル テクノロジーズ エルエルシー 湿気管理の改善及び抗菌保護の提供に有用な直鎖状テトラミンに由来するクターナリー（ｑｕｔｅｒｎａｒｙ）ビス−イミダゾリン化合物を含む織物処理組成物
US10428454B2 (en) 2013-12-27 2019-10-01 Dow Global Technologies Llc Textile treatment compositions including quternary bis-imidazoline compounds derived from linear tetramines useful to improve moisture management and provide antimicrobial protection

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CN1069788A (zh) 1993-03-10
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PT100612A (pt) 1993-09-30
NZ243195A (en) 1995-07-26
IE921974A1 (en) 1992-12-30
TR25990A (tr) 1993-11-01
AU2266592A (en) 1993-01-12

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