WO2003060047A1 - Formulation d'adoucisseur liquide pour tissu comprenant des colorants rouges a base d'hemicyanine - Google Patents

Formulation d'adoucisseur liquide pour tissu comprenant des colorants rouges a base d'hemicyanine Download PDF

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Publication number
WO2003060047A1
WO2003060047A1 PCT/US2003/000792 US0300792W WO03060047A1 WO 2003060047 A1 WO2003060047 A1 WO 2003060047A1 US 0300792 W US0300792 W US 0300792W WO 03060047 A1 WO03060047 A1 WO 03060047A1
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WIPO (PCT)
Prior art keywords
fabric
liquid
fabric softener
red
colorant
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Application number
PCT/US2003/000792
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English (en)
Inventor
James E. Stavrakas
Original Assignee
Milliken & Company
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
Priority claimed from US10/047,061 external-priority patent/US6638903B2/en
Priority claimed from US10/047,050 external-priority patent/US6593289B1/en
Application filed by Milliken & Company filed Critical Milliken & Company
Priority to AU2003217193A priority Critical patent/AU2003217193A1/en
Priority to JP2003560134A priority patent/JP4444658B2/ja
Priority to DE60321126T priority patent/DE60321126D1/de
Priority to EP03713229A priority patent/EP1465970B1/fr
Priority to BRPI0306896-0A priority patent/BR0306896B1/pt
Publication of WO2003060047A1 publication Critical patent/WO2003060047A1/fr

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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
    • 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
    • C11D1/38—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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/40—Dyes ; Pigments

Definitions

  • This invention relates to fabric softener compositions comprising certain red colorants that exhibit excellent deep, dark red colorations (for aesthetic purposes) and mix very well with other colorants to provide differing red shades and tints therein, which simultaneously exhibit very low, if any staining capabilities on fabrics treated therewith.
  • Such deep and dark red colorations have heretofore been unavailable within fabric softener formulations due to the tendency of such prior colorants to exhibit unacceptable staining levels, particularly when formulated at similar deep and dark shades as now provided within the inventive low-staining formulations.
  • the colorants present therein interact favorably with quaternary ammonium salt softening agents in a manner to prevent reaction with the fibers of the treated fabrics themselves, thereby preventing staining thereon and therein.
  • Such novel red-colored or -tinted fabric softener formulations, as well as any other quaternary-ammonium salt-containing red-colored or -tinted compositions are encompassed within this invention.
  • Fabric softeners have been provided as colored formulations for aesthetic reasons and brand identity. Although white and/or clear compositions have been commercialized in the past as well, the modern consumer often prefers attractively colored cleaning, etc., products.
  • Fabric softener compositions are known in the art and are used in rinse cycles of automatic laundry operations to impart improved hand and anti-static properties to laundered fabrics.
  • the first U.S. concentrated (6-10% active) rinse cycle fabric softener was introduced in the 1960s. These were added during the final rinse of the wash cycle and were usually quaternary types, mainly di(hydrogenated) tallow dimethylammonium chloride
  • DHTDMAC DHTDMAC
  • the products were essentially aqueous solutions or suspensions containing 4-6% active softener, a fabric substantive fragrance and a viscosity modifier.
  • Colorants are generally added to liquid fabric softening compositions for visual appeal to the consumer as well as identity of the product.
  • Fabric staining caused by softener compositions can be permanent; however, initial staining may not always be obvious to the consumer due to potentially and relatively low levels of discoloration during individual laundry cycles. Thus, staining may actually accumulate on target fabrics over a period of time rather than during a single wash.
  • Colorants employed in fabric softener compositions are preferably those which are easily removed from fabric if color staining, or possibly staimng due to softener compounds themselves, occurs. Such colorants thus must exhibit a very low and reduced tendency to stain commonplace fabrics such as cotton and polyester. Dyes of high color stability in the fabric softener compositions which exhibit minimal complexation or reaction with other fabric softener ingredients and the laundered fabrics themselves are of particular interest in fabric softener composition applications. Among these dyes are certain polymer-bound colorants which are available from Milliken Chemical Co.
  • Liquitint® colorants whose incorporation in liquid fabric softening compositions is noted in published international application WO 94/10285 as well as direct dyes, acid dyes, F,D & C Dyes (e.g., Red 40), rhodamines, pigments, and the like, which impart red colorations to liquid softener formulations, but also have a tendency to stain targeted fabrics, particularly when present at levels that provide deep and dark red shades.
  • red colorants providing deep and dark red shades, specifically at high L, c, and h values as noted below, within fabric softening compositions have been unavailable to the industry without also exhibiting unacceptable staining levels.
  • red colorants are stable in low pH (e.g., from about 1 to 4) cationic compound-containing liquid formulations, non-staining, and capable of high color loading and bright coloration without precipitating out of the composition, particular, colorants are desired which provide an increase in the ease of stain removal versus the aforementioned commonly used red colorants and dyes within liquid fabric softener compositions.
  • the red colorants traditionally introduced within liquid fabric softener formulations simply cannot provide the low staining properties with simultaneously the aforementioned aesthetically desirable deep and dark red shades or, alternatively, the ability to thoroughly mix with other colorants to provide pink or reddish shades or tints within the target liquid composition.
  • a standard laundry procedure e.g., either by hand or within a tumble, rotary, or other type of washing machine.
  • a further object of the invention is to provide a liquid fabric softener formulation that will not exhibit any appreciable staining on target substrates and thus only provides red colorations within and to the target liquid fabric softener composition.
  • Yet another object of this invention is to provide a red colorant that provides color in the presence of cationic softener compounds but will not appreciably react with fiber constituents of target fabrics. Accordingly, this invention is directed to a fabric softener composition comprising at least one fabric softening component and at least one red colorant that provides excellent high color space characteristics and exhibits a simultaneously low tendency to stain target fabrics, as well as the use of such compositions for conditioning fabrics in an aqueous wash.
  • this invention relates to a liquid fabric softener composition
  • a liquid fabric softener composition comprising a hemicyanine colorant, preferably having an electrophilic reactive group reacted with a poly(oxyallylene)-containing moiety having a nucleophilic reactive group to provide a polymeric colorant.
  • the present invention thus encompasses a liquid fabric softener composition
  • a liquid fabric softener composition comprising at least one cationic fabric softener compound and at least one water-soluble red hemicyanine derivative colorant, preferably a polymeric derivative of such a colorant, either as the sole colorant to provide a red hue, or as a component within a mixture of colorants to provide.any number of different hues.
  • this invention encompasses a liquid fabric softener composition
  • a liquid fabric softener composition comprising at least one cationic fabric softener compound and at least one red colorant, wherein said liquid fabric softener composition exhibits a red color characterized by a color space in terms of CIELAB values under D65 illumination of an L* value of at least 30, an a* value of at least 20, a b* value of between -20 and 20, a C* value of at least 20, and an h° of between 0 and 30° and 300° and 360, wherein said red-colored liquid fabric softener exhibits a stain level of at least 4 upon contact with a 100% terry cotton fabric substrate pursuant to the AATCC Gray Scale For Evaluating Staining.
  • this invention encompasses a red colorant that exhibits a color space in terms of CIELAB values under D65 illumination of an L* value of at least 30, an a* value of at least 20, a b* value of between -20 and 20, a C* value of at least 20, and an h° of between 0 and 30° and 300° and 360, and exhibits a stain level of at least 4 upon contact with a 100% terry cotton fabric substrate pursuant to the AATCC Gray Scale For Evaluating Staining when present within a liquid composition comprising at least 3% by weight of a specific quaternary arnmonium cationic fabric softener compound (either Accosoft® 501 or 808, as listed below).
  • a specific quaternary arnmonium cationic fabric softener compound either Accosoft® 501 or 808, as listed below.
  • this invention encompasses a method of treating fabrics within a rinse cycle of a standard laundering method within a rotary washing machine comprising the steps of a) providing a liquid fabric softener composition as discussed above; b) providing at least one target fabric substrate within said rotary washing machine; and c) introducing, at a point in time after said at least one target fabric substrate has been subjected to a cleaning stage within a standard laundering process within said rotary washing machine, preferably during the rinse cycle of said process, said liquid fabric softener in an amount sufficient to impart softening characteristics to said target fabric.
  • inventive colorants have unexpectedly been found to function very well in solution with low pH, cationic fabric softener compounds. To that end, such colorants have been found to provide the above-delineated highly desirable color space characteristics to permit deep and dark red colorations within target liquid fabric softener formulations.
  • such colorants being polymeric in nature, preferably, exhibit very low, if no, staining properties of fabrics when utilized in combination with such cationic softener compounds.
  • fabrics as cotton, polyester, poly/cotton blends, nylon, and the like, can be treated (such as, for example, during the rinse cycle of a standard rotary laundering procedure) with liquid fabric softeners comprising such red colorants and not exhibit any appreciable staimng caused thereby.
  • Such colorants are thus very compatible with the cationic (e.g., for example, quaternary ammonium) compounds required of such fabric softener compositions, and also exhibit compatibility with standard fragrances and preservatives, as merely examples, without complexing or destabilizing the resultant mixture.
  • inventive colorants can withstand the presence of quaternary ammonium compounds (as well as the associated pH levels imparted thereby, particularly between 1 and 4) and thus can be utilized in any liquid media comprising quaternary ammonium compounds, primarily, as noted throughout, fabric softener compositions, but also, to a lesser but possible extent, certain cleaning solutions, antistatic sprays, and the like.
  • inventive colorants produce true solutions and not emulsions nor dispersions, the formulations made therefrom are homogeneous (not clear) and brilliant in appearance, and can easily mix with other colorants, including traditional red colorants (as well as others) to form different non-staining colorations, shades, tints, etc. (such as pink, orange, purple, and the like), within target formulations.
  • inventive colorants and thus formulations made therewith also exhibit excellent light fastness, particularly over a long shelf life.
  • the color space values will generally not become modified over time and upon exposure to standard fluorescent or incandescent lighting such that the desired colorations are retained for long periods of time.
  • the particular hemicyanine derivative colorant is polymeric in nature, and most preferably comprises poly(oxyalkylene) pendants groups thereon.
  • poly(oxyalkylene) groups are selected from polyethyleneoxy (EO), polypropyleneoxy (PO), and polybutyleneoxy (BO) groups, although longer chain monomers may also be utilized (up to about 18 carbons, for example).
  • these moieties are all EO groups, although combinations of EO and any of the others may be utilized as well.
  • Preferably from about 2 to about 200 moles of alkyleneoxy groups are present on each separate polyoxyalkylene pendant group; more preferably from about 2 to 50 moles; and still more preferably from about 5 to 25 moles, and most preferably about 20 moles.
  • polyoxyalkylene is intended to encompass any pendant group that includes at least two alkyleneoxy moieties.
  • R ⁇ is H or C ⁇ -C 20 alkyl
  • R 2 , R 3 , R , R 5 , R 6 , R , R 8 , R 9 , R ⁇ o,and R ⁇ are the same or different and are selected from the group consisting of H, -C 20 alkyl, -C2 0 alkoxy, C ⁇ -C 20 hydroxyl, amino, hydroxyl, and C ⁇ -C 20 carboxyl
  • R' is C ⁇ -C 16 alkyl
  • a is 0 — 200 and b is 0 - 200, wherein a+b ⁇ 3
  • X is H or COCH 3 ; and any counter ion may be present, such as, without limitation, OH " , Cl “ , CH 3 COO " , or HSO 4 " .
  • such a compound is present wherein Ri . and R 6 are methyl and the remaining R groups are hydrogen, and further wherein a is about 20, b is 0, X is COCH 3 , and the counter ion is OH " .
  • the water soluble polymeric hemicyanine derivative colorants are liquid in nature at ambient temperature and pressure and at substantial purity; however, pasty or waxy colorants (which are readily soluble in water) are also encompassed within this invention and may be added to fabric softener formulations, particularly in combination with viscosity modifying agents (such as, without limitation, calcium chloride) to provide the desired viscosity level (of between about 10 to about 1,500 cps to permit sufficient pourability).
  • viscosity modifying agents such as, without limitation, calcium chloride
  • ambient temperature and pressure means from about 20 to about 25°C at a pressure of from about 0.8 to about 1.2 atmospheres.
  • substantial purity means that the colorant is at least 90%> free from solvent, diluent, surfactant, and any other compound which may dilute the colorant compound.
  • the target inventive compositions will include at least one cationic, preferably quaternary ammonium, fabric softener compound, as well as other standard softener additives, such as resins, preservatives, pH adjusters, foam depressants, antistatic compounds, enzymes, bactericides, fungicides, stabilizers, and the like, in addition to at least colorant as defined above.
  • these additive compounds do not factor into the measure of the liquid state of the target colorants of this invention and are merely required within the inventive compositions upon production thereof.
  • inventive compositions may comprise any type of fabric softening formulations and compounds.
  • suitable fabric softener compositions of the present invention except the colorant are disclosed in U.S. Patents 5,183,580 to Lew et al., 5,207,933 to Trinh et al., 5,204,010 to Klewsaat, 5,290,475 to Wixon, 5,130,035 to DeH'Armo et al., and 5,089,148 to Van Blarcom et al.
  • the liquid fabric softener composition of the present invention would include from about 3 to about 50% by weight of the total composition, preferably from 15 to about 35 % by weight of a cationic fabric-softening compound, preferably a quaternary ammonium compound.
  • the counter ion may be a halide, such as fluoride, chloride, bromide, or iodide.
  • Other counter ions may be employed such as ethylsulfate, ethylsulfate, hydroxide, acetate, formate, sulfate, carbonate, and the like.
  • the counter ion is chloride or methylsulfate, chloride being especially preferred for liquid fabric conditioning compositions of the present invention.
  • concentrated liquid fabric softener compositions of the present invention can contain 17% to 50%> solids (diluted with major amounts of water, either deionized or tap in nature).
  • Particulate fabric softening compositions of the present invention can be prepared according to the formulation set out in U.S. Patent 5,332,513 to Doms et al.
  • cationic quaternary ammonium salts include, but are not limited to:
  • Acyclic quaternary ammonium salts having at least two C 8 - 30 , preferably C 12 - 22 alkyl chains such as: ditallowdimethyl ammonium chloride (Adogen® from Sherex), di(hydrogenated tallow) dimethyl ammonium chloride (Adogen 442® from Sherex), distearyl-dimethyl ammonium chloride (Arosurf TA-1000® from Sherex), dicocodimethyl ammonium chloride (Variquat K300® from Sherex), methyl bis(tallowamido ethyl)-2- hydroxyethyl ammonium methyl sulfate (Accosoft® 501 from Stepan Chemical), and the like;
  • Cyclic quaternary ammonium salts of the imidazolinium type such as di(hydrogenated tallow)-dimethyl imidazolinium chloride, l-ethylene-bis(2-tallow-l -methyl) imidazolinium chloride (Varisoft 6112® from Sherex), methyl (1) tallow amidoethyl (2) tallow imidazolinium methyl sulfate (Accosoft® 808 from Stepan Company),and the like; (3) Diamido quaternary ammonium salts such as: methyl-bis(hydrogenated tallow amidoethyl)-2-hydroxyethyl ammonium methylsulfate (Varisoft 110® from Sherex), methyl- bis(tallowamidoethyl)-2-hydroxypropyl ammonium methylsulfate (Varisoft 238® from
  • Biodegradable quaternary ammonium salts such as N,N-di(tallowoyl-oxy- ethyl)-N,N-dimethyl ammonium chloride and N,N-di(tallowoyl-oxy ⁇ propyl)-N,N-dimethyl ammonium chloride.
  • the pH of the composition is adjusted to between about 2 and 7, preferably from 3 to about 5.
  • Biodegradable ammonium salts are described more fully in U.S. Patents 4,767,547 and 4,789,491.
  • Biodegradable cationic diester compounds may be employed of the type which have the formula:
  • each R is a short chain C 1-6 , preferably C 1-3 , alkyl or hydroxyalkyl group, e.g., methyl (most preferred), ethyl, propyl, hydroxyethyl, and the like, benzyl, or mixtures thereof; each R 2 is a long chain C 10-22 hydrocarbyl, or substituted hydrocarbyl substituent, preferably C ⁇ -ig alkyl and/or alkylene, most preferably C 15-17 straight chain alkyl and/or alkylene; and the counter ion, X " , can be any softener-compatible anion, for example, chloride, bromide, methylsulfate, formate, sulfate, nitrate, and the like.
  • the fabric softening compositions of the present invention comprise a water carrier, up to 5% by weight of the total composition organic solvents, such as lower alcohols, which can improve handling, fluidity, and viscosity. From 3 to about 50% by weight of the total composition comprise the active softening compounds discussed above.
  • the fabric softeners are acyclic quaternary ammonium salts with ditallowdimethyl ammonium chloride being the most preferred.
  • non-cationic fabric conditioning agents such as tertiary fatty amines, reaction products of stearic acid and aminoethylethanolamine, carboxylic acids having from 8 to 30 carbon atoms and one carboxylic acid group per molecule, esters of polyhydric alcohols such as sorbitan esters or glyceryl stearate, fatty alcohols, ethoxylated fatty alcohols, alkylphenols, ethoxylated alkylphenols, ethoxylated fatty amines, ethoxylated monoglycerides, ethoxylated diglycerides, ethoxylated fatty amines, mineral oils, and polyols, such as polyethylene glycol.
  • non-cationic fabric conditioning agents such as tertiary fatty amines, reaction products of stearic acid and aminoethylethanolamine, carboxylic acids having from 8 to 30 carbon atoms and one carboxylic acid group per molecule, esters of polyhydric
  • pH adjusters should be added to adjust the pH of the inventive fabric softening composition to below about 7.0, preferably in the range of 4 to about 6.5.
  • any acidic material may be utilized to perform this function, such as hydrochloric acid, citric acid, maleic acid, and the like.
  • the inventive colorant is added in an amount from about 0.001 to about 3.0% by weight of the total composition; preferably from about 0.003 to about 1.0%; more preferably from about 0.01 to about 0.1%; and most preferably from about 0.015 to about 0.05%.
  • Other additives may be present in amounts from about 0.1 to about 30%> by weight of the total composition in order to provide increased softening performance, composition stability, viscosity modifications, dispersibility, and soil release.
  • These additives include silicones, predominantly polydimethylsiloxanes; soil release polymers such as block copolymers of polyethylene oxide and terephthalate fatty amines; amphoteric surfactants; smectite clays; anionic soaps; zwitterionic surfactants; and nonionic surfactants. Such surfactants and soaps mirror those discussed above in the cleaning compositions. Additionally, polymer additives may be present, such as guar gum, polyethylene oxide, and cyclodextrin. Electrolytes may also be added for viscosity control in amounts up to about 5% by weight of the total composition. Such electrolytes include calcium chloride, magnesium chloride, sodium chloride, and other Group IA and IIA halides, as well as alkylene polyammonium salts.
  • Preservatives such as glutaraldehyde and formaldehyde may also be added, as well as emulsifiers, opacifiers, anti-shrink agents, anti-wrinkle agents, fabric crisping agents, spotting agents, antioxidants, anti-corrosion agents, optical brighteners, buffers, perfumes, germicides, bactericides, and bacteriostatic agents.
  • Liquid fabric softening compositions encompassed within this invention can be prepared through standard techniques. For example, a softening active premix is prepared at
  • the colorant can then be added at any time after the preparation of this mixture while temperature-sensitive compounds must be added at certain times during the cooling down period.
  • the colorant is added to the hot water prior to addition to the premix.
  • red colorants of this invention unexpectedly provide effective non-staining even when present as very deep and dark red colorations therein the target formulations.
  • the red colorants may be mixed with other types of colorants, including acid dyes, other polymeric colorants, pigments, and the like, to produce different colorations or shades within target softener formulations.
  • Such desired color space for the target red colorants of this invention provide, at wavelengths commensurate with the visible red range, from as low as about 495 nm (for reddish-orange colorations) to about 550 nm (for reddish-purple colorations)(generally, specific red colorations are difficult to delineate with perfect consistency, and, as the ordinarily skilled artisan would understand, such a broad range above (e.g., 495-500 nm) covers most, if not all, reddish colors, while red itself falls between about 510 and 520 nm), characteristics mathematically defined by measuring the individual components of the equation:
  • E* represents the total color measurement of either the liquid formulation comprising cationic compound and red colorant, or the red colorant itself.
  • L*, a*, and b* are the color coordinates; wherein L* is a measure of the lightness and darkness of the formulation or colorant (with 0 being blackest and 100 being whitest); a* is a measure of the redness or greenness of the formulation or colorant; and b* is a measure of the yellowness or blueness of the formulation or colorant.
  • a further measurement measures the hue of the sample in terms of the angle ranging from 0 to 360 degrees, wherein the first 90 degrees represents colors of red, yellow, and orange; the next 90 degrees are yellow, yellow-green, and green; from 180 to 270 degrees, green, cyan, and blue; and above 270, blue, purple, magenta, purple, violet, and a return to red colors.
  • Another measurement, C* is utilized to define the chroma (saturation) of a sample, with brightness shown through a distance further from the base axis (e.g., a higher C* measurement indicates a brighter color).
  • such differently colored formulations should still comprise at least one of the above-defined hemicyanine red colorants to provide very effective' and dark and deep shades of these other colors in mixture with other standard colorants. Furthermore, the non-staining propensity of such polymeric hemicyanines reduces the chances of staining on target fabrics treated with such differently colored fabric softener formulations as well.
  • the preferred red colorant should exhibit CIELAB values under D65 illumination of an L* value of at least 30, an a* value of at least 20, ab* value of between -20 and 20, a C* value of at least 20, and an h° of between 300° and 30° (the higher the L* value, the brighter the color; the higher the a* value, the redder the color; the lower the b* value, the less blue the color; the higher the C*, the brighter the color), when measured by color spectrophotometer in reflectance mode using a D65 incandescent light source, and at a 10 degree observation perspective.
  • the closest art teaches red colorants that do not exhibit such required levels of color space, or which can exhibit such high levels but only when present in amounts within the target fabric softener formulation that cause staining levels on target fabrics that are highly unacceptable.
  • the specifically dark and deep red colorations provided by the hemicyanines of this invention are unexpected and beneficial, and attain color space levels heretofore unavailable while also exhibiting very low tendencies to stain.
  • the attainment of such a specific colorant would provide excellent bright and deep colors and effective mixtures with other colorants for the purposes of providing different hues and shades within the target fabric softener (or other low pH, cationic compound- containing) formulation.
  • an aniline including an aldehyde reactive group and poly(oxyalkylene) groups bonded through a linking group, here a nitrogen atom, is provided (such as disclosed within U.S. Pat. No. 4,877,411, Example 18, for example).
  • the resultant aldehyde aniline compound is then reacted with Fisher's Base (as it is commonly referred to)(a.k.a., 2- methylene-l,3,3-trimethylindoline), to effectuate the needed condensation reaction generating the desired colorant and water.
  • the linking group for the poly(oxyalkylene) group may be O or SO 2 , or other like species.
  • the preferred colorant of this invention is produced through the following method:
  • the reaction mixture was then cooled to 50°C for 2 more hours, after which the absorptivity was measured to check for complete reaction of the two components.
  • the resultant mixture was then neutralized to pH 4-5 with muriatic acid and provided a deep red liquid colorant.
  • inventive and comparative formulations were then tested on various fabric types through a test designed to mimic a worst-case scenario of a consumer leaivng the fabric softener formulation in contact with a wet garment for a long period of time.
  • the test was basically as follows:
  • Two multifiber strips (each approximately 6 inches wide and four inches long, with each individual fiber strip approximately three-quarters of an inch in width; the individual fibers were spun acetate, bleached cotton, spun nylon, spun Dacron® polyester Type 54, spun Dralon® acrylic, and worsted wool, all white in color originally) and one strip (of similar width and length to the multistrip above) of terry cotton were soaked (immersed) for 15 minutes within the test formulation.
  • the fabric strips were then each individually passed through a nip roller (36 psi) to give uniform wet pick-up of the colored product, and then dried on a drying rack at room temperature overnight.
  • the strips were then rinsed to remove any excess colored formulation therefrom and then soaked in 400 mL water (at room temperature) for 6 to 8 hours (with the water changed several times once the water became too cloudy to see the bottom of the vessel).
  • the strips were then again air-dried and visually rated using the AATCC Gray Scale For Evaluating Staining by giving two sets of treated strips to two different people for individual evaluations, along with a control strip of uncolored product.
  • the evaluators then compared the control with the treated strips and assigned individual numerical values for staining levels, with 1 being the highest degree of staining and 5 being the absolute lowest (substantially non-stained).
  • a 4 rating indicates nearly non-stained, while 3 or lower indicates clear staining is evident, with a 2 evincing a greater degree of staining thereon.
  • the results were as follows:
  • the formulations comprising the inventive red colorants alone and thus exhibiting excellent high red visible color space characteristics also exhibit greater versatility in terms of low staining propensities over a wide array of different fabrics, most notably terry cottons, than the comparatives red colorants.
  • the mixtures comprising such hemicyanine derivative colorants also exhibit excellent colorations (orange, red or pink, or purple or violet, as examples) and exhibit great versatility in terms of low-staining over a myriad of different fabrics as well, particularly as compared with similarly colored mixtures of colorants.

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Abstract

Compositions d'adoucisseurs de tissus comprenant certains colorants rouges qui permettent d'obtenir d'excellentes colorations de rouge foncé profond (à des fins esthétiques) et se mélangent très bien avec d'autres colorants pour donner de différentes teintes et tons du rouge; elles ont en même temps des niveaux faibles ou nuls de maculage des tissus colorés. Jusqu'à présent, on n'arrivait pas à obtenir ces colorations en rouge foncé avec les formulations d'adoucisseurs de tissus existants vu la tendance de ces colorants à présenter des niveaux inacceptables de maculage, notamment lorsqu'ils ont été créés dans les mêmes tons profonds et foncés que dans les formulations à faible capacité de maculage de la présente invention. Apparemment, et de manière parfaitement inattendue, les colorants présents réagissent favorablement avec des agents adoucisseurs à sel d'ammonium quaternaire, de façon à prévenir la réaction avec les fibres des tissus traités eux-mêmes, ce qui empêche leur maculage, en profondeur comme à la surface. L'invention couvre ces formulations d'adoucissants, de couleur ou de ton rouge, ainsi que n'importe quelles compositions de couleur ou de ton rouge contenant un sel d'ammonium quaternaire.
PCT/US2003/000792 2002-01-15 2003-01-10 Formulation d'adoucisseur liquide pour tissu comprenant des colorants rouges a base d'hemicyanine WO2003060047A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
AU2003217193A AU2003217193A1 (en) 2002-01-15 2003-01-10 Liquid fabric softener formulations comprising hemicyanine red colorants
JP2003560134A JP4444658B2 (ja) 2002-01-15 2003-01-10 ヘミシアニン赤色着色剤を含む液状の繊維柔軟剤配合物
DE60321126T DE60321126D1 (de) 2002-01-15 2003-01-10 Flüssige weichspüler mit hemicyaninen als rote farbmittel
EP03713229A EP1465970B1 (fr) 2002-01-15 2003-01-10 Formulation d'adoucisseur liquide pour tissu comprenant des colorants rouges a base d'hemicyanine
BRPI0306896-0A BR0306896B1 (pt) 2002-01-15 2003-01-10 Composição de amaciante de tecido líquida, compreendendo corante de derivado de hemicianina vermelho

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US10/047,061 2002-01-15
US10/047,050 2002-01-15
US10/047,061 US6638903B2 (en) 2002-01-15 2002-01-15 Non-staining red colorants and liquid fabric softener formulations comprising such non-staining colorants
US10/047,050 US6593289B1 (en) 2002-01-15 2002-01-15 Liquid fabric softener formulations comprising hemicyanine red colorants

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WO2003060047A1 true WO2003060047A1 (fr) 2003-07-24

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JP (1) JP4444658B2 (fr)
AT (1) ATE396248T1 (fr)
AU (1) AU2003217193A1 (fr)
BR (1) BR0306896B1 (fr)
DE (1) DE60321126D1 (fr)
WO (1) WO2003060047A1 (fr)

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WO2006041954A1 (fr) * 2004-10-08 2006-04-20 The Procter & Gamble Company Compositions de traitement de tissus contenant un azurant optique
JP2007529637A (ja) * 2004-02-27 2007-10-25 ザ プロクター アンド ギャンブル カンパニー 多重使用布地コンディショニング物品のための凹面組成物担体

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SG173178A1 (en) 2009-04-03 2011-09-29 Hoffmann La Roche Propane- i-sulfonic acid {3- [5- (4 -chloro-phenyl) -1h-pyrrolo [2, 3-b] pyridine-3-carbonyl] -2, 4-difluoro-pheny l } -amide compositions and uses thereof

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US4897208A (en) * 1988-10-31 1990-01-30 The Procter & Gamble Company Liquid fabric softener colored pink
US5130035A (en) * 1990-11-27 1992-07-14 Lever Brothers Company, Division Of Conopco, Inc. Liquid fabric conditioner containing fabric softener and red dye

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US4877411A (en) * 1988-08-29 1989-10-31 Milliken Research Corporation Method for color mounting the level of finish applied to textile materials and for color coding textile materials: amine-reducible fugitive tints
US4871371A (en) * 1988-10-24 1989-10-03 Milliken Research Corporation Tint compositions useful for providing coloration to aqueous and non-aqueous liquids

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US4897208A (en) * 1988-10-31 1990-01-30 The Procter & Gamble Company Liquid fabric softener colored pink
US5130035A (en) * 1990-11-27 1992-07-14 Lever Brothers Company, Division Of Conopco, Inc. Liquid fabric conditioner containing fabric softener and red dye

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007529637A (ja) * 2004-02-27 2007-10-25 ザ プロクター アンド ギャンブル カンパニー 多重使用布地コンディショニング物品のための凹面組成物担体
JP4833193B2 (ja) * 2004-02-27 2011-12-07 ザ プロクター アンド ギャンブル カンパニー 多重使用布地コンディショニング物品のための凹面組成物担体
WO2006041954A1 (fr) * 2004-10-08 2006-04-20 The Procter & Gamble Company Compositions de traitement de tissus contenant un azurant optique
US7235518B2 (en) 2004-10-08 2007-06-26 The Procter & Gamble Company Fabric care compositions comprising hueing dye

Also Published As

Publication number Publication date
DE60321126D1 (de) 2008-07-03
EP1465970B1 (fr) 2008-05-21
AU2003217193A1 (en) 2003-07-30
BR0306896A (pt) 2004-12-21
BR0306896B1 (pt) 2014-03-18
ATE396248T1 (de) 2008-06-15
EP1465970A1 (fr) 2004-10-13
JP2005515308A (ja) 2005-05-26
JP4444658B2 (ja) 2010-03-31
EP1465970A4 (fr) 2006-05-17

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