EP1240382A1 - Compositions empechant la perte de couleur par abrasion sur du tissu en denim - Google Patents

Compositions empechant la perte de couleur par abrasion sur du tissu en denim

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Publication number
EP1240382A1
EP1240382A1 EP00916664A EP00916664A EP1240382A1 EP 1240382 A1 EP1240382 A1 EP 1240382A1 EP 00916664 A EP00916664 A EP 00916664A EP 00916664 A EP00916664 A EP 00916664A EP 1240382 A1 EP1240382 A1 EP 1240382A1
Authority
EP
European Patent Office
Prior art keywords
mixtures
alkyl
hydrogen
formula
fabric
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP00916664A
Other languages
German (de)
English (en)
Inventor
Neil James Gordon
Shulin Zhang
Raphael Angeline Alfons Ceulemans
Annick Hilda Rose Coenen
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Procter and Gamble Co
Original Assignee
Procter and Gamble Co
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 Procter and Gamble Co filed Critical Procter and Gamble Co
Publication of EP1240382A1 publication Critical patent/EP1240382A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/52—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing synthetic macromolecular substances
    • D06P1/5207—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/02—After-treatment
    • D06P5/04—After-treatment with organic compounds
    • D06P5/06—After-treatment with organic compounds containing nitrogen
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/02—After-treatment
    • D06P5/04—After-treatment with organic compounds
    • D06P5/08—After-treatment with organic compounds macromolecular

Definitions

  • the present invention relates to fab ⁇ c dye protection compositions which protect denim fab ⁇ c from color loss.
  • the compositions of the present invention compnse one or more denim fab ⁇ c enhancing compounds, preferably an acrylamide co-polymer, which abates the loss of fab ⁇ c dye from denim fab ⁇ c.
  • Denim is a form of cotton fab ⁇ c which is durable, functional, comfortable, and represents a popular mode of casual dress. Unlike other fab ⁇ c, denim is dye on the "outside" of the fab ⁇ c using indigo and "indigo-hke” dyes.
  • the color loss of dye from denim fab ⁇ c also known as “fading jeans” or “fading blue jeans”, is well known, in fact, the inexorable loss of dye from denim fab ⁇ c has from time to time been accelerated by fashion designers and manufactures to provide the consumer with an article of apparel which will not under go depletion of the color du ⁇ ng usage. This "faded” look provides an article of apparel, wherem only the color loss is suggestive of extended wear, which evokes a broken-in or comfortable appearance
  • fab ⁇ c which comprises cotton denim and which is dyed in the standard manner typical of denim fabric, can be pre-treated, and subsequently re-treated, with a composition which attenuates the loss of denim color and in the case of non-indigo type dyes, can serve to abate the loss of fabric dye.
  • the present invention meets the aforementioned need in that it has been surprisingly discovered that cotton comprising fabric, especially denim fabric which is pre-treated, and subsequently re-treated with the compositions of the present invention, will resist fading and color loss due to mechanical wear and abrasion.
  • denim fabric which has not been pre-treated can have the loss of denim dye attenuated by adding the compositions of the present invention to the laundry cycle as an adjunct via pre-soak, laundry detergent additive, or rinse additive.
  • the compositions of the present invention can be added in any manner, inter alia, as part of a formulation or as a separate composition.
  • compositions providing dye protection benefits to denim fabric comprising:
  • each R 1 is independently a) hydrogen; b) C,-C 4 alkyl; c) substituted or unsubstituted phenyl; d) substituted or unsubstituted benzyl; e) carbocyclic; f) heterocyclic; g) and mixtures thereof;
  • each R 4 is independently an olefin comprising unit which is capable of propagating polymerization in addition to forming a cyclic residue with an adjacent R 4 unit;
  • R 5 is C r C 12 linear or branched alkyl, benzyl, substituted benzyl, and mixtures thereof;
  • X is a water soluble anion; and III) mixtures thereof; and B) the balance carriers and adjunct ingredients.
  • Another aspect of the present invention is the combination of a denim dye protection composition (denim dye protection component) and a fabric appearance composition (fabric enhancement component) to form a system which provides enhanced color and fabric fiber benefits to clothing and apparel comprising denim fabric, said denim dye protection system comprising:
  • the present invention also relates to methods for preventing fading an loss of color to denim fabric comprising the step of contacting denim fabric with a composition according to the present invention or with a composition which comprises the components of the present invention as a denim color-care system.
  • the present invention relates to attenuation and/or abatement of denim fabric color loss.
  • the compositions of the present invention comprise a cationic polymer or co-polymer which acts together with a low molecular weight fabric enhancement polyamine, crystal growth inhibitor, and dye fixing agent to provide protection to denim fabric from dye loss which is primarily due to mechanical loss.
  • mechanical loss of dye directly relates to the practice by garment and fabric manufacturers of surface-dying denim fabric with indigo-like or indigo-type dyes. The normal abrasive destruction of the fabric surface removes the surface layers of cotton which are dyed.
  • the combination of elements which comprise the compositions of the present invention modify the surface of cotton, especially heavy denim cotton and ameliorate many of the conditions which enhance fabric fiber surface wear and subsequent loss.
  • This change in surface condition can nullify many of the conditions which contribute to fabric damage and hence attenuate, and in some cases, abate fabric damage and therefore the concomitant loss of color.
  • compositions of the present invention can be used for a stand alone treatment of denim fabric wherem the compositions are added as ingredients to a compatible fully formulated rinsed additive, laundry additive or pre-soak all of which are used together with fabric softeners, laundry detergent compositions and the like.
  • the compositions comprise a denim fabric color integrity system.
  • the systems of the present invention are used as an initial treatment of fabric by the manufacturer of either the fabric form which apparel is made or the fully formed article of manufacture (apparel).
  • the initial pre-treatment is then reinforced at each laundry cycle by adding the second step of the system.
  • the initial treatment of the fabric can also be conveniently carried out domestically by the consumer who chooses to treat denim fabric in the home.
  • compositions of the present invention are suitable for providing a method for treating denim fabric and subsequently attenuating or abating the loss of color due to mechanical abrasion and removal of the top layer of dyed fabric.
  • compositions and systems of the present invention comprise from about 0.1%, preferably for about 1%, more preferably from about 2%, most preferably from about 3% to about 10%, preferably to about 7%, more preferably to about 5% by weight, of a polymer, copolymer, or mixture thereof, wherein said polymer or co-polymer comprises at least one cationically charged unit, mter alia, quaternary ammonium moiety or unit which can form a cationic charge in situ, inter alia, primary amine moiety.
  • the polymers or co-polymers of the present invention can comprise one or more linear polymer units having the formula:
  • the linear polymer units are formed from linearly polymerizing monomers.
  • Linearly polymerizing monomers are defined herein as monomers which under standard polymerizing conditions result in a linear polymer chain or alternatively which linearly propagate polymerization.
  • the linearly polymerizing monomers of the present invention have the formula:
  • linear monomer units are introduced indirectly, inter alia, vinyl amine units, vinyl alcohol units, and not by way of linearly polymerizing monomers.
  • vinyl acetate monomers once incorporated into the backbone are hydrolyzed to form vinyl alcohol units.
  • linear polymer units may be directly introduced, i.e. via linearly polymerizing units, or indirectly, i.e. via a precursor as in the case of vinyl alcohol cited herein above.
  • Each R 1 is independently hydrogen, C,-C 4 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted benzyl, carbocyclic, heterocyclic, and mixtures thereof.
  • R 1 is hydrogen, C C 4 alkyl, phenyl, and mixtures thereof, more preferably hydrogen and methyl.
  • Each R 2 is independently hydrogen, halogen, C,-C 4 alkyl, C,-C 4 alkoxy, substituted or unsubstituted phenyl, substituted or unsubstituted benzyl, carbocyclic, heterocyclic, and mixtures thereof.
  • Preferred R 2 is hydrogen, C,-C 4 alkyl, and mixtures thereof.
  • Each Z is independently hydrogen; hydroxyl; halogen; -(CH 2 ) m R, wherein R is hydrogen, hydroxyl, halogen, nitrilo, -OR 3 , -0(CH 2 ) n N(R 3 ) 2 , -0(CH 2 ) n N + (R 3 ) 3 X " , -OCO(CH 2 ) n N(R 3 ) 2 , - OCO(CH 2 ) n N + (R 3 ) 3 X-, -NHCO(CH 2 ) n N(R 3 ) 2 , -NHCO(CH 2 ) n N + (R 3 ) 3 X ⁇ -(CH 2 ) n N(R 3 ) 2 , -
  • a preferred Z is -0(CH 2 ) n N (R 3 ) 3 X " , wherein the index n is 2 to 4.
  • the index m is from 0 to 6, preferably 0 to 2, more preferably 0.
  • Non-limiting examples of linearly polymerizing monomers comprising a heterocyclic Z unit includes l-vinyl-2-pyrrolidinone, 1 -vinylimidazole, 2-vinyl-l,3-dioxolane, 4-vinyl-l- cyclohexenel,2-epoxide, and 2-vinylpyridine.
  • the polymers and co-polymers of the present invention comprise Z units which have a cationic charge or which result in a unit which forms a cationic charge in situ.
  • Z units which have a cationic charge or which result in a unit which forms a cationic charge in situ.
  • the co- polymers of the present invention comprise more than one Z unit, for example, Z 1 , Z 2 ,...Z n units, at least about 1% of the monomers which comprise the co-polymers will comprise a cationic unit.
  • Preferred cationic units include -0(CH 2 ) n N + (R 3 ) 3 X " and -(CH 2 ) ⁇ N + (R 3 ) 3 X " .
  • the ratio of Z 1 to Z 2 is preferably from about 9: 1 to about 1 :9.
  • a non-limiting example of an indirect Z unit which can be made to form a cationic charge in situ is the -NHCHO unit, formamide.
  • the formulator can prepare a polymer or copolymer comprising formamide units some of which are subsequently hydrolyzed to form vinyl amine equivalents.
  • the formulator may prepare a co-polymer having the general formula:
  • Another class of preferred linearly polymerizable monomers comprise cationically charged heteroaromatic Z units having the formula:
  • Another class of preferred linearly polymerizable monomers which comprises a heterocyclic ring includes Z units comprising an N-oxide, for example, the N-oxide having the formula:
  • N-alkyl vinylpyridine monomers and N-oxide vinylpyridine monomers can be suitably combined with other non aromatic monomers, inter alia, vinyl amine.
  • preferred polymers of the present invention include co-polymers derived from a combination of quatemized, N-oxide, and nitrogen containing heteroaromatic monomers, non-limiting examples of which includes a copolymer of N-methyl vinyl pyridine and vinyl pyridine in a ratio of 4:1; a copolymer of N-methyl vinyl pyridine and vinyl pyridine in a ratio of 4:6; a co-polymer of poly(N-methyl vinyl pyridine) and vinyl pyridine N-oxide in a ratio of polymer to monomer of 4:1; poly(N-methyl vinyl pyridine) and vinyl pyridine N-oxide in a ratio of polymer to monomer of 4:6; and mixtures thereof.
  • a preferred linear co-polymer according to the present has the formula:
  • Z 1 has the formula:
  • X is chlorine; x has the value of from about 10 to about 100,000; y has the value of from about 10 to about 100,000; the ratio of x to y is from 9:1 to 1:9.
  • Co-polymers of this type are available as, e.g., Sedipur ® CF104 ex BASF.
  • polymer residues may be formed by treatment of the resulting polymer.
  • vinyl amine residues are preferably introduced via formamide monomers which are subsequently hydrolyzed to the free amino unit.
  • vinyl alcohol units are obtained by hydrolysis of residues formed form vinyl acetate monomers.
  • acrylic acid residues may be esterified after polymerization, for example, units having the formula:
  • Cyclic Units Derived from Cyclically Polymerizing Monomers can comprise one or more cyclic polymer units which are derived from cyclically polymerizing monomers.
  • Cyclically polymerizing monomers are defined herein as monomers which under standard polymerizing conditions result in a cyclic polymer residue as well as serving to linearly propagate polymerization.
  • Preferred cyclically polymerizing monomers of the present invention have the formula:
  • each R 4 is independently an olefin comprising unit which is capable of propagating polymerization in addition to forming a cyclic residue with an adjacent R 4 unit;
  • R 5 is C ⁇ -C 12 linear or branched alkyl, benzyl, substituted benzyl, and mixtures thereof;
  • X is a water soluble anion.
  • R 4 units include allyl and alkyl substituted allyl units.
  • the resulting cyclic residue is a six-member ring comprising a quaternary nitrogen atom.
  • R 5 is preferably C,-C 4 alkyl, preferably methyl.
  • cyclically polymerizing monomer which results in a cyclic polymer unit is dimethyl diallyl ammonium having the formula:
  • index z is from about 10 to about 50,000. Ill) Mixtures thereof.
  • the polymers or co-polymers of the present invention must retain a net cationic charge, whether the charged is developed in situ, or whether the polymer or co-polymer itself has a formal positive charge.
  • the polymer or co-polymer has at least 10%, more preferably at least about 25%, more preferably at least about 35%, most preferably at least about 50% of the residues comprise a cationic charge.
  • the polymers or co-polymers of the present invention can comprise mixtures of linearly and cyclically polymerizing monomers, for example the poly(dimethyldiallyl-ammonium chloride/acrylamide) co-polymer having the formula: wherein Z 1 , Z 2 , x, y, and z are the same as defined herein above and X is chloride ion.
  • a particularly preferred embodiment of this invention is the composition comprising a polymer based on dimethyldiallylammonium chloride and a copolymer which is based upon acrylamide with a co-monomer selected from the group consisting of N, N dialkylaminoalkyl(meth)acrylate, N, N dialkylaminoalkylacrylate, N,N dialkylaminoalkylacrylamide, N,N dialkylaminoalkyl(meth)acrylamide, their quatemized derivatives and mixtures thereof.
  • Non-limiting examples of preferred polymers according to the present invention include dye maintenance copolymers comprising: i) a first monomer selected from the group consisting of N, N dialkylaminoalkyl(meth)acrylate, N, N dialkylaminoalkylacrylate, N,N dialkylaminoalkylacrylamide, N,N dialkylaminoalkyl(meth)acrylamide, their quatemized derivatives and mixtures thereof; and ii) a second monomer selected from the group consisting of acrylic acid, methacrylic acid, C r C 6 alkylmethacrylate, C r C 6 alkyl acrylate, C,-C 8 hydroxyalkylacrylate, C,-C 8 hydroxyalkylmethacrylate, acrylamide, C ⁇ -C, 6 alkyl acrylamide, C r C 16 dialkylacrylamide, 2-acrylamido-2-methylpropane sulfonic acid or its alkali salt, methacrylamide, C C, 6
  • the present invention also relates to systems for providing enhanced care to denim fabric.
  • the denim care systems according to the present invention comprise a composition providing dye protection benefits to denim fabric in combination with a separately added composition which provides a fabric enhancement benefit, said system comprising: A) from about 1%, preferably from about 5%, more preferably from about 10% to about 50%), preferably to about 30%, more preferably to about 20% by weight, of a polymer or co-polymer comprising denim dye protection composition as described herein; and
  • a fabric enhancement composition comprising: a) from about 0.01%, preferably from about 0.1% to about 20%, preferably to about 10% by weight, of a fabric abrasion reducing polymer, said fabric abrasion polymer comprising: i) at least one monomeric unit comprising an amide moiety; ii) at least one monomeric unit comprising an N-oxide moiety; iii) and mixtures thereof; b) optionally from about 1%, preferably from about 10%, more preferably from about 20% to about 80%, preferably to about 60%), more preferably to about 45% by weight, of a fabric softening active; c) optionally less than about 15% by weight, of a principal solvent, preferably said principal solvent has a ClogP of from about 0.15 to about i; d) optionally from about 0.001% to about 90% by weight, of one or more dye fixing agents; e) optionally from about 0.01% to about 50% by weight, of one or more cellulose
  • a non-limiting example of a preferred system according to the present invention comprises:
  • a fabric enhancement composition comprising: a) from about 0.01% to about 50% by weight, of a polyamine, said polyamine is selected from the group consisting of N,N'- bis(aminopropyl)-l,3-propylenediamine; N,N'-bis(hydroxyethyl)-N,N'- bis[3-N,N-bis(hydroxyethyl)aminopropyl]-l,3-propylenediamine; N,N'- bis(2-hydroxypropyl)-N,N'-bis[3-N,N-bis(2- hydroxypropyl)aminopropyl]-l,3-propylenediamine; N,N'-bis(2- hydroxybutyl)-N,N'-bis[3-N,N-bis(2-hydroxybutyl)aminopropyl]-l,3- propylenediamine; 5-N-methyl dipropylenetriamine; l
  • the compositions comprise from about 50%>, preferably from about 80% to about 99.9%, preferably to about 99%>, more preferably to about 98% by weight, of a fabric enhancement component.
  • compositions of the present invention comprise from about 0.01%, preferably from about 0.75%), more preferably from 2%, to about 50%>, preferably to about 35%>, more preferably to about 20%, most preferably to about 15% by weight, of the herein described low molecular weight polyamines.
  • the polyamines are either linear polyamines or cyclic polyamines.
  • the enhanced fabric appearance compositions of the present invention may comprise one or more polyalkyleneimines which have backbones comprising C 2 -C 6 alkylene units, however, the backbones must comprise at least one C 3 - alkylene unit, preferably the linear polyamines have each backbone unit comprising a C 3 -C 6 alkylene unit.
  • polyamines of the present invention have the formula:
  • each R is independently C 2 -C 6 linear alkylene, C 3 -C 6 branched alkylene, and mixtures thereof; preferably the backbone is a mixture of ethylene, 1,3-propylene, 1,3-propylene, 1,4- butylene, 1 ,6-hexylene, more preferably a mixture of ethylene and 1,3-propylene, most preferably the backbone comprises only 1,3-propylene units.
  • R 1 is hydrogen; C,-C ⁇ 2 alkyl, preferably C,-C 8 alkyl, more preferably C r C 4 alkyl; alkyleneoxy having the formula:
  • R 3 is C 2 -C 6 linear alkylene, C 3 -C 6 branched alkylene, or mixtures thereof; preferably ethylene, mixtures of ethylene and 1 ,2-propylene, 1 ,2-butylene, preferably ethylene, 1,2- propylene.
  • R is hydrogen, C,-C 6 alkyl, or mixtures thereof; preferably hydrogen or methyl, more preferably hydrogen.
  • the index m is from 1 to 4, however, the value of m is predicated on the desired fabric enhancement benefit sought by the formulator. For example, the level of bleach protection varies over the value of m.
  • the dye fixation properties of the substantially linear polyamines are maximized when the alkyleneoxy unit is absent, i.e., R 1 and R 2 are hydrogen.
  • R 1 is also acyl having the formula:
  • R 5 is C,-C 22 linear or branched alkyl, C 3 -C 22 linear or branched alkenyl, or mixtures thereof; preferably R 5 is a hydrocarbyl moiety which sufficiently provides increased fabric lubricity, more preferably C 6 -C 12 alkyl; hydroxy alkyl having the formula: (CH 2 ) y (CHOH) z H wherein the index y is from 1 to 5, z is from 1 to 3, provided y + z is less than or equal to 6 and the -(CHOH)- unit is not directly attached to a nitrogen atom.
  • Non-limiting examples of hydroxy alkyl units include 2-hydroxy alkyl, for example, -CH 2 CHOHCH 3 , -CH 2 CHOHCH 2 CH 2 CH 2 CH 3 .
  • Two R 1 units can be taken together to form a 5-7 member ring, i.e., piperidine, morpholine.
  • An example of a backbone wherein two R 1 units are taken together to form a ring has the formula:
  • the present invention also includes mixtures of the herein described R 1 units.
  • R 2 is hydrogen, R 1 , -RN(R') 2 , and mixtures thereof.
  • the integer n has the value from 1 or 6; preferably from 1 to 4, more preferably 1 or 3.
  • linear polyamine has a backbone wherein R is 1,3-propylene and n is equal to 2, N,N'-bis(3-aminopropyl)-l,3-propylenediamine (TPTA).
  • TPTA N,N'-bis(3-aminopropyl)-l,3-propylenediamine
  • This preferred backbone can then be substituted or left unsubstituted in a manner which affords the formulator the maximal fabric benefit and compatibility of the low molecular weight amine with the particular embodiment.
  • R 1 and R 2 are each equal to hydrogen, dye fixative properties, in certain liquid fabric care embodiments, even in the presence of bleach, are maximal. Also when R 1 and R 2 are not equal to hydrogen, bleach scavenging benefits are enhanced.
  • the preferred backbones of the linear polyamines of the present invention comprise at least one 1,3-propylene unit, preferably at least two 1,3-propylene units.
  • a backbone nitrogen when referred to as "unmodified” the nitrogen contains only hydrogen atoms.
  • “Modified” polyamines have one or more alkyleneoxy units as described herein above. Preferred substituents are methyl, 2- hydroxyethyl, 2-hydroxypropyl, 1,2-propyleneoxy, 2-hydroxybutyl, and mixtures thereof, more preferably methyl and 2-hydroxypropyl.
  • polyamines which comprise alkylated polyamines are preferred, for example, tetramethyl dipropylenetriamine (5 -N-methyl dipropylenetriamine) having the formula:
  • the enhanced fabric appearance compositions of the present invention may comprise one or more cyclic polyalkyleneamines wherein at least one of the ring nitrogens is substituted with at least one C 3 -C 6 alkyleneimine unit.
  • the low molecular weight cyclic polyamines of the present invention comprise polyamine backbones having the formula:
  • R is hydrogen, -(CH 2 ) k N(R 1 ) 2 , and mixtures thereof, wherein at least one cyclic polyamine R unit is a -(CH 2 ) k N(R') 2 unit; preferably both R units are -(CH 2 ) k N(R') 2 ; wherein each index k independently has the value from 3 to 12, preferably k is 3.
  • the backbone of the cyclic amines including R units is 250 daltons or less. Most preferred backbone ring is 1,4-piperazine.
  • R 1 is hydrogen; C C 12 alkyl, preferably C,-C 8 alkyl, more preferably C,-C 4 alkyl, most preferably methyl; alkyleneoxy having the formula: -(R 3 0) m -R 4 wherein R 3 is C 2 -C 6 linear alkylene, C 3 -C 6 branched alkylene, or mixtures thereof; preferably ethylene, mixtures of ethylene and 1 ,2-propylene, 1 ,2-butylene, preferably ethylene, 1,2- propylene.
  • R 4 ⁇ s hydrogen, C,-C 6 alkyl, or mixtures thereof, preferably hydrogen or methyl, more preferably hydrogen.
  • the index m is from 1 to 4, however, the value of m is predicated on the desired fab ⁇ c enhancement benefit sought by the formulator. For example, the level of bleach protection varies over the value of m.
  • R 1 is also acyl having the formula:
  • R 5 is C r C 22 linear or branched alkyl, C 3 -C 22 linear or branched alkenyl, or mixtures thereof; preferably R 5 is a hydrocarbyl moiety which sufficiently provides increased fab ⁇ c lubncity, more preferably -C 12 alkyl; hydroxy alkyl having the formula:
  • hydroxy alkyl units include 2-hydroxy alkyl, for example, -CH 2 CHOHCH 3 , -CH 2 CHOHCH 2 CH 2 CH 2 CH 3 .
  • Two R 1 units can be taken together to form a 5-7 member ⁇ ng, i.e., pipe ⁇ dine, morphohne.
  • the backbone of the cyclic amines of the present invention comprise a N,N'- bis-substituted 1,4-piperazine ⁇ ng having the formula:
  • Examples of carbonyl containing rings which comprise L units are 1,4-d ⁇ ketop ⁇ pe ⁇ z ⁇ nes.
  • the backbones of the polyamines of the present invention prior to modification, have the formula: H 2 N-(CH 2 ) 3 — N N— (CH 2 ) 3 -NH 2
  • each R unit is -(CH 2 ) 3 NH 2 .
  • the cyclic units may be substituted on only one ring nitrogen as in the case wherein one R unit is hydrogen, and the other R unit is -(CH 2 ) k NH 2 , for example, the piperazine having the formula:
  • the backbones of the cyclic polyamines of the present invention preferably comprise at least one 1,3-propylene unit, more preferably at least two 1,3-propylene units.
  • a backbone nitrogen when referred to as "unmodified” the nitrogen contains only hydrogen atoms.
  • “Modified” polyamines have one or more substituent units as described herein above. Preferably when the backbone units are modified all of the nitrogens are modified.
  • Preferred alkyleneoxy substituents are ethyleneoxy, 1 ,2-propyleneoxy, and mixtures thereof, more preferably 1 ,2-propyleneoxy.
  • compositions of the present invention optionally comprise from about 0.005%), preferably from about 0.5%, more preferably from about 0.1% to about 1%, preferably to about 0.5%, more preferably to about 0.25%, most preferably to about 0.2% by weight, of one or more crystal growth inhibitors.
  • crystal Growth Inhibition Test is used to determine the suitability of a material for use as a crystal growth inhibitor.
  • the suitability of a material to serve as a crystal growth inhibitor according to the present invention can be determined by evaluating in vitro the growth rate of certain inorganic micro- crystals.
  • the procedure of Nancollas et al., described in "Calcium Phosphate Nucleation and Growth in Solution", Prog. Crystal Growth Charact., Vol 3, 77-102, (1980), incorporated herein by reference, is a method which is suitable for evaluating compounds for their crystal growth inhibition.
  • the graph below serves as an example of a plot indicating the time delay (t-lag) in crystal formation afforded by a hypothetical crystal growth inhibitor.
  • the hydroxyapatite slurry can be prepared by digesting Bio-Gel ® HTP hydroxyapatite powder (100 g) in 1 L of distilled water the pH of which is adjusted to 2.5 by the addition of sufficient 6N HCI and subsequently heating the solution until all of the hydroxyapatite is dissolved (heating for several days may be necessary). The temperature of the solution is then maintained at about 22° C while the pH is adjusted to 12 by the addition of a solution of 50%) aqueous KOH. Once again the solution is heated and the resulting slurry is allowed to settle for two days before the supernatant is removed. 1.5 L of distilled water is added, the solution stirred, then after settling again for 2 days the supernatant is removed. This rinsing procedure is repeated six more time after which the pH of the solution is adjusted to neutrality using 2N HCI. The resulting slurry can be stored at 37°C for eleven months.
  • Crystal growth inhibitors which are suitable for use in the present invention have a t-lag of at least 10 minutes, preferably at least 20 minutes, more preferably at least 50 minutes, at a concentration of 1 x 10 "6 M.
  • Crystal growth inhibitors are differentiated form chelating agents by the fact that crystal growth inhibitors have a low binding affinity of heavy metal ions, i.e., copper.
  • crystal growth inhibitors have an affinity for copper ions in a solution of 0.1 ionic strength when measured at 25° C, of less than 15, preferably less than 12.
  • the preferred crystal growth inhibitors of the present invention are selected from the group consisting of carboxylic compounds, organic diphosphonic acids, and mixtures thereof.
  • the following are non-limiting examples of preferred crystal growth inhibitors.
  • Non-limiting examples of carboxylic compounds which serve as crystal growth inhibitors include glycolic acid, phytic acid, polycarboxylic acids, polymers and co-polymers of carboxylic acids and polycarboxylic acids, and mixtures thereof.
  • the inhibitors may be in the acid or salt form.
  • the polycarboxylic acids comprise materials having at least two carboxylic acid radicals which are separated by not more than two carbon atoms (e.g., methylene units).
  • the preferred salt forms include alkali metals; lithium, sodium, and potassium; and alkanolammonium.
  • the polycarboxylates suitable for use in the present invention are further disclosed in U.S. 3,128,287, U.S. 3,635,830, U.S.
  • polycarboxylates include ether hydroxypolycarboxylates, polyacrylate polymers, copolymers of maleic anhydride and the ethylene ether or vinyl methyl ethers of acrylic acid. Copolymers of 1,3,5-trihydroxybenzene, 2, 4, 6-trisulphonic acid, and carboxymethyloxysuccinic acid are also useful.
  • Alkali metal salts of polyacetic acids for example, ethylenediamine tetraacetic acid and nitrilotriacetic acid
  • the alkali metal salts of polycarboxylates for example, mellitic acid, succinic acid, oxydisuccinic acid, polymaleic acid, benzene 1,3,5-tricarboxylic acid, carboxymethyloxysuccinic acid, are suitable for use in the present invention as crystal growth inhibitors.
  • the polymers and copolymers which are useful as crystal growth inhibitors have a molecular weight which is preferably greater than about 500 daltons to about 100,000 daltons, more preferably to about 50,000 daltons.
  • Examples of commercially available materials for use as crystal growth inhibitors include, polyacrylate polymers Good-Rite® ex BF Goodrich, Acrysol® ex Rohm & Haas, Sokalan® ex BASF, and Norasol® ex Norso Haas.
  • Polycarboxylate crystal growth inhibitors include citrates, e.g., citric acid and soluble salts thereof (particularly sodium salt), 3,3-dicarboxy-4-oxa-l,6-hexanedioates and related compounds further disclosed in U.S. 4,566,984 incorporated herein by reference, C5-C20 alkyl, C5-C20 alkenyl succinic acid and salts thereof, of which dodecenyl succinate, lauryl succinate, myristyl succinate, palmityl succinate, 2-dodecenylsuccinate, 2-pentadecenyl succinate, are non- limiting examples.
  • Other suitable polycarboxylates are disclosed in U.S. 4,144,226, U.S. 3,308,067 and U.S. 3,723,322, all of which are incorporated herein by reference.
  • Organic diphosphonic Acids are also suitable for use as crystal growth inhibitors.
  • organic diphosphonic acid is defined as "an organo- diphosphonic acid or salt which does not comprise a nitrogen atom”.
  • Preferred organic diphosphonic acids include C C 4 diphosphonic acid, preferably C 2 diphosphonic acid selected from the group consisting of ethylene diphosphonic acid, ⁇ -hydroxy-2 phenyl ethyl diphosphonic acid, methylene diphosphonic acid, vinylidene- 1,1 -diphosphonic acid , l,2-dihydroxyethane-l,l- diphosphonic acid, hydroxy-ethane 1 , 1 diphosphonic acid, the salts thereof, and mixtures thereof. More preferred is hydroxyethane- 1,1 -diphosphonic acid (HEDP). Dve Fixing Agents
  • compositions of the present invention optionally comprise from about 0.001%, preferably from about 0.5% to about 90%, preferably to about 50%, more preferably to about 10%, most preferably to about 5% by weight, of one or more dye fixing agents.
  • Dye fixing agents are well-known, commercially available materials which are designed to improve the appearance of dyed fabrics by minimizing the loss of dye from fabrics due to washing. Not included within this definition are components which can in some embodiments serve as fabric softener actives.
  • Cationic fixatives are available under various trade names from several suppliers. Representative examples include: CROSCOLOR PMF (July 1981, Code No. 7894) and CROSCOLOR NOFF (January 1988, Code No. 8544) ex Crosfield; INDOSOL E-50 (February 27, 1984, Ref. No. 6008.35.84; polyethyleneamine-based) ex Sandoz; SANDOFIX TPS, ex Sandoz, is a preferred dye fixative for use herein.
  • SANDOFIX SWE a cationic resinous compound ex Sandoz
  • REWIN SRF REWIN SRF-O and REWIN DWR ex CHT-Beitlich GMBH
  • Tinofix® ECO Tinofix® FRD
  • Solfin® Ex Ciba-Geigy
  • a preferred dye fixing agent for use in the compositions of the present invention is CARTAFIX CB® ex Clariant.
  • Other cationic dye fixing agents are described in "Aftertreatments for Improving the Fastness of Dyes on Textile Fibres", Christopher C. Cook, Rev. Prog. Coloration, Vol. XII, (1982).
  • Dye fixing agents suitable for use in the present invention are ammonium compounds such as fatty acid-diamine condensates inter alia the hydrochloride, acetate, metosulphate and benzyl hydrochloride salts of diamine esters.
  • ammonium compounds such as fatty acid-diamine condensates inter alia the hydrochloride, acetate, metosulphate and benzyl hydrochloride salts of diamine esters.
  • Non-limiting examples include oleyldiethyl aminoethylamide, oleylmethyl diethylenediamine methosulphate, monostearylethylene diaminotrimethylammonium methosulphate.
  • N-oxides of tertiary amines are suitable for use as dye fixatives in the compositions of the present invention.
  • Cellulose Reactive Dye Fixing Agents are suitable for use as dye fixatives in the compositions of the present invention.
  • compositions of the present invention optionally comprise from about 0.01%, preferably from about 0.05%, more preferably from about 0.5% to about 50%, preferably to about 25%, more preferably to about 10% by weight, most preferably to about 5% by weight, of one or more cellulose reactive dye fixing agents.
  • the cellulose reactive dye fixatives may be suitably combined with one or more dye fixatives described herein above in order to comprise a "dye fixative system”.
  • cellulose reactive dye fixing agent is defined herein as "a dye fixative agent which reacts with the cellulose fibers upon application of heat or upon a heat treatment either in situ or by the formulator".
  • the cellulose reactive dye fixing agents suitable for use in the present invention can be defined by the following test procedure.
  • All four swatches (the two control swatches and the two treated swatches, one of each which has been treated by the ironing calender) are washed separately in Launder-O-Meter pots under typical conditions with a commercial detergent used at the recommended dosage for V ⁇ hour at 60°C, followed by a thorough rinsing of 4 times 200 ml of cold water and subsequently line dried.
  • DE values the computed color difference
  • ASTM D2244 the computed color difference
  • DE values relate to the magnitude and direction of the difference between two psychophysical color stimuli defined by tristimulus values, or by chromaticity coordinates and luminance factor, as computed by means of a specified set of color-difference equations defined in the CIE 1976 CIELAB opponent-color space, the Hunter opponent-color space, the Friele-Mac Adam-Chickering color space or any equivalent color space.
  • the lower the DE value for a sample the closer the sample is to the un-tested sample and the greater the color fastness benefit.
  • the candidate is a cellulose reactive dye fixing agent for the purposes of the invention.
  • cellulose reactive dye fixing agents are compounds which contain a cellulose reactive moiety
  • non limiting examples of these compounds include halogeno-triazines, vinyl sulphones, epichlorhydrine derivatives, hydroxyethylene urea derivatives, formaldehyde condensation products, polycarboxylates, glyoxal and glutaraldehyde derivatives, and mixtures thereof. Further examples can be found in “Textile Processing and Properties", Tyrone L. Vigo, at page 120 to 121, Elsevier (1997), which discloses specific electrophilic groups and their corresponding cellulose affinity.
  • Preferred hydroxyethylene urea derivatives include dimethyloldihydroxyethylene, urea, and dimethyl urea glyoxal.
  • Preferred formaldehyde condensation products include the condensation products derived from formaldehyde and a group selected from an amino-group, an imino-group, a phenol group, an urea group, a cyanamide group and an aromatic group.
  • Commercially available compounds among this class are Sandofix WE 56 ex Clariant, Zetex E ex Zeneca and Levogen BF ex Bayer.
  • Preferred polycarboxylates derivatives include butane tetracarboxilic acid derivatives, citric acid derivatives, polyacrylates and derivatives thereof.
  • a most preferred cellulosic reactive dye fixing agents is one of the hydroxyethylene urea derivatives class commercialized under the tradename of Indosol CR ex Clariant. Still other most preferred cellulosic reactive dye fixing agents are commercialized under the tradename Rewin DWR and Rewin WBS ex CHT R. Beitlich.
  • a preferred dye fixing agent for use in the compositions of the present invention is CARTAFIX CB® ex Clariant.
  • compositions of the present invention may also optionally comprise one or more adjunct ingredients.
  • adjunct ingredients are selected from the group consisting of fabric softener actives, electrolytes, stabilizers, low molecular weight water soluble solvents, chelating agents, cationic charge boosters, dispersibility aids, soil release agents, nonionic fabric softening agents, concentration aid, perfume, preservatives, colorants, optical brighteners, opacifiers, fabric care agents, anti-shrinkage agents, anti-wrinkle agents, fabric crisping agents, spotting agents, germicides, fungicides, anti-corrosion agents, antifoam agents, and mixtures thereof.
  • Fabric Softening Actives are selected from the group consisting of fabric softener actives, electrolytes, stabilizers, low molecular weight water soluble solvents, chelating agents, cationic charge boosters, dispersibility aids, soil release agents, nonionic fabric softening agents, concentration aid, perfume, preservatives, colorants, optical brighten
  • compositions of the present invention optionally comprise at least about 1%, preferably from about 10%, more preferably from about 20% to about 80%, more preferably to about 60%, most preferably to about 45% by weight, of the composition of one or more fabric softener actives.
  • the preferred fabric softening actives according to the present invention are amines having the formula:
  • each R is independently Ci -Cg alkyl, Ci -Cg hydroxyalkyl, benzyl, and mixtures thereof;
  • R ⁇ is preferably Ci 1-C22 linear alkyl, Ci 1 -C22 branched alkyl, C ⁇ 1 -C22 linear alkenyl, C 1-C22 branched alkenyl, and mixtures thereof;
  • Q is a carbonyl moiety independently selected from the units having the formula:
  • R ⁇ is hydrogen, C1-C4 alkyl, preferably hydrogen;
  • R ⁇ is Ci -C4 alkyl, preferably hydrogen or methyl;
  • Q has the formula:
  • X is a softener compatible anion, preferably the anion of a strong acid, for example, chlo ⁇ de, bromide, methylsulfate, ethylsulfate, sulfate, nitrate and mixtures thereof, more preferably chloride and methyl sulfate.
  • the anion can also, but less preferably, carry a double charge, in which case X' " ' represents half a group.
  • the index m has a value of from 1 to 3; the index n has a value of from 1 to 4, preferably 2 or 3, more preferably 2.
  • One embodiment of the present invention provides for amines and quatemized amines having two or more different values for the index n per molecule, for example, a softener active prepared from the starting amine methyl(3-ammopropyl)(2-hydroxyethyl)am ⁇ ne.
  • More preferred softener actives according to the present invention have the formula:
  • R 1 1 is a fatty acyl moiety.
  • Suitable fatty acyl moieties for use m the softener actives of the present invention are derived from sources of triglycendes including tallow, vegetable oils and/or partially hydrogenated vegetable oils including wter aha canola oil, safflower oil, peanut oil, sunflower oil, com oil, soybean oil, tall oil, rice bran oil. Yet more preferred are the Diester Quaternary Ammonium Compounds (DEQA's) wherein the index m is equal to 2.
  • DEQA's Diester Quaternary Ammonium Compounds
  • the formulator depending upon the desired physical and performance properties of the final fabnc softener active, can choose any of the above mentioned sources of fatty acyl moieties, or alternatively, the formulator can mix sources of t ⁇ glyce ⁇ de to form a "customized blend".
  • the fatty acyl composition may vary, as in the case of vegetable oil, from crop to crop, or from va ⁇ ety of vegetable oil source to va ⁇ ety of vegetable oil source.
  • DEQA's which are prepared using fatty acids derived from natural sources are preferred.
  • a preferred embodiment of the present invention provides softener actives comprising R!
  • mixed chain fatty acyl units is defined as "a mixture of fatty acyl units comprising alkyl and alkenyl chains having from 10 carbons to 22 carbon atoms including the carbonyl carbon atom, and in the case of alkenyl chains, from one to three double bonds, preferably all double bonds in the cis configuration".
  • R! units of the present invention it is preferred that at least a substantial percentage of the fatty acyl groups are unsaturated, e.g., from about 25%, preferably from about 50% to about 70%), preferably to about 65%.
  • the total level of fabric softening active containing polyunsaturated fatty acyl groups can be from about 3%, preferably from about 5%, more preferably from about 10% to about 30%, preferably to about 25%, more preferably to about 18%.
  • cis and trans isomers can be used, preferably with a cis/ 'trans ratio is of from 1:1, preferably at least 3:1, and more preferably from about 4:1 to about 50:1, more preferably about 20: 1 , however, the minimum being 1 : 1.
  • the level of unsaturation contained within the tallow, canola, or other fatty acyl unit chain can be measured by the Iodine Value (IV) of the corresponding fatty acid, which in the present case should preferably be in the range of from 5 to 100 with two categories of compounds being distinguished, having a IV below or above 25.
  • IV Iodine Value
  • a cisltrans isomer weight ratio greater than about 30/70, preferably greater than about 50/50 and more preferably greater than about 70/30 provides optimal concentrability.
  • a further preferred embodiment of the present invention comprises DEQA's wherein the average Iodine Value for R! is approximately 45.
  • the R! units suitable for use in the isotropic liquids present invention can be further characterized in that the Iodine Value (IV) of the parent fatty acid, said IV is preferably from about 10, more preferably from about 50, most preferably from about 70, to a value of about 140, preferably to about 130, more preferably to about 115.
  • formulators may wish to add an amount of fatty acyl units which have Iodine Values outside the range listed herein above. For example, "hardened stock" (IV less than or equal to about 10) may be combined with the source of fatty acid admixture to adjust the properties of the final softener active.
  • a prefered source of fatty acyl units especially fatty acyl units having branching, for example, "Guerbet branching", methyl, ethyl, etc. units substituted along the primary alkyl chain
  • synthetic sources of fatty acyl units are also suitable.
  • the formulator may with to add one or more fatty acyl units having a methyl branch at a "non-naturally occuring" position, for example, at the third carbon of a Ci 7 chain.
  • acyl units whihc are not found in significant (greater than about 0.1%) quantities is common fats and oils which serve as feedstocks for the source of triglycerides described herein.” If the desired branched chain fatty acyl unit is unavailable from readily available natural feedstocks, therefore, synthetic fatty acid can be suitably admixed with other synthetic materials or with other natural triglyceride derived sources of acyl units.
  • N,N-di(tallowoyl-oxy-ethyl)-N,N-dimethyl ammonium chloride Particularly preferred is N,N-di(tallowoyl-oxy-ethyl)-N,N-dimethyl ammonium chloride, where the tallow chains are at least partially unsaturated and N,N-di(canoloyl-oxy-ethyl)-N,N- dimethyl ammonium chloride, N,N-di(tallowyl-oxy-ethyl)-N-methyl, N-(2-hydroxyethyl) ammonium methyl sulfate; N,N-di(canolyl-oxy-ethyl)-N-methyl, N-(2-hydroxyethyl) ammonium methyl sulfate; and mixtures thereof.
  • the present invention further relates to methods for utilizing the systems and compositions of the present invention to abate and/or attenuate the loss of denim fabric color.
  • One method according to the present invention comprises the step of contacting denim fabric which has been manufactured at a point wherein the fabric has not been worn or used, with a composition comprising:
  • each R 4 is independently an olefin comprising unit which is capable of propagating polymerization in addition to forming a cyclic residue with an adjacent R 4 unit;
  • R 5 is C,-C 12 linear or branched alkyl, benzyl, substituted benzyl, and mixtures thereof;
  • X is a water soluble anion;
  • a fabric enhancement composition comprising: a) from about 0.01%, preferably from about 0.1% to about 20%, preferably to about 10% by weight, of a fabric abrasion reducing polymer, said fabric abrasion polymer comprising: i) at least one monomeric unit comprising an amide moiety; ii) at least one monomeric unit comprising an N-oxide moiety; iii) and mixtures thereof; b) optionally from about 1%, preferably from about 10%, more preferably from about 20% to about 80%, preferably to about 60%, more preferably to about 45% by weight, of a fabric softening active; c) optionally less than about 15% by weight, of a principal solvent, preferably said principal solvent has a ClogP of from about 0.15 to about l; d) optionally from about 0.001% to about 90% by weight, of one or more dye fixing agents; e) optionally from about 0.01% to about 50% by weight, of
  • a preferred usage regime consists of the pre-treating the garment, or the fabric from which it is derived, with a composition according to the present invention.
  • This pre-treatment can be carried out by the manufacturer of the garment, or by the consumer.
  • the pre-treatment can conveniently be carried out by the consumer during the pre-treatment or primary wash cycle of the domestic washing machine.
  • the consumer may also use a co-composition as described herein which can suitably be added to the rinse cycle of the washing process.
  • the co-composition can be optionally used every time that the garment is laundered.
  • the compositions of the invention can be used to re-apply a pre-treatment to the garment on a periodic basis.
  • the frequency of pre-applying the compositions of the present invention can be varied depending on the degree of color protection desired by the consumer.
  • a typical re-application may commence after every 3 or 4 washing cycles to maintain a good level of color protection.
  • compositions of the present invention are non-limiting examples of the compositions of the present invention.
  • Co-polymer comprising acrylamide and N,N,N-trimethyaminoethylacrylate in a ratio of 9: 1.
  • compositions which can be used with the denim compositions 1-16 herein above to form a SYSTEM according to the present invention.
  • Polyalkyleneimine having a molecular weight of 1800 and an average ethoxylation per backbone nitrogen of approximately 4.
  • Polyalkyleneimine having a molecular weight of 1800 and an average ethoxylation per backbone nitrogen of approximately 1.
  • Polyalkyleneimine having a molecular weight of 1800 and an average ethoxylation per backbone nitrogen of approximately 7.
  • Suitable enzymes include cellulase, lipase, protease, peroxidase, and mixtures thereof.
  • Dye fixing agent ex Clariant under the tradename Cartafix CB ® .
  • Dye fixing agent ex Clariant under the tradename Cartafix CB ® .
  • Polyvinylpyrrolidone K85 available ex BASF as Luviskol ® K85.
  • Dye fixing agent ex Clariant under the tradename Cartafix CB ® .
  • Dye fixing agent ex Clariant under the tradename Cartafix CB ® .

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  • Chemical & Material Sciences (AREA)
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Abstract

La présente invention concerne des compositions de protection de couleur pour tissus, qui permettent de protéger du tissu en denim d'une perte de couleur. Ces compositions comprennent un ou plusieurs composés d'amélioration de tissu en denim, qui permettent de réduire la perte de couleur du tissu en denim. Ces compositions comprennent A) à partir d'environ 0,1 % en poids d'un polymère, d'un copolymère ou de mélanges de ceux-ci, ledit polymère ou copolymère comprenant une ou plusieurs unités qui ont un groupe cationique et permettant d'atténuer et/ou de réduire la perte de couleur du tissu en denim; et B) le reste constitué d'excipients et d'adjuvants.
EP00916664A 2000-01-18 2000-03-24 Compositions empechant la perte de couleur par abrasion sur du tissu en denim Withdrawn EP1240382A1 (fr)

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ES2260312T3 (es) * 2000-12-11 2006-11-01 Unilever Plc Composicon para el cuidado de productos textiles.
GB0126280D0 (en) * 2001-11-01 2002-01-02 Unilever Plc Liquid detergent compositions
DE10226846B4 (de) * 2002-06-15 2005-05-12 Brauns-Heitmann Gmbh & Co. Kg Verwendung eines Komponentensystems zum Färben von Jeans-Stoffen
US8556993B2 (en) * 2005-06-15 2013-10-15 Basf Se Laundering process for whitening synthetic textiles
US20160237382A9 (en) * 2005-06-15 2016-08-18 Basf Se Laundering process for whitening synthetic textiles
US10982381B2 (en) 2014-10-06 2021-04-20 Natural Fiber Welding, Inc. Methods, processes, and apparatuses for producing welded substrates
US10011931B2 (en) 2014-10-06 2018-07-03 Natural Fiber Welding, Inc. Methods, processes, and apparatuses for producing dyed and welded substrates
US11766835B2 (en) 2016-03-25 2023-09-26 Natural Fiber Welding, Inc. Methods, processes, and apparatuses for producing welded substrates
KR102304833B1 (ko) 2016-05-03 2021-09-24 네추럴 파이버 웰딩 인코포레이티드 염색되고 용접된 기재를 제조하기 위한 방법, 공정, 및 장치
CN108084343B (zh) * 2017-11-20 2020-06-26 杭州美高华颐化工有限公司 一种无甲醛固色剂的制备方法

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JPH0647792B2 (ja) * 1986-05-28 1994-06-22 三洋化成工業株式会社 染料固着剤
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