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WO1996026314A1 - Traitement d'etoffes - Google Patents

Traitement d'etoffes Download PDF

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Publication number
WO1996026314A1
WO1996026314A1 PCT/GB1995/002447 GB9502447W WO9626314A1 WO 1996026314 A1 WO1996026314 A1 WO 1996026314A1 GB 9502447 W GB9502447 W GB 9502447W WO 9626314 A1 WO9626314 A1 WO 9626314A1
Authority
WO
WIPO (PCT)
Prior art keywords
textile
maleic
cellulosic
maleic acid
polymer
Prior art date
Application number
PCT/GB1995/002447
Other languages
English (en)
Inventor
Vinod Kumar Kansal
Ranjan Vaman Salunkhe
Ramiah Arumugaswamy
Pushpito Kumar Ghosh
Clifford Dominic Rodricks
Original Assignee
Imperial Chemical Industries Plc
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 Imperial Chemical Industries Plc filed Critical Imperial Chemical Industries Plc
Publication of WO1996026314A1 publication Critical patent/WO1996026314A1/fr

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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
    • D06M13/203—Unsaturated carboxylic acids; Anhydrides, halides or salts thereof
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof

Definitions

  • the present invention relates to a method of treating fab ⁇ cs or yarns to make them or fab ⁇ cs made from them more resistant to w ⁇ nkles and/or creases and in particular to such a method that does not use compounds de ⁇ ved from formaldehyde or compounds that liberate formaldehyde on treatment of the fab ⁇ c and/or yam or on subsequent use.
  • the invention relates to such a process for treating cellulosic fab ⁇ cs and/or yarns or blends containing such cellulosic mate ⁇ als.
  • Fab ⁇ cs or garments having cotton upon such treatment retain their dimensions, smooth appearances and normal shapes while in use and also during machine wash or tumble dry processes.
  • Commercially, such treatment of cellulosic mate ⁇ als is typically earned out by high speed, durable press finishing processes using formaldehyde or formaldehyde addition products, such as those with urea or cyclic urea, carbamate esters or with other amides.
  • the treatment agents are applied to typically cotton textiles with an acid catalyst, and heated to induce crosslinking.
  • US Patent 4975209 discloses cellulose crosslinking agents which are polycarboxylic acids including aliphatic, aiicyciic and aromatic acids which are reported as good crosslinking agents at elevated temperatures in the presence of acidic or weakly basic salts.
  • the treated textiles show good wrinkle resistance and smooth drying properties durable to repeated launde ⁇ ng in alkaline detergents.
  • a further US Patent 4820307 to Welch et al also discloses particular types of polycarboxylic acids such as maleic. cit ⁇ c and butanetetracarboxylic acids as cross linking agents in the presence of phosphorus containing catalysts.
  • US Patent 5042986 desc ⁇ bes crosslinking cellulose using cyclic aliphatic polycarboxylic acids having two adjacent carboxyl groups in the trans-configuration.
  • Canadian Patent 2097483 also desc ⁇ bes este ⁇ fication and crosslinking of cellulose in textiles using polycarboxylic acids having more than two carboxylic acids, at elevated temperatures with bone acid or a ⁇ e ⁇ vatrve as crosslinking catalyst.
  • BTCA 1,2,3,4-butanetetracarboxylic acid
  • cit ⁇ c acid Two polycarboxylic acids which have evoked industrial interest are 1,2,3,4-butanetetracarboxylic acid (BTCA) and cit ⁇ c acid.
  • BTCA is one of the most effective crease resist resins and has been marketed by Glo-Tex Inc. as Reactisol DP-4, but very expensive and difficult to synthesise (Reactisol DP-4, Glo-Tex Chemicals, Inc. P. O. Box 400, Roebuck, S. C. 29376).
  • the present invention is based on our discovery that oligome ⁇ c and/or polyme ⁇ c compounds de ⁇ ved from repeat units of maleic acid and/or anhyd ⁇ de can be used as effective treatment agents for cellulosic materials to improve their crease resistance.
  • these agents work by crosslinking cellulose molecules in the fabrics by forming ester bonds with hydroxyl groups in the cellulose molecules and for convenience we refer to this mechanism herein.
  • the particular chemical mechanism is not itself critical to this invention.
  • this invention provides a method of treating a fibrous cellulosic textile mate ⁇ al, particularly to improve its crease resistance, which method comp ⁇ ses treating the textile with a treatment agent comprising one or more ol ⁇ gomer(s) and/or polymer(s) of maleic anhydride and/or maleic acid, and thereafter heating the treated textile to cure the treatment agent onto the fibres of the cellulosic textile.
  • the substrate that is treated in this invention is desc ⁇ bed as a fibrous cellulosic textile mate ⁇ al.
  • the substrate is cellulosic or contains, typically, from 30 to 100% fibres of cellulosic mate ⁇ al.
  • Typical cellulosic fibre mate ⁇ als which can be included in fab ⁇ cs treated according to this inventions include cotton, flax, rayon, jute, hemp and ramie.
  • the cellulosic mate ⁇ al can be a blend of fibres of cellulosic materials with non-cellulosic mate ⁇ als and in particular includes blends of cellulosic fibres, particularly cotton, with polyester, particularly polyethylene terephthalate polymer or related copolymers.
  • the textile can be a woven (including knitted) or non-woven textile, but as crease resistance is particularly important in clothing, the textile will usually be a clothing textile mate ⁇ al.
  • the present invention includes a novel formaldehyde free method of treating , particularly for imparting w ⁇ nkle/crease resistance and smooth drying/shape retention properties to, cellulosic or cellulose containing textiles, particularly containing 30-100% cellulosic materials, which comp ⁇ ses treating the textile mate ⁇ al with one or more oligome ⁇ c and/or polymeric maleic acid and/or anhyd ⁇ de.
  • the abbreviation OMA used herein refers to oligomers and/or polymers of maleic anhydride and/or acid.
  • the oligomers and polymers used include 3 or more maleic acid and/or anhydride units per molecule.
  • the OMA used in the invention will have a molecular weight of from about 300 to 100000, particularly from about 300 to 15000 and more particularly 300 to 2000.
  • oligome ⁇ c maleic acid is sometimes used herein and this term includes oligome ⁇ c and polyme ⁇ c maleic acid and/or anhyd ⁇ de as set out above.
  • This invention includes a method of treating , particularly for imparting w ⁇ nkle/crease resistance and smooth drying/shape retention properties to. cellulosic or cellulosic containing textile mate ⁇ als which comp ⁇ ses treating the textile mate ⁇ al with an oligomer and/or polymer of maleic anhydride and/or acid, having 3 or more maleic anhydride or acid units.
  • the process of the invention includes treating the cellulose or cellulose containing textile mate ⁇ als with oligome ⁇ c and/or polyme ⁇ c maleic anhyd ⁇ de and/or acid in the presence of at least one cu ⁇ ng catalyst and then heat curing the treated textile to produce este ⁇ fication and crosslinking of the cellulose with the oligome ⁇ c and/or polyme ⁇ c maleic anhydnde and/or acid.
  • the invention also includes cloth treated by the method of the invention and in particular, a cellulosic textile material, which may be woven (including knotted) or non-woven, which car ⁇ es residues of o gome ⁇ c and/or polymeric maleic acid and/or anhyd ⁇ de este ⁇ fied to hydroxylic sites in the cellulose. More particularly, the method of the invention employs an aqueous solution containing about 0.1 to 30% by weight of oligome ⁇ c/polyme ⁇ c maleic acid having average molecular weight from 300 to 100000, preferably from about 300 to about 15000 and more particularly from 300 to 2000.
  • the lower molecular weight oligome ⁇ c and/or polyme ⁇ c maleic acids and/or anhyd ⁇ des of this invention work best because they can penetrate more easily into the yams of the fabric and. therefore, the lower molecular weight oligome ⁇ c and polyme ⁇ c acids are preferred. This is most surp ⁇ sing since none of the p ⁇ or art which report the use of polycarboxylic acids point out.
  • the present invention includes a method of treating a cellulosic or cellulose containing textile mate ⁇ al, particularly to produce improved fab ⁇ c mate ⁇ al having wnnkle/crease resistance and smooth drying properties, which method comp ⁇ ses treating the cellulosic textile mate ⁇ al with an aqueous solution containing at least one oligomer and/or polymer of maleic acid and/or anhydride having an average molecular weight in the range of from 300 to 100000 and one or more cu ⁇ ng catalyst and heating the treated mate ⁇ al to cause esterification and crosslinking of said mate ⁇ al with said crosslinking agent to produce said improved fab ⁇ c mate ⁇ al.
  • oligomenc and/or polyme ⁇ c maleic acid and/or anhyd ⁇ de includes repeat units:
  • each M is independently H, a metal, particularly an alkali metal, or ammonium; and the number of such repeat units in the oligomer and/or polymer averages from about 3 to about 1000 (corresponding to the aDove described molecular weight ranges).
  • the particular concentration of oligomenc maleic acid used in the treating solution will depend uoon the degree of cross linking desired and on the proportion of cellulosic fibres in fab ⁇ c being treated.
  • any convenient concentration of the crosslinking agent may be selected depending upon the degree of crosslinking desired, the preferred range being from about 0.1 to 30% by weight more usually and desirably 0.5 to 20% by weight.
  • the amount of OMA applied to the fab ⁇ c will typically be from 1 to 10%, particularly from about 2 to about 7%, by weight of OMA based on the dry fab ⁇ c weight.
  • the oligomers and polymers of maleic anhyd ⁇ de and/or acid used in this invention can be synthesized by known methods, particularly by free radical polyme ⁇ sation starting with maleic acid and/or anhyd ⁇ de, for example initiated by peroxides or other similar free radical initiators Methods of synthesis of the oligomers and polymers use dm this invention are desc ⁇ bed, for example as 5 described in FR 1544728, US 4260724 DE 2405284 A, DE 2732628 A Makromol Chem , 53.
  • the treatment of the fab ⁇ c will usually be earned out in the presence of a cu ⁇ ng catalyst.
  • the treatment solution typically includes a suitable cu ⁇ ng catalyst at a concentration usually of about 0 1 to 30% by weight Amounts outside this range can be used, but will usually be less desirable
  • the catalyst is typically used at a level of from 5 to
  • the catalyst can be an este ⁇ fication catalyst for example as is desc ⁇ bed in more detail below
  • Typical catalysts are este ⁇ fication catalysts
  • suitable catalysts include mineral acids 0 such as hydrochlo ⁇ c, sulphu ⁇ c, fluorobo ⁇ c, phospho ⁇ c, phosphorous and hypophosphorus acids; organic acids such as glycolic. maleic, lactic, cit ⁇ c, tarta ⁇ c and oxalic acids, metal, particularly alkali metal e.g sodium, potassium and lithium, salts of the above acids; metallic salts such as magnesium or zinc, chlo ⁇ de, nitrate, sulphate, fluoroborate or fluorosilicate, ammonium chlo ⁇ de or nitrate, aluminium chionde.
  • mineral acids 0 such as hydrochlo ⁇ c, sulphu ⁇ c, fluorobo ⁇ c, phospho ⁇ c, phosphorous and hypophosphorus acids
  • organic acids such as glycolic. maleic, lactic, cit ⁇ c, tarta ⁇ c and oxalic acids, metal, particularly alkali metal e.g sodium,
  • tetra- sodium and/or potassium pyrophosphate penta- sodium and/or potassium t ⁇ polyphosphate, sodium and/or potassium hexametaphosphate and/or t ⁇ metaphosphate or sodium tetrametaphosphate; 30 boron acids such as bone acid and their denvatives such as orthobo ⁇ c acid, alkali or alkaline earth metal salts of polybo ⁇ c acids or borate esters of the formula B(OR) 3 , where R is alkyl or aryl, amme hydrochlo ⁇ des, such as 2-am ⁇ no-2-methyl-propanol hydrochlo ⁇ de and similar products
  • the catalyst compounds can be used alone or in combination
  • the curing catalyst used is typically used in the treatment solution in a concentration of from 0 1 to 20% by weight
  • concentration of from 0 1 to 20% by weight
  • the precise amount or concentration used will depend on the particular application and we expect that those skilled in the art will not have difficulty in choosing approp ⁇ ate amounts and/or concentrations
  • the invention includes a method of treating a fibrous cellulosic textile mate ⁇ al to improve its crease resistance, which method comp ⁇ ses treating the textile with a treatment agent comp ⁇ sing one or more ol ⁇ gomer(s) and/or polymer(s) of maleic anhyd ⁇ de and/or maleic acid and with an este ⁇ fication catalyst, and thereafter heating the treated textile to cure the treatment agent onto the fibres of the cellulosic textile
  • the invention further includes a treatment solution which comp ⁇ ses an aqueous solution of at least in one ol ⁇ gomer(s) and/or polymer(s) of maleic anhyd ⁇ de and/or maleic acid, particularly at a concentration of from 0 1 to 30% by weight of the solution and at least one este ⁇ fication catalyst. particularly at a concentration of from 0 1 to 30% by weight of the solution
  • the invention also includes textile materials treated by the method of the invention or treated using the treatment solution of the invention
  • the method is typically is earned out by first impregnating the cellulosic or cellulosic containing textile mate ⁇ als with the aqueous treating solution Excess liquid can be removed, for example by passing the treated mate ⁇ al through wringers and drying to remove the solvent Typically, the treated mate ⁇ al is then oven cured at an elevated temperature, for example from about 150 to 240°C for a pe ⁇ od of from 5 seconds to 30 minutes, particularly 5 seconds to 5 minutes, to cause cellulose este ⁇ fication and cross linking
  • formaldehyde free used in relation to a method herein means that the method does not release formaldehyde vapours du ⁇ ng the treatment of textiles or fab ⁇ cs to improve their w ⁇ nkle/crease resistance, du ⁇ ng manufacture of garments from finished fab ⁇ c. du ⁇ ng retailing of the garments or apparel goods or use of such goods by consumers
  • wrinkle or crease resistance means that a treated fab ⁇ c is less likely to w ⁇ nkle/crease or has less w ⁇ nkles or crease after being worn or after a laundenng operation than it would have, were it not so treated, after a comparable operation
  • shape retention/smooth drying means that a pre-ironing of textile material fab ⁇ c or cloth treated according to the invention is less likely to wrinkle or lose its ironed shape after being worn than it would had it not been so treated
  • a An oligomer of maleic acid (5 Og), prepared by the literature method (free radical polymerisation in xylene as solvent using benzoyl peroxide aas initiator), sodium hypophosphite (5.0 g), ALN-GM (a glyceryl monolaurate 23-ethoxylate surfactant) (1.0 g) and NP-10 (a nonyl phenol 10-ethoxylate surfactant) (100 mg) were dissolved in deiomsed water (69.0 g). Cotton cloths (10x10 inch; ca 25x25 cm) were dipped in this solution and passed through a w ⁇ nger to pick up 80% weight of the cloth of the treatment solution.
  • Wrinkle recovery angles were than determined by ICI CAMG-26 method (equivalent to AATCC Test Method 66-1990 "Wrinkle Recovery of Fab ⁇ cs: Recovery Angle Method). This method is used for determining the w ⁇ nkle recovery angles of textiles.
  • the w ⁇ nkle resistance of woven textiles is represented in terms of w ⁇ nkle recovery angles. The greater is the w ⁇ nkle recovery angles more is the wnnkle resistance of the fab ⁇ c. The results of this study are set out in Table 1 below.
  • Example 1 was repeated except that the treatment solution was made up using 7 g oligome ⁇ c maleic acid and 7 g sodium hypophosphite.
  • the samples obtained were 2a (cu ⁇ ng at 160°C for 2 minutes) and 2b (cu ⁇ ng at 160°C for 3 minutes).
  • the results of testing as described below are included in Table 1.
  • Control samples were made up using untreated cloth (C1) and cloth treated with a conventional formaldehyde based treatment agent based on dimethylol dihydroxyethyleneurea (DMDHEU) (C2).
  • DMDHEU dimethylol dihydroxyethyleneurea
  • the DMDHEU used in control C2 was Arkofix NC resin (from Hoechst) which contains 70% DMDHEU resin.
  • the test fab ⁇ c was treated with 5% of the weight of fabric DMDHEU resin, in the presence of MgCI 2 (15% based on the weight of the DMDHEU resin).
  • the resin was applied in a double dip. double nip procedure at a wet pick up of about 80%. After applying the resin solution. the fabric was dried and cured at 160°C for 2 minutes. The fabric was then washed with hot running water at 45 - 50°C for 30 minutes, dried in an air forced draft oven for 10 minutes at 90°C and then conditioned (65% RH; 22 - 24°C for 24 hours). Wrinkle/crease recovery angles were determined on the C1 and C2 samples by the method desc ⁇ bed above and the results are included in Table 1 below.
  • the tear strength of treated and untreated fab ⁇ c was measured using a standard tester manufactured by Testing Machines, Inc. following the TMI method 83-10. The results are expressed as the percentage tear strength of treated cloth as compared with an untreated control. The results of tear testing are included in Table 1.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

On traite des étoffes cellulosiques à l'aide d'une solution aqueuse d'un oligomère/polymère d'acide/anhydride maléique (OMA) afin d'améliorer la résistance au froissement. Ce traitement n'implique pas l'utilisation d'un quelconque matériau contenant du formaldéhyde ou libérant celui-ci lors du traitement ou d'une utilisation ultérieure. Des OMA préférés possèdent des poids moléculaires compris entre 300 et 100000, notamment entre 300 et 2000. On effectue habituellement ce traitement en combinaison avec un catalyseur d'estérification, lequel favorise le durcissement de l'OMA sur l'étoffe cellulosique, laquelle peut être entièrement cellulosique ou être mélangée, par exemple avec des polyesters, notamment avec du polyéthylène téréphtalate.
PCT/GB1995/002447 1995-02-24 1995-10-17 Traitement d'etoffes WO1996026314A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9503794.1 1995-02-24
GBGB9503794.1A GB9503794D0 (en) 1995-02-24 1995-02-24 Treatment of fabrics

Publications (1)

Publication Number Publication Date
WO1996026314A1 true WO1996026314A1 (fr) 1996-08-29

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TW (1) TW304211B (fr)
WO (1) WO1996026314A1 (fr)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999039039A1 (fr) * 1998-01-31 1999-08-05 Imperial Chemical Industries Plc Traitement de tissus
WO1999055951A1 (fr) * 1998-04-27 1999-11-04 The Procter & Gamble Company Composition reduisant les plis et les mauvaises odeurs
US6573233B1 (en) 1998-08-25 2003-06-03 The Procter & Gamble Company Wrinkle and malodour reducing composition
EP0952921A4 (fr) * 1997-01-14 2003-06-18 Univ Georgia Res Found Agents de reticulation pour tissus cellulosiques
US6841198B2 (en) 2001-10-18 2005-01-11 Strike Investments, Llc Durable press treatment of fabric
US6989035B2 (en) 2001-10-18 2006-01-24 The Procter & Gamble Company Textile finishing composition and methods for using same
US7008457B2 (en) 2001-10-18 2006-03-07 Mark Robert Sivik Textile finishing composition and methods for using same
US7018422B2 (en) 2001-10-18 2006-03-28 Robb Richard Gardner Shrink resistant and wrinkle free textiles
US7144431B2 (en) 2001-10-18 2006-12-05 The Procter & Gamble Company Textile finishing composition and methods for using same
US7169742B2 (en) 2001-10-18 2007-01-30 The Procter & Gamble Company Process for the manufacture of polycarboxylic acids using phosphorous containing reducing agents
CN100540797C (zh) * 1997-12-12 2009-09-16 韦尔豪泽公司 聚合多羧酸交联的纤维素纤维
EP0976867B1 (fr) * 1998-07-31 2010-03-03 Clariant Finance (BVI) Limited Procédé pour apprêter un textile et bains d'apprêtage

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB693111A (en) * 1950-03-30 1953-06-24 Cluett Peabody & Co Inc Topochemical modification of cellulose textile materials
DE1062664B (de) * 1955-03-09 1959-08-06 Chem Fab Dueren G M B H Verfahren zur wasserdichten und wasserabweisenden Impraegnierung von mit Aluminium oder Zirkonsalzen vorbehandelten Textilgeweben
DE4331328A1 (de) * 1993-09-15 1994-04-07 Thueringisches Inst Textil Verfahren zur Haftverbesserung von Verstärkungsmaterial in thermoplastischen Kunststoffen

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB693111A (en) * 1950-03-30 1953-06-24 Cluett Peabody & Co Inc Topochemical modification of cellulose textile materials
DE1062664B (de) * 1955-03-09 1959-08-06 Chem Fab Dueren G M B H Verfahren zur wasserdichten und wasserabweisenden Impraegnierung von mit Aluminium oder Zirkonsalzen vorbehandelten Textilgeweben
DE4331328A1 (de) * 1993-09-15 1994-04-07 Thueringisches Inst Textil Verfahren zur Haftverbesserung von Verstärkungsmaterial in thermoplastischen Kunststoffen

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0952921A4 (fr) * 1997-01-14 2003-06-18 Univ Georgia Res Found Agents de reticulation pour tissus cellulosiques
CN100540797C (zh) * 1997-12-12 2009-09-16 韦尔豪泽公司 聚合多羧酸交联的纤维素纤维
WO1999039039A1 (fr) * 1998-01-31 1999-08-05 Imperial Chemical Industries Plc Traitement de tissus
WO1999055951A1 (fr) * 1998-04-27 1999-11-04 The Procter & Gamble Company Composition reduisant les plis et les mauvaises odeurs
EP0976867B1 (fr) * 1998-07-31 2010-03-03 Clariant Finance (BVI) Limited Procédé pour apprêter un textile et bains d'apprêtage
US6573233B1 (en) 1998-08-25 2003-06-03 The Procter & Gamble Company Wrinkle and malodour reducing composition
US7008457B2 (en) 2001-10-18 2006-03-07 Mark Robert Sivik Textile finishing composition and methods for using same
US7018422B2 (en) 2001-10-18 2006-03-28 Robb Richard Gardner Shrink resistant and wrinkle free textiles
US7144431B2 (en) 2001-10-18 2006-12-05 The Procter & Gamble Company Textile finishing composition and methods for using same
US7169742B2 (en) 2001-10-18 2007-01-30 The Procter & Gamble Company Process for the manufacture of polycarboxylic acids using phosphorous containing reducing agents
US7247172B2 (en) 2001-10-18 2007-07-24 The Procter & Gamble Company Shrink resistant and wrinkle free textiles
US6989035B2 (en) 2001-10-18 2006-01-24 The Procter & Gamble Company Textile finishing composition and methods for using same
US6841198B2 (en) 2001-10-18 2005-01-11 Strike Investments, Llc Durable press treatment of fabric

Also Published As

Publication number Publication date
GB9503794D0 (en) 1995-04-12
TW304211B (fr) 1997-05-01

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