EP0564346B1 - Apprêtage de textiles avec des compositions contenant de l'acide phosphinicosuccinique, de l'acide phosphinicobissuccinique ou leur mélange - Google Patents

Apprêtage de textiles avec des compositions contenant de l'acide phosphinicosuccinique, de l'acide phosphinicobissuccinique ou leur mélange Download PDF

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Publication number
EP0564346B1
EP0564346B1 EP93400806A EP93400806A EP0564346B1 EP 0564346 B1 EP0564346 B1 EP 0564346B1 EP 93400806 A EP93400806 A EP 93400806A EP 93400806 A EP93400806 A EP 93400806A EP 0564346 B1 EP0564346 B1 EP 0564346B1
Authority
EP
European Patent Office
Prior art keywords
acid
phosphinicosuccinic
finishing
mixture
textiles
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.)
Expired - Lifetime
Application number
EP93400806A
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German (de)
English (en)
French (fr)
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EP0564346A1 (fr
Inventor
Didier Wilhelm
Antonio Gelabert
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.)
Clariant Finance BVI Ltd
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Francaise Hoechst Ste
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Application filed by Francaise Hoechst Ste filed Critical Francaise Hoechst Ste
Publication of EP0564346A1 publication Critical patent/EP0564346A1/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
    • D06M13/244—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 sulfur or phosphorus
    • D06M13/282—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 sulfur or phosphorus with compounds containing phosphorus
    • D06M13/285—Phosphines; Phosphine oxides; Phosphine sulfides; Phosphinic or phosphinous acids or derivatives thereof
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2369—Coating or impregnation improves elasticity, bendability, resiliency, flexibility, or shape retention of the fabric
    • Y10T442/2393—Coating or impregnation provides crease-resistance or wash and wear characteristics

Definitions

  • the present invention relates to a process for dressing cellulosic textiles, a dressing bath for textiles using phosphinicosuccinic acid, phosphinicobissuccinic acid or mixtures thereof, prepared cellulosic textiles and the use of said acids as finishes and as cellulose crosslinking agents.
  • Textile finishes are currently commonly used to impart wrinkle-resistant properties to cellulosic fabrics, but most contain free or combined formaldehyde, which is released either in the sizing workshops or when the fabrics so finished are used.
  • Phosphinicosuccinic acid (I) as well as phosphinicobissuccinic acid (II) are described in the literature (United States patent No. 5018577). They are especially obtained by adding an alkali metal hypophosphite such as sodium hypophosphite on maleic acid, a dialkyl maleate or maleic anhydride followed, if necessary, by acidic or basic hydrolysis of the ester functions, when a dialkyl maleate is used as the starting product.
  • This addition reaction is generally catalyzed with a mineral peroxide derivative such as sodium persulfate, or organic such as 2-ethyl tert-butyl perhexanoate, TBPEH; it can also be carried out under ultraviolet radiation within acetone (FR-A-2356658, US-A-4138431, US-A-4590014, US-A-4632741, US-A-5023000, US-A- 5018577, US-A-4088678 and Beil. IV, 4th supplement, page 3497, 1959).
  • a mineral peroxide derivative such as sodium persulfate, or organic such as 2-ethyl tert-butyl perhexanoate, TBPEH
  • US-A-4820307 describes maleic acid as a possible crosslinking agent for cellulose textiles in the presence of sodium hypophosphite as catalyst.
  • the polycarboxylic acid forms cyclic anhydrides which add up on the alkali metal hypophosphite to give acylphosphinates and the acylphosphinate formed reacts with the cellulose to give crosslinked esters of the carboxylic acid. and regenerate the hypophosphite catalyst.
  • Phosphinicosuccinic acid (I) and phosphinicobissuccinic acid (II), as well as their mixtures in variable proportions, have, as has been said previously, very interesting properties of crosslinking of cellulose, which justify their application as 'textile finishes, to give cellulosic fabrics wrinkle-resistant properties.
  • the subject of the present invention is therefore a process for preparing cellulosic textiles, characterized in that the cellulosic textile to be treated is impregnated using an aqueous finishing bath comprising phosphinicosuccinic acid (I), phosphinicobissuccinic acid (II), or a mixture of these two acids. This mixture can be in variable proportions.
  • the textile dressing bath is partially neutralized with an alkali metal hydroxide in order to obtain an aqueous finishing bath having a pH of 2 to 7.
  • the finishes described above are characterized in that they do not contain catalyst, of any nature whatsoever.
  • the present application also relates to a finishing bath for cellulosic textiles, characterized in that it comprises an aqueous solution of phosphinicosuccinic acid (I), of phosphinicobissuccinic acid (II), or of their mixture, the bath having was partially neutralized at pH 2 to 7 using an alkali metal hydroxide, as well as a wetting agent, and in particular the baths described in examples 3 and 4.
  • the present application also relates to finished cellulosic textiles, characterized in that they are obtained by the implementation of the process described above.
  • the present application also relates to the use, as a finish of a cellulosic textile, of phosphinicosuccinic acid (I), of phosphinicobissuccinic acid (II), or of a mixture thereof.
  • the present application finally relates to the use of phosphinicosuccinic acid (I), phosphinicobissuccinic acid (II) or their mixtures in variable proportions, as crosslinking agents for the cellulose contained in particular in fibers textiles, wood shavings, sawdust.
  • the anti-crease test is carried out according to the AATCC 66-1972 standard on samples as they are and on samples subjected to three household washes at 60 ° C; the wrinkle resistance is expressed by the sum of the wrinkle angles obtained in warp and weft direction.
  • the tensile strength of the samples expressed in daN in the warp direction plus in the weft direction is produced according to standard AFNOR G 07.001.
  • the yellowing of the tissues carried out on a FIXOTEST device at 200 ° C for 30 seconds and the whiteness expressed in Berger degrees, are measured with a spectrophotometer.
  • the residual formaldehyde level on tissue was determined according to the method described in Japanese law 112-1973; in the fabrics of the examples, no formaldehyde could be detected.
  • This product dosed by potentiometry, contains 15.49 meq / g of acid functions, of which 2.756 meq / g of strong acid functions, or a ratio between carboxylic acid function and phosphinic acid function of 4.62: 1 (theory 4: 1).
  • a 100% cotton poplin fabric, scalded and bleached, is impregnated with the scarf, weighing approximately 130 g per square meter with an expressing rate of 75% in an aqueous bath, the pH of which has been adjusted with soda at the value indicated in table I, containing in solution the amounts of acid, as well as 2 g per liter of ethoxylated nonylphenol with 10 moles of ethylene oxide as wetting agent.
  • the fabric is then dried for 45 seconds at 120 ° C, then it is subjected on a laboratory oar to a heat treatment for 90 seconds at 180 ° C.
  • Comparison example C1 corresponds to the untreated tissue.
  • Example 5 is repeated, replacing the sodium persulfate with an equivalent quantity of ammonium persulfate. This gives about 1464 g of a clear, colorless aqueous solution containing about 2.5 moles of phosphinicobissuccinic acid monosodium, having an acidity of 6.96 meq / g (theory 6.83 meq / g) and no longer containing maleic anhydride determined by NMR analysis of the proton and carbon thirteen.
  • This solution, designated E is used in this form in Example 9.

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
EP93400806A 1992-04-03 1993-03-29 Apprêtage de textiles avec des compositions contenant de l'acide phosphinicosuccinique, de l'acide phosphinicobissuccinique ou leur mélange Expired - Lifetime EP0564346B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR9204076A FR2689529B1 (fr) 1992-04-03 1992-04-03 Procede d'appretage de textiles, bain d'appretage pour textiles utilisant de l'acide phosphinicosuccinique, de l'acide phosphinicobisuccinique ou leurs melanges.
FR9204076 1992-04-03

Publications (2)

Publication Number Publication Date
EP0564346A1 EP0564346A1 (fr) 1993-10-06
EP0564346B1 true EP0564346B1 (fr) 1997-01-15

Family

ID=9428441

Family Applications (1)

Application Number Title Priority Date Filing Date
EP93400806A Expired - Lifetime EP0564346B1 (fr) 1992-04-03 1993-03-29 Apprêtage de textiles avec des compositions contenant de l'acide phosphinicosuccinique, de l'acide phosphinicobissuccinique ou leur mélange

Country Status (12)

Country Link
US (2) US5300240A (es)
EP (1) EP0564346B1 (es)
JP (1) JP3217894B2 (es)
KR (1) KR100257986B1 (es)
AT (1) ATE147805T1 (es)
CA (1) CA2091656A1 (es)
DE (1) DE69307375T2 (es)
DK (1) DK0564346T3 (es)
ES (1) ES2096235T3 (es)
FR (1) FR2689529B1 (es)
GR (1) GR3022662T3 (es)
TR (1) TR26711A (es)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2689529B1 (fr) * 1992-04-03 1995-06-23 Hoechst France Procede d'appretage de textiles, bain d'appretage pour textiles utilisant de l'acide phosphinicosuccinique, de l'acide phosphinicobisuccinique ou leurs melanges.
US5496476A (en) * 1992-12-21 1996-03-05 Ppg Indutstries, Inc. Non-formaldehyde durable press finishing for cellulosic textiles with phosphonoalkylpolycarboxylic acid
US5496477A (en) * 1992-12-21 1996-03-05 Ppg Industries, Inc. Non-formaldehyde durable press finishing for cellulosic textiles with phosphinocarboxylic acid
FR2781821B1 (fr) * 1998-07-31 2000-11-10 Clariant France Sa Procede pour appreter un textile et bains d'appretage
US7169293B2 (en) * 1999-08-20 2007-01-30 Uop Llc Controllable space velocity reactor and process
AU2001227803A1 (en) 2000-01-14 2001-07-24 Rhodia Inc. Crosslinking agents for textile finishing baths
CA2574769A1 (en) * 2004-06-24 2006-02-02 Dow Global Technologies Inc. Stretch fabrics with wrinkle resistance
JP4248466B2 (ja) * 2004-09-03 2009-04-02 株式会社島精機製作所 繊維製品の染色方法
JP2006316372A (ja) * 2005-05-11 2006-11-24 Tokai Senko Kk セルロース系繊維の洗濯変色防止加工方法
US7842627B2 (en) * 2006-11-30 2010-11-30 Dow Global Technologies Inc. Olefin block compositions for stretch fabrics with wrinkle resistance
US8748365B2 (en) 2012-09-13 2014-06-10 Ecolab Usa Inc. Solidification matrix comprising phosphinosuccinic acid derivatives
US9994799B2 (en) 2012-09-13 2018-06-12 Ecolab Usa Inc. Hard surface cleaning compositions comprising phosphinosuccinic acid adducts and methods of use
US20140308162A1 (en) 2013-04-15 2014-10-16 Ecolab Usa Inc. Peroxycarboxylic acid based sanitizing rinse additives for use in ware washing
US9752105B2 (en) 2012-09-13 2017-09-05 Ecolab Usa Inc. Two step method of cleaning, sanitizing, and rinsing a surface
US8871699B2 (en) 2012-09-13 2014-10-28 Ecolab Usa Inc. Detergent composition comprising phosphinosuccinic acid adducts and methods of use
US9023784B2 (en) 2012-09-13 2015-05-05 Ecolab Usa Inc. Method of reducing soil redeposition on a hard surface using phosphinosuccinic acid adducts
US11149202B1 (en) 2016-12-13 2021-10-19 Ecolab Usa Inc. Tetracarboxylic acid combinations for corrosion inhibition
CN109137526B (zh) * 2018-08-30 2021-01-29 常州大学 一种无甲醛抗皱整理剂的制备方法及应用

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4088678A (en) * 1976-07-01 1978-05-09 Nalco Chemical Company Substituted succinic acid compounds and their use as chelants
US4820307A (en) * 1988-06-16 1989-04-11 The United States Of America As Represented By The Secretary Of Agriculture Catalysts and processes for formaldehyde-free durable press finishing of cotton textiles with polycarboxylic acids
US5018577A (en) * 1990-08-02 1991-05-28 Nalco Chemical Company Phosphinate inhibitor for scale squeeze applications
US5023000A (en) * 1990-05-10 1991-06-11 Nalco Chemical Company Oligomer-containing phosphate scale inhibitors

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3300337A (en) * 1960-10-06 1967-01-24 Stauffer Chemical Co Anti-static coated textile fiber
US3535073A (en) * 1967-10-25 1970-10-20 Us Agriculture Crosslinking cotton with haloalkyl phosphine oxides
US3979533A (en) * 1972-12-04 1976-09-07 The United States Of America As Represented By The Secretary Of Agriculture α,α'-Bis-(phosphono)dicarboxylic acid derivatives
US4138431A (en) * 1978-06-29 1979-02-06 Nalco Chemical Company Reaction of α-phosphorus containing carboxylic acids with phosphorous acid to prepare scale and corrosion inhibitors
SE8101633L (sv) * 1980-03-14 1981-09-15 Wool Dev Int Textilbehandling
US4632741A (en) * 1984-09-06 1986-12-30 Economics Laboratory, Inc. Synthesis of alkyl phosphinate salts and bis(alkyl) phosphinate salts
US4590014A (en) * 1984-09-06 1986-05-20 Economics Laboratory, Inc. Synthesis of alkyl phosphinate salts
US4936865A (en) * 1988-06-16 1990-06-26 The United States Of America As Represented By The Secretary Of Agriculture Catalysts and processes for formaldehyde-free durable press finishing of cotton textiles with polycarboxylic acids
FR2668506B1 (fr) * 1990-10-30 1993-02-12 Hoechst France Applications de derives d'acides alkanepolycarboxyliques comme agents de reticulation de la cellulose, nouveaux derives et apprets textiles.
FR2689529B1 (fr) * 1992-04-03 1995-06-23 Hoechst France Procede d'appretage de textiles, bain d'appretage pour textiles utilisant de l'acide phosphinicosuccinique, de l'acide phosphinicobisuccinique ou leurs melanges.

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4088678A (en) * 1976-07-01 1978-05-09 Nalco Chemical Company Substituted succinic acid compounds and their use as chelants
US4820307A (en) * 1988-06-16 1989-04-11 The United States Of America As Represented By The Secretary Of Agriculture Catalysts and processes for formaldehyde-free durable press finishing of cotton textiles with polycarboxylic acids
US5023000A (en) * 1990-05-10 1991-06-11 Nalco Chemical Company Oligomer-containing phosphate scale inhibitors
US5018577A (en) * 1990-08-02 1991-05-28 Nalco Chemical Company Phosphinate inhibitor for scale squeeze applications

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
US7247172B2 (en) 2001-10-18 2007-07-24 The Procter & Gamble Company Shrink resistant and wrinkle free textiles

Also Published As

Publication number Publication date
US5385680A (en) 1995-01-31
CA2091656A1 (fr) 1993-10-04
US5300240A (en) 1994-04-05
ATE147805T1 (de) 1997-02-15
TR26711A (tr) 1995-05-15
KR100257986B1 (en) 2000-06-01
DE69307375D1 (de) 1997-02-27
JP3217894B2 (ja) 2001-10-15
KR930021876A (ko) 1993-11-23
GR3022662T3 (en) 1997-05-31
FR2689529B1 (fr) 1995-06-23
JPH0633374A (ja) 1994-02-08
ES2096235T3 (es) 1997-03-01
DE69307375T2 (de) 1997-05-15
DK0564346T3 (da) 1997-07-07
FR2689529A1 (fr) 1993-10-08
EP0564346A1 (fr) 1993-10-06

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