US3685953A - Dry heat reaction of quaternized epoxides and quaternized chlorohydrins with hydroxylated textiles - Google Patents

Dry heat reaction of quaternized epoxides and quaternized chlorohydrins with hydroxylated textiles Download PDF

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Publication number
US3685953A
US3685953A US853543A US3685953DA US3685953A US 3685953 A US3685953 A US 3685953A US 853543 A US853543 A US 853543A US 3685953D A US3685953D A US 3685953DA US 3685953 A US3685953 A US 3685953A
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United States
Prior art keywords
quaternized
fabric
dyes
blue
treated
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US853543A
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English (en)
Inventor
Georges Cuvelier
Daniel Wattiez
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Institut Francais Textile et Habillement
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Institut Francais Textile et Habillement
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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
    • D06P1/655—Compounds containing ammonium groups
    • D06P1/66—Compounds containing ammonium groups containing quaternary ammonium groups
    • 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
    • D06M13/322—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 nitrogen
    • D06M13/385—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 nitrogen containing epoxy groups
    • 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
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/58—Material containing hydroxyl groups
    • 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
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/58—Material containing hydroxyl groups
    • D06P3/60—Natural or regenerated cellulose
    • D06P3/66—Natural or regenerated cellulose using reactive dyes
    • 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
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92—Synthetic fiber dyeing

Definitions

  • the present invention relates to polyhydroxylised polymers, such as cellulose or insolubilised polyvinyl alcohol, bearing quaternary ammonium functional groups and having improved dyeing properties, and to a both simple and economic process for obtaining these polymers.
  • the invention provides a process for treating a hydroxylised polymer usually of a textile nature to modify its dyeing properties, particularly its afiinity to fibroreactive dyes, wherein: the hydroxylised polymer is impregnated with an aqueous solution comprising an epoxypropyl ammonium salt of formula where R, R" and R" are lower alkyl radicals and X- is an anion, for example sulphate, sulphonate and halide, and a strong base as fixation catalyst, particularly alkaline metal hydroxides such as potassium and sodium hydroxides, at a concentration of 0.5 to 10% by Weight, preferably 0.5 to 4% by weight; excess water is removed from the impregnated polymer; the polymer is dried at 80 to 140 C., preferably 120 C.; and the polymer is rinsed with water.
  • concentration of the epoxypropyl ammonium salt in the aqueous solution corresponds to the content of nitrogen required in the final treated polymer.
  • a precursor compound of the salt for example the corresponding chlorohydrin can also be used.
  • the mode of treatment is generally as follows:
  • a textile material to be treated is impregnated with an aqueous solution of the quaternary ammonuium salt, at a concentration corresponding to the content of nitrogen requisite for the final product, taking into account the yield and the rate of removal of excess water; the fixation reaction is catalysed by strong bases, particularly alkaline metal hydroxides, such as sodium hydroxide and potassium hydroxide, at the relatively low concentration of 0.5 to 10% by weight, preferably of about 0.5 to 4%, in the aqueous solution.
  • the impregnated material is squeezed out to a retention as low as possible (generally 90%), then dried in a ventilated atmosphere at -140 0., preferably 120 C. Continuing this heat treatment a few minutes after complete dryness is often favourable to terminate the fixation reaction.
  • a rinse with water is then sufficient to eliminate any catalyst remaining on the treated textile material.
  • Futhermore in the chosen treatment conditions, there is obtained fo amounts of fixed nitrogen varying from 0.1 to 0.5%, reproducible fixation yields varying from 60 to in relation to the deposited active product. This is at least unexpected, because with epoxyamines, which are related compounds, a treatment in the conditions according to the invention has only given low fixation yields. In this sphere, it has been possible to establish the following facts.
  • ary ammonium for example when the three substituents are methyl groups trimethylamine may be liberated.
  • the textile material thus treated can then be transformed into spinnable soluble derivatives either in the form of acetate or in the form of xanthate in the case of cellulose.
  • the treatment can be envisaged: either on already insolubilised fibres cold by thermal pretreatment;
  • Fibres and films of triacetate and secondary acetate of cellulose can also be dyed, after enlargement treatment, for example, by soaking in a mixture 50/50 by volume of water and acetone, by a large number of dye categories such as direct dyes, fibro-reactive dyes, acid dyes, metalliferous 2/1 complexes for W001, dyes of the soluble phthalocyanine type and dyes which are diazotizable on fibre. Furthermore, the affinity for plasto-soluble dyes is increased in many cases. This is also applicable to the other spinnable or film-forming derivatives of the polyalcohols, such as esters or others.
  • an aqueous paste comprising a non-hydroxylised thickener (for example oil, trimethyl cellulose, or sodium or potassium polyacrylate), 0.5 to 4% of a strong mineral base such as sodium hydroxide and a quaternary ammonium salt of Formula I is applied to an area of a hydroxylised fabric, and then the fabric is subjected to heat treatment at about 100 to 120 C. conveniently by hot air and preferably for 5 to minutes.
  • the fabric may be printed locally or coated on one side with the aqueous paste. After washing a locally modified fabric is obtained.
  • Dyeing the locally modified fabric depending on how the dye affects the unmodified area of the fabric may result in the unmodified areas being of a different shade or of a different colour to the modified areas. If one side of the fabric has been coated, the final product is a fabric having sides of different colour intensity or of different colours.
  • the fabrics can be dyed continuously or semi-continuously by fibro-reactive dyes in a neutral bath solution.
  • the impregnation bath solution may be prepared by simple dissolution of the dye in water without further addition of any alkaline ingredient or other. This tends to stabilize and lengthen the life of the bath solution. It sufiices to full the fabrics in the bath solution then to evaporate or roll up the pieces and to allow the impregnation bath to act a little while, at a moderate temperature (40-50) avoiding any drying, thus migration of the dye.
  • This also constitutes another aspect of the present invention.
  • EXAMPLE 1 A cotton fabric more specifically 25 g. of 130 g./m.
  • the cotton fabric After rinsing and drying, the cotton fabric had a corrected amount of nitrogen of 0.55%, corresponding to a useful yield of the active product of about 55%.
  • test A which follows, shows. Furthermore, when the operation is effected in a full bath, and not by impregnation followed by a heat treatment to dryness as described above, the fixation yield of the active product is very low as test B shows.
  • Test A A sample of bleached g./m. cotton poplin was treated in a full bath in an aqueous solution with 5% epoxypropyl trimethyl ammonium chloride not containing any fixation catalyst: the ratio of the bath was 1/35. The whole was kept for 8 hours at 50 C. avoiding the evaporation of the bath. After rinsing and drying the sample has a content of nitrogen practically identical with that of the untreated fabric i.e. 0.2%. There is, therefore, no reaction in the conditions of the test.
  • the sample is not dyed by Procion Red G in a neutral medium or by Sulfacide Blue 2 RL.
  • Test B The test in the full bath was repeated with an aqueous solution containing 1% sodium hydroxide and 5% epoxypropyl trimethyl ammonium chloride.
  • the cotton fabric After rinsing and drying, the cotton fabric had a corrected amount of nitrogen of 0.21%, which corresponds to a useful yield of the active product of only 18%.
  • EXAMPLE 2 The process according to Example 1 was repeated, except that the treatment temperature was 100 C. instead of 120 C. The useful yield of the active product was 48%.
  • EXAMPLE 3 A cotton fabric was treated in the conditions given in Example 1, but the active product is epoxypropyl diethylmethyl ammonium methyl sulphate:
  • the fixation yield of the deposited nitrogen was 80%.
  • Example 3 was repeated but varying the concentration of the active product in such a manner that the amount of deposited nitrogen was 0.5%. The fixation yield of the active product was then 90%.
  • EXAMPLE 6 A cotton fabric treated in the conditions of Example 1, with an amount of fixed nitrogen of 0.4%, was dyed in Rouge Diazol Lumiere SE, a direct dye. It was ascertained that 1% of the dye gave the same intensity of tone as 3% on the untreated fabric.
  • the firmness indices to water, checked in accordance with the E.C.E. code were as follows:
  • the dyeings obtained did not show any appreciable variation in firmness on relation to standard dyeings, with the same dyes, at the same height of tone on unmodified cotton fabric.
  • EXAMPLE 8 Samples of fabrics of cotton and of polynosic fibres were treated in the conditions of Example 1 with an amount of fixed nitrogen of 0.3%. They were then dyed by means of the following dyes:
  • Example 9 The conditions of Example 4 were used to treat a fabric of acetalysed polyvinyl alcohol fibres (Vinylal). The fixation yield was only 25% The final fabric containing 0.125% of fixed nitrogen proved to possess a very increased affinity for direct dyes, acid dyes, metalliferous 2/2 complexes and fibro-reactive dyes in a neutral medium.
  • EXAMPLE 10 A cotton fabric was treated in the conditions given in Example 1 with an amount of fixed nitrogen of 0.5%. After treatment, this fabric was acetalysed in heterogenous phase by a known process, until an amount of combined acetic acid of 55% The resulting samples of fabric could be dyed by the following dyes after a pre-soaking in a 50/50 mixture of acetone/water.
  • Procion Red G Procion Brilliant Blue RS showing synthesis of the dye Actoquinone Blue Green Actoquinone Pure Blue R 6 Orang Neutrichrome RLL Bleu Sulfacide Blue 2 RL Pandurane Blue B Diazol Blue Lumiere R EXAMPLE 11
  • a paste of linters having a degree of polymerisation of 865 was first treated in accordance with the process of Example 3 then acetylised in accordance with a known process in homogenous phase in a medium of methylene chloride. After precipitation by petroleum ether and washing there was obtained a product having the following characteristics:
  • EXAMPLE 12 Two fabrics manufactured starting from two samples of cotton of the Detapine variety, one with a good maturity and the other of very low ripeness, were treated in the conditions of Example 1, but with an amount of fixed nitrogen of 03%.
  • the treated fabric had a distinctly increased affinity: thus, the cotton fabric of very low ripeness, treated, dyes in a shade of deeper colour than the cotton fabric of good ripeness, not treated.
  • EXAMPLE 13 In this example, instead of using an epoxy ammonium salt as in the preceding examples, there was used the corresponding chlorohydrin considered as the precursor of epoxy ammonium. In these conditions, it is necessary to add to the sodium hydroxide at 1% an additional quantity of NaOH to neutralise the chlorine of the chlorohydrin. Operating by impregnation and heat treatment to dryness, there are obtained fixation yields comparable with those obtained with the epoxy ammonium salts.
  • a sample of cotton poplin of 130 g./m. was fulled in an aqueous solution containing 2% soduim hydroxide and 6% (chloro-3-hydroxy-2)-propyl trimethyl ammonium chloride and squeezed out to a dryness of The sample kept at the initial dimensions was treated for 10 minutes at C. in a current of hot air.
  • the cotton fabric After rinsing and drying, the cotton fabric had a corrected amount of nitrogen of 0.22%, which corresponds to a useful yield of the ammonium of about 55%.
  • the treated fabric is strongly dyed by Rouge Procion G in a neutral medium or Sulfacide Blue 2 RL.
  • Naphtazol TR CI Azoic Coupling Component 8 CI Solid Red Base TR: CI Azoic Diazo Component II CI Solanthrene Blue FRS: CI Vat Blue 4 CI 69800 Procion Red G: CI Reactive Red 5 Procion Brilliant Blue RS: CI Reactive Blue 4 Neutrichrome Orange RLL: CI Acid Orange 121 Acetoquinone Blue Breen R: CI Disperse Blue I CI Sulfacide Blue 2 RL: CI Acid Blue 47 CI 62085 Pandurane Blue I: CI Mordant Blue 77 Diazol Lumiere Blue R: CI Direct Blue 71 CI 34140 Diazamine Luminere Red 5 B: CI Direct Red 117 CI Diazol Lumiere Red 8 B: CI Direct Red 81 CI 28160.
  • alkaline metal hydroxide is selected from the group consisting of potassium and sodium hydroxides.
  • a process for treating a fabric of cellulose, regenerated cellulose or insolubilised polyvinyl alcohol to lo- 0 cally modify its dyeing properties comprises:
  • an epoxypropyl ammonium salt selected from the group consisting of epoxypropyl trimethyl ammonium chloride, epoxypropyl diethylmethyl ammonium methyl sulphate and epoxypropyl diethyl-' ethyl ammonium iodide, and precursors chlorohydrin thereof a strong mineral base as a fixation catalist, and a non-hydroxylised thickener
  • drying step (c) is carried out for a maximum of about 30 minutes.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
US853543A 1968-08-30 1969-08-27 Dry heat reaction of quaternized epoxides and quaternized chlorohydrins with hydroxylated textiles Expired - Lifetime US3685953A (en)

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FR164694 1968-08-30

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US853543A Expired - Lifetime US3685953A (en) 1968-08-30 1969-08-27 Dry heat reaction of quaternized epoxides and quaternized chlorohydrins with hydroxylated textiles
US00266330A Expired - Lifetime US3778225A (en) 1968-08-30 1972-06-26 Reactive dyeing of epoxy alkyl quaternary ammonium cellulose or polyvinyl alcohol textiles

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US00266330A Expired - Lifetime US3778225A (en) 1968-08-30 1972-06-26 Reactive dyeing of epoxy alkyl quaternary ammonium cellulose or polyvinyl alcohol textiles

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US (2) US3685953A (fr)
BE (1) BE737759A (fr)
CH (2) CH1274269A4 (fr)
DE (1) DE1942742C3 (fr)
FR (1) FR1585665A (fr)
GB (1) GB1286535A (fr)

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3778225A (en) * 1968-08-30 1973-12-11 Inst Textile De France Reactive dyeing of epoxy alkyl quaternary ammonium cellulose or polyvinyl alcohol textiles
US4313732A (en) * 1980-10-30 1982-02-02 Burlington Industries, Inc. Process for improving washfastness of indigo-dyed fabrics
US4369041A (en) * 1980-05-12 1983-01-18 Vyzkumny Ustav Zuslechtovaci Technique for dyeing and printing of textiles with quaternary ammonium compound
US4441884A (en) * 1976-12-07 1984-04-10 Sandoz Ltd. Quaternary ammonium compounds and their use as dyeing assistants for polyamide fibers
JPS59216988A (ja) * 1983-05-19 1984-12-07 東洋紡績株式会社 異色染めされたセルロ−ス系繊維製品
JPS60231878A (ja) * 1984-04-27 1985-11-18 東洋紡績株式会社 セルロ−ス系繊維の異色染色方法
JPS60231877A (ja) * 1984-04-27 1985-11-18 東洋紡績株式会社 セルロ−ス系繊維の異色染色法
JPS6290383A (ja) * 1985-10-15 1987-04-24 東洋紡績株式会社 霜降り調捺染布帛
US4775715A (en) * 1987-07-23 1988-10-04 E. I. Du Pont De Nemours And Company Dry blending process for the quaternization of polyvinyl alcohol
US4822851A (en) * 1986-08-07 1989-04-18 Degussa Aktiengesellschaft Process for the preparation of cationized polyvinyl alcohol
US5006125A (en) * 1988-09-13 1991-04-09 The Dow Chemical Company Process for improving the dyeability and whiteness of cellulosic fabrics
US5320646A (en) * 1992-05-22 1994-06-14 The Dow Chemical Company Process for improving the dyeability of fabrics and fibers
US5565007A (en) * 1994-05-17 1996-10-15 Hoechst Aktiengesellschaft Amination of rayon
WO1999018283A1 (fr) * 1997-07-22 1999-04-15 Johnny Joe Kent Procede de teinture a faible consommation d'energie
US6001995A (en) * 1995-05-24 1999-12-14 Dystar Textilfarben Gmbh & Co. Deutschland Kg Water-soluble etherified starches
US20030203116A1 (en) * 2000-06-13 2003-10-30 Milliken & Company Carpet tile renewal process and products
CN108867045A (zh) * 2017-05-09 2018-11-23 中国石油化工股份有限公司 一种压裂用接枝改性维纶纤维及其制备方法
CN109403038A (zh) * 2017-08-17 2019-03-01 中国石油化工股份有限公司 一种阳离子聚合物表面接枝维纶纤维及其制备方法
WO2025002134A1 (fr) * 2023-06-30 2025-01-02 华为技术有限公司 Composition et son utilisation

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2187804B2 (fr) * 1972-06-09 1975-03-07 Inst Textile De France Cellulose echangeuse d'anions et son application au traitement de certaines eaux de rejet industrielles
US4167393A (en) * 1978-08-21 1979-09-11 The Dow Chemical Company Method for binding a water-soluble direct dye to paper
US4380453A (en) 1980-02-06 1983-04-19 Dixie Yarns, Inc. Extraneous dye or colorant scavenging system in laundry
US4374639A (en) 1980-04-03 1983-02-22 Dixie Yarns, Inc. System for preventing static electricity on laundered textile materials
FR2511001B1 (fr) * 1981-08-10 1988-07-29 Gosse Filature Produits de traitement des polymeres polyhydroxyles ou polyamines ainsi que procede utilisant ces produits
FR2530589B1 (fr) * 1982-07-20 1986-01-03 Anvar Materiau permettant de laver dans un meme bain un melange d'articles textiles et procede de lavage mettant en oeuvre un tel materiau
GB8620139D0 (en) * 1986-08-19 1986-10-01 Roberts G A F Dyeing of cellulosic fabric
DE4435385A1 (de) * 1994-10-04 1996-04-11 Hoechst Ag Verfahren zum Färben von modifizierten Viskosefasern mit Säure- oder Direktfarbstoffen
US5667533A (en) * 1996-02-07 1997-09-16 The Virkler Company Heather dyed fabric and method of producing same
ES2173452T3 (es) * 1996-06-19 2002-10-16 Little Island Patents Ltd Substrato para la captura de colorantes y procedimiento para su produccion.
GB2519505A (en) * 2013-08-20 2015-04-29 Little Island Patents Ltd Method for manufacturing a dye scavenging substrate
EP3669024B1 (fr) 2017-08-15 2021-06-09 HBI Branded Apparel Enterprises, LLC Matériau fibreux fonctionnalisé
CN119372917A (zh) * 2023-07-26 2025-01-28 鲁泰纺织股份有限公司 纤维素纤维筒子纱的改性方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2136928A (en) * 1934-12-10 1938-11-15 Ig Farbenindustrie Ag Manufacture of amines of high molecular weight, which are rich in nitrogen
NL46333C (fr) * 1935-02-21
US2238949A (en) * 1936-02-06 1941-04-22 Process of modifying the electro
US2762718A (en) * 1949-08-03 1956-09-11 Bayer Ag Textile printing pastes and method of applying
FR1585665A (fr) * 1968-08-30 1970-01-30 Inst Textile De France Nouveaux polymeres hydroxyles a caractere textile ayant des proprietes tinctorales ameliorees, procede de modification des proprietes tinctoriales des polymeres polyhydroxyles, et nouveau procede de teint

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3778225A (en) * 1968-08-30 1973-12-11 Inst Textile De France Reactive dyeing of epoxy alkyl quaternary ammonium cellulose or polyvinyl alcohol textiles
US4441884A (en) * 1976-12-07 1984-04-10 Sandoz Ltd. Quaternary ammonium compounds and their use as dyeing assistants for polyamide fibers
US4369041A (en) * 1980-05-12 1983-01-18 Vyzkumny Ustav Zuslechtovaci Technique for dyeing and printing of textiles with quaternary ammonium compound
US4313732A (en) * 1980-10-30 1982-02-02 Burlington Industries, Inc. Process for improving washfastness of indigo-dyed fabrics
JPS59216988A (ja) * 1983-05-19 1984-12-07 東洋紡績株式会社 異色染めされたセルロ−ス系繊維製品
JPS60231878A (ja) * 1984-04-27 1985-11-18 東洋紡績株式会社 セルロ−ス系繊維の異色染色方法
JPS60231877A (ja) * 1984-04-27 1985-11-18 東洋紡績株式会社 セルロ−ス系繊維の異色染色法
JPS6290383A (ja) * 1985-10-15 1987-04-24 東洋紡績株式会社 霜降り調捺染布帛
US4822851A (en) * 1986-08-07 1989-04-18 Degussa Aktiengesellschaft Process for the preparation of cationized polyvinyl alcohol
EP0255854A3 (en) * 1986-08-07 1989-11-02 Degussa Aktiengesellschaft Process for the manufacture of cationic poly(vinyl alcohols)
US5001191A (en) * 1986-08-07 1991-03-19 Degussa Aktiengesellschaft Process for dry cationization of polyvinyl alcohol
US4775715A (en) * 1987-07-23 1988-10-04 E. I. Du Pont De Nemours And Company Dry blending process for the quaternization of polyvinyl alcohol
US5006125A (en) * 1988-09-13 1991-04-09 The Dow Chemical Company Process for improving the dyeability and whiteness of cellulosic fabrics
US5320646A (en) * 1992-05-22 1994-06-14 The Dow Chemical Company Process for improving the dyeability of fabrics and fibers
EP0574151B1 (fr) * 1992-05-22 1997-07-02 The Dow Chemical Company Procédé pour améliorer la tinctabilité de tissus et fibres
US5565007A (en) * 1994-05-17 1996-10-15 Hoechst Aktiengesellschaft Amination of rayon
US6001995A (en) * 1995-05-24 1999-12-14 Dystar Textilfarben Gmbh & Co. Deutschland Kg Water-soluble etherified starches
WO1999018283A1 (fr) * 1997-07-22 1999-04-15 Johnny Joe Kent Procede de teinture a faible consommation d'energie
US20030203116A1 (en) * 2000-06-13 2003-10-30 Milliken & Company Carpet tile renewal process and products
US6989037B2 (en) * 2000-06-13 2006-01-24 Milliken & Company Carpet tile renewal process and products
CN108867045A (zh) * 2017-05-09 2018-11-23 中国石油化工股份有限公司 一种压裂用接枝改性维纶纤维及其制备方法
CN108867045B (zh) * 2017-05-09 2021-02-23 中国石油化工股份有限公司 一种压裂用接枝改性维纶纤维及其制备方法
CN109403038A (zh) * 2017-08-17 2019-03-01 中国石油化工股份有限公司 一种阳离子聚合物表面接枝维纶纤维及其制备方法
WO2025002134A1 (fr) * 2023-06-30 2025-01-02 华为技术有限公司 Composition et son utilisation

Also Published As

Publication number Publication date
BE737759A (fr) 1970-02-02
DE1942742A1 (de) 1970-03-05
FR1585665A (fr) 1970-01-30
DE1942742B2 (de) 1980-04-10
CH552096A (fr) 1974-07-31
US3778225A (en) 1973-12-11
GB1286535A (en) 1972-08-23
DE1942742C3 (de) 1980-12-04
CH1274269A4 (fr) 1974-02-28

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