WO1989006292A1 - Traitement tinctorial et retardateur de flamme simultane d'aramides - Google Patents

Traitement tinctorial et retardateur de flamme simultane d'aramides Download PDF

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Publication number
WO1989006292A1
WO1989006292A1 PCT/US1988/004074 US8804074W WO8906292A1 WO 1989006292 A1 WO1989006292 A1 WO 1989006292A1 US 8804074 W US8804074 W US 8804074W WO 8906292 A1 WO8906292 A1 WO 8906292A1
Authority
WO
WIPO (PCT)
Prior art keywords
fabric
dyeing
amount
flame retardant
dyed
Prior art date
Application number
PCT/US1988/004074
Other languages
English (en)
Inventor
Phillip H. Riggins
Peter J. Hauser
Original Assignee
Burlington Industries, Inc.
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 Burlington Industries, Inc. filed Critical Burlington Industries, Inc.
Priority to DE3889925T priority Critical patent/DE3889925D1/de
Priority to EP89900978A priority patent/EP0400018B1/fr
Publication of WO1989006292A1 publication Critical patent/WO1989006292A1/fr
Priority to PCT/US1992/009728 priority patent/WO1994011563A1/fr
Priority to AU31328/93A priority patent/AU3132893A/en
Priority claimed from PCT/US1992/009728 external-priority patent/WO1994011563A1/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
    • D06M13/292—Mono-, di- or triesters of phosphoric or phosphorous acids; 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
    • 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
    • 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
    • D06M13/35—Heterocyclic compounds
    • D06M13/352—Heterocyclic compounds having five-membered heterocyclic rings
    • 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
    • D06P1/0004—General aspects of dyeing
    • 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
    • D06P1/64—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 low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/642—Compounds containing nitrogen
    • D06P1/6426—Heterocyclic compounds
    • 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
    • D06P1/64—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 low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/642—Compounds containing nitrogen
    • D06P1/645—Aliphatic, araliphatic or cycloaliphatic compounds containing amino 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
    • 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
    • D06P1/64—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 low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/642—Compounds containing nitrogen
    • D06P1/649—Compounds containing carbonamide, thiocarbonamide or guanyl groups
    • D06P1/6495—Compounds containing carbonamide -RCON= (R=H or hydrocarbons)
    • D06P1/6498—Compounds containing -CONCO-, e.g. phthalimides, hydantoine; Compounds containing RCONHSO2R (R=H or hydrocarbon)
    • 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
    • D06P1/64—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 low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/651—Compounds without nitrogen
    • D06P1/65106—Oxygen-containing compounds
    • D06P1/65131—Compounds containing ether or acetal 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
    • 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
    • D06P1/667—Organo-phosphorus compounds
    • 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
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/24—Polyamides; Polyurethanes
    • 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
    • D06P5/20—Physical treatments affecting dyeing, e.g. ultrasonic or electric
    • D06P5/2044—Textile treatments at a pression higher than 1 atm
    • D06P5/2055—Textile treatments at a pression higher than 1 atm during dyeing
    • 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
    • D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/16—Synthetic fibres, other than mineral fibres
    • D06M2101/30—Synthetic polymers consisting of macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M2101/34—Polyamides
    • D06M2101/36—Aromatic polyamides

Definitions

  • This invention relates to dyeing aramid fibers and simultaneously improving the flame resistance of these fibers.
  • Aramids and aramid blends are dyed and optionally also flame-retardant-treated in conventional pressure dyeing equipment to produce an odor-free, colored, or colored and highly flame resistant, product.
  • Aramid fibers are highly resistant to heat decomposition, have inherent flame resistance, and are frequently used in working wear for special environments where flame resistance is required.
  • Meta-linked aromatic polyamide fibers are made from high-molecular-weight polymers that are highly crystalline and have either a high or no glass transition temperature.
  • aramid fibers also create difficulties for fiber processing in other areas; specifically, aramids are difficult to dye.
  • Fiber suppliers currently recommend a complicated exhaust dyeing procedure with a high carrier (acetophenone) content; the process is conducted at high temperatures over long periods of time and often results in a product having an unpleasant odor.
  • Such dyeing conditions require substantial amounts of energy both to maintain dyeing temperature and for the treatment of waste dye baths.
  • Polar organic solvents have also been used to swell the fiber or create voids in the fiber structure to enhance dyeability. These procedures involve solvent exhaust treatments at elevated temperatures with subsequent dyeing.
  • Another source of dyed aramid fiber is solution-dyed aramid yarn, available from the producer, prepared by solution dyeing in which a quantity of dye or pigment is mixed with the molten or dissolved polymer prior to extrusion of the polymer or solution into fine fibers; the dye or pigment becomes part of the fiber structure.
  • Solution-dyed fibers are more costly than the undyed fibers due, in part, to the additional costs of manufacture, and must be used in the color provided by the supplier, leaving the user with only a limited choice of colors.
  • Solution-dyed fibers offer relatively good lightfastness, whereas some undyed aramid fibers, particularly Nomex ® (DuPont), yellow following exposure to UV light. Because of this potential for yellowing, although deep, rich colorations, particularly dark blue and navy blue, are achievable, they still lack acceptable lightfastness. More recently, a process has been described in U.S. Patent No. 4,525,168 in which acid or anionic dyes are introduced into aramid fibers by coupling the dye to a dye site receptor which, in turn, is attached to the fiber. The process includes first swelling the fiber in a strong polar solvent and, while the fiber is in the swollen condition, introducing a substance capable of forming a strong chemical bond with an anionic dye into the swollen fiber..
  • This dye site receptor substance is an amine, typically hexamethylenediamine.
  • the procedure described requires at least three steps: first pretreating the fiber in a solution of solvent/swelling agent; treating with the diamine and a wetting agent; then drying to shrink the fiber and incorporate the diamine dye site receptor into the fiber. The thus-pretreated fabric is then dyed with an anionic dye.
  • Aramid fibers described and purported to be successfully dyed in U.S. 4,198,494 are sold under the trademarks Nomex® and Kevlar® by DuPont, and under the trademark Conex® by Teijin Limited of Tokyo, Japan.
  • a process has been used by Cates and others in U.S. Patent No. 4,759,770 for the continuous or semi-continuous dyeing of and simultaneous improving the flame-resistant properties of poly(m-phenyleneisophthalamide) fibers that includes the step of introducing the fiber into a fiber swelling agent solution also containing at least one dye together with at least one flame retardant, thereby swelling the fiber and introducing both the dye and the flame retardant into the fiber while in the swollen state.
  • the flame resistance/performance properties of fabrics dyed by this process are significant.
  • LOI values as described below, may be as high as 44% for simultaneously dyed and flame retarded T-455 Nomex fabric product produced by the process of this invention. As a means of comparison, undyed T-455 Nomex has an LOI of 27%. However, this process involves some equipment not routinely available on most existing processing lines.
  • the process includes the steps of introducing the fiber into a fiber dyeing solution containing a tinctorial amount of at least one dye together with N-cyclohexyl-2-pyrrolidone (CHP) as a diffusion promoter, and at least one flame retardant, especially chloroalkyl diphosphate esters such as Antiblaze 100, optionally also containing sodium nitrate, then heating the fiber and solution at a temperature and for a sufficient period of time to dye and flame retardant treat (when present) the fibers.
  • CHP N-cyclohexyl-2-pyrrolidone
  • N-cyclohexyl derivative of 2-pyrrolidone is the only dye diffusion agent effective for this process.
  • the N-methyl and N-ethyl analogs were tried, but they preformed poorly with respect to depth of dyeing and durability of the color to laundering, hence the described process is specific to the use of N-cyclohexyl-2-pyrrolidone.
  • Dyeing is always conducted above room temperature, conveniently in the range of about 120°C to about 150°C, at a pressure above atmospheric and for a time sufficient to achieve the desired coloration, usually from about 15 minutes up to 2 to 3 hours. Time and temperature are related, and we have found best results to be at about 130°C for a period of about one hour.
  • Flame retardants are applied in a range of about 3% to about 20% based on weight of fabric for the exemplified flame retardant Antiblaze 100, with a preferred range of from 6% to 15%, and a most preferred range of from 6% to 9%.
  • Both dyeing and flame retarding are affected by the concentration of cyclohexylpyrrolidone.
  • concentration of cyclohexylpyrrolidone As an illustration, we have obtained dye and FR fixation in this process using CHP concentrations of 25 to 120 percent on weight of fabric with best results at the 50 percent or higher level. Results are also affected by the liquor-to-fabric ratio. Typical liquor-to-fabric ratio for this work has been 15:1, although in production ratios as low as 5:1 may be used with 7:1 considered normal. Residual CHP is removed by heating with water at 130°C.
  • Fibers suitable for the process of this invention are known generally as aromatic polyamides.
  • This class includes a wide variety of polymers as disclosed in U.S. 4,324,706, the disclosure of which is incorporated by reference.
  • Our experience indicates that not all types of aromatic polyamide fibers can be reproducibly dyed by this process; some fibers are not affected sufficiently by the cyclohexylpyrrolidone to allow the dye to enter the fiber and are only surface stained, not fully dyed.
  • the fibers amenable to the process of this invention are made from a polymer known chemically as poly(m-phenyleneisophthalamide), i.e., the meta isomer which is the polycondensation product of metaphenylenediamine and isophthalic acid.
  • fiber name usually a trademark
  • producer is a listing of fibers now commercially available identified by fiber name (usually a trademark) and producer:
  • the preferred flame retardant is Antiblaze ® 100 ( Mobil Oi l Corp . ) CAS registry number 38051-10-4. It has the following structure :
  • Flame retardant concentrations in the treatment bath from 0.5% to about 20% (based on weight of fabric) are contemplated. However, the upper limit as a practical matter will be determined by the degree of performance required balanced against the cost of the FR chemical or system used. Concentrations in the range of about 3% to about 20% have been shown to be effective in increasing LOI values.
  • the phosphorus content of each sample was measured initially and after 25 launderings in hot water using a home washing machine and household laundry detergent.
  • Limiting Oxygen Index is a method of measuring the minimum oxygen concentration expressed as volume % needed to support candle-like combustion of a sample according to ASTM D-2863-77.
  • a test specimen is placed vertically in a glass cylinder, ignited, and a mixture of oxygen and nitrogen is flowed upwardly through the column.
  • An initial oxygen concentration is selected, the specimen ignited from the top and the length of burning and the time are noted.
  • the oxygen concentration is adjusted, the specimen is re-ignited (or a new specimen inserted), and the test is repeated until the lowest concentration of oxygen needed to support burning is reached.
  • Antiblaze-100 emulsion (30%) 50% the emulsion was then diluted to 200 gm
  • Antiblaze 100 enulsion (30%) 20% 40% 20% 40% 30%
  • Condition C is a useful treatment.
  • the effect of CHP is paramount, with little effect of AB100 level in this range. It appears that the 30% emulsion exhausts on the fabric very quickly and completely so that the effective concentration does not vary. However, penetration (and durability) vary as does the concentration of CHP as if AB100 acts as a colorless dye. The PBI content was stained rather than effectively dyed.
  • Nomex® was dyed/FR treated in the Ahiba unit already described, using Acid Dye #172 at 4%; Merpol HCS, 1%; acetic acid, 5%; all on weight of fabric.
  • Antiblaze 100 emulsion (30%) 20% 40% 20% 20% 30%

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Fireproofing Substances (AREA)
  • Treatments Of Macromolecular Shaped Articles (AREA)

Abstract

Des tissus d'aramides et de mélanges d'aramides sont teints et éventuellement soumis à un traitement retardateur de flamme au moyen d'équipements classiques de teinture sous pression et à chaud. On obtient des produits sans odeur, colorés ou bien colorés et extrêmement résistants à la flamme.
PCT/US1988/004074 1987-12-30 1988-11-15 Traitement tinctorial et retardateur de flamme simultane d'aramides WO1989006292A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
DE3889925T DE3889925D1 (de) 1987-12-30 1988-11-15 Gleichzeitige färbe- und flammhemmende behandlung von aramiden.
EP89900978A EP0400018B1 (fr) 1987-12-30 1988-11-15 Traitement tinctorial et retardateur de flamme simultane d'aramides
PCT/US1992/009728 WO1994011563A1 (fr) 1988-11-15 1992-11-17 Processus d'epuisement pour teindre des fibres aramides et/ou pour en ameliorer la resistance au feu
AU31328/93A AU3132893A (en) 1988-11-15 1992-11-17 Exhaust process for dyeing and/or improving the flame resistance of aramid fibers

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US13976187A 1987-12-30 1987-12-30
US139,761 1987-12-30
PCT/US1992/009728 WO1994011563A1 (fr) 1988-11-15 1992-11-17 Processus d'epuisement pour teindre des fibres aramides et/ou pour en ameliorer la resistance au feu
CA002149521A CA2149521C (fr) 1987-12-30 1992-11-17 Procede d'evacuation servant a teindre des fibres saramides ou a en ameliorer l'ininflammabilite

Publications (1)

Publication Number Publication Date
WO1989006292A1 true WO1989006292A1 (fr) 1989-07-13

Family

ID=27170017

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1988/004074 WO1989006292A1 (fr) 1987-12-30 1988-11-15 Traitement tinctorial et retardateur de flamme simultane d'aramides

Country Status (6)

Country Link
EP (1) EP0400018B1 (fr)
AT (1) ATE106475T1 (fr)
AU (1) AU2900189A (fr)
CA (1) CA2149521C (fr)
DE (1) DE3889925D1 (fr)
WO (1) WO1989006292A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4981488A (en) * 1989-08-16 1991-01-01 Burlington Industries, Inc. Nomex printing

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104695239B (zh) * 2015-04-07 2016-08-24 太仓卡斯特姆新材料有限公司 一种芳纶纤维的染色方法
WO2018220656A1 (fr) * 2017-06-02 2018-12-06 Arvind Limited Coloration oxydative de fibres thermoplastiques, et vêtement associé

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0246083A2 (fr) * 1986-05-14 1987-11-19 Burlington Industries, Inc. Procédé de teinture en continu ou en semi-continu d'une fibre de poly-(m-phénylène-isophtalamide)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4583986A (en) * 1981-07-20 1986-04-22 Combe Incorporated Catalyzed bismuth dye system for human hair

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0246083A2 (fr) * 1986-05-14 1987-11-19 Burlington Industries, Inc. Procédé de teinture en continu ou en semi-continu d'une fibre de poly-(m-phénylène-isophtalamide)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4981488A (en) * 1989-08-16 1991-01-01 Burlington Industries, Inc. Nomex printing

Also Published As

Publication number Publication date
CA2149521A1 (fr) 1994-05-26
ATE106475T1 (de) 1994-06-15
EP0400018A1 (fr) 1990-12-05
EP0400018B1 (fr) 1994-06-01
AU2900189A (en) 1989-08-01
CA2149521C (fr) 1999-07-20
DE3889925D1 (de) 1994-07-07

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