US3577212A - Process for the modification of polyamide fibers - Google Patents
Process for the modification of polyamide fibers Download PDFInfo
- Publication number
- US3577212A US3577212A US658613A US3577212DA US3577212A US 3577212 A US3577212 A US 3577212A US 658613 A US658613 A US 658613A US 3577212D A US3577212D A US 3577212DA US 3577212 A US3577212 A US 3577212A
- Authority
- US
- United States
- Prior art keywords
- polyamide fibers
- bath
- fibers
- temperature
- parts
- 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
Links
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
- D06M13/322—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
- D06M13/402—Amides imides, sulfamic acids
- D06M13/438—Sulfonamides ; Sulfamic acids
-
- 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
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/12—Reserving parts of the material before dyeing or printing ; Locally decreasing dye affinity by chemical means
-
- 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
- D06P5/22—Effecting variation of dye affinity on textile material by chemical means that react with the fibre
Definitions
- the present invention relates to a process for the modification of synthetic polyamide fibers such as for example nylon, Rilsan or caprolactam polymers.
- polyamide fibers can be modified in an interesting way by treating them with solutions, suspensions or dispersions of non-colouring compounds, free from carboxylic and sulphonic groups, corresponding to the general formula:
- A represents a colourless aliphatic, aromatic or heterocyclic radical possibly carrying at least one nonauxochrome substituent such as for example chlorine or bromine atoms, or alkyl or alkoxy groups
- W represents the residue of an acylating agent carrying an atom or group of atoms capable of reacting with the polyamide fibers
- R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
- acylating agents which may be mentioned in which the residue W contains atoms or groups of atoms which permit reaction with the polyamide fibers, are halogenated triazines such as 2,4,6-trichloro s triazine, s-triazines of the general formula:
- A represents a colourless organic radical free from sulphonic and carboxylic groups
- halogenated pyrimidines such as for example 2,4,6-trichloro-pyrimidine, 2,4,5,6-tetrachloro-pyrimidine or the trichloropyrimidines substituted in the 5 position by a methyl, nitro or cyano group
- acid chlorides such as for example those of 2,4 dichloro-pyrimidine-G-carboxylic acid, 2,3-dichloroquinoxaline S-carboxylic acid, 2,3, dichloro-quinoxaline- 6 carboxylic acid, 1,4 dichloro-phthalazine 5 or 1,4- dichloro-phthalazine 6 carboxylic acid, ,B-chloropro pionic acid or acrylic acid.
- organic radicals A which are free from sulphonic and carboxylic groups are alkyl or aryl groups and the residues of primary or secondary amines.
- Sulphonamides of Formula II which may be used for the preparation of compounds of Formula I are: benzenesulphonamide, ortho-, meta-, and para-toluenesulphonamides, ortho-, meta-, and para-chlorobenzenesulphonamides, 1 methyl 4 chlorobenzene 2 sulphonamide, l methyl 5 chlorobenzene-Z-sulphonamide, 1-methyl- 6 chlorobenenze 2 sulphonamide, 1-methy1-2-chlorobenzene 3 sulphonamide, l-methyl-6-chlorobenzene-3- sulphonamide, 1 methyl 2 chlorobenzene-4-sulphonamide, 4 chlorobenzylsulphonamide, 2,4 dichlorobenzenesulphonamide, 2,5 dichlorobenzene sulphonamide, and 3,4-dichlorobenzene-sulphonamide.
- the treatment of the polyamide fibers is effected with a quantity of a compound of Formula I between 0.1% and 20%-of the weight of the material to be treated.
- a compound of Formula I When the compounds of Formula I are soluble in water, especially when R is a hydrogen atom they can be used in solution. If they are insoluble or not very soluble in water they can be used in the form of a fine dispersion.
- the compounds of Formula I can also be applied to the polyamide fibers in the form of printing pastes.
- the treatment of the polyamide fibers with the solutions or dispersions of the compounds of Formula I can be made in an acid, neutral or alkaline bath having a pH between 3 and 11 and at a temperature between 40 C. and the boiling temperature of the treatment bath.
- the treatment can be begun at a pH between 3 and 6 and finished at a value between 7 and .11.
- the treatment can also be effected directly at pH values between 7 and 11.
- the treatment can be prolonged in an alkaline bath charged with electrolytes at pH values between 7 and 11.
- the compounds with an acid reaction which may be used to modify the pH may be, for example, sulphuric, formic or acetic acid or their salts such as ammonium acetate or ammonium sulphate.
- the compounds having an alkaline reaction may be, for example, the alkali metal bicarbonates, carbonates or phosphates, borax, sodium acetate, ammonia or triethanolamine.
- Neutral salts which may be used are for example, sodium chloride or sodium sulphate.
- the polyamide fibers treated according to this invention have different properties from ordinary polyamide fibers, in particular, the affinity of acid dyestuffs for the treated fibers is considerably reduced and may even be rendered practically nil.
- EXAMPLE 1 10 parts of nylon thread are introduced at ambient temperature into a bath containing 200 parts of water, 1 part of the sodium salt of the condensate from one mole of paratoluene-sulphonamide with one mole of cyanuryl chloride prepared according to the process described in the Journal of the Chemical Society, 1963, page 4131, 0.5 part of crystalline ammonium acetate and 10 parts of anhydrous sodium sulphate.
- the temperature of the bath is brought to boiling in a period of 30 minutes, and this temperature is maintained for an hour.
- the temperature of the bath is then reduced to 95 C., and the pH is brought to 8 by the addition of dilute ammonia.
- the treatment is continued for 15 minutes.
- the nylon thread is then washed with soap and rinsed.
- the thread thus treated and an untreated thread are then dyed with the dyestulf known by the name of Rouge Ponceau Acide BL (Colour Index Acid Red 106.
- the dyestuff possesses very little affinity for the treated nylon, while the untreated thread is dyed a bright red.
- EXAMPLE 2 10 parts of nylon thread are introduced 'at ambient temperature into a bath containing 200 parts of water, 1 part of the sodium salt of the condensate from one mole of parachlorobenzene sulphonamide with one mole of cyanuryl chloride, 10 parts of sodium chloride and 0.2 part of sodium bicarbonate. The temperature of the bath is brought to boiling temperature in a period of 45 minutes and this temperature is maintained for one hour. The thread is washed with soap and rinsed. The behaviour of the treated nylon is comparable with that described in Example 1.
- EXAMPLE 3 10 parts of nylon thread are introduced into a bath at 40 C. containing 300 parts of water, 0.5 part of the monosodium salt of the condensate from one mole of paratoluene sulphonamide with one mole of the chloride of 2,3-dichloroquinoxaline-fi-carboxylic acid.
- the bath the pH of which is regulated at 5 by the addiiton of 1% acetic acid, is taken to boiling temperature in a period of 30 minutes and is maintained at this temperature for 30 minutes.
- the temperature of the bath is then reduced to 95 C. and the pH is brought to a value of 8 by the addition of disodium phosphate, and the treatment is followed for 15 minutes.
- the thread is washed with soap and rinsed. fIhe behaviour of the nylon towards acid dyestuffs is similar to that described in Example 1.
- EXAMPLE 4 A printed paste is prepared containing the following components:
- EXAMPLE 5 10 parts of nylon" thread are introduced into a bath at 40 C. containing 200 parts of water, 1 part of the sodium salt of the condensate from one mole of paratoluene sulphonamide with one mole of cyanuryl chloride, 20 parts of anhydrous sodium sulphate, 10 parts of 1% acetic acid and 10 parts of 10% sodium acetate. The temperature of the bath is brought to boiling in the course of 30 minutes and is maintained at this temperature for one hour. The nylon is then treated for an hour in a second bath at C. containing per litre 250 g. of sodium chloride and 65 g. of 2% ammonia, washed with soap and rinsed. The behaviour of the nylon towards acid dyestufls is similar to that described in Example 1.
- A represents the radical of a non-colouring compound of the aliphatic, aromatic or heterocyclic series free from carboxylic and sulphonic groups
- R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms
- W represents a halogenated triazinyl group, a halogenated pyrimidinyl group, the 2,4dichloro-pyrimidine-6-carbonyl group, the 2,3-dich1oroquinoxa1ine-5-carbonyl group, the 2,3-dichloro-quinoxaline-G-carbonyl group, the.1,4-dichloro-phthalazine-5-carbonyl group, the 1,4-dichloro-phthalazine-6-carbonyl group, the ,B-chloropropionyl group of the acryloyl group, the compound (I) being present in the amount of between 0.1% and 20% by weight of the polyamide fibres.
- Process for the modification of synthetic polyamide fibres which comprises applying thereto a printing paste containing a compound of the Formula I, in the amount of between 0.1% and 20% and steaming the printed fibres.
- DONALD LEVY Primary Examiner T. J. HERBERT, JR., Assistant Examiner U.S. Cl. X.R.
Abstract
IN WHICH A1 REPRESENTS A NON-COLOURING, ALIPHATIC, AROMATIC OR HETEROCYCLIC RADICAL, W REPRSENTS THE RESIDUE OF AN ACYLATING AGENT CARRYING AN ATOM OR GOUP OF ATOMS CAPABLE OF REACTING WITH THE POLYAMIDE FIBERS, AND R REPRESENTS A HYDROGEN ATOM OR AN ALKYL GROUP HAVING 1 TO 4 CARBON ATOMS, THE AMOUNT OF COMPOUND (I) USED BEING BETWEEN 0.1% AND 20% BY WEIGHT OF THE POLYAMIDE FIBERS. THE TREATED FIBERS HAVE DIFFERENT PROPERTIES FROM UNTREATED POLYAMIDE FIBERS AND IN PARTICULAR THEIR AFFINITY FOR ACID DYESTUFFS IS REDUCED OR RENDERED PRACTICALLY NIL.
A1-SO2-N(-R)-W
Description
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR72363 | 1966-08-08 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3577212A true US3577212A (en) | 1971-05-04 |
Family
ID=8615029
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US658613A Expired - Lifetime US3577212A (en) | 1966-08-08 | 1967-08-07 | Process for the modification of polyamide fibers |
Country Status (6)
Country | Link |
---|---|
US (1) | US3577212A (en) |
BE (1) | BE700508A (en) |
CH (2) | CH497597A (en) |
FR (1) | FR1495549A (en) |
GB (1) | GB1189726A (en) |
NL (2) | NL6709450A (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4780099A (en) * | 1986-08-26 | 1988-10-25 | E. I. Du Pont De Nemours And Company | Method for producing stain resistant polyamide fibers |
US5316850A (en) * | 1991-04-12 | 1994-05-31 | Peach State Labs, Inc. | Permanently stain resistant textile fibers |
US5629376A (en) * | 1990-10-31 | 1997-05-13 | Peach State Labs, Inc. | Polyacrylic acid compositions for textile processing |
US6524492B2 (en) | 2000-12-28 | 2003-02-25 | Peach State Labs, Inc. | Composition and method for increasing water and oil repellency of textiles and carpet |
JP2007503432A (en) * | 2003-08-27 | 2007-02-22 | アストラゼネカ・アクチエボラーグ | Novel fused N-pyrazinyl-sulfonamides and their use in the treatment of chemokine mediated diseases |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH880970A4 (en) * | 1970-06-11 | 1974-03-15 |
-
0
- NL NL135386D patent/NL135386C/xx active
- FR FR1495549D patent/FR1495549A/fr not_active Expired
-
1967
- 1967-06-26 BE BE700508D patent/BE700508A/xx unknown
- 1967-07-06 NL NL6709450A patent/NL6709450A/xx unknown
- 1967-07-07 CH CH980367A patent/CH497597A/en not_active IP Right Cessation
- 1967-07-07 CH CH980367D patent/CH980367A4/xx unknown
- 1967-08-04 GB GB35909/67A patent/GB1189726A/en not_active Expired
- 1967-08-07 US US658613A patent/US3577212A/en not_active Expired - Lifetime
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4780099A (en) * | 1986-08-26 | 1988-10-25 | E. I. Du Pont De Nemours And Company | Method for producing stain resistant polyamide fibers |
US5629376A (en) * | 1990-10-31 | 1997-05-13 | Peach State Labs, Inc. | Polyacrylic acid compositions for textile processing |
US5316850A (en) * | 1991-04-12 | 1994-05-31 | Peach State Labs, Inc. | Permanently stain resistant textile fibers |
US6524492B2 (en) | 2000-12-28 | 2003-02-25 | Peach State Labs, Inc. | Composition and method for increasing water and oil repellency of textiles and carpet |
JP2007503432A (en) * | 2003-08-27 | 2007-02-22 | アストラゼネカ・アクチエボラーグ | Novel fused N-pyrazinyl-sulfonamides and their use in the treatment of chemokine mediated diseases |
Also Published As
Publication number | Publication date |
---|---|
NL135386C (en) | |
BE700508A (en) | 1967-12-27 |
DE1619186A1 (en) | 1971-05-27 |
NL6709450A (en) | 1968-02-09 |
CH497597A (en) | 1970-06-30 |
FR1495549A (en) | 1967-12-20 |
CH980367A4 (en) | 1970-06-30 |
GB1189726A (en) | 1970-04-29 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: PRODUITS CHIMIQUES UGINE KUKLMANN TOUR MANHATTAN L Free format text: CHANGE OF NAME;ASSIGNOR:CHARLES DAVENPORT;REEL/FRAME:004245/0711 Effective date: 19831116 |
|
AS | Assignment |
Owner name: PECHINEY UGINE KUHLMANN Free format text: MERGER;ASSIGNOR:UGINE KUHLMANN;REEL/FRAME:004319/0671 Effective date: 19840820 Owner name: PRODUITS CHIMIQUES UGINE KUHLMANN Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:PECHINERY UGINE KUHLMANN;REEL/FRAME:004319/0683 Effective date: 19840820 |