US3023071A - Process for the coloration of nylon type 11 fibres - Google Patents

Process for the coloration of nylon type 11 fibres Download PDF

Info

Publication number
US3023071A
US3023071A US840814A US84081459A US3023071A US 3023071 A US3023071 A US 3023071A US 840814 A US840814 A US 840814A US 84081459 A US84081459 A US 84081459A US 3023071 A US3023071 A US 3023071A
Authority
US
United States
Prior art keywords
parts
acid
naphthol
solution
fibres
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
US840814A
Inventor
Jirou Marcel
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.)
Compagnie Francaise des Matieres Colorantes SARL
Original Assignee
Compagnie Francaise des Matieres Colorantes SARL
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 Compagnie Francaise des Matieres Colorantes SARL filed Critical Compagnie Francaise des Matieres Colorantes SARL
Application granted granted Critical
Publication of US3023071A publication Critical patent/US3023071A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
    • C09B31/02—Disazo dyes
    • C09B31/12—Disazo dyes from other coupling components "C"
    • C09B31/14—Heterocyclic components
    • 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
    • Y10S8/924—Polyamide fiber

Definitions

  • the present invention is concerned with the colouration of fibres based on condensation products of w-aminoundecanoic acid such as Rilsan.
  • nylon obtained from the condensation of hexamethylenediamine with adipic acid, contains five methylene groups to one amido group, whereas Rilsan, resulting from the polymerisation of w-aminoundecanoic acid possesses 10 of them. Because this latter fibre has a longer polymethylene chain its paraflinic character is more marked, and it follows that it swells very little in water. For this reason and because of the low percentage of amido groups, its chemical inertia is greater and its tinctorial aflinity less than those of nylon, although the two fibres show certain analogies in their general properties. Thus the very great difiiculties met with in obtaining the depth of colour usually required on Rilsan fibres with the acid dyestuffs actually known are partly explained, the lack of uniformity in dyeing being common to all the polyamide fibres.
  • the exhaustion of the dyebaths can be improved by lowering the pH, by means of mineral acid which causes the activation of a larger number of groups of the fibre capable of combining with the anionic dyestuff, the complete elimination during drying of the mineral acid which is injurious to the fibre is very often diflicult.
  • the sought-for result would be obtained if, parallel to the exhaustion of the baths by lowering the pH, the diffusion of the dyestuffs towards the interior of the fibre could be realised.
  • the use of carriers for this purpose is often rejected by the users who consider it prejudicial to the good preservation of the properties of this fibre.
  • the object of the present invention is to. avoid these disadvantages by the colouration of fibres based on condensation products of w-aminoundecanoic acid of diazo dyestuffs of the following general formula:
  • R denotes a monosulphonated .l-aryl-S-pyrazolone having a methyl, carbonamido or carbonalkoxy group in the 3 position, and in which the aryl nucleus may also be substituted by halogen atoms or by nonsolubilising groups such as alkyl or alkoxy groups, or a naphtholmonosulphonic acid, or an acylamino-naphthol-monosulphonic acid, the acyl group being, for example, an a1kyl-CO-alkyl-OCO-, alkyl-SO or alkyl-O-CH CH OCO group.
  • the benzene rings A and B may be substituted by non-solubilising groups such as for example halogen atoms or alkyl, hydro-aryl, alkyl- 3,23,fi7l -Patented Feb. 27, 19%.?
  • Example 1 19.7 parts of amino-azobenzene are made into a paste in 210 parts of water and 46 parts of 30% hydrochloric acid. The next morning ice is added to lower the temperature of the mixture to 7 C., and a solution of 6.6 parts of sodium nitrite in its own weight of water is introduced over a period of 5 minutes. The mixture is stirred for 4 hours without exceeding the temperature of 10 C. The yellow diazo derivative is in solution.
  • the excess nitrous acid is destroyed by the addition of sulphamic acid, and the solution is introduced over 30 minutes into a bath prepared by dissolving 32 parts of 1-(2'-chloro-5'-suipho)-pl1enyl- 3-rnethyl-5-pyrazolone in 300 parts of water by means of 9 parts of sodium carbonate to which are added 38 parts of sodium carbonate.
  • the mixture is agitated for a further hour to finish the coupling, which is very rapid, the composition diluted to 2500 parts by volume is heated to C. and the dyestuff is precipitated by the addition of parts of desulphated sodium chloride.
  • the product is allowed to cool to 50 C. while stirring, and then filtered. After drying, the dyestufi is in the form of a yellow powder which dyes Rilsan from a slightly acid bath a yellowish orange shade having good fastness to wet tests and to light.
  • Example 2 19.7 parts of amino-azobenzene are diazotized by the process described in Example 1; the clear solution of the diazo derivative obtained is introduced over 30 minutes into a solution of 1-naphthol-4-sulphonic acid obtained by dissolving 25.8 parts of this acid in 350 parts of water, filtering and adding 38 parts of sodium carbonate. The mixture is stirred for a further half-hour to finish the coupling process, which is almost instantaneous, and is heated to 90 C., the dyestufl separated by filtration, and dried. The latter is in the form of a bluish red powder which dyes Rilsan from a slightly acid bath a bright red shade having good fastness to wet tests and characterised by an excellent fastness to light.
  • Example 3 22.5 parts of amino-azotoluene are made into a paste in 210 parts of water and 46 parts of a 30% solution of hydrochloric acid. The next morning, ice is added to the mixture to lower the temperature to 7 C., and a solution of 6.9 parts of sodium nitrite in its own weight of water is introduced over a period of five minutes. The mixture is agitated for four hours without exceeding a temperature of C.
  • the precipitated dyestuff is filtered off and dried, and is in the form of a yellow powder which dyes fibres consisting of a polycondensation product of w-aminoundecanoic acid from a slightly acid bath an orange shade more reddish than that of the dyestuif described in Example 1, and has good fastness to wet tests and to light.
  • Example 4 The solution of the diazo derivative of aminoazobenzene prepared according to Example 1 is introduced over minutes into a solution of 2-acetylamino-8- naphthol-6-sulphonic acid prepared by dissolving 29.5 parts of this acid in 400 parts of water by means of 8 parts of sodium carbonate, and adding 40 parts of sodium carbonate.
  • the bath is diluted with water to twice its volume, heated to 90 C., and the dyestuif separated by filtration is dried.
  • the powder obtained is a very bluish red and dyes Rilsan a ruby shade having good fastness to wet tests and a satisfactory fastness to light.
  • Example 5 22.5 parts of amino-azotoluene are diazotized according to the process described in Example 3; the diazo derivative obtained is introduced over a period of minutes into a solution of l-naphthol-4-sulphonic acid "prepared by dissolving 28.5 parts of this acid in 350 parts of water, filtering and adding 38 parts of sodium carbonate. The mixture is agitated for 30 minutes, heated to 90 C., and, after filtering, the dyestulf is dried. The latter dyes Rilsan a very bright bluish-red shade, having very good fastness to the various wet tests and an exceptionally good fastness to light.
  • Example 6 19.7 parts of amino-azobenzene are diazotized by the process described in Example 1 and the solution of the diazo derivative obtained is run over 15 minutes into a solution of 2-naphthol-8-sulphonic acid prepared by dis- Example 7
  • the 2-naphthol-8-sulphonic acid in the previous example is replaced by 1-acetylamino-8-naphthol-4-sulphonic acid.
  • a dyestutt is obtained which dyes Rilsan from a weakly acid bath a very bright redviolet.
  • Example 8 19.7 parts of amino-azobenzene are diazotized by the process described in Example 1 and the solution of the diazo derivative obtained is run over 20 minutes into a solution of Z-acetylamino-5-naphthol-7-sulphonic acid obtained by dissolving 30 parts of this acid in 400 parts of Water by means of sodium carbonate and adding 40 partsof sodium carbonate. The bath is agitated for an hour, with the addition of 150 parts of desulphated sodium chloride, then slowly heated to 40 C.
  • the dyestuif is separated by filtration, then dried. It dyes Rilsan from a slightly acid bath a bluish-red shade of good general fastness.
  • Example 9 22.5 parts of amino-azotoluene are diazotized by the process described in Example 3.
  • the solution of the diazo derivative obtained in introduced over 20 minutes into a solution of Z-acetylamino-S-naphthol-G-sulphonic acid prepared by dissolving 29.5 parts of this acid in 400 parts of water by means of 8 parts of sodium carbonate and adding 40 parts of sodium carbonate.
  • the mixture is agitated for an hour and the volume of the bath is doubled by the addition of the same quantity of water, heated to 95 C. and maintained at this temperature for an hour and a half, allowed to cool to C. and the precipitated dyestuff is separated by filtration.
  • the dark red powder obtained dyes Rilsan from a weakly acid bath a very bluish red shade having good general fastness.
  • Example 10 A dyebath is prepared in the proportion l/30 with 1% of formic acid and 0.5% of the dyestufi of Example in which R represents a member selected from the group consisting of the monosulphonated l-aryl-S-pyrazolones having a radical selected from the group consisting of the methyl, carbonamido and carbonalkoxy radicals in the 3 position, the naphthol monosulphonic acids and the W ean acylamino naphthol monosulphonic acids, the colouring agent being applied from a dyebath having a pH between 3 and 4. v

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Description

3,023,071 PROCESS FOR THE .COLORATION F NYLON TYPE 11 FEBRES Marcel Jiron, Sotteville-les-Rouen, France, assignor to Compagnie Francaise des Matieres Colorantes, Paris,
France, a company of France No Drawing. Filed Sept. 18, 1959, Ser. No. 840,814
Claims priority, application France Sept. 19, 1958 4 Claims. (Cl. 8-55) The present invention is concerned with the colouration of fibres based on condensation products of w-aminoundecanoic acid such as Rilsan.
It is known that nylon, obtained from the condensation of hexamethylenediamine with adipic acid, contains five methylene groups to one amido group, whereas Rilsan, resulting from the polymerisation of w-aminoundecanoic acid possesses 10 of them. Because this latter fibre has a longer polymethylene chain its paraflinic character is more marked, and it follows that it swells very little in water. For this reason and because of the low percentage of amido groups, its chemical inertia is greater and its tinctorial aflinity less than those of nylon, although the two fibres show certain analogies in their general properties. Thus the very great difiiculties met with in obtaining the depth of colour usually required on Rilsan fibres with the acid dyestuffs actually known are partly explained, the lack of uniformity in dyeing being common to all the polyamide fibres.
Although the exhaustion of the dyebaths can be improved by lowering the pH, by means of mineral acid which causes the activation of a larger number of groups of the fibre capable of combining with the anionic dyestuff, the complete elimination during drying of the mineral acid which is injurious to the fibre is very often diflicult. The sought-for result would be obtained if, parallel to the exhaustion of the baths by lowering the pH, the diffusion of the dyestuffs towards the interior of the fibre could be realised. The use of carriers for this purpose is often rejected by the users who consider it prejudicial to the good preservation of the properties of this fibre. As for the use of high temperatures for prolonged periods, this requires apparatus which is resistant to attack by the dyeing adjuvants, and all dyers do-not possess such apparatus. Only the increase in the plastosolubility of the molecule enables the diffusion of the dyestuif in the fibre to be increased to a certain extent and consequently the retention of a greater amount of dyestufi by the use of all the functions of the fibre which react with the anionic dyestuif.
The object of the present invention is to. avoid these disadvantages by the colouration of fibres based on condensation products of w-aminoundecanoic acid of diazo dyestuffs of the following general formula:
in which R denotes a monosulphonated .l-aryl-S-pyrazolone having a methyl, carbonamido or carbonalkoxy group in the 3 position, and in which the aryl nucleus may also be substituted by halogen atoms or by nonsolubilising groups such as alkyl or alkoxy groups, or a naphtholmonosulphonic acid, or an acylamino-naphthol-monosulphonic acid, the acyl group being, for example, an a1kyl-CO-alkyl-OCO-, alkyl-SO or alkyl-O-CH CH OCO group. The benzene rings A and B may be substituted by non-solubilising groups such as for example halogen atoms or alkyl, hydro-aryl, alkyl- 3,23,fi7l -Patented Feb. 27, 19%.?
wet tests and the fastness to light of some of them is excellent. The principle of the preparation of the dyestuffs of general Formula I is already known, but some of them, described below, are new.
The invention will be more clearly understood by reference to the following examples which are purely illustrative. The parts and percentages are by weight unless the contrary is indicated.
Example 1 19.7 parts of amino-azobenzene are made into a paste in 210 parts of water and 46 parts of 30% hydrochloric acid. The next morning ice is added to lower the temperature of the mixture to 7 C., and a solution of 6.6 parts of sodium nitrite in its own weight of water is introduced over a period of 5 minutes. The mixture is stirred for 4 hours without exceeding the temperature of 10 C. The yellow diazo derivative is in solution.
When coupling takes place, the excess nitrous acid is destroyed by the addition of sulphamic acid, and the solution is introduced over 30 minutes into a bath prepared by dissolving 32 parts of 1-(2'-chloro-5'-suipho)-pl1enyl- 3-rnethyl-5-pyrazolone in 300 parts of water by means of 9 parts of sodium carbonate to which are added 38 parts of sodium carbonate. The mixture is agitated for a further hour to finish the coupling, which is very rapid, the composition diluted to 2500 parts by volume is heated to C. and the dyestuff is precipitated by the addition of parts of desulphated sodium chloride. The product is allowed to cool to 50 C. while stirring, and then filtered. After drying, the dyestufi is in the form of a yellow powder which dyes Rilsan from a slightly acid bath a yellowish orange shade having good fastness to wet tests and to light.
On replacing the l-(2'-chloro-5-sulpho)-phenyl-3- methyl-S-pyrazolone with the corresponding quantity of 1 (2',5 dichloro-4'-sulpho)-phenyl-3-methyl-5-pyrazolone, a dyestuif is obtained which gives rather more reddish shades on Rilsan or nylon.
Much redder shades are obtained with the ethyl esters of l-(4-sulpho)-phenyl-5-pyrazolone 3 carboxylic acid and 1-(2'-chloro-5'-sulpho)-phenyl-5-pyrazolone 3 carboxylic acid.
Example 2 19.7 parts of amino-azobenzene are diazotized by the process described in Example 1; the clear solution of the diazo derivative obtained is introduced over 30 minutes into a solution of 1-naphthol-4-sulphonic acid obtained by dissolving 25.8 parts of this acid in 350 parts of water, filtering and adding 38 parts of sodium carbonate. The mixture is stirred for a further half-hour to finish the coupling process, which is almost instantaneous, and is heated to 90 C., the dyestufl separated by filtration, and dried. The latter is in the form of a bluish red powder which dyes Rilsan from a slightly acid bath a bright red shade having good fastness to wet tests and characterised by an excellent fastness to light.
The replacement of the 1-naphthol-4-sulphonic acid by l-naphthol-S-sulphonic acid gives a dyestufi which, under the same conditions, dyes Rilsan a much bluer shade, while the dyestuff obtained with 1-naphthol-6-sulphonic acid gives a brown shade.
Example 3 22.5 parts of amino-azotoluene are made into a paste in 210 parts of water and 46 parts of a 30% solution of hydrochloric acid. The next morning, ice is added to the mixture to lower the temperature to 7 C., and a solution of 6.9 parts of sodium nitrite in its own weight of water is introduced over a period of five minutes. The mixture is agitated for four hours without exceeding a temperature of C. When coupling occurs, the excess nitrous acid is destroyed by the addition of sulphamic acid and the solution of the diazo derivative is in troduced over 30 minutes into a coupling bath prepared by dissolving 32 parts of l-(2-chloro-5'-sulpho)-phenyl- 3-rnethyl-5-pyrazolone in 350 parts of water by means of 9 parts of sodium carbonate, to which are added 38 parts of sodium carbonate. The mixture is again agitated for an hour to finish the coupling, diluted to a volume of 2,700 parts, heated at 95 C. until completely dissolved, salted out with 60 parts of desulphated sodium chloride and allowed to cool to 45 C. while agitating. The precipitated dyestuff is filtered off and dried, and is in the form of a yellow powder which dyes fibres consisting of a polycondensation product of w-aminoundecanoic acid from a slightly acid bath an orange shade more reddish than that of the dyestuif described in Example 1, and has good fastness to wet tests and to light.
On replacing the 1-(2'-chloro-5'-sulpho)-phenyl-3- methyLS-pyrazolone by the corresponding quantity of l- (2',5 -dichloro-4-sulpho)-phenyl-3-methyl-S pyrazolone, a dyestuti is obtained which gives more reddish shades. With the ethyl ester of 1-(2-chloro-5'-sulpho)-phenyl-5- pyrazolone-B-carboxylic acid a pure reddish orange shade is obtained.
Example 4 The solution of the diazo derivative of aminoazobenzene prepared according to Example 1 is introduced over minutes into a solution of 2-acetylamino-8- naphthol-6-sulphonic acid prepared by dissolving 29.5 parts of this acid in 400 parts of water by means of 8 parts of sodium carbonate, and adding 40 parts of sodium carbonate. The bath is diluted with water to twice its volume, heated to 90 C., and the dyestuif separated by filtration is dried. The powder obtained is a very bluish red and dyes Rilsan a ruby shade having good fastness to wet tests and a satisfactory fastness to light.
The replacement of 2-acetylamino-S-naphthol-6-sulphonic acid by Z-ethoxycarbonylamino-8-naphthol6-sulphonic acid or 2-w-methoxy -ethoxycarbonylamino-8- naphthol-G-sulphonic acid leads to dyestuffs giving similar shades on Rilsan.
Example 5 22.5 parts of amino-azotoluene are diazotized according to the process described in Example 3; the diazo derivative obtained is introduced over a period of minutes into a solution of l-naphthol-4-sulphonic acid "prepared by dissolving 28.5 parts of this acid in 350 parts of water, filtering and adding 38 parts of sodium carbonate. The mixture is agitated for 30 minutes, heated to 90 C., and, after filtering, the dyestulf is dried. The latter dyes Rilsan a very bright bluish-red shade, having very good fastness to the various wet tests and an exceptionally good fastness to light.
Example 6 19.7 parts of amino-azobenzene are diazotized by the process described in Example 1 and the solution of the diazo derivative obtained is run over 15 minutes into a solution of 2-naphthol-8-sulphonic acid prepared by dis- Example 7 The 2-naphthol-8-sulphonic acid in the previous example is replaced by 1-acetylamino-8-naphthol-4-sulphonic acid. A dyestutt is obtained which dyes Rilsan from a weakly acid bath a very bright redviolet. 7 Example 8 19.7 parts of amino-azobenzene are diazotized by the process described in Example 1 and the solution of the diazo derivative obtained is run over 20 minutes into a solution of Z-acetylamino-5-naphthol-7-sulphonic acid obtained by dissolving 30 parts of this acid in 400 parts of Water by means of sodium carbonate and adding 40 partsof sodium carbonate. The bath is agitated for an hour, with the addition of 150 parts of desulphated sodium chloride, then slowly heated to 40 C.
- After an hours agitation at this temperature, the dyestuif is separated by filtration, then dried. It dyes Rilsan from a slightly acid bath a bluish-red shade of good general fastness.
The replacement of the Z-acetylamino-5-naphthol-7-sulphonic acid by 'Z-carboxy-acetylamino-5-naphthol-7-sulphonic acid leads to a dyestulf of a slightly more yellowish shade.
Example 9 22.5 parts of amino-azotoluene are diazotized by the process described in Example 3. The solution of the diazo derivative obtained in introduced over 20 minutes into a solution of Z-acetylamino-S-naphthol-G-sulphonic acid prepared by dissolving 29.5 parts of this acid in 400 parts of water by means of 8 parts of sodium carbonate and adding 40 parts of sodium carbonate. The mixture is agitated for an hour and the volume of the bath is doubled by the addition of the same quantity of water, heated to 95 C. and maintained at this temperature for an hour and a half, allowed to cool to C. and the precipitated dyestuff is separated by filtration.
After drying, the dark red powder obtained dyes Rilsan from a weakly acid bath a very bluish red shade having good general fastness.
Example 10 A dyebath is prepared in the proportion l/30 with 1% of formic acid and 0.5% of the dyestufi of Example in which R represents a member selected from the group consisting of the monosulphonated l-aryl-S-pyrazolones having a radical selected from the group consisting of the methyl, carbonamido and carbonalkoxy radicals in the 3 position, the naphthol monosulphonic acids and the W ean acylamino naphthol monosulphonic acids, the colouring agent being applied from a dyebath having a pH between 3 and 4. v
2. Process for the colouration of condensation products of w-arnino-undecanoic acid which comprises applying thereto, by dyeing in an acid medium and heating, a dyestufl of the general formula 3. Process as claimed in claim 2, in which the following dyestufr is used.
4. Process as claimed in claim 2, in which the following dyestnfi is used:
O H I l References Cited in the file of this patent Speel: Textile Chemicals and Auxiliaries, 2nd ed.,
1957, page 20.
Colour Index, 2nd ed, 1956, vol. 1, pp. 11161117, 1142, 1155, 1157; vol. 2, pp. 2078, 2102, 2145, 2158; vol. 3, pp. 3214, 3219, 3223, 3231, 3232, 3235.

Claims (1)

1. PROCESS FOR THE COLORATION OF CONDENSATION PRODUCTS OF W-AMINOUNDECANOIC ACID WHICH COMPRISES USING AS THE COLOURING AGENT A DYESTUFF OF THE GENERAL FORMULA:
US840814A 1958-09-19 1959-09-18 Process for the coloration of nylon type 11 fibres Expired - Lifetime US3023071A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR3023071X 1958-09-19

Publications (1)

Publication Number Publication Date
US3023071A true US3023071A (en) 1962-02-27

Family

ID=9691020

Family Applications (1)

Application Number Title Priority Date Filing Date
US840814A Expired - Lifetime US3023071A (en) 1958-09-19 1959-09-18 Process for the coloration of nylon type 11 fibres

Country Status (1)

Country Link
US (1) US3023071A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3324106A (en) * 1959-09-25 1967-06-06 Kuhlmann Ets 1-phenyl-5-pyrazolone-3-carbonamide disazo dyestuffs
US3958930A (en) * 1972-10-30 1976-05-25 E. I. Du Pont De Nemours & Company Deep-dyed nylon fiber and dyed styling yarn
US4019858A (en) * 1975-05-21 1977-04-26 American Cyanamid Company Concentrated direct dye solution and process therefor

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3324106A (en) * 1959-09-25 1967-06-06 Kuhlmann Ets 1-phenyl-5-pyrazolone-3-carbonamide disazo dyestuffs
US3958930A (en) * 1972-10-30 1976-05-25 E. I. Du Pont De Nemours & Company Deep-dyed nylon fiber and dyed styling yarn
US4019858A (en) * 1975-05-21 1977-04-26 American Cyanamid Company Concentrated direct dye solution and process therefor

Similar Documents

Publication Publication Date Title
US2782185A (en) Disazo dyestuffs
US3480378A (en) Process for dyeing linear polyester fiber materials
US2060186A (en) Dyeing of acetate artificial silk
US3206454A (en) Monoazo dyestuffs containing an aminosulfonyldialkylamino radical
US4234479A (en) Chromium mixed complex dyestuffs of phenyl-azo-pyrazole components
US3413075A (en) Azo dyestuff mixtures and aromatic polyester fibers colored therewith
US3532683A (en) Cationic mono azo dyes for anionic fibers
US2109552A (en) Azo dyestuffs and their metalliferous derivatives
US2576037A (en) Sulfonyl fluorides of amino azo dyestuffs
US3023071A (en) Process for the coloration of nylon type 11 fibres
US3272586A (en) Mixtures of phenyl sulfonamido-halobenzene azo amino-naphthol sulfonic acids
US2971953A (en) Water-insoluble azo-dyestuffs
US3687929A (en) Basic dyestuffs containing a quaternized pyridine or quinoline radical
US3829418A (en) Basic benzimidazoline arylhydrazone dyestuffs
US3632569A (en) Monazo dyestuffs containing a metaacylamino-para-amino aniline group
US1943170A (en) Azo-dyestuffs and process of making same
US4143035A (en) Disazo dyestuffs having an alkoxy group on the first and/or second component
US3066134A (en) Disazo-pyrazolone dyestuffs
US3549305A (en) Aromatic polyester fiber dyed with disazo dyestuff
US2027178A (en) Disazo dyestuffs and their production
US2177427A (en) Azo dyestuffs
US2140944A (en) Azo dyes
US3932379A (en) Water-soluble maroon and rubine sulphodiphenylazophenyl- or naphthylazoaniline dyes for polyamide fibers
US2727886A (en) Disazo dyestuffs
US4162249A (en) Anthranilic acid arylester-azo-aminonaphthol sulfonic acid dyes