[go: up one dir, main page]

US3674420A - Cycloalkanone or alkyl aryl ketone assisting cationic dye and aromatic polyamide dyeing therewith - Google Patents

Cycloalkanone or alkyl aryl ketone assisting cationic dye and aromatic polyamide dyeing therewith Download PDF

Info

Publication number
US3674420A
US3674420A US868566A US3674420DA US3674420A US 3674420 A US3674420 A US 3674420A US 868566 A US868566 A US 868566A US 3674420D A US3674420D A US 3674420DA US 3674420 A US3674420 A US 3674420A
Authority
US
United States
Prior art keywords
dye
bath
dyeing
aromatic polyamide
assistant
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
US868566A
Inventor
Ira Sapers
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.)
Sandoz Inc
Original Assignee
Arkansas Co 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 Arkansas Co Inc filed Critical Arkansas Co Inc
Application granted granted Critical
Publication of US3674420A publication Critical patent/US3674420A/en
Assigned to SANDOZ, INC. reassignment SANDOZ, INC. ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: ARKANSAS COMPANY, INC.
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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
    • 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
    • D06P3/242—Polyamides; Polyurethanes using basic dyes
    • 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
    • D06P1/65112—Compounds containing aldehyde or ketone groups
    • 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
    • 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
    • Y10S8/925—Aromatic polyamide

Definitions

  • the dye assistant comprises either a cyclic aliphatic ketone such as cyclohexanone or an aryl ketone such as acetophenone.
  • a method of dyeing such aromatic polyamide material which includes the dye assistant set forth hereinabove is also shown.
  • the method includes the steps of immersing the fiber in a dye bath including water, a surfactant, and the dye assistant of this invention and thence pressurizing the bath and raising the temperature thereof until the dyeing is completed.
  • This invention relates to dye assistants for aromatic polyamide fibrous material and to methods of dyeing such material.
  • aromatic polyamides consist, for example, of a condensation product of an aromatic diamine with an aromatic diacid halide.
  • condensation products are, for example, types 430 and 450 Nomex, made by E. I. du Pont de Nemours & Co. and other similar fibers.
  • Fibrous material of the above type makes excellent fabrics. These fabrics, contrary to other fabrics made of condensation-type polyamides such as type 6/6 nylon, melt at a very high temperature and even if brought to a temperature above their char point, will not propagate a flame.
  • fibrous material of this type has not yet become important in fabric manufacture. This is due to the fact that no proper method has heretofore been de veloped to dye such fibrous material. Obviously, undyed fibrous material of this type is completely unsatisfactory for making most articles of clothing and, what is even worse, some of the variations of aromatic polyamide fibrous material have a normally dirty brownish color.
  • aromatic polyamide fibrous material without the addition of dye-attracting groups, can become dyeable by the use of the specific types of dye assistants as set forth in this specification.
  • the use of these dye assistants will cause satisfactory dyeing to be produced with the use of conventional dyeing equipment.
  • the color fastness, light fastness, and other dye properties of the dyed material are fully comparable with the prop erties of conventional dyed material.
  • a dye assistant comprises either a cycloalkyl ketone, such as cyclohexanone or a phenyl alkyl ketone such as acetophenone.
  • the preferred proportion of the dye assistant to dye bath is five percent by weight. However, these percentages can be considerably reduced (to as ⁇ low as one percent, for example, when light shades are being dyed) and can range as high as fifteen percent by weight. Cationic dyes are preferred for use in this invention. The preferred percentage will depend upon the specific dye used. Naturally, for economic reasons, the smallest quantity of dye assistant that will be satisfactory for the purpose is used.
  • the surfactant used can be either a cationic surfactant, a nonionic plus an anionic surfactant, or a non-ionic plus a cationic surfactant.
  • An example of a cationic surfactant that can be employed is coconut trimethyl ammonium chloride
  • an example of an anionic surfactant that can be employed is a nonyl phenoxy ethanoxy ammonium sulfate.
  • nonionic surfactants that can be employed are nonyl phenol reacted with 30 mols of ethylene oxide and Pluronic P-68 which is a block copolymer of polypropylene oxide and ethylene oxide.
  • the molecular weight of polypropylene oxide is 1750 and the polyethylene oxide constitutes 80% of the weight of the copolymer. See Pat. No. 2,674,619 and The New Expanded Pluronic Acid and Typical Physical publication by the Wyndotte Chemical Companies.
  • the invention also includes the method of dyeing the aromatic polyamide fibrous material.
  • the method includes the steps of immersing the fibrous material in a dye bath which includes water, surfactant and the dye assistant of this invention, agitating the fibrous material in the bath until the materials are well distributed therein, and thence pressurizing and raising the temperature of the bath until the dyeing is completed.
  • acetophenone is one of the compounds set forth in the generalized formula of the dyeing assistant of this invention.
  • cyolohexanone is also a compound falling within this generalized formula. If a composition is made which includes these two components, there are far superior dyeing results produced than those produced with one of the elements alone. Furthermore, with the cyclohexanone-acetophenone combination, more even and level dyeing results, and excess dyeing assistant can be more easily washed out of the material.
  • compositions such as, for example, di-methyl sulfoxide, n-methyl 2 pyrrolidone, butyrolactone, n,n-di-methyl acetamide, and n,n-di-methy1 formamide.
  • swelling agents such as, for example, di-methyl sulfoxide, n-methyl 2 pyrrolidone, butyrolactone, n,n-di-methyl acetamide, and n,n-di-methy1 formamide.
  • the preferred proportions are fiftytwo percent (52%) acetophenone, forty-six percent (46%) cyclohexanone and two percent (2%) of the surfactant. These proportions can be varied to as low as twenty-five percent (25% by weight of acetophenone and seventy-five percent by weight of cyclohexanone, or alternatively, twenty-five percent (25%) by weight of cyclohexanone and seventy-five percent (75 by weight of acetophenone.
  • the surfactant percentages may range from one percent (1%) to five percent (5%) by weight.
  • swelling agents are included in the compositions, the range of percentages are from five (5%) percent to forty (40%) percent by Weight. Preferably swelling agents, where utilized, should amount to about twenty percent (20%) of the composition.
  • Example 1 A relatively heavy fabric composed of 100% of Type 430 Nomex fibrous material (manufactured by E. I. du Pont de Nemours & Co.) [weight 250 lbs] prescoured and de-sized, was placed within a dye bath at 100 the bath having a composition consisting of an intimate mixture of the following:
  • the dye bath was capable of being sealed hermetically but was open while the above treatment was being carried out.
  • the covers were then placed on the bath and the bath was sealed hermetically.
  • the bath was heated to a temperature of 270 F. and maintained at that temperature for approximately two hours.
  • the bath was then cooled to 190 F, the seals released slowly to depressurize the bath and the covers removed.
  • the bath was then overflowed with hot water at 150 F. and then dropped and the fabric was then rinsed with warm water at 110 F. for a period of about twenty minutes.
  • the fabric was then after-scoured, as follows:
  • An after-scouring bath was prepared at a temperature of 140 F. having the following ingredients:
  • Example II A relatively heavy fabric consisting entirely of Type 450 Nomex fibers (manufactured by E. I. du Pont de Nemours & Company) and which weighed about 250 pounds, was previously pre-scoured and de-sized and then placed within a dye bath having the following composition:
  • Example 1 The dyeing procedures used were the same as set forth in Example 1 and the dye used was also Astrazon Olive Green BL C.I. Basic Green 6. After dyeing the material was after-scoured using the same procedures as set forth in Example 1. An excellent dyeing was produced.
  • Example III A relatviely heavy fabric consisting entirely of Type 450 Nomex fibrous material previously pre-scoured (Manufactured by E. I. du Pont de Nemours & Company) [weight 250 lbs] was de-sized and placed within a dye bath maintained at a temperature of F. The bath had the following composition:
  • Astrazon Orange 3RL (a cationic dye manufactured by Verona Dyestuffs) and described in the Colour Index Second Edition 1956, Supplement 1963, published by The Society of Dyers and Colourists Dean House, Piccadilly, Bradford, Yorkshire, England, on page $156 as a Methine Dye, C.I. Basic Orange 27, was added to the bath and the fabric worked in the uncovered bath for an additional ten minutes. Thereafter, covers were placed on the bath and the bath sealed hermetically. The bath was then heated to a temperature of 250 and maintained at that temperature for approximately two and one-half hours. The bath was then cooled to 190 F., the seals released slowly to depressurize the bath and the covers removed.
  • the bath was then overflowed with hot water at 150 F. and the fabric then rinsed with warm water at F. for a period of about thirty minutes. Thereafter, the same after-scouring, spinning and drying proc ess as described in Example 1 were applied An excellent shade of orange was produced.
  • a dyeing composition comprising a cationic dye and a dye assistant, said composition being adapted for use in the dyeing of synthetic fibers made of aromatic polyamide material, said dye assistant being selected from the class consisting of cycle-alkyl ketones and phenyl alkyl ketones.
  • a dyeing composition comprising a cationic dye and a dye assistant, said composition being adapted for use in the dyeing of synthetic fibers made of aromatic polyamide material, said dye assistant being selected from the class consisting of acetophenone and cyclohexanone.
  • a dyeing composition comprising a cationic dye and a dye assistant, said composition being adapted for use in the dyeing of synthetic fibers made of aromatic polyarnide material, said dye assistant being composed of acetophenone.
  • a method of dyeing aromatic polyamide fibers comprising the steps of immersing said fibers in a bath consisting of water, a surfactant, a cationic dye and a dye assistant, said dye assistant consisting of a compound selected from the class consisting of cyclo-alkyl ketones and phenyl alkyl ketones, thence pressurizing said bath and raising the temperature thereof until the dyeing is completed.
  • a method of dyeing aromatic polyamide fibers comprising the steps of immersing said fibers in a bath consisting of Water, a surfactant, a cationic dye and a dye 6 assistant, said dye assistant consisting of a compound OTHER REFERENCES selected from the class consisting of acetophenone and cyclohexanone, thence pressurizing said bath and rais- 1963 coljumn 6511e' ing the temperature thereof until the dyeing is completed.
  • Shmldlen Preparatlon and 'Dyelng of Synthetic Flbres

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)

Abstract

A DYE ASSISTANT FOR AROMATIC POLYAMIDE FIBROUS MATERIAL IS SHOWN. THE DYE ASSISTANT COMPRISES WITHER A CYCLIC ALIPHATIC KETONE SUCH AS CYCLOHEXANONE OR AN ARYL KETONE SUCH AS ACETOPHENONE. A METHOD OF DYEING SUCH AROMATIC POLYAMIDE MATERIAL WHICH INCLUDES THE DYE ASSISTANT SET FORTH HEREINABOVE IS ALSO SHOWN. THE METHOD INCLUDES THE STEPS OF IMMERSING THE FIBER IN A DYE BATH INCLUDING WATER, A SURFACTANT, AND THE DYE ASSISTANT OF THE INVENTION AND THENCE PRESSURRIZING THE BATH AND RAISING THE TEMPERATURE THEREOF UNTIL THE DYEING IS COMPLETED.

Description

United States Patent 3,674,420 CYCLOALKANONE 0R ALKYL ARYL KETONE AS- SISTING CATIONIC DYE AND AROMATIC POLYAMIDE DYEING THEREWITH Ira Sapers, Maplewood, N.J., assignor to Arkansas Company, Inc., Newark, NJ. No Drawing. Filed Oct. 22, 1969, Ser. No. 868,566
Int. (:1. D06}: 5/04 U.S. c1. s-173 5 Claims ABSTRACT OF THE DISCLOSURE A dye assistant for aromatic polyamide fibrous material is shown. The dye assistant comprises either a cyclic aliphatic ketone such as cyclohexanone or an aryl ketone such as acetophenone.
A method of dyeing such aromatic polyamide material which includes the dye assistant set forth hereinabove is also shown. The method includes the steps of immersing the fiber in a dye bath including water, a surfactant, and the dye assistant of this invention and thence pressurizing the bath and raising the temperature thereof until the dyeing is completed.
DESCRIPTION OF THE INVENTION This invention relates to dye assistants for aromatic polyamide fibrous material and to methods of dyeing such material.
Recently aromatic polyamides have become an important synthetic fiber. These aromatic polyamides consist, for example, of a condensation product of an aromatic diamine with an aromatic diacid halide. Examples of such condensation products are, for example, types 430 and 450 Nomex, made by E. I. du Pont de Nemours & Co. and other similar fibers.
Fibrous material of the above type makes excellent fabrics. These fabrics, contrary to other fabrics made of condensation-type polyamides such as type 6/6 nylon, melt at a very high temperature and even if brought to a temperature above their char point, will not propagate a flame.
Unfortunately fibrous material of this type has not yet become important in fabric manufacture. This is due to the fact that no proper method has heretofore been de veloped to dye such fibrous material. Obviously, undyed fibrous material of this type is completely unsatisfactory for making most articles of clothing and, what is even worse, some of the variations of aromatic polyamide fibrous material have a normally dirty brownish color.
It has been heretofore proposed to make such fibrous material dyeable by adding a dye-attracting group to the structure of the material such as, for example, a sulfonic acid radical or the like. Unfortunately, while the addition of such a group will cause the fibrous material to become dyeable, the strength of the fiber becomes so seriously reduced as to make it unsatisfactory for use in wearing apparel.
I have discovered that aromatic polyamide fibrous material, without the addition of dye-attracting groups, can become dyeable by the use of the specific types of dye assistants as set forth in this specification. The use of these dye assistants will cause satisfactory dyeing to be produced with the use of conventional dyeing equipment. The color fastness, light fastness, and other dye properties of the dyed material are fully comparable with the prop erties of conventional dyed material.
A dye assistant comprises either a cycloalkyl ketone, such as cyclohexanone or a phenyl alkyl ketone such as acetophenone.
3,674,420 Patented July 4, 1972 "Ice The preferred proportion of the dye assistant to dye bath is five percent by weight. However, these percentages can be considerably reduced (to as \low as one percent, for example, when light shades are being dyed) and can range as high as fifteen percent by weight. Cationic dyes are preferred for use in this invention. The preferred percentage will depend upon the specific dye used. Naturally, for economic reasons, the smallest quantity of dye assistant that will be satisfactory for the purpose is used.
In order to improve the levelling of the dye upon the fibrous material, it is also desirable to use a surfactant. The surfactant used can be either a cationic surfactant, a nonionic plus an anionic surfactant, or a non-ionic plus a cationic surfactant. An example of a cationic surfactant that can be employed is coconut trimethyl ammonium chloride, an example of an anionic surfactant that can be employed is a nonyl phenoxy ethanoxy ammonium sulfate. Examples of nonionic surfactants that can be employed are nonyl phenol reacted with 30 mols of ethylene oxide and Pluronic P-68 which is a block copolymer of polypropylene oxide and ethylene oxide. The molecular weight of polypropylene oxide is 1750 and the polyethylene oxide constitutes 80% of the weight of the copolymer. See Pat. No. 2,674,619 and The New Expanded Pluronic Acid and Typical Physical publication by the Wyndotte Chemical Companies.
The invention also includes the method of dyeing the aromatic polyamide fibrous material. The method includes the steps of immersing the fibrous material in a dye bath which includes water, surfactant and the dye assistant of this invention, agitating the fibrous material in the bath until the materials are well distributed therein, and thence pressurizing and raising the temperature of the bath until the dyeing is completed.
There are further surprising results that are accomplished by the addition of other components to the dyeing assistant system of this invention.
For example, acetophenone is one of the compounds set forth in the generalized formula of the dyeing assistant of this invention. Likewise, cyolohexanone is also a compound falling within this generalized formula. If a composition is made which includes these two components, there are far superior dyeing results produced than those produced with one of the elements alone. Furthermore, with the cyclohexanone-acetophenone combination, more even and level dyeing results, and excess dyeing assistant can be more easily washed out of the material.
Even better results are accomplished by the addition of swelling agents to the compositions, such as, for example, di-methyl sulfoxide, n-methyl 2 pyrrolidone, butyrolactone, n,n-di-methyl acetamide, and n,n-di-methy1 formamide.
In the specific composition of acetophenone, cyclohexanone and surfactants, the preferred proportions are fiftytwo percent (52%) acetophenone, forty-six percent (46%) cyclohexanone and two percent (2%) of the surfactant. These proportions can be varied to as low as twenty-five percent (25% by weight of acetophenone and seventy-five percent by weight of cyclohexanone, or alternatively, twenty-five percent (25%) by weight of cyclohexanone and seventy-five percent (75 by weight of acetophenone. The surfactant percentages may range from one percent (1%) to five percent (5%) by weight.
Where swelling agents are included in the compositions, the range of percentages are from five (5%) percent to forty (40%) percent by Weight. Preferably swelling agents, where utilized, should amount to about twenty percent (20%) of the composition.
The invention will now be further described by specific examples of the practice thereof.
Example 1 A relatively heavy fabric composed of 100% of Type 430 Nomex fibrous material (manufactured by E. I. du Pont de Nemours & Co.) [weight 250 lbs] prescoured and de-sized, was placed within a dye bath at 100 the bath having a composition consisting of an intimate mixture of the following:
Lbs.
Water 5000 Acetic acid (56%) 2.5 Salt ('NaCl) 5D Acetophenone 244 Pluronic F-68 6 The material was worked in the bath for a period of five to ten minutes. Thereafter 10 lbs. of pre-dissolved Astrazon Olive Green BL (a cationic dye manufactured by Verona Dyestuffs) and described on page S176 of the Colour Index Second Edition 1956, Supplement 1963, published by The Society of Dyers and Colourists Dean House, Piccadilly, Bradford, Yorkshire, England, as a Quinoline Dye, C.I. Basic Green 6, was added to the bath and the fabric worked in the bath for an additional five to ten minutes. The dyeing equipment used was conventional pressure dyeing equipment. The dye bath was capable of being sealed hermetically but was open while the above treatment was being carried out. The covers were then placed on the bath and the bath was sealed hermetically. The bath was heated to a temperature of 270 F. and maintained at that temperature for approximately two hours. The bath was then cooled to 190 F, the seals released slowly to depressurize the bath and the covers removed. The bath was then overflowed with hot water at 150 F. and then dropped and the fabric was then rinsed with warm water at 110 F. for a period of about twenty minutes. The fabric was then after-scoured, as follows:
An after-scouring bath was prepared at a temperature of 140 F. having the following ingredients:
Lbs.
Water 5000 A non-ionic surfactant consisting of nonyl-phenol reacted with 30 mols of ethylene oxide 2 /2 Tetra sodium pyrophosphate 5 The above bath was heated to 180 F. and the fabric was run in the bath from twenty to thirty minutes. The bath was then overflowed and dropped and the fabric rinsed with warm water at 110 F. for fifteen minutes. The fabric was then rinsed with water at room temperature (80 F.) for an additional fifteen minutes. The wet fabric was then spun to remove the excess water and was then dried. An excellent color fast dye was produced.
Example II A relatively heavy fabric consisting entirely of Type 450 Nomex fibers (manufactured by E. I. du Pont de Nemours & Company) and which weighed about 250 pounds, was previously pre-scoured and de-sized and then placed within a dye bath having the following composition:
. Lbs. Water 5000 Acetic acid (56%) 2 /2 Salt (NaCl) 100 Pluronic F-68 5 Cyclohexanone 185.6 Acetophenone 62.5
The dyeing procedures used were the same as set forth in Example 1 and the dye used was also Astrazon Olive Green BL C.I. Basic Green 6. After dyeing the material was after-scoured using the same procedures as set forth in Example 1. An excellent dyeing was produced.
Example III A relatviely heavy fabric consisting entirely of Type 450 Nomex fibrous material previously pre-scoured (Manufactured by E. I. du Pont de Nemours & Company) [weight 250 lbs] was de-sized and placed within a dye bath maintained at a temperature of F. The bath had the following composition:
Lbs.
Water 5000 Acetic acid (56%) 2 /2 Salt (NaCl) n-Methyl-Z-pyrrolidone 22.5 di-methyl sulfoxide 22.5 Acetophenone 1 75 Cyclohexanone 25 Pluronic F-68 5 The bath was maintained within conventional pressure dyeing equipment. The components of the bath were thoroughly mixed with the bath uncovered. The material was worked in the bath for a period of five to ten minutes. Thereafter ten pounds of .pre-dissolved Astrazon Orange 3RL (a cationic dye manufactured by Verona Dyestuffs) and described in the Colour Index Second Edition 1956, Supplement 1963, published by The Society of Dyers and Colourists Dean House, Piccadilly, Bradford, Yorkshire, England, on page $156 as a Methine Dye, C.I. Basic Orange 27, was added to the bath and the fabric worked in the uncovered bath for an additional ten minutes. Thereafter, covers were placed on the bath and the bath sealed hermetically. The bath was then heated to a temperature of 250 and maintained at that temperature for approximately two and one-half hours. The bath was then cooled to 190 F., the seals released slowly to depressurize the bath and the covers removed. The bath was then overflowed with hot water at 150 F. and the fabric then rinsed with warm water at F. for a period of about thirty minutes. Thereafter, the same after-scouring, spinning and drying proc ess as described in Example 1 were applied An excellent shade of orange was produced.
The foregoing sets forth the manner in which the objects of this invention are achieved.
I claim:
1. A dyeing composition comprising a cationic dye and a dye assistant, said composition being adapted for use in the dyeing of synthetic fibers made of aromatic polyamide material, said dye assistant being selected from the class consisting of cycle-alkyl ketones and phenyl alkyl ketones.
2. A dyeing composition comprising a cationic dye and a dye assistant, said composition being adapted for use in the dyeing of synthetic fibers made of aromatic polyamide material, said dye assistant being selected from the class consisting of acetophenone and cyclohexanone.
3. A dyeing composition comprising a cationic dye and a dye assistant, said composition being adapted for use in the dyeing of synthetic fibers made of aromatic polyarnide material, said dye assistant being composed of acetophenone.
4. A method of dyeing aromatic polyamide fibers comprising the steps of immersing said fibers in a bath consisting of water, a surfactant, a cationic dye and a dye assistant, said dye assistant consisting of a compound selected from the class consisting of cyclo-alkyl ketones and phenyl alkyl ketones, thence pressurizing said bath and raising the temperature thereof until the dyeing is completed.
5. A method of dyeing aromatic polyamide fibers comprising the steps of immersing said fibers in a bath consisting of Water, a surfactant, a cationic dye and a dye 6 assistant, said dye assistant consisting of a compound OTHER REFERENCES selected from the class consisting of acetophenone and cyclohexanone, thence pressurizing said bath and rais- 1963 coljumn 6511e' ing the temperature thereof until the dyeing is completed. Shmldlen: Preparatlon and 'Dyelng of Synthetic Flbres,
5 pp. 150-157. References Cited UNITED STATES PATENTS DONALD LEVY, Primary Examiner 3,184,436 5/1965 Magat 260-78 3,232,910 2/1966 Preston 260-78 3,506,990 4/1970 Richardson 8-172 10 s 172
US868566A 1969-10-22 1969-10-22 Cycloalkanone or alkyl aryl ketone assisting cationic dye and aromatic polyamide dyeing therewith Expired - Lifetime US3674420A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US86856669A 1969-10-22 1969-10-22

Publications (1)

Publication Number Publication Date
US3674420A true US3674420A (en) 1972-07-04

Family

ID=25351931

Family Applications (1)

Application Number Title Priority Date Filing Date
US868566A Expired - Lifetime US3674420A (en) 1969-10-22 1969-10-22 Cycloalkanone or alkyl aryl ketone assisting cationic dye and aromatic polyamide dyeing therewith

Country Status (1)

Country Link
US (1) US3674420A (en)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3771949A (en) * 1971-11-29 1973-11-13 Martin Processing Co Inc Pretreatment and dyeing of shaped articles derived from wholly aromatic polyamides
USB348383I5 (en) * 1969-09-03 1975-01-28
US3967925A (en) * 1974-09-19 1976-07-06 The Carborundum Company Cationic dyeing of novoloid fibers
US4066395A (en) * 1974-12-02 1978-01-03 Ciba-Geigy Corporation Process for dyeing or printing aromatic polyamide fibres
US4144023A (en) * 1977-10-11 1979-03-13 E. I. Du Pont De Nemours And Company Dyeing of high strength, high modules aromatic polyamide fibers
JPS57167466A (en) * 1981-04-03 1982-10-15 Teijin Ltd Dyeing of aromatic polyamide fiber
US4780105A (en) * 1987-04-15 1988-10-25 Stockhausen, Inc. Composition for dyeing material of synthetic aromatic polyamide fibers: cationic dye and n-alkyl phthalimide
US5096459A (en) * 1990-09-26 1992-03-17 E. I. Du Pont De Nemours And Company Method of dyeing aromatic polyamide fibers with water-soluble dyes
US5298201A (en) * 1990-12-21 1994-03-29 Milliken Research Corporation Method for improving dyeability of fiber and associated fabric utilizing radiation
US5404625A (en) * 1990-10-12 1995-04-11 Milliken Research Corporation Method and apparatus for modifying fibers and fabric by impaction with particles
US6551362B2 (en) 2001-02-02 2003-04-22 Bgb Stockhausen Gmbh Composition for dyeing material of synthetic aromatic polyamide fibers comprising a cationic dye and novel dye assistant
EP3336147A1 (en) 2016-12-15 2018-06-20 DyStar Colours Distribution GmbH Basic dye mixtures for aramid fibres
WO2020262671A1 (en) 2019-06-28 2020-12-30 帝人株式会社 Dyed fabric, fiber product in which same is used, and method for dyeing fabric

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USB348383I5 (en) * 1969-09-03 1975-01-28
US3923452A (en) * 1969-09-03 1975-12-02 Ciba Geigy Ag Amine salt of a dyestuff in a ketone solution
US3771949A (en) * 1971-11-29 1973-11-13 Martin Processing Co Inc Pretreatment and dyeing of shaped articles derived from wholly aromatic polyamides
US3967925A (en) * 1974-09-19 1976-07-06 The Carborundum Company Cationic dyeing of novoloid fibers
US4066395A (en) * 1974-12-02 1978-01-03 Ciba-Geigy Corporation Process for dyeing or printing aromatic polyamide fibres
US4144023A (en) * 1977-10-11 1979-03-13 E. I. Du Pont De Nemours And Company Dyeing of high strength, high modules aromatic polyamide fibers
FR2406021A1 (en) * 1977-10-11 1979-05-11 Du Pont HIGH STRENGTH AND HIGH MODULE AROMATIC POLYAMIDE FIBER DYE
JPS57167466A (en) * 1981-04-03 1982-10-15 Teijin Ltd Dyeing of aromatic polyamide fiber
US4780105A (en) * 1987-04-15 1988-10-25 Stockhausen, Inc. Composition for dyeing material of synthetic aromatic polyamide fibers: cationic dye and n-alkyl phthalimide
US5096459A (en) * 1990-09-26 1992-03-17 E. I. Du Pont De Nemours And Company Method of dyeing aromatic polyamide fibers with water-soluble dyes
US5404625A (en) * 1990-10-12 1995-04-11 Milliken Research Corporation Method and apparatus for modifying fibers and fabric by impaction with particles
US5298201A (en) * 1990-12-21 1994-03-29 Milliken Research Corporation Method for improving dyeability of fiber and associated fabric utilizing radiation
US6551362B2 (en) 2001-02-02 2003-04-22 Bgb Stockhausen Gmbh Composition for dyeing material of synthetic aromatic polyamide fibers comprising a cationic dye and novel dye assistant
EP3336147A1 (en) 2016-12-15 2018-06-20 DyStar Colours Distribution GmbH Basic dye mixtures for aramid fibres
WO2018108682A1 (en) 2016-12-15 2018-06-21 Dystar Colours Distribution Gmbh Basic dye mixtures for aramid fibres
US11377787B2 (en) 2016-12-15 2022-07-05 Dystar Colours Distribution Gmbh Basic dye mixtures for aramid fibres
WO2020262671A1 (en) 2019-06-28 2020-12-30 帝人株式会社 Dyed fabric, fiber product in which same is used, and method for dyeing fabric

Similar Documents

Publication Publication Date Title
US3674420A (en) Cycloalkanone or alkyl aryl ketone assisting cationic dye and aromatic polyamide dyeing therewith
US3771949A (en) Pretreatment and dyeing of shaped articles derived from wholly aromatic polyamides
US2317965A (en) Process of coloring fibrous materials and the materials obtained thereby
EP0613976B1 (en) Use of acryl amide polymers as anti-crease
US3630662A (en) Process of dyeing shaped condensation polymer material in heated two-phase dye liquid
DE2553543A1 (en) METHOD OF DYING AROMATIC POLYAMIDE FIBERS
US3775045A (en) Process for the production of multi-colour effects on natural and synthetic polyamide fibre material
US3454512A (en) Dyeable compositions comprising polypropylene,polyamide and ethylene copolymer
JPH0645763B2 (en) Mixture of dispersed azo dyes
US2884332A (en) Printing of textile materials and preparations therefor
US3148934A (en) Process for dyeing polyester articles
US2959461A (en) Fugitive tints for natural and synthetic fibers
US2952506A (en) Process for even and level dyeing of filament nylon fabrics
US3824076A (en) Liquid ammonia-caustic dye solution and dyeing therewith
CN111253776A (en) Dark blue reactive dye formula for all-cotton and all-cotton blended fabric and application
JP2014084329A (en) Acid dye composition and dyeing method using the same
US3652199A (en) Process for drying polyamide fibers catonic dyes and zinc thiocyanate
US3281201A (en) Process for dyeing of nylon fibers with premetallized and acid dyestuffs
US3236582A (en) Process of dyeing polyurethane shaped article with water-soluble reactive dyestuffs
JPH0665789B2 (en) Dyeing method of polyester / cellulose composite fiber
EP0250365A1 (en) Process for the after-treatment of dyed cellulosic fibrous material
DE1769613A1 (en) Agent for improving the wet fastness properties of dyes produced with cationic dyes on synthetic polyamides
US3330893A (en) Method for increasing the dyeability of filamentary material
US2931698A (en) Reserving agent for acrylonitrile polymer base fibers
US3700405A (en) Dyeing of polycarbonamides of bis(paraamino-cyclohexyl)methane and dodecanediodic acid with anionic dyes

Legal Events

Date Code Title Description
AS Assignment

Owner name: SANDOZ, INC., 59 ROUTE 10, EAST HANOVER, NJ 07936

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST. EFFECTIVE DATE;ASSIGNOR:ARKANSAS COMPANY, INC.;REEL/FRAME:004209/0628

Effective date: 19840104