US3854872A - Process for dyeing of polyacrylonitrile fibers - Google Patents
Process for dyeing of polyacrylonitrile fibers Download PDFInfo
- Publication number
- US3854872A US3854872A US00345850A US34585073A US3854872A US 3854872 A US3854872 A US 3854872A US 00345850 A US00345850 A US 00345850A US 34585073 A US34585073 A US 34585073A US 3854872 A US3854872 A US 3854872A
- Authority
- US
- United States
- Prior art keywords
- dyeing
- bath
- polyamino amide
- dye
- quaternized
- 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
- 229920002239 polyacrylonitrile Polymers 0.000 title claims abstract description 22
- 238000004043 dyeing Methods 0.000 title claims abstract description 21
- 238000000034 method Methods 0.000 title claims abstract description 10
- 239000000835 fiber Substances 0.000 title abstract description 15
- 150000001408 amides Chemical class 0.000 claims abstract description 19
- 125000002091 cationic group Chemical group 0.000 claims abstract description 13
- 238000009833 condensation Methods 0.000 claims abstract description 8
- 230000005494 condensation Effects 0.000 claims abstract description 8
- 239000004593 Epoxy Substances 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 230000000979 retarding effect Effects 0.000 claims abstract description 6
- 229920000768 polyamine Polymers 0.000 claims abstract description 5
- 239000000975 dye Substances 0.000 claims description 30
- 239000004744 fabric Substances 0.000 claims description 17
- 239000000463 material Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- -1 HYDROGEN ATOMS Chemical group 0.000 claims description 4
- 239000003086 colorant Substances 0.000 claims description 4
- 239000004952 Polyamide Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229920002647 polyamide Polymers 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract description 3
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 238000005956 quaternization reaction Methods 0.000 abstract description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 229920006122 polyamide resin Polymers 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000003340 retarding agent Substances 0.000 description 2
- 229960001124 trientine Drugs 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- WVUKFQBBZVBJRZ-UHFFFAOYSA-N 4-[(6-methoxy-3-methyl-1,3-benzothiazol-3-ium-2-yl)diazenyl]-n,n-dimethylaniline Chemical compound S1C2=CC(OC)=CC=C2[N+](C)=C1N=NC1=CC=C(N(C)C)C=C1 WVUKFQBBZVBJRZ-UHFFFAOYSA-N 0.000 description 1
- LSSUMOWDTKZHHT-UHFFFAOYSA-N N,n-diethyltryptamine Chemical compound C1=CC=C2C(CCN(CC)CC)=CNC2=C1 LSSUMOWDTKZHHT-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/52—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 synthetic macromolecular substances
- D06P1/5264—Macromolecular compounds obtained otherwise than by reactions involving only unsaturated carbon-to-carbon bonds
- D06P1/5278—Polyamides; Polyimides; Polylactames; Polyalkyleneimines
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/655—Compounds containing ammonium groups
- D06P1/66—Compounds containing ammonium groups containing quaternary ammonium groups
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
- D06P3/70—Material containing nitrile groups
- D06P3/76—Material containing nitrile groups using basic dyes
Definitions
- polyacrylonitrile fibers are dyed in general utilizing cationic dyes such as those for example of the series of triaryl methane, oxazine, etc.
- the application of cationic dyes onto the polyacrylonitrile fibers can be accomplished by different dyeing processes.
- the bath dyeing that is by exhausting dye baths, the taking up and the fixation of the dye into the fiber can be correctly obtained only at temperatures less than those in the vicinity of the boiling point of water.
- the present invention more particularly relates to the use of new retarding agents in the dye baths with the cationic dyes.
- FORMULA I in which R, R and R' are alkyl radicals, identical or FORMULA ll H N- R-Nm H in which at is at least equal to one;
- R is an alkylene radical having one to five carbon atoms, such as ethylene, propylene, butylene, etc.
- polyamines should in addition contain at least four atoms of reactive hydrogenper molecule as, for example, ethylene diamine (E.D.A. diethylene triamine (D.E.T.A.), triethylene tetramine (T.E.T.A.), etc.
- E.D.A. diethylene triamine (D.E.T.A.) diethylene triamine (D.E.T.A.)
- T.E.T.A. triethylene tetramine
- composition of the quatemized polyamino amide compounds which are known and used according to the present invention can be schematically represented by the following generic formula:
- a sample of polyacrylonitrile fabric was introduced into an-aqueous solution at 60C containing 0.5% of blue dye, C.l. (Color Index) basic blue 54, 4% of acetic acid (40%) and 0.5% of quatemized polyamino amide, the percentages given being calculated with respect to the weight of the fiber to be dyed.
- the proportion of dyeing bath was from one to twenty (that is, 20 ml of bath per i g. of material to be dyed).
- the temperature was brought in 30 minutes to 100C, then the dyeing was maintained at this temperature for an hour. After-this period, the bath was practically exhausted.
- the sample wasthen subjected to a rinsing and then a drying.
- the polyamino amide utilized in the example was obi tained' by condensation of a fatty diacid (EMPOL 1024) with ethylene diamine, followed by quatemization by the .chloride of epoxypropyltrimethyl ammonium.
- EXAMPLE 2 A sample of polyacrylonitrile fabric .was' introduced amide, the percentages being calculated with respect to A the weight of the fabric. The proportion of the bath was 1 to 20.
- the polyamino amide utilized was identical to that used in Example 1.
- the polyamino amide was obtained by condensation of a fatty acid (EMPOL 1024 with diethylene triamine, then. quatemized by the chloride of epoxypropyl trimethyl ammonium.
- EXAMPLE 4 A sample of polyacrylonitrile fabric was dyed utilizing the dye and under the identical conditions as in Example l.
- the polyamino amide utilized was obtained by condensation of a fatty acid (EMPOL 1024) with triethylene tetramine, followed by quatemization by the chloride of epoxypropyl trimethyl ammonium.
- the blue sample, of fabric was introducedsimultaneously with a white sample of the same material of the same weight into an aqueous bath free of dye containing 4% of acetic acid (40%),
- a process for dyeing polyacrylonitrile fabrics in an aqueous bath containing a cationic colorant comprising adding to the bath as a retarding and equalization of dyeing agent, a quatemized polyamino amide obtained by the condensation of a fatty diacid with a polyamide having at least four reactive hydrogen atoms per molecule having the formula in which x is at least equal to 1 and R is an alkylene radical containing one to five carbon atoms, the polyamino amide then being quatemized by a salt of epoxy propyl trialkyl ammonium of the formula V different, having one to three carbon atoms, and X is a radical selected from the group consisting of Cl,
- An aqueous dyeing bath for polyacrylonitrile fabrics comprising a cationic dye, and as a retarding and equalization of dyeing agent, a quatemized. polyamino amide obtained by, the condensation'of a fatty diacid with a polyamine having at least four reactive hydrogen atoms per molecule haying the formula lhN-(R-NHF-l-l in which x is at least equal to l and R is an alkylene radical containing one to five carbon atoms, the polyamino amide then being quatemized by a salt of epoxy propyl trialkyl ammonium of the formula in which R, R" and R are alkyl radicals, identical or different, having one to three carbon atoms, and X is a radical selected from the group consisting of Cl, N0 and S0 7 4.
- An aqueous dyeing bath according to claim 3 wherein the proportion of the quatemized polyaminoamide in the dye bath is between 0.2 and 5% per with
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR7212861A FR2178833B1 (enrdf_load_stackoverflow) | 1972-04-07 | 1972-04-07 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3854872A true US3854872A (en) | 1974-12-17 |
Family
ID=9096756
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US00345850A Expired - Lifetime US3854872A (en) | 1972-04-07 | 1973-03-29 | Process for dyeing of polyacrylonitrile fibers |
Country Status (3)
Country | Link |
---|---|
US (1) | US3854872A (enrdf_load_stackoverflow) |
DE (1) | DE2317492A1 (enrdf_load_stackoverflow) |
FR (1) | FR2178833B1 (enrdf_load_stackoverflow) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5667533A (en) * | 1996-02-07 | 1997-09-16 | The Virkler Company | Heather dyed fabric and method of producing same |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3619121A (en) * | 1969-08-07 | 1971-11-09 | Bayer Ag | Polyacrylonitrile dyeing with n-alkylaminoalkylsulfonic acids and basic dyes |
US3716329A (en) * | 1970-11-27 | 1973-02-13 | J Komninos | Dyeing polyacrylonitrile with basic dyestuff and alkoxymethyl quaternary ammonium compounds |
US3773463A (en) * | 1972-04-18 | 1973-11-20 | Sybron Corp | Lubricating, antistat and dye leveling agent and process for textile materials |
US3785768A (en) * | 1970-09-11 | 1974-01-15 | Bayer Ag | Process for the dyeing of fibre material consisting of polyacrylonitrile or acrylonitrile-containing copolymers |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1190096A (fr) * | 1957-01-14 | 1959-10-09 | Ciba Geigy | Nouveaux composés d'ammonium diquaternaires et procédé pour leur préparation |
-
1972
- 1972-04-07 FR FR7212861A patent/FR2178833B1/fr not_active Expired
-
1973
- 1973-03-29 US US00345850A patent/US3854872A/en not_active Expired - Lifetime
- 1973-04-06 DE DE2317492A patent/DE2317492A1/de active Pending
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3619121A (en) * | 1969-08-07 | 1971-11-09 | Bayer Ag | Polyacrylonitrile dyeing with n-alkylaminoalkylsulfonic acids and basic dyes |
US3785768A (en) * | 1970-09-11 | 1974-01-15 | Bayer Ag | Process for the dyeing of fibre material consisting of polyacrylonitrile or acrylonitrile-containing copolymers |
US3716329A (en) * | 1970-11-27 | 1973-02-13 | J Komninos | Dyeing polyacrylonitrile with basic dyestuff and alkoxymethyl quaternary ammonium compounds |
US3773463A (en) * | 1972-04-18 | 1973-11-20 | Sybron Corp | Lubricating, antistat and dye leveling agent and process for textile materials |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5667533A (en) * | 1996-02-07 | 1997-09-16 | The Virkler Company | Heather dyed fabric and method of producing same |
Also Published As
Publication number | Publication date |
---|---|
FR2178833A1 (enrdf_load_stackoverflow) | 1973-11-16 |
DE2317492A1 (de) | 1973-10-18 |
FR2178833B1 (enrdf_load_stackoverflow) | 1975-03-21 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US2895785A (en) | Naoas | |
KR880002282B1 (ko) | 착색 견뢰도의 향상 방법 | |
US3006935A (en) | New polyglycol ether derivatives | |
US3104933A (en) | Method of dyeing with polyvinyl alcohol ester and quaternary ammonium compounds | |
US3854872A (en) | Process for dyeing of polyacrylonitrile fibers | |
CN110965374A (zh) | 一种环保耐氯固色剂及其制备方法 | |
DE2843645A1 (de) | Verfahren zum auswaschen von nicht fixierten reaktivfarbstoffen von cellulosefasern | |
US3691110A (en) | Antistatic treating agent from polyepoxide-polyamine reaction | |
EP0352285B1 (en) | Process for dyeing wool and other keratin fibres | |
HK1006471B (en) | Process for dyeing wool and other keratin fibres | |
JPS6220312B2 (enrdf_load_stackoverflow) | ||
GB2168364A (en) | Sulphates of oxyalkylated amines and their use as dyeing assistants | |
SU454745A3 (ru) | Способ получени водорастворимых пр мых антрахиноновых красителей | |
US4123222A (en) | Process for the dyeing or printing of polyacrylonitrile material | |
GB508079A (en) | Process for treating textile materials | |
US3255078A (en) | Process for the treatment of fiber articles of synthetic polyamides and composition produced | |
US4758671A (en) | Water-soluble cation-active polyelectrolytes | |
US3658460A (en) | Process for dyeing synthetic polyamide textiles in the presence of organic sulphonic acids and basic nitrogen compounds | |
SU638270A3 (ru) | Способ крашени текстильного материала из натуральных или синтетических полиамидных волокон | |
US3707395A (en) | Process for the production of nonwoven fabrics containing binders | |
US4579560A (en) | Method for dyeing of fibers in the presence of quaternary alkoxyalkylammonium retarding or leveling agent | |
US4787910A (en) | Condensation products and processes for the after-treatment of dyed polyamides | |
US3579286A (en) | Polyalkylene polyamine thiosulfonated sulfur dye composition and dyeing therewith | |
JPH0333833B2 (enrdf_load_stackoverflow) | ||
GB2119367A (en) | Triazine dye fixing agents |