CA1061507A - Process for dyeing wet-spun aromatic polyamides in gel form - Google Patents
Process for dyeing wet-spun aromatic polyamides in gel formInfo
- Publication number
- CA1061507A CA1061507A CA233,098A CA233098A CA1061507A CA 1061507 A CA1061507 A CA 1061507A CA 233098 A CA233098 A CA 233098A CA 1061507 A CA1061507 A CA 1061507A
- Authority
- CA
- Canada
- Prior art keywords
- filaments
- dye
- bath
- dyed
- spun
- 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
Links
- 238000000034 method Methods 0.000 title claims abstract description 31
- 238000004043 dyeing Methods 0.000 title claims abstract description 20
- 239000004760 aramid Substances 0.000 title claims abstract description 19
- 229920003235 aromatic polyamide Polymers 0.000 title claims abstract description 19
- 125000002091 cationic group Chemical group 0.000 claims abstract description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 8
- 239000002253 acid Substances 0.000 claims abstract description 7
- 125000000129 anionic group Chemical group 0.000 claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- 229920002647 polyamide Polymers 0.000 claims description 9
- 239000004952 Polyamide Substances 0.000 claims description 8
- 239000003495 polar organic solvent Substances 0.000 claims description 6
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
- YCGKJPVUGMBDDS-UHFFFAOYSA-N 3-(6-azabicyclo[3.1.1]hepta-1(7),2,4-triene-6-carbonyl)benzamide Chemical compound NC(=O)C1=CC=CC(C(=O)N2C=3C=C2C=CC=3)=C1 YCGKJPVUGMBDDS-UHFFFAOYSA-N 0.000 claims description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 3
- -1 hexamethyl phosphoric acid Chemical compound 0.000 claims description 3
- 239000012209 synthetic fiber Substances 0.000 abstract 1
- 229920002994 synthetic fiber Polymers 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 63
- 239000000243 solution Substances 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 11
- 229940113088 dimethylacetamide Drugs 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 9
- 238000009987 spinning Methods 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- 238000001556 precipitation Methods 0.000 description 6
- 239000004753 textile Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000005259 measurement Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- 239000001044 red dye Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229920002239 polyacrylonitrile Polymers 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- SDQJTWBNWQABLE-UHFFFAOYSA-N 1h-quinazoline-2,4-dione Chemical group C1=CC=C2C(=O)NC(=O)NC2=C1 SDQJTWBNWQABLE-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- KWNQIIMVPSMYEM-UHFFFAOYSA-N 6,7-dimethoxy-1h-quinazoline-2,4-dione Chemical compound N1C(=O)NC(=O)C2=C1C=C(OC)C(OC)=C2 KWNQIIMVPSMYEM-UHFFFAOYSA-N 0.000 description 1
- 108700040458 Drosophila Strn-Mlck Proteins 0.000 description 1
- 244000228957 Ferula foetida Species 0.000 description 1
- PMDCZENCAXMSOU-UHFFFAOYSA-N N-ethylacetamide Chemical compound CCNC(C)=O PMDCZENCAXMSOU-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 150000004700 cobalt complex Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 238000002166 wet spinning Methods 0.000 description 1
- 239000001043 yellow dye Substances 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
- D06P7/00—Dyeing or printing processes combined with mechanical treatment
- D06P7/005—Dyeing combined with texturising or drawing treatments
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
- D01F6/60—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyamides
- D01F6/605—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyamides from aromatic polyamides
-
- 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
- D06P1/90—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 dyes dissolved in organic solvents or aqueous emulsions thereof
- D06P1/92—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 dyes dissolved in organic solvents or aqueous emulsions thereof in organic solvents
- D06P1/928—Solvents other than hydrocarbons
-
- 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
-
- 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
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Coloring (AREA)
- Artificial Filaments (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2438545A DE2438545C3 (de) | 1974-08-10 | 1974-08-10 | Verfahren zur Herstellung gefärbter Fäden aus vollaromatischen Polyamiden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1061507A true CA1061507A (en) | 1979-09-04 |
Family
ID=5922933
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA233,098A Expired CA1061507A (en) | 1974-08-10 | 1975-08-08 | Process for dyeing wet-spun aromatic polyamides in gel form |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4108936A (enExample) |
| JP (1) | JPS5143421A (enExample) |
| BE (1) | BE832262A (enExample) |
| CA (1) | CA1061507A (enExample) |
| DD (1) | DD123002A5 (enExample) |
| DE (1) | DE2438545C3 (enExample) |
| DK (1) | DK361675A (enExample) |
| ES (1) | ES440105A1 (enExample) |
| FR (1) | FR2281453A1 (enExample) |
| GB (1) | GB1512454A (enExample) |
| IT (1) | IT1041791B (enExample) |
| LU (1) | LU73179A1 (enExample) |
| NL (1) | NL7509440A (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5833974Y2 (ja) * | 1976-10-14 | 1983-07-29 | 株式会社東芝 | 洗浄機器の液体洗剤投入装置 |
| US4668234A (en) * | 1985-08-15 | 1987-05-26 | E. I. Du Pont De Nemours And Company | Aromatic polyamide fibers and process for stabilizing such fibers with surfactants |
| US5242991A (en) * | 1989-11-28 | 1993-09-07 | E. I. Du Pont De Nemours And Company | Quaternary ammonium polyarylamide |
| 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 |
| KR940009563B1 (ko) * | 1992-09-04 | 1994-10-15 | 대우전자주식회사 | 식기 세척기 |
| US5427589A (en) * | 1993-03-03 | 1995-06-27 | Springs Industries, Inc. | Method for dyeing fibrous materials |
| US5437690A (en) * | 1994-05-25 | 1995-08-01 | Springs Industries, Inc. | Method for dyeing fibrous materials and dye assistant relating to the same |
| US5998309A (en) * | 1997-07-17 | 1999-12-07 | E. I. Du Pont De Nemours And Company | Molded aramid sheets |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2558733A (en) * | 1949-06-08 | 1951-07-03 | American Cyanamid Co | Method of producing synthetic fibers from polymers and copolymers of acrylonitrile |
| US3111357A (en) * | 1961-04-14 | 1963-11-19 | Dow Chemical Co | Method of dyeing aquagel acrylonitrile polymer fibers by stretching in a heated aqueous dye bath |
| US3233019A (en) * | 1962-08-07 | 1966-02-01 | Du Pont | Process of multiple neck drawing while simultaneously infusing modifying agent |
| US3483576A (en) * | 1964-03-27 | 1969-12-16 | American Cyanamid Co | Process for continuously preparing dyed filaments of acrylonitrile polymers |
| DE1942409U (de) | 1966-01-17 | 1966-07-14 | Walter Kuehn | Kraftfahrzeug. |
| US3434189A (en) * | 1966-08-02 | 1969-03-25 | Klinger Mfg Co Ltd | Method of continuously dyeing and stretching undrawn yarn |
| US3506990A (en) * | 1966-12-16 | 1970-04-21 | Du Pont | Process for dyeing drawn filaments of aromatic polyamides with basic dye-stuffs in the presence of an organic dye carrier |
| US3543359A (en) * | 1967-08-25 | 1970-12-01 | Whitaker Co Fred | Method of producing multicolored yarn |
| US3602966A (en) * | 1968-05-18 | 1971-09-07 | Fleissner Gmbh | Process and apparatus for treating synthetic filament groups |
| JPS4914430A (enExample) * | 1972-06-10 | 1974-02-07 | ||
| US3888821A (en) * | 1972-11-02 | 1975-06-10 | Du Pont | Aromatic polyamide fibers containing ultraviolet light screeners |
| IT1024071B (it) * | 1973-04-09 | 1978-06-20 | Du Pont | Processo per l'impregnazione di fibre tessili di polimero lineare sintetico difficilmente fusibile e fibre prparate con detto processo |
-
1974
- 1974-08-10 DE DE2438545A patent/DE2438545C3/de not_active Expired
-
1975
- 1975-08-07 US US05/602,676 patent/US4108936A/en not_active Expired - Lifetime
- 1975-08-07 NL NL7509440A patent/NL7509440A/xx not_active Application Discontinuation
- 1975-08-08 DD DD187772A patent/DD123002A5/xx unknown
- 1975-08-08 CA CA233,098A patent/CA1061507A/en not_active Expired
- 1975-08-08 ES ES440105A patent/ES440105A1/es not_active Expired
- 1975-08-08 GB GB33157/75A patent/GB1512454A/en not_active Expired
- 1975-08-08 DK DK361675A patent/DK361675A/da unknown
- 1975-08-08 LU LU73179A patent/LU73179A1/xx unknown
- 1975-08-08 IT IT26263/75A patent/IT1041791B/it active
- 1975-08-08 BE BE159057A patent/BE832262A/xx unknown
- 1975-08-08 FR FR7524872A patent/FR2281453A1/fr active Granted
- 1975-08-11 JP JP50096736A patent/JPS5143421A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5143421A (enExample) | 1976-04-14 |
| BE832262A (fr) | 1976-02-09 |
| NL7509440A (nl) | 1976-02-12 |
| FR2281453B1 (enExample) | 1979-05-18 |
| IT1041791B (it) | 1980-01-10 |
| DD123002A5 (de) | 1976-11-12 |
| DE2438545A1 (de) | 1976-02-19 |
| FR2281453A1 (fr) | 1976-03-05 |
| US4108936A (en) | 1978-08-22 |
| DE2438545B2 (de) | 1978-12-07 |
| LU73179A1 (enExample) | 1976-08-13 |
| DE2438545C3 (de) | 1979-08-09 |
| ES440105A1 (es) | 1977-06-01 |
| GB1512454A (en) | 1978-06-01 |
| DK361675A (da) | 1976-02-11 |
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