US3232904A - Spin-dyed polyacrylonitrile filaments - Google Patents
Spin-dyed polyacrylonitrile filaments Download PDFInfo
- Publication number
- US3232904A US3232904A US54365A US5436560A US3232904A US 3232904 A US3232904 A US 3232904A US 54365 A US54365 A US 54365A US 5436560 A US5436560 A US 5436560A US 3232904 A US3232904 A US 3232904A
- Authority
- US
- United States
- Prior art keywords
- spin
- dyed
- filaments
- polyacrylonitrile filaments
- solution
- 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 description 13
- 238000000034 method Methods 0.000 claims description 9
- 238000009987 spinning Methods 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000000975 dye Substances 0.000 claims description 3
- AOMZHDJXSYHPKS-UHFFFAOYSA-L disodium 4-amino-5-hydroxy-3-[(4-nitrophenyl)diazenyl]-6-phenyldiazenylnaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC2=CC(S([O-])(=O)=O)=C(N=NC=3C=CC=CC=3)C(O)=C2C(N)=C1N=NC1=CC=C([N+]([O-])=O)C=C1 AOMZHDJXSYHPKS-UHFFFAOYSA-L 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 159000000014 iron salts Chemical class 0.000 description 1
- NLRKCXQQSUWLCH-UHFFFAOYSA-N nitrosobenzene Chemical compound O=NC1=CC=CC=C1 NLRKCXQQSUWLCH-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- 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
- D01F6/02—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D01F6/18—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds from polymers of unsaturated nitriles, e.g. polyacrylonitrile, polyvinylidene cyanide
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
-
- 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
- D01F1/00—General methods for the manufacture of artificial filaments or the like
- D01F1/02—Addition of substances to the spinning solution or to the melt
- D01F1/06—Dyes
-
- 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
- Y10S8/927—Polyacrylonitrile fiber
Definitions
- the invention relates to spin-dyed polyacrylonitrile filaments and to a process of producing the same. More particularly the process consists in dissolving in the spinning solution to be used for the production of polyacrylonitrile filaments a nigrosine base and spinning the solution by conventional methods.
- Nigrosine bases to be used in the present process are known under the classical name Nigrosine Spirit Soluble (Colour Index, 2nd Edition, vol. 3, No. 50415 and Farbstofitabellen by Schultz, 7th Edition, page 427) and are preferably produced by heating an arylamine such as aniline, aniline salts, and nitroor nitroso benzene in the presence of iron and/or iron salts at about 180 to 200 C. They are of more or less indefinite structure.
- the process is advantageously carried out by dissolving the afore-mentioned nigrosine bases into the vinyl polymer in dissolved state.
- the dyestuffs are preferably dissolved in the organic solvent commonly used for spinning of the polyacrylonitrile, such as in dimetlhyl formamide.
- the solution thus obtained is then mixed with the solution of the acrylonitrile polymer and then worked up into shaped articles, particularly into filaments and fibres respectively.
- the new process leads to dark spin-dyed polyacrylonitrile fibres which exhibit excellent fastness properties
- Example 15 kilograms of polyacrylonitrile and 0.150 kilogram of Nigrosine Spirit Soluble (Colour Index, 2nd Edition, No. 50415) are dissolved in kilograms of dimethylformamide and the solution is then spun in conventional manner. A deep black spin-dyed fabric is thus obtained which exhibits excellent fastness proper-ties.
- a process for the manufacture of spin-dyed polyacrylonitrile filaments which comprises dissolving in the spinning solution to be used for the production of polyacrylonitrile filaments a nigrosine spirit soluble dyestuff and spinning the solution.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Manufacturing & Machinery (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Artificial Filaments (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF18157A DE1109830B (de) | 1955-08-10 | 1955-08-10 | Verfahren zur Herstellung spinngefaerbter Polyacrylnitrilfaeden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3232904A true US3232904A (en) | 1966-02-01 |
Family
ID=7088844
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US54365A Expired - Lifetime US3232904A (en) | 1955-08-10 | 1960-09-07 | Spin-dyed polyacrylonitrile filaments |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3232904A (fr) |
| DE (1) | DE1109830B (fr) |
| FR (1) | FR1155366A (fr) |
| GB (1) | GB817614A (fr) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4160760A (en) * | 1977-08-22 | 1979-07-10 | Northwestern University | Process for preparing polyacrylonitrile doped with Prussion blue |
| US4557732A (en) * | 1978-05-26 | 1985-12-10 | Hoechst Aktiengesellschaft | Process for spin-dyeing of acid-modified polymers of acrylonitrile by the wet-spinning procedure using quaternary ammonium or cyclammonium dyestuffs of low M value and high cation weight having two or three said ammonium or cyclammonium groups |
| US4607071A (en) * | 1978-05-26 | 1986-08-19 | Hoechst Aktiengesellschaft | Process for spin-dyeing of acid-modified polymers of copolymers of acrylonitrile using rapid-fixing di-quaternary cationic dyes |
| US4663365A (en) * | 1984-08-18 | 1987-05-05 | Bayer Aktiengesellschaft | Wash-resistant, antimicrobially-active fibres and threads and their manufacture |
| US20110233810A1 (en) * | 2010-03-25 | 2011-09-29 | W. M. Barr & Company | Antimicrobial plastic compositions and methods for preparing same |
| CN103590192A (zh) * | 2013-10-15 | 2014-02-19 | 浙江三志纺织有限公司 | 分散蓝2bln/聚丙烯腈基有色纳米纤维膜制备方法 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11724386B2 (en) | 2019-05-27 | 2023-08-15 | Ati Industrial Automation, Inc. | Robotic tool holder with passive compliance |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2527863A (en) * | 1947-08-29 | 1950-10-31 | Du Pont | Modification and dyeing of acrylonitrile polymers |
| US2531407A (en) * | 1946-10-25 | 1950-11-28 | Ind Rayon Corp | N,n-dimethyl acetamide-containing compositions |
| US2857373A (en) * | 1955-03-01 | 1958-10-21 | Eastman Kodak Co | Benzothiazole azo compounds containing a reactive methylene coupling component |
| CA581247A (fr) * | 1959-08-11 | Ciba Limited | Structures faconnees de polymeres d'acrylonitrile avec des teintures du groupe d'indulines et nigrosines | |
| US2941970A (en) * | 1955-06-08 | 1960-06-21 | Chemstrand Corp | Method for dispersion of pigments in acrylonitrile polymer solutions |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE506178A (fr) * | 1950-11-13 | |||
| US2701801A (en) * | 1953-10-09 | 1955-02-08 | Du Pont | Nu-substituted diamino anthraquinone dicarboximide dyes |
-
1955
- 1955-08-10 DE DEF18157A patent/DE1109830B/de active Pending
-
1956
- 1956-08-03 GB GB24058/56A patent/GB817614A/en not_active Expired
- 1956-08-03 FR FR1155366D patent/FR1155366A/fr not_active Expired
-
1960
- 1960-09-07 US US54365A patent/US3232904A/en not_active Expired - Lifetime
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA581247A (fr) * | 1959-08-11 | Ciba Limited | Structures faconnees de polymeres d'acrylonitrile avec des teintures du groupe d'indulines et nigrosines | |
| US2531407A (en) * | 1946-10-25 | 1950-11-28 | Ind Rayon Corp | N,n-dimethyl acetamide-containing compositions |
| US2527863A (en) * | 1947-08-29 | 1950-10-31 | Du Pont | Modification and dyeing of acrylonitrile polymers |
| US2857373A (en) * | 1955-03-01 | 1958-10-21 | Eastman Kodak Co | Benzothiazole azo compounds containing a reactive methylene coupling component |
| US2941970A (en) * | 1955-06-08 | 1960-06-21 | Chemstrand Corp | Method for dispersion of pigments in acrylonitrile polymer solutions |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4160760A (en) * | 1977-08-22 | 1979-07-10 | Northwestern University | Process for preparing polyacrylonitrile doped with Prussion blue |
| US4557732A (en) * | 1978-05-26 | 1985-12-10 | Hoechst Aktiengesellschaft | Process for spin-dyeing of acid-modified polymers of acrylonitrile by the wet-spinning procedure using quaternary ammonium or cyclammonium dyestuffs of low M value and high cation weight having two or three said ammonium or cyclammonium groups |
| US4607071A (en) * | 1978-05-26 | 1986-08-19 | Hoechst Aktiengesellschaft | Process for spin-dyeing of acid-modified polymers of copolymers of acrylonitrile using rapid-fixing di-quaternary cationic dyes |
| US4663365A (en) * | 1984-08-18 | 1987-05-05 | Bayer Aktiengesellschaft | Wash-resistant, antimicrobially-active fibres and threads and their manufacture |
| US20110233810A1 (en) * | 2010-03-25 | 2011-09-29 | W. M. Barr & Company | Antimicrobial plastic compositions and methods for preparing same |
| CN103590192A (zh) * | 2013-10-15 | 2014-02-19 | 浙江三志纺织有限公司 | 分散蓝2bln/聚丙烯腈基有色纳米纤维膜制备方法 |
| CN103590192B (zh) * | 2013-10-15 | 2016-01-06 | 浙江三志纺织有限公司 | 分散蓝2bln/聚丙烯腈基有色纳米纤维膜制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| GB817614A (en) | 1959-08-06 |
| DE1109830B (de) | 1961-06-29 |
| FR1155366A (fr) | 1958-04-25 |
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