DE2433233C3 - Verfahren zum Spinnfärben von Polymeren oder Mischpolymeren des Acrylnitril - Google Patents
Verfahren zum Spinnfärben von Polymeren oder Mischpolymeren des AcrylnitrilInfo
- Publication number
- DE2433233C3 DE2433233C3 DE2433233A DE2433233A DE2433233C3 DE 2433233 C3 DE2433233 C3 DE 2433233C3 DE 2433233 A DE2433233 A DE 2433233A DE 2433233 A DE2433233 A DE 2433233A DE 2433233 C3 DE2433233 C3 DE 2433233C3
- Authority
- DE
- Germany
- Prior art keywords
- acrylonitrile
- dyes
- copolymers
- groups
- spin
- 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 description 13
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 title claims description 11
- 229920000642 polymer Polymers 0.000 title claims description 11
- 229920001577 copolymer Polymers 0.000 title claims description 10
- 238000004043 dyeing Methods 0.000 title claims description 10
- 239000000975 dye Substances 0.000 claims description 28
- 238000009987 spinning Methods 0.000 claims description 13
- 239000000981 basic dye Substances 0.000 claims description 3
- -1 aromatic carboxylic acids Chemical class 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 239000000987 azo dye Substances 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000000835 fiber Substances 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 239000000049 pigment Substances 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 125000004442 acylamino group Chemical group 0.000 description 3
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 229920002239 polyacrylonitrile Polymers 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 125000001425 triazolyl group Chemical group 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000000578 dry spinning Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000002166 wet spinning Methods 0.000 description 2
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical class NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- 102000002265 Human Growth Hormone Human genes 0.000 description 1
- 108010000521 Human Growth Hormone Proteins 0.000 description 1
- 239000000854 Human Growth Hormone Substances 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001448 anilines Chemical group 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N cyclobenzothiazole Natural products C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000007380 fibre production Methods 0.000 description 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
- 238000009998 heat setting Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical group COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229940063153 saizen Drugs 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 150000003852 triazoles Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
- C09B69/06—Dyestuff salts, e.g. salts of acid dyes with basic dyes of cationic dyes with organic acids or with inorganic complex acids
- C09B69/065—Dyestuff salts, e.g. salts of acid dyes with basic dyes of cationic dyes with organic acids or with inorganic complex acids of cationic azo dyes
-
- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
-
- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3472—Five-membered rings
-
- 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
- C09B44/00—Azo dyes containing onium groups
- C09B44/10—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system
- C09B44/18—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system having three nitrogen atoms as the only ring hetero atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
- Coloring (AREA)
- Artificial Filaments (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2433233A DE2433233C3 (de) | 1974-07-11 | 1974-07-11 | Verfahren zum Spinnfärben von Polymeren oder Mischpolymeren des Acrylnitril |
| CH889875A CH616709A5 (en) | 1974-07-11 | 1975-07-08 | Process for spin-dyeing polymers or copolymers of acrylonitrile |
| IT25234/75A IT1039841B (it) | 1974-07-11 | 1975-07-09 | Processo per la tintura mella massa di filatura di polimeri o copolimeri dell acrilonitrile |
| FR7521655A FR2277931A1 (fr) | 1974-07-11 | 1975-07-10 | Procede de teinture dans la masse a filer de polymeres ou de copolymeres d'acrylonitrile |
| JP50084027A JPS5853018B2 (ja) | 1974-07-11 | 1975-07-10 | アクリロニトリルノ ジユウゴウタイ マタハ キヨウジユウゴウタイノゲンエキチヤクシヨクホウ |
| BE158238A BE831300A (fr) | 1974-07-11 | 1975-07-11 | Procede de teinture dans la masse a filer de polymeres ou de copolymeres d'acrylonitrile |
| GB29243/75A GB1514263A (en) | 1974-07-11 | 1975-07-11 | Process for spin-dyeing polymers of acrylonitrile containing acid groups or co-polymers thereof containing acid groups |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2433233A DE2433233C3 (de) | 1974-07-11 | 1974-07-11 | Verfahren zum Spinnfärben von Polymeren oder Mischpolymeren des Acrylnitril |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2433233A1 DE2433233A1 (de) | 1976-01-22 |
| DE2433233B2 DE2433233B2 (de) | 1979-07-05 |
| DE2433233C3 true DE2433233C3 (de) | 1980-03-06 |
Family
ID=5920233
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2433233A Expired DE2433233C3 (de) | 1974-07-11 | 1974-07-11 | Verfahren zum Spinnfärben von Polymeren oder Mischpolymeren des Acrylnitril |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5853018B2 (https=) |
| BE (1) | BE831300A (https=) |
| CH (1) | CH616709A5 (https=) |
| DE (1) | DE2433233C3 (https=) |
| FR (1) | FR2277931A1 (https=) |
| GB (1) | GB1514263A (https=) |
| IT (1) | IT1039841B (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5734909Y2 (https=) * | 1976-12-26 | 1982-08-02 | ||
| JPS5423855U (https=) * | 1977-07-20 | 1979-02-16 | ||
| DE2822913C2 (de) * | 1978-05-26 | 1982-08-19 | Hoechst Ag, 6000 Frankfurt | Verfahren zum Spinnfärben von Polymeren oder Mischpolymeren des Acrylnitrils |
| US4382801A (en) * | 1980-12-24 | 1983-05-10 | Ciba-Geigy Corporation | Process for spin dyeing polymers or copolymers of acrylonitrile with quaternized heterocyclic diazo dye and tetrafluoro-borate anion |
| GB8426102D0 (en) * | 1984-10-16 | 1984-11-21 | Ici Plc | Thermal transfer printing |
| DE3546294A1 (de) * | 1985-12-28 | 1987-07-02 | Hoechst Ag | Neue farbsalze, verfahren zu ihrer herstellung und ihre verwendung |
| JPS63137613A (ja) * | 1986-11-28 | 1988-06-09 | 財団法人 沖縄農林漁業技術開発協会 | さとうきびの脱葉装置 |
| JPH0179928U (https=) * | 1987-11-17 | 1989-05-29 |
-
1974
- 1974-07-11 DE DE2433233A patent/DE2433233C3/de not_active Expired
-
1975
- 1975-07-08 CH CH889875A patent/CH616709A5/de not_active IP Right Cessation
- 1975-07-09 IT IT25234/75A patent/IT1039841B/it active
- 1975-07-10 FR FR7521655A patent/FR2277931A1/fr active Granted
- 1975-07-10 JP JP50084027A patent/JPS5853018B2/ja not_active Expired
- 1975-07-11 BE BE158238A patent/BE831300A/xx not_active IP Right Cessation
- 1975-07-11 GB GB29243/75A patent/GB1514263A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2277931B1 (https=) | 1978-10-13 |
| IT1039841B (it) | 1979-12-10 |
| JPS5131741A (en) | 1976-03-18 |
| JPS5853018B2 (ja) | 1983-11-26 |
| FR2277931A1 (fr) | 1976-02-06 |
| BE831300A (fr) | 1976-01-12 |
| GB1514263A (en) | 1978-06-14 |
| DE2433233A1 (de) | 1976-01-22 |
| DE2433233B2 (de) | 1979-07-05 |
| CH616709A5 (en) | 1980-04-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |