US3787175A - Space-dyeing cellulose fibers by impregnating with mixture of diazonium - Google Patents
Space-dyeing cellulose fibers by impregnating with mixture of diazonium Download PDFInfo
- Publication number
- US3787175A US3787175A US00200166A US3787175DA US3787175A US 3787175 A US3787175 A US 3787175A US 00200166 A US00200166 A US 00200166A US 3787175D A US3787175D A US 3787175DA US 3787175 A US3787175 A US 3787175A
- Authority
- US
- United States
- Prior art keywords
- injection
- dyeing
- mixture
- diazonium
- 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
- 239000000203 mixture Substances 0.000 title abstract description 21
- 238000009977 space dyeing Methods 0.000 title abstract description 8
- 229920003043 Cellulose fiber Polymers 0.000 title abstract description 6
- 239000012954 diazonium Substances 0.000 title description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 title description 4
- 238000000034 method Methods 0.000 abstract description 17
- 150000001989 diazonium salts Chemical class 0.000 abstract description 11
- 239000002253 acid Substances 0.000 abstract description 10
- 239000000463 material Substances 0.000 abstract description 8
- 239000004753 textile Substances 0.000 abstract description 7
- 239000000126 substance Substances 0.000 abstract description 6
- 239000007864 aqueous solution Substances 0.000 abstract description 4
- 150000004982 aromatic amines Chemical class 0.000 abstract description 3
- 238000006149 azo coupling reaction Methods 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 32
- 238000002347 injection Methods 0.000 description 27
- 239000007924 injection Substances 0.000 description 27
- 238000004043 dyeing Methods 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 238000010168 coupling process Methods 0.000 description 13
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 13
- 230000008878 coupling Effects 0.000 description 12
- 238000005859 coupling reaction Methods 0.000 description 12
- 239000000975 dye Substances 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000002657 fibrous material Substances 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- -1 heterocyclic hydroxy compounds Chemical class 0.000 description 7
- 238000005470 impregnation Methods 0.000 description 7
- 229920002678 cellulose Polymers 0.000 description 6
- 239000001913 cellulose Substances 0.000 description 6
- 230000002093 peripheral effect Effects 0.000 description 5
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000001632 sodium acetate Substances 0.000 description 4
- 235000017281 sodium acetate Nutrition 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229960000846 camphor Drugs 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 230000001788 irregular Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical class C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- JSCNDCWUFHAJQL-UHFFFAOYSA-N 2-hydroxy-9h-carbazole-3-carboxylic acid Chemical compound N1C2=CC=CC=C2C2=C1C=C(O)C(C(=O)O)=C2 JSCNDCWUFHAJQL-UHFFFAOYSA-N 0.000 description 1
- PHQKCVOZVPSTAF-UHFFFAOYSA-N 3-hydroxyanthracene-2-carboxylic acid Chemical compound C1=CC=C2C=C(C=C(C(C(=O)O)=C3)O)C3=CC2=C1 PHQKCVOZVPSTAF-UHFFFAOYSA-N 0.000 description 1
- HXUIDZOMTRMIOE-UHFFFAOYSA-N 3-oxo-3-phenylpropionic acid Chemical compound OC(=O)CC(=O)C1=CC=CC=C1 HXUIDZOMTRMIOE-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000005204 hydroxybenzenes Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 150000003142 primary aromatic amines Chemical class 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000004804 winding Methods 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
- 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
- D06P3/58—Material containing hydroxyl groups
- D06P3/60—Natural or regenerated cellulose
- D06P3/68—Preparing azo dyes on the material
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06B—TREATING TEXTILE MATERIALS USING LIQUIDS, GASES OR VAPOURS
- D06B11/00—Treatment of selected parts of textile materials, e.g. partial dyeing
-
- 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
- D06P1/0096—Multicolour dyeing
-
- 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
- Y10S8/916—Natural fiber dyeing
- Y10S8/918—Cellulose textile
Definitions
- the present invention relates to a process for the space-dyeing of cellulose fibers.
- German Patent No. 1,244,104 it is known to dye yarn containing cellulose fibers with reactive dyestuffs irregularly in such a manner that no repetition of pattern occurs on the finished textile materials after the yarn thus dyed has been woven or knitted.
- this dyeing method known as space-dyeing, an alkaline reactive dyestuff solution is injected into the wound-up fibrous material at different places and the wound package is then allowed to dwell until the dyestuff has reacted with the cellulose.
- the number of shades obtained in the bobbin depends on the number of injection locations chosen.
- pretreatment of the wound-up yarns with the impregnation baths containing the alkaline substances and the coupling components is advantageously carried out in a dyeing apparatus, for example a device for dyeing cross-wound bobbins.
- This process step ensures simultaneous impregnation of a large number of bobbins and thus does practically not reduce the production rate, especially since the second lot can be already impregnated while the bobbins of the first lot are injected with the solution of the diazo components.
- the wound packages pre-treated with alkali and coupling component can be stored and taken to use at any time and in any amount since the impregnated bobbins, after drying, are stable upon storage for an almost unlimited period of time if care is taken that any access of moisture is prevented.
- coupling components are used, preferably those of substantive nature toward the fibrous material.
- arylamides of aromatic or heterocyclic o-hydroxycarboxylic acids or of acylacetic acids are, for example, the arylamides of 2,3-hydroxy-naphthoic acid, 2-hydroxyanthracene-3- carboxylic acid, 4-hydroxy-diphenyl-3-carboxylic acid,
- 2-hydroxy-carbazole-3-carboxylic acid 3 -hydroxydiphenylene-oxide-Z-carboxylic acid 3-hydroxydiphenylenesulfide-2-carboxylic acid, aceto-acetic acid or of benzoylacetic acid.
- hydroxybenzenes, polyhydroxy-benzenes, hydroxynaphthalenes and pyrazo-lones have proved suitable among others, which may be substituted by non-ionic radicals.
- any inorganic alkaline substance may be used in the impregnation baths; preferably sodium hydroxide solution.
- These baths may also contain commercial-type non-ionic or anionic wetting agents for a better penetration of the yarn; for example wetting agents on the basis of the reaction products of alkylene oxides with alkyl phenols, of mixtures consisting of high-molecular oxyalkylation products of alkanols or alkyl-phenols and alkyl-sulfuric acid esters of alkaneor alkyl-aryl-sulfonic acids, or of naphthalene-sulfonic acid derivatives.
- the fibrous material is treated with the impregnation bath fo r 10 to 40 minutes, preferably for 30 minutes, at a temperature of from 20 to50C, preferably at room temperature.
- the bobbins After impregnation, the bobbins are centrifuged or sucked and can immediately be conducted to injection while still moist. Intermediate drying of the pre-treated goods is not necessary but it results in a higher liquor absorption during the subsequent injection since the fibrous material has a better absorptive power when dry.
- any primary aromatic amine may be used, which yields water-insoluble mono-, disor polyazo dyestuffs with the above-specified coupling components, thus the tetrazonium compounds of aromatic diamines and the fast color salts obtainable by stabilization from the corresponding amines, too.
- the said suitable amines among them amino-azo dyestuffs, have no ionic substituents.
- aqueous solutions are prepared from the substances chosen, a mixture is composed from at least two of these solutions and a small amount of each solution is applied in a drop to a filter paper that has been preliminarily impregnated with the alkaline solution of a coupling component and dried.
- this test demonstrates that a peripheral zone having a shade different from that of the center of the drop applied is obtained on the substrate.
- the acid solution of the diazonium compounds is injected under pressure into the package that has been pre-treated with the coupling component, at least at one selected portion of the wound material.
- the coloring liquid thus spreads out along the limited injection zone, so that along the length of the yarn of the wound package, dyed and undyed areas of varying lengths are produced at quite irregular intervals.
- the amount of the diazonium compounds injected may, of course, be varied. It depends on the desired ratio of dyed and undyed yarn.
- the injection of the dyeing liquor at several locations may be carried out separately or simultaneously. To obtain a definite non-repeating pattern the injection positions must, of course, be selected in a suitable manner.
- diazonium solutions that yield patterns of different shades upon development with the coupling component may also be injected into the package, either separately or simultaneously.
- the injection mechanism contains as the most essential element a hollow injection needle which has a perforated shaft (for more details see Astrodyed (registered trademark) Technical Manual, Astro Dye Works, lnc., Calhoun, Ga. 3070l/USA, page 12, FIG. 14).
- the length of the needle approximately corresponds to the thickness of the wound package to be treated.
- the position of the injection needle support can be rearranged so that the point of the injection needle can penetrate the package from the outside yarn layer to a desired position inside the thickness of the winding, whereupon the inflow of the dyeing liquor sets in. The flow of the liquor may be stopped again by a reversed motion of the needle support.
- aqueous solutions of the diazo components are injected into the wound-up fibrous material.
- the pH value of these solutions is adjusted to 4.5 6.9 by means of known buffer mixtures or weak acids, especially acetic acid.
- it is suitable to add commercial-type non-ionic dispersants, for example on the basis of the reaction products of alkylene oxides with cresol-camphor resins, or of mixtures consisting of oxyalkylated fatty alcohols and high-molecular-weight polyglycol ethers, to the injection solutions.
- the degree of diffusion of the individual components can be varied by a special selection of the acid or alkali-binder used in the diazonium salt solutions to be injected.
- the bobbins After injection of the diazo components, the bobbins are allowed to dwell for a short time, optionally for up to 5 minutes, and then after-treated as usual and dried.
- the dyeings produced according to the invention show the good fastness properties typical of the ice colors.
- the cellulose fibers may be present in natural or regenerated form. What has been said for the dyeing of yarn is also true for the dyeing of sliver.
- EXAMPLE Six hundred and fifty Grams of wound-up cotton yarn were treated at 20C for 30 minutes in a dyeing apparatus, at a goods-to-liquor ratio of l 25, with the impregnation bath hereinafter disclosed. The wound package was then sucked and dried. At different locations of the bobbin, the below-indicated injection solutions (1) and (2) were injected into the ball of yarn thus impregnated, the liquor absorption of the fibrous material being percent, calculated on the weight of the dry goods. The textile material dyed in this manner was then allowed to dwell for 5 minutes and then aftertreated, in a dyeing apparatus, as usual and dried. lmpregnation bath 3.5 Grams of the compound of the formula were dissolved in 3.5 cc.
- a bobbin was obtained, the yarn of which showed, in the core of the injection location, an intense brown red shade with mixed solution 1 and, at the corresponding peripheral zone, a yellow shade in a reduced breadth.
- the mixed solution 2 yielded, in the center of the injection location, a medium brown shade and, in the quite large peripheral zone, a bright brilliant golden yellow shade.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2057230A DE2057230C3 (de) | 1970-11-20 | 1970-11-20 | Verfahren zum unregelmäßigen Färben von Cellulosefasern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3787175A true US3787175A (en) | 1974-01-22 |
Family
ID=5788710
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00200166A Expired - Lifetime US3787175A (en) | 1970-11-20 | 1971-11-18 | Space-dyeing cellulose fibers by impregnating with mixture of diazonium |
Country Status (13)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USB497473I5 (enrdf_load_stackoverflow) * | 1973-08-16 | 1976-02-03 | ||
| US4331443A (en) * | 1979-02-22 | 1982-05-25 | Hoechst Aktiengesellschaft | Concentrated solutions of water-insoluble coupling components |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3120422A (en) * | 1961-08-03 | 1964-02-04 | Astro Dye Works Inc | Method of making random dyed yarns |
| US3301629A (en) * | 1963-10-10 | 1967-01-31 | Bayer Ag | Process for the production of black dyeings on cellulose fabrics |
| US3393411A (en) * | 1964-07-06 | 1968-07-23 | Stevens & Co Inc J P | Process for dyeing pile material with various colored dyes from a plurality of streams |
| US3620662A (en) * | 1969-10-21 | 1971-11-16 | Toray Industries | Method and apparatus for intermittently dyeing yarns |
-
1970
- 1970-11-20 DE DE2057230A patent/DE2057230C3/de not_active Expired
-
1971
- 1971-11-15 ES ES397030A patent/ES397030A1/es not_active Expired
- 1971-11-15 NL NL7115668A patent/NL7115668A/xx unknown
- 1971-11-17 CH CH1671571D patent/CH1671571A4/xx unknown
- 1971-11-17 CH CH1671571A patent/CH554710A/xx unknown
- 1971-11-18 ZA ZA717748A patent/ZA717748B/xx unknown
- 1971-11-18 US US00200166A patent/US3787175A/en not_active Expired - Lifetime
- 1971-11-18 IT IT31289/71A patent/IT940683B/it active
- 1971-11-18 AU AU35872/71A patent/AU3587271A/en not_active Expired
- 1971-11-19 GB GB5383571A patent/GB1368129A/en not_active Expired
- 1971-11-19 SE SE14812/71A patent/SE365265B/xx unknown
- 1971-11-19 BE BE775580A patent/BE775580A/xx unknown
- 1971-11-19 CA CA128,061A patent/CA962009A/en not_active Expired
- 1971-11-19 FR FR7141497A patent/FR2115278B1/fr not_active Expired
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3120422A (en) * | 1961-08-03 | 1964-02-04 | Astro Dye Works Inc | Method of making random dyed yarns |
| US3301629A (en) * | 1963-10-10 | 1967-01-31 | Bayer Ag | Process for the production of black dyeings on cellulose fabrics |
| US3393411A (en) * | 1964-07-06 | 1968-07-23 | Stevens & Co Inc J P | Process for dyeing pile material with various colored dyes from a plurality of streams |
| US3620662A (en) * | 1969-10-21 | 1971-11-16 | Toray Industries | Method and apparatus for intermittently dyeing yarns |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USB497473I5 (enrdf_load_stackoverflow) * | 1973-08-16 | 1976-02-03 | ||
| US3990839A (en) * | 1973-08-16 | 1976-11-09 | Hoechst Aktiengesellschaft | Process for obtaining irregular shadow dyeings on polyester fibers and mixtures thereof |
| US4331443A (en) * | 1979-02-22 | 1982-05-25 | Hoechst Aktiengesellschaft | Concentrated solutions of water-insoluble coupling components |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2115278A1 (enrdf_load_stackoverflow) | 1972-07-07 |
| CH1671571A4 (enrdf_load_stackoverflow) | 1974-05-15 |
| ES397030A1 (es) | 1974-04-16 |
| DE2057230A1 (de) | 1972-06-08 |
| GB1368129A (en) | 1974-09-25 |
| CA962009A (en) | 1975-02-04 |
| BE775580A (fr) | 1972-05-19 |
| DE2057230C3 (de) | 1974-01-17 |
| IT940683B (it) | 1973-02-20 |
| SE365265B (enrdf_load_stackoverflow) | 1974-03-18 |
| ZA717748B (en) | 1972-08-30 |
| DE2057230B2 (de) | 1973-06-07 |
| CH554710A (enrdf_load_stackoverflow) | 1974-10-15 |
| NL7115668A (enrdf_load_stackoverflow) | 1972-05-24 |
| AU3587271A (en) | 1973-05-24 |
| FR2115278B1 (enrdf_load_stackoverflow) | 1976-06-04 |
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