GB2132641A - Acidulant for dyeing process - Google Patents
Acidulant for dyeing process Download PDFInfo
- Publication number
- GB2132641A GB2132641A GB08322234A GB8322234A GB2132641A GB 2132641 A GB2132641 A GB 2132641A GB 08322234 A GB08322234 A GB 08322234A GB 8322234 A GB8322234 A GB 8322234A GB 2132641 A GB2132641 A GB 2132641A
- Authority
- GB
- United Kingdom
- Prior art keywords
- glycol
- formates
- dyeing
- process according
- printing
- 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.)
- Granted
Links
- 238000004043 dyeing Methods 0.000 title claims abstract description 27
- 238000000034 method Methods 0.000 title claims abstract description 26
- 230000008569 process Effects 0.000 title claims abstract description 26
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 41
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 27
- -1 Glycol formate esters Chemical class 0.000 claims abstract description 24
- 239000002253 acid Substances 0.000 claims abstract description 21
- 239000004744 fabric Substances 0.000 claims abstract description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims abstract description 9
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000002518 antifoaming agent Substances 0.000 claims description 2
- 238000004040 coloring Methods 0.000 claims description 2
- 239000012467 final product Substances 0.000 claims description 2
- 238000003801 milling Methods 0.000 claims description 2
- 230000001105 regulatory effect Effects 0.000 claims description 2
- 238000009991 scouring Methods 0.000 claims description 2
- 239000002562 thickening agent Substances 0.000 claims description 2
- 238000004078 waterproofing Methods 0.000 claims description 2
- 239000000080 wetting agent Substances 0.000 claims description 2
- 239000000975 dye Substances 0.000 abstract description 28
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract description 16
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract description 8
- 235000019253 formic acid Nutrition 0.000 abstract description 8
- 150000007513 acids Chemical class 0.000 abstract description 7
- 150000002148 esters Chemical class 0.000 abstract description 7
- 150000007524 organic acids Chemical class 0.000 abstract description 7
- 235000005985 organic acids Nutrition 0.000 abstract description 7
- 229920002994 synthetic fiber Polymers 0.000 abstract description 5
- 239000000654 additive Substances 0.000 abstract description 3
- 239000007788 liquid Substances 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 abstract description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 10
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 10
- 239000001166 ammonium sulphate Substances 0.000 description 10
- 235000011130 ammonium sulphate Nutrition 0.000 description 10
- 210000002268 wool Anatomy 0.000 description 9
- 150000004675 formic acid derivatives Chemical class 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000000123 paper Substances 0.000 description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- 239000000980 acid dye Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000006172 buffering agent Substances 0.000 description 2
- 230000003139 buffering effect Effects 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 239000003517 fume Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- IKCQWKJZLSDDSS-UHFFFAOYSA-N 2-formyloxyethyl formate Chemical compound O=COCCOC=O IKCQWKJZLSDDSS-UHFFFAOYSA-N 0.000 description 1
- DUYOHDPGXMPOKD-UHFFFAOYSA-N 2-formyloxypropyl formate Chemical compound O=COC(C)COC=O DUYOHDPGXMPOKD-UHFFFAOYSA-N 0.000 description 1
- 239000004348 Glyceryl diacetate Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- HDDLVZWGOPWKFW-UHFFFAOYSA-N Trimethyl citrate Natural products COC(=O)CC(O)(C(=O)OC)CC(=O)OC HDDLVZWGOPWKFW-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 235000019443 glyceryl diacetate Nutrition 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L sodium sulphate Substances [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
- D21H21/28—Colorants ; Pigments or opacifying agents
-
- 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
- D06P1/64—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 low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/651—Compounds without nitrogen
- D06P1/65106—Oxygen-containing compounds
- D06P1/65125—Compounds containing ester groups
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Abstract
Glycol formate esters are used as additives in the dyeing and printing processes for natural and synthetic fibres and fabrics. It has been found that by replacing conventional organic acids either wholly or partially by such easily hydrolysable esters of formic acid, compositions are formed which regulate the pH of the dye bath so as to obtain adequate levelling and exhaustion of dyes while minimising to a substantial extent the problems relating to pH fluctuations, odour and corrosivity of the free acids. The glycol formates used are preferably selected from the diformates of ethylene glycol, propylene glycol and butylene glycol. The glycol formates are liquids and may be used as such or in the form of solutions.
Description
SPECIFICATION
Use of formate esters in dyeing and/or printing processes
The present invention relates to the use of formate esters as additives in the dyeing and printing processes for natural and synthetic fibres and fabrics.
In the dyeing industry organic acids and their salts are commonly used as acidulants in the dyeing of wool, nylon, paper, leather and other natural and synthetic fibres with certain acid and chrome dyes.
Organic acids such as citric acid and acetic acid are also used as components of printing pastes e.g. for printing carpets and in printing processes. The use of such acids and salts is disclosed for example in
French Patent Application No. A-2,240,3 1 7, German Patent Nos. C-3 17725 and C-87429 1, and in GB--AA-1,048,482. These acids and their salts perform several functions in the dyeing and printing processes such as::
to ensure economic exhaustion (defined as the degree of uptake of the dye by the material dyed) from the aqueous dye bath,
to prevent oxidation of the dyestuff by dichromate in the case of certain chrome dyes by the reducing action of acid such as formic acid,
to achieve rapid dyeing of wool by padding (immersing and then nipping) wool fabric with a concentrated solution of the dye in formic acid,
to achieve and maintain the desired pH conditions for the printing of wool and other fabrics, and
to achieve adequate levelling (evenness or uniformity of dyeing) with certain dyes, e.g. mordant acid dye and premetallised dye wherein the acid is used in the form of its neutral salt for the buffering effect to maintain a constant pH.
In all the above applications, the use of free organic acids as acidulants presents two main problems. Firstly, the intermittent addition of free acid into the system causes a sudden upsurge of acidity in the system at the time of addition thereby impairing the quality of dyeing. Secondly, the use of free organic acids presents handling problems due to the disagreeable odours of the acid fumes, and the need to wear protective clothing and also results in corrosion of equipment and machinery exposed to such acids and fumes.
It is therefore necessary to ensure that the acidulant used results in a gradual shift of the dyebath pH from alkaline to acid. If this can be achieved, the dyeing process can be initiated in an alkaline medium and will offer the optimum conditions for uniform distribution and exhaustion of the dye and will ensure very level dyeings. At the same time it will be advantageous if the use of free acids can be avoided so as to minimise problems of corrosion and handling.
The problem has to some extent been solved by the use of proprietary esters such as diacetin and acetyl trimethyl citrate. Both these release the acid "in situ" by hydrolysis under the dyeing conditions and thereby offset the handling problems. However, the rate of hydrolysis is relatively slow and the pH values attainable are not adequate for dyes which need strongly acid media. Examples of such processes include the use of acid dyes in (a) dyeing polyamides (pH 3.5-3.5) or polypropylene (pH 2.5-3.0), and (b) printing pastes for printing and fixing carpets which need the use of a strong acid, e.g.
formic acid. Moreover, when using azoic dyes the coupling thereof on dried prints needs exposure to steam containing vapours of formic and/or acetic acid. In any case these proprietary compounds are relatively expensive.
It has now been found that, by replacing these organic acids either wholly or partially by an easily hydrolysable ester of formic acid, compositions are formed which regulate the pH of the dye bath so as to obtain adequate levelling and exhaustion of dyes while minimising to a substantial extent the problems relating to pH fluctuations, odour and corrosivity of the free acids. The use of these esters in the dyeing process not only minimises the problems relating to odour and corrosivity but also has the surprising advantage of eliminating the need in some cases for separate buffering agents.
Accordingly, the present invention is a dyeing and/or printing process which employs a dye bath comprising an acidulant characterised in that the pH of the dyebath is regulated by a glycol formate which wholly or partially replaces said acidulant.
The glycol formates used are preferably selected from the diformates of ethylene glycol, propylene glycol and butyiene glycol. The glycol formates are liquids and may be used as such or in the form of solutions.
The glycol formates can be incorporated into the dyeing and/or printing process at various points in the process, for example at one or more of the stages of scouring of the fabric, mordanting, levelling, exhaustion, fixing, finishing, water-proofing and milling. These terms are well known in the art and are defined in standard text books such as for example, "Textile Auxiliaries", by Batty, J. W.
Pergamon Press (1967) and "The Theory and Practice of Wool Dyeing" by Bird, C. L. published by the
Society of Dyers and Colourists, Bradford, Yorkshire (1963), 3rd Edition.
Typically, in the dyeing of wool the machine is loaded with wool and water is added together with the glycol formates which wholly or partially replace the acids (e.g. formic acid, acetic acid) normally used, the levelling agents and pH control agents (e.g. sodium and ammonium sulphate). In certain instances additional pH control agents can be omitted because the glycol formates avoid wide fiuctuations of pH thus also performing a buffering function. The dye bath is held at 400C for 5-30 minutes, the dye is added and the bath raised to the boil in 45-60 minutes. The dye bath is held at the boil for 30-60 minutes. At this stage more ester can be added, if necessary, to maintain the pH and to complete dye exhaustion.In such dyeing processes the glycol formates used in the present invention may be added with the initial charge of water to replace either the acid or the levelling agent or both.
The concentration used (on a 100% basis) may be in the range of 0.110% w/w based on the weight of the fabric being dyed or printed. The glycol formates which are liquids may be added as such or as solutions of the formates in a solvent. Additionally, the solutions can be used as a solvent carrier for the dyes. Where the glycol formates are used in the printing of fabrics, they can be added to the printing paste at a concentration of between 0.1 and 10% w/w of the paste depending upon the type of fabric which is being printed.
In dyeing or printing paper, the control of pH is essential and the glycol formates used in the present invention not only enable such control but also can be added to the dye used for colouring the pulp or the final product paper.
The glycol formates used in the present invention may be used in conjunction with other conventional assistants or agents such as for example wetting agents, anti-foaming agents, solubilising agents and thickeners, used in the dyeing or printing process.
The types of dyes used are not limited by the process of the present invention. For example the dyes may be acid, azoic, basic, direct, indirect, dispersed, reactive, mordant, premetallised, solvent, sulphur, vat dyes and optical brighteners.
The principal advantages of using the glycol formates in the dye bath or in printing pastes are as follows:
They are less corrosive to skin, clothing, plastics and metal and hence are safer to the operator and do not promote deterioration of equipment.
They are less volatile than conventional compositions containing the free organic acids (e.g. formic acid, acetic acid).
Solutions of the glycol formates will act as buffer systems thereby preventing sudden upsurge in the pH value of the dye bath when fresh amounts of the ester are added either alone or together with free acid. This enables achievement of a controlled reduction in pH of the bath thereby eliminating in some cases, the need for a buffering agent.
Typical formates are relatively less expensive than other proprietary esters now in use.
The ease of hydrolysis of these formates result in shorter dyeing times.
The present invention is further illustrated with reference to the following Examples.
EXAMPLE 1
The following simple tests were performed as control tests (without any dye) to test the ability of the glycol formates to gradually regulate the pH from a neutral/alkaline medium to acid.
The fibre used in the dye bath was untreated 2/40 Nm wool yarn (10 g) at a liquor to wool ratio of 30:1. The tests were carried out in a John Jeffreys Dyemaster apparatus and the liquor used was water with, where indicated, 4% by weight of ammonium sulphate and the acidulant in the concentration specified. The temperature was raised from 200C to the boil over 60 minutes and held for a further 60 minutes.The results are tabulated below.
Time (mins) 0 2 0 40 6 0 80 1 0 0 1 2 0 1 40 Control (No additive) pH 7.7 5 8.2 4 8.3 6 8.1 8.0 5 7.9 6 7.9 7.84 0.1 g/l of EGDF** + Ammonium Sulphate pH 7.6 7.5 7.4 7.2 7.0 7.0 6.8 6.6 0.2 g/l fo EGDF** P Ammonium Sulphate pH 7.5 7.6 7.1 6.9 6.5 6.3 6.1 5.9 0.5 g/l EGDF** + Ammonium Sulphate pH 7.5 7.4 6.9 6.4 5.9 5.6 5.5 5.4 1.0 g/l EGDFM + Ammonium Sulphate pH 7.1 7.0 6.5 5.9 5.4 5.2 5.1 4.9 0.1 g/l PGDF* + Ammonium Sulphate pH 7.9 7.9 7.6 7.1 7.0 6.9 6.6 6.5 0.2 g/l PGDF* + Ammonium Sulphate pH 7.9 7.8 7.4 6.8 6.6 6.4 6.2 6.1 0.5 g/l PGDF+ + Ammonium Sulphate pH 7.6 7.5 7.0 6.3 6.0 5.7 5.5 5.4 1.0 g/l PGDF* + Ammonium Sulphate pH 7.5 7.3 6.7 5.8 5.5 5.3 5.2 5.1
EGDF** = Ethylene glycol diformate
PGDF* = Propylene glycol diformate
Claims (9)
1. A dyeing and/or printing process which employs a dye bath comprising an acidulant characterised in that the pH of the dyebath is regulated by a glycol formate which wholly or partially replaces said acidulant.
2. A process according to claim 1 wherein the glycol formates used are selected from the diformates of ethylene glycol, propylene glycol and butylene glycol.
3. A process according to any one of the preceding claims wherein the glycol formates are used as such or in the form of solutions in a solvent.
4. A process according to any one of the preceding claims wherein the glycol formates are incorporated into the dyeing and/or printing process at one or more of the following stages of scouring of the fabric, mordanting, levelling, exhaustion, fixing, finishing water-proofing and milling.
5. A process according to any one of the preceding claims wherein the glycol formate is used in the absence of additional pH control agents.
6. A process according to any one of the preceding claims wherein the glycol formates are added with the initial charge of water to replace either the acid or the levelling agent or both.
7. A process according to any one of the preceding claims wherein the concentration of glycol formate used (on a 100% basis) is in the range of 0.110% w/w based on the weight of the fabric being dyed or printed.
8. A process for dyeing or printing paper, wherein the glycol formates are added to the dye used for colouring the pulp or the final product paper.
9. A process according to any one of the preceding claims wherein the glycol formates are used in conjunction with wetting agents, anti-foaming agents, solubilising agents and thickeners used in the dyeing or printing process.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB08322234A GB2132641B (en) | 1982-08-25 | 1983-08-18 | Acidulent for dyeing process |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8224388 | 1982-08-25 | ||
| GB08322234A GB2132641B (en) | 1982-08-25 | 1983-08-18 | Acidulent for dyeing process |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8322234D0 GB8322234D0 (en) | 1983-09-21 |
| GB2132641A true GB2132641A (en) | 1984-07-11 |
| GB2132641B GB2132641B (en) | 1985-10-02 |
Family
ID=26283670
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08322234A Expired GB2132641B (en) | 1982-08-25 | 1983-08-18 | Acidulent for dyeing process |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2132641B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0210318A2 (en) * | 1985-07-30 | 1987-02-04 | Meisei Chemical Works, Ltd. | Process for scouring and dyeing synthetic fibers in one-bath |
| EP0252689A2 (en) * | 1986-07-09 | 1988-01-13 | BP Chemicals Limited | Textile processing acidulants |
| EP0442749A2 (en) * | 1990-02-14 | 1991-08-21 | BP Chemicals Limited | Textile processing acidulants |
| EP1111123A1 (en) * | 1999-12-21 | 2001-06-27 | Basf Corporation | Methods for deep shade dyeing of textile articles containing melamine fibers |
-
1983
- 1983-08-18 GB GB08322234A patent/GB2132641B/en not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0210318A2 (en) * | 1985-07-30 | 1987-02-04 | Meisei Chemical Works, Ltd. | Process for scouring and dyeing synthetic fibers in one-bath |
| EP0210318A3 (en) * | 1985-07-30 | 1988-06-15 | Meisei Chemical Works, Ltd. | Process for scouring and dyeing synthetic fibers in one-bath |
| EP0252689A2 (en) * | 1986-07-09 | 1988-01-13 | BP Chemicals Limited | Textile processing acidulants |
| EP0252689A3 (en) * | 1986-07-09 | 1988-12-28 | Bp Chemicals Limited | Textile processing acidulants |
| EP0442749A2 (en) * | 1990-02-14 | 1991-08-21 | BP Chemicals Limited | Textile processing acidulants |
| EP0442749A3 (en) * | 1990-02-14 | 1992-01-15 | Bp Chemicals Limited | Textile processing acidulants |
| EP1111123A1 (en) * | 1999-12-21 | 2001-06-27 | Basf Corporation | Methods for deep shade dyeing of textile articles containing melamine fibers |
Also Published As
| Publication number | Publication date |
|---|---|
| GB8322234D0 (en) | 1983-09-21 |
| GB2132641B (en) | 1985-10-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 732 | Registration of transactions, instruments or events in the register (sect. 32/1977) | ||
| 732E | Amendments to the register in respect of changes of name or changes affecting rights (sect. 32/1977) | ||
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