US3515504A - Method for continuous dyeing of textile materials made from linear,aromatic polyesters - Google Patents
Method for continuous dyeing of textile materials made from linear,aromatic polyesters Download PDFInfo
- Publication number
- US3515504A US3515504A US688005A US3515504DA US3515504A US 3515504 A US3515504 A US 3515504A US 688005 A US688005 A US 688005A US 3515504D A US3515504D A US 3515504DA US 3515504 A US3515504 A US 3515504A
- Authority
- US
- United States
- Prior art keywords
- linear
- aromatic polyesters
- acid
- materials made
- textile material
- 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
- 239000000463 material Substances 0.000 title description 26
- 239000004753 textile Substances 0.000 title description 25
- 238000000034 method Methods 0.000 title description 18
- 125000003118 aryl group Chemical group 0.000 title description 8
- 229920000728 polyester Polymers 0.000 title description 8
- 238000010014 continuous dyeing Methods 0.000 title 1
- 230000008878 coupling Effects 0.000 description 12
- 238000010168 coupling process Methods 0.000 description 12
- 238000005859 coupling reaction Methods 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 10
- 239000000975 dye Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 238000004043 dyeing Methods 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- -1 aryl amide Chemical class 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 238000010025 steaming Methods 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- PZLGBVIKYPHZTH-UHFFFAOYSA-N ethene;2-nonylphenol Chemical group C=C.CCCCCCCCCC1=CC=CC=C1O PZLGBVIKYPHZTH-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ZMESHQOXZMOOQQ-UHFFFAOYSA-N 1-(naphthalen-1-ylmethyl)naphthalene Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 ZMESHQOXZMOOQQ-UHFFFAOYSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 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
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- LHRXTFDXJQAGAV-UHFFFAOYSA-L disodium 3-hydroxy-4-(naphthalen-1-yldiazenyl)naphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].Oc1c(cc2cc(ccc2c1N=Nc1cccc2ccccc12)S([O-])(=O)=O)S([O-])(=O)=O LHRXTFDXJQAGAV-UHFFFAOYSA-L 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000000080 wetting agent 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
- 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
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
- D06P3/56—Preparing azo dyes on the material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/042—Metal salts thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
- C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
-
- 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
- Y10S8/922—Polyester fiber
Definitions
- the expression textile material made from linear, aromatic polyesters used in this specification comprises more particularly fabrics made from polyethylene ter- 3,515,504 Patented June 2, 1970 ice ephthalate.
- the dyestuff components can be those used conventionally according to the methods hitherto known for the production of water-insoluble azo dyestuffs onto textile materials made from aromatic polyesters, Examples of diazotizable amines are l-aminol nitrobenzene, l-amino 2 methoxy-S-nitrobenzene, 4-amino-2'z3-dimethyl 1:1 azobenzene, 4:4-diamino-1:l'-phenylazonaphthalene, 4,4'-diamino-3:3-dirnethoxy-diphenyl and 4:4'-diamino-2:2', 5:5'-tetrachlorodiphenyl.
- coupling components there may be used for example 2-methoxyanilide, Z-methylanilide, 2:5-dimethoxyanilide or 2:4-dimethoxy-S-chloranilide of 2:3-hydroxynaphthoic acid and the 4-chloranilide of 2:3-hydroxycarbazolcarboxylic acid.
- the required fine distribution of the dyestutf components in water can be achieved in a per se conventional manner, for instance by means of wetting agents, dispersing agents and/or dissolving assistants, such as dinaphthylmethane disulfonic acid, dodecylbenzene sulfonic acid, nonylphenol-ethylene oxide-addition compounds, ethylene glycol monoethyl ether, dimethylformamide, methacrylic acid or polyvinyl lactames. It is also possible to add the usual auxiliary agents such as pH adjusting substances, to the aqueous solutions or dispersions respectively.
- wetting agents such as dinaphthylmethane disulfonic acid, dodecylbenzene sulfonic acid, nonylphenol-ethylene oxide-addition compounds, ethylene glycol monoethyl ether, dimethylformamide, methacrylic acid or polyvinyl lactames.
- auxiliary agents such as pH adjusting substances
- the impregnation of the textile material can be effected by passing the said material through the dye liquor, preferably at room temperature (about 15 to about 30 C.), and by squeezing the same for instance by means of a padding machine, the speed of the fabric ranging between about 10 to 15 meters/minute.
- the steaming or drying respectively is generally carried out at a temperature of about C., the textile material being treated in this way for 1 to 5 minutes. A steaming operation of about 2 minutes has proved to be particularly advantageous.
- the dry heating treatment is carried out at a temperature of to 230 C. for a period of generally 30 seconds to 3 minutes and advantageously of about 2 minutes.
- a developing bath of per se conventional composition e.g an aqueous solution of sodium nitrite and sulfuric acid.
- the development is advantageously carried out at about 50 to 100 C. It is a surprising fact that a period of only 1 to 5 and optionally of about 2 minutes is sufficient to cause a complete development. This surprising discovery also makes it possible to carry out the present process in a continuous manner. Finally the dyed textile material can be soaped and rinsed in the usual way and this also in a continuous manner.
- dyestuffs such as dispersion dyestuffs, which are stable against nitrous acid, can simultaneously be used beside the amines and coupling components yielding insoluble azo dyestuffs, when working according to the present invention.
- the present new method yields excellent results, if textile materials made from linear, aromatic polyesters and more particularly polyethylene terephthalate fabrics, are dyed in this way.
- the novel method has particularly the advantage that all operation steps can be carried out one after the other in a completely continuous manner and within a short time.
- the present novel method is extremely economical.
- it is unnecessary to make use of special pressure vessels, of organic solvents or swelling agents or so-called carriers respectively.
- a method for continuously dyeing textile materials made from linear, aromatic polyesters, While producing water-insoluble azo dyestulfs on the said textile material comprising impregnating the textile material with an aqueous dispersion of a diazotizable amine and of a coupling component, subjecting the textile material for a period of 1-5 minutes to drying, then subjecting it to a dry heating treatment for a period of 30 seconds to 3 minutes at a temperature between 140 C. and 230 C., and finally treating it for a period of 15 minutes at a temperature between C. and C. with an aqueous solution of sulphuric acid and an alkali nitrite to achieve diazotizing and coupling, all these operation steps being carried out in succession in a continuous manner.
- a method according to claim 2, wherein the diazotizable amine is selected from the group consisting of l-amino-4-nitrobenzene, 1 amino-Z-methoxy-S-nitrobenzene, 4-arnino 2':3 dimethyl-1:1-azobenzene, 4:4-diamino-1: l'-phenylazonaphthalene, 4,4 diamino-3 3-dimethoxy-diphenyl and 4:4'-diamino-2:2, 5:5-tetrachlorodiphenyl, and the coupling component is selected from the group consisting of 2-methoxyanilide, Z-methylanilide, 2:5-dimethoxyanilide and 2:4-dimethoxy-S-chloranilide of 2:3-hydroxynaphthoic acid and the 4-chloranilide of 2 :3 -hydroxycarbazolcarboxylic acid.
- a method according to claim 2, wherein the amine is 2-methoxyanilide of 2:3-hydroxynaphthoic acid and the coupling component is 4:4-diamino-l:1'-phenylazonaphthalene.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Description
United States Patent US. Cl. 846 Claims ABSTRACT OF THE DISCLOSURE Textile materials made from linear aromatic polyesters are continuously dyed, with production of water-insoluble azo dyes thereon, by impregnating the textile material with an aqueous dispersion of a diazotizable amine and of a coupling component, subjecting the textile material to steaming or drying, then subjecting it to a dry heating treatment at a temperature between 140 C. and 230 C., and finally treating it with an aqueous solution of an acid and a salt of nitrous acid, all these operation steps being carried out in succession in a continuous manner.
-It is known that it is possible to dye textile materials made from linear, aromatic polyesters while producing water-insoluble azo dyestuffs, if a diazotizable amine and a coupling component, such as an aniline derivative and an aryl amide of the 2:3-hydroxynaphthoic acid, are applied either simultaneously or separately and if the amine is subsequently diazotized on the textile material and coupled to form the azo dyestuff. Generally the application of the dyestutf components is carried out by an exhaust process, which consists in treating the textile material for about one hour at a temperature of about 100 C. or under pressure at high tempertaures, for instance at a temperature ranging from 120 to 130 C., in an aqueous dye bath containing the dyestutf components in a dissolved or microdispersed form. Moreover, methods enabling a continuous application of the dyestuif components are also well known. Thus it is possible to impregnate the textile material separately or simultaneously with both dyestuff components which have been dissolved in an organic solvent and to then subject the impregnated textile material to a drying or steaming operation. The development of the dyeing by diazotization and coupling takes place in all these cases in a discontinuous manner, for example by treating the fabric for a long period at elevated temperatures, eg for 30 minutes at 80 C., with an aqueous bath containing sodium nitrite and an acid.
It has now been found that textile materials made from linear, aromatic polyesters can be dyed in a continuous manner, while producing water-insoluble azo dyestutfs. This new method consists in impregnating the textile material with a diazotizable amine and a coupling component which are finely divided in water, whereupon the textile material is steamed or dried and then subjected to a dry heating treatment at a temperature ranging between 140 C. and 230 C., and is finally treated with an aqueous solution of an acid and a salt of nitrous acid, all these operation steps being carried out in a continuous manner.
The expression textile material made from linear, aromatic polyesters used in this specification comprises more particularly fabrics made from polyethylene ter- 3,515,504 Patented June 2, 1970 ice ephthalate. The dyestuff components can be those used conventionally according to the methods hitherto known for the production of water-insoluble azo dyestuffs onto textile materials made from aromatic polyesters, Examples of diazotizable amines are l-aminol nitrobenzene, l-amino 2 methoxy-S-nitrobenzene, 4-amino-2'z3-dimethyl 1:1 azobenzene, 4:4-diamino-1:l'-phenylazonaphthalene, 4,4'-diamino-3:3-dirnethoxy-diphenyl and 4:4'-diamino-2:2', 5:5'-tetrachlorodiphenyl. As coupling components there may be used for example 2-methoxyanilide, Z-methylanilide, 2:5-dimethoxyanilide or 2:4-dimethoxy-S-chloranilide of 2:3-hydroxynaphthoic acid and the 4-chloranilide of 2:3-hydroxycarbazolcarboxylic acid. The required fine distribution of the dyestutf components in water can be achieved in a per se conventional manner, for instance by means of wetting agents, dispersing agents and/or dissolving assistants, such as dinaphthylmethane disulfonic acid, dodecylbenzene sulfonic acid, nonylphenol-ethylene oxide-addition compounds, ethylene glycol monoethyl ether, dimethylformamide, methacrylic acid or polyvinyl lactames. It is also possible to add the usual auxiliary agents such as pH adjusting substances, to the aqueous solutions or dispersions respectively.
The impregnation of the textile material can be effected by passing the said material through the dye liquor, preferably at room temperature (about 15 to about 30 C.), and by squeezing the same for instance by means of a padding machine, the speed of the fabric ranging between about 10 to 15 meters/minute. The steaming or drying respectively is generally carried out at a temperature of about C., the textile material being treated in this way for 1 to 5 minutes. A steaming operation of about 2 minutes has proved to be particularly advantageous. The dry heating treatment is carried out at a temperature of to 230 C. for a period of generally 30 seconds to 3 minutes and advantageously of about 2 minutes. In order to eflect the diazotization and coupling, it is possible to use a developing bath of per se conventional composition, e.g an aqueous solution of sodium nitrite and sulfuric acid. The development is advantageously carried out at about 50 to 100 C. It is a surprising fact that a period of only 1 to 5 and optionally of about 2 minutes is sufficient to cause a complete development. This surprising discovery also makes it possible to carry out the present process in a continuous manner. Finally the dyed textile material can be soaped and rinsed in the usual way and this also in a continuous manner.
If desired, also other dyestuffs, such as dispersion dyestuffs, which are stable against nitrous acid, can simultaneously be used beside the amines and coupling components yielding insoluble azo dyestuffs, when working according to the present invention.
The present new method yields excellent results, if textile materials made from linear, aromatic polyesters and more particularly polyethylene terephthalate fabrics, are dyed in this way. Compared with the methods known up to now the novel method has particularly the advantage that all operation steps can be carried out one after the other in a completely continuous manner and within a short time. In view of these facts the present novel method is extremely economical. Moreover, according to the present invention, it is unnecessary to make use of special pressure vessels, of organic solvents or swelling agents or so-called carriers respectively. Furthermore-and this is a further advantage of the present methodno subsequent washing step, e.g. with sodium dithionite, is necessary, while such a subsequent washing operation is required in most methods known up to now.
The present invention will now be described in more detail in the following example without, however, being limited thereto.
EXAMPLE Well Washed polyethylene terephthalate piece goods are padded on the foulard at room temperature by means of a dye bath containing per 1000 parts of water 35 parts of the 2-methoxyanilide of 2:3-hydroxynaphthoic acid and 35 parts of 4:4-diamino-1:1'-phenylazonaphthalence, dispersed according to the disclosure given in Swiss Pat. No. 382,338, as well as 100 parts of urea, then they are squeezed, until the water content amounts to about 80%, and subsequently steamed for 2 minutes at a temperature of 102 C. Then the textile material is subjected to a dry heating treatment for 2 minutes at a temperature of 150 C. and treated for 2 minutes at a temperature ranging from 75 to 80 C. in a developing bath containing 18 parts of concentrated sulphuric acid and 4 parts of sodium nitrite dissolved in 1000 parts of water. Finally the textile material is soaped in a boiling bath containing per 1000 parts of water 2 parts of a nonylphenol-ethylene oxideaddition product and 1 part of sodium. carbonate and then rinsed. All Working steps are carried out in a continuous Way one after the other.
When Working in this way a deep, neutral black dyeing is produced. The quality of the dyeing is equal in any respect to dyeings produced according to known methods.
If, in the above example, the Z-methoxyanilide of the 2:3-hydroxynaphthoic acid and the 4:4-diamino-1:1'- phenylazonaphthalene are replaced by corresponding quantities of the Z-ethoxyanilide of 2:3-hydroxynaphthoic acid and 2:S-dimethyl-4-aminoazobenzene, deep Bordeaux red shades, having excellent fastness properties fully comparable with dyeings produced according to known methods are obtained.
What we claim is:
1. A method for continuously dyeing textile materials made from linear, aromatic polyesters, While producing water-insoluble azo dyestulfs on the said textile material comprising impregnating the textile material with an aqueous dispersion of a diazotizable amine and of a coupling component, subjecting the textile material for a period of 1-5 minutes to drying, then subjecting it to a dry heating treatment for a period of 30 seconds to 3 minutes at a temperature between 140 C. and 230 C., and finally treating it for a period of 15 minutes at a temperature between C. and C. with an aqueous solution of sulphuric acid and an alkali nitrite to achieve diazotizing and coupling, all these operation steps being carried out in succession in a continuous manner.
2. A method according to claim 1, wherein the textile material is made of polyethylene terephthalate.
3. A method according to claim 2, wherein the diazotizable amine is selected from the group consisting of l-amino-4-nitrobenzene, 1 amino-Z-methoxy-S-nitrobenzene, 4-arnino 2':3 dimethyl-1:1-azobenzene, 4:4-diamino-1: l'-phenylazonaphthalene, 4,4 diamino-3 3-dimethoxy-diphenyl and 4:4'-diamino-2:2, 5:5-tetrachlorodiphenyl, and the coupling component is selected from the group consisting of 2-methoxyanilide, Z-methylanilide, 2:5-dimethoxyanilide and 2:4-dimethoxy-S-chloranilide of 2:3-hydroxynaphthoic acid and the 4-chloranilide of 2 :3 -hydroxycarbazolcarboxylic acid.
4. A method according to claim 2, wherein the amine is 2-methoxyanilide of 2:3-hydroxynaphthoic acid and the coupling component is 4:4-diamino-l:1'-phenylazonaphthalene.
5. A method according to claim 2, wherein the amine is Z-ethoxyam'lide of 2:3-hydroxynaphthoic acid and the coupling component is 2:5-dimethyl-4-aminoazobenzene.
References Cited UNITED STATES PATENTS 2,088,506 7/1937 Chambers 845 FOREIGN PATENTS 382,338 11/1964 Switzerland.
GEORGE F. LESMES, Primary Examiner T. I. HERBERT 111., Assistant Examiner U.S. Cl. X.R.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1736466A CH466880A (en) | 1966-12-06 | 1966-12-06 | Process for the continuous dyeing of textile material made of linear, aromatic polyesters with the production of water-insoluble azo dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3515504A true US3515504A (en) | 1970-06-02 |
Family
ID=4424858
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US688005A Expired - Lifetime US3515504A (en) | 1966-12-06 | 1967-12-05 | Method for continuous dyeing of textile materials made from linear,aromatic polyesters |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3515504A (en) |
| CH (1) | CH466880A (en) |
| DE (1) | DE1619410A1 (en) |
| FR (1) | FR1549652A (en) |
| GB (1) | GB1198289A (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2088506A (en) * | 1934-04-06 | 1937-07-27 | Du Pont | Process and composition for applying and fixing diazoimino dyestuffs |
| CH382338A (en) * | 1963-02-22 | 1964-06-15 | Rohner Ag | Process for the production of water-insoluble azo dyes on textile structures made of linear aromatic polyesters, primarily polyethylene terephthalates |
-
1966
- 1966-12-06 CH CH1736466A patent/CH466880A/en unknown
-
1967
- 1967-11-29 DE DE19671619410 patent/DE1619410A1/en active Pending
- 1967-12-05 GB GB55218/67A patent/GB1198289A/en not_active Expired
- 1967-12-05 US US688005A patent/US3515504A/en not_active Expired - Lifetime
- 1967-12-06 FR FR1549652D patent/FR1549652A/fr not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2088506A (en) * | 1934-04-06 | 1937-07-27 | Du Pont | Process and composition for applying and fixing diazoimino dyestuffs |
| CH382338A (en) * | 1963-02-22 | 1964-06-15 | Rohner Ag | Process for the production of water-insoluble azo dyes on textile structures made of linear aromatic polyesters, primarily polyethylene terephthalates |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1549652A (en) | 1968-12-13 |
| DE1619410A1 (en) | 1971-07-08 |
| CH466880A (en) | 1968-06-28 |
| GB1198289A (en) | 1970-07-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3066005A (en) | Process for the treatment of hydroxyl group-containing textile materials | |
| US2317965A (en) | Process of coloring fibrous materials and the materials obtained thereby | |
| US2995412A (en) | Process for dyeing and printing of textile materials containing hydroxyl groups | |
| US3088790A (en) | Dyeings and prints possessing fastness to wet processing and their manufacture on cellulose material | |
| US3623834A (en) | Dye solution or print paste containing chlorinated hydrocarbon with an alcohol ketone dioxane alkanoic acid amide tetramethyl urea or pyridine and polyamide dyeing therewith | |
| US3363972A (en) | Process for dyeing and printing natural nitrogen-containing fibrous materials | |
| US3288551A (en) | Process for the coloring of fiber blends of polyester and native or regenerated cellulose | |
| US3524718A (en) | Processes for the continuous dyeing and printing of cellulose ester fiber material | |
| US3515504A (en) | Method for continuous dyeing of textile materials made from linear,aromatic polyesters | |
| US3576589A (en) | Method for thermofixation dyeing of polyester/cotton fabric in a mixture of vat/disperse dye | |
| CH485360A (en) | Small-sized single-phase synchronous electric motor | |
| US3802837A (en) | Polyamide dyeing with a reaction product of a reactive dye-n-alkylamine alkyl carboxylic or sulfonic acid or salt thereof | |
| Abou Elmaaty et al. | Development of textile dyeing using the green supercritical fluid technology: A Review | |
| US3787179A (en) | Process for the manufacture of insoluble azo dyestuffs on cellulose fibers | |
| US4062645A (en) | Acid dyes useful for dyeing streaked nylon | |
| GB758745A (en) | Process for improving properties of fibres, films or sheets made of synthetic thermoplastic material | |
| US3249394A (en) | Vat dyeing with thiosulfate dyes | |
| US3811836A (en) | Continuous dyeing of synthetic textile fibres with a basic character | |
| US3325242A (en) | Process for dyeing and printing with reactive dyestuffs | |
| US3795481A (en) | Process for the single-bath dyeing of cellulose and polyamide fiber blends according to the pad dyeing technique | |
| US3679350A (en) | Process for the dyeing of textile materials made from mixtures of polyester and cellulosic fibres | |
| US3708257A (en) | Process for the dyeing of textile material made from mixtures of polyester and cellulosic fibers | |
| US3110541A (en) | Process for dyeing and printing cellu- | |
| US2956853A (en) | Mordant dyeing process | |
| US3473883A (en) | Process for dyeing and printing polyester materials |