Process for dyeing synthetic fibers employing naphthyl dye assistants
United States Patent 3893805
Synthetic fibers are dyed with a disperse dyestuff and a carrier of the following formula: ##SPC1## Wherein Y is lower ester, ether or acyl and Z is lower alkyl, alkoxy or halogen. Preferred dye assistants include naphthyl carbonic acid esters.
US Patent References:
Vat dye composition
Kern - August 1940 - 2211126
Method of dyeing synthetic fibrous materials
Mecco - April 1959 - 2881045
COAL TAR METHYL NAPHTHALENE FRACTION AND DIPHENYL CARRIER AND DYEING THEREWITH
Britt - November 1971 - 3617213
Vat dye composition
Kern - August 1940 - 2211126
Method of dyeing synthetic fibrous materials
Mecco - April 1959 - 2881045
COAL TAR METHYL NAPHTHALENE FRACTION AND DIPHENYL CARRIER AND DYEING THEREWITH
Britt - November 1971 - 3617213
Inventors:
Dellian, Kurt A. (Ossining, NY)
Lee, Samuel (Fairlawn, NJ)
Lee, Samuel (Fairlawn, NJ)
Application Number:
05/326921
Publication Date:
07/08/1975
Filing Date:
01/26/1973
View Patent Images:
Export Citation:
Assignee:
Ciba-Geigy Corporation (Ardsley, NY)
Primary Class:
Other Classes:
8/618, 8/540, 8/532, 8/539, 8/534, 8/531
International Classes:
D06P1/651; D06P3/52; D06P3/54; D06P3/82; D06P1/64; D06P3/34; D06P1/68
Field of Search:
8/173,174,92,21C
Primary Examiner:
Padgett, Benjamin R.
Assistant Examiner:
Hunt B. H.
Attorney, Agent or Firm:
Kolodny I, Joseph Roberts Edward Mcc Almaula Prabodh G.
Claims:
Wherefore we claim
1. A process for dyeing synthetic hydrophobic fibers or fabric comprising treating said fibers with a mixture of a disperse dyestuff and a carrier which is a naphthyl carbonic acid ester of the formula ##SPC10## wherein R1 is C1 -C4 -alkyl, benzyl or phenyl; Z is halogen or C1 -C4 -alkyl; n is 0 or 1 and b is 0, 1 or 2; and said benzyl and phenyl each have from 0-2 Z radicals substituted thereon.
2. A process for dyeing polyester fibers or fabric in a dyebath which comprises a mixture of a disperse dyestuff and a carrier of the formula ##SPC11##
3. The process of claim 2 wherein the carrier is added to the dyebath in the form of an emulsion which comprises the carrier, from 3-20% by weight of carrier of an emulsifier and water.
4. The process in accordance with claim 2 wherein the dyebath contains from about 1-15% by weight of carrier based on the weight of the fabric to be dyed.
1. A process for dyeing synthetic hydrophobic fibers or fabric comprising treating said fibers with a mixture of a disperse dyestuff and a carrier which is a naphthyl carbonic acid ester of the formula ##SPC10## wherein R1 is C1 -C4 -alkyl, benzyl or phenyl; Z is halogen or C1 -C4 -alkyl; n is 0 or 1 and b is 0, 1 or 2; and said benzyl and phenyl each have from 0-2 Z radicals substituted thereon.
2. A process for dyeing polyester fibers or fabric in a dyebath which comprises a mixture of a disperse dyestuff and a carrier of the formula ##SPC11##
3. The process of claim 2 wherein the carrier is added to the dyebath in the form of an emulsion which comprises the carrier, from 3-20% by weight of carrier of an emulsifier and water.
4. The process in accordance with claim 2 wherein the dyebath contains from about 1-15% by weight of carrier based on the weight of the fabric to be dyed.
Description:
BACKGROUND OF THE INVENTION
The present invention is directed to a process for dyeing and/or printing a hydrophobic textile material, particularly polyesters or cellulose triacetate. In particular, it relates to a dyeing process employing a dyeing assistant which is substantially non-polluting and biodegradable.
Previously, in the dyeing or printing of textile fibers employing an organic dyestuff of negligible water-solubility, it was necessary to employ elevated pressures and temperatures beyond about 250°F. To overcome these costly and complex dyeing techniques, specific carrier components were added to the dyebaths. The carriers are compounds which are capable of swelling the fibrous textile material or otherwise affecting the fiber and thus facilitating the penetration of the dyestuff into the fiber. Conventionally, the use of such carriers and dyebaths for hydrophobic fibers permits satisfactory dyeing at temperatures as low as 200°-210°F and permits the use of unpressurized equipment.
Conventionally preferred dye carriers included chlorinated hydrocarbons, for example chlorinated benzene. Additionally other carriers, such as derivatives of benzene or phenol, such as ortho- or para-phenylphenol, benzyl alcohol, benzene carbonic esters or ethers and benzoic or salicylic acid have been employed.
While the performance of the prior art carriers has been generally satisfactory with regard to assisting in dye penetration nevertheless the carriers do possess numerous substantial undesirable ecological properties. Such undesired properties included unacceptable toxicity, non-biodegradableness and undue odoriferousness. Apart from the ecologically undesired side effects of the carriers, certain assistants produce variations in shade in the textile and also adversely effect the fastness of the dye.
Accordingly, it is a principal object of the present invention to provide a process for dyeing hydrophobic fibers in the presence of an ecologically acceptable dye carrier.
It is another object to the invention to provide a substantially non-polluting, low odor, low-toxic dye carrier which does not produce undesired variations in shade or dye fastness on a hydrophobic textile fiber.
The above and other objects are met in a process for coloring synthetic hydrophobic fibers, or fabric with a dispersed dyestuff in a carrier of the following general formula: ##SPC2##
Wherein n=O to 2; a=1 or 2; b=0 to 2; Z is a radical which includes C 1 -C 4 -alkyl, halogen and C 1 -C 3 -alkoxy; Y is --COOR; --OR; --OCOCH 3 and --OCOC 2 H 5 and R is a radical which includes C 1 -C 4 -alkyl, phenyl, benzyl and C 4 -C 6 -cycloalkyl; wherein when n=0, Y is not --OR, said phenyl and benzyl radicals each having from 0-2 Z groups substituted thereon.
The dye assistants of the present process have been found to be of low odor, low toxicity and substantially biodegradable. From an environmental standpoint, these properties are extremely valuable. In addition to being ecologically desirable, the carriers also permit an efficient drawing rate for the dyestuff and aid in permitting good fastness with uniform shade in the dyeing operation.
As employed herein, the term "disperse dyestuff" refers to organic colored compounds which are at most only slightly water-soluble. Conventionally, these disperse dyestuffs are applied in the form of aqueous dispersions well known to those skilled in the art. The disperse dyestuffs employed are well known and may be the typical azo and amino anthraquinone dyes, as set forth in the Color Index (C.I.) for Disperse Dyes.
The hydrophobic textile materials that may be dyed according to the present process include fibers of polyamide, polyacrylate, modacrylate polyester and preferably cationic modified polyester and cellulose triacetate. Typical cationic modified polyester fibers are derived from high melting linear polyethylene glycol terephthalate and include the fibers commercially available under the following trademarks: TERYLENE, DACRON, TERGAL, DIOLEN or TREVIRA. Typical commercially available cellulose triacetate fibers include those identified by the marks ARNEL, TRICEL and COURPLETA. Blends and mixes of the aforesaid fibers may also be dyed employing the present ecologically desired dye assistants.
Typical dye carriers which are environmentally acceptable include: ##SPC3##
Description of Preferred Embodiments
For maximum effectiveness in the dyebath, the preferred carriers melt below about 100°C. Further, the carriers and their substituents must be substantially non-toxic, non-odoriferous and biodegradable. Accordingly, the preferred carriers employed in the dyeing process include naphthyl carbonic acid esters of the formula: ##SPC4##
wherein R 1 is C 1 -C 4 -alkyl, benzyl or phenyl; Z is halogen or C 1 -C 4 -alkyl; n is 0 or 1 and b is 0, 1 or 2. The particularly preferred halogen substituent is chlorine.
The preferred R 1 groups have been found to be particularly ecologically desirable having substantially no odor and low toxicity in the carrier compounds.
In general, it is preferred that the lower alkyl and halogen constituents on the naphthyl esters if present generally be limited to a total of not more than one on each of the ring members.
Particularly preferred ecologically desirable carriers include α-methyl naphthoate; α-benzyl naphthoate; β-ethyl naphthoate; methly-α-naphthyl acetate; α-phenylnaphthoate and chlorophenyl-naphthyl acetate.
The benzyl and phenyl R 1 and R groups may have substituted thereon up to three C 1 -C 3 -alkyl and/or halogen groups. Preferably, if present at all, a single halogen or lower alkyl group will be present on the phenyl or benzyl ring.
It has been found that when other functional substituents are present on the preferred naphthyl carbonic acid ester carriers, certain undesirable environmental problems can arise. For example, aldehyde or ketone substituents substituents tend to be undesirably odoriferous. Amido groups generally raise the melting point of the carrier above about 100° and render more difficult the aqueous dyeing process which is usually run at atmospheric pressures.
In general, the carriers are dissolved, dispersed or emulsified in a dyebath according to conventional procedures. It is preferred that the carrier be emulsified, since the preferred ecologically desirable carriers are water-insoluble. The carrier may be conventionally emulsified by pre-mixing the carrier with the emulsifier and thereafter forming an emulsion in the dyebath. Alternatively, the carrier can be dissolved in a solvent, such as an alcohol, and then added to the dyebath which contains a suitable emulsifier. Examples of particularly useful emulsifiers include oxethylated sulfonates, alkylarylphenols or sulfates of higher fatty acids. Other useful emulsifiers include polyglycol ethers derived from condensation of ethylene oxide and higher fatty alcohols, alkylphenols or fatty amines. Preferred emulsifiers include salts of sulfonated detergents as sulfonated benzimidazoles substituted by higher alkyl radicals at the second carbon atom; salts of monocarboxylic acid esters of 4-sulfophthalic acid with higher fatty alcohols; salts of fatty alcohol sufonates, alkylaryl sulfonic acids or condensation products of higher fatty acids with aliphatic hydroxysulfonic or aminosulfonic acids.
Although the amount of emulsifier which may be employed may be widely varied, it is generally preferred for practicality and efficiency to employ from about 3 to 20% of emulsifier based on the weight of carrier. Over 20% emulsifier by weight of carrier tend to be unduly excessive, while amounts under about 3% tend to be insufficient to bring the insoluble carriers into a stable emulsion.
It is a significant feature of the invention that the preferred naphthyl carbonic acid ester carriers are stable both under acid and alkaline conditions and do not undergo decomposition during the dyeing or printing process. These properties are in addition to the environmentally preferred properties of substantial non-toxicity, biodegradableness and non-odoriferous. Additionally, the esters do not undesirably influence the light fastness in dyeing processes as contrasted with other conventional prior art carriers such as ortho-phenyl-phenol.
The naphthoic ether carriers of the present invention can be formed from conventional procedures such as reacting an α- or β-haloalkylene naphthalene such as α- or β-chloromethylnaphthalene with sodium ethoxide, thereby forming an ethyl alkylnaphthyl ether, such as ethyl methylenenaphthyl ether. The preferred naphthyl carbinol ester carriers can be formed by reacting a suitable α- or β-haloalkylnaphthalene such as α- or β-chloroalkylnaphthalene with a potassium salt of a lower molecular weight methyl carboxylic acid, such as acetic acid, to form a naphthyl carbinol ester, such as methyl-α-naphthyl acetate. To form the particularly preferred naphthoic acid esters, an α,β-naphthoic acid may be condensed according to conventional procedures with the desired alcohol.
The concentration of the carrier in the dyebath may vary between relatively broad ranges. It is preferable that from about 1 to 15% carrier by weight of textile goods (fabric) is employed. When the concentration of the carrier rises above about 15%, a competing reaction occurs which tends to strip the fiber simultaneously as the fiber is dyed. Below about 1% by weight, the carrier concentration is insufficient to significantly penetrate and swell the fibrous material to permit penetration of the dyestuff into the fiber.
Enhanced dyeing is obtained and consequently it is particularly preferred that from about 2 to 8% by weight of carrier is employed based on the weight of the textile goods. Of course, the particular optimum concentration of carrier will depend in part on the type of disperse dye employed, the fiber to be dyed and the technique of application.
In general, the dyeing process may be employed with any of the conventional disperse dyestuffs known to the art. As illustrative of suitable disperse dyes are Color Index--C.I.--Disperse Dyes. Typical azo disperse dyes are Cibacet Orange 2R (C.I. Disperse Orange 3) No. 11005 and Disperse Fast Yellow G (C.I. Disperse Yellow 3) No. 11855 . Typical anthraquinone dyes are exemplified by C.I. Disperse Violet 8 No. 62030 and C.I. Disperse Blue 1. Examples of other disperse dyes include C.I. Disperse Yellow 4; Disperse Yellow 1 No. 10345; Disperse Orange 13 No. 20080; Disperse Orange 3 No. 11005; Disperse Yellow 3 No. 11855; Disperse Orange 1 No. 11080; Disperse Red 19; Disperse Red 1 No. 1110; Disperse Red 13 No. 11115; Disperse Red 11 No. 62015; Disperse Violet 14; Disperse Blue 14 and Disperse Blue 24. Other suitable dyes include dispersible vat dyes such as C.I. Vat Red 41 No. 73300 and C.I. Vat Blue 1 No. 73000.
The present treatment utilizing the naphthyl compounds as carriers is usually employed in atmospheric dyeing processes carried out at temperatures up to about the boiling point of water. If desired, the present process may be carried out as a pressurized dyeing process wherein the dyebath is under a pressure of from about 3 to 4 atmospheres in a closed container at temperatures up to about 135°C.
If desired, other well-known conventional constituents may be added to the dyebath such as thickeners, anti-foaming agents, and the like. Other conventional organic carriers may be admixed with the naphthyl carriers in minor proportions. However, these carriers will reduce the ecologically desirable properties of the present process to some degree. The present process is useful for both dyeing and printing applications.
In the following examples, the disperse dyes are brought into a state of suspension in the dyebath employing conventional procedures. For example, the dye can be stirred with 10 to 20 times its weight of water at 50° to 60°C and allowed to stand for 10 minutes with occasional agitation. Before adding the disperse dyestuff to the dye liquor a conventional synthetic dispersing agent is put into the liquor to assist in maintaining a stable suspension and increase the dispersability of the dye pigment in water.
The following examples illustrate certain preferred embodiments of the invention and are not limitative of scope.
EXAMPLE 1
An emulsion of the following composition was formed:
70 parts α- methylnaphthoate
10 parts sodium salt of sulfonated oleic acid amylester
20 parts water
An aqueous dyebath was formed containing the pre-formed emulsion and 3% by weight of fabric to be treated of the dyestuff of the formula: ##SPC5##
as taught in Chemical Abstract, Vol. 74, Abstract No. 10056(K).
The liquid content of the dyebath was adjusted to provide a liquor to fabric weight ratio of 30:1. Next a polyester fabric formed from cationic modified polyethylene terephthalate was introduced into the aqueous dyebath.
The dyebath was raised to boiling and kept at the boil for 2 hours. Thereafter the fabric was rinsed and soaked. Next the fabric was subjected to an after-treatment bath containing 4 ml/l caustic soda, 38% Be and 5 g/l sodium hydrosulfite at 80°C for 20 minutes. A deep red shade of very good fastness was obtained. Similar results are obtained employing any of the following dye carriers which are substituted for the α-methylnaphthoate: ##SPC6##
EXAMPLE 2
An aqueous dyebath was formed containing 8% by weight of an emulsion consisting of
65% by weight of the total emulsion of α-benzylnaphthoate
15% by weight of the emulsion of the ammonium salt of oxethylated nonylphenol sulfate
20% by weight of the emulsion of water
A dyestuff of the formula: ##SPC7##
was added to the aqueous dyebath in an amount equal to 2.5% by weight of the dyebath. A polyethylene terephthalic fabric (polyester) was dyed in the dyebath wherein the dye liquor to fabric weight ratio was 40:1.
The dyebath was raised to the boil and kept there at from about 90 minutes. Thereafter the fabric was rinsed and soaped. A deep yellow shade was obtained with good all-round fastness.
EXAMPLE 3
A polyester fabric was dyed in accordance with the procedure set forth in Example 1 with the exception that the dyestuff was replaced by an equal weight of: ##SPC8##
A reddish blue shade of good all-round fastness was obtained.
EXAMPLE 4
A polyester fabric was dyed in accordance with the procedure set forth in Example 1 with the exception that an 8% emulsion containing 70% by weight of the emulsion of β-ethylnaphthoate was employed. A deep red shade of very good fastness was obtained.
EXAMPLE 5
A polyethylene terephthalate fabric (polyester) was dyed in accordance with the procedure set forth in Example 1 with the exception that a mixture of 1% by weight of the dyestuff of Example 1 and Example 2 were employed. An orange shade of generally good fastness was obtained.
EXAMPLE 6
A polyethylene terephthalate fabric was dyed in accordance with the procedure set forth in Example 2 with the exception that an 8% by weight of emulsion containing 65% by weight of the emulsion of methyl-α-naphthyl acetate was employed. A deep yellow shade with good all-round fastness was obtained.
EXAMPLE 7
A polyethylene terephthalate fabric was printed with a print paste. The paste contained 20 g/k of the dyestuff employed in Example 1, 50 g/k of α-phenylnaphthoate and a thickener of starch ether-locust bean gum. The print was submitted to a 2-minute curing at 320°F. A fast red shade was obtained.
EXAMPLE 8
A blend of polyethylene terephthalate (Dacron 54) fibers and anionic modified polyethylene terephthalate (Dacron 64) was dyed in an aqueous dyebath according to Example 1 with a liquor to fabric weight ratio of 40:1. The bath contained 8 parts of an emulsion of 85 parts of chlorophenyl naphthylacetate and 15 parts of polyoxethylated phenol emulsifier. The aqueous dyebath also contained 1% of the dyestuff employed in Example 1 and 1% of the following dyestuff: ##SPC9##
C.I. -- BASIC YELLOW B
A uniform yellow shade was obtained with good fastness properties.
It will be obvious to those skilled in the art that other carriers, dyestuffs and emulsifiers can be employed without departing from the spirit of the invention. Other modifications with regard to treatment steps, temperatures and other reaction parameters will be obvious to those skilled in the art. While certain preferred embodiments are disclosed herein, the invention is not to be limited except as set forth in the following claims:
The present invention is directed to a process for dyeing and/or printing a hydrophobic textile material, particularly polyesters or cellulose triacetate. In particular, it relates to a dyeing process employing a dyeing assistant which is substantially non-polluting and biodegradable.
Previously, in the dyeing or printing of textile fibers employing an organic dyestuff of negligible water-solubility, it was necessary to employ elevated pressures and temperatures beyond about 250°F. To overcome these costly and complex dyeing techniques, specific carrier components were added to the dyebaths. The carriers are compounds which are capable of swelling the fibrous textile material or otherwise affecting the fiber and thus facilitating the penetration of the dyestuff into the fiber. Conventionally, the use of such carriers and dyebaths for hydrophobic fibers permits satisfactory dyeing at temperatures as low as 200°-210°F and permits the use of unpressurized equipment.
Conventionally preferred dye carriers included chlorinated hydrocarbons, for example chlorinated benzene. Additionally other carriers, such as derivatives of benzene or phenol, such as ortho- or para-phenylphenol, benzyl alcohol, benzene carbonic esters or ethers and benzoic or salicylic acid have been employed.
While the performance of the prior art carriers has been generally satisfactory with regard to assisting in dye penetration nevertheless the carriers do possess numerous substantial undesirable ecological properties. Such undesired properties included unacceptable toxicity, non-biodegradableness and undue odoriferousness. Apart from the ecologically undesired side effects of the carriers, certain assistants produce variations in shade in the textile and also adversely effect the fastness of the dye.
Accordingly, it is a principal object of the present invention to provide a process for dyeing hydrophobic fibers in the presence of an ecologically acceptable dye carrier.
It is another object to the invention to provide a substantially non-polluting, low odor, low-toxic dye carrier which does not produce undesired variations in shade or dye fastness on a hydrophobic textile fiber.
The above and other objects are met in a process for coloring synthetic hydrophobic fibers, or fabric with a dispersed dyestuff in a carrier of the following general formula: ##SPC2##
Wherein n=O to 2; a=1 or 2; b=0 to 2; Z is a radical which includes C 1 -C 4 -alkyl, halogen and C 1 -C 3 -alkoxy; Y is --COOR; --OR; --OCOCH 3 and --OCOC 2 H 5 and R is a radical which includes C 1 -C 4 -alkyl, phenyl, benzyl and C 4 -C 6 -cycloalkyl; wherein when n=0, Y is not --OR, said phenyl and benzyl radicals each having from 0-2 Z groups substituted thereon.
The dye assistants of the present process have been found to be of low odor, low toxicity and substantially biodegradable. From an environmental standpoint, these properties are extremely valuable. In addition to being ecologically desirable, the carriers also permit an efficient drawing rate for the dyestuff and aid in permitting good fastness with uniform shade in the dyeing operation.
As employed herein, the term "disperse dyestuff" refers to organic colored compounds which are at most only slightly water-soluble. Conventionally, these disperse dyestuffs are applied in the form of aqueous dispersions well known to those skilled in the art. The disperse dyestuffs employed are well known and may be the typical azo and amino anthraquinone dyes, as set forth in the Color Index (C.I.) for Disperse Dyes.
The hydrophobic textile materials that may be dyed according to the present process include fibers of polyamide, polyacrylate, modacrylate polyester and preferably cationic modified polyester and cellulose triacetate. Typical cationic modified polyester fibers are derived from high melting linear polyethylene glycol terephthalate and include the fibers commercially available under the following trademarks: TERYLENE, DACRON, TERGAL, DIOLEN or TREVIRA. Typical commercially available cellulose triacetate fibers include those identified by the marks ARNEL, TRICEL and COURPLETA. Blends and mixes of the aforesaid fibers may also be dyed employing the present ecologically desired dye assistants.
Typical dye carriers which are environmentally acceptable include: ##SPC3##
Description of Preferred Embodiments
For maximum effectiveness in the dyebath, the preferred carriers melt below about 100°C. Further, the carriers and their substituents must be substantially non-toxic, non-odoriferous and biodegradable. Accordingly, the preferred carriers employed in the dyeing process include naphthyl carbonic acid esters of the formula: ##SPC4##
wherein R 1 is C 1 -C 4 -alkyl, benzyl or phenyl; Z is halogen or C 1 -C 4 -alkyl; n is 0 or 1 and b is 0, 1 or 2. The particularly preferred halogen substituent is chlorine.
The preferred R 1 groups have been found to be particularly ecologically desirable having substantially no odor and low toxicity in the carrier compounds.
In general, it is preferred that the lower alkyl and halogen constituents on the naphthyl esters if present generally be limited to a total of not more than one on each of the ring members.
Particularly preferred ecologically desirable carriers include α-methyl naphthoate; α-benzyl naphthoate; β-ethyl naphthoate; methly-α-naphthyl acetate; α-phenylnaphthoate and chlorophenyl-naphthyl acetate.
The benzyl and phenyl R 1 and R groups may have substituted thereon up to three C 1 -C 3 -alkyl and/or halogen groups. Preferably, if present at all, a single halogen or lower alkyl group will be present on the phenyl or benzyl ring.
It has been found that when other functional substituents are present on the preferred naphthyl carbonic acid ester carriers, certain undesirable environmental problems can arise. For example, aldehyde or ketone substituents substituents tend to be undesirably odoriferous. Amido groups generally raise the melting point of the carrier above about 100° and render more difficult the aqueous dyeing process which is usually run at atmospheric pressures.
In general, the carriers are dissolved, dispersed or emulsified in a dyebath according to conventional procedures. It is preferred that the carrier be emulsified, since the preferred ecologically desirable carriers are water-insoluble. The carrier may be conventionally emulsified by pre-mixing the carrier with the emulsifier and thereafter forming an emulsion in the dyebath. Alternatively, the carrier can be dissolved in a solvent, such as an alcohol, and then added to the dyebath which contains a suitable emulsifier. Examples of particularly useful emulsifiers include oxethylated sulfonates, alkylarylphenols or sulfates of higher fatty acids. Other useful emulsifiers include polyglycol ethers derived from condensation of ethylene oxide and higher fatty alcohols, alkylphenols or fatty amines. Preferred emulsifiers include salts of sulfonated detergents as sulfonated benzimidazoles substituted by higher alkyl radicals at the second carbon atom; salts of monocarboxylic acid esters of 4-sulfophthalic acid with higher fatty alcohols; salts of fatty alcohol sufonates, alkylaryl sulfonic acids or condensation products of higher fatty acids with aliphatic hydroxysulfonic or aminosulfonic acids.
Although the amount of emulsifier which may be employed may be widely varied, it is generally preferred for practicality and efficiency to employ from about 3 to 20% of emulsifier based on the weight of carrier. Over 20% emulsifier by weight of carrier tend to be unduly excessive, while amounts under about 3% tend to be insufficient to bring the insoluble carriers into a stable emulsion.
It is a significant feature of the invention that the preferred naphthyl carbonic acid ester carriers are stable both under acid and alkaline conditions and do not undergo decomposition during the dyeing or printing process. These properties are in addition to the environmentally preferred properties of substantial non-toxicity, biodegradableness and non-odoriferous. Additionally, the esters do not undesirably influence the light fastness in dyeing processes as contrasted with other conventional prior art carriers such as ortho-phenyl-phenol.
The naphthoic ether carriers of the present invention can be formed from conventional procedures such as reacting an α- or β-haloalkylene naphthalene such as α- or β-chloromethylnaphthalene with sodium ethoxide, thereby forming an ethyl alkylnaphthyl ether, such as ethyl methylenenaphthyl ether. The preferred naphthyl carbinol ester carriers can be formed by reacting a suitable α- or β-haloalkylnaphthalene such as α- or β-chloroalkylnaphthalene with a potassium salt of a lower molecular weight methyl carboxylic acid, such as acetic acid, to form a naphthyl carbinol ester, such as methyl-α-naphthyl acetate. To form the particularly preferred naphthoic acid esters, an α,β-naphthoic acid may be condensed according to conventional procedures with the desired alcohol.
The concentration of the carrier in the dyebath may vary between relatively broad ranges. It is preferable that from about 1 to 15% carrier by weight of textile goods (fabric) is employed. When the concentration of the carrier rises above about 15%, a competing reaction occurs which tends to strip the fiber simultaneously as the fiber is dyed. Below about 1% by weight, the carrier concentration is insufficient to significantly penetrate and swell the fibrous material to permit penetration of the dyestuff into the fiber.
Enhanced dyeing is obtained and consequently it is particularly preferred that from about 2 to 8% by weight of carrier is employed based on the weight of the textile goods. Of course, the particular optimum concentration of carrier will depend in part on the type of disperse dye employed, the fiber to be dyed and the technique of application.
In general, the dyeing process may be employed with any of the conventional disperse dyestuffs known to the art. As illustrative of suitable disperse dyes are Color Index--C.I.--Disperse Dyes. Typical azo disperse dyes are Cibacet Orange 2R (C.I. Disperse Orange 3) No. 11005 and Disperse Fast Yellow G (C.I. Disperse Yellow 3) No. 11855 . Typical anthraquinone dyes are exemplified by C.I. Disperse Violet 8 No. 62030 and C.I. Disperse Blue 1. Examples of other disperse dyes include C.I. Disperse Yellow 4; Disperse Yellow 1 No. 10345; Disperse Orange 13 No. 20080; Disperse Orange 3 No. 11005; Disperse Yellow 3 No. 11855; Disperse Orange 1 No. 11080; Disperse Red 19; Disperse Red 1 No. 1110; Disperse Red 13 No. 11115; Disperse Red 11 No. 62015; Disperse Violet 14; Disperse Blue 14 and Disperse Blue 24. Other suitable dyes include dispersible vat dyes such as C.I. Vat Red 41 No. 73300 and C.I. Vat Blue 1 No. 73000.
The present treatment utilizing the naphthyl compounds as carriers is usually employed in atmospheric dyeing processes carried out at temperatures up to about the boiling point of water. If desired, the present process may be carried out as a pressurized dyeing process wherein the dyebath is under a pressure of from about 3 to 4 atmospheres in a closed container at temperatures up to about 135°C.
If desired, other well-known conventional constituents may be added to the dyebath such as thickeners, anti-foaming agents, and the like. Other conventional organic carriers may be admixed with the naphthyl carriers in minor proportions. However, these carriers will reduce the ecologically desirable properties of the present process to some degree. The present process is useful for both dyeing and printing applications.
In the following examples, the disperse dyes are brought into a state of suspension in the dyebath employing conventional procedures. For example, the dye can be stirred with 10 to 20 times its weight of water at 50° to 60°C and allowed to stand for 10 minutes with occasional agitation. Before adding the disperse dyestuff to the dye liquor a conventional synthetic dispersing agent is put into the liquor to assist in maintaining a stable suspension and increase the dispersability of the dye pigment in water.
The following examples illustrate certain preferred embodiments of the invention and are not limitative of scope.
EXAMPLE 1
An emulsion of the following composition was formed:
70 parts α- methylnaphthoate
10 parts sodium salt of sulfonated oleic acid amylester
20 parts water
An aqueous dyebath was formed containing the pre-formed emulsion and 3% by weight of fabric to be treated of the dyestuff of the formula: ##SPC5##
as taught in Chemical Abstract, Vol. 74, Abstract No. 10056(K).
The liquid content of the dyebath was adjusted to provide a liquor to fabric weight ratio of 30:1. Next a polyester fabric formed from cationic modified polyethylene terephthalate was introduced into the aqueous dyebath.
The dyebath was raised to boiling and kept at the boil for 2 hours. Thereafter the fabric was rinsed and soaked. Next the fabric was subjected to an after-treatment bath containing 4 ml/l caustic soda, 38% Be and 5 g/l sodium hydrosulfite at 80°C for 20 minutes. A deep red shade of very good fastness was obtained. Similar results are obtained employing any of the following dye carriers which are substituted for the α-methylnaphthoate: ##SPC6##
EXAMPLE 2
An aqueous dyebath was formed containing 8% by weight of an emulsion consisting of
65% by weight of the total emulsion of α-benzylnaphthoate
15% by weight of the emulsion of the ammonium salt of oxethylated nonylphenol sulfate
20% by weight of the emulsion of water
A dyestuff of the formula: ##SPC7##
was added to the aqueous dyebath in an amount equal to 2.5% by weight of the dyebath. A polyethylene terephthalic fabric (polyester) was dyed in the dyebath wherein the dye liquor to fabric weight ratio was 40:1.
The dyebath was raised to the boil and kept there at from about 90 minutes. Thereafter the fabric was rinsed and soaped. A deep yellow shade was obtained with good all-round fastness.
EXAMPLE 3
A polyester fabric was dyed in accordance with the procedure set forth in Example 1 with the exception that the dyestuff was replaced by an equal weight of: ##SPC8##
A reddish blue shade of good all-round fastness was obtained.
EXAMPLE 4
A polyester fabric was dyed in accordance with the procedure set forth in Example 1 with the exception that an 8% emulsion containing 70% by weight of the emulsion of β-ethylnaphthoate was employed. A deep red shade of very good fastness was obtained.
EXAMPLE 5
A polyethylene terephthalate fabric (polyester) was dyed in accordance with the procedure set forth in Example 1 with the exception that a mixture of 1% by weight of the dyestuff of Example 1 and Example 2 were employed. An orange shade of generally good fastness was obtained.
EXAMPLE 6
A polyethylene terephthalate fabric was dyed in accordance with the procedure set forth in Example 2 with the exception that an 8% by weight of emulsion containing 65% by weight of the emulsion of methyl-α-naphthyl acetate was employed. A deep yellow shade with good all-round fastness was obtained.
EXAMPLE 7
A polyethylene terephthalate fabric was printed with a print paste. The paste contained 20 g/k of the dyestuff employed in Example 1, 50 g/k of α-phenylnaphthoate and a thickener of starch ether-locust bean gum. The print was submitted to a 2-minute curing at 320°F. A fast red shade was obtained.
EXAMPLE 8
A blend of polyethylene terephthalate (Dacron 54) fibers and anionic modified polyethylene terephthalate (Dacron 64) was dyed in an aqueous dyebath according to Example 1 with a liquor to fabric weight ratio of 40:1. The bath contained 8 parts of an emulsion of 85 parts of chlorophenyl naphthylacetate and 15 parts of polyoxethylated phenol emulsifier. The aqueous dyebath also contained 1% of the dyestuff employed in Example 1 and 1% of the following dyestuff: ##SPC9##
C.I. -- BASIC YELLOW B
A uniform yellow shade was obtained with good fastness properties.
It will be obvious to those skilled in the art that other carriers, dyestuffs and emulsifiers can be employed without departing from the spirit of the invention. Other modifications with regard to treatment steps, temperatures and other reaction parameters will be obvious to those skilled in the art. While certain preferred embodiments are disclosed herein, the invention is not to be limited except as set forth in the following claims: