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
  • 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
• • 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
  • D06P1/65131—Compounds containing ether or acetal groups
• • 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
  • D06P3/522—Polyesters using basic dyes
• • 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
  • D06P3/54—Polyesters using dispersed dyestuffs
• • 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
  • D06P3/82—Textiles which contain different kinds of fibres
  • D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
  • D06P3/8276—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing ester groups

Definitions

• Y is lower ester, ether or acyl and Z is lower alkyl, alkoxy or halogen.
• Preferred dye assistants include naphthyl carbonic acid esters.
• the present invention is directed to a process for dyeing and/or printing a hydrophobic textile material, particularly polyesters or cellulose triacetate.
• a dyeing process employing a dyeing assistant which is substantially non-polluting and biodegradable.
• dye carriers included chlorinated hydrocarbons, for example chlorinated benzene. Additionally other carriers, such as derivatives of benzene or phenol, such as orthoor paraphenylphenol, benzyl alcohol, benzene carbonic esters or ethers and benzoic or salicylic acid have been employed.
• 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 areextremely 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.
• 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.l.) 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, DA- CRON, 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:
• the preferred carriers melt below about 100C. 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:
• R is C C -alkyl, benzyl or phenyl; Z is halogen or C C -alkyl; n is O or 1 and b is O, l or 2.
• the particularly preferred halogen substituent is chlorine.
• the preferred R, groups have been found to be particularly ecologically desirable having substantially no odor and low toxicity in the carrier compounds.
• 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 a-methyl naphthoate; a-benzyl naphthoate; ,B-ethyl naphthoate; methly-a-naphthyl acetate; oz-phenylnaphthoate and chlorophenyl-naphthyl acetate.
• the benzyl and phenyl R and R groups may have substituted thereon up to three C,C -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.
• 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.
• the carrier can be dissolved in a solvent, such as an alcohol, and then added to the dyebath which contains a suitable emulsifier.
• particularly useful emulsifiers include oxethylated sulfonates, alkylarylphenolsor sulfates of higher fatty acids.
• 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-sulfopl1thalic 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.
• 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.
• 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 nontoxicity, 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 orthophenyl-phenol.
• the naphthoic ether carriers of the present invention can be formed from conventional procedures such as reacting an aor B-haloalkylene naphthalene such as aor B-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 aor ,B-haloalkylnaphthalene such as 0:- or B-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-a-naphthyl acetate.
• a naphthoic acid esters an a,B-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.
• concentration of carrier will depend in part on the type of disperse dye employed, the fiber to be dyed and the technique of application.
• the dyeing process may be employed with any of the conventional disperse dyestuffs known to the art.
• suitable disperse dyes are Color lndexC. l.Disperse Dyes.
• Typical azo disperse dyes are Cibacet Orange 2R (C.l. Disperse Orange 3) No. l 1005 and Disperse Fast Yellow G (C.l. Disperse Yellow 3) No. 1 1855.
• Typical anthraquinone dyes are exemplified by C1 Disperse Violet 8 No. 62030 and Cl. Disperse Blue 1. Examples of other disperse dyes include C.l. Disperse Yellow 4; Disperse Yellow 1 No. 10345; Disperse Orange 13 No.
• Disperse Orange 3 Nof 11005 Disperse Yellow 3 No. 11855; Disperse Orange l No. 11080; Disperse Red 19; Disperse Red 1 No. 1110; Disperse Red '131No. 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 Cl. 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 pro-' cess wherein the dyebath is under a pressure of from about 3 to 4 atmospheres in a closed container at temperatures up to about 135C.
• the disperse dyes are brought into a state of suspension inthe dyebath employing conventional procedures.
• the dye can be stirred with to times its weight of water at to C and allowed to stand for 10 minutes with occasional agitation.
• 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 liquid content of the dyebath was adjusted to provide a liquor to fabric weight ratio of 30: 1.
• a polyester fabric formed from cationic modified polyethylene terephthalate was introduced into the aqueous dyebath.
• EXAMPLE 2 An aqueous dyebath was formed containing 8% by weight of an emulsion consisting of 65% by weight of the total emulsion of a-benzylnaphthoate by weight of the emulsion of the ammonium salt of oxethylated nonylphenol sulfate by weight of the emulsion of water
• 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 B-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 l 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-anaphthyl 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, 5O g/k of a-phenylnaphthoate and a thickener of starch ether-locust bean gum.
• the print was submitted to a 2-minute curing at 320F. 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 parts of chlorophenyl naphthylacetate and 15 parts of polyoxethylated phenol emulsifier.
• the aqueous dyebath also contained 1% of the dyestuff employed in Example and 1% of the following dyestuff:
• 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 (CH -COOR wherein R is C -C -alkyl, benzyl or phenyl; Z is halogen or C -C -alkyl; n is 0 or 1 and b is 0, l or 2; and said benzyl and phenyl each have from 0-2 Z radicals substituted thereon.
• a disperse dyestuff and a carrier which is a naphthyl carbonic acid ester of the formula (CH -COOR wherein R is C -C -alkyl, benzyl or phenyl; Z is halogen or C -C -alkyl; n is 0 or 1 and b is 0, l or 2; and said benzyl and phenyl each have from 0-2
• 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 I jiij (CH COOR wherein R is C -C alkyl, benzyl or phenyl; Z is halogen or C -C -alkyl; n is O or 1 and b is 0, 1 or 2.

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• Engineering & Computer Science (AREA)
• Textile Engineering (AREA)
• Chemical & Material Sciences (AREA)
• Dispersion Chemistry (AREA)
• Coloring (AREA)

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Family Applications (1)

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Cited By (2)

Citations (3)

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• 1973
  • 1973-01-26 US US326921A patent/US3893805A/en not_active Expired - Lifetime
• 1974
  • 1974-01-17 JP JP49007592A patent/JPS49102980A/ja active Pending
  • 1974-01-19 DE DE2402599A patent/DE2402599A1/de active Pending
  • 1974-01-23 CH CH90774A patent/CH573506B5/xx not_active IP Right Cessation
  • 1974-01-23 FR FR7402288A patent/FR2310444A1/fr active Granted
  • 1974-01-23 CH CH90774D patent/CH90774A4/xx unknown
  • 1974-01-24 IT IT47906/74A patent/IT1002756B/it active
  • 1974-01-25 GB GB354674A patent/GB1414768A/en not_active Expired

Patent Citations (3)

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