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United States Patent (19) 11 4,229,178 Lazar Et Al

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United States Patent (19) 11 4,229,178 Lazar Et Al United States Patent (19) 11 4,229,178 Lazar et al. 45) Oct. 21, 1980 DYE COMPOSITIONS 3,625,011 12/1975 Boehmke ................................. 8/173 54 3,700,405 10/1972 Petite et al. .............................. 8/173 75 Inventors: Remus I. Lazar, Berwyn; Richard C. Reichel, Chicago, both of Ill. Primary Examiner-Joseph L. Schofer Assistant Examiner-Maria S. Tungol 73) Assignee: Welsicol Chemical Corporation, Attorney, Agent, or Firm-Dietmar Olesch; Robert J. Chicago, Ill. Schwarz 21 Appl. No.: 912,170 57 ABSTRACT 22 Filed: Jun. 5, 1978 This invention discloses compositions and methods for 51) Int. Cl......................... D06P 1/651; D06P 3/84; dyeing natural proteinaceous and synthetic polyamide D06P 1/16 fibers, particularly wool, silk and nylons, utilizing dye 52 U.S. C. ............................................ 8/583; 8/597 assistants effective both with acid and disperse dyes, 58) Field of Search ...................... 8/92, 173, 54, 21 B such assistants being combinations of a mixture of lower 56 References Cited esters of chlorinated benzoic acids with a mixture of U.S. PATENT DOCUMENTS lower alkyl esters of toluic and benzoic acids. 2,881,045 4/1959 Mecco et al. ............................ 8/173 3,203,753 8/1965 Sherburne .................................. 8/93 5 Claims, No Drawings 4,229, 178 2 venience such mixture will hereinafter be referred to as DYE CCA P50STCFS “MPTB'. Both MCB and MPTB have been recommended for BACKGROUND OF THE INVENTION use as dye assistants for the disperse dyeing of polyester 1. Field of the Invention fibers. When tested, in the dyeing system described in This invention relates to the dyeing of natural pro Example I, as assistants for both acid and disperse dye teinaceous and synthetic polyamide fibers, particularly ing of certain specialty nylons comprised of 40% or the normal and specialty nylons. greater of the condensation product of 4,4'-diamino 2. Description of the Prior Art dicyclohexyl methane and decanodicarboxylic acid The dyeing of nylons-manufactured fibers in which 10 having the basic repeating unit: the fiber-forming substance is any long chain synthetic polyamide having recurring amide groups as part of the H O O chain-may, depending on the specific type of nylon involved-be accomplished with many different classes of dyes, e.g.: basic, acid disperse, direct, etc. The acid 15 and disperse dyes are in wide commercial use and the dye compositions of this invention utilize these classes MCB, alone was found to be a moderately effective of dyes. For reasons of speeding of dyeing, maximum assistant for both acid and disperse dyes; MPTB, alone, utilization of dye and improving evenness of color 20 was satisfactory with acid dyes but not an acceptable throughout the dyed fiber, these dyes are generally used assistant with all the disperse dyes tested. Combinations in conjunction with "assistants' (sometimes designated of MCB with MPTB not only were satisfactory with as "carriers')-materials which promote the attainment the aforedescribed specialty nylon as dye assistants for of speedy dyeing, maximum dye utilization, etc. There acid dyes, but were also effective assistants for all the are a number of assistants commercially available, but 25 disperse dyes tested, particularly for the disperse dye the experiments carried out in the work leading to this Eastman Polyester Navy Blue 2R-LSW (Product of invention indicated that, generally, an assistant effective Eastman Chemical Products, Inc.), where, in contrast with an acid dye is not optimum for disperse dyes and to the ineffective, or moderately effective, results pro vice versa. Use of only one assistant for both acid and duced by the individual components, the combinations disperse dyeing would be advantageous to a dyer in that 30 were highly effective. The efficacy of the combinations inventories of different assistants could be reduced and as dye assistants for disperse dyes was substantially there would be less possibility of erroneous selection of greater than that of the individual members of the com assistant. binations. The ratio of components in the combination This invention provides for dye assistants which are may be from about 1:9 weight/weight to about 9:1 effective in both acid and disperse dyeing systems. 35 weight/weight MPTB/MCB, but preferably from SUMMARY OF THE INVENTION about 7:3 weight/weight to about 3:7 weight/weight MPTB/MCB. In accordance with this invention, there have been The assistants of the present invention are essentially found dye assistants effective with both acid and dis insoluble in water and to be effective in the normally perse dyes, such assistants comprising combinations of a used aqueous dye baths must be emulsified or otherwise mixture of lower alkyl esters of di- and mono dispersed in water. A convenient method of supplying chlorinated benzoic acids with a mixture of lower alkyl these assistants for industrial use in as emulsifiable con esters of toluic and benzoic acids. centrates-a mixture of emulsifying agents and assis DESCRIPTION OF THE PREFERRED tants which, when stirred with a minimum of energy 45 into water, will give a usable emulsion. While the EMBODIMENT amount and type of emulsifying agent for specific dyes While any of the lower alkyl (where lower alkyl is an and fibers is determined by experience and experiment, alkyl radical of from one to three carbon atoms) esters a generally useful emulsifier system is one containing of mono- and di-chlorinated benzoic acid are usable, the both anionic and non-ionic emulsifiers. Typical of an preferred embodiment employs the methyl esters. Any 50 ionic emulsifiers is the isopropylamine salt of dodecyl of the isomers-ortho, meta or para-of mono benzene sulfonic acid, of non-ionic emulsifiers is a po chlorinated benzoic acid are usable as are also any of the lyoxyethylene derivative of caster oil. isomers of di-chlorinated benzoic acid. The amount of Various amounts of the aforedescribed assistants can di-chlorinated esters in the mixture may vary from 80 to be used in order to accomplish the results of the present 95 weight percent with the mono-clorinated esters com 55 invention. The use of excess assistant while possible, is prising the remainder. For convenience, the mixture of wasteful since after an efficient amount has been added, methyl chlorobenzoates will be hereinafter referred to no additional beneficial results are achieved by an ex as “MCB’. cess. The amount of assistant to be used, expressed as a With the mixture of lower alkyl esters of benzoic and weight ratio of assistant-to-dye should be between toluic acids: methyl, ethyl and propyl esters are usable 60 about 1:1 and 20:1, the precise amount depending on the as are also any of the isomeric toluic acids. A ratio of fiber-dye-process conditions. (By "assistant' is meant 75:25 weight/weight alkyl toluates: alkyl benzoates is the active components of a formulation, e.g. in Example preferred but ratios from about 25:75 to about 90:10 are I, the 80 weight percent emulsifiable concentrate con usable in this invention. The alkyl ester mixture of the tains 80% "assistant”). The amount of dye in the dye preferred embodiment is comprised of about 75 weight 65 bath is commonly expressed as a weight percentage percent methyl para-toluate, 25 weight percent methyl on-weight-of-fiber (OWF) and may be from about 0.1 to benzoate. This mixture is commercially available under 10 with OWF percentages of from 1 to 5 being typical the designation "Methyl-P-Toluate/Benzoate'; for con of commercial practice. 4,229, 178 3. 4. "Acid dyes' are in general salts of organic acids The specific additives to be used and their amounts wherein the colorant portion of the dye is the anionic depend upon the particular fiber to be dyed and on the (negatively charged) moiety. The assistants of this in operating conditions chosen. vention are useful with fibers which can be dyed effec The following Example I illustrates methods of pre tively with acid dyes, such fibers include the natural paring and applying the dye compositions of the present proteinaceous fibers such as wool and silk and the syn invention, which is not limited thereto. thetic polyamide fibers such as the different types of The dyes used in the present invention and identified nylons (e.g. nylon 66 or the aforedescribed specialty in Example I are representative of the classes of acid nylons). and disperse dyes and were chosen to give the three "Disperse' dyes are called so because they are almost 10 primary colors of red, blue and yellow since by suitable insoluble in water-which is the most commonly used combination of these colors it is possible to obtain a dyeing medium-and are applied in the form of finely wide variety of hues. Unless otherwise specified all divided particles which are dispersed in water. The dye temperature are in degrees Celsius, weights in grams assistants of this invention are useful also in the dyeing and volumes in milliliters. Where "dye assistant' is of fibers for which disperse dyes are used. Such fibers 15 specified, the reference is to the emulsifiable concen include modified regenerated natural products such as trate or aqueous dispersion; with the assistants of this secondary cellulose acetate and cellulose triacetate, and invention, this concentrate contains 80 weight percent totally synthetic fibers such as the polyesters (e.g.-the active components, 20 weight percent emulsifiers. long chain condensation product of terephthalic acid and ethylene glycol) and the synthetic polyamides (e.g- 20 EXAMPLE I -nylon 66 or the aforedescribed specialty nylon). PREPARATION OF A DISPERSE OR ACID The actual procedures described below in Example I DYEBATH COMPOSITIONS AND DYEING for the applying of dyes to fibers using the dye assistants PROCEDURE of the present invention, are typical of those suggested for superatmospheric pressure dyeing of the aforede 25 Experimental dye assistants were first formulated into scribed specialty nylons which require relatively rigor emulsifiable concentrates by admixture at 30-40 C.
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