US2706142A - Treatment of dyed cellulose esters and ethers to inhibit gas fading - Google Patents

Treatment of dyed cellulose esters and ethers to inhibit gas fading Download PDF

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US2706142A
US2706142A US231438A US23143851A US2706142A US 2706142 A US2706142 A US 2706142A US 231438 A US231438 A US 231438A US 23143851 A US23143851 A US 23143851A US 2706142 A US2706142 A US 2706142A
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Prior art keywords
treatment
ethers
cellulose esters
dyed
fading
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US231438A
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Glahn William H Von
Lester N Stanley
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GAF Chemicals Corp
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General Aniline and Film Corp
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    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/44General 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
    • D06P1/64General 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
    • D06P1/642Compounds containing nitrogen
    • D06P1/645Aliphatic, araliphatic or cycloaliphatic compounds containing amino groups
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/44General 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
    • D06P1/60General 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 polyethers
    • D06P1/607Nitrogen-containing polyethers or their quaternary derivatives
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/44General 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
    • D06P1/64General 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
    • D06P1/642Compounds containing nitrogen
    • D06P1/6426Heterocyclic compounds
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34Material containing ester groups
    • D06P3/40Cellulose acetate
    • D06P3/42Cellulose acetate using dispersed dyestuffs

Description

United States Patent TREATMENT OF DYED CELLULOSE ESTERS AND ETHERS T0 INHIBIT GAS FADING William H. Von Glahn, Loudonville, and Lester N. Stanley, Delmar, N. Y., assignors to General Aniline & Film Corporation, New York, N. Y., a corporation of Delaware No Drawing. Application June 13, 1951, Serial No. 231,438
1 Claim. (Cl. 8-61) The present invention relates to the treatment of materials such as fibers, fabrics and the like which are made of or contain cellulose derivatives such as cellulose esters or ethers for the purpose of improving the fastness of the colors applied thereto.
In the dyeing of textile materials it is always desired that the resultant colored materials be as fast as possible to light, washing, dry cleaning and to other agencies such as gas or acid fumes. Many dyestuffs yield desirable shades on organic derivatives of cellulose which are fast to washing but which frequently suffer from a lack of fastness, particularly to oxides of nitrogen found in gas fumes such as the produces of combustion of coal, illuminating gas and the like thereby undergoing a change in shade; This change may take different forms involving on the one hand the dulling of the brightness of the shade, and on the other hand a marked change in color.
This undesirable effect is most readily illustrated in the case, for instance, of many anthraquinone dyes, particularly those containing an amino group which is free or substituted by alkyl or aryl radicals and which yield valuable blue shades on organic derivatives of cellulose. When the fabrics dyed with these colors are exposed to acid fumes the color changes from a pure blue shade to one having a reddish or, in some cases, a brownish cast. On continued exposure the color often changes to pink. Such changes naturally restrict the range of usefulness of these dyes, and methods of increasing the resistance of such dyes or dyeings made therewith to acid fading have reached great commercial significance. While the changes mentioned above are particularly noticeable in the case of the aforesaid anthraquinone dyes, it is to be understood that acid fading is by no means limited to these dyes since many azo and other vat dyes are also subject to this disadvantage.
In seeking to eliminate acid fading prior operators have sometimes after-treated the dyed organic cellulose derivative with the protective agent. It has been suggested in some cases that the organic derivative be pretreated with the protective agent, but it is obviously preferable to apply the protective agent in the dye bath along with the dyestufi. Despite the obvious advantages of the latter procedure, particularly when considered from the standpoint of the saving of time and expense, many protective agents available on the market today are not being applied directly in the dye bath. This is attributable to the fact that special properties are necessary for this method of application.
Many compounds have been suggested to overcome gas fading. Most of these compounds are amines, but While there are innumerable possible amines that may find some usefulness there are a number of other functions besides simply inhibiting gas fading which are required of a successful gas fading inhibitor. As mentioned above, it is desirable that they be applied directly in the dye bath, and hence they must be dispersible therein. It is also important that the compounds be colorless so as not to alter the color of the dyed material. In this connection they should be able to withstand prolonged exposure to light and gas fumes without yellowing or other discoloration. They should be fast to washing and dry cleaning, be odorless and of a low degree of toxicity. Needless to say, they must be substantive to the cellulose derivative.
From the vast field of possible compounds which 'ice might be useful for this purpose we have discovered that those having the following general formula are suitable:
R1 RAr-OAO-A-N wherein R in an alkyl radical of from 4 to 12 carbon atoms (butyl, isobutyl, amyl, isoand sec.-amyl, hexyl, octyl, dodecyl); Ar is selected from the group consisting of benzene, naphthalene and diphenyl radicals; A is selected from the group consisting of ethylene and propylene; and R1 and R2 are selected from the group consisting of alkyl, aryl, cycloalkyl, aralkyl, hydroxyalkyl, and the atoms necessary to complete a heterocyclic ring. Examples of R1 and R2 may be methyl, ethyl, propyl, phenyl, tolyl, cyclohexyl, benzyl, hydroxyethyl, and the atoms necessary to complete a pyridine, piperidine, quinoline, morpholine, etc. ring.
The compounds which fall within the scope of this application may be prepared in general by reacting the alkylaryloxy alkoxy alkylene chloride with a secondary amine as per the method of U. S. Patent 2,170,111.
Suitable compounds include:
canto-Q0 mmommmonun omncom 3ocnnoornament onto orrmongo (CH )g-OCzH,OCzH,N(CH3)z on, n-CsH| O 021140 CzH N(CH3)z c1130 (CH3)2CH2C error-Go ozuloognug H 01130 (CHiQzCHzC (cum-Gotham C2H4N(C3H1)2 onto (CHshCHzC (CH3).-OC2H4O CzH N(CgH C1H7 onto 0119201120 cum-Q0 oznloczmn The following example is illustrative of the invention but it will be understood that variations and substitutions may be made within the scope of the claims:
Example 10 parts p (a,a,'y, -tetramethylbutyl)phenoxyethoxyethyl dimethyl amine were dispersed in a mixture of 1 part polymerized ethylene oxide-alkylphenol condensation product and 1 part polymerized ethylene oxide-fatty alcohol condensation product. One part of this emulsion was diluted with 9 parts water.
Other emulsifying agents may be used. However the above combination was. found to give satisfactory emulslons.
Any of the above listed or related compounds may be substituted for the p-(ww'y-y-tetramethylbutyl)phenoxyethoxyethyl dimethylamine for test.
The emulsion containing the acid fade inhibitor was added, in an amount corresponding to 2-4% of the weight of the material to be dyed, to an aqueous bath containing as a dye-stuff 1-hydroxyethylamino-4-methylamino-anthraquinone, in an amount equal to 0.5% of the weight of the material to be dyed. The dyestuff concentration was about 0.2% in the resulting dye bath. Cellulose acetate silk, in the form of yarn or fabric, was worked in the dyebath for about 10 minutes at 71-88 C., then Washed with dilute aqueous soap solution, rinsed and dried. A control sample Was similarly dyed, except that no acid fade inhibitor was included in the dyebath. A bright blue coloration was produced on both of the samples, which was identical in the case of the control sample and the sample produced with the bath containing the acid-fade inhibitor.
The samples were tested for acid fading by exposure to combustion products of illuminating gas for prolonged periods, in accordance with the standard testing procedure as described in the 1946 Year Book of the A. A. T. C. C. pages 285-9. The acid fade resistance was rated as set out in the aforesaid handbook in terms of the time required to produce appreciable alteration of shade, the rating units corresponding to about 8 hours exposure to combustion gases. The control sample rapidly changed to a pinkish-blue shade, so that its rating was zero on the aforesaid basis. The rating of the sample dyed in accordance with this invention showed an acid fading resistance rated at 2+.
The advantage of this compound over many other suggested acid fade inhibitors is its freedom from causing any stain on white material, nor any dulling or change of shade on colored material. Exposure to gas fumes or the strong ultraviolet light of fadeometer does not cause any yellowing of white materials which is a distinct advantage.
It will be understood that any of the compounds in the list above may be substituted in the example in the same proportions and are operable to give substantially the same results.
We claim:
The process for the treatment of dyed cellulose derivative fibers to render the fibers resistant to gas fading without altering the color of the fibers, which comprises treating the fibers with an aqueous dispersion of a compound having the formula:
said dispersion containing as the emulsifying agent a mixture comprising equal parts of a polymerized ethylene oxide-alkylene phenol condensation product and a polymerized ethylene oxide-fatty alcohol condensation product.
References Cited in the file of this patent UNITED STATES PATENTS 2,008,902 Ellis Jul 23, 1935 2,017,119 Ellis Oct. 15, 1935 2,083,122 Olpin June 8, 1937 2,539,212 Strobel Jan. 23, 1951 OTHER REFERENCES Silk Journal and Rayon World for November 1945, p. 44.
American Dyestuff Reporter for May 12, 1952, pp. P297 to P304.
US231438A 1951-06-13 1951-06-13 Treatment of dyed cellulose esters and ethers to inhibit gas fading Expired - Lifetime US2706142A (en)

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2813774A (en) * 1954-02-05 1957-11-19 Basf Ag Process for improving the waste gas fastness of dyed cellulose derivatives
US3033640A (en) * 1954-06-16 1962-05-08 Saul & Co Incorporation of an organic basic compound into cellulose acetate materials
US3859045A (en) * 1971-07-22 1975-01-07 Allied Chem Ethoxylated aliphatic tertiary amines to reduce ozone attack on dyes in polyamide fibers
US3964861A (en) * 1971-12-23 1976-06-22 Allied Chemical Corporation Alkoxylated aliphatic amines to inhibit ozone fading of dyed polyamides
US3989455A (en) * 1973-05-29 1976-11-02 Allied Chemical Corporation Tertiary amines, substituted piperidine, morpholine or piperazine containing fatty acid moieties to prevent ozone fading of nylon fibers
US9018418B2 (en) 2011-09-19 2015-04-28 Beijing Sunpu Biochem. Tech. Co., Ltd. Method for preparation of aryl poly(oxalkyl) quaternary ammonium compound

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2008902A (en) * 1930-05-15 1935-07-23 Celanese Corp Coloration of materials
US2017119A (en) * 1931-02-11 1935-10-15 Celanese Corp Treatment of textile and other materials
US2083122A (en) * 1932-07-19 1937-06-08 Celanese Corp Manufacture of artificial filaments, threads, films, and the like
US2539212A (en) * 1948-11-05 1951-01-23 Gen Aniline & Film Corp Gas fading inhibitors for cellulose derivative dyes

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2008902A (en) * 1930-05-15 1935-07-23 Celanese Corp Coloration of materials
US2017119A (en) * 1931-02-11 1935-10-15 Celanese Corp Treatment of textile and other materials
US2083122A (en) * 1932-07-19 1937-06-08 Celanese Corp Manufacture of artificial filaments, threads, films, and the like
US2539212A (en) * 1948-11-05 1951-01-23 Gen Aniline & Film Corp Gas fading inhibitors for cellulose derivative dyes

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2813774A (en) * 1954-02-05 1957-11-19 Basf Ag Process for improving the waste gas fastness of dyed cellulose derivatives
US3033640A (en) * 1954-06-16 1962-05-08 Saul & Co Incorporation of an organic basic compound into cellulose acetate materials
US3859045A (en) * 1971-07-22 1975-01-07 Allied Chem Ethoxylated aliphatic tertiary amines to reduce ozone attack on dyes in polyamide fibers
US3964861A (en) * 1971-12-23 1976-06-22 Allied Chemical Corporation Alkoxylated aliphatic amines to inhibit ozone fading of dyed polyamides
US3989455A (en) * 1973-05-29 1976-11-02 Allied Chemical Corporation Tertiary amines, substituted piperidine, morpholine or piperazine containing fatty acid moieties to prevent ozone fading of nylon fibers
US9018418B2 (en) 2011-09-19 2015-04-28 Beijing Sunpu Biochem. Tech. Co., Ltd. Method for preparation of aryl poly(oxalkyl) quaternary ammonium compound

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