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Publication numberUS1941991 A
Publication typeGrant
Publication dateJan 2, 1934
Filing dateFeb 25, 1931
Priority dateFeb 25, 1931
Publication numberUS 1941991 A, US 1941991A, US-A-1941991, US1941991 A, US1941991A
InventorsLubs Herbert August, Walker Herbert Warren
Original AssigneeDu Pont
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Method of treating textile material and product
US 1941991 A
Abstract  available in
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Claims  available in
Description  (OCR text may contain errors)

Patented Jan. 2, 1934 UNITED STATES METHOD OF TREATING TEXTILE MATERIAL AND PRODUCT Herbert August Lube and Herbert Warren Walker, Wilmington, Bet, assignors to E. I. du Pont de Nemcurs & Company, Wilmington, DelL, a corporation of Delaware No Drawing. Application February 25, 1931 Serial No. 518,289

20 Claims.

lo-preciably limited by the fact that under certain conditions of storage, for example, storage in a warm humid atmosphere, there is a tendency for material dyed with these dyes to tender. pp This invention has for an object the stabiliza- -tion of goods dyed with sulphur blacks. Other objects are the inhibition and the retardation of tendering of goods dyed with sulphur blacks, the production of improved articles or" manufacture, and in general an advancement of the art. 'Other objects will appear hereinafter.

These objects are accomplished by immersing or passing sulphur black dyed goods in or through an aqueous solution of a solubl salt of an orthop amino-aryl-thio-glyco1lic acid or acids. In -general these compounds may be represented by the formula H H Hl IR-S it in which R represents a substituted or unsubstituted aryl group to which the nitrogen and the sulphur atoms are attached in ortho positions and M is a metallic element capable of forming 5 a soluble salt with the remainder of the compound. Where convenient or necessary the goods are squeezed or wrung out before drying.

The invention will be readily understood from a consideration of the following examples in lio'which the parts are given by weight.

Example I Cotton goods were dyed with about 12% of the dye resulting from the thionation of di-nitrophenol and further treated at room temperature with an approximately 16% aqueous solution of the sodium salt of G-methyl-1-amino-phenyl-2- thio-glycollic acid and wrung out to leave 10% p of the dry agent based on the weight of the dry goods. After the material had been dried samples of both after-treated and untreated goods similarly dyed were subjected to the action of air and steam at about 135 C. for approximately 7 four hours. Great differences were found in the resulting materials. The untreated material had lost approximately of its strength whereas the strength of the after-treated goods had not been appreciably altered.

Example II Cotton goods were dyed with 5% sulfogene carbon M (a sulphur dye made by the thionation of diand tri-nitro phenol) based on the Weight of the goods and were padded at room temperature with a 5% aqueous solution of the sodium salt of 6-methyl-l-amino-phenyl-2-thio-glycollic acid and wrung out so as to leave 5% of the dry agent on the dry goods, and dried. The goods were then subjected to an accelerated ageing test wherein they are suspended in an air oven at 95 C. for five and one-half weeks. At the end of this time the goods similarly dyed with sulfogene carbon M and otherwise untreated were found to have lost in tensile strength whereas the same goods treated with aminophenyl-thio-glycollio acid salt and aged simultaneously under the same conditions showed no decrease in tensile strength.

Example III The process of Example II was carried out using a 10% solution of the sodium salt of l-amino-4-ethoxy-phenyl-2-thio-glycollio acid. After two weeks ageing in an air oven at C. the control or untreated sample had last 76% of its initial tensile strength whereas the sample of the same goods treated with the anti-tendering agent tested at the same time suffered no loss in strength.

Example IV Cotton goods were dyed with 12% sulfogene carbon HXX (a sulphur dye made by the thionation of a di-nitro phenol) and padded at room temperature with a 10% aqueous solution of the.

sodium salt of l-amino-4-ethoxy-phenyl-2-thioglycollic acid. They are then wrung out under such conditions as to leave thereon 10% of the dry agent on the basis of the weight of the dry goods and dried. Samples of both after-treated and untreated dyed goods were subjected to the action of air and steam at 135 C. for four and one-half hours. Wide differences in resistance toward tendering were evident. The untreated material lost 77% of its strength whereas the goods submitted to the after-treatment with the amino-phenyl-thio-glycollate retained its initial strength during the test.

It is to be understood that the invention is not limited to the specific compounds mentioned in the examples. In general, use may be made of any one or more of the soluble salts or" members of the class of compounds known as ortho-amino-aryl-thio-glycollic acids. lreferably the 5 specific agent used is one of those listed in the examples or a member of the group consisting of the alkali salts of l-amino-naphthalene-Z-thioglycollic acid, 4-methyl-1-amino-phenyl-2-thioglycollic acid, and l-amino-phenyl-Z-thio-glycollic acid. In particular 1-amino-4-ethoxyphenyl-Z-thio-glycollic acid is preferred.

The amount of the anti-tendering agent (also called tendering retarder) may be varied within wide limits. Preferably the concentration used falls Within the range 0.5 to 15.%. Aside from reasons of economy and the influence which the presence of the tendering inhibitor exerts upon the color of the dyed goods there is no disadvantage in using more than the preferred amount.

For particular conditions, less than the preferred range may be used satisfactorily.

As noted above the aryl nucleus in the tendering inhibitor may be substituted or unsubstituted. Especially desirable results are obtained when 25. the substituent or substituents are from the group hydroxy, alkyl, alkoxy and halogen.

While the metal of the thio-glycollic acid salts previously referred to may be any one capable of forming a soluble salt, the alkali metals espeao, cially sodium, potassium and ammonium, are

preferred.

The improvement in the ageing quality of sulphur black dyed goods resulting from the use of the above described anti-tendering agents is very 35.. pronounced and exceeds the improvement resulting from the use of any other material 01" which applicants are aware. By use of these agents cotton goods dyed with sulphur blacks may be kept for an indefinite period of time in warm dry 40. or moist atmospheres without undergoing deter1- oration.

The presence of the small quantity of the thioglycollic acid salt on the sulphur black dyed material so stabilizes the goods and inhibits the 4&1 tendering that they may be considered essentially unaltered after long periods of time.

'As many apparently widely dififerent embodiments of this invention may be made Without departing from the spirit and scope thereof, it

sa is to be understood that we do not limit ourselves to the specific embodiments thereof except as defined in the appended claims.

We claim:

1. Cotton goods dyed with a sulphur black fid produced by thionating a nitro-phenol and having thereon the sodium salt of l-amino-lethoxy-phenyl-Z-thio-g1ycollic acid in an amount between .5 and 15.%.

2. Goods dyed with a sulphur dye and having 6Q thereon a soluble salt of an ortho-amino -arylthio-glycollic acid.

3. Sulphur black dyed goods having thereon a soluble salt of an ortho-amino-ary1-thio-glycollic acid.

4. Sulphur black dyed goods having thereon a salt'of an ortho-amino-aryl-thio-glycollic acid and an alkali metal.

' 5. Sulphur black dyed goods having thereon a salt of an ortho-amino-aryl-thio-glycollic acid 1. and a member of the group consisting of sodium,

potassium and ammonium.

6. Sulphur black dyed goods having thereon a sodium salt of an ortho-amino-aryl-thio-glycollic acid.

'7. Sulphur black dyed goods having thereon in which R represents a substituted or unsubstituted aryl group to which the nitrogen and the sulphur atoms are attached in ortho positions and M is a metallic element capable of forming a soluble salt with the remainder of the compound.

10. Goods dyed with a sulphur black dye and having thereon a compound of the formula in which the phenyl group may be substituted or unsubstituted.

11. Goods dyed with a sulphur black dye and having thereon a compound of the formula l H-lTI 18 in which the naphthyl group may be substituted 1 or unsubstituted.

12. Goods dyed with a sulphur black dye and having thereon a compound of the formula H H o 1 29 Hl IRS( il(%Ol\/l in which R represents a substituted aryl group to which the nitrogen and the sulphur atoms are 5 attached in ortho positions and M is a metallic element capable of forming a soluble salt with the remainder of the compound.

13. Goods dyed with a sulphur black dye and having thereon a compound of the formula H H 0 H 1lIR-s( 1 lo1v1 in which R represents an unsubstituted aryl group to which the nitrogen and the sulphur atoms are attached in ortho positions and M is a metallic element capable of forming a soluble salt with the remainder of the compound. 7 40 14. Goods dyed with a sulphur black dye and 1 having thereon a compound of the formula in which R represents an aryl group, substituted by a hydroxy, alkyl, alkoxy or halogen, to which the Nitrogen and the Sulphur atoms are attached in ortho positions and M. is a metallic ele- 150 ment capable of forming a soluble salt with the remainder of the compound.

15. Goods dyed with a sulphur black dye otherwise capable of tendering and containing a soluble salt of an ortho-amino-aryl-thio-glycollic acid.

16. The process comprising soaking sulphur black dyed goods in a solution of a soluble salt of an ortho-amino-aryl-thio-glycollic acid.

17. The process of preventing or retarding the tendering of goods dyed with sulphur black which comprises adding thereto a soluble salt of an ortho-amino-aryl-thio-glycollic acid.

HERBERT AUGUST LUBS. HERBERT W. WALKER.

Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US7018424 *Feb 13, 2003Mar 28, 2006The Board Of Regents Of The University Of NebraskaSulfur dye protection systems and compositions and methods employing same
US7101407Feb 13, 2003Sep 5, 2006The Board Of Regents Of The University Of NebraskaSulfur dye protection systems and compositions and methods employing same
Classifications
U.S. Classification8/587, 8/133, 8/597, 8/918, 8/652
International ClassificationD06P1/653, D06P1/30, D06P1/647
Cooperative ClassificationY10S8/918, D06P1/6536, D06P1/30, D06P1/647
European ClassificationD06P1/647, D06P1/653D, D06P1/30