US2822234A

US2822234A - Ice-colors in textile printing with neutral steam

Info

Publication number: US2822234A
Application number: US475823A
Authority: US
Inventors: Breig Kurt; Glietenberg Eugen
Original assignee: Bayer AG
Current assignee: Bayer AG
Priority date: 1953-12-28
Filing date: 1954-12-16
Publication date: 1958-02-04
Anticipated expiration: 1975-02-04

Description

ICE-COLORS IN TEXTILE PRINTING WITH NEUTRAL STEAM Kurt Breig and Eugen Glietenberg, Leverkusen-Bayerwerk,

No Drawing. Application December 16, 1954 Serial No. 475,823

Claims priority, application Germany December 28, 1953 6 Claims. (Cl. 8-71) The present invention relates to a process of preparing ice-colors in textile printing and dyeing.

In preparing ice colors in textile printing from diazoamino compounds, thickened caustic alkaline solutions of usual ice-color coupling components and alkali metal Salts of diazoamino compounds containing solubilizing groups in the radical (stabilizer) not taking part in the formation of the dyestuft", are printed on the fibre and the dyestuff is developed by a treatment with dilute acid or, preferably, with acid-containing steam. This acid treatment involves anumber of disadvantages and therefore many attempts have been made to effect the development of the icecolors solely by applying neutral steam, es pecially since it is only possible by this kind of development to prepare ice-colors and vat-colors side by side. Thus verysatisfactory results could be achieved by reducing the quantity of caustic alkali in the printing pastes or by adding compounds splitting off acid (cf. applicates Patent tions Nos. 313,582, now Patent No. 2,758,001, 313,583

and 390,084). 7

The ideal case would be, however, dyestufi combinations which can be developed in neutral steam without an addition of compounds splitting oif acid or binding The solution of this problem would therefore alkali. mainly reside in the use of suchdiazoamino compounds which easily and completely split up in neutral steam but are completely stable in the cold and'thereby afford a good keeping quality of the printing pastes. The capability of diazoamino compounds to split up greatly de-.

pends upon the basicity of the diazotizable amine on the one side and of the stabilizer on the other side. Every diazotized aromatic amine possesses, depending upon its substituents, a very difierent coupling energy and forms,

according to whether it is'more strongly or more weakly basic, diazoamino compounds which split up more easily or more difiicultly. A similar statement holds true for the-arnines used as stabilizers. It is therefore necessary to: adapt carefully to another amine and stabilizerif a quantitative scissio n of the diazoamino compound is to be obtained by applying solely neutral steam. The ideal case would be to provide the suitable stabilizer for each amine; this, however, would cause considerable additional costs whentechnically applied.

fWe have now found that the combinations of dihalogeno-alkylor dihalogeno-alkoxy anilines Withl-alkylamino-5 (4)-sulfobenzoic acids represent ideal diazoamino compounds for the purpose discussed. They yield together with ice-color coupling components when developed with neutral steam very deep and strong prints on cellulosic fibres as well as a good fixation on staple fibre fabrics from regenerated cellulose. In spite of the easy scission in neutral steam the printing pastes exhibit a very good keeping quality. The prints further Suifer no visible loss in depth of color if printed side by side with vat-colors. Also reducing agents and caustic alkali carried over from vat-color printing pastes have no detrimental infiuence upon the development of the dyestuffs.

2,822,234 n Patented Feb. 4, 1958 It is important in this connection that the new combinations do not decrease in strength under the intermediate rollers in the composite print side by side with vat-colors; this means a special advance over the known combinations. 7

The combinations according to the present invention not only show very good properties in printing but also prints obtained therewith are distinguished by general I good properties,in particular by an excellent fastness to light. 7

The following examples illustrate the invention without, however, limiting it thereto.

Example 1 ethoxy-benzene are dissolvedin 50 ml, of alcohol or an- 1' other suitable solvent and 15-20 grams of caustic soda solution of 38 B. in approximately 300 ml. ofwa'te'r and, after'stirring into 500 grams of thickening agent,

made up with water-to 1000 grams. The printing'paste thus obtained is printed on' the fibre in customary manner. 1 "After dryingtheprinted textile material is steamed withneutral steam for about 5-10 minutes, whereby the de-' Afters'oaping at the boil andthe usual removal of the'thicke'ning agent, the dyed textileis rinsed and dried. A clear scarlet is obtained which is veryfast to light. Theiprintin'g paste velopment of the dyestuff takes place.

is of very good keeping quality. The depth of color of the printings on staple fibi'e fabricis' equal to that of the printings on cotton. In printing simultaneously with vat- I dyestuifs, the combination shows on employing squeezing rollers no decline in the depthof color.

.Example 2 When using according to Example 1 the sodium salt of the diazoamino compound prepared from 1-a1nino-2- stabili'zer described in 'Example 1 and 1-acetoacetyl-- amino-4-chloro-2,S-iiirnethoxybenzene yields on the fibre, 1 after neutral development, a greenish yellow which is -methyl-4-bromo-5-chlorobenzene and the stabilizer employed in Example 1, together withithe 1-(2'-hydroxycarbazol-3'-carboylamino)-4-chlorobenzene, a full brown is obtained which is very fast to light examples from the sodium salt of the diazoamino compoundof 1-amino-3-methyl-4,6-dichlorobenzene with the very fast tolight. I H

' Exdmp le'4 By replacing the sodium salt of the diazoamino compound of Example 1 by the sodium salt of the diazoamino compound from diazotized 1-amino-4-rnethyl- 2,5-dichlorobenzene and 2-isopropylamino-5-sulfobenzoic acid as stabilizer, and using 1-(2,3'-hydroxynaphthoylamino)-2-methoxybenzene as coupling component, adding about 10-20 grams of caustic soda solution of 38 B. per kilogram printing color, a printing paste is obtained which yields on the fibre, after neutral steaming, a strong fast red, the depth of which-on cotton is equal to that on staple fibre fabric.

1 mol of diazotized 1-amino-2-methoxy-4,S-dichlorobenzene is run into a sodium carbonate alkaline solution of 1.1 mol of the diso'dium salt ofithe' 2 methylamin'o'-5- sulfobenzoic acid, and .the'diazoamino compound thus formed is salted out witlr so'dium'chlorid'e after" its com-i plete formation.

60 grams of a mixture consisting of equivalent part'sifof the sodium salt of the diazoamino compoundtlius formed and the 1-(2,3'-hydroxynaphthoylamino)-2-methoxybenzone are dissolved in about 50 ml. of glycol monoethyl ether or another suitablesolvent and. l-20grams Off: caustic soda solution of 38 B.. in approximately 300" ml. of hot water and, after'stirring into'500" grams'of thickening agent, made up' with water to 1000 grams. This printing paste yields, after neutral steaming, a full bluish redof excellent fastness to light. The depth of color on staple fibre fabric is in strength equal to that on cotton.

Example 6 The sodium salt of' the diazoamino compoundof: diazotized lamino-2amethoxy-4-bromo-S-chlorobenzene and the Z-ethylamino-S-sulfobenzoic acid as stabilizer yields in equivalent mixture with l-benzoylacetylaminoi- 4-benzoylamino-2,S-dimethoxybenzene underv the conditions of Example 5, after. steaming in neutral steam, a*-' clear yellow'which. is very fast to light. The. strength of. color on cotton as well as-on. staplefibre. fabricis" equally deep.

We claim:

1. A process. for printing, textile fibres of the group consisting of' cotton and regenerated cellulose fibers with insoluble azo dyestuffs developed on the fibre whichcom prises diazotizing a compound selected from the group consisting of dihalogeno-alkyl-anilines and dihalogenoalkoxy-anilines, reacting the diazo compound formedwitli a compound selected-from the group consisting of 2- alkali salt with an alkali salt of 1-acetyloacetylamino-4- chloro-2,S-dimethoxybenzene, adding a thickener to the mixture, applying the resulting mixture to a textile fiber, and developing the dyestutl onsaid fiber by steaming with a neutralsteam.-

4. A process for printing textile fibers of the group consisting of cotton and regenerated cellulose fibers with insoluble azo'dyestulls developed on the fiber which comprisesdiazotizing 1-amino-2-methyl-4-bromo-5-chlbrobenzene, reacting the diazo compound with 2-ethylamino-5- sulfobenzoic acid in the presence of a fixed alkali to form 'an alkali. sali. of a diazoami'no. compound, mixing said alkali salt with an alkali salt of l-(2'-hydroxycarbazol-3'- car-boylamino)r4echlorobenzene, adding a. thickener tothe mixture, applying the resulting mixture to a textile fiber, and developing-thedyestufi on said fiber by steaming with a neutral steam.

5: A process for printing textile fibers of the group consisting of cotton and regenerated cellulose fibers with insoluble azo' dye'stufis developed on the fiber which comprises diazotizing l amino-4-methyl-2;S-dichlorobenzene, reacting: the. diazo compound with 2-isopropylamino-5-sulfobenzoic acid in the presence of a fixed alkali to form an alka'li salt of a diazoarnino compound, mixing said alkali salt withan alkali salt of 1-(2',3'-hydroxynaphthoyl-a-mino)-2-methoxybenzene, adding a thickener to the mixture; applying the resulting mixture to a textile fiber,

alkylamino-5-sulfobenzoic acid: and 2-alkylamino-4-sulfobenzoic acid in the presenceof a fixed alkali to'forrn an alkali saltof. a diazoamino compound, mixing said alkali salt with an alkali'salt of a couplingcomponent, adding a thickener to' themixture, applyingtheresul'ting mixtureito a textile fibre, anddeveloping the dyestulffonv said fibre by steaming withneutral-steamx 2. A process for printing textile fibers of the group consisting of cotton and regenerated cellulose fibers with insoluble'azo dyestutfsl developed onthe fiber which? comprises. diazotizing 1.-amino-2-'methyl-4,'S-dihlorobenzene, 1

reacting the diazo. compound formedwith- 2sethylarnino S-sulfobenzoic acid in the presence of a fixed alkali to form analkali salt; of: a diazoaminocompoundi-mixing' said alkali salt with an. alkali salt of: 1:-(2f,3-hydroxy-' naphthoylamino)-2-ethoxybenzene, adding a thickener to the mixture, applying the resulting mixture to a textile fiber, and.developingthe:dyestutfsmn said'fiber byfsteaming; with av neutral steam.

3'. Aprocess for printing-fibers'of'the group'consisting and developing the dyestufi on said fiber by steaming with a-nentral-steam.

-6.'A process for printing textile fibers of the group consisting of cottonand regenerated cellulose fibers with yinsoluble'azo dyestuffs developed on the fiber which comprises-r diazotizing 1-amino-Z-methoxy-4,5-dichlorobenv zene; reacting the diazo compound with Z-methylamino-S- sulfobenzoic acid in the presence of a fixed alkali to form an alkali salt of a diazoamino compound, mixing: 'said alkali salt with an alkali salt of l-(2,3'-hydroxynaphthoyl-amino)-2-methoxybenzene, adding a thickener to themixture, applying the resulting mixture to a textile fiber; and developing the dyestufll on said fiber by steaming-'with a neutral steam.

References Cited in the file of this patent n UNITED STATES PATENTS 882,561

Haller Oct. 11, 1932 2,095,402" Dahlen Sept. 21, 1937 2,338,639, Heaton Jan. 4, 1944 2,396,357 Wiest Mar. 12, 1946 2,522,838 Petitcolas Sept. 9, 1950 2,675,374 Petitcolas Apr. 13, 1954' 2;158,001' Glietenberg Aug. 7, 1956 FOR'EIGN' PATENTS 4975407 Great Britain Dec. 19, 1938' 042,356 France" June 3', 1953' 1,056,501 France Oct. 21, 1953'- 4 OTHER REFERENCES.

Chernl Technology of Dyeing and Printingfby L.

Diserens, translated by Wengrafand Baumann, vol. 4;

Claims

1. A PROCESS FOR PRINGINT TEXTILE FIBRES OF THE GROUP CONSISTING OF COTTON AND REGENERATED CELLULOSE FIBERS WITH INSOLUBLE AZO DYESTUFFS DEVELOPED ON THE FIBRE WHICH COMPRISES DIAZOTLZING A COMPOUND SELECTED FROM THE GROUP CONSISTING OF DIHALOGENO-ALKYL-ANILINES AND DIHALOGENOALKOXY-ANILINES, RACTING THE DIAZO COMPOUND FORMED WITH ALKYLAMINO-5-SULFOBENZOIC ACID AND 2-ALKYLAMINO-4-SULALKYLAMINO-5-SULFOBENZOIC ACID AND 2-ALKYLAMINO-4-SULFOBENZOIC ACID IN THE PRESENCE OF A FIXED ALKALI TO FORM AN ALKALI SALT OF A DIAZOAMINO COMPOUND, MIXING SAID ALKALI SAIT WITH AN ALKALI SALT OF A COUPLING COMPONENT, ADDING A THICKENER TO THE MIXTURE, APPLYING THE RESULTING MIXTURE TO A TEXTILE FIBRE, AND DEVELOPING THE DYESTUFF ON SAID FIBRE BY STEAMING WITH NEUTRAL STEAM.