US2364726A - Process for improving the dyeings and prings prepared with watersoluble dyestuffs - Google Patents

Process for improving the dyeings and prings prepared with watersoluble dyestuffs Download PDF

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Publication number
US2364726A
US2364726A US340200A US34020040A US2364726A US 2364726 A US2364726 A US 2364726A US 340200 A US340200 A US 340200A US 34020040 A US34020040 A US 34020040A US 2364726 A US2364726 A US 2364726A
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US
United States
Prior art keywords
dyeings
copper
prepared
formaldehyde
prings
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US340200A
Inventor
Landolt Albert
Ruperti Andreas
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
FIRM CIBA PRODUCTS Corp
Original Assignee
FIRM CIBA PRODUCTS CORP
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to GB13277/40A priority Critical patent/GB536480A/en
Priority to DEG101004D priority patent/DE767276C/en
Priority to FR862209D priority patent/FR862209A/en
Priority to FR865903D priority patent/FR865903A/en
Application filed by FIRM CIBA PRODUCTS CORP filed Critical FIRM CIBA PRODUCTS CORP
Priority to US340200A priority patent/US2364726A/en
Application granted granted Critical
Publication of US2364726A publication Critical patent/US2364726A/en
Priority to BE474397D priority patent/BE474397A/xx
Priority to NL133450A priority patent/NL65947C/xx
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • 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
    • D06P1/667Organo-phosphorus 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
    • 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
    • D06P1/52General 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 synthetic macromolecular substances
    • D06P1/56Condensation products or precondensation products prepared with aldehydes

Definitions

  • Example 1 A's high-molecular compounds come inter alia in Example 1 question those which are prepared by condensation of formaldehyde with compounds containing A ot 0 inen fabric is dyed on the jig with nitrogen.
  • the latter may be capable or incapable Direct y Blue GS (Schultz, 5 0) rinsed of being hardened, and squeezed or hydro-extracted.
  • This aftertreatment may consist of a simple In place of Direct sky Blue many other dyestuffs may be used, giving thesame result.
  • wet treatment 1n baths which contain the prod- Among these may be mentioned Direct Blue RW ucts concerned. It may also consist of a wet (Schultz No. 507), Direct Brown M (Schultz No. treatment combined with a subsequent dry treat a 412), Chlorantine Fast Brown BRLL (Schultz ment at raised temperature, 1f formaldehydevol.
  • Chlorantine Fast V1o1et 2R1L condensation products which are capable of being Chlorantine Fast Yellow 4GLL, Chlorantine Fast hardened are used as high-molecular organic ba- Orange TSRLL, Chlorantine Fast Grey 2BLL (all 810 compounds, whereby the fastness to wet Schultz su vol 1 e 79) treatment, in particular the fastness to washing, Dag as a rule is still further improved.
  • Example 2 ggg gg gfig g m light may be unfavwr' A material composed of 70% wool and 30% 5 viscose-rayon staple fibre is dyed by known meth- It has now been found that this disadvantage Dds with 4% Chlorantine Brown BRLL (Schultz, may be eliminated if an aitertreatment with copsupp. vol. 1, page 79) rinsed, hydro-extracted, per salts is combined with the aftertreatment and impregnated at room temperature with a with the aqueous solution of the high-molecular solution contamin litre condensation products from formaldehyde and g per nitrogen-containing compounds.
  • Example 3 A dyeing of Chlorantine Fast Orange TGLL on cotton material is impregnated with a solution containing per 100 parts water, 16 parts dimethylol-urea, 1 part ammonium phosphate, and 1 part copper chloride (the parts being by weight) and is then dried at 110 (2., whereby the fastness of the dyeing to wet treatments is increased by the high-molecular compound formed.
  • the thus aftertreated dyeing is exposed to light, it exhibits a better fastness to light than a dyeing aftertreated in the same manner but with exclusion of the copper salt.
  • Chlorantine Fast Orange TGLL is replaced by Chlorantine Fast Bordeaux B or by Chlorantine Fast Blue 3RLL.
  • Improvement in the process oi increasing the i'astness properties of dyeings and prints, which have been obtained by means of a water-soluble dyestufl. and aftertreatment with a high-molecular organic compound, produced by condensation of formaldehyde with a compound containing at least once the group solubie dyestufls and aftertreatment with a high- 4 molecular organic compound, produced by the condensation of formaldehyde with melamine, consisting in combining the aftertreatment with a simultaneous treatment with a solution of a copper compound in the same bath, and then subjecting the material thus treated to a dry treatment at raised temperature.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Description

memes Dec. 12, 1944 rnocnss ron nurnovme 'rnn Dramas AND rnm'rs PREPARED wrrn warn-a- SOLUBLE nrss'rurrs Albert Landolt, Riehen, and Andreas Ruperti,
Arlesheim, Switzerland, assignors, by memo aasignments, to the firm Ciba Products Corporationt Dover, Del.
No Drawing. Original application October 13,
1939, Serial No. 299,390. Divided and this application June 12, 1940, Serial No. 340,200. In Switzerland December 21, 1938 A Claims.
This application is adivision of our application for Letters Patent Ser. No. 299,390, filed October 13; 1939.
It is known that the wet-fastnesses of dyeings pie, with baths which contain copper salts in addition to salts of high-molecular organicbasic compounds: if required, the dry treatment at raised temperatures may also hereupon take and prints, which have been prepared with the 5 place. help of water-soluble dyestuifs, may be increased As suitable copper salts, copper sulphate, copby aftertreatment with high-molecular organic per nitrate, copper chloride, copper acetate, etc., compounds, if necessary in the form of their salts. may be mentioned. A's high-molecular compounds come inter alia in Example 1 question those which are prepared by condensation of formaldehyde with compounds containing A ot 0 inen fabric is dyed on the jig with nitrogen. The latter may be capable or incapable Direct y Blue GS (Schultz, 5 0) rinsed of being hardened, and squeezed or hydro-extracted. The still moist Among the high-molecular formaldehyde conmaterial is Padded on the mangle F densation products may be mentioned such as Perflture ugh a solution containing D litre are derived from formaldehyde and nitrogen- 30 gms of ahydrophobic mel mine formaldehyde containing compounds such as melamine, gua condensation product (obtained from 1 mo] d e. ua y u e urea, d cy In melamine and 6 mols formaldehyde), soluble this connection, compare U. S. patent specificain water in t ratio of 1;1 tions Nos. 2,093,651, 2,169,546 and 2,106,938. 10 cm. formic id,85% and Among the condensation products containing 1 o 5 gms copper hloride, or the equivalent nitrogen, those are particularly valuable which quantity of another copper Salt, such as copper are obtained by the condensation of formaldeformate or copper t t After drying, th hy e th Compounds which contain least once I fabric is subjected to a hardening treatment the group over heated cylinders for /2 minute at 130 c. N-- The treated dyeing possesses very good fastness ('3=N to light in addition to exceptional fastness to water and perspiration. By subsequent wash- N ing with soap and soda, the fastness to light is u p du a f r xampl m lam ne, suani- 3 not decreased, so that here a permanent imdine, guanyl urea, dicyandiamide, already men- -provement in this property is concerned. tioned.
This aftertreatment may consist of a simple In place of Direct sky Blue many other dyestuffs may be used, giving thesame result. wet treatment 1n baths which contain the prod- Among these may be mentioned Direct Blue RW ucts concerned. It may also consist of a wet (Schultz No. 507), Direct Brown M (Schultz No. treatment combined with a subsequent dry treat a 412), Chlorantine Fast Brown BRLL (Schultz ment at raised temperature, 1f formaldehydevol. 2, page 48), Chlorantine Fast V1o1et 2R1L, condensation products which are capable of being Chlorantine Fast Yellow 4GLL, Chlorantine Fast hardened are used as high-molecular organic ba- Orange TSRLL, Chlorantine Fast Grey 2BLL (all 810 compounds, whereby the fastness to wet Schultz su vol 1 e 79) treatment, in particular the fastness to washing, Dag as a rule is still further improved. In both cases, Example 2 ggg gg gfig g m light may be unfavwr' A material composed of 70% wool and 30% 5 viscose-rayon staple fibre is dyed by known meth- It has now been found that this disadvantage Dds with 4% Chlorantine Brown BRLL (Schultz, may be eliminated if an aitertreatment with copsupp. vol. 1, page 79) rinsed, hydro-extracted, per salts is combined with the aftertreatment and impregnated at room temperature with a with the aqueous solution of the high-molecular solution contamin litre condensation products from formaldehyde and g per nitrogen-containing compounds. These com- 30 parts by weight of a, y a d o mflldebined treatments can be carried out one after hyde condensation product, obtained by conthe other in any desired order; it is however, densation of 2'mols dicyandiamide with 3 mols preferable to unite them, so that the dyeings commercial formaldehyde and the prints are treated at the same time with 15 parts by weight of formic acid 85% and the organic and the copper compounds, for exam- 5 parts by weight of copper chloride,
ened for 1 hour at 90 C. Adyeing possessing good fastness properties is obtained.
Example 3 A dyeing of Chlorantine Fast Orange TGLL on cotton material is impregnated with a solution containing per 100 parts water, 16 parts dimethylol-urea, 1 part ammonium phosphate, and 1 part copper chloride (the parts being by weight) and is then dried at 110 (2., whereby the fastness of the dyeing to wet treatments is increased by the high-molecular compound formed. When the thus aftertreated dyeing is exposed to light, it exhibits a better fastness to light than a dyeing aftertreated in the same manner but with exclusion of the copper salt.
A similar result is obtained when Chlorantine Fast Orange TGLL is replaced by Chlorantine Fast Bordeaux B or by Chlorantine Fast Blue 3RLL.
What we claim is:
1. Improvement in the process of increasing the i'astness properties of dyeings and prints, which have been obtained by means of a watersoluble dyestufi and aftertreatment with a highmolecular organic compound, produced by condensation of formaldehyde with a compound containing at least once the group N... N=Cq consisting in combining the aftertreatment with a simultaneous treatment with a solution of a copper compound in the same bath.
2. Improvement in the process of increasing the fastness properties of dyeings and prints, which have been obtained by means of a water-soluble dyestufi and aftertreatment with a high-molecular organic compound, produced by the condensation of formaldehyde with melamine, consisting in combining the aftertreatment with a simultaneous treatment with a solution of a copper compound in the same bath.
3. Improvement in the process oi increasing the i'astness properties of dyeings and prints, which have been obtained by means of a water-soluble dyestufl. and aftertreatment with a high-molecular organic compound, produced by condensation of formaldehyde with a compound containing at least once the group solubie dyestufls and aftertreatment with a high- 4 molecular organic compound, produced by the condensation of formaldehyde with melamine, consisting in combining the aftertreatment with a simultaneous treatment with a solution of a copper compound in the same bath, and then subjecting the material thus treated to a dry treatment at raised temperature.
5. A textile colored witha water-soluble dyestufl and aftertreated simultaneously with a highmolecular organic compound, produced by condensation of formaldehyde with a compound containing at least once the group and with a solution of a copper compound, the wet-fastness of the aftertreated textile being superior and the light fastness thereof being of a magnitude at least equal to that of the untreated colored textile.
ALBERT LANDOLT.
ANDREAS RUPER'II.
US340200A 1938-12-21 1940-06-12 Process for improving the dyeings and prings prepared with watersoluble dyestuffs Expired - Lifetime US2364726A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
GB13277/40A GB536480A (en) 1938-12-21 1939-10-12 A process for improving dyeing and prints obtained by means of water soluble dyestuffs
DEG101004D DE767276C (en) 1938-12-21 1939-12-03 Process for improving the fastness properties of dyeings or prints with water-soluble direct dyes on cellulose fibers and fiber mixtures thereof
FR862209D FR862209A (en) 1938-12-21 1939-12-11 Improved dyes and prints obtained with water soluble dyes
FR865903D FR865903A (en) 1938-12-21 1940-05-30 Process for improving the lightfastness of dyed materials
US340200A US2364726A (en) 1938-12-21 1940-06-12 Process for improving the dyeings and prings prepared with watersoluble dyestuffs
BE474397D BE474397A (en) 1938-12-21 1947-07-08
NL133450A NL65947C (en) 1938-12-21 1947-07-14

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH536480X 1938-12-21
US29939039A 1939-10-13 1939-10-13
US340200A US2364726A (en) 1938-12-21 1940-06-12 Process for improving the dyeings and prings prepared with watersoluble dyestuffs

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US2364726A true US2364726A (en) 1944-12-12

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US (1) US2364726A (en)
BE (1) BE474397A (en)
DE (1) DE767276C (en)
FR (2) FR862209A (en)
GB (1) GB536480A (en)
NL (1) NL65947C (en)

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2432542A (en) * 1944-07-13 1947-12-16 Du Pont Method of producing coated cellulosic sheets
US2435591A (en) * 1943-01-06 1948-02-10 Chem Ind Basel Tendering properties of textiles dyed with yellow to orange vat dyestuffs by treatment with certain nitrogenous resins
US2456567A (en) * 1944-09-01 1948-12-14 Monsanto Chemicals Aminotriazine product
US2526106A (en) * 1950-10-17 Composition comprising a nitroge
US2527839A (en) * 1945-06-30 1950-10-31 Sharples Chemicals Inc Sugar carbamates and resinous condensation products therefrom
US2576241A (en) * 1950-04-03 1951-11-27 Dan River Mills Inc Dye fixing product and process and treating of textiles therewith
US2631920A (en) * 1948-11-24 1953-03-17 Ciba Ltd Compositions for the improvement of fastness properties of dyeings and printings of water-soluble dyestuffs
US2649354A (en) * 1947-12-01 1953-08-18 Sandoz Ltd Process for improving fastiness properties of direct dyestuffs
US2768055A (en) * 1952-11-15 1956-10-23 Gen Aniline & Film Corp Composition for aftertreatment of dyeings
US2880052A (en) * 1954-05-17 1959-03-31 Celanese Corp Dyeing cellulose derivatives and aftertreating for improved washfastness
US2902472A (en) * 1955-03-08 1959-09-01 Arkansas Company Inc Production of dicyandiamide triethylene tetramine formaldehyde condensate
US2921945A (en) * 1954-05-17 1960-01-19 Celanese Corp Yellow diphenylamine dyes
US2922796A (en) * 1954-05-17 1960-01-26 Celanese Corp Yellow sulfonamide dyestuff
US2981704A (en) * 1956-04-12 1961-04-25 American Cyanamid Co Water repellent, method of impregnating textiles with same, and textiles bearing same
US3000863A (en) * 1956-05-04 1961-09-19 American Cyanamid Co Dye fixing agent

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE918743C (en) * 1948-11-24 1954-10-04 Ciba Geigy Process for improving the fastness properties of dyeings or prints, produced from water-soluble dyes

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE615799C (en) * 1929-10-09 1935-07-13 I G Farbenindustrie Akt Ges Process for the production of azo dyes
GB427089A (en) * 1932-07-12 1935-04-12 Deutsche Hydrierwerke Ag Improvements in and relating to the dyeing of textiles
GB429209A (en) * 1934-02-09 1935-05-27 Chem Ind Basel Improvements relating to processes of dyeing with direct dyestuffs
FR826631A (en) * 1936-09-17 1938-04-06 Ste Ind Chim Bale Process for the improvement of industrial products, improved products, baths and preparations for the improvement of these products

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2526106A (en) * 1950-10-17 Composition comprising a nitroge
US2435591A (en) * 1943-01-06 1948-02-10 Chem Ind Basel Tendering properties of textiles dyed with yellow to orange vat dyestuffs by treatment with certain nitrogenous resins
US2432542A (en) * 1944-07-13 1947-12-16 Du Pont Method of producing coated cellulosic sheets
US2456567A (en) * 1944-09-01 1948-12-14 Monsanto Chemicals Aminotriazine product
US2527839A (en) * 1945-06-30 1950-10-31 Sharples Chemicals Inc Sugar carbamates and resinous condensation products therefrom
US2649354A (en) * 1947-12-01 1953-08-18 Sandoz Ltd Process for improving fastiness properties of direct dyestuffs
US2631920A (en) * 1948-11-24 1953-03-17 Ciba Ltd Compositions for the improvement of fastness properties of dyeings and printings of water-soluble dyestuffs
US2576241A (en) * 1950-04-03 1951-11-27 Dan River Mills Inc Dye fixing product and process and treating of textiles therewith
US2768055A (en) * 1952-11-15 1956-10-23 Gen Aniline & Film Corp Composition for aftertreatment of dyeings
US2880052A (en) * 1954-05-17 1959-03-31 Celanese Corp Dyeing cellulose derivatives and aftertreating for improved washfastness
US2921945A (en) * 1954-05-17 1960-01-19 Celanese Corp Yellow diphenylamine dyes
US2922796A (en) * 1954-05-17 1960-01-26 Celanese Corp Yellow sulfonamide dyestuff
US2902472A (en) * 1955-03-08 1959-09-01 Arkansas Company Inc Production of dicyandiamide triethylene tetramine formaldehyde condensate
US2981704A (en) * 1956-04-12 1961-04-25 American Cyanamid Co Water repellent, method of impregnating textiles with same, and textiles bearing same
US3000863A (en) * 1956-05-04 1961-09-19 American Cyanamid Co Dye fixing agent

Also Published As

Publication number Publication date
GB536480A (en) 1941-05-15
BE474397A (en) 1947-08-30
DE767276C (en) 1952-04-07
NL65947C (en) 1950-06-15
FR865903A (en) 1941-06-18
FR862209A (en) 1941-03-01

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