US2190848A - Dyeings - Google Patents

Dyeings Download PDF

Info

Publication number
US2190848A
US2190848A US143726A US14372637A US2190848A US 2190848 A US2190848 A US 2190848A US 143726 A US143726 A US 143726A US 14372637 A US14372637 A US 14372637A US 2190848 A US2190848 A US 2190848A
Authority
US
United States
Prior art keywords
dyeings
complex
compound
fibers
copper
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
US143726A
Inventor
Petersen Siegfried
Taube Carl
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.)
GAF Chemicals Corp
Original Assignee
General Aniline and Film 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
Application filed by General Aniline and Film Corp filed Critical General Aniline and Film Corp
Priority to US254010A priority Critical patent/US2218924A/en
Application granted granted Critical
Publication of US2190848A publication Critical patent/US2190848A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/06—Preparatory processes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B23—MACHINE TOOLS; METAL-WORKING NOT OTHERWISE PROVIDED FOR
    • B23K—SOLDERING OR UNSOLDERING; WELDING; CLADDING OR PLATING BY SOLDERING OR WELDING; CUTTING BY APPLYING HEAT LOCALLY, e.g. FLAME CUTTING; WORKING BY LASER BEAM
    • B23K11/00—Resistance welding; Severing by resistance heating
    • B23K11/08—Seam welding not restricted to one of the preceding subgroups
    • B23K11/087—Seam welding not restricted to one of the preceding subgroups for rectilinear seams
    • B23K11/0873—Seam welding not restricted to one of the preceding subgroups for rectilinear seams of the longitudinal seam of tubes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General 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
    • D06P1/44—General 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
    • D06P1/64—General 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
    • D06P1/642—Compounds containing nitrogen
    • D06P1/6426—Heterocyclic compounds
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General 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
    • D06P1/44—General 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
    • D06P1/64—General 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
    • D06P1/642—Compounds containing nitrogen
    • D06P1/645—Aliphatic, araliphatic or cycloaliphatic compounds containing amino groups
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General 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
    • D06P1/44—General 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
    • D06P1/64—General 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
    • D06P1/642—Compounds containing nitrogen
    • D06P1/649—Compounds containing carbonamide, thiocarbonamide or guanyl groups
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/916—Natural fiber dyeing
    • Y10S8/918—Cellulose textile

Definitions

  • the present invention relates to a process oiimproving dyeings on textile fibers and similar material.
  • dyeings' of organic dyestuffs can be improved by causing the said dyestuffs to interact on the dyed material with organic bases like amines, quaternary ammonium compounds or 10 soluble salts thereof.
  • organic bases like amines, quaternary ammonium compounds or 10 soluble salts thereof.
  • the metal complex compounds to be used according to our invention are derived from or- 40 ganic bases which may belong to the aliphatic or cyclic series.
  • the metal complex compounds of guanidino guanidine, oi thiourea, of c-phenanthroline, of phenylene diamines, or -2.2'-dipyridyl, of 8- amino-quinoline, oi 8-amino-quinaldine and the like.
  • the metals suitable for preparing the compounds to be used according to our invention are of the type which easily forms complex compounds with organic bases, for instance, chromium, iron and especially copper.
  • the process oi our invention may be carried out by ai'tertreating the dyed fibers withan aqueous solution oi one of the said complex metal compounds; if desired, the solution may '55 be weakly acid or alkaline.
  • the dyeing is per- The aqueous solution 01 the copper vcomplex oi the compound of the following constitution:
  • the above mentioned compound is obtainable by reacting upon 1 mol of cyanuric chloride with 1 mol of m-amino-phenyl-trimethyl am- 'moniumchloride and 1 mol of 5-amino-8-hydroxy-quinoline.
  • Example 2 A 2% dyeing on cotton with the dyestufi which is obtained by coupling in an alkaline medium diazobenzene and diazotized 2-naphthylamine-6- sulionic acid with the urea of I-acid, is treated, after washing, for half an hour at 30 C. with an aqueous solution of the complex compound pre.. pared from cupric sulfate and. B-amino-quinaldine (obtainable by stirring an alcoholic solution or B-amino-quinaldine into an aqueous cupric sulfate solution). By this treatment the scarlet red dyeing becomes dark brown and acquires a good fastness to washing.
  • Example 3 A 2% dyeing oi Diamine Pure Blue FF is dull and faster to washing.
  • Example 4 Cotton which has been dyed with 7% of Sirius Black L (comp. Schultz, Farbstofltabellen, Erganzungsband, 1934, page 132) is treated in an aqueous. solution at 30 C.- prepared from o-phenanthroline-cupric-chloride (obtainable from ophenanthroline and cupric chloride). The dyeing becomes more greenish and is improved as regards its iastness to washing.
  • Example 5 The fastness to water and washing of cotton dyeings prepared with Diamine Green B are improved on aftertreating the same with solutions of the complex salts prepared from cupric chloride with 1 or 2 mols of a.u-dipyridyl.
  • the fastness to washing of the dyeings is also improved by using the corresponding complex iron salts.
  • Example 6 Cotton dyed with Direct Deep Black EW extra is aftertreated with the solution of the cupric complex salt of NN-tetramethyl-o-phenylene-diamine.
  • Such solutions may, for instance, be obtained by adding'l mol of base and 1 mol of copper acetate in alcohol and dilution with water of this alcoholic solution which, if desired, may have been filtered.
  • the Iastness to water of the aftertreated dyeings is improved.
  • the modification which comprises causing the dyed fibers to interact with a complex metal compoundof a cyclic base containingv at least two basic nitrogen atoms which metal compound is capable 01' forming salts with acids.
  • the modification which comprises treating the dyed fibers with an aqueous solution of a complex copper compound of a N-heterocyclic base containing at least two basic nitrogen atoms which'copper compound is capable of forming salts with acids.
  • the modification which comprises treating the dyed fibers with an aqueous solution of a complex-copper compound of 8-amino-quinoline which copper compound is capable of forming salts with acids.

Description

Patented Feb; 20, 1940 UNITED STATES ramas sumac Petersen,
Le'verkusen-I. G. Werk,
Bayer, and Carl Tanbe. Germany, assignors to General Aniline & Film Corporation, a corporation 0! Delaware No Drawing. Application May 20, 1937, Serial No. 143,726. In Germany May 30, 1938 9 Claims.
The present invention relates to a process oiimproving dyeings on textile fibers and similar material. l
It is known that in many cases dyeings' of organic dyestuffs, especially such as contain tree carboxylic or sulionic acid groups, can be improved by causing the said dyestuffs to interact on the dyed material with organic bases like amines, quaternary ammonium compounds or 10 soluble salts thereof. By such processes the dyestufls are more solidly fixed on the dyed material so that the dyeings will'be of better fastness to water, to washing and the like. The
said treatment has been carried out either by aitertreating the dyedmaterial or by pretreating the material and thereafter. dyeing it with direct or acid dyestuffs. I
We have now round that still. better results are obtained by employing for .the said purpose 2 such organic bases as have combined therewith a metal incomplex form but as are still capable of forming salts with acids. By our new process, for instance, in many cases the fastness o! the dyeings to water will be materially increased whilst in these and other cases the treated dyeings will be much faster to the action of light. Moreover, often a remarkable change 'in color oi the treated dyeing has been observed thus yielding for instance a deeper shade or a'more so valuable tint of increased iastness. The process of our invention has proved to be especially suitable for improving dyeings of substantive. dyestufls on cellulosic textile fibers like cotton or artificial silk from regenerated cellulose. These and other objects and results of our invention will be more fully illustrated by the to]- lowing description thereof.
The metal complex compounds to be used according to our invention are derived from or- 40 ganic bases which may belong to the aliphatic or cyclic series. As examples we may mention the metal complex compounds of guanidino guanidine, oi thiourea, of c-phenanthroline, of phenylene diamines, or -2.2'-dipyridyl, of 8- amino-quinoline, oi 8-amino-quinaldine and the like. The metals suitable for preparing the compounds to be used according to our invention are of the type which easily forms complex compounds with organic bases, for instance, chromium, iron and especially copper.
The process oi our invention may be carried out by ai'tertreating the dyed fibers withan aqueous solution oi one of the said complex metal compounds; if desired, the solution may '55 be weakly acid or alkaline. In another modification of our" process forming of the metal complex compound and attertreating oi the dyeing is per- The aqueous solution 01 the copper vcomplex oi the compound of the following constitution:
is used for the aftertreatment of. a 2% dyeing with Diamine Pure Blue FF (comp. Col. Ind. -No. 517). On aitertreating for half an hour, which aitertreatment can also be effected in an acetic acid or an alkaline solution, there is obtained in contrast to the non-aftertreated 'solution an essentially greener shade. The aftertreated dyeing is distinguished by its fastness to washing and light.
A similarly improved fastness to waterfiand washing is obtained on aftertreating in the usual manner dyeings with Congo Red (Co. Ind. No. 370) or with Direct Deep Black EW.
The above mentioned compound is obtainable by reacting upon 1 mol of cyanuric chloride with 1 mol of m-amino-phenyl-trimethyl am- 'moniumchloride and 1 mol of 5-amino-8-hydroxy-quinoline.
Example 2 A 2% dyeing on cotton with the dyestufi which is obtained by coupling in an alkaline medium diazobenzene and diazotized 2-naphthylamine-6- sulionic acid with the urea of I-acid, is treated, after washing, for half an hour at 30 C. with an aqueous solution of the complex compound pre.. pared from cupric sulfate and. B-amino-quinaldine (obtainable by stirring an alcoholic solution or B-amino-quinaldine into an aqueous cupric sulfate solution). By this treatment the scarlet red dyeing becomes dark brown and acquires a good fastness to washing.
' On treating dyeings of Diamine Green B (comp. Col. Ind. 1st edition, No. 593) in the manner described in the preceding paragraph, these dyeings become essentially faster to washing and deeper.
Example 3 A 2% dyeing oi Diamine Pure Blue FF is dull and faster to washing.
Example 4 Cotton which has been dyed with 7% of Sirius Black L (comp. Schultz, Farbstofltabellen, Erganzungsband, 1934, page 132) is treated in an aqueous. solution at 30 C.- prepared from o-phenanthroline-cupric-chloride (obtainable from ophenanthroline and cupric chloride). The dyeing becomes more greenish and is improved as regards its iastness to washing.
Instead of the copper complex compound of ophenanthroline there can be used the copper.
complex compound of nitro-o-phenanthroline,
. which is obtainable by nitration, or of the reduction product thereof, or of the compound obtainable by causing 1 mol of 2.3-diamino-naphthalane, and 2 mols of glycerine to react according to the method of Skraup.
Example 5 The fastness to water and washing of cotton dyeings prepared with Diamine Green B are improved on aftertreating the same with solutions of the complex salts prepared from cupric chloride with 1 or 2 mols of a.u-dipyridyl.
The fastness to washing of the dyeings is also improved by using the corresponding complex iron salts.
Example 6 Cotton dyed with Direct Deep Black EW extra is aftertreated with the solution of the cupric complex salt of NN-tetramethyl-o-phenylene-diamine. Such solutions may, for instance, be obtained by adding'l mol of base and 1 mol of copper acetate in alcohol and dilution with water of this alcoholic solution which, if desired, may have been filtered. The Iastness to water of the aftertreated dyeings is improved.
A similar efiect is obtained, for instance. by the copper complex solution of N-monomethyl-ophenylenediamine.
We claim:
1. In the process of ganic dyestuffs containing free acid groups on textile fibers the modification which comprises causing the dyed fibers to interact with a complex metal compoundof a cyclic base containingv at least two basic nitrogen atoms which metal compound is capable 01' forming salts with acids.
improving dyeings of orplex copper compound of a cyclic base containing at least two basic nitrogen atoms which copper compound is capable of forming salts with acids.
4. In the process of improving dyeings 0! organic dyestuffs containing free acid groups on cellulosic fibers the modification which comprises causing the dyed fibers to interact with a complex copper compound of a cyclic organic base containing at least two basic nitrogen atoms which copper compound is capable of forming salts with acids.
5. In the process of improving dyeings of organic dyestufiscontaining free acid groups on cellulosic textile fibers the modification which comprises treating the dyed fibers with an aqueous solution of a complex copper compound of a N-heterocyclic base containing at least two basic nitrogen atoms which'copper compound is capable of forming salts with acids.
6. In the process of improving dyeings of organic dyestuffs containing free acid groups on cellulosic fibers the modification which comprises treating the dyed fibers with an aqueous solution of a complex-copper compound of 8-amino-quinoline which copper compound is capable of forming salts with acids.
7. ln'the process of improving dyeings of organic dyestuffs containing free acid groups on cellulosic textile fibers the modification which comprises treating the dyed fibers with an aqueous solution of a complex copper compound of 8-amino-quinaldine which copper compound is capable of forming salts with acids. v
8. Ifextile fibers dyed with organic dyestufis containing free acid groups, said dyed fibers 'being combined with a complex metal compound of a cyclic base containing at least two basic nitro-'
US143726A 1936-05-31 1937-05-20 Dyeings Expired - Lifetime US2190848A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US254010A US2218924A (en) 1937-05-20 1939-02-01 Aftertreatment of dyed textile fibers

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEI55142D DE657117C (en) 1936-05-31 1936-05-31 Process for improving the properties of dyeings with substantive dyes containing sulfonic acid or carboxylic acid groups on cellulose fibers
GB17579/36A GB478953A (en) 1936-05-31 1936-06-24 Process for the manufacture on the fibre of transformation products of dyestuffs containing sulphonic acid or carboxylic acid groups

Publications (1)

Publication Number Publication Date
US2190848A true US2190848A (en) 1940-02-20

Family

ID=25981937

Family Applications (1)

Application Number Title Priority Date Filing Date
US143726A Expired - Lifetime US2190848A (en) 1936-05-31 1937-05-20 Dyeings

Country Status (6)

Country Link
US (1) US2190848A (en)
BE (1) BE478953A (en)
DE (3) DE300536C (en)
FR (2) FR822252A (en)
GB (1) GB478953A (en)
NL (1) NL46452C (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3074814A (en) * 1958-01-15 1963-01-22 Ici Ltd Treatment of cellulosic materials
US3116103A (en) * 1959-09-24 1963-12-31 Ici Ltd Textile colouration process
US3211513A (en) * 1961-08-17 1965-10-12 Ciba Geigy Corp Process for dyeing and printing reactive dyestuffs
US3325242A (en) * 1967-06-13 Process for dyeing and printing with reactive dyestuffs

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2649354A (en) * 1947-12-01 1953-08-18 Sandoz Ltd Process for improving fastiness properties of direct dyestuffs
US2576241A (en) * 1950-04-03 1951-11-27 Dan River Mills Inc Dye fixing product and process and treating of textiles therewith
DE968041C (en) * 1951-05-10 1958-01-09 Bayer Ag Process for the production of copper-containing, higher molecular weight, basic condensation products
DE954686C (en) * 1953-08-17 1956-12-20 Bayer Ag Agent for improving the fastness properties of dyeings of substantive dyes on cellulose fibers

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3325242A (en) * 1967-06-13 Process for dyeing and printing with reactive dyestuffs
US3074814A (en) * 1958-01-15 1963-01-22 Ici Ltd Treatment of cellulosic materials
US3116103A (en) * 1959-09-24 1963-12-31 Ici Ltd Textile colouration process
US3211513A (en) * 1961-08-17 1965-10-12 Ciba Geigy Corp Process for dyeing and printing reactive dyestuffs

Also Published As

Publication number Publication date
GB478953A (en) 1938-01-24
BE478953A (en) 1948-01-31
DE304780C (en) 1918-04-10
DE300536C (en) 1917-09-26
FR822252A (en) 1937-12-24
NL46452C (en) 1939-08-15
FR822282A (en) 1937-12-24
DE657117C (en) 1938-02-28

Similar Documents

Publication Publication Date Title
US2190848A (en) Dyeings
US2148659A (en) Process for the production of fast tints on cellulosic fibers
US2867494A (en) Method of metallizing azoic dyeings
US2092429A (en) Dyeing vegetable fiber
US2078388A (en) Dyeing process and composition
US2156731A (en) Azo dyestuff insoluble in water and fiber dyed therewith
US2036159A (en) Manufacture of new azo dye stuff
US2526106A (en) Composition comprising a nitroge
US3098691A (en) Dyeing of polyester fiber
US3619109A (en) Cobalt-phthalocyanine-polyamine complexes for the dyeing and printing of textiles
US2218924A (en) Aftertreatment of dyed textile fibers
US2593930A (en) Process of printing fabrics with aryl sulfonhydrazides
US2093402A (en) Printing and dyeing compositions and processes
GB531470A (en) Process of dyeing
US2956853A (en) Mordant dyeing process
US2104505A (en) Dyeings on cellulosic fibers
US2115136A (en) Dyeing
US1757505A (en) Process of dyeing
US1972873A (en) Azo dye and method for its preparation
US1969464A (en) Dyeing and printing of acetate silk
US2116553A (en) Dyeing process
US2052833A (en) Process of preparing metalliferous hydroxyquinoline azo dyestuffs
US2038081A (en) Water-insoluble azo-dyestuffs and fiber dyed therewith
US2041697A (en) Azo dyes and method for their preparation
US2015204A (en) Water-insoluble azo-dyestuff and fiber dyed therewith