GB1565180A - Creation of Inventions and Patents with Artificial Intelligence

GB1565180A – Stabillisation of anionic indole dyestuffs
– Google Patents

GB1565180A – Stabillisation of anionic indole dyestuffs
– Google Patents
Stabillisation of anionic indole dyestuffs

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Publication number
GB1565180A

GB1565180A
GB6643/78A
GB664378A
GB1565180A
GB 1565180 A
GB1565180 A
GB 1565180A
GB 6643/78 A
GB6643/78 A
GB 6643/78A
GB 664378 A
GB664378 A
GB 664378A
GB 1565180 A
GB1565180 A
GB 1565180A
Authority
GB
United Kingdom
Prior art keywords
optionally substituted
alkyl
denotes
radical
formula
Prior art date
1977-02-25
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

Application number
GB6643/78A
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.)

Bayer AG

Original Assignee
Bayer AG
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.)
1977-02-25
Filing date
1978-02-20
Publication date
1980-04-16

1978-02-20
Application filed by Bayer AG
filed
Critical
Bayer AG

1980-04-16
Publication of GB1565180A
publication
Critical
patent/GB1565180A/en

Status
Expired
legal-status
Critical
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Classifications

C—CHEMISTRY; METALLURGY

C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR

C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES

C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films

C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions

C09B67/0072—Preparations with anionic dyes or reactive dyes

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

D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated

D06P3/02—Material containing basic nitrogen

D06P3/04—Material containing basic nitrogen containing amide groups

D06P3/24—Polyamides; Polyurethanes

D06P3/241—Polyamides; Polyurethanes using acid dyes

Description

PATENT SPECIFICATION ( 11) 1 565 180
3 ( 21) Application No 6643/78 ( 22) Filed 20 Feb 1978 X ( 31) Convention Application No 2708188 ( 19) o ( 32) Filed 25 Feb1977 in U ( 33) Federal Republic of Germany (DE) 3 ( 44) Complete Specification published 16 April 1980 ( 5 I) INT CL 3 D 06 P 1/642 ( 52) Index at acceptance DIB 2 F 2 L 13 2 L 29 A 2 L 29 B 2 L 2 A 2 L 30 A 2 L 32 A 2 L 5 D 2 L 6 2 L 7 2 L 8 ( 72) Inventors HERBERT HUGL, HANS-GUNTER OTTEN, HANS WERNER PETROLL and KARLHEINZ WOLF ( 54) STABILISATION OF ANIONIC INDOLE DYESTUFFS ( 71) We, BAYER AKTIENGESELLSCHAFT a body corporate organised under the laws of Federal Republic of Germany of 509 Leverkusen-Bayerwerk, Germany, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement: 5
Azo dyestuffs which contain, as the coupling component, an indole of the formula R wherein R denotes an optionally substituted alkyl radical, an optionally substituted aryl 10 radical or an optionally substituted aralkyl radical, and the benzene ring A can be further substituted, in particular those in which R denotes a C,-C 4-alkyl radical and the benzene ring A is not further substituted or is further substituted by methyl, methoxy, chlorine, bromine or 15 sulpho, frequently exhibit an undesired irreversible change in the colour shade in acid solutions, which noticeably impairs the use of the otherwise very valuable and highly fast dyestuffs.
The adverse effect always occurs, above all, when the dyestuffs are kept for a 20 prolonged period or at elevated temperature in solutions which have been rendered acid, for example dye liquors or printing plates This can be the case, for example, in continuous dyeing or in the printing of polyamide carpet materials.
According to the present invention we provide a process for preventing irreversible colour shade of the above mentioned azo dyestuffs by adding nitrogen 25 containing complex-forming substances which correspond to the general formula R.-N-R 3 wherein R 1 and R 2 denote hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted hetaryl or optionally 30 substituted aralkyl, or together, with the inclusion of the N atom, denote a heterocyclic ring and R 3 denotes optionally substituted alkyl, optionally substituted aralkvl, optionally substituted hetaryl or a radical of the formula (C Hi)n -N Cc Z N 2) i J zl (Ila) wherein R, and R 2 have the abovementioned meaning, R 4 denotes hydrogen, optionally substituted alkyl or optionally substituted alkenyl, N denotes an integer from 1 to 3, 5 p denotes an integer from 0 to 8, m denotes an integer from 1 to 4, q denotes the integer I or 2 and t denotes the integer 0 or 1, the sum of q and t being 2 10 Suitable alkyl radicals R are those with I to 4 C atoms, which can be further substituted, for example, by cyano, aminocarbonyl, amino or carboxyl Possible substituents of the benzene ring A are, in particular, chlorine, bromine, C,-C 4alkyl, C 1-C 4-alkoxy, cyano or sulpho.
The alkyl and alkenyl radicals R, to R 4 preferably contain I to 30 C atoms 15 and can contain, as substituents, hydroxyl, C,-C 4-alkoxy, carboxyl or polyether groups of the formula -(-CH-CH-O-)-L-R 7 I I (lib) R 5 R 6 wherein Rs and R 6 denote hydrogen or methyl, 20 R 7 denotes hydrogen or C 1-C 4-alkyl and r denotes an integer from 1-40.
Suitable aryl R 1, R 2 and R 3 is, in particular, phenyl which is optionally substituted by halogen, hydroxy, C 1-C 12-alkyl or C 1-C 12-alkoxy Suitable aralkyl R 1, R 2 and R 3 is phenyl-C 1-C 4-alkyl which is optionally substituted in the phenyl 25 nucleus by C 1-C 4-alkyl, C 1-C 4-alkoxy or halogen Suitable hetaryl R 1, R 2 and R 3 is, for example, pyridin-2-yl Suitable heterocyclic rings, which R, and R 2 can form together, with the inclusion of the N atom, are, for example, morpholine piperidine and piperazine.
Preferred compounds of the formula (II) are, in particular, nitrilotriacetic 30 acid, ethylenediaminetetraacetic acid, diethylenetriaminepentaacetic acid, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine and N( 2amino-ethyl)-piperazine.
The stabilising agent is used in an amount of 5 to 50 % , by weight, preferably 20 to 40 %,, by weight, relative to the weight of the dyestuff The action of the stabilising 35 agent can be even further increased by also using non-ionic surfaceactive agents.
Examples of these which come are substances of the formula Rto 82-tr o -H(ml) wherein R 8 denotes C 4-C 12-alkyl and 40 s denotes 10 to 40, or Rg O-(-CH 2 CH 2 O)u H (IV) wherein R 9 denotes an optionally unsaturated C 12-C 20-alkyl radical and 45 u denotes 20 to 50.
These surface-active agents are optionally also used in a concentration of 0 3 to 10 g per litre, preferably 0 5 to 3 g per litre The amount of the dyestuff in the acid solution is 0 02 to 5 g per litre.
The invention further relates to dyestuff formulations which contain 20 to 80 %, 50 by weight of a dyestuff of the formula D-N =N-H (V) R wherin D denotes the radical of a diazo component and A and R have the abovementioned meaning, 55 1,565,180 D, A and R being chosen so that the dyestuff contains at least one acid group, to 30 ‘,, by weight of a compound of the formula (II) and 0 to 750,, by weight of further customary formulating agents Customary formulating agents are, for example inorganic salts, such as Na CI or Na 2 SO 4, dextrin, anionic dispersing agents and polyvinyl alcohol 5 The process according to the invention is particularly effective in the case of dyestuffs which contain 2-methylindole as coupling components Nitrilotriacetic acid, ethylenediaminetetraacetic acid and diethylenetriaminepentaacetic acid are particularly suitable additives for such dyestuffs The compounds can be employed either in the form of the free acid or in the form of their salts, preferably the alkali 10 metal salts.
Dyestuffs of the formula (V) to which the process according to the invention can be applied are known, for example, from British Patent Specifications
1,316,724, 1,328,774, 1,384,472, 1,430,899 and 1,457,231 and from U S Patent Is Specifications 3,956,267, 3,883,502, 3,867,369, 3,891,619 and 3,925, 350 15
The process which follows has proved to be a practicable test method for evaluating and avoiding the undesired colour change; The dyestuff is kept in an acid solution at p H 4 for 6 hours at 80 WC, with and without the addition of the stabilising agent Dyeings are produced from these solutions on nylon 6 in the customary manner and are compared visually, both with 20 one another and with dyeings which have been obtained in the same manner from freshly prepared solutions For better differentiation, 0 4 o^ of C I Acid Blue 40 and 0 4 of C I Acid Red 337 are added, in the case of each dyeing, as contrast dyestuffs.
The concentration of the dyestuff investigated is, depending on the dyestuff, 25 up to I %,, relative to the weight of the material Instead of the dyestuffs and stabilising agents, it is also possible to investigate dyestuff formulations which contain the given stabilising agent or in which the stabilising agent is lacking, and which optionally contain further customary formulating agents.
Example 1 30
0.2 g of the dyestuff of the formula -N HOS-CHZ-CHL-NH-W Ot CH 3 are dissolved in soft water (German hardness=O), together with 0 03 g of the tetrasodium salts of ethylenediaminetetraacetic acid as the stabilising agent The solution is adjusted to p H 4 with secondary sodium phosphate and acetic acid and 35 is made up to 125 ml with soft water.
The solution is warmed to a temperature of 800 C for 6 hours A dyebath is prepared using an appropriate proportion of this solution and the dyestuffs Acid Blue 40 and Acid Red 337, and nylon 6 is dyed with this in the customary manner.
The dyebath contains, relative to the weight of the material, 0 4 ,, of Acid Blue 40, 40 0.3 % of Acid Red 337 and 0 4 cc of the indole dyestuff described above.
A brown dyeing results in which the yellow component appears significantly more strongly than in the case of a comparison dyeing, for the preparation of which the yellow dyestuff was pre-treated if the same manner, but without a stabilising agent 45 Example 2
Example I is repeated, the dyestuff of the formula HO S-CHZ-C Hr N H-OS IN N= H C, having been employed as the indole dyestuff this time As in Example I, a brown dyeing with a significantly stronger yellow component than in the case of a 50 comparison dyeing, for the preparation of which the indole dyestuff was pretreated without a stabilising agent, results.
Commercial strength, relative to the weight of the material.
1,565,180 Example 3
Example I is repeated, the dyestuff of the formula CF 3 i N N-N CH 3 having been employed as the indole dyestuff In the resulting brown dyeing, the yellow component appears significantly more strongly than in the case of a 5 comparison dyeing which was obtained without the stabilising agent, but otherwise in the same manner.
Example 4
Example I is repeated, 0 03 g of tetraethylenepentamine together with 0 625 g of the emulsifier of the formula 10 n-Hqcq o cz c Ho C z O H being used as the stabilising agent as the stabilising agent Compared with Example’ I, the stabilisation of the indole dyestuff is improved even further.
Similar results are achieved when the dyestuffs from Examples 2 and 3 are employed in Example 4 15 Example 5
Example 2 is repeated, 0 3 g of an already stabilised formulation of the same dyestuff having a composition of 70 ,, by weight of pure dyestuff, 10 ,, by weight of the pentasodium salt of diethylenetriaminepentaacetic acid, 5 ‘,/ by weight of lithium hydroxide and 15 ,, by weight of the sodium salt of the formaldehyde 20 condensate of ditolyl ether-sulphonic acid, being employed instead of the indole dyestuff and the stabilising agent The comparison result is comparable to the result from Example 2.

Claims (1)

WHAT WE CLAIM IS:-
1 Process for preventing irreversible changes in the colour shade of azo 25 dyestuffs, which contain, as the coupling component, an indole of the formula (I) R wherein R denotes an optionally substituted alkyl radical, an optionally substituted aryl radical or an optionally substituted aralkyl radical and the benzene ring A can be 30 further substituted, in acid solution, characterised in that nitrogen-containing complexforming substances which correspond to the general formula R.-N-Ra I (II) R 2 wherein 35 R, and R 2 denote hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted hetaryl or optionally substituted aralkyl, or together, with the inclusion of the N atom, denote a heterocyclic ring and R 3 denotes optionally substituted alkyl, optionally substituted aralkyl,
40 optionally substituted hetaryl or a radical of the formula:
CCH 2)n -N (CHZ)t NAR ( 11 a) L L l% ‘{Rzt Rl A 1,565,180 wherein R 1 and R 2 have the abovementioned meaning.
R 4 denotes hydrogen, optionally substituted alkyl or optionally substituted alkenyl, N is 1, 2 or 3, 5 p is 0 or an integer from I to 8, m is 1, 2, 3 or 4, q is I or 2 and t is O or 1, the sum of q and t being 2, are added 10 2 Process according to Claim 1, characterised in that nitrogen-containing complex-forming substances which are used are those of the formula II wherein R, and R 2 denote hydrogen, a C,-C 30-alkyl or C,-C 30-alkenyl radical which is optionally substituted by hydroxyl, C,-C 4-alkoxy, carboxyl or a polyether group of the formula 15 -(-CH-CH-O-)r-R 7 I I (l Ib) Rs R 6 wherein Rs and R 6 denote hydrogen or methyl, R 7 denotes hydrogen or C,-C 4-alkyl and r denotes an integer from I-40, 20 a phenyl radical which is optionally substituted by halogen, hydroxyl, C,C,2-alkyl or C,-C,2-alkoxy, a pyridin-2-yl radical or a phenyl-C C 4-alkyl radical which is optionally substituted in the phenyl nucleus by C,-C 4-alkyl, C,-C 4alkoxy or halogen, or R, and R 2 denote, with the inclusion of the N atom, morpholinyl, piperidinyl or piperazinyl and R 3 denotes a C,-C 30-alkyl group which is optionally 25 substituted by hydroxyl, C,-C 4-alkoxy, carboxyl or a polyether group of the above mentioned formula (l Ib), a phenyl-C C 4-alkyl radical which is optionally substituted one phenyl nucleus by C,-C 4-alkyl, C,-C 4-alkoxy or halogen, a piperidin-2-yl radical or a radical of the formula (lla) as defined in Claim 1.
3 Process according to Claim 1, characterised in that nitrilotriacetic acid, 30 ethylenediaminetetraacetic acid, diethylenetriaminepentaacetic acid, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine and N( 2amino-ethyl)-piperizine are used as the nitrogen-containing complexforming substances.
4 Process according to Claim I, characterised in that the nitrogencontaining 35 complex-forming substances are added to those azo dyestuffs which contain, as the coupling component, an indole of the formula 9 H R wherein R denotes C,-C 4-alkyl which is optionally substituted by cyano, 40 aminocarbonyl, amino or carboxyl and the benzene ring A is optionally substituted by chlorine, bromine, C,-C 4-alkyl, C,-C 4-alkoxy, cyano or sulpho.
Process according to Claim 4, wherein R denotes C,-C 4-alkyl and the benzene ring A is not further substituted or is further substituted by methyl, methoxy, chlorine, bromine or sulpho 45 6 Process according to Claim I for preventing irreversible changes in the colour shade of azo dyestuffs, which contain, as the coupling component, 2methylindole, characterised in that nitrilotriacetic acid, ethylenediaminetetraacetic acid and diethylenetriaminepentaacetic acid are added as the nitrogen-containing complex-forming subtance 50 7 Process according to Claim 1, characterised in that the nitrogencontaining complex-forming compounds are added in an amount of 5 to 50 % by weight, relative to the weight of the dyestuff.
8 Process according to Claim 1, characterised in that non-ionic surfaceactive agents are additionally added 55 9 Process according to Claim 1, characterised in that surface-active agents of the formula Rs 6-(jo (ci-c o H 1,565,180 wherein R 8 denotes C 4 to C,2-alkyl and s denotes a number from 10 to 40, or of the formula Rg-O (-CH 2-CH 2-O-)r-H 5 wherein R 9 denotes an optionally unsaturated C 12 to C 20-alkyl radical and u denotes a number from 20 to 50, are additionally added.
10 Process according to Claim 8, characterised in that the non-ionic surface 10 active agents are added in an amount of 0 3 to 10 g per litre of the acid solution.
11 Process according to Claim 1, characterised in that those solutions which contain the azo dyestuff in a concentration of 0 02 to 5 g per litre are treated.
12 Dyestuff formulations, characterised in that they contain 20-80/,, by weight of a dyestuff of the formula 15 D -N =NYH R wherein D denotes the radical of a diazo component and A and R have the meaning given in Claim 1, D, A and R being chosen so that the dyestuff contains at leat one acid group, 20 to 30 % , by weight of the nitrogen-containing complex-forming subtance as defined in Claim I and 0 to 75 % by weight of further customary formulating agents.
For the Applicants:
CARPMAELS & RANSFORD, Chartered Patent Agents, 43 Bloomsbury Square, London, WCIA 2 RA.
Printed for Her Majesty’s Stationery Office, by the Courier Press, Leamington Spa 1980 Published by The Patent Office, 25 Southampton Buildings, London, WC 2 A l AY, from which copies may be obtained.
1,565,180 A

GB6643/78A
1977-02-25
1978-02-20
Stabillisation of anionic indole dyestuffs

Expired

GB1565180A
(en)

Applications Claiming Priority (1)

Application Number
Priority Date
Filing Date
Title

DE2708188A

DE2708188C2
(en)

1977-02-25
1977-02-25

Stabilization of anionic indole dyes

Publications (1)

Publication Number
Publication Date

GB1565180A
true

GB1565180A
(en)

1980-04-16

Family
ID=6002156
Family Applications (1)

Application Number
Title
Priority Date
Filing Date

GB6643/78A
Expired

GB1565180A
(en)

1977-02-25
1978-02-20
Stabillisation of anionic indole dyestuffs

Country Status (9)

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US
(1)

US4245995A
(en)

JP
(1)

JPS53105530A
(en)

BE
(1)

BE864303A
(en)

BR
(1)

BR7801125A
(en)

DE
(1)

DE2708188C2
(en)

ES
(1)

ES467278A1
(en)

FR
(1)

FR2401198B1
(en)

GB
(1)

GB1565180A
(en)

IT
(1)

IT7820531D0
(en)

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Monoazo dyes and processes for dyeing and printing

1977

1977-02-25
DE
DE2708188A
patent/DE2708188C2/en
not_active
Expired

1978

1978-02-09
US
US05/876,514
patent/US4245995A/en
not_active
Expired – Lifetime

1978-02-20
GB
GB6643/78A
patent/GB1565180A/en
not_active
Expired

1978-02-22
IT
IT7820531A
patent/IT7820531D0/en
unknown

1978-02-23
JP
JP1914278A
patent/JPS53105530A/en
active
Pending

1978-02-24
ES
ES467278A
patent/ES467278A1/en
not_active
Expired

1978-02-24
BR
BR7801125A
patent/BR7801125A/en
unknown

1978-02-24
BE
BE185465A
patent/BE864303A/en
unknown

1978-02-24
FR
FR7805355A
patent/FR2401198B1/fr
not_active
Expired

Cited By (2)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

EP0479726A1
(en)

1990-10-04
1992-04-08
Ciba-Geigy Ag
Concentrated aqueous solutions of anionic disazo dyes

US5211719A
(en)

1990-10-04
1993-05-18
Ciba-Geigy Corporation
Concentrated acqueous solutions of anionic disazo dyes with polyglycol-amine

Also Published As

Publication number
Publication date

FR2401198B1
(en)

1982-11-19

FR2401198A1
(en)

1979-03-23

BR7801125A
(en)

1978-10-10

BE864303A
(en)

1978-08-24

DE2708188B1
(en)

1978-06-15

ES467278A1
(en)

1978-10-16

JPS53105530A
(en)

1978-09-13

IT7820531D0
(en)

1978-02-22

US4245995A
(en)

1981-01-20

DE2708188C2
(en)

1979-02-08

Información de contacto