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US4399068A Expired / Lapsed US ⏱️ 0.0 years remaining

Concentrated, aqueous solutions of salts of acetoacetylamino-arylsulphonic acids and method of forming concentrated solutions of azo dyestuffs therefrom

Assignee: Bayer AG
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Filing: 1978-01-18
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Granted: 1983-08-16
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Expires: 1998-01-18
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Abstract

Abstract Salts of acetoacetylamino-arylsulphonic acids, of the formula ##STR1## wherein R denotes an optionally substituted benzene or naphthalene nucleus, Me denotes a protonated, tertiary, hydrophilizing nitrogen base or the lithium cation and m denotes 1,2 or 3 are easily obtained by reacting compounds of the formula H.sub.2 N--R--(SO.sub.3 H).sub.m wherein R and m have the above mentioned meaning, with diketene in an aqueous or aqueous-organic solvent maintaining a pH>3 during the reaction by adding tertiary, hydrophilizing nitrogen bases or a basic lithium salt. The salts can be obtained as concentrated solutions which are easily reacted with diazotized aromatic amines to concentrated solutions of azo dyestuffs.

Inventors

  • 👤 Erich Kramer

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 18:04
CPC Classifications
C; C09; C09B; C09B29/00; C09B29/0003; C09B29/0011; C09B29/32; C09B29/33; C09B29/331; C09B29/332; C09B31/00; C09B31/02; C09B31/10; C09B31/11; C09B31/115; C09B33/00; C09B33/02; C09B67/00; C09B67/0071; C09B67/0072; C09B67/0073; Y; Y10; Y10S; Y10S534/00; Y10S534/01

Claims Analysis

Total Claims: 5
Claim 1
Independent Claim 248 words
Process for the preparation of a concentrated dyestuff solution substantially free from foreign ions comprising (a) reacting a compound of the formula H.sub.2 N--R--(SO.sub.3 H).sub.m wherein R is benzene or naphthalene unsubstituted or substituted with fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylcarbonylamino, C 1 -C 4 -alkylsulphonylamino, phenylazo, naphthylazo, or phenylazo or naphthlazo substituted by methyl, methoxy, chloride, or nitro or is benzene substituted with carboxylcarbonylamino; and m is 1, 2 or 3; with diketene in an aqueous or aqueous-organic solvent while maintaining a reaction pH>3 by adding an amine of the formula ##STR16## wherein R 1 is hydroxyalkyl, alkoxyalkyl or --(C 2 H 4 O) n --R 4 ; R 2 and R 3 are alkyl, hydroxyalkyl, alkoxyalkyl or --(C 2 H 4 O) n --R 4 , or, together with the N atom, are pyrrolidine, morpholine, or piperazine; or by adding an ammonium hydroxide containing a cation of the formula ##STR17## wherein R 1 , R 2 and R 3 are as defined above and R 5 is R 2 or R 3 , to form a concentrated salt solution substantially free from foreign ions of the coupling component of the formula .sub.m (Me.sup.⊕⊖ O.sub.3 S)--R--NHCO--CH.sub.2 --CO--CH.sub.3 wherein Me is ##STR18## (b) reacting the resultant concentrated salt solution with a diazotized amine of the formula A--NH.sub.2 wherein A is the radical of a diazo component to form a concentrated solution of the corresponding azo dyestuff.
Claim 2
Dependent Claim 248 words
Process for the preparation of a concentrated dyestuff solution substantially free from foreign ions comprising (a) reacting a compound of the formula H.sub.2 N--R--(SO.sub.3 H).sub.m wherein R is benzene or naphthalene unsubstituted or substituted with fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylcarbonylamino, C 1 -C 4 -alkylsulphonylamino, phenylazo, naphthylazo, or phenylazo or naphthlazo substituted by methyl, methoxy, chloride, or nitro or is benzene substituted with carboxylcarbonylamino; and m is 1, 2 or 3; with diketene in an aqueous or aqueous-organic solvent while maintaining a reaction pH>3 by adding an amine of the formula ##STR16## wherein R 1 is hydroxyalkyl, alkoxyalkyl or --(C 2 H 4 O) n --R 4 ; R 2 and R 3 are alkyl, hydroxyalkyl, alkoxyalkyl or --(C 2 H 4 O) n --R 4 , or, together with the N atom, are pyrrolidine, morpholine, or piperazine; or by adding an ammonium hydroxide containing a cation of the formula ##STR17## wherein R 1 , R 2 and R 3 are as defined above and R 5 is R 2 or R 3 , to form a concentrated salt solution substantially free from foreign ions of the coupling component of the formula .sub.m (Me.sup.⊕⊖ O.sub.3 S)--R--NHCO--CH.sub.2 --CO--CH.sub.3 wherein Me is ##STR18## (b) reacting the resultant concentrated salt solution with a diazotized amine of the formula A--NH.sub.2 wherein A is the radical of a diazo component to form a concentrated solution of the corresponding azo dyestuff.
Claim 3
Dependent Claim 64 words
The process of claim 1, wherein m is one, the pH of the reaction is maintained by adding the amine or the ammonium hydroxide and the resulting concentrated solution of the coupling component is reacted with a diazonium betaine of the formula .sup.⊖ O.sub.3 S--A'--N.sub.2.sup.⊕ wherein A is the radical of a diazo component, to form a concentrated solution of the corresponding azo dyestuff.
Claim 4
Dependent Claim 26 words
A concentrated solution of the dyestuff of the formula ##STR19## prepared according to claim 1, wherein R 6 is R 2 , R 3 or hydrogen.
Claim 5
Dependent Claim 12 words
A concentrated solution according to claim 3 wherein the solvent is water.

References Cited (Backward Citations)

US2310181A Cited
US3274171A Cited
US3313665A Cited
US4001206A Cited
US3925375A Cited
US4014926A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1986-08-15 1987-02-14 1987-08-16 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1990-08-15 1991-02-14 1991-08-16 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1994-08-15 1995-02-14 1995-08-16 $7700.00 Window Closed / Lapsed

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