GB1599627A - Bleachable dyes - Google Patents
Bleachable dyes Download PDFInfo
- Publication number
- GB1599627A GB1599627A GB22730/78A GB2273078A GB1599627A GB 1599627 A GB1599627 A GB 1599627A GB 22730/78 A GB22730/78 A GB 22730/78A GB 2273078 A GB2273078 A GB 2273078A GB 1599627 A GB1599627 A GB 1599627A
- Authority
- GB
- United Kingdom
- Prior art keywords
- optionally substituted
- cycloalkyl
- dye
- substituted alkyl
- aryl
- 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
Links
- 239000000975 dye Substances 0.000 title claims abstract description 14
- -1 N,N-disubstituted 4-nitrosoaniline Chemical class 0.000 claims abstract description 39
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 15
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 14
- 125000003118 aryl group Chemical group 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
- GGOZGYRTNQBSSA-UHFFFAOYSA-N pyridine-2,3-diol Chemical compound OC1=CC=CN=C1O GGOZGYRTNQBSSA-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000003277 amino group Chemical group 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 238000006482 condensation reaction Methods 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- APVQNDRXQVWGKX-UHFFFAOYSA-N 2-nitrosoaniline Chemical compound NC1=CC=CC=C1N=O APVQNDRXQVWGKX-UHFFFAOYSA-N 0.000 claims description 2
- RTTKVNNZRGYCTK-UHFFFAOYSA-N CC=1C=C(O)N(C)C(=O)C=1C#N Chemical compound CC=1C=C(O)N(C)C(=O)C=1C#N RTTKVNNZRGYCTK-UHFFFAOYSA-N 0.000 claims description 2
- 229910006069 SO3H Inorganic materials 0.000 claims description 2
- 125000004367 cycloalkylaryl group Chemical group 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 150000002431 hydrogen Chemical group 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000005322 morpholin-1-yl group Chemical group 0.000 description 1
- KOOMFXGDLMRWSN-UHFFFAOYSA-N n-phenylnitrous amide Chemical class O=NNC1=CC=CC=C1 KOOMFXGDLMRWSN-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
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
- C09B55/00—Azomethine dyes
- C09B55/009—Azomethine dyes, the C-atom of the group -C=N- being part of a ring (Image)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Cosmetics (AREA)
Abstract
Process for preparing pyridone dyes of the formula <IMAGE> where R1 is hydrogen, an optionally substituted alkyl, aralkyl, cycloalkyl, aryl or heterocyclic radical or an optionally substituted amino group, R2, R3 and R4 are each independently of the others hydrogen, halogen, alkoxy or optionally substituted alkyl or cycloalkyl, and R5 and R6 are each independently of the other hydrogen or an optionally substituted alkyl, aralkyl, cycloalkyl, aryl or heterocyclic radical, or R5 and R6, R3 and R5 or R4 and R6 are heterocyclic rings, Y is hydrogen, hydroxyl, -CN, -COOR7, CONR7R8, -COR7 or an optionally substituted alkyl, aralkyl, cycloalkyl, aryl or heterocyclic radical and Z is -CN, -COOR9, -CONR9R10 or -COR9, wherein R7, R8, R9 and R10 are each independently of the others hydrogen or an optionally substituted alkyl, aralkyl, cycloalkyl, aryl or heterocyclic radical, by condensation of a hydroxypyridone of the formula <IMAGE> where Y, Z and R1 are each as defined above, with an N,N-disubstituted 4-nitrosoaniline of the formula <IMAGE> where R2 to R6 are each as defined above.
Description
(54) BLEACHABLE DYES
(71) We, CIBA-GEIGY AG, a body corporate organised according to the laws of Switzerland, of Basle, Switzerland, 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:- This invention relates to novel dyestuffs, to their production and to their use in photographic materials, and is an improvement of or modification to the invention described and claimed in British patent application no. 8924/77.
In no. 8924/77 (Serial No. 1591642) there are described dyestuffs of the general formula IL
wherein R1 represents a hydrogen atom or an optionally substituted alkyl, aralkyl, cycloalkyl, aryl or heterocyclic radical or an optionally substituted amino group,
Y represents a hydrogen atom or a hydroxy, -CN, -COOR1, -CONR1R2 or --COR' group or an optionally substituted alkyl, aralkyl, cycloalkyl, aryl or heterocyclic radical, and
Z represents a -CN, -COOR3, -CONR3R4, -SO3lI, SO3 or ZOR3 group, where Rt, R2, R3 and R4 each independently represent a hydrogen atom or an optionally substituted alkyl, aralkyl, cycloalkyl, aryl or heterocyclic radical, R2 R3, R4 each independently represent a hydrogen atom, a halogen atom, an optionally substituted alkyl, sulphonamido acylamido, amino or cycloalkyl group or an alkoxy or hydroxy group and R5 and R6 each independently represent a hydrogen atom or an optionally substituted alkyl, aralkyl, cycloalkyl, aryl or heterocyclic radical or R5 and R6 together with the nitrogen atom to which they are attached form a 5- or 6-membered nitrogen containing heterocyclic ring, or R3 and R5 together form with nitrogen atom a 5- or 6membered nitrogen containing heterocyclic ring, or R4 and R6 together form with the nitrogen atom a 5- or 6-membered nitrogen containing heterocyclic ring or two such heterocyclic rings are formed.
Throughout the specification the terms "lower alkyl" and "lower alkoxy" are used to denote alkyl or alkoxy radicals respectively containing from 1 to 6 carbon atoms.
The optionally substituted alkyl radicals represented by Y, R1-R6 and Rt, R2, R3 and R4 are preferably lower alkyl groups or substituted lower alkyl radicals, and as specific examples of such radicals there may be mentioned methyl, ethyl, n-propyl, nbutyl, n-octyl, n-decyl and n-dodecyl, hydroxy lower alkyl such as A-hydroxyethyl, lower alkoxy alkyl such as ,B-(methoxy or ethoxy) ethyl and y-methoxypropyl, cyanomethyl, carbamoylmethyl, carboethoxymethyl and acetylmethyl, and in particular for R5 and R6 p-methyl- sulphonamidoethyl and sulpho-n-butyl.
As examples of aralkyl radicals represented by Y, Rt, R3, R4, R5, R6, Rt, R2,
R3 and R4 there may be mentioned benzyl and p-phenyl ethyl.
As an example of a cycloalkyl radical represented by Y, R1-R6 and Rt, R2, R3 and R4 there may be mentioned cyclohexyl.
The optionally substituted aryl radicals represented by Y, Rt, R5 and R6, Rt, R2, R3 and R4 are preferably phenyl or optionally substituted phenyl radicals, and as specific examples of such radicals there may be mentioned phenyl, tolyl, chlorophenyl, methoxyphenyl and ethoxyphenyl. The optionally substituted heterocyclic radicals represented by Y, Rt, R5R6, Rt, R2, R3 and
R4 are preferebaly 5- and 6- membered heterocyclic rings and as specific examples of such radicals there may be mentioned 2 pyridyl, 2-thiazoyl, 1- piperidinyl and 1morpholinyl, each of which may be substituted.
As examples of 5- and 6- membered containing heterocyclic rings formed by joining R5 and R6 and the nitrogen atom, or
R3 and R5 and the nitrogen atom, or R4 and
R6 and the nitrogen atom, there may be mentioned piperidine, morpholine, piperazine and pyrrolidine.
According to a further feature of BPA 8924/77 (Serial No. 1591642) there is provided a process for the manufacture of the dyestuffs of formula I which comprises condensing a hydroxypyridone of the formula II:
wherein Y, Z, and R, have the meanings hereinbefore stated and X is a hydrogen or halogen or a coupling-off group with a colour developer of formula III:-
where R2-R6 have the meanings hereinbefore stated, in the presence of an oxidising agent and base.
We have now discovered an alternative method of manufacture of the dyestuffs of
Formula I.
According to this present invention there is provided a process for the preparation of dyestuffs of formula I which comprises condensing a hydroxypyridone of formula II with a 4-nitroso N,N-disubstituted aniline of formula IV:
wherein R2-R6 have the meanings assigned to them above. Advantageously the reaction is carried out in a solvent, preferably acetone, ethanol, or acetic acid, with or without external heating. The dyestuffs are readily isolated by conventional means, e.g. water precipitation.
The nitrosoanilines of Formula IV are conveniently obtained from their corresponding anilines by the method described in "Organic Synthesis
Collected Volume I," page 241. The hydroxypyridones of Formula II are obtained by the methods outlined in BP 1,256,095, and as described in "Heterocyclic Compounds-Pyridine and its Derivatives-Part 3" edited by Klinsberg and published in 1962 by Interscience.
The procedure for the manufacture of the dyestuffs of formula I by the method of the present invention is of especial value for the synthesis of water-soluble or hydrophilic dyestuffs falling under formula I, when the isolation and/or purification of these dyestuffs by the method of BPA 8924/77 (Serial No. 1591642) is difficult.
Also, often the base or oxidising agent employed in the reaction of hydroxypyridones of Formula II with a colour developer of Formula III causes a poor or negligible yield of the dye.
Further, where, in Formulae I and II when R1 is hydrogen the present process is advantageous.
Also, by the process of the present invention a purer dyestuff may be obtained and this is particularly advantageous as the dyestuffs are of especial use in photographic material. Examples of the dyestuffs manufactured by the process of this invention are shown in Table I. The groupings Rt, R5, and R6 define the dyes given by the general Formula V:
TABLE I
Dye R1 R5 R6
A Et Me Me
B Et C2H4OH C2H40H C C2H4OH C2H4OH C2H4OH D H C2H4OH C2H40H E Me Me C4H8SO3Na
The invention is illustrated by the following example:
Example
Dye A: 3-Cyano l-ethyl 6-hydroxy 4methyl pyrid-2-one (17.8g) and 4-dimethyl aminonitrosobenzene (16.6g) were stirred together in acetic acid (100 ml) at ambient temperature for thirty minutes. The reaction mixture was diluted with water, and the precipitated dye wash with water until the washings were colourless. The dye was dried in vacuo to yield 20.0g of green solid m.p. 192--30C A max (Me OH) 585, 405 nm.
Similarly prepared were:
Dye B: m.p. 176--70C A max (Me OH) 591, 408 nm
Dye C: m.p. 184--50C;1 A max (Me OH) 588, 410 nm
Dye D: m.p. l8990aO A max (Me OH) 584, 415 nm
Dye E: 3-cyano 6-hydroxy 1,4-dimethyl pyrid-2-one (0.82 g) and N-methyl N-4' sulphobutyl 4-nitrosoaniline sodium salt (1.47g) were stirred together in acetic acid (5 ml) for four hours at ambient temperature. The dye was precipitated from ether, and washed with ether to give 2.20 g of a brown solid, decomp. > 140 C A max (Me OH) 588, 410 nm.
WHAT WE CLAIM IS:
1. A process for the preparation of a dyestuff of the general formula:
wherein R1 represents a hydrogen atom or
an optionally substituted alkyl, aralkyl,
cycloalkyl, aryl or heterocyclic radical or an optionally substituted amino group,
Y represents a hydrogen atom or a hydroxy, --CN, --COOR', --CONR'R2 or -COR1 group or an optionally substituted
alkyl, aralkyl, cycloalkyl, aryl or
heterocyclic radical,
Z represents a -CN, -COOR3, CONR3R4, -SO3H, SO3, -COR3 group
where R1, R2, R3 and R4 each independently
represent a hydrogen atom or an optionally
substituted alkyl, aralky, cycloalkyl, aryl or
heterocyclic radical, R2, R3 and R4 each
independently represent a hydrogen atom, a
halogen atom, an optionally substituted alkyl, sulphonamido, acylamido, amino or
cycloalkyl group or an alkoxy or
hydroxy group, and R5 and R6 each
independently represent a hydrogen atom
or an optionally substituted alkyl, aralkyl, cycloalkyl aryl or heterocyclic radical or R5 and R6 together with the nitrogen atom to which they are attached form a 5- or 6-membered nitrogen containing heterocyclic ring, or R3 and R5 together form with the nitrogen atom a 5- or 6-membered nitrogen containing heterocyclic ring, or R4 and R6 together form with the nitrogen atom a 5- or 6membered nitrogen containing heterocyclic ring or two such heterocyclic rings are formed, with process comprises condensing a hydroxypyridone of the general formula::
where Y, Z and R, have the meaning assigned to them above and X is a hydrogen or halogen or a coupling-off group with a 4nitroso, N,N-disubstituted aniline of the general formula:
wherein R2-R6 have the meanings assigned
to them above.
2. A process according to claim 1 wherein the condensation reaction is carried out in a solvent.
3. A process according to claim 2 wherein the solvent is acetone, ethanol or acetic acid.
4. A process according to claim 3 wherein external heat is applied during the condensation reaction.
5. A process according to claim 1 substantially as hereinbefore described with reference to the foregoing Example.
6. Dyestuffs of the general formula set forth in claim 1 when prepared by the process claimed in any one of claims 1 to 5.
**WARNING** end of DESC field may overlap start of CLMS **.
Claims (6)
1. A process for the preparation of a dyestuff of the general formula:
wherein R1 represents a hydrogen atom or
an optionally substituted alkyl, aralkyl,
cycloalkyl, aryl or heterocyclic radical or an optionally substituted amino group,
Y represents a hydrogen atom or a hydroxy, --CN, --COOR', --CONR'R2 or -COR1 group or an optionally substituted
alkyl, aralkyl, cycloalkyl, aryl or
heterocyclic radical,
Z represents a -CN, -COOR3, CONR3R4, -SO3H, SO3, -COR3 group
where R1, R2, R3 and R4 each independently
represent a hydrogen atom or an optionally
substituted alkyl, aralky, cycloalkyl, aryl or
heterocyclic radical, R2, R3 and R4 each
independently represent a hydrogen atom, a
halogen atom, an optionally substituted alkyl, sulphonamido, acylamido, amino or
cycloalkyl group or an alkoxy or
hydroxy group, and R5 and R6 each
independently represent a hydrogen atom
or an optionally substituted alkyl, aralkyl, cycloalkyl aryl or heterocyclic radical or R5 and R6 together with the nitrogen atom to which they are attached form a 5- or 6-membered nitrogen containing heterocyclic ring, or R3 and R5 together form with the nitrogen atom a 5- or 6-membered nitrogen containing heterocyclic ring, or R4 and R6 together form with the nitrogen atom a 5- or 6membered nitrogen containing heterocyclic ring or two such heterocyclic rings are formed, with process comprises condensing a hydroxypyridone of the general formula: :
where Y, Z and R, have the meaning assigned to them above and X is a hydrogen or halogen or a coupling-off group with a 4nitroso, N,N-disubstituted aniline of the general formula:
wherein R2-R6 have the meanings assigned
to them above.
2. A process according to claim 1 wherein the condensation reaction is carried out in a solvent.
3. A process according to claim 2 wherein the solvent is acetone, ethanol or acetic acid.
4. A process according to claim 3 wherein external heat is applied during the condensation reaction.
5. A process according to claim 1 substantially as hereinbefore described with reference to the foregoing Example.
6. Dyestuffs of the general formula set forth in claim 1 when prepared by the process claimed in any one of claims 1 to 5.
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB22730/78A GB1599627A (en) | 1978-05-25 | 1978-05-25 | Bleachable dyes |
| JP14121878A JPS54153830A (en) | 1978-05-25 | 1978-11-17 | Preparing pyridone dyes |
| FR7832831A FR2426717A2 (en) | 1978-05-25 | 1978-11-21 | PYRIDONE COLORANTS, THEIR PREPARATION PROCESS AND THEIR USE |
| BE191873A BE872201R (en) | 1978-05-25 | 1978-11-22 | PYRIDONE COLORANTS, THEIR MANUFACTURING PROCESS AND THEIR USE |
| IT52174/78A IT1158155B (en) | 1978-05-25 | 1978-12-04 | PROCEDURE FOR PREPARING DYES FROM THE PYRIDON SERIES |
| CH1251778A CH640875A5 (en) | 1978-05-25 | 1978-12-07 | Process for preparing pyridone dyes |
| DE19782853354 DE2853354A1 (en) | 1978-05-25 | 1978-12-11 | PROCESS FOR THE MANUFACTURING OF PYRIDON DYES |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB22730/78A GB1599627A (en) | 1978-05-25 | 1978-05-25 | Bleachable dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1599627A true GB1599627A (en) | 1981-10-07 |
Family
ID=10184189
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB22730/78A Expired GB1599627A (en) | 1978-05-25 | 1978-05-25 | Bleachable dyes |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS54153830A (en) |
| BE (1) | BE872201R (en) |
| CH (1) | CH640875A5 (en) |
| DE (1) | DE2853354A1 (en) |
| FR (1) | FR2426717A2 (en) |
| GB (1) | GB1599627A (en) |
| IT (1) | IT1158155B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3929698A1 (en) * | 1989-09-07 | 1991-03-14 | Basf Ag | TRIAZOLOPYRIDINE DYES AND A METHOD FOR THERMAL TRANSFER OF METHINE DYES |
| US5162290A (en) * | 1990-04-27 | 1992-11-10 | Dai Nippon Insatsu Kabushiki Kaisha | Heat transfer sheet |
| US5580980A (en) * | 1991-05-03 | 1996-12-03 | Basf Aktiengesellschaft | N-aminopyridone dyes |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1292454A (en) * | 1969-09-23 | 1972-10-11 | Ici Ltd | Dyestuffs |
| US3867094A (en) * | 1970-12-30 | 1975-02-18 | Oreal | Dyeing keratinous fibers with dye compositions containing indoanilines |
| LU68988A1 (en) * | 1973-12-12 | 1975-08-20 |
-
1978
- 1978-05-25 GB GB22730/78A patent/GB1599627A/en not_active Expired
- 1978-11-17 JP JP14121878A patent/JPS54153830A/en active Pending
- 1978-11-21 FR FR7832831A patent/FR2426717A2/en active Granted
- 1978-11-22 BE BE191873A patent/BE872201R/en active
- 1978-12-04 IT IT52174/78A patent/IT1158155B/en active
- 1978-12-07 CH CH1251778A patent/CH640875A5/en not_active IP Right Cessation
- 1978-12-11 DE DE19782853354 patent/DE2853354A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| IT7852174A0 (en) | 1978-12-04 |
| JPS54153830A (en) | 1979-12-04 |
| BE872201R (en) | 1979-05-22 |
| FR2426717B2 (en) | 1982-04-02 |
| FR2426717A2 (en) | 1979-12-21 |
| IT1158155B (en) | 1987-02-18 |
| CH640875A5 (en) | 1984-01-31 |
| DE2853354A1 (en) | 1979-11-29 |
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| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |