1. A compound of the formula
in which
R1 represents hydrogen, substituted or unsubstituted C1-C8alkyl, substituted or unsubstituted C1-C8alkoxy or SO3H,
R2 represents SO3H or CO2H,
R3 and R3a each, independently of the other, represent hydrogen, a C1-C4alkyl group, which may be substituted or unsubstituted, halogen, hydroxy, substituted or unsubstituted C1-C4alkoxy, carboxy, NH2 or NHC1-C4alkyl and each of the residues
A1 and A2, independently of the other, is derived from a coupling component selected from the group consisting of
an acetoacetylated amine of the formula
in which
X1 represents C1-C4alkyl, or phenyl which is unsubstituted or monosubstituted by C1-C4alkyl, C1-C4alkoxy or halogen and
X2 represents phenyl which is unsubstituted, mono-, di- or trisubstituted by one or two SO3H, SO2NHC1-C4alkyl groups which alkyl groups may be substituted, SO2C1-C4alkyl, C1-C4substituted or unsubstituted alkyl, hydroxy, C1-C4alkoxy, halogen, CF3, NH2, NHCOC1-C4alkyl, NHCOOC1-C4alkyl, NHCONHC1-C4alkyl, CO2H, CONHC1-C4alkyl or NO2; a 1- or 2-naphthyl residue which is unsubstituted or substituted by one or two SO3H, SO2NHC1-C4alkyl, carboxy, CONHC1-C4alkyl, carboxyC1-C4alkyl or carboxyaryl groups or a 5- or 6-membered heterocyclic ring containing 1-3 heteroatoms and which may be benzannelated and be further substituted by C1-C4alkyl, C1-C4alkoxy or halogen and which may be attached to the NH-atom in formula (2) either via the hetero- or benzo-nucleus, in the case of benzannelated heterocycles;
a derivative of barbituric acid of the formula
in which
Y represents O, NCN or NCONH2;
a 2,4,6-triaminopyrimidine derivative;
a pyridone derivative of the formula
in which
Q1 represents hydrogen, hydroxy, C1-C2alkyl, hydroxyethyl, 2-(C1-C2alkoxy)alkyl, C1-C2alkoxy, COOH, CONH2 or COO C1-C2alkyl,
Q2 represents hydrogen, CN, halogen, SO3H or C1-C2alkyl which is unsubstituted or substituted by hydroxy, phenyl or SO3H,
Q3 represents hydrogen, phenyl, C1-C2alkylphenyl, cyclohexyl or C1-C4alkyl which is unsubstituted or substituted by hydroxy, CN, C1-C2alkoxy or SO3H and
Q4 represents hydrogen or hydroxy;
an aminopyrazole or a pyrazolone derivative of formula
in which
R4 represents hydrogen, substituted or unsubstituted C1-C4alkyl, C2-C4alkenyl, NHCO C1-C4alkyl or CO2H, each
R5 and R6, independently of the other, represent hydrogen, halogen, C1-C4alkyl, SO3H or CO2H and
R7 represents hydrogen or C1-C4alkyl;
a benzoic acid derivative of formula
in which
R7 represents hydrogen or C1-C4alkyl and
R8 represents hydrogen or hydroxy or
A1 and A2, each one independently of the other, represent a phenol residue of the formula
in which
R9 and R10, each one independently of the other, represent hydrogen, C1-C4alkyl, C1-C4alkoxy, hydroxy, halogen, NH2, NHCO C1-C4alkyl, NO2, SO3H, CO2C1-C4alkyl or CONHC1-C4alkyl groups,
with the proviso that in compounds of formula
if
R1, R2, R3 and R3a each, independently of the others, are hydrogen or SO3H, then
A1 and A2 are not both a 1-phenyl or 1-sulphophenyl-3-methyl-5-aminopyrazole residue, or, if
R1, R2, R3 and R3a represent hydrogen and
A1 is a residue of formula (9) in which
R7 represents hydrogen or methyl, then
A2does not represent a 1-phenyl or 1-sulphophenyl-3-methyl- or 3-carboxy pyrazol-5-one residue
or, if
R1, R3 and R3a are hydrogen and R2 is SO3H and one of
A1 and A2 represents a 1-sulphophenyl-3-methylpyrazol-5-one residue, then the other is not a residue of formula (11) in which both
R9 and R10 are hydrogen.
2. A compound of formula (1), according to claim 1, which contains a total number of two, three or four SO3H andor CO2H groups.
3. A compound of the formula
according to claims 1 or 2, in which
R1 represents hydrogen, C1-C4alkyl, C1-C4alkoxy or SO3H,
R2 represents SO3H or CO2H,
R3 represents hydrogen, a C1-C4alkyl group, halogen, hydroxy, C1-C4alkoxy, carboxy, NH2 or NHC1-C4alkyl,
R3a represents hydrogen or NH2 and
A1 and A2 are as defined in claim 1.
4. A compound of formula (13), according to claim 3, in which
R3 and R3a both represent hydrogen and
A1 and A2, each one independently of the other, is derived from a coupling component selected from the group consisting of
an acetoacetylated amine of the formula
in which
X1 represents C1-C4alkyl, and
X2 represents phenyl, which is unsubstituted, mono-, di- or trisubstituted by SO3H, C1-C4alkyl, hydroxy, C1-C4alkoxy, halogen or CO2H;
barbituric acid or cyanoiminobarbituric acid;
2,4,6-triaminopyrimidine;
citrazinic acid;
an aminopyrazole or a pyrazolone derivative of formula
in which
R4 represents C1-C4alkyl or CO2H,
R5 represents hydrogen, halogen, C1-C4alkyl, SO3H or CO2H and
R6 represents hydrogen;
a benzoic acid derivative of formula
in which
R7 represents hydrogen or C1-C4alkyl and
R8 represents hydrogen or hydroxy or
A1 and A2, each one independently of the other, represent a phenol residue of the formula
in which
R9 represents hydrogen, C1-C4alkyl, C1-C4alkoxy, hydroxy, halogen or SO3H and
R10 represents hydrogen.
5. A compound of formula
according to claims 1 or 2, in which
R1 represents hydrogen, C1-C4alkyl, C1-C4alkoxy or SO3H,
R2 represents SO3H or CO2H,
R3 represents hydrogen, a C1-C4alkyl group, halogen, hydroxy, C1-C4alkoxy, carboxy, NH2 or NHC1-C4alkyl,
R3a represents hydrogen or NH2 and
A1 and A2 are as defined in claim 1.
6. A compound of formula (14), according to claim 5, in which
R3 and R3a both represent hydrogen and
A1 and A2, each one independently of the other, is derived from a coupling component selected from the group consisting of
an acetoacetylated amine of the formula
in which
X1 represents C1-C4alkyl, and
X2 represents phenyl, which is unsubstituted, mono-, di- or trisubstituted by SO3H, C1-C4alkyl, hydroxy, C1-C4alkoxy, halogen or CO2H;
barbituric acid or cyanoiminobarbituric acid;
2,4,6-triaminopyrimidine;
citrazinic acid;
an aminopyrazole or a pyrazolone derivative of formula
in which
R4 represents C1-C4alkyl or CO2H,
R5 represents hydrogen, halogen, C1-C4alkyl, SO3H or CO2H and
R6 represents hydrogen;
a benzoic acid derivative of formula
in which
R7 represents hydrogen or C1-C4alkyl and
R8 represents hydrogen or hydroxy or
A1 and A2, each one independently of the other, represent a phenol residue of the formula
in which
R9 represents hydrogen, C1-C4alkyl, C1-C4alkoxy, hydroxy, halogen or SO3H and
R10 represents hydrogen.
7. A compound of formula
according to claims 1 or 2, in which
R1 represents hydrogen, C1-C4alkyl, C1-C4alkoxy or SO3H,
R2 represents SO3H or CO2H,
R3 represents hydrogen, a C1-C4alkyl group, halogen, hydroxy, C1-C4alkoxy, carboxy, NH2 or NHC1-C4alkyl,
R3a represents hydrogen or NH2 and
A1 and A2 are as defined in claim 1.
8. A compound of formula (15), according to claim 7, in which
R3 and R3a both represent hydrogen and
A1 and A2, each one independently of the other, is derived from a coupling component selected from the group consisting of
an acetoacetylated amine of the formula
in which
X1 represents C1-C4alkyl, and
X2 represents phenyl, which is unsubstituted, mono-, di- or trisubstituted by SO3H, C1-C4alkyl, hydroxy, C1-C4alkoxy, halogen or CO2H;
barbituric acid or cyanoiminobarbituric acid;
2,4,6-triaminopyrimidine;
citrazinic acid;
an aminopyrazole or a pyrazolone derivative of formula
in which
R4 represents C1-C4alkyl or CO2H,
R5 represents hydrogen, halogen, C1-C4alkyl, SO3H or CO2H and
R6 represents hydrogen;
a benzoic acid derivative of formula
in which
R7 represents hydrogen or C1-C4alkyl and
R8 represents hydrogen or hydroxy or
A1 and A2, each one independently of the other, represent a phenol residue of the formula
in which
R9 represents hydrogen, C1-C4alkyl, C1-C4alkoxy, hydroxy, halogen or SO3H and
R10 represents hydrogen.
9. A compound of formula
according to claims 1 or 2, in which
R1, represents hydrogen, C1-C4alkyl, C1-C4alkoxy or SO3H,
R2 represents SO3H or CO2H,
R3 represents hydrogen, a C1-C4alkyl group, halogen, hydroxy, C1-C4alkoxy, carboxy, NH2 or NHC1-C4alkyl,
R3a represents hydrogen or NH2 and
A1 and A2 are as defined in claim 1.
10. A compound of formula (16), according to claim 9, in which
R3 and R3a both represent hydrogen and
A1 and A2, each one independently of the other, is derived from a coupling component selected from the group consisting of
an acetoacetylated amine of the formula
in which
X1 represents C1-C4alkyl, and
X2 represents phenyl, which is unsubstituted, mono-, di- or trisubstituted by SO3H, C1-C4alkyl, hydroxy, C1-C4alkoxy, halogen or CO2H;
barbituric acid or cyanoiminobarbituric acid;
2,4,6-triaminopyrimidine;
citrazinic acid;
an aminopyrazole or a pyrazolone derivative of formula
in which
R4 represents C1-C4alkyl or CO2H,
R5 represents hydrogen, halogen, C1-C4alkyl, SO3H or CO2H and
R6 represents hydrogen;
a benzoic acid derivative of formula
in which
R7 represents hydrogen or C1-C4alkyl and
R8 represents hydrogen or hydroxy or
A1 and A2, each one independently of the other, represent a phenol residue of the formula
in which
R9 represents hydrogen, C1-C4alkyl, C1-C4alkoxy, hydroxy, halogen or SO3H and
R10 represents hydrogen.
11. A process for the preparation of a compound of formula (1), according to claim 1, by tetrazotisation of a diaminobenzanilide derivative of the formula
in which R1, R2, R3 and R3a are as defined in claim 1, and sequential coupling with a coupling component of the formula A1H or A2H, followed by coupling with a coupling component of the formula A2H or ASH, A2 and A1 being as defined in claim 1.
12. A compound of the formula
13. A process for the preparation of compound (18), according to claim 12, by reaction of 2-methoxy-4-nitroaniline-5-sulphonic acid with the appropriate nitrobenzoyl halide, followed by reduction of the resulting dintrobenzanilide.
14. Use of the compound of formula (18), according to claim 12, for the preparation of the appropriate compound of formula (1), according to claim 1.
15. Use of the compound of formula (1), according to claim 1, for dyeing natural or synthetic materials.
16. A solid dye preparation for dyeing paper, comprising a compound of the formula (1) according to claim 1, and, optionally, further auxiliaries.
17. Aqueous solutions for dyeing paper, comprising a compound of the formula (1), according to claim 1, and, optionally, further auxiliaries.
18. Aqueous solutions according to claim 17 containing, as further auxiliaries, solubilizers andor organic solvents.
19. Paper which is dyed with a compound of the formula (1), according to claim 1, in the form of a solid dye preparation, according to claim 16, or an aqueous solution, according to claim 17.
The claims below are in addition to those above.
All refrences to claim(s) which appear below refer to the numbering after this setence.
1. A clutch mechanism comprising:
a housing adapted to be rotated by an associated engine;
a shaft having first and second sections and a first end that extends from the housing, the first end adapted to be the only transmission input drive shaft for an associated transmission;
a first clutch device positioned within the housing, the first clutch device being selectively rotatably connectable to the first section of the shaft, the first clutch device including a planetary gear set; and,
a second clutch device positioned within the housing, the second clutch device being selectively rotatably connectable to the second section of the shaft.
2. The clutch mechanism of claim 1 wherein the first and second clutch devices comprise first and second wet clutches respectively.
3. The clutch mechanism of claim 1 wherein the planetary gear set comprises:
a planetary carrier that is rotatably connected to the first section of the shaft;
a ring gear that is selectively rotatably connected to at least a first clutch plate of the first clutch device;
a sun gear; and,
a plurality of planetary gears that are rotatably connected to the ring gear, the sun gear, and the planetary carrier.
4. The clutch mechanism of claim 1 wherein the first and second clutch devices provides gear splitting means for use in doubling the number of gear ratios supplied by the associated transmission.
5. The clutch mechanism of claim 1 wherein the housing comprises a flange adapted to be connected to a flywheel for rotation thereby.
6. The clutch mechanism of claim 1 wherein the first clutch device, when engaged, connects the housing to the first section of the shaft.
7. The clutch mechanism of claim 1 wherein the second clutch device, when engaged, connects the housing to the second section of the shaft.
8. A clutch mechanism comprising:
a housing adapted to be rotated by an associated engine, wherein the housing comprises a wall defining first and second housing zones;
a shaft having first and second sections and a first end that extends from the housing, the first end adapted to be an input to an associated transmission;
a first clutch device positioned within the housing, the first clutch device being selectively rotatably connectable to the first section of the shaft, the first clutch device including a planetary gear set, the first clutch device and the first section of the shaft being positioned substantially within the first housing zone;
a second clutch device positioned within the housing, the second clutch device being selectively rotatably connectable to the second section of the shaft, the second clutch device and the second section of the shaft being positioned substantially within the second housing zone; and,
wherein the first and second clutch devices comprise first and second wet clutches respectively.
9. The clutch mechanism of claim 8 wherein the clutch wall is substantially perpendicular to the axis of the shaft.
10. The clutch mechanism of claim 8 wherein the housing comprises a flange adapted to be connected to a flywheel for rotation thereby.
11. The clutch mechanism of claim 8 wherein the wall has an opening that receives the shaft.
12. The clutch mechanism of claim 8 wherein the first clutch device, when engaged, connects the housing to the first section of the shaft.
13. The clutch mechanism of claim 8 wherein the second clutch device, when engaged, connects the housing to the second section of the shaft.
14. A clutch mechanism comprising:
a housing adapted to be rotated by an associated engine;
a shaft having first and second sections and a first end that extends from the housing, the first end adapted to be an input to an associated transmission;
a first clutch device positioned within the housing, the first clutch device being selectively rotatably connectable to the first section of the shaft, the first clutch device including a planetary gear set comprising: (a) a planetary carrier that is rotatably connected to the first section of the shaft; (b) a ring gear that is selectively rotatably connected to at least a first clutch plate of the first clutch device; (c) a sun gear that does not rotate with respect to a housing of the associated transmission; and, a plurality of planetary gears that are rotatably connected to the ring gear, the sun gear, and the planetary carrier; and,
a second clutch device positioned within the housing, the second clutch device being selectively rotatably connectable to the second section of the shaft.
15. The clutch mechanism of claim 14 where the planetary carrier is splined to the first section of the shaft and the sun gear is adapted to be splined to the housing of the associated transmission.
16. The clutch mechanism of claim 14 wherein the housing comprises a flange adapted to be connected to a flywheel for rotation thereby.
17. The clutch mechanism of claim 14 wherein the first clutch device, when engaged, connects the housing to the first section of the shaft.
18. The clutch mechanism of claim 14 wherein the second clutch device, when engaged, connects the housing to the second section of the shaft.
19. A clutch mechanism comprising:
a housing adapted to be rotated by an associated engine;
a shaft having first and second sections and a first end that extends from the housing, the first end adapted to be an input to an associated transmission;
a first clutch device positioned within the housing, the first clutch device being selectively rotatably connectable to the first section of the shaft, the first clutch device including a planetary gear set that comprises a planetary carrier that is splined to the first section of the shaft; and,
a second clutch device positioned within the housing, the second clutch device being selectively rotatably connectable to the second section of the shaft, wherein the second clutch device comprises a hub that is splined to the second section of the shaft.
20. The clutch mechanism of claim 19 wherein the housing comprises a flange adapted to be connected to a flywheel for rotation thereby.
21. The clutch mechanism of claim 19 wherein the first clutch device, when engaged, connects the housing to the first section of the shaft.
22. The clutch mechanism of claim 19 wherein the second clutch device, when engaged, connects the housing to the second section of the shaft.
23. A clutch mechanism comprising:
a housing adapted to be rotated by an associated engine;
a shaft having a first end that extends from the housing, the first end adapted to be the only transmission input drive shaft for an associated transmission; and,
gear splitting means for use in doubling the number of gear ratios supplied by the associated transmission.
24. The clutch mechanism of claim 23 wherein the gear splitting means comprises:
a first clutch device positioned within the housing, the first clutch device selectively rotatably connectable to the first section of the shaft, the first clutch device comprising a first wet clutch and including a planetary gear set; and,
a second clutch device positioned within the housing, the second clutch device selectively rotatably connectable to the second section of the shaft, the second clutch device comprising a second wet clutch.
25. The clutch mechanism of claim 24 wherein the first clutch device, when engaged, connects the housing to the first section of the shaft.
26. The clutch mechanism of claim 24 wherein the second clutch device, when engaged, connects the housing to the second section of the shaft.
27. The clutch mechanism of claim 23 wherein the housing comprises a flange adapted to be connected to a flywheel for rotation thereby.
28. A clutch mechanism comprising:
a housing adapted to be rotated by an associated engine, wherein the housing comprises a clutch wall defining first and second housing zones;
a shaft having a first end that extends from the housing, the first end adapted to be an input to an associated transmission; and,
gear splitting means for use in doubling the number of gear ratios supplied by the associated transmission, wherein the gear splitting means comprises:
(a) a first clutch selectively rotatably connectable to the first section of the shaft, the first clutch device comprising a first wet clutch and including a planetary gear set, the first clutch device and the first section of the shaft being positioned substantially within the first housing zone; and,
(b) a second clutch device selectively rotatably connectable to the second section of the shaft, the second clutch device comprising a second wet clutch, the second clutch device and the second section of the shaft being positioned substantially within the second housing zone.
29. The clutch mechanism of claim 28 wherein the planetary gear set comprises:
a planetary carrier that is rotatably connected to the first section of the shaft;
a ring gear that is selectively rotatably connected to the first wet clutch;
a sun gear that does not rotate with respect to a housing of the associated transmission; and,
a plurality of planetary gears that are rotatably connected to the ring gear, the sun gear, and the planetary carrier.
30. The clutch mechanism of claim 29 wherein the planetary carrier is splined to the first section of the shaft and wherein the second clutch device comprises a hub that is splined to the second section of the shaft.
31. The clutch mechanism of claim 28 wherein the housing comprises a flange adapted to be connected to a flywheel for rotation thereby.
32. The clutch mechanism of claim 28 wherein the wall has an opening that receives the shaft.
33. The clutch mechanism of claim 28 wherein the first clutch device, when engaged, connects the housing to the first section of the shaft.
34. The clutch mechanism of claim 28 wherein the second clutch device, when engaged, connects the housing to the second section of the shaft.
35. A method of doubling the number of gear ratios supplied by a transmission, comprising the steps of:
providing an automobile engine;
providing an automatic automobile transmission that only receives one transmission input drive shaft;
providing a clutch mechanism comprising: a housing rotatably connected to the engine, a shaft having first and second sections and a first end that extends from the housing and defines the transmission input drive shaft, a first clutch device, including a planetary gear set, that is selectively rotatably connectable to the first section of the shaft, and a second clutch device that is selectively rotatably connectable to the second section of the shaft;
engaging the first clutch device and providing a first number of gear ratios;
disengaging the first clutch device; and,
engaging the second clutch device and providing a second number of gear ratios.
36. The method of claim 35 further comprising the steps of:
providing the first clutch device with a first clutch plate;
providing the planetary gear set with a planetary carrier, a ring gear, a sun gear, and a plurality of planetary gears that are rotatably connected to the ring gear, the sun gear, and the planetary carrier;
wherein the step of engaging the first clutch device and providing a first number of gear ratios, comprises the steps:
engaging the first clutch plate;
rotatably connecting the first clutch to the ring gear; and,
rotatably connecting the planetary carrier to the first section of the shaft.
37. The method of claim 35 wherein the step of, engaging the first clutch device and providing a first number of gear ratios, comprises the step of:
connecting the housing to the first section of the shaft.
38. The method of claim 35 wherein the step of, engaging the second clutch device and providing a second number of gear ratios, comprises the step of:
connecting the housing to the second section of the shaft.
39. A method of doubling the number of gear ratios supplied by a transmission, comprising the steps of:
providing an automobile engine and an automatic automobile transmission;
providing a clutch mechanism comprising:
(a) a housing rotatably connected to the engine;
(b) a shaft having first and second sections and a first end that extends from the housing and defines an input to the transmission;
(c) a first clutch device having a first clutch plate and a planetary gear set that is selectively rotatably connectable to the first section of the shaft, the planetary gear set comprising: a planetary carrier, a ring gear, a sun gear, and a plurality of planetary gears that are rotatably connected to the ring gear, the sun gear, and the planetary carrier; and,
(d) a second clutch device that is selectively rotatably connectable to the second section of the shaft;
engaging the first clutch device and providing a first number of gear ratios, this step comprising the steps of:
(a) engaging the first clutch plate;
(b) rotatably connecting the first clutch to the ring gear; and,
(c) rotatably connecting the planetary carrier to the first section of the shaft; and,
(d) preventing the sun gear from rotating with respect to a housing of the transmission; and,
disengaging the first clutch device; and,
engaging the second clutch device and providing a second number of gear ratios.
40. The method of claim 39 further comprising the steps of:
providing the second clutch device with a second clutch plate and a hub;
wherein the step of engaging the second clutch device and providing a second number of gear ratios comprises the steps of:
engaging the second clutch plate; and,
rotatably connecting the hub to the second section of the shaft.
41. A clutch mechanism comprising:
a housing adapted to be rotated by an associated engine, wherein the housing comprises a wall defining first and second housing zones;
a shaft having first and second sections and a first end that extends from the housing, the first end adapted to be an input to an associated transmission;
a first clutch device positioned within the housing, the first clutch device being selectively rotatably connectable to the first section of the shaft, the first clutch device including a planetary gear set, the first clutch device and the first section of the shaft being positioned substantially within the first housing zone; and,
a second clutch device positioned within the housing, the second clutch device being selectively rotatably connectable to the second section of the shaft, the second clutch device and the second section of the shaft being positioned substantially within the second housing zone.
42. The clutch mechanism of claim 41 wherein the housing comprises a flange adapted to be connected to a flywheel for rotation thereby.
43. The clutch mechanism of claim 41 wherein the wall has an opening that receives the shaft.
44. The clutch mechanism of claim 41 wherein the first clutch device, when engaged, connects the housing to the first section of the shaft.
45. The clutch mechanism of claim 41 wherein the second clutch device, when engaged, connects the housing to the second section of the shaft.