Pigment yellow 74 and printing ink composition

Details Pigment yellow 74 and printing ink composition Pigment yellow 74 and printing ink composition

2002-12-03

2004-02-17

Green, Anthony J. (Department: 1755)

Compositions: coating or plastic

Coating or plastic compositions

Marking

C106S496000, C534S885000

Reexamination Certificate

active

06692559

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to a pigment yellow 74 and a printing ink composition using it. More specifically, it relates to a pigment yellow 74 improved in color strength and transparency and a printing ink composition using it.
BACKGROUND OF THE INVENTION
Conventionally, as a yellow pigment for a printing ink, there has been used a disazo yellow pigment using 3,3′-dichlorobenzidine as a tetrazo component and an acetoacetoanilide compound as a coupling component. However, since the disazo yellow pigment has a biphenyl skeleton in its structure and contains chlorine, there is an apprehension of the generation of a toxic material at the time of disposing of a printed matter.
For this reason, it is strongly required to develop a yellow pigment which has pigment performance equivalent to that of the disazo yellow pigment and is producible at a low production cost and excellent in hygiene. Pigment yellow 74 using 2-methoxy-4-nitroaniline as a diazo component and 2-methoxyacetoacetoanilide as a coupling component has advantages of excellent light resistance and clearness but has disadvantages of extremely poor transparency and color strength.
For improving the transparency and color strength of the pigment yellow 74, a surface-treatment technique is conventionally adopted. This technique is a method in which a rosin alkali salt solution (so-called rosin soap) is added into a coupler component or into a pigment slurry after coupling and then a metal salt for a lake such as aluminium sulfate is added to deposit the rosin, as an insoluble rosin lake metal salt, on a pigment surface, whereby a pigment particle shape is finely controlled. However, this technique is not sufficient.
Under the present situation, for the above reason, the pigment yellow 74 is only partially used for a building material coating composition, etc., which is required to have hiding power, and its applications to a printing ink which is required to have higher transparency and color strength have been hardly developed.
SUMMARY OF THE INVENTION
It is an object of the present invention to provide a pigment yellow 74 which is improved in transparency and color strength without impairing its inherent light resistance and clearness.
According to the present invention, there is provided a pigment yellow 74 obtained by coupling a coupler component containing 2-methoxyacetoacetoanilide and an acetoacetoanilide derivative of the following formula (1) in an amount of 0.1 to 10 mol %, based on the 2-methoxyacetoacetoanilide, and a diazo component obtained by diazotizing 2-methoxy-4-nitroaniline,
wherein X may be the same or different and is CONR
1
R
2
, SO
2
NR
1
R
2
, NHCOR
1
, CONH(CH
2
)
K
NR
1
R
2
or SO
2
NH(CH
2
)
K
NR
1
R
2
(in which each of R
1
and R
2
is independently a hydrogen atom or an alkyl group, or R
1
and R
2
together form a cyclic structure, and k is an integer of 1 to 4), m is 1 or 2, Y may be the same or different and is R
3
, OR
3
(in which R
3
is a hydrogen atom or an alkyl group), COOH or SO
3
H, and n is an integer of 0 to 2.
According to the present invention, further, there is provided a pigment yellow 74 according to the above, wherein the diazo component is obtained by diazotizing the 2-methoxy-4-nitroaniline and an aniline derivative of the following formula (2) in an amount of 0.1 to 10 mol % based on the 2-methoxy-4-nitroaniline,
in which Z may be the same or different and is CONR
1
R
2
, SO
2
NR
1
R
2
, CONH(CH
2
)
K
NR
1
R
2
, SO
2
NH(CH
2
)
K
NR
1
R
2
, COOH or SO
3
H (in which each of R
1
and R
2
is independently a hydrogen atom or an alkyl group, or R
1
and R
2
together form a cyclic structure, and k is an integer of 1 to 4), s is an integer of 1 or 2, Q may be the same or different and is R
3
, OR
3
or NO
2
(in which R
3
is a hydrogen atom or an alkyl group), and t is an integer of 0 to 2.
According to the present invention, further, there is provided a pigment yellow 74 obtained by coupling a coupler component containing 2-methoxyacetoacetoanilide with a diazo component obtained by diazotizing 2-methoxy-4-nitroaniline and an aniline derivative of the formula (2) in an amount of 0.1 to 10 mol % based on the 2-methoxy-4-nitroaniline,
wherein Z may be the same or different and is CONR
1
R
2
, SO
2
NR
1
R
2
, CONH(CH
2
)
K
NR
1
R
2
, SO
2
NH(CH
2
)
K
NR
1
R
2
, COOH or SO
3
H (in which each of R
1
and R
2
is independently a hydrogen atom or an alkyl group, or R
1
and R
2
together form a cyclic structure, and k is an integer of 1 to 4), s is an integer of 1 or 2, Q may be the same or different and is R
3
, OR
3
or NO
2
(in which R
3
is a hydrogen atom or an alkyl group), and t is an integer of 0 to 2.
According to the present invention, further, there is provided a printing ink composition comprising the pigment yellow 74 recited the above and a vehicle for a printing ink.
DETAILED DESCRIPTION OF THE INVENTION
In the present invention, R
1
and R
2
in an acetoacetoanilide derivative of the formula (1) and an aniline derivative of the formula (2) are each a hydrogen atom or an alkyl group. As the alkyl group, preferred is an alkyl group having 1 to 18 carbon atoms, and an alkyl group having 1 to 4 carbon atoms is more preferred. Further, as a cyclic structure obtained by bonding of R
1
and R
2
, there is a five-membered ring or a six-membered ring. The above cyclic structure may further contain a nitrogen atom or an oxygen atom as a constituent component.
Examples of an amine residue represented by —NR
1
R
2
in the formula (1) and the formula (2) include a methylamino group, an ethylamino group, a stearylamino group, a dimethylamino group, a diethylamino group, a methylaminopropylamino group, a dimethylaminopropylamino group, a diethylaminopropylamino group and a N-aminoethyl-4-pipecolinyl group, while the amine residue shall not be limited to these examples.
Further, R
3
in the formula (1) is a hydrogen atom or an alkyl group. As the alkyl group, an alkyl group having 1 to 4 carbon atoms is preferred.
Further, examples of an aniline derivative having a carboxyl group or a sulfonic group include 4-methoxyaniline-2-sulfonic acid, 2,5-dimethoxyaniline-4-sulfonic acid, 2-nitroaniline-4-sulfonic acid and 2-chloro-4-sulfo-5-aminobenzoic acid.
The pigment yellow 74 of the present invention can be produced according to a conventionally-known method. That is, 2-methoxy-4-nitroaniline is diazotized to prepare a diazonium component, on the other hand, the acetoacetoaniline derivative of the formula (1) in an amount of 0.1 to 10 mol %, preferably 1 to 5 mol %, based on 2-methoxyacetoacetoanilide, is added to 2-methoxyacetoacetoanilide to prepare a coupling component, and the diazonium component and the coupling component are coupled according to a general method.
Further, when the aniline derivative of the formula (2) is used as a diazo component, the aniline derivative in an amount of 0.1 to 10 mol %, preferably 1 to 5 mol %, based on 2-methoxy-4-nitroaniline, is added to 2-methoxy-4-nitroaniline, then the resultant mixture is diazotized and coupling is similarly carried out. The coupling reaction is not specially limited, and it may be a batch method carried out under an acidic condition of acetic acid, which is usually called an acid dipping method, or a continuous method in which a diazo solution and a coupling solution are simultaneously added in equal reaction amounts.
The pigment yellow 74 of the present invention in the state of a wet cake is flushed with a vehicle for a printing ink to prepare a printing ink. Otherwise, a powdery pigment of the pigment yellow 74 is kneaded with a vehicle for a printing ink to prepare a printing ink. The pigment for the flushing can be obtained as a wet cake by filtrating and washing a slurry after coupling and compressing it such that a pigment content becomes 26 to 32% by weight. The powdery pigment can be obtained by drying the wet cake and pulverizing the dried wet cake.
When an offset printing ink is produced by using the pigment yellow 74 of the present invention, flushing is carried out with a fl

Affiliated with

Also associated with

Rating

Pigment yellow 74 and printing ink composition does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Pigment yellow 74 and printing ink composition, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Pigment yellow 74 and printing ink composition will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3309507