Compositions: coating or plastic – Coating or plastic compositions – Marking
Reexamination Certificate
2000-05-12
2002-04-09
Klemanski, Helene (Department: 1755)
Compositions: coating or plastic
Coating or plastic compositions
Marking
C106S031780, C106S410000, C548S110000, C548S405000, C546S013000
Reexamination Certificate
active
06368395
ABSTRACT:
TECHNICAL FIELD
The present invention relates to new methods for making subphthalocyanine compounds. The present invention also relates to a family of new subphthalocyanine compounds. The new subphthalocyanine compounds may be used as a colorant, alone or in combination with one or more colorants. The present invention further relates to inks containing the new subphthalocyanine compounds.
BACKGROUND OF THE INVENTION
A variety of subphthalocyanine compounds and methods for making the same are known in the art. Most conventional methods for producing subphthalocyanine compounds typically require a high reaction temperature, usually in the range of about 200° C. to about 250° C., due to the use of solvents, such as 1-chloro-naphthalene. Further, most conventional methods produce subphthalocyanine compounds along with a variety of secondary products, which require extensive separation procedures in order to isolate the subphthalocyanine compound. In addition, the reaction yield for the production of subphthalocyanine compounds by most conventional methods is at most about 35%, and usually less than about 20%. Such reaction conditions result in high energy costs, potential damage to the environment due to environmentally-unfriendly solvents, and low yields, which in turn results in high costs for the subphthalocyanine compounds produced.
U.S. Pat. No. 5,864,044 issued to Van Lier et al. discloses methods of making subphthalocyanine compounds, wherein a solvent having a lower boiling point is used. Van Lier discloses the use of 1-chlorobenzene (b.p. 130° C.) as a suitable solvent for the production of subphthalocyanine compounds. However, 1-chlorobenzene is an environmentally unfriendly solvent currently under increased scrutiny by the U.S. Environmental Protection Agency. Although Van Lier discloses the production of subphthalocyanine compounds at yields of about 60%, the method uses an environmentally unfriendly solvent, which presents manufacturing problems in the U.S.
Although the prior art discloses methods of making subphthalocyanine compounds at yields of up to about 60%, higher yields are desired in order to cost-effectively produce subphthalocyanine compounds. Further, higher yields without the use of environmentally unfriendly solvents are more desirable.
Moreover, known subphthalocyanine compounds possess poor lightfastness properties, which prevent the compounds from being used as colorants in conventional ink sets. It is believed that the poor lightfastness of known subphthalocyanine compounds is primarily due to the high reactivity of the molecule in the excited state, as well as, the higher concentration of molecules in the excited state and the length of time in the excited state, when a sample of the molecule is exposed to light. As reported in “Synthesis and Nonlinear Optical, Photophysical, and Electrochemical Properties of Subphthalocyanines”, del Rey et al.,
J. Am. Chem. Soc.
, Vol. 120, No. 49 (1998), known subphthalocyanine compounds have an excited state lifetime of as much as 100 &mgr;sec. Other possible reasons for poor lightfastness and tendency to fade are (1) reaction with singlet oxygen, and (2) nucleophilic attack resulting in a loss of boron and/or substitution of a chromophore.
What is needed in the art is an improved method of making subphthalocyanine compounds, which uses an environmentally-friendly solvent, and at the same time, results in yields of greater than 50%. Further, what is also needed in the art is a new family of stable, subphthalocyanine compounds having improved lightfastness properties, which may be used as colorants, alone or in combination with one or more colorants.
SUMMARY OF THE INVENTION
The present invention addresses the needs described above by providing new methods of making subphthalocyanine compounds. The methods of the present invention may be used to produce known subphthalocyanine compounds, as well as, new families of subphthalocyanine compounds having superior light fastness properties disclosed herein.
The present invention is further directed to a new family of subphthalocyanine compounds having the following general formula:
wherein X
1
to X
12
each independently represent carbon or nitrogen; R
1
to R
12
and Z each independently represent —H, a halogen, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, an alkoxide group, a phenoxy group, a substituted phenoxy group, an alkyl sulfide, an aryl sulfide, a nitrogen-containing group, a sulfonic acid, a sulfur-containing group or an ester group; and wherein when any one of X
1
to X
12
is nitrogen, the corresponding R
1
to R
12
represents the pair of electrons on the nitrogen atom. The subphthalocyanine compounds may be used as a colorant alone or in combination with one or more colorants.
The present invention also relates to colorant compositions having improved stability, wherein the colorant comprises one or more of the above-described subphthalocyanine compounds.
These and other features and advantages of the present invention will become apparent after a review of the following detailed description of the disclosed embodiments and the appended claims.
DETAILED DESCRIPTION OF THE INVENTION
The present invention is directed to methods of making subphthalocyanine compounds. The methods of the present invention may be used to produce known subphthalocyanine compounds, as well as, a new family of subphthalocyanine compounds disclosed herein. Unlike conventional methods of making subphthalocyanine compounds, the methods of the present invention utilize a reaction mechanism, which occurs at a temperature below about 180° C., while employing environmentally friendly solvents. In addition, the methods of the present invention produce subphthalocyanine compounds at a reaction yield of greater than about 50%, and up to about 94%.
One method of making subphthalocyanine compounds of the present invention may be given by the following reaction scheme:
wherein X
1
to X
12
each independently represent carbon or nitrogen; R
1
to R
12
and Z each independently represent —H, a halogen, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, an alkoxide group, a phenoxy group, a substituted phenoxy group, an alkyl sulfide, an aryl sulfide, a nitrogen-containing group, a sulfonic acid, a sulfur-containing group, or an ester group; and wherein when any one of X
1
to X
12
is nitrogen, the corresponding R
1
to R
12
represents the pair of electrons on the nitrogen atom. The reaction may occur at a reaction temperature much lower than most conventional reaction methods. In one embodiment of the present invention, the method of making subphthalocyanine compounds takes place at a desired reaction temperature of from about 20° C. to about 180° C. More desirably, the reaction temperature is from about 50° C. to about 160° C. Even more desirably, the reaction temperature is from about 80° C. to about 150° C.
In a further embodiment of the present invention, the method of making subphthalocyanine compounds may be given by the following reaction scheme:
wherein R
1
to R
4
, R
7
to R
12
and Z each independently represent —H, a halogen, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, an alkoxide group, a phenoxy group, a substituted phenoxy group, an alkyl sulfide, an aryl sulfide, a nitrogen-containing group, a sulfonic acid, a sulfur-containing group, or an ester group. The reaction may occur at a reaction temperature as discussed above, with the desired reaction temperature being from about 80° C. to about 150° C. The resulting subphthalocyanine compounds have a unique, unsymmetrical chemical structure, which enables “intramacrocyclic quenching,” as well as, “intermacrocyclic quenching” with other molecules as described below.
The methods of the present invention use a variety of environmentally-friendly solvents. Desirably, the solvent comprises a “hydrogen-donating” solvent. As used herein, the term “hydrogen-donating” describes solvents, which are capable of donating a hyd
MacDonald John G.
Nohr Ronald Sinclair
Kilpatrick & Stockton LLP
Kimberly--Clark Worldwide, Inc.
Klemanski Helene
LandOfFree
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