Compositions: coating or plastic – Coating or plastic compositions – Marking
Reexamination Certificate
2001-01-12
2003-02-25
Klemanski, Helene (Department: 1755)
Compositions: coating or plastic
Coating or plastic compositions
Marking
C106S031770
Reexamination Certificate
active
06524379
ABSTRACT:
TECHNICAL FIELD
The present invention relates to porphines, methods for making porphines, and the use of porphines in ink compositions.
BACKGROUND OF THE INVENTION
U.S. patent application Ser. No. 08/757,222 filed Nov. 27, 1996, now U.S. Pat. No. 5,782,963; U.S. patent application Ser. No. 08/788,863 filed Jan. 23, 1997, pending; U.S. patent application Ser. No. 08/843,410 filed Apr. 15, 1997, now U.S. Pat. No. 5,855,655; U.S. patent application Ser. No. 08/903,911 filed Jul. 31, 1997, now U.S. Pat. No. 5,891,229; U.S. Provisional Patent Applications Serial Nos. 60/055,785 filed Aug. 15, 1997, and 60/062,643 filed Oct. 22, 1997; U.S. patent application Ser. No. 09/133,574 filed Aug. 13, 1998, pending; and U.S. patent application Ser. No. 09/058,385 filed Apr. 9, 1998, pending; all of which are assigned to Kimberly Clark Worldwide, Inc., disclose the use of a variety of porphines as colorant stabilizers. Porphines disclosed in the above-referenced applications include, but are not limited to, porphines having the following general structure:
wherein R is any proton-donating moiety and M is iron, cobalt or copper. Desirably, R is SO
3
H,
COOH, or R
1
COOH wherein R
1
is an alkyl group of from 1 to 6 carbons. R may also be in its corresponding salt form, such as SO
3
Na for SO
3
H or
One such porphine is Cu-meso-tetra-(2-sulfanatophenyl)-porphine (designated o-CuTPPS4) having the following structure:
An attempt to make o-CuTPPS4 is disclosed in Treibs et al.,
Leibigs Ann. Chem.,
718, 183, 1998 (hereinafter, “Treibs”). Treibs tried to prepare o-TPPS4 from 2-formylbenzenesulfonic acid, pyrrole, and propionoic acid. However, Treibs could not isolate the resulting product. Treibs reported a yield by GLC analysis of less than about 10%.
Although porphines provide excellent light stability to colorants, some porphines are relatively unstable and/or tend to “yellow” colorant compositions containing magenta dyes. A more desirable porphine molecule would be one that has at least one of the following characteristics: (1) the porphine molecule has less tendency to “yellow” a colorant composition, (2) the porphine molecule has the ability to make the colorant composition more “blue”; and (3) the porphine molecule, when used as a colorant, has superior lightfastness properties.
Further, while some of the above-described porphines provide excellent stability to one or more colorants associated with the porphines, they do not provide an orange/red color to a composition containing the porphines.
Accordingly, there exists a need in the art for a convenient, low cost, high yield method of making porphines, and compositions containing the porphines. Further, there exists a need for improved porphines, which are capable of providing superior colorant stability while being more stable themselves and without the tendency to “yellow” colorant compositions containing magenta dyes. Finally, there exists a need in the art for a new family of compounds that may be used alone as a colorant or may be used as a colorant stabilizer for one or more colorants associated with the new compounds.
SUMMARY OF THE INVENTION
The present invention addresses the needs described above by providing a new family of porphine compounds having the following general formula:
where M is iron, cobalt or copper; R represents a halogenated alkyl group,
wherein R
1
to R
77
each independently represent —H; a halogen; an alkyl group; a substituted alkyl group; an aryl group; a substituted aryl group; an alkoxy group; a nitrogen-containing group; a sulfur-containing group; —OR′, —NR′R″, or —SR′, wherein R′ and R″ each independently represent an alkyl group, a substituted alkyl group, an aryl group, or a substituted aryl group.
The porphine compounds may be used as a magenta colorant and/or as a colorant stabilizer for other colorants. The new porphine compounds, when used as a colorant stabilizer, do not “yellow” magenta dyes. Consequently, unstable dyes, such as Acid Red 52, do not need to be used to make a magenta composition. The result is a more “blue” magenta color and a higher porphine to dye ratio, which creates superior light stability.
The present invention also addresses the needs described above by providing processes of making the above-described porphines at a lower cost and higher yields. The resulting porphines may be used as a colorant stabilizer for a variety of colorants, especially magenta colorants.
The present invention also relates to colorant compositions having improved stability and lightfastness, wherein the colorant is one or more of the new porphine compounds. The present invention also relates to the use of the porphine compounds in ink compositions and ink sets.
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 a new family of porphine compounds having the following general formula:
where M is iron, cobalt or copper; R represents a halogenated alkyl group,
wherein R
1
to R
77
each independently represent —H; a halogen; an alkyl group; a substituted alkyl group; an aryl group; a substituted aryl group; an alkoxy group; a nitrogen-containing group; a sulfur-containing group; —OR′, —NR′R″, or —SR′, wherein R′ and R″ each independently represent an alkyl group, a substituted alkyl group, an aryl group, or a substituted aryl group. Desirably, R
1
to R
77
each independently represent —H; a halogen; an alkyl group; a nitrogen-containing group; or a sulfur-containing group. More desirably, R
1
to R
77
each independently represent —H; chlorine; bromine; fluorine; iodine; a tert-butyl group; —NO
2
; —SO
3
H; —SO
3
Na; —SO
3
Cl; or —SO
3
Cl
−
pyH
+
. Even more desirably, R
1
to R
77
each independently represent —H; chlorine; bromine; fluorine; or iodine. The new compounds may be used alone as an orange/red colorant or may be used as a colorant stabilizer.
The present invention also relates to colorant compositions having improved stability and lightfastness, wherein the colorant constitutes one or more of the above-described porphine compounds. Desirably, one or more of the new porphine compounds are admixed with a solvent system, as well as other composition components. The porphines may be used alone or in combination with at least one metal or metal salt. Suitable metals and metal salts are disclosed in U.S. Pat. No. 5,891,229, assigned to Kimberly Clark Worldwide, Inc., the entirety of which is incorporated herein by reference. As an example, the metal or metal salt in a composition can comprise a lanthanide or lanthanide salt. Moreover, a typical lanthanide or lanthanide salt comprises europium or europium salts. Optionally, the new porphine compounds may be associated with a molecular includant, chelating agent, or other material to improve solubility and/or interaction of the porphine compound and other colorants, if present. Suitable molecular includants, chelating agents, and other composition materials are also disclosed in U.S. Pat. No. 5,891,229. Typical molecular includants with which the porphines may be associated include one or more cyclodextrins, for example &agr;-cyclodextrin, &bgr;-cyclodextrin, &ggr;-cyclodextrin, &dgr;-cyclodextrin, hydroxypropyl &bgr;-cyclodextrin, or hydroxyethyl &bgr;-cyclodextrin.
When used as a colorant stabilizer, the new porphine compounds may be associated with a variety of dyes or colorants. A suitable dye or colorant, for example, may be an organic dye. Organic dye classes include, by way of illustration only, triarylmethyl dyes, such as Malachite Green Carbinol base {4-(dimethylamino)-&agr;-[4-(dimethylamino)phenyl]-&agr;-phenyl-benzene-methanol}, Malachite Green Carbinol hydrochloride {N-4-[[4-(dimethylamino)phenyl]phenyl-methylene]-2,5-cyclohexyldien-1-ylidene]-N-methyl-methanaminium chloride or bis&
MacDonald John G.
Nohr Ronald Sinclair
Kilpatrick & Stockton LLP
Kimberly--Clark Worldwide, Inc.
Klemanski Helene
LandOfFree
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