Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system
Reexamination Certificate
2000-01-06
2002-07-30
Shah, Mukund J. (Department: 1624)
Organic compounds -- part of the class 532-570 series
Organic compounds
Four or more ring nitrogens in the bicyclo ring system
C544S031000, C544S032000, C544S100000, C544S101000, C544S102000, C546S061000, C546S062000, C528S332000, C528S391000
Reexamination Certificate
active
06426416
ABSTRACT:
FIELD OF INVENTION
This invention concerns organic materials particularly metal free organic compounds which are anthraquinone and condensed anthraquinone colorants, which compounds have linked thereto through sulfonamide groups, one or more poly(oxyalkylene) moieties which impart to or improve one or more chemical or physical properties of the compounds such as liquidity, solvent solubility, compatibility with liquids, with thermosettable resinous materials, or with thermoplastic polymeric materials, primary hydroxyl enrichment, hydroxyl reactivity enchancement, branching density or melting point lowering.
The utility and desirability in a general sense for incorporating certain poly(oxyalkylene) materials into organic compounds, particularly into colorant compounds, are disclosed in the literature such as in U.S. Pat. Nos.: 4,761,502; 4,284,729; 4,751,254; 4,812,141; 4,167,510; 4,141,684; 3,157,633; and 4,640,690, the disclosures of which are hereby incorporated by reference. All of these patents teach the linking of the poly(oxyalkylene) moiety to the chromophore through amino groups since the standard method for associating the poly(oxyalkylene) with a compound is through the reaction of the epoxy reactant with an amino group on the compound. However, such a reaction is not always convenient as such amino groups are not easily placed on many organic compounds.
In regard to the new colorant compositions of the present invention, an important utility for one embodiment is for the tinting or deeper coloring of natural and synthetic polymeric or resinous materials or substrates, especially polyurethanes and other thermosetting resins and polyolefins, wherein the chemical structures of the colorants are readily tailored to meet, in exceptional manner, the physical and chemical requirements of the specific industrial application.
Some of the desired physical and chemical characteristics of such colorants, in addition to having at least substantial tinctorial power, include one or more of excellent clarity and light fastness, high heat stability, crystal structure and shade immutability, availability as liquids or at least good resin compatibility at processing temperatures for easy blending with the substrate, easy clean-up from processing, homogeneity of dispersal in the substrate, non-nucleating propensity of the colorant, and resistance to migration, settling, streaking, plating, subliming, blooming and the like of the colorant from the substrate.
The present organic materials on the other hand, for the most part are polymeric, amorphous liquids and the liquid colorant system eliminates the dusting problems from various substrates. The polymeric nature also makes the colorant more compatible with the various cleaning chemicals due to its unique, internal emulsifying constituents.
Objects therefore of the present invention are: to provide organic materials, especially colorants which are improved in one or more properties such as liquidity, solvent solubility, pH stability, compatibilty with liquids, with thermosetting materials, or with thermoplastic materials, primary hydroxyl enrichment, hydroxyl reactivity enchancement, or melting point lowering; or non-fiber or non-skin staining; and to provide a highly simplified method for their manufacture.
SUMMARY OF THE INVENTION
These and other objects have been attained in accordance with the present invention defined in its process embodiment as the process for chemically modifying metal-free, organic material for improving one or more properties thereof such as water dispersibility, compatibility with other organics, or increased chemical reactivity, said process comprising providing said material having from 1-6 sulfonylhalide groups or sulfonate ester groups or mixtures thereof, and contacting the same under sulfonamido forming conditions with one or more reactants containing one or more poly(oxyalkylene) moieties, each said reactant having from 1 to 4 functional amine groups, and each said poly(oxyalkylene) moiety being comprised of from about 6 to about 200 epoxide reactant residues of 2-4 carbons.
In certain preferred embodiments:
said poly(oxyalkylene) moiety contains a total of from about 3.0 to about 30 mole percent of epoxide residue linking groups selected from one or more of divalent or trivalent, straight or branched aliphatic hydrocarbon of 2-15 carbons, alkylenedioxy, alkylenetrioxy, or groups containing one or more of N, O or S or combinations thereof;
said residue linking groups are selected from —NR
1
—, NR
1
SO
2
NR
1
— or —NH—C(═O)—NH—, wherein R
1
is selected from hydrogen, a poly(oxyalkylene) moiety as defined, or unsubstituted or substituted alkyl, aryl, or cycloalkyl; said amine groups have the formula HN(R
1
)— wherein R
1
is selected from hydrogen, a poly(oxyalkylene) moiety as defined, or unsubstituted or substituted alkyl, aryl, or cycloalkyl; and said organic material contains one or more of the unsubstituted or substituted reaction residues of anthraquinone or condensed anthraquinone compounds. Certain other preferred embodiments of the method and composition are given in the appended claims.
In the above definitions, Y can be terminated by H, or by or contain as branch substituents, 1-3 groups or moieties selected from alkyl, cycloalkyl, acyl, or aryl; any of the above recited hydrocarbon groups, moieties or substituents may themselves be substituted, for example, or may contain multiple substituents selected from alkyl, halogen, alkoxycarbonyl, hydroxy alkoxy, alkylenedioxy, urea or substituted urea, amino or substituted amino, acylamino or substituted acylamino, acyloxy or the like substituents which are known in the art; and each aliphatic hydrocarbon portion or moiety of the groups, moieties or substituents recited above, where not otherwise specified, contains from 1-20, preferrably 1-12 carbons. In certain preferred embodiments however, it is preferred that the poly(oxyalkylene) moiety carries substantial hydroxyl functionality, and for certain utilities the hydroxyl functionality is most preferably patterned in a more dense manner.
It is noted and is shown in the various examples of the preformed poly(oxyalkylene) containing reactants that the poly(oxyalkylene) moieties which naturally terminate with hydrogen at the end of the epoxide polymerization have been reacted further with materials such as ammonia. Also, additional groups can be added during poly(oxyalkylene) preparation by selection of the various nucleophiles to be reacted with the epoxide reactants.
Also such groups, e.g., ketals may be subsequently hydrolyzed and further reacted such as acylation, or amination. Such nucleophiles are shown in the reactant examples given below. Such groups are exemplified by alkoxy, phenoxy, dihydroxyalkyl, hydroxyalkyl, cyclic acetal (dihydroxy compound reacted with ketone), aminoaklyl, acyloxyalkyl or diacyloxyalkyl.
It is noted that one of the primary purposes of the present invention is to provide polymeric colorants which color thermoplastic and thermosetting resins without settling, streaking, subliming, or migrating and which provide uniform coloring throughout the entire resin. Also, the present polymeric colorants often provide improved clarity over conventional pigments. In addition, it is highly desirable that the colorants be easily removed from the equipment used to add the colorant to the resin. We have found the present colorants can be used to color homogeneously a variety of thermoplastics and thermosetting resins and that aqueous cleaning is greatly facilitated as compared to conventional colorants.
DISCUSSION OF PRIOR ART
U.S. Pat. No. 2,730,534 shows anthraquinone dyestuffs useful for dyeing textile fibers and which contain —SO
2
NH(CH
2
CH
2
O)
n
—H groups where n equals 1, 2 or 3. These compounds, however, are solids and quite insoluble in water and thus are primarily useful as disperse dyestuffs.
Also, it is known to prepare polymeric colorants containing sulfonamido groups which link the chromophore to a polymeric portion (see U.S. Pat. Nos.: 4,051,038; 4,144,252; 4,16
Kluger Edward William
Moody David Jesse
Weaver Max Allen
Millikan & Companay
Monahan Timothy J.
Moyer Terry T.
Shah Mukund J.
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