Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
1998-12-22
2001-10-16
Dees, Jose′ G. (Department: 1615)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C548S546000, C424S070100, C424S070200, C424S070400, C424S070600, C424S070900, C424S070110, C424S070122, C424S070130, C424S070170, C424S078030, C424S400000, C424S401000, C564S153000
Reexamination Certificate
active
06303794
ABSTRACT:
FIELD OF THE INVENTION
This invention relates to water-soluble/dispersible reactive functionalized imido and polyimido compounds, wherein the polyimido compounds may be selected from the group consisting of polysuccinimide compounds, polyglutimide compounds, and copolymers of thereof. The polyimido compound comprises a functionalizing moiety F that provides functionality to the polyimido compound and is preferably derived from a nucleophilic moiety selected from the group consisting of amines, alcohols, phenols, thiols, and carboxylates; and a water-solubilizing/dispersing moiety that provides water-solubility and/or water-dispersibility to the polyimido compound and is preferably derived from a nucleophilic moiety selected from the group consisting of amines, alcohols, phenols, thiols, and carboxylates. The invention also pertains to a proteinaceous substrate to which the imido or polyimido compound has been covalently bonded and to a method for treating a proteinaceous substrate with the imido or polyimido compound.
BACKGROUND OF THE INVENTION
Hair is a proteinaceous substrate containing protein chains connected by sulfur-sulfur cross-linkages from cystine. When hair is bleached or permed, the cystine disulfide bonds are cleaved, typically with sodium thioglycolate, sodium sulfite, or some other disulfide bond-cleaving agent. The hair is then put into a curled or straightened state, whichever is desired, and the disulfide bonds are then allowed to reform. New sulfur-sulfur cross-linkages between the protein chains are formed thus locking the hair into the new array. In practice, not all of the disulfide bonds reform. This cleavage of the sulfur-sulfur cross-linkages results in a weakening of the hair making it more susceptible to breakage during combing and brushing. In addition, because perming formulations are generally very alkaline, some amide linkages in the protein chains are also cleaved resulting in a further weakening of the hair. Currently, there is no cosmetically acceptable method of improving strength by imparting additional cross-linkages to hair. Moreover, both the strength of the hair and the combing properties of the hair are adversely affected by the perming/bleaching process. Conventional treatments to improve the combing properties include various conditioning agents. However, because these conditioning agents do not covalently bond to hair, their conditioning effects are removed by washing and must be repeatedly applied. Improved shine and gloss, UV protection, anti-stat properties, anti-microbial protection, color, as well as many other improvements, which are desirable to intact and/or damaged hair, all suffer from a lack of permanence on hair and must be continually replenished.
While there are many disclosures that describe compositions useful for modifying proteinaceous substrates, none of the disclosures describe compositions that are entirely satisfactory. None of the disclosures describe the preparation of water-soluble or water-dispersible reactive functionalized polyimido compounds that can be covalently and permanently bonded to a proteinaceous substrate. The present invention provides such improved water-soluble or water-dispersible polyimido compounds, many of which, upon reaction, revert to biodegradable and environmentally friendly compounds.
SUMMARY OF THE INVENTION
This invention relates to a polyimido compound selected from the group consisting of polysuccinimide compounds represented by Formula (1):
polyglutimide compounds represented by Formula (2);
and copolymers of the polysuccinimide compounds represented by Formula (1) with the polyglutimide compounds represented by Formula (2); wherein F is a functionalizing moiety that provides functionality to the polyimido compound; W is a water-solubilizing/dispersing moiety that provides water-solubility and/or water-dispersibility to the polyimido compound; the ratio of n
1
:n
2
:n
3
is from about 1:1:98 to about 45:45:10; and the molecular weight of the polyimido compound is from about 300 to about 1,000,000.
This invention also pertains to a proteinaceous substrate, having a polyimido compound covalently bonded to a portion thereof, wherein the polyimido compound is derived from a residue selected from the group consisting of polysuccinimide compounds represented by Formula (1):
polyglutimide compounds represented by Formula (2);
and copolymers of the polysuccinimide compounds represented by Formula (1) with the polyglutimide compounds represented by Formula (2); wherein F is a functionalizing moiety that provides functionality to the polyimido compound; W is a water-solubilizing/dispersing moiety that provides water-solubility and/or water-dispersibility to the polyimido compound; the ratio of n
1
:n
2
:n
3
is from about 1:1:98 to about 45:45:10; and the molecular weight of the polyimido compound is from about 300 to about 1,000,000.
This invention also pertains to a method for treating a proteinaceous substrate which comprises the steps of:
(a) contacting a proteinaceous substrate with an aqueous solution/dispersion of an imido or polyimido compound at a pH value between about 4 and about 7 for a time sufficient to allow the imido or polyimido compound to be adsorbed/absorbed on or into the proteinaceous substrate, wherein the imido or polyimido compound has attached thereto a functionalizing moiety F that provides functionality to the imido or polyimido compound; and
(b) raising the pH value of the imido or polyimido compound adsorbed/absorbed on or into the proteinaceous substrate above about 7 for a time sufficient to allow the imido or polyimido compound to react with the proteinaceous substrate.
This invention also pertains to a method for treating a proteinaceous substrate which comprises the steps of:
(a) contacting a proteinaceous substrate with an aqueous solution of a polyimido compound at a pH value between about 4 and about 7 for a time sufficient to allow the polyimido compound to be adsorbed/absorbed on or into the proteinaceous substrate; and
(b) raising the pH value of the polyimido compound adsorbed/absorbed on or into the proteinaceous substrate above about 7 for a time sufficient to allow the polyimido compound to react with the proteinaceous substrate;
wherein the polyimido compound is selected from the group consisting of polysuccinimide compounds represented by Formula (1):
polyglutimide compounds represented by Formula (2);
and copolymers of the polysuccinimide compounds represented by Formula (1) with the polyglutimide compounds represented by Formula (2);
wherein F is a functionalizing moiety that provides functionality to the polyimido compound; W is a water-solubilizing/dispersing moiety that provides water-solubility and/or water-dispersibility to the polyimido compound; the ratio of n
1
:n
2
:n
3
is from about 1:1:98 to about 45:45:10; and the molecular weight of the polyimido compound is from about 300 to about 1,000,000.
DETAILED DESCRIPTION OF THE INVENTION
The present invention is directed to water-soluble/dispersible reactive functionalized derivatives of polyimido compounds useful for modifying proteinaceous substrates such as hair, wool, skin, leather, silk, fur, felt, and nails. Applicants have found that reaction of a portion of the imide groups in the water-insoluble polysuccinimide (or polyglutimide) with a functionalizing group followed by reaction of another portion of the imide groups with a water-solubilizing nucleophilic agent yields a water-soluble/dispersible functionalized polymer containing reactive sites at the remaining imide moieties. This functionalized water-soluble/dispersible polyimide, containing reactive imide moieties, is a water-soluble/dispersible acylating agent which can now be covalently and permanently reacted with various nucleophilic groups present on the proteinaceous substrate to impart permanent changes to these substrates. Examples of suitable functionalizing groups include antimicrobials, ultraviolet chromophores, dyes, anti-oxidants, fluorescing agents, brightening agents, shine and gloss enhancers, softe
Guth Jacob J.
Howard Doreen
Iovine Carmine
Petersen Paul M.
Thomaides John S.
Dees Jose′ G.
George Konata
Muccino Richard R.
National Starch & Chemical Investment Holding Corp.
LandOfFree
Use of water-soluble/dispersible reactive functionalized... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Use of water-soluble/dispersible reactive functionalized..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Use of water-soluble/dispersible reactive functionalized... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2580783