Polymeric compounds and methods of formulating same

Details Polymeric compounds and methods of formulating same Polymeric compounds and methods of formulating same

2000-11-28

2002-06-25

Dodson, Shelley A. (Department: 1616)

Drug, bio-affecting and body treating compositions

Preparations characterized by special physical form

Wearing apparel, fabric, or cloth

C424S059000, C424S078020, C424S078080, C424S400000, C424S401000

Reexamination Certificate

active

06410040

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to polymeric compounds and methods of formulating same, said polymeric compounds having a polyacrolein sub-unit in aldehyde, hydrated, hemi-acetal or acetal form and having biostatic or biocidal properties. More particularly, the present invention is directed to compositions containing the above noted polymeric compounds and the biostatic and/or biocidal uses of these compositions.
BACKGROUND ART
The broad-based antimicrobial properties of polymers having the repeating polymeric unit:
or this unit in its hydrated, hemi-acetal or acetal form, represented by the formulae:
wherein R is hydrogen or alkyl and n is an integer of one or more have been demonstrated previously (International Patent Application Publication WO 88/04671). The compounds particularly described therein include poly(2-propenal, 2-propenoic acid).
It has also been noted previously (International Patent Application Publication WO 96/38186) that poly(2-propenal, 2-propenoic acid) is formed when the aldehyde groups of poly (2-propenal) syn polyacrolein are partially auto-oxidised to carboxyl groups. It was further noted that the polymer is soluble in dilute aqueous bases, for example aqueous sodium carbonate.
It is known that antimicrobial compositions may be used as preservatives, or as the active ingredients in disinfectants, dermatological compositions including sun screen formulations or antiseptic formulations, or in animal feed additives.
Generally these antimicrobial compositions must:
be stable;
be efficacious in killing micro-organisms within a specified time;
be safe, that is be reasonably free of toxicity which may be caused by the trans-dermal migration of low molecular weight ingredients into the blood-stream so as to manifest toxicity, antigenicity, allergy, irritation or inflammation;
have minimal odour; and
in some dermatological preparations, have the property of sun screening and minimise adverse dermatological sffects from the generation of free-radicals.
Specifically, antimicrobial formulations applied to inanimate objects and the skin are usually termed disinfectants and antiseptics, respectively. Often, regulatory standards demand that a disinfectant formulation first, is stable and secondly, kills a chosen quantum of vegetative micro-organisms within 10 minutes. That is, the antimicrobial activity of these compositions must be biocidal and quick. The formulations described herein are substantially aimed at these goals, but often achieve more, for example killing even extremely resistant bacterial spores within the frequent standard of 24 hours.
Formulation of poly(2-propenal, 2-propenoic acid) simply by dissolution in dilute aqueous sodium carbonate, and then neutralisation to pH 7, has now been found to provide a composition that does not always kill micro-organisms fast enough to meet the above standards.
It is one object of the present invention to provide methods of preparing compositions containing compounds of the type described by the prior art and in particular poly(2-propenal, 2-propenoic acid), and which are useful disinfectants and/or antiseptics meeting these standards.
It is a further object of the present invention to provide a method of preparing polymers and/or copolymers derived from acrolein in accordance with the above mentioned prior art for use as useful disinfectants and/or antiseptics.
It is a still further object of the present invention to provide a method of preparing polymers and/or copolymers derived from acrolein in accordance with the above mentioned prior art, for use in dermatological formulations, including sunscreens.
It is yet still a further object of the present invention to provide a method of preparing polymers and/or copolymers derived from acrolein in accordance with the above mentioned prior art for use in other applications including as a preservative or as an animal feed-additive.
Throughout this specification, unless the context requires otherwise, the word “comprise”, or variations such as “comprises” or “comprising”, will be understood to imply the inclusion of a stated integer or group of integers but not the exclusion of any other integer or group of integers.
DISCLOSURE OF THE INVENTION
In accordance with the present invention there is provided a method for the preparation of compositions of poly(2-propenal, 2-propenoic acid) comprising the method steps of dissolving the poly(2-propenal, 2-propenoic acid) in aqueous base, adding an organic compound containing one or more hydrophobic groups, and subsequently acidifying the solution, whereby interaction between the hydrophobic groups of the organic compound and the poly(2-propenal, 2-propenoic acid) prevents precipitation of the poly(2-propenal, 2-propenoic acid) occurring at pH ≧5.5 and the solution is consequently stable over a broad pH range.
Preferably, the precipitation of the poly(2-propenal, 2-propenoic acid) is prevented at pH ≧3.5.
The organic compound may be an anionic surfactant. The anionic surfactant is preferably selected from either sodium lauryl sulphate or disodium decyl (sulfophoxy) benzene sulfonate and disodium oxybis (decylsulfophenoxy) benzene sulfonate.
In one form of the invention, one or more phenols may be added to the solution of poly(2-propenal, 2-propenoic acid) prior to acidification. The phenol is preferably o-phenyl-phenol.
In a further form of the invention, the composition containing poly(2-propenal, 2-propenoic acid) is firstly stored for a time in basic composition prior to addition of surfactant and acidification.
In a still further form of the invention, the composition exhibits increased antimicrobial activity, the method of preparing the composition comprising preparation of the poly(2-propenal, 2-propenoic acid) in the presence of air and/or oxygen, with or without inhibitor. Alternately, the method comprises the subsequent making of the composition of poly(2-propenal, 2-propenoic acid) into a basic composition.
Preferably, the organic compound is one or more of ethylene diamine tetra acetic acid, a lower alkanol, a phenol, isothiazolinones and glutaraldehyde, the composition exhibiting a synergistic increase in antimicrobial activity.
The composition may further comprise phenols and/or glutaraldehyde, whereby the odour of the phenols and/or glutaraldehyde is reduced by the presence of the poly(2-propenal, 2-propenoic acid).
The composition may exhibit reduced trans-dermal migration of low molecular weight components of the composition as a result of the presence of poly(2-propenal, 2-propenoic acid). The low molecular weight composition may contain a sunscreen agent. The sunscreen agent may be either or both of octyl methoxy cinnamate and octyl dimethyl p-aminobenzoate.
In one form of the invention, the composition, especially for dermatological use, exhibits a sunscreening effect as a result of the presence of poly(2-propenal, 2-propenoic acid).
In another form of the invention, the composition exhibits the formation of a continuous antimicrobial film on substrates.
In another form of the invention, the composition, especially for dermatological use exhibits a free-radical scavenging effect as the result of the presence of poly(2-propenal, 2-propenoic acid).
In accordance with the present invention there is provided an aqueous polymeric composition comprising poly(2-propenal, 2-propenoic acid) and an organic compound containing one or more hydrophobic groups, wherein interaction between the hydrophobic groups of the organic compound and the poly(2-propenal, 2-propenoic acid) prevents the precipitation of the poly(2-propenal, 2-propenoic acid) at pH >5.5.
Preferably, the poly(2-propenal, 2-proppnoic acid) does not precipitate at a pH 2 3.5.
Still preferably, the organic compound is an anionic surfactant. The anionic surfactant may be chosen from either sodium lauryl sulphate or disodium decyl (sulfophoxy) benzene sulfonate and disodium oxybis (decylsulfophenoxy) benzene sulfonate.
The composition may further comprising one or more phenol. The phenol may be o-phenyl-phenol.
In one form of

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