Drug – bio-affecting and body treating compositions – Preparations characterized by special physical form – Cosmetic – antiperspirant – dentifrice
Reexamination Certificate
1998-06-09
2003-01-21
Page, Thurman K. (Department: 1615)
Drug, bio-affecting and body treating compositions
Preparations characterized by special physical form
Cosmetic, antiperspirant, dentifrice
C424S065000, C514S564000, C514S565000, C514S631000, C514S634000, C514S635000
Reexamination Certificate
active
06509022
ABSTRACT:
The present invention relates to organic acid salts of polymeric biguanides for use in personal care applications.
Poly(hexamethylenebiguanide) (hereinafter PHMB) has found many uses as a broad spectrum bactericide in both industrial and personal care applications and is commercially available as an aqueous concentrate of its hydrochloride salt. For most applications, the use of PHMB in the form of its hydrochloride salt is eminently suitable. There are, however, some applications where the presence of chloride ion can cause undesirable side effects such as corrosion of metal surfaces. GB 1,464,005 discloses that other salts of PHMB such as sulphate, acetate, gluconate and behenate, may be used as molluscicides. However, no microbiological data are recorded for such salts. Behenic acid is an aliphatic carboxylic acid containing a C
21
-alkyl chain and salts thereof fall within the group of anionic surfactants. The concentrated aqueous solution of PHMB in the form of its hydrochloride salt is clearly stated to be incompatible with anionic surfactants, such as alkyl sulphonates and anionic caramels as disclosed in the Product Information Notes for Vantocil IB (37-8E dated Jun. 1, 1994) and Cosmocil CQ (37-26E dated Apr. 1, 1994). Both Vantocil and Cosmocil are registered trade marks of Zeneca Specialties for PHMB hydrochloride.
Bisbiguanides have also been made available commercially as water-soluble salts such as chlorhexidine (1,1′-hexamethylene bis [5-(4-chlorophenyl)-biguanide]digluconate) and alexidine (1,1′-hexamethylene bis [5(4-(2-ethylhexyl)phenyl)-biguanide]-diacetate). These water-soluble salts and PHMB hydrochloride are not particularly suited to provide a solution of the polymeric biguanide in organic liquids, especially non-polar organic liquids, and do no cause significant corrosion.
It has now been found that PHMB in the form of its salt of an organic acid containing from 4 to 30 carbon atoms exhibits high antimicrobial, especially antibacterial activity, and that such salts exhibit increased solubility in organic media, especially organic liquids.
According to the present invention there is provided a composition comprising a carrier and a polymeric biguanide in the form of its salt with an organic acid containing from 4 to 30 carbon atoms, including mixtures thereof for use in personal care formulations. The polymeric biguanide contains at least one biguanide unit of Formula 1.
Preferably, the polymeric biguanide contains at least two biguanide units of Formula 1 which are linked by a bridging group which contains at least one methylene group. The bridging group may include a polymethylene chain which may optionally be interrupted by hetero atoms such as oxygen, sulphur or nitrogen. The bridging group may include one or more cyclic nuclei which may be saturated or unsaturated. Preferably, the bridging group is such that there are at least three, and especially at least four, carbon atoms directly interposed between two adjacent biguanide units of Formula 1. Preferably, there are not more than ten and especially not more than eight carbon atoms interposed between two adjacent biguanide units of Formula 1.
The polymeric biguanide may be terminated by a suitable group which may be a hydrocarbyl or substituted hydrocarbyl group or an amine or a group of the formula
When the terminating group is a hydrocarbyl group, it may be an alkyl, cycloalkyl or aralkyl group.
When the terminating group is a substituted hydrocarbyl group, the substituent may be any substituent which does not exhibit an undesirable adverse effect on the microbiological properties of the polymeric biguanide. Examples of suitable substituents or substituted hydrocarbyl groups are aryloxy, alkoxy, acyl, acyloxy, halogen and nitrile groups or substituents.
When the polymeric biguanide contains two biguanide groups of Formula 1, the two biguanide units are preferably linked by a polymethylene group, especially a hexamethylene group. The terminating group in such polymeric biguanides is preferably 4-chlorophenyl or 2-ethylhexyl. Examples of such compounds are represented by Formulae 2 and 3 in their free base form
The polymeric biguanide preferably contains more than two biguanide units of Formula 1 and preferably is a linear polymeric biguanide which has a recurring polymeric unit represented by Formula 4
wherein X and Y may be the same or different and represent bridging groups in which, together, the total number of carbon atoms directly interposed between the pairs of nitrogen atoms linking a pair of bridging groups is not less than 9 and not greater than 17.
The bridging groups X and Y may consist of a polymethylene chain, optionally interrupted by a heteroatom such as oxygen, sulphur or nitrogen. X and Y may also incorporate a cyclic nucleus which may be saturated or unsaturated, wherein the number of carbon atoms directly interposed between the pairs of nitrogen atoms linked by X and Y is taken as including that segment of the cyclic group, or groups, which is the shortest. Thus, the number of carbon atoms directly interposed between the nitrogen atoms in the group
is 4 and not 8.
The preferred polymeric biguanide for use in the present invention is poly(hexamethylenebiguanide), in which both X and Y in Formula 4 are the group —(CH
2
)
6
—.
The polymeric biguanides of Formula 4 are typically obtained as mixtures of polymers in which the polymer chains are of different lengths. Preferably, the number of individual biguanide units
is, together, from 3 to about 80.
In the case of the preferred poly(hexamethylenebiguanide) it is a mixture represented by the compounds of Formula 5 in the free-base form.
wherein the value of n is from 4 to 40 and especially from 4 to 15. It is particularly preferred that the average value of n in the mixture is 12. Preferably, the average molecular weight of the polymer mixture is from 1100 to 3300.
The organic acid which forms the salt with the polymeric biguanide may contain a phosphonic, phosphoric, sulphonic or sulphuric group but preferably contains a carboxylic acid group. The organic acid may be aromatic but is preferably aliphatic, including alicyclic. When the organic acid is aliphatic, the aliphatic chain of the organic acid may be linear or branched, saturated or unsaturated, including mixtures thereof. Preferably, the aliphatic chain is linear and it is also preferred that the organic acid is an aliphatic carboxylic acid.
It is preferred that the organic acid contains not less than eight, more preferably not less than ten and especially not less than twelve carbon atoms excluding the acid group. Preferably, the organic acid contains not more than 24, more preferably not more than 20 and especially not more than 18 carbon atoms excluding the acid group.
The organic acid may contain more than one acid group but it is preferred that only one such group is present.
The organic acid may be substituted by a halogen or particularly a hydroxy group. It is, however, preferred that the organic acid is free from substituents.
Some aliphatic carboxylic acids are available commercially as mixtures such as those obtained from animal fats and vegetable oils and these contain both staturated and unsaturated aliphatic chains. These have also been found useful, especially the C
14-18
alkyl carboxylic acids and their fully saturated or hydrogenated analogues.
Examples of optionally substituted carboxylic acids are valeric, hexanoic, octanoic, 2-octanoic, lauric, 5-dodecenoic, myristic, pentadecanoic, palmitic, oleic, stearic, eicosanoic, heptadecanoic, palmitoleic, ricinoleic, 12-hydroxystearic, 16-hydroxyhexadecanoic, 2-hydroxycaproic, 12-hydroxydodecanoic, 5-hydroxydodecanoic, 5-hydroxydecanoic, 4-hydroxydecanoic, dodencanedioic, undecanedioic, sebacic, benzoic, hydroxybenzoic and terephthalic acids.
Particularly useful effects have been obtained when the aliphatic carboxylic acid is stearic acid and the polymeric biguanide is PHMB.
The amount of the polymeric biguanide salts in the composition may vary between wide limits depending
Lowry Michael Richard
Parker Katherine Elizabeth
Channavajjala Lakshmi
Helene Curtis Inc.
Page Thurman K.
Stein Kevin J.
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