Antibacterial antiplaque oral composition

An oral composition dentifrice containing an orally acceptable vehicle, about 30-75% by weight of a dentally acceptable water-insoluble polishing agent, a substantially water-insoluble noncationic antibacterial antiplaque agent, such as 2,4,4'-trichloro-2'-hydroxy-diphenyl ether (triclosan) an antibacterial enhancing agent which enhances the delivery of said antibacterial agent to, and retention thereof on, oral surfaces, and a surface active agent and/or a flavoring oil.

This invention relates to an antibacterial antiplaque oral composition 
dentifrice. More particularly, it relates to an oral composition 
dentifrice containing a substantially water-insoluble noncationic 
antibacterial agent effective to inhibit plaque. 
Dental plaque is a soft deposit which forms on teeth as opposed to calculus 
which is a hard calcified deposit on teeth. Unlike calculus, plaque may 
form on any part of the tooth surface, particularly including at the 
gingival margin. Hence, besides being unsightly, it is implicated in the 
occurrence of gingivitis. 
Accordingly, it is highly desirable to include antimicrobial agents which 
have been known to reduce plaque in oral compositions. Frequently, 
cationic antibacterial agents have been suggested. Moreover, in U.S. Pat. 
No. 4,022,880 to Vinson et al, a compound providing zinc ions as an 
anticalculus agent is admixed with an antibacterial agent effective to 
retard the growth of plaque bacteria. A wide variety of antibacterial 
agents are described with the zinc compounds including cationic materials 
such as guanides and quaternary ammonium compounds as well as non-cationic 
compounds such as halogenated salicylanilides and halogenated 
hydroxydiphenyl ethers. The noncationic antibacterial antiplaque 
halogenated hydroxydiphenyl ether, triclosan, has also been described in 
combination with zinc citrate trihydrate in European Patent Publication 
0161,899 to Saxton et al. Triclosan is also disclosed in European Patent 
Publication 0271,332 to Davis as a toothpaste component in a carrier 
system containing a solubilizing agent such as propylene glycol. 
The cationic antibacterial materials such as chlorhexidine, benzathonium 
chloride and cetyl pyridinium chloride have been the subject of greatest 
investigation as antibacterial antiplaque-agents. However, they are 
generally not effective when used with anionic materials. Noncationic 
antibacterial materials, on the other hand, can be compatible with anionic 
components in an oral composition. 
However, oral compositions typically are mixtures of numerous components 
and even such typically neutral materials as humectanis can affect 
performance of such compositions. 
Moreover, even noncationic antibacterial antiplaque agents may have limited 
antiplaque effectiveness with commonly used materials such as 
polyphosphate anticalculus agents which are disclosed together in British 
Patent Publication 22 00551 of Gaffar et al and in EP 0251591 of Jackson 
et al. In commonly assigned Ser. No. 398,605 filed on even date herewith, 
titled "Antibacterial, Antiplaque Anticalculus Oral Composition", it is 
shown that the antiplaque effectiveness is greatly enhanced by including 
an antibacterial-enhancing agent (AEA) which enhances the delivery of said 
antibacterial agent to, and retention thereof on, oral surfaces, and 
providing optimized amounts and ratios of polyphosphate and AEA. 
Further, even when polyphosphate anticalculus agent is not present as in 
commonly assigned Ser. No. 398,606 filed on even date herewith, titled 
"Antibacterial Antiplaque Oral Composition", antiplaque effectiveness on 
soft oral tissue is optimized by including with the AEA a solubilizing 
material which dissolves the noncationic antibacterial agent in saliva 
when the polishing agent is a siliceous polishing agent present in amount 
of about 5-30%. Indeed, when the amount of noncationic antibacterial agent 
is optimized, even the special solubilizing material is not required, as 
in commonly assigned Ser. No. 398,566, filed on even date herewith, titled 
"Antiplaque Antibacterial Oral Composition". 
It is an advantage of this invention that an oral composition dentifrice 
containing an effective antiplaque amount of a substantially 
water-insoluble noncationic antibacterial antiplaque agent and said AEA to 
inhibit plaque formation and a dentally acceptable water-insoluble 
polishing agent in amount of about 30-75% is provided, wherein 
polyphosphate anticalculus agent is not present. 
It is an advantage of this invention that the said AEA enhance the delivery 
and retention of the antibacterial agent on teeth and on soft oral tissues 
but Examples 1 and 3 contain 0.5-2% propylene glycol without requiring the 
presence of a material which dissolves the antibacterial agent in saliva. 
It is a further advantage of this invention at an antiplaque oral 
composition is provided which is directly or indirectly effective to 
reduce the occurrence of gingivitis. 
Additional advantages of this invention will be apparent from consideration 
of the following specification. 
In accordance with certain of its aspects, this invention relates to an 
oral composition dentifrice comprising in an orally acceptable vehicle, 
about 30-75% of a dentally acceptable water-insoluble polishing agent, an 
effective antiplaque active ingredient amount of a substantially water 
insoluble noncationic antibacterial agent, said oral composition 
dentifrice comprising at least one of a surface-active agent or a 
flavoring oil and 7 about 0.05-4% by weight of said AEA wherein said oral 
composition dentifrice is substantially free of polyphosphate anticalculus 
agent. 
Typical examples of water insoluble noncationic antibacterial agents which 
are particularly desirable from considerations of antiplaque 
effectiveness, safety and formulation are: 
Halogenated Diphenyl Ethers 
2',4,4'-trichloro-2'-hydroxy-diphenyl ether (Triclosan) 
2,2'-dihydroxy-5,5'-dibromo-diphenyl ether. 
Halogenated Salicylanilides 
5-dibromosalicylanilide 
3,4',5-trichlorosalcylanilide 
3,4',5-tribromosalicylanilide 
2,3,3',5-tetrachlorosalicylanilide 
3,3,3',5-tetrachlorosalicylanilide 
3,5-dibromo-3'-irifluoromethyl salicylanilide 
5-n-octanoyl-3'-trifluoromethyl salicylanilide 
3,5-dibromo-4'-trifluoromethyl salicylanilide 
3,5-dibromo-3'-trifluoro methyl salicylanilide (Flurophene) 
Benzoic Esters 
Methyl - p-Hydroxybenzoic Ester 
Ethyl - p-Hydroxybenzoic Ester 
Propyl - p-Hydroxybenzoic Ester 
Butyl - p-Hydroxybenzoic Ester 
Halogenated Carbanilides 
3,4,4'-trichlorocarbanilide 
3-trifluoromethyl-4,4'-dichlorocarbanilide 
3,3,4'-trichlorocarbanilide 
Phenolic Compounds (including phenol and its homologs, mono- and polyalkyl 
and aromatic halo (e.g. F, Cl, Br, I)-phenols, resorcinol and catechol and 
their derivatives and bisphenolic compounds). Such compounds include inter 
alia: 
Phenol and its Homologs 
Phenol 
Methyl - Phenol 
Methyl - Phenol 
Methyl - Phenol 
Ethyl - Phenol 
2,4-Dimethyl - Phenol 
2,5-Dimethyl - Phenol 
3,4-Dimethyl - Phenol 
2,6-Dimethyl - Phenol 
4-n Propyl - Phenol 
4-n-Butyl - Phenol 
4-n-Amyl - Phenol 
4-tert-Amyl - Phenol 
4-n-Hexyl - Phenol 
4-n-Heptyl - Phenol 
2-Methoxy-4-(2-Propenyl)-Phenol (Eugenol) 
2-Isopropyl-5-Methyl - Phenol (Thymol) 
Mono- and Poly-Alkyl and Aralkyl Halophenols 
Methyl - p-Chlorophenol 
Ethyl - p-Chlorphenol 
n-Propyl - p-Chlorophenol 
n-Butyl - p-Chlorophenol 
n-Amyl - p-Chlorophenol 
sec-Amyl - p-Chlorophenol 
n-Hexyl - p-Chlorophenol 
Cyclohexy - p-Chlorophenol 
n-Heptyl - p-Chlorophenol 
n-Octyl - p-Chlorophenol 
O-Chlorophenol 
Methyl - o-Chlorophenol 
Ethyl - o-Chlorophenol 
n-Propyl - o-Chlorophenol 
n-Butyl - o-Chlorophenol 
n-Amyl - o-Chlorophenol 
tert-Amyl - o-Chlorophenol 
n-Hexyl - o-Chlorophenol 
n-Heptyl - o-Chloropenol 
p-Chlorophenol 
o-Benzyl - p-Chlorophenol 
o-Benzyl-m-methyl - p-Chlorophenol 
o-Benzyl-m, m-dimethyl - p-Chlorophenol 
o-Phenylethyl - p-Chlorophenol 
o-Phenylethyl-m-methyl - p-Chlorophenol 
3-Methyl - p-Chlorophenol 
3,5-Dimethyl - p-Chlorophenol 
6-Ethyl-3-methyl - p-Chlorophenol 
6-n-Propyl-3-methyl - p-Chlorophenol 
6-iso propyl-3-methyl - p-Chlorophenol 
2-Ethyl-3,5-dimethyl - p-Chlorophenol 
6-sec Butyl-3-methyl - p-Chlorophenol 
2-iso-Propyl-3,5-dimethyl - p-Chlorophenol 
6-Diethylmethyl-3-methyl - p-Chlorophenol 
6-iso-Propyl-2-ethyl-3-methyl - p-Chlorophenol 
2-sec Amyl-3,5-dimethyl - p-Chlorophenol 
2-Diethylmethyl-3,5-dimethyl - p-Chlorophenol 
6-sec Octyl-3-methyl - p-Chlorophenol 
p-Bromophenol 
Methyl - p-Bromophenol 
Ethyl - p-Bromophenol 
n-Propyl - p-Bromophenol 
n-Butyl - p-Bromophenol 
n-Amyl - p-Bromophenol 
sec-Amyl - p-Bromophenol 
n-Hexyl - p-Bromophenol 
cyclohexyl - p-Bromophenol 
o-Bromophenol 
tert-Amyl - o-Bromophenol 
n-Hexyl - o-Bromophenol 
n-Propyl-m,m-Dimethyl - o-Bromophenol 
-Phenyl Phenol 
4-Chloro-2-methyl phenol 
4-chloro-3-methyl phenol 
4-chloro-3,5-dimethyl phenol 
2,4-dichloro-3,5-dimethyl phenol 
3,4,5,6-tetrabromo-2-methylphenol 
5-methyl-2-pentylphenol 
4-isopropyl-3-methylphenol 
5-chloro-2-hydroxydiphenyl methane 
Resorcinol and Its Derivatives 
Resorcinol 
Methyl - Resorcinol 
Ethyl - Resorcinol 
n-Propyl - Resorcinol 
n-Butyl - Resorcinol 
n-Amyl - Resorcinol 
n-Hexyl - Resorcinol 
n-Heptyl - Resorcinol 
n-Octyl - Resorcinol 
n-Nonyl - Resorcinol 
Phenyl - Resorcinol 
Benzyl - Resorcinol 
Phenylethyl - Resorcinol 
Phenylpropyl - Resorcinol 
p-Chlorobenzyl - Resorcinol 
5-Chloro -2,4-Dihydroxydiphenyl Methane 
4'-Chloro -2,4-Dihydroxydiphenyl Methane 
5-Bromo -2,4-Dihydroxydiphenyl Methane 
4'-Bromo -2,4-Dihydroxydiphenyl Methane 
Bisphenolic Compounds 
Bisphenol A 
2,2'-methylene bis (4-chlorophenol) 
2,2'-methylene bis (3,4,6-trichlorophenol) (hexachlorophene) 
2,2'-methylene bis (4-chloro-6-bromophenol) 
bis (2-hydroxy-3,5-dichlorophenyl) sulfide 
bis (2-hydroxy-5-chlorobenzyl) sulfide 
The noncationic antibacterial agent is present in the oral composition in 
an effective antiplaque amount, typically about 0.01-5% by weight, 
preferably about 0.03-1% and more preferably about 0.3-0.5%. The 
antibacterial agent is substantially water-insoluble, meaning that its 
solubility is less than about 1% by weight in water at 25.degree. C. and 
may be even less than about 0.1%. 
The preferred halogenated diphenyl ether is triclosan. The preferred 
phenolic compounds are phenol, thymol, eugenol, hexyl resorcinol and 
2,2'methylene bis (4-chloro-6-bromophenol). The most preferred 
antibacterial antiplaque compound is triclosan. Triclosan is disclosed in 
aforementioned U.S. Pat. No. 4,022,880 as an antibacterial agent in 
combination with an anticalculus agent which provides zinc ions and in 
German Patent Disclosure 3532860 in combination with a copper compound. In 
European Patent Disclosure 0278744 it is disclosed in combination with a 
tooth desensitizing agent containing a source of potassium ions. It is 
also disclosed as an antiplaque agent in a dentifrice formulated to 
contain a lamellar liquid crystal surfactant phase having a lamellar 
spacing of less than 6.0 nm and which may optionally contain a zinc salt 
in published European Patent Application 0161898 of Lane et al and in a 
dentifrice containing zinc citrate trihydrate in published European Patent 
Application 0161899 to Saxton et al. 
The antibacterial-enhancing agent (AEA) which enhances delivery of said 
antibacterial agent to, and retention thereof on, oral surfaces, is 
employed in amounts effective to achieve such enhancement within the range 
in the oral composition of about 0.05 to about 4%, preferably about 0.1% 
to about 3%, more preferably about 0.5% to about 2.5% by weight. 
AEA polymeric materials of the present invention include those which can be 
characterized as having utility as dentifrice adhesives or fixatives or 
dental cements. For example, U.S. Pat. Nos. 4,521,551 and 4,375,036, each 
to Chang et al, describe commercially available copolymer of methylvinyl 
ether-maleic anhydrie (Gantrez) as a dentured fixative. However, there has 
not been recognition in the prior art that adhesives, fixatives or cements 
when applied in water-soluble or water-swellable form together with 
substantially water-insoluble non-cationic antibacterial antiplaque agents 
could enhance the antibacterial activity of such agents. Further, in U.S. 
Pat. No. 4,485,090 to Chang, Gantrez AN copolymer is mentioned among 
polymeric anionic membrane-forming materials which attach to a tooth 
surface to form a hydrophobic barrier which reduces elution of a 
previously applied therapeutic caries prophylactic fluoride compound. 
Again, there is no recognition that such polymeric material could enhance 
the antibacterial activity of substantially water-insoluble non-cationic 
antibacterial antiplaque agents. 
This AEA may be a simple compound, preferably a polymerizable monomore, 
more preferably a polymer, which latter term is entirely generic, 
including for example oligomers, homopolymers, copolymers of two or more 
monomers, block copolymers, graft copolymers, cross-linked polymers and 
copolymers, and the like. The AEA may be natural or synthetic, and water 
insoluble or preferably water (saliva) soluble or swellable (hydratable, 
hydrogel forming). It has an (weight) average molecular weight of about 
100 to about 1,000,000, preferably about 1,000 to about 1,000,000, more 
preferably about 2,000 or 2,500 to about 250,000 or 500,000. 
The AEA ordinarily contains at least one delivery-enhancing group, which is 
preferably acidic such as sulfonic, phosphinic, or more preferably 
phosphonic or carboxylic, or salt thereof, e.g. alkali metal or ammonium, 
and at least one organic retention-enhancing group, preferably a plurality 
of both the delivery-enhancing and retention-enhancing groups, which 
latter groups preferably have the formula --(X).sub.n -R wherein X is O, 
N, S, SO, SO.sub.2, P, PO or Si or the like, R is hydrophobic alkyl, 
alkenyl, acyl, aryl, alkaryl, aralkyl, heterocyclic or their 
inert-substituted derivatives, and n is zero or 1 or more. The aforesaid 
"inert-substituted derviatives ", are intended to include substituents on 
R which are generallynon-hydrophilic and done significantly interfere with 
the desired functions of the AEA as enhancing the delivery of the 
antibacterial agent to, and retention thereof on, oral surfaces such as 
halo, e.g. Cl, Br, I, and carbon and the like. Illustrations of such 
retention-enhancing groups are tabulated below. 
______________________________________ 
n X --(X).sub.n R 
______________________________________ 
0 -- methyl, ethyl, propyl, butyl, isobutyl, t-buryl, 
cyclohexyl, allyl, benzyl, phenyl, chlorophenyl, xylyl, 
pyridyl, furanyl, acetyl, benzoyl, butyryl, 
terephthaloyl, etc. 
1 0 ethoxy, benzyloxy, thioacetoxy, phenoxy, 
carboethoxy, carbobenzyloxy, etc. 
N ethylamino, diethylamino, propylamido, benzylamino, 
benzoylamido, phenylacetamido, etc. 
S thiobutyl, thioisobutyl, thioallyl, thiobenzyl, thiophenyl, 
thiopropionyl, phenylthioacetyl, thiobenzoyl, etc. 
SO butylsulfoxy, allylsulfoxy, benzylsulfoxy, 
phenylsulfoxy, etc. 
SO.sub.2 
butylsulfonyl, allysulfonyl, benzylsulfonyl, 
phenylsulfonyl, etc. 
P diethyphosphinyl, ethylvinylphosphinyl, 
ethylallylphosphinyl, ethylbenzylphosphinyl, 
ethylphenylphosphinyl, etc. 
PO diethylphosphinoxy, ethylvinylphosphinoxy, 
methylallylphosphinoxy, methylbenzyphosphinoxy, 
methylphenylphosphinoxy, etc. 
Si trimethysilyl, dimethylbutylsilyl, dimethylbenzylsilyl, 
dimethylvinylsilyl, dimethylallylsilyl, etc. 
______________________________________ 
As employed herein, the delivery-enhancing group refers to one which 
attaches or substantively, adhesively, cohesively or otherwise bonds the 
AEA (carrying the antibacterial agent) or oral (e.g. tooth and gum) 
surfaces, thereby "delivering" the antibacterial agent to such surfaces. 
The organic retention-enhancing group, generally hydrophobic, attaches or 
otherwise bonds the antibacterial agent to the AEA, thereby promoting 
retention of the antibacterial agent to the AEA and indirectly on the oral 
surfaces. In some instances, attachment of the antibacterial agent occurs 
through physical entrapment thereof by the AEA, especially when the AEA is 
a cross-linked polymer, the structure of which inherently provides 
increased sites for such entrapment. The presence of a higher molecular 
weight, ore hydrophobic cross-linking moiety in the cross-linked polymer 
still further promotes the physical entrapment of the antibacterial agent 
to or by the cross-linked AEA polymer. 
Preferably, the AEA is an anionic polymer comprising a chain or backbone 
containing repeating units each preferably containing at least one carbon 
atom and preferably at least one directly or indirectly pendant, 
monovalent delivery-enhancing group and at least one directly or 
indirectly pendant monovalent retention-enhancing group geminally, 
vicinally or less preferably otherwise bonded to atoms, preferably carbon, 
in the chain. Less preferably, the polymer may contain delivery-enhancing 
groups and/or retention-enhancing groups and/or other divalent atoms or 
groups as links in the polymer chain instead of or in addition to carbon 
atoms, or as crosslinking moieties. 
It will be understood that any examples or illustrations of AEA's disclosed 
herein which do not contain both delivery-enhancing groups and retention 
enhancing groups may and preferably should be chemically modified in known 
manner to obtain the preferred AEA's containing both such groups and 
preferably a plurality of each such groups. In the case of the preferred 
polymeric AEA's, it is desirable, for maximizing substantivity and 
delivery of the antibacterial agent to oral surfaces, that the repeating 
units in the polymer chain or backbone containing the acidic delivery 
enhancing groups constitute at least about 10%, preferably at least about 
50% more preferably at least about 80% up to 95% or 100% by weight of the 
polymer. 
According to a preferred embodiment of this invention, the AEA comprises a 
polymer containing repeating units in which one or more phosphonic acid 
delivery-enhancing groups are bonded to one or more carbon atoms in the 
polymer chain. An example of such an AEA is poly (vinyl phosphonic acid) 
containing units of the formula: 
##STR1## 
which however does not contain a retention-enhancing group. A group of the 
latter type would however be present in poly (1-phosphonopropene) with 
units of the formula: 
##STR2## 
A preferred phosphonic acid-containing AEA for use herein is poly (beta 
styrene phosphonic acid) containing units of the formula: 
##STR3## 
wherein Ph is phenyl, the phosphonic delivery-enhancing group and the 
phenyl retention-enhancing group being bonded on vicinal carbon atoms in 
the chain, or a copolymer of beta styrene phosphonic acid with vinyl 
phosphonyl chloride having the units of the foregoing formula III 
alternating or in random association with units of formula I above, or 
poly (alpha styrene phosphonic acid) containing units of the formula: 
##STR4## 
in which the delivery--and retention--enhancing groups are geminally 
bonded to the chain. 
These styrene phosphonic acid polymers and their copolymers with other 
inert ethylenically unsaturated monomers generally have molecular weights 
in the range of about 2,000 to about 30,000, preferably about 2,500 to 
about 10,000, and are, with their methods of preparation disclosed and 
claimed in concurrently filed application Ser. No. 398,606, which 
disclosure is incorporated here. Such "inert" monomers do not 
significantly interfere with the intended function of any copolymer 
employed as an AEA herein. 
Other phosphonic-containing polymers include, for example, phosphonated 
ethylene having units of the formula. 
EQU --[CH.sub.2 ].sub.14 CHPO.sub.3 H.sub.2 ].sub.Y1 -- 
where n may for example be an integer or have a value giving the polymer a 
molecular weight of about 3,000; and sodium poly [butene-4, 
4-diphosphonste) having units of the formula: 
##STR5## 
poly (allyl bis (phosphonoethyl) amine) having units of the formula: 
##STR6## 
Other phosphonated polymers, for example poly (allyl phosphono acetate), 
phosphonated polymethacrylate, etc. and the geminal diphosphonate polymers 
disclosed in EP Publication 0321233 may be employed herein as AEA's, 
provided of course that they contain or are modified to contain the 
above-defined organic retention-enhancing groups. 
Although not used in the present invention to coact with polyphosphate 
anticalculus agent, synthetic anionic polymeric polycarboxylate having a 
molecular weight of about 1,000 to about 1,000,000, preferably about 
30,000 to about 500,000, has been used as an inhibitor of alkaline 
phosphatase enzyme in optimizing anticalculus effectiveness of linear 
molecularly dehydrated polyphosphate salts, as disclosed in U.S. Pat. No. 
4,627,977 to Gaffar et al. Indeed, in published British Patent Publication 
22 00551, the polymeric polycarboxylate is disclosed as an optional 
ingredient in oral compositions containing linear molecularly dehydrated 
polyphosphate salts and substantially water-insoluble noncationic 
antibacterial agent. It is further observed, in the context of the present 
invention that such polycarboxylate is markedly effective to enhance 
delivery and retention of the noncationic antibacterial, antiplaque agent 
to dental surfaces when another ingredient with which the polymeric 
polycarboxylate would coact (that is, molecularly dehydrated 
polyphosphate) is absent; for instance, when the ingredient with which the 
polymeric polycarboxylate coacts is especially the noncationic 
antibacterial agent. 
Synthetic anionic polymeric polycarboxylates and their complexes with 
various cationic germicides, zinc and magnesium have been previously 
disclosed as anticalculus agents per se in, for example U.S. Pat. No. 
3,429,963 to Shedlovsky; U.S. Pat. No. 4,152,420 to Gaffar; U.S. Pat. No. 
3,956,480 to Dichter et al; U.S. Pat. No. 4,138,477 to Gaffar; and U.S. 
Pat. No. 4,183,914 to Gaffar et al. It is to be understood that the 
synthetic anionic polymeric polycarboxylates so disclosed in these several 
patents when containing or modified to contain the above-defined 
retention-enhanclng groups are operative as AFA's in the compositions and 
methods of this invention and such disclosures are to that extent 
incorporated herein by reference thereto. 
These synthetic anionic polymeric polycarboxylates are often employed in 
the form of their free acids or preferably partially or more preferably 
fully neutralized water soluble or water-swellable (hydratable, 
gel-forming) alkali metal (e.g. potassium and preferably solids) or 
ammonium salts. Preferred are 1:4 to 4:1 copolymers of maleic anhydride or 
acid with another polymerizable ethylenically unsaturated monomer, 
preferably methyl vinyl ether (maleic anhydride) having a molecular weight 
(M.W.) of about 30,000 to about 1,000,000, most preferably about 30,000 to 
about 500,000. These copolymers are available for example as Gantrez, e.g. 
AN 139 (M.W. 500,000), A.N. 119 (M.W. 250,000); and preferably S.97 
Pharmaceutical Grade (M.W. 70,000), of GAF Corporation. 
Other AEA-operative polymeric polycarboxylates containing or modified to 
contain retention-enhancing groups include those disclosed in U.S. Pat. 
No. 3,956,480 referred to above, such as the 1:1 copolymers of maleic 
anhydride with ethyl acrylate, hydroxyethyl meihacrylaie, 
N-vinyl-2-pyrollidone, or ethylene, the latter being available for example 
as Monsanto EMA No. 1103 M.W. 10,000 and EMA Grade 61, and 1:1 copolymers 
of acrylic acid with methyl or hydroxyethyl methacrylate, methyl or ethyl 
acrylate, isobutyl, isobutyl vinyl ether or N-vinyl-2-pyrrolidone. 
Additional operative polymeric polycarboxylates disclosed in above referred 
to U.S. Pat. Nos. 4,138,477 and 4,183,914 containing or modified to 
contain retention-enhancing groups, include copolymers of maleic anhydride 
with styrene, isobutylene or ethyl vinyl ether, polyacrylic, polyitaconic 
and polymaleic acids, and sulfoacrylic oligomers of M.W. as low as 1,000, 
available as Uniroyal ND-2. 
Suitable generally are retention-enhancing group-containing polymerized 
olefinically o ethylenically unsaturated carboxylic acids containing an 
activated carbon-to-carbon olefinic double bond which readily functions in 
polymerization because of its presence in the monomer molecule either in 
the alpha-beta position with respect to a carboxyl group or a part of a 
terminal methylene grouping. Illustrative of such acids are acrylic, 
methacrylic, ethacrylic, alpha-chloroacrylic, crontonic, beta-acryloxy 
propionic, sorbic, alpha-chlorsorbic, cinnamic, beta-styrylacrylic, 
muconic, itaconic, citraconic, mesaconic, glutaconic, aconitic, 
alpha-phenylacrylic, 2-benzyl acrylic, 2-cyclohexylacrylic, angelic, 
umbellic, fumaric, maleic acids and anhydrides. Other different olefinic 
monomer copolymerizable with such carboxylic monomers includ vinylacetate, 
vinyl chloride, dimethyl maleate and the like. Copolymers ordinarily 
contain sufficient carboxylic salt groups for water-solubility. 
Also useful herein are so-called carboxyvinyl polymers disclosed as 
toothpaste components in U.S. Pat. No. 3,980,767 to Chown et al; U.S. Pat. 
No. 3,935,306 Roberts et al; U.S. Pat. No. 3,919,409 to Perla et al; U.S. 
Pat. No. 3,911,904 to Harrison, and U.S. Pat. No. 3,711,604 to Colodney et 
al. They are commercially available for example under the trademarks 
Carbopol 934, 940 and 941 of B.F. Goodrich, these products consisting 
essentially of a colloidally water-soluble polymer of polyacrylic acid 
crosslinked with from about 0.75% to about 2.0% of polyallyl sucrose or 
polyallyl pentaerythritol as cross linking agent, the cross-linked 
structures and linkages in these and other cross-linked polymeric AEA's 
providing the desired retention enhancement by hydrophobicity when 
adequate, and/or physical entrapment of the antibacterial agent. 
Polycarbophil, being polyacrylic cross-linked with less than 0.1% divinyl 
glycol, the lower proportion, molecular weight, and/or hydrophobicity of 
this cross-linking agent tending to provide decreased or no retention 
enhancement 2,5-dimethyl-1,5-hexadiane, exemplifies a more effective 
retention-enhancing cross-linking agent. 
The synthetic anionic polymeric polycarboxylate component is most often a 
hydrocarbon with option halogen and 0-containing substituents and linkages 
as present in for example ester, ether and OH groups, and is employed in 
the instant compositions in approximate weight amounts of 0.05 to 4%, 
preferably 0.05 to 3%, more preferably 0.1 to 2%. 
The AEA may also comprise natural anionic polymeric polycarboxylates 
containing retention-enhancing groups. Carboxymethyl cellulose and other 
binding agents gums and film-formers devoid of the above-defined 
delivery-enhancing and/or retention-enhancing groups are ineffective as 
AEA's. 
As illustrative of AEA's containing phosphinic acid and/or sulfonic acid 
delivery enhancing groups, there may be mentioned polymers and copolymers 
containing units or moieties derived from the polymerization of vinyl or 
allyl phosphinic and/or sulfonic acids substituted as needed on the 1 or 2 
(or 3) carbon atom by an organic retention-enhancing group, for example 
having the formula --(X).sub.n --R defined above. Mixtures of these 
monomers may be employed, and copolymers thereof with one or more inert 
polymerizable thylenically unsaturated monomers such as those described 
above with respect to the operative synthetic anionic polymeric 
polycarboxylates. As will be noted, in these and other polymeric AEA's 
operative herein, usually only one acidic delivery-enhancing group is 
bonded to any given carbon or other atom in the polymer backbone or branch 
thereon. Polysiloxanes containing or modified to contain pendant 
delivery-enhancing groups and retention enhancing groups may also be 
employed as AEA's herein. Also effective as AEA's herein are ionomers 
containing or modified to contain delivery-and retention-enhancing groups. 
Ionomers are described on pages 546-573 of the Kirk-Othmer Encyclopedia of 
Chemical Technology, third edition, Supplement Volume, John Wiley & Sons, 
Inc., copywright 1984, which 
description is incorporated herein by reference. Also effective as AEA's 
herein, provided they contain or are modified to contain 
retention-enhancing groups, are polyesters, polyurethanes and synthetic 
and natural polyamides including proteins and proteinaceous materials such 
as collagen, poly (argenine) and other polymerized amino acids. 
Without being bound to a theory, it is believed that the AEA, especially 
polymeric AEA is most often and desirably an anionic film forming material 
and is thought to attach to tooth surfaces and form a continuous film over 
the surfaces, thereby preventing bacterial attachment to tooth surfaces. 
It is possible that the noncationic antibacterial agent forms a complex or 
other form of association with the AEA, thus forming a film of a complex 
or the like over tooth surfaces. The enhanced delivery and film forming 
property of the AEA and the enhanced delivery and retention of the 
antibacterial agent on tooth surfaces due to the AEA appears to make tooth 
surfaces unfavorable for bacterial accumulation particularly since the 
direct bacteriostatic action of the antibacterial agent controls bacterial 
growth. Therefore, through the combination of three modes of actions: 1) 
enhanced delivery, 2) long retention time on tooth surfaces, and 3) 
prevention of bacterial attachment to tooth surfaces, the oral composition 
is made efficacious for reducing plaque. Similar effectiveness is attained 
on soft oral tissue at or near the gum line. 
In aforementioned application Ser. No. 398,606 filed on even date, titled 
"Antibacterial Antiplaque Oral Composition" wherein the dentifrices 
thereof contain about 5-30% by weight of a siliceous polishing agent, a 
material which solubilizes the noncationic antibacterial agent to render 
it effective in delivery to soft oral tissues at the gum line is employed. 
In the present invention, wherein about 30-75% by weight of a dentally 
acceptable water-insoluble polishing agent is present, it is found that 
the solubilizing material is not required; but is rather optional. 
In the oral preparation dentifrice, an orally acceptable vehicle including 
a water-phase with humectant is present. The humectant is preferably 
glycerine and/or sorbitol. Water is present typically in amount of about 
15-35% or 40% by weight and glycerine and/or sorbitol typically total 
about 20-75% by weight of the oral preparation dentifrice, more typically 
about 25-60%. Reference hereto to sorbitol refers to the material 
typically as available commercially in 70% aqueous solutions. The optional 
ingredients which assist solubilization of the antibacterial agent in 
saliva are typically incorporated in the water-humectant phase in amount 
of about 0.5-20% by weight. These optional solubilizing agents include 
humectant polyols such propylene glycol, dipropylene glycol and hexylene 
glycol, cellosolves such as methyl cellosolve and ethyl cellosolve, 
vegetable oils and waxes containing at least about 12 carbons in a 
straight chain such as olive oil, castor oil and petrolatum and esters 
such as amyl acetate, ethyl acetate and benzyl benzoate. As used herein, 
"propylene:glycol" includes 1,2-propylene glycol and 1,3-propylene glycol. 
Significant amounts of polyethylene glycol particularly of molecular 
weight of 600 or more should be avoided since polythylene glycol 
effectively inhibits the antibacterial activity of the noncationic 
antibacterial agent. For instance, polyethylene glycol (PEG) 600 when 
present with tricolosan in a weight ratio oi 25 triclosan:1 PEG 600 can 
reduce the antibacterial activity of triclosan by a factor of about 16 
from that prevailing in the absence of the polyethylene glycol. 
The pH of such oral preparation dentifrice of the invention is generally in 
the range of about 4.5 to about 9 or 10 and preferably about 6.5 to about 
7.5. It is noteworthy that the compositions of the invention may be 
applied orally at a pH below 5 without substantially decalcifying or 
otherwise damaging dental enamel. The pH can be controlled with acid (e.g. 
citric acid or benzoic acid) or base (e.g. sodium hydroxide) or buffered 
(as with sodium citrate, benzoate, carbonate, or bicarbonate, disodium 
hydrogen phosphate, sodium dihydrogen phosphate, etc.).

In this invention, the oral composition dentifrice may be substantially 
pasty in character, such as a tooth paste (dental cream), although when 
siliceous polishing agent is employed (which is not generally the case, 
since such material is typically not employed in amount above about 30% by 
weight) it can be gel in character. The vehicle of the oral composition 
dentifrice contains dentally acceptable polishing material, examples of 
which polishing materials are waier-insoluble sodium metaphosphate, 
potassium metaphosphate, tricalcium phosphate, dihydrated dicalcians 
phosphate, anhydrous dicalcium phosphate, calcium pyrophosphate, magnesium 
orthophosphate, trimagnesium phosphate, calcium carbonate, aluminum 
silicate, hydrated alumina, silica, bentonite, and mixtures thereof with 
each other or with hard polishing materials such as calcined alumina and 
zirconium silicate, material including the particulate thermosetting 
resins described in U.S. Pat. No. 3,070,510 issued Dec. 15, 1962, such as 
melamine-phenolic, and urea-formaldehydes, and cross-linked polyepoxides 
and polyesters. Preferred polishing materials include insoluble sodium 
metaphosphates, dicalcium phosphate and hydrated alumina. 
Many of the so-called "water-insoluble" polishing materials are anionic in 
character and also include small amounts of soluble material. Thus, 
insoluble sodium metaphosphate may be formed in any suitable manner as 
illustrated by Thorpe's Dictionary of Applied Chemistry, Volume 9, 4th 
Edition, pp. 510-511. The forms of insoluble sodium metaphosphate known as 
Madrell's salt and Kurrol's salt are further examples of suitable 
materials. These metaphosphate salts exhibit only a minute solubility in 
water, and therefore are commonly referred to as insoluble metaphosphates 
(IMP). There ls present therein a minor amount of soluble phosphate 
material as impurities, usually a few percent such as up to 4% by weight. 
The amount of soluble phosphate material, which is believed to include a 
soluble sodium trimetaphosphate in the case of insoluble metaphosphate, 
may be reduced or eliminated by washing with water if desired. The 
insoluble alkali metal metaphosphate is typically employed in powder form 
of a particle size such that no more than 1% of the material is larger 
than 37 microns. 
Hydrated alumina is an example of a polishing material which is essentially 
nonionic in nature. Typically, it is small in particle size, i.e., at 
least about 85% of the particles are smaller than 20 microns and is such 
as that classified as gibbsite (alpha alumina trihydrate) and normally 
represented chemically as Al.sub.2 O.sub.3.3H.sub.2 O or Al(OH).sub.3. The 
average particle size of gibbsite is generally about 6 to 9 microns. A 
typical grade has the following size distribution: 
______________________________________ 
Micron 
Percent 
______________________________________ 
&lt;30 94-99 
&lt;20 85-93 
&lt;10 56-67 
&lt;5 28-40 
______________________________________ 
The polishing material is generally present in the cream, paste or gel 
compositions in weight amounts of about 30% to about 75%. 
Toothpastes or dental cream typically contain a natural or synthetic 
thickener or gelling agent in proportions of about 0.1 to about 10%, 
preferably about 0.5 to about 5%. A suitable thickener is synthetic 
hectorite, a synthetic colloidal magnesium alkali metal silicate complex 
clay available for example as Laponite (e.g. CP, SP 2002, D) marketed by 
Laporte Industries Limited. Laponite D analysis shows, approximately by 
weight, 58.00% SiO.sub.2, 25.40% MgO, 3.05% Na.sub.2 O, 0.98% Li.sub.2 0), 
and some water and trace metals. Its true specific gravity is 2.53 and it 
has an apparent bulk density (g./ml. at 8% moisture) of 1.0. 
Other suitable thickeners or gelling agents include Irish moss, 
iota-carrageenan, gum tragacanth, starch, polyvinylpyrrolidone, 
hydroxyethpropyl-cellulose, hydroxybutyl methyl cellulose, hydroxypropyl 
methyl cellulose, hydroxyethyl cellulose (e.g. available as Natrosol) and 
sodium carboxymethyl cellulose. 
Without being bound to a theory whereby the advantages of this invention 
are achieved, it is believed that an aqueous, humectant vehicle is 
normally solubilized in the surfactant micelles in the mobile, e.g. 
liquid, phase (that is, not including gelling agent and polishing agent) 
of a dentrifice formula. The mobile phase solution of dentifrice during 
use can become diluted with saliva and a portion of the antibacterial 
agent, e.g. triclosan, could precipitate out. However, when the amount of 
polishing agent is 30% by weight or more oi the oral composition 
dentifrice, the amount of triclosan soluble in the mobile phase is 
sufficient to provide substantial antiplaque effect on soft oral tissues 
as well as on dental surfaces. This effect can be increased, if desired, 
if a solubilizing material compatible with the antibacterial agent which 
increases its solubility in saliva is present. In this regard it is noted 
that the solubilizing agent propylene glycol is widely used in drug 
delivery systems, for instance, in European Patent Publication 0271,332 
for its strong interaction with biological membranes. It is expected that 
triclosan is partitioned from aqueous environment into propylene glycol 
and surfactant emulsions during use and further that propylene glycol in 
bulk phase allows greater probability of triclosan emergence out of 
surfactant micelles, thereby rendering triclosan more completely available 
for delivery into bacterial and soft surfaces as well as onto tooth 
surfaces. Similar remarks apply to other water insoluble noncationic 
antibacterial agents herein described. 
The oral composition dentifrice may also contain an anticaries amount of a 
fluoride ion source sufficient to supply about 25 ppm to 5000 ppm of 
fluoride ions. 
The sources of fluoride ions, or fluoride-providing component are well 
known in the art as anti-caries agents. These compounds may be slightly 
soluble in water or may be fully water-soluble. They are characterized by 
their ability to release fluoride ions in water and by substantial freedom 
from undesired reaction with other compounds of the oral preparation. 
Among these materials are inorganic fluoride salts, such as soluble alkali 
metal, alkaline earth metal salts, for example sodium fluoride, potassium 
fluoride, ammonium fluoride, calcium fluoride, a copper fluoride such as 
cuprous fluoride, zinc fluoride, barium fluoride, sodium fluorosilicate, 
ammonium fluorosilicate, sodium fluorozirconate, ammonium fluorozirconate, 
sodium monofluorphosphate, aluminum mono-and di-fluorophosphate, and 
fluorinated sodium calcium pyrophosphate. Alkali metal and tin fluorides, 
such as sodium and stannous fluorides, sodium monofluorophosphate (MFP) 
and mixtures thereof, are preferred. 
The amount of fluorine-providing compound is dependent to some extent upon 
the type of compound, its solubility, and the type of oral preparation, 
but it must be a non-toxic amount, generally about 0.0005 to about 3.0% in 
the preparation. In a dentifrice preparation, an amount of such compound 
which releases up to about 5,000 ppm of F ion by weight of the preparation 
is considered satisfactory. Any suitable minimum amount of such compound 
may be used, but it is preferable to employ sufficient compound to release 
about 300 to 2,000 ppm, more preferably about 800 to about 1,500 ppm of 
fluoride ion. 
Typically, in the cases of alkali metal fluorides, this component is 
present in an amount up to about 2% by weight, based on the weight of the 
preparation, and preferably in the range of about 0.05% to 1%. In the case 
of sodium monofluorophosphate, the compound may be the present in an 
amount of about 0.1-3%, more typically about 0.76%. 
It will be understood that, as is conventional, the oral preparations are 
to be sold or otherwise distributed in suitable labelled packages. Thus a 
toothpaste or cream will usually be in a collapsible tube typically 
aluminum, lined lead or plastic, or other squeeze, pump or pressurized 
dispenser for metering out the contents, having a label describing it, in 
substance, as a toothpaste, dental cream or the like. 
Organic surface-active agents are used in the compositions of the present 
invention to achieve increased prophylactic action. Moreover, they assist 
in achieving thorough and complete dispersion of the anticalculus agent 
and antiplaque agent throughout the oral cavity, and render the instant 
compositions more cosmetically acceptable. Indeed, at least one of 
surface-active agent or flavoring oil is present to effect desired 
solubilization of the antibacterial agent. The organic surface-active 
material is preferably anionic, nonionic or ampholytic in nature, and it 
is preferred to employ as the surface-active agent a detersive material 
which imparts to the composition detersive and foaming properties. 
Suitable examples of anionic surfactants are water-soluble salts of higher 
fatty acid monoglyceride monosulfates, such as the sodium salt of the 
monosulfated monoglyceride of hydrogenated coconut oil fatty acids, higher 
alkyl sulfates such as sodium lauryl sulfate, alkyl aryl sulfonates such 
as sodium dodecyl benzene sulfonate, higher alkyl sulfoacetates, higher 
fatty acid esters of 1,2-dihydroxy propane sulfonate, and the 
substantially saturated higher aliphatic acyl amides of lower aliphatic 
amino carboxylic acid compounds, such as those having 12 to 16 carbons in 
the fatty acid, alkyl or acyl radicals, and the like. Examples of the last 
mentioned amides are N-lauroyl sarcosine, and the sodium, potassium, and 
ethanolamine salts of N-lauroyl, N-myristoyl, or N-palmitoyl sarcosine 
which should be substantially free from soap or similar higher fatty acid 
material. The use of these sarcosinate compounds in the oral compositions 
of the present invention is particularly advantageous since these 
materials exhibit a prolonged a marked effect in the inhibition of acid 
formation in the oral cavity due to carbohydrates breakdown in addition to 
exerting some reduction in the solubility of tooth enamel in acid 
solutions. Examples of water-soluble nonionic surfactants are condensation 
products of ethylene oxide with various reactive hydrogen-containing 
compounds reactive therewith having long hydrophobic chains (e.g. 
aliphatic chains of about 12 to 20 carbon atoms), which condensation 
products ("ethoxamers") contain hydrophilic polyoxyethylene moieties, such 
as condensation products of poly(ethylene oxide) with fatty acids, fatty 
alcohols, fatty amides, polyhydric alcohols (e.g. sorbitan monostearate) 
and polypropyleneoxide (e.g. Pluronic materials). 
Surface active agent is typically present in amount of about 0.5-5% by 
weight, preferably about 1-2.5%. As indicated, surface active agent is 
believed to assist in the dissolving of the noncationic antibacterial 
agents. 
Various other materials may be incorporated in the oral preparations of 
this invention such as whitening agents, preservatives, silicones, 
chlorophyll compounds and/or ammoniated material such as urea, diammonium 
phosphate, and mixtures thereof. These adjuvants, where present, are 
incorporated in the preparations in amounts which do not substantially 
adversely affect the properties and characteristics desired. Significant 
amounts of zinc, magnesium and other metal salts and materials, generally 
soluble, which would complex with active components of the instant 
invention are to be avoided. 
Any suitable flavoring or sweetening material may also be employed. 
Examples of suitable flavoring constituents are flavoring oils, e.g. oil 
of spearmint, peppermint, wintergreen, sassafras, clove, sage, eucalyptus, 
marjoram, cinnamon, lemon, and orange, and methyl salicylate. Suitable 
sweetening agents include sucrose, lactose, maltose, sorbitol, xylitol, 
sodium cyclamate, perillartine, AMP (aspartyl phenyl alanine, methyl 
ester), saccharine and the like. Suitably, flavor and sweetening agents 
each or together comprise from about 0.1% to 5% more of the preparation. 
Moreover, flavor oil is believed to aid the dissolving of the 
antibacterial agent together with or even in the absence of surface-active 
agent. 
In the preferred practice of this invention an oral composition containing 
the composition of the present invention is preferably applied regularly 
to dental enamel, such as every day or every second or third day or 
preferably from 1 to 3 times daily, at a pH of about 4.5 to about 9, 
generally about 5.5 to about 8, preferably about 6 to 8, for at least 2 
weeks up to 8 weeks or more up to lifetime. 
The compositions of this invention can be incorporated in lozenges, or in 
chewing gum or other products, e.g. by stirring into a warm gum base or 
coating the outer surface of a gum base, illustrative of which may be 
mentioned jelutong, rubber latex, vinylite resins, etc., desirably with 
conventional plasticizers of softeners, sugar or other sweeteners or 
carbohydrates such as glucose, sorbitol and the like. 
The following examples are further illustrative of the nature of the 
present invention, but it is understood that the invention is not limited 
thereto. All amounts and proportions referred to herein and in the 
appended claims are by weight, unless otherwise indicated. 
EXAMPLE 1 
The following dentifrice is prepared: 
______________________________________ 
Parts 
A B C 
______________________________________ 
Alpha Alumina Trihydrate 
48.00 48.00 48.00 
Propylene Glycol -- 0.50 0.50 
Sorbitol (70%) 21.70 21.70 21.70 
Gantrez S-97 (13% solution) 
15.00 15.00 -- 
Gantrez S-97 (powder) 
-- -- 2.00 
Sodium Lauryl Sulfate 
2.00 2.13 2.13 
Sodium Saccharine 0.30 0.30 0.30 
Sodium Hyroxide (50%) 
1.20 1.20 1.20 
Flavor Oil 0.95 0.95 0.95 
Irish Moss 1.00 -- -- 
Sodium carboxymethyl celluose 
-- 1.00 1.00 
Sodium monofluorophosphate 
0.76 0.76 0.76 
Titanium Dioxide -- 0.50 0.50 
Triclosan 0.30 0.30 0.30 
Water Q.S. to Q.S. to Q.S. to 
100.00 100.00 100.00 
______________________________________ 
The foregoing dentifrices deliver triclosan to the teeth and soft tissue 
areas of the gums substantially more effectively than corresponding 
dentifrices in which the Gantrez polycarboxylate is absent. 
EXAMPLE 2 
The following dentifrices are prepared: 
______________________________________ 
Parts 
______________________________________ 
Glycerine 22.00 10.00 
Sorbitol (70%) -- 17.00 
Sodium Carboxymethyl cellulose 
1.00 1.00 
Gantrez S-97 2.00 2.00 
Sodium Saccharin 0.20 0.20 
Sodium Benzoate 0.50 0.50 
Sodium Monofluorophosphate 
0.76 0.76 
Dicalcium Phosphate Dihydrate 
48.76 48.76 
Triclosan 0.30 0.30 
Sodium Lauryl Sulfate 
1.20 1.20 
Flavor Oil 0.89 0.89 
Water Q.S. to 100.00 
Q.S. to 100.00 
______________________________________ 
The foregoing dentrifices deliver triclosan to saliva coated hydroxyapatite 
disk more effectively than corresponding dentifrices in which the Gantrez 
polycarboxylate is absent. 
EXAMPLE 3 
The following antiplaque dentifrice is prepared: 
______________________________________ 
Parts 
______________________________________ 
Glycerine 15.00 
Propylene Glycol 2.00 
Sodium Carboxymethyl cellulose 
1.50 
Water 24.93 
Vinyl Methyl Ether/Maleic Anhydride copolymer 
4.76 
(42% solution) 
Sodium Monofluorophosphate 0.76 
Sodium Saccharin 0.30 
Insoluble Sodium Metaphosphate 
47.00 
Titanium Dioxide 0.50 
Sodium Lauryl Sulfate 2.00 
Triclosan 0.95 
Flavor Oil 0.95 
______________________________________ 
In the foregoing Examples improved results are also achievable when 
triclosan is replaced with each of phenol, 2,2'-methylene bis 
(4-chloro6-Bromophenol), eugenol and thymol, and/or when Gantrez is 
replaced by other AEA's such as Carbopols (e.g. 934), or styrene 
phosphonic acid polymers having molecular weights within the range of 
about 3,000 to 10,000 such as poly (beta-styrenephosphonic acid), and poly 
(alpha-styrenephosphonic acid), or sulfoacrylic oligomers, or a 1:1 
copolymer of maleic anhydridge with ethyl acrylate. 
EXAMPLE 4 
Dentifrice Mobile Phases Containing Triclosan 
______________________________________ 
Dentifrice Mobile Phases Containing Triclosan 
Composition, % w/w 
Components A B 
______________________________________ 
Sorbitol (70%) 53.33 40.00 
Water 40.48 39.15 
Gantrez S (15%) -- 13.33 
NaOH (50%) 1.33 
Sodium Pyrophosphate 
-- -- 
Potassium Pyrophosphate 
-- -- 
Saccharin 0.40 0.40 
Sodium Fluoride 0.32 0.32 
Flavor Oil 1.47 1.47 
Sodium Lauryl Sulfate 
3.33 3.33 
Triclosan 0.67 0.67 
______________________________________ 
The Concentration of the above components are 1.33% dentifrice level to 
reflect 25% of abrasive which may be needed to make a complete dentrifice. 
The above mobile phases of the indicated dentifrice formulations are tested 
fortriclosan uptake on saliva coated HA disks following the standard 
procedure described in assignee's said concurrently filed Ser. No. 
398,606. Results are shown in Table I below. 
TABLE I 
______________________________________ 
Uptake of triclosan by Saliva Coated Hydroxyapatite (HA) Disks 
from Diluted and Undiluted Dentifrice Mobile Phases. 
A B 
______________________________________ 
% Triclosan 0.67 0.67 
Ionic Strength (M/L) 
0.375 -- 
(calculated) 
pH 8.7 7.6 
Triclosan Uptake (ug/disk) 
55 122 
Undiluted 
______________________________________ 
The above results show a greater then two fold increase in triclosan uptake 
achieved with the B formulation containing Gantrez relative to the A 
formulation without the Gantrez. 
EXAMPLE 5 
______________________________________ 
Concentration and Uptake of Triclosan by HA from 
Supernatant of 1:1 Dentifrice/Water Slurries. 
Dentifrice Containing 
Triclosan (ug/ml) 
Triclosan 
0.5% Triclosan, 2.5% 
in Supernatant 
Uptake 
Sodium, and Lauryl Sulfate 
of 1:1 Slurry 
pg/disk 
______________________________________ 
25% Hydrated Silica + 
1,650 52 
1.5% Gantrez S-97 
50% Alumina, + 1,905 74 
1.5% Gantrez S-97 
______________________________________ 
Supernatents of 1:1 Dentifrice/Water slurries of the above dentifrices are 
tested for concentration of the triclosan in the supernatant and for 
triclosan uptake on saliva coated HA disks. The results indicate that 
using 50% alumina abrasive increases the triclosan substantially under low 
1:1 dilution conditions (from 1,650 to 1,905), resulting in a substantial 
increase in the triclosan uptake (from 52 to 74). 
This invention has been described with respect to certain preferred 
embodiments and it will be understood that modifications and variations 
thereof obvious to those skilled in the art are to be included within the 
purview of this application and the scope of the appended claims.