Oral hygiene compositions for preventing the formation of oral biofilms and process for preparing the same

A process for preparing a styrene-maleic acid copolymer or salt thereof comprising heating a high minimum biofilm inhibitory concentration (styrene-maleic anhydride copolymer at a temperature of 100° C. to 350° C. for 5 minutes to 5 hours, wherein the minimum biofilm inhibitory concentration of the high minimum biofilm inhibitory concentration styrene-maleic anhydride copolymer ranges from 11 ppm to 8000 ppm, wherein the styrene-maleic acid copolymer or salt thereof has the structure:

• wherein a=50-80 mole %, b=50-20 mole %, and a+b=100 mole %,
• X and Y are independently O or NH,
• and R1 and R2 are independently a C1-C18 alkyl or substituted alkyl group, a C6-C22 substituted or unsubstituted aryl, alkaryl or arylalkyl group, a substituted carboxymethyl group or salt thereof having the structure CH(R3)CO2H, or a poly(ethylenoxy), poly(propylenoxy) or poly(ethylenoxy-propylenoxy) group having the structure (CH(R4)CH(R5)O)cR6, or mixtures thereof,
• wherein R3=H, methyl, hydroxymethyl, 1-hydroxyethyl, isopropyl, isobutyl, sec-butyl, benzyl, para-hydroxybenzyl, 1H-indol-3-ylmethyl, carboxymethyl, 2-carboxyethyl, carbamoylmethyl, 2-carbamoylethyl, 4-aminobutyl, 3-guanidinopropyl or 1H-imidazol-4-ylmethyl or mixtures thereof,
• c=2-24,
• R4=R5=H, R4=H and R5-methyl, or R4=methyl and R5=H,
• and R6 is H or a substituted or unsubstituted C1-C18 alkyl, aryl, alkaryl or arylalkyl group, and said styrene maleic acid copolymer or salt thereof has a polydispersity ranging from 2 to 14 and a minimum biofilm inhibitory concentration ranging from 0.001 ppm to 1000 ppm, provided that R1 and R2 are not both a C1-alkyl or substituted C1-alkyl group when X and Y are O.

A method of reducing deposition of an oral biofilm on teeth or soft tissue comprising applying to an oral cavity an oral hygiene composition comprising:

• (i) a styrene-maleic acid copolymer or salt thereof having the structure:
• wherein a=50-80 mole %, b=50-20 mole %, and a+b=100 mole %, or
• (ii) a styrene-maleic acid terpolymer or salt thereof having the structure:
• wherein d=0.5-20 mole %, e=80.5-40 mole %, f=16-40 mole %, and d+e+f=100 mole %;
• wherein X and Y are independently O or NH,
• R1 and R2 are independently a C1-C18 alkyl or substituted alkyl group, a C6-C22 substituted or unsubstituted aryl, alkaryl or arylalkyl group, a substituted carboxymethyl group or salt thereof having the structure CH(R3)CO2H, or a poly(ethylenoxy), poly(propylenoxy) or poly(ethylenoxy-propylenoxy) group having the structure (CH(R4)CH(R5)O)cR6, or mixtures thereof,
• wherein R3=H, methyl, hydroxymethyl, 1-hydroxyethyl, isopropyl, isobutyl, sec-butyl, benzyl, para-hydroxybenzyl, 1H-indol-3-ylmethyl, carboxymethyl, 2-carboxyethyl, carbamoylmethyl, 2-carbamoylethyl, 4-aminobutyl, 3-guanidinopropyl or 1H-imidazol-4-ylmethyl or mixtures thereof,
• c=2-24,
• R4=R5=H, R4=H and R5=methyl, or R4=methyl and R5=H,
• and R6 is H or a substituted or unsubstituted C1-C18 alkyl, aryl, alkaryl or arylalkyl group, R7=H or methyl,
• Z=P(O)(OH)2 or a salt thereof, OP(O)(OH)2 or a salt thereof, C(O)NHC(CH3)2CH2SO3H or a salt thereof, OR8 or C(O)QR9,
• wherein R8 is a C1-C18 alkyl or substituted alkyl group, a C6-C22 substituted or unsubstituted aryl, alkaryl or arylalkyl group, or a poly(ethylenoxy), poly(propylenoxy) or poly(ethylenoxy-propylenoxy) group having the structure (CH(R4)CH(R5)O)cR6,
• wherein c=2-24,
• R4=R5=H, R4=H and R5=methyl, or R4=methyl and R5=H, and R6 is H or a substituted or unsubstituted C1-C18 alkyl, aryl, alkaryl or arylalkyl group,
• Q=O or NH,
• and R9 is a C1-C18 alkyl or substituted alkyl group, a C6-C22 substituted or unsubstituted aryl, alkaryl or arylalkyl group, or a poly(ethylenoxy), poly(propylenoxy) or poly(ethylenoxy-propylenoxy) group having the structure (CH(R4)CH(R5)O)cR6,
• wherein c=2-24,
• R4=R5=H, R4=H and R5=methyl, or R4=methyl and R5=H,
• and R6 is H or a substituted or unsubstituted C1-C18 alkyl, aryl, alkaryl or arylalkyl group, and
• the copolymer or terpolymer has a polydispersity ranging from 2 to 14, a minimum biofilm inhibitory concentration ranging from 0.001 ppm to 1000 ppm, provided that R1 and R2 are not both a C1-alkyl or substituted C1-alkyl group when X and Y are O.

An oral hygiene composition comprising a styrene-maleic acid copolymer or salt thereof having the structure:

• wherein a=50-55 mole %, b=50-45 mole %, and a+b=100 mole %,
• X and Y are independently O or NH,
• and R1 and R2 are independently a C1-C18 alkyl or substituted alkyl group, a C6-C22 substituted or unsubstituted aryl, alkaryl or arylalkyl group, a substituted carboxymethyl group or salt thereof having the structure CH(R3)CO2H, or a poly(ethylenoxy), poly(propylenoxy) or poly(ethylenoxy-propylenoxy) group having the structure (CH(R4)CH(R5)O)cR6, or mixtures thereof,
• wherein R3=H, methyl, hydroxymethyl, 1-hydroxyethyl, isopropyl, isobutyl, sec-butyl, benzyl, para-hydroxybenzyl, 1H-indol-3-ylmethyl, carboxymethyl, 2-carboxyethyl, carbamoylmethyl, 2-carbamoylethyl, 4-aminobutyl, 3-guanidinopropyl or 1H-imidazol-4-ylmethyl or mixtures thereof,
• c=2-24,
• R4=R5=H, R4=H and R5=methyl, or R4-methyl and R5=H,
• and R6 is H or a substituted or unsubstituted C1-C18 alkyl, aryl, alkaryl or arylalkyl group, wherein said copolymer or salt thereof has
• (a) a weight average molecular weight ranging from 100,000 to 2,000,000
• (b) a polydispersity ranging from 2 to 10 and
• (c) a minimum biofilm inhibitory concentration ranging from 0.001 ppm to 1000 ppm, provided that R1 and R2 are not both a C1-alkyl or substituted C1-alkyl group when X and Y are O.