Water-in-oil emulsions with anionic groups, compositions, and methods

A water-in-oil emulsion comprising:

• an oil phase;
• a water phase;
• and a vinyl polymer having a pKa of less than 4 comprising the reaction product of monomers comprising:
• about 60 wt-% to about 95 wt-% of at least one monoethylenically unsaturated alkyl (meth)acrylic monomer having the formula:
• 9
• wherein:
• R1 is hydrogen or methyl;
• and
• R2 is a linear, branched, or cyclic alkyl group optionally including one or more heteroatoms;
• and
• about 5 wt-% to about 40 wt-% of at least one low pKa acid-containing monomer, or salt thereof, having the formula:
• 10
• wherein:
• X is O or NR5;
• R3 and R5 are each independently hydrogen or methyl;
• R4 is a linear, branched, or cyclic alkylene, arylene, or aralkylene group optionally including one or more heteroatoms;
• A is (SO3)xM, (SO4)xM, (PO3)xM, or (PO4)xM;
• x is 1 or 2;
• and M is selected from the group consisting of H, Na, K, Li, Ca, Mg, Zn, a protonated primary amine, a protonated secondary amine, a protonated tertiary amine, a quaternary amine, and combinations thereof.

A moisturizing composition comprising a water-in-oil emulsion comprising:

• an oil phase;
• a water phase;
• and a vinyl polymer having a pKa of less than 4 comprising the reaction product of monomers comprising:
• about 60 wt-% to about 95 wt-% of at least one monoethylenically unsaturated alkyl (meth)acrylic monomer having the formula:
• 11
• wherein:
• R1 is hydrogen or methyl;
• and
• R2 is a linear, branched, or cyclic alkyl group optionally including one or more heteroatoms;
• and
• about 5 wt-% to about 40 wt-% of at least one low pKa acid-containing monomer, or salt thereof, having the formula:
• 12
• wherein:
• X is O or NR5;
• R3 and R5 are each independently hydrogen or methyl;
• R4 is a linear, branched, or cyclic alkylene, arylene, or aralkylene group optionally including one or more heteroatoms;
• A is (SO3)xM, (SO4)xM, (PO3)xM, or (PO4)xM;
• X is 1 or 2;
• and
• M is selected from the group consisting of H, Na, K, Li, Ca, Mg, Zn, a protonated primary amine, a protonated secondary amine, a protonated tertiary amine, a quaternary amine, and combinations thereof.

A tissue antiseptic composition comprising a water-in-oil emulsion comprising:

• a vinyl polymer having a pKa of less than 4 comprising anionic group-containing side chains and alkoxy-containing side chains, wherein the alkyl group of the alkoxy-containing side chain has at least 4 carbon atoms on average in a cyclic, branched-, or straight-chain configuration and optionally includes one or more heteroatoms;
• an oil phase;
• a water phase;
• and an antimicrobial.

A tissue antiseptic composition comprising a water-in-oil emulsion comprising:

• a vinyl polymer having a pKa of less than 4 comprising anionic group-containing side chains and alkoxy-containing side chains, wherein the alkyl group of the alkoxy-containing side chain has 4 to 50 carbon atoms on average in a cyclic, branched-, or straight-chain configuration and optionally includes one or more heteroatoms, wherein the anionic group-containing side chains comprise groups selected from the group consisting of (SO3)xM, (SO4)xM, (PO3)xM, (PO4)xM, and combinations thereof, wherein x is 1 or 2 and M is selected from the group consisting of Na, K, Li, Ca, Mg, Zn, a protonated primary amine, a protonated secondary amine, a protonated tertiary amine, a quaternary amine, and combinations thereof;
• an oil phase;
• a water phase;
• and an antimicrobial.

A tissue antiseptic composition comprising a water-in-oil emulsion comprising:

• an oil phase;
• a water phase;
• an antimicrobial;
• and a vinyl polymer having a pKa of less than 4 comprising the reaction product of monomers comprising:
• about 60 wt-% to about 95 wt-% of at least one monoethylenically unsaturated alkyl (meth)acrylic monomer having the formula:
• 13
• wherein:
• R1 is hydrogen or methyl;
• and
• R2 is a linear, branched, or cyclic alkyl group optionally including one or more heteroatoms;
• and
• about 5 wt-% to about 40 wt-% of at least one low pKa acid-containing monomer, or salt thereof, having the formula:
• 14
• wherein:
• X is O or NR5;
• R3 and R5 are each independently hydrogen or methyl;
• R4 is a linear, branched, or cyclic alkylene, arylene, or aralkylene group optionally including one or more heteroatoms;
• A is (SO3)xM, (SO4)xM, (PO3)xM, or (PO4)xM;
• x is 1 or 2;
• and
• M is selected from the group consisting of H, Na, K, Li, Ca, Mg, Zn, a protonated primary amine, a protonated secondary amine, a protonated tertiary amine, a protonated quaternary amine, and combinations thereof.

A personal care composition comprising a water-in-oil emulsion comprising:

• an oil phase;
• a water phase;
• and a vinyl polymer having a pKa of less than 4 comprising the reaction product of monomers comprising:
• about 60 wt-% to about 95 wt-% of at least one monoethylenically unsaturated alkyl (meth)acrylic monomer having the formula:
• 15
• wherein:
• R1 is hydrogen or methyl;
• and
• R2 is a linear, branched, or cyclic alkyl group optionally including one or more heteroatoms;
• and
• about 5 wt-% to about 40 wt-% of at least one low pKa acid-containing monomer, or salt thereof, having the formula:
• 16
• wherein:
• X is O or NR5;
• R3 and R5 are each independently hydrogen or methyl;
• R4 is a linear, branched, or cyclic alkylene, arylene, or aralkylene group optionally including one or more heteroatoms;
• A is (SO3)xM, (SO4)xM, (PO3)xM, or (PO4)xM;
• x is 1 or 2;
• and
• M is selected from the group consisting of H, Na, K, Li, Ca, Mg, Zn, a protonated primary amine, a protonated secondary amine, a protonated tertiary amine, a protonated quaternary amine, and combinations thereof.

A drug delivery composition comprising a water-in-oil emulsion comprising:

• a vinyl polymer having a pKa of less than 4 comprising anionic group-containing side chains and alkoxy-containing side chains, wherein the alkyl group of the alkoxy-containing side chain has at least 4 carbon atoms on average in a cyclic, branched-, or straight-chain configuration and optionally includes one or more heteroatoms;
• an oil phase;
• a water phase;
• and a pharmaceutical agent.

A drug delivery composition comprising a water-in-oil emulsion comprising:

• a vinyl polymer having a pKa of less than 4 comprising anionic group-containing side chains and alkoxy-containing side chains, wherein the alkyl group of the alkoxy-containing side chain has 4 to 50 carbon atoms on average in a cyclic, branched-, or straight-chain configuration and optionally includes one or more heteroatoms, wherein the anionic group-containing side chains comprise groups selected from the group consisting of (SO3)xM, (SO4)xM, (PO3)xM, (PO4)xM, and combinations thereof, wherein x is 1 or 2 and M is selected from the group of H, Na, K, Li, Ca, Mg, Zn, a protonated primary amine, a protonated secondary amine, a protonated tertiary amine, a quaternary amine, and combinations thereof;
• an oil phase;
• a water phase;
• and a pharmaceutical agent.

A drug delivery composition comprising a water-in-oil emulsion comprising:

• an oil phase;
• a water phase;
• a pharmaceutical agent;
• and a vinyl polymer having a pKa of less than 4 comprising the reaction product of monomers comprising:
• about 60 wt-% to about 95 wt-% of at least one monoethylenically unsaturated alkyl (meth)acrylic monomer having the formula:
• 17
• wherein:
• R1 is hydrogen or methyl;
• and
• R2 is a linear, branched, or cyclic alkyl group optionally including one or more heteroatoms;
• and
• about 5 wt-% to about 40 wt-% of at least one low pKa acid-containing monomer, or salt thereof, having the formula:
• 18
• wherein:
• X is O or NR5;
• R3 and R5 are each independently hydrogen or methyl;
• R4 is a linear, branched, or cyclic alkylene, arylene, or aralkylene group optionally including one or more heteroatoms;
• A is (SO3)xM, (SO4)xM, (PO3)xM, or (PO4)xM;
• x is 1 or 2;
• and
• M is selected from the group consisting of H, Na, K, Li, Ca, Mg, Zn, a protonated primary amine, a protonated secondary amine, a protonated tertiary amine, a protonated quaternary amine, and combinations thereof.