Sunblocking polymers and their formulation

• US 5,487,885 A
• Filed: 12/09/1993
• Issued: 01/30/1996
• Est. Priority Date: 12/21/1992
• Status: Expired due to Fees

• Current Assignee: Biophysica, Inc.
• Original Assignee: Biophysica, Inc.
• Inventors: Douglass, James G. III, Bakir, Farid, Sovak, Milos, Terry, Ronald C.
• Primary Examiner(s): Kulkosky, Peter F.
• Application Number:
  US08/164,881
• Time in Patent Office: 782 Days
• Field of Search: 424/59, 526/328, 526/328.5, 526/329.5, 526/329.2, 526/304, 526/307, 526/307.7
• US Class Current: 424/59
• CPC Class Codes: A61K 2800/57 Compounds covalently linked to a(n inert) carrier molecule, e.g. conjugates, pro-fragrances
• CPC Class Codes: A61K 8/33 containing oxygen
• CPC Class Codes: A61K 8/35 Ketones, e.g. benzophenone
• CPC Class Codes: A61K 8/445 aromatic, i.e. the carboxylic acid directly linked to the aromatic ring
• CPC Class Codes: A61K 8/8158 Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers
• CPC Class Codes: A61K 8/90 Block copolymers A61K8/89 takes precedence
• CPC Class Codes: A61Q 17/04 Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
• CPC Class Codes: C07C 229/60 with amino and carboxyl groups bound in meta- or para- positions
• CPC Class Codes: C07C 233/20 having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
• CPC Class Codes: C07C 233/33 with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
• CPC Class Codes: C07C 235/56 having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
• CPC Class Codes: C07C 237/42 having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
• CPC Class Codes: C07C 69/54 Acrylic acid esters; Methacrylic acid esters
• CPC Class Codes: C07C 69/92 with etherified hydroxyl groups

Abstract

Novel polymeric compositions and their intermediates are provided, providing for broad range protection from ultraviolet radiation. Acryl polymers comprising at least two different ultraviolet absorbing moieties having different light absorbing ranges are employed in conjunction with another hydrophilic monomer to provide sunscreen formulations for invisibility, and enhanced protection, without deleterious effects in the dermis.

Claims

1. A polyacrylic acid based sunscreen composition having as its UV absorbing moieties:

for UV-A, a compound of the formula;

##STR4## wherein;

n is 0 or 1;

Z is oxy or amino of not more than about than about 12 carbon atoms;

Y is non-oxo carbonyl of not more than about 12 carbon atoms; and

W is oxy or amino;

for UV-B, a compound of the formula;

##STR5## wherein;

R² is hydrogen or alkyl of up to 6 carbon atoms;

R³ is a divalent hydrocarbylene group;

W and R are as defined above;

for UV-C, a compound of the formula;

##STR6## wherein;

R⁴ is hydrogen or alkyl of from 1 to 6 carbon atoms; and

the other symbols have been defined above; and

an oxyaliphatic substituted acrylic acid of the formula;

space="preserve" listing-type="equation">R.sup.5 WCOC(R)═

CH.sub.2

wherein R⁵ is an aliphatic group of from 1 to 4 carbon atoms having from 1 to 3 oxy groups, wherein the other symbols have been defined previously; and

the polymer is insoluble in water and swellable in a polyethylene glycol-water composition comprising from about 50-95% polyethylene glycol.

2. A polyacrylic acid according to claim 1, wherein the UV absorbers are from about 30-70 number % of UV-B, at least 20 number % UV-A, and the remainder UV-C and said polymer comprises from about 1 to 3 mole percent based on total monomer of a cross-linking acrylic monomer.

3. A sunscreen formulation comprising an effective amount for absorbing ultraviolet sunlight of a polyacrylic sunscreen having as its UV absorbing moieties;

for UV-A, a compound of the formula;

##STR7## wherein;

n is 0 or 1;

R is H, alkyl of from 1 to 3 carbon atoms, which may be substituted with a functional group of from 0 to 3 carbon atoms having from 1 to 2N and O heteroatoms;

Z is oxy or amino of not more than about than about 12 carbon atoms;

Y is non-oxo carbonyl of not more than about 12 carbon atoms; and

W is oxy or amino;

for UV-B, a compound of the formula;

##STR8## wherein;

R² is a divalent hydrocarbylene group or substituted derivative thereof;

R³ is hydrogen or alkyl of up to 6 carbon atoms;

W and R are as defined above;

for UV-C, a compound of the formula;

##STR9## wherein;

R⁴ is hydrogen or alkyl of from 1 to 6 carbon atoms; and

the other symbols have been defined above; and

an oxyaliphatic substituted acrylic acid of the formula;

space="preserve" listing-type="equation">R.sup.5 WCOC(R)═

CH.sub.2

wherein R⁵ is an aliphatic group of from 1 to 4 carbon atoms having from 1 to 3 oxy groups, wherein the other symbols have been defined previously; and

the polymer is insoluble in water and swellable in a polyethylene glycol-water composition comprising from about 50-95% polyethylene glycol;

and a physiologically acceptable vehicle.

4. A sunscreen formulation according to claim 3, wherein said vehicle comprises a polypropylene glycol.

5. A sunscreen formulation according to claim 3, wherein said polyacrylic acid sunscreen is cross-linked with from about 1 to 3 percent of an acrylic cross-linking monomer and further comprises an hydroxyalkylacryl monomer.