# US 9,867,770 B2 · Silyl polymeric benzoic acid ester compounds, uses, and compositions thereof

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- Number: US 9,867,770 B2
- Document ID: US9867770B2
- Status: Granted
- Kind: B2
- Application number: 14/573,098
- Filed: 2014-12-17
- Published: 2015-07-09
- Granted: 2018-01-16
- Earliest claimed: 2009-10-15
- Assignees: Interquim, S.A.
- Applicants: Interquim, S.A.
- Inventors: Adaya Gallardo Sanchez; Santiago Nonell Marrugat; Francisco Marquillas Olondriz; Joan Sallares; Ricardo Miralles Bacete
- Web page: https://patentgrep.com/patent/US9867770B2

## CPC

- A61K 8/898: containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
- A61K 8/0241: {Containing particulates characterized by their shape and/or structure (see also A61K8/04, A61K8/11, and A61K8/14, further aspects are classified in A61K2800/40 and subcodes)}
- A61K 8/585: {Organosilicon compounds}
- A61P 17/16: Emollients or protectives, e.g. against radiation
- A61Q 17/04: Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
- C07F 7/1804: {Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896)}
- C08G 77/18: to alkoxy or aryloxy groups
- C08G 77/26: nitrogen-containing groups
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

The present invention relates to organosilicon polymers containing benzoic acid esters in form of particles, process for their preparation, cosmetic or dermatological composition comprising them, as well as their use for protecting a human or animal living body from UV radiation.

## Claims

### Claim 1

A process for the preparation of an organosilicon progressive photoprotective polymer, which comprises the reaction of a monomer of formula (I):
wherein:
R is selected from the group consisting of (i), (ii), (iii), and (iv):
R1, R2, R3, R4 and R5 are independently selected from the group consisting of H, linear or branched (C1-C6)alkyl, (C3-C6)cycloalkyl, OR6, NH2, NHR7, NR8R9, COOH, COOR10, CONH2, CONHR11, CONR12R13, SO2NH2, SO2NHR14, and SO2NR15R16;
R6 is linear or branched (C1-C6)alkyl or (C3-C6)cycloalkyl;
R7 is linear or branched (C1-C6)alkyl or (C3-C6)cycloalkyl;
R8 is linear or branched (C1-C6)alkyl or (C3-C6)cycloalkyl;
R9 is linear or branched (C1-C6)alkyl or (C3-C6)cycloalkyl; or R8 and R9 taken together with the nitrogen atom to which they are attached form a pyrrolidine, piperidine or morpholine ring;
R10 is linear or branched (C1-C6)alkyl or (C3-C6)cycloalkyl;
R11 is linear or branched (C1-C6)alkyl or (C3-C6)cycloalkyl;
R12 is linear or branched (C1-C6)alkyl or (C3-C6)cycloalkyl;
R13 is linear or branched (C1-C6)alkyl or (C3-C6)cycloalkyl; or R12 and R13 taken together with the nitrogen atom to which they are attached form a pyrrolidine, piperidine or morpholine ring;
R14 is linear or branched (C1-C6)alkyl or (C3-C6)cycloalkyl;
R15 is linear or branched (C1-C6)alkyl or (C3-C6)cycloalkyl;
R16 is linear or branched (C1-C6)alkyl or (C3-C6)cycloalkyl; or R15 and R16 taken together with the nitrogen atom to which they are attached form a pyrrolidine, piperidine or morpholine ring;
A is H, linear or branched (C1-C6)alkyl, (C3-C6)cycloalkyl, OR′1, NH2, NHR′2 or NR′3R′4;
L is a single bond, —CH2—, or —CH2—CH(RL)—
Z is NH or O;
Ra is linear or branched (C1-C6)alkyl, linear or branched (C2-C6)alkenyl, (C3-C6)cycloalkyl or phenyl;
Rb is linear or branched (C1-C6)alkyl, linear or branched (C2-C6)alkenyl, (C3-C6)cycloalkyl or phenyl;
Rc is linear or branched (C1-C6)alkyl, linear or branched (C2-C6)alkenyl, (C3-C6)cycloalkyl or phenyl;
R′1 is linear or branched (C1-C6)alkyl or (C3-C6)cycloalkyl;
R′2 is linear or branched (C1-C6)alkyl or (C3-C6)cycloalkyl;
R′3 is linear or branched (C1-C6)alkyl or (C3-C6)cycloalkyl;
R′4 is linear or branched (C1-C6)alkyl or (C3-C6)cycloalkyl; or R′3 and R′4 taken together with the nitrogen atom to which they are attached form a pyrrolidine, piperidine or morpholine ring;
RL is H, linear or branched (C1-C6)alkyl or (C3-C6)cycloalkyl;
n is an integer selected from 0 and 1;
p is an integer selected from 2, 3 and 4;
s is an integer selected from 0 and 1;
t is an integer selected from 0 and 1;
with a compound of formula (IV):
wherein:
Rd is a linear or branched (C1-C6)alkyl;
Re, Rf and Rg are independently a linear or branched (C1-C6)alkyl, linear or branched (C2-C6)alkenyl, (C3-C6)cycloalkyl or phenyl,
w1 and w2 are independently 0 or 1,
in an alkanol/water mixture, wherein the alkanol is a linear or branched alkanol having 1 to 6 carbon atoms,
and in the presence of a nitrogen-containing basic compound selected from the group consisting of ammonia, mono-alkylamine, di-alkylamine, tri-alkylamine, mono-alkanolamine, di-alkanolamine, and tri-alkanolamine, wherein both alkyl and alkanol groups are linear or branched having 1 to 6 carbon atoms,
characterized in that the organosilicon progressive photoprotective polymer exhibits a micro- or nanoparticle form.

### Claim 2 (depends on 1)

The process according to claim 1, wherein the alkanol/water mixture is an ethanol/water mixture.

### Claim 3 (depends on 1)

Method of protecting a human or animal living body from UV radiation, which method comprises the application to said human or animal body of a cosmetically or dermatologically effective amount of an organosilicon progressive photoprotective polymer obtainable by a process as defined in claim 1.

### Claim 4 (depends on 1)

Method of obtaining a photochemical precursor of UV absorbers wherein the method comprises the use of a photoprotective polymer obtainable by a process as defined in claim 1.

### Claim 5 (depends on 1)

Method of protecting a human or animal living body from UV radiation, which method comprises the application to said human or animal body of a cosmetically or dermatologically effective amount of an organosilicon progressive photoprotective polymer obtainable by a process as defined in claim 1, characterized by a progressive UV protection depending on the time to sun exposition and the degree of sun radiation.