# US 8,784,853 B2 · Stabilization of household, body-care and food products by using benzotropolone containing plant extracts and/or related benzotropolone derivatives

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- Number: US 8,784,853 B2
- Document ID: US8784853B2
- Status: Granted
- Kind: B2
- Application number: 13/499,706
- Filed: 2010-10-05
- Published: 2012-09-13
- Granted: 2014-07-22
- Earliest claimed: 2009-10-06
- Assignees: BASF SE
- Applicants: Barbara Wagner; Oliver Reich; Alexander Mantler; Reinhold Öhrlein; Walter Fischer; Albert Schneider
- Inventors: Barbara Wagner; Oliver Reich; Alexander Mantler; Reinhold Öhrlein; Walter Fischer; Albert Schneider
- Web page: https://patentgrep.com/patent/US8784853B2

## CPC

- C07C 69/757: having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] in the acid moiety
- A61K 8/35: Ketones, e.g. benzophenone
- A61K 8/37: Esters of carboxylic acids
- A61K 8/4973: {with oxygen as the only hetero atom}
- A61Q 1/10: for eyes, e.g. eyeliner, mascara
- A61Q 19/00: Preparations for care of the skin
- C07C 49/755: a keto group being part of a condensed ring system with two or three rings, at least one ring being a six-membered aromatic ring
- C07C 69/33: esterified with hydroxy compounds having more than three hydroxy groups (esters of sugars C07H)
- C07D 317/70: condensed with ring systems containing two or more relevant rings
- C11B 5/0035: {Phenols; Their halogenated and aminated derivates, their salts, their esters with carboxylic acids}
- C11C 5/002: {Ingredients}
- C11D 3/0084: {Antioxidants; Free-radical scavengers}
- C11D 3/2072: {Aldehydes-ketones}
- C11D 3/2093: {Esters; Carbonates}
- C11D 3/2096: {Heterocyclic compounds}
- A61K 2800/522: Antioxidants; Radical scavengers
- A61K 2800/524: Preservatives
- A61Q 1/02: Preparations containing skin colorants, e.g. pigments (preparations in powder form A61Q1/12)
- A61Q 1/06: Lipsticks
- A61Q 3/02: Nail coatings
- A61Q 5/02: Preparations for cleaning the hair
- A61Q 5/06: Preparations for styling the hair, e.g. by temporary shaping or colouring
- A61Q 5/08: Preparations for bleaching the hair
- A61Q 17/04: Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
- A61Q 19/10: Washing or bathing preparations
- C07C 2602/12: the other ring being at least seven-membered
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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)
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C11B: PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES (drying-oils C09F)
- C11C: FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11D: DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL

## Abstract

Disclosed is the use of benzotropolone derivatives of formula (1), wherein R1, R2 and R7 independently from each other are hydrogen; C1-C3alkyl; or COR8; R3 is hydrogen; or COOR9 R4 is hydrogen; or C1-C3alkyl; R5 is hydrogen; hydroxy; C1-C3-alkoxy; or -0-(CO)—R10; R6 is hydrogen; C1-C3alkyl; or COR8; or R5 and R6 together may form a five or six membered ring; or R6 and R7 together form a five or six membered ring; and R8, R9, R10 independently of each other are C1-C30alkyl; for protecting body-care and household products from photolytic and oxidative degradation.

## Claims

### Claim 1

A body-care formulation comprising about 5 to about 10000 ppm, based on the total formulation of a benzotropolone derivatives of formula (1) therein
wherein
R1, R2 and R7 independently from each other are hydrogen; C1-C3alkyl; or COR8;
R3 is hydrogen; or COOR9;
R4 is hydrogen; or C1-C30 alkyl;
R5 is hydrogen; hydroxy; C1-C3-alkoxy; or —O—(CO)—R10;
R6 is hydrogen; C1-C30alkyl; or COR8; or
R5 and R6 together may form a five or six membered ring; or
R6 and R7 together form a five or six membered ring; and
R8, R9, R10 independently of each other are C1-C30alkyl.

### Claim 2 (depends on 1)

The body-care formulation according to claim 1, wherein
R1 is hydrogen; COR8; or C1-C30alkyl;
R2, R4 and R5 are hydrogen;
R3 is COOR9;
R6 and R7 independently from each other are hydrogen; C1-C30alkyl; or COR8; or
R6 and R7 together form a five or six membered ring; and
R8 is defined as in claim 1.

### Claim 3 (depends on 2)

The body-care product according to claim 2, wherein
R1 is hydrogen; or CO—CH3;
R2, R4 and R5 are hydrogen;
R3 is COO—C3H7;
R6 and R7 independently from each other are hydrogen; or CO—CH3; or
R6 and R7 together form a five or six membered ring.

### Claim 4 (depends on 1)

The body-care formulation according to claim 1, wherein
R1, R2 and R7 independently from each other are hydrogen; methyl; or —CO—CH3;
R3 is hydrogen; or —COOR9;
R4 is hydrogen; or C1-C30alkyl;
R5 is hydrogen; methoxy; or —O—(CO)—CH3;
R6 is hydrogen; methyl; or —CO—CH3; or
R5 and R6 together may form a five or six membered ring; or
R6 and R7 together form a five or six membered ring; and
R9 is C1-C10alkyl.

### Claim 5 (depends on 1)

The body-care formulation according to claim 1, wherein the benzotropolones derivatives of formula (I) are selected from the group consisting of

### Claim 6 (depends on 1)

The body-care formulation according to claim 1, wherein the body-care product is a product for the skin and its adnexa.

### Claim 7 (depends on 6)

The body-care formulation according to claim 6, wherein the body-care products are selected from skin-care products, bath and shower additives, preparations containing fragrances and odoriferous substances, hair-care products, dentifrices, deodorizing and antiperspirant preparations, decorative preparations, light protection formulations and preparations containing active ingredients.

### Claim 8 (depends on 6)

The body-care formulation according to claim 6, wherein the body-care products are selected from body oils, body lotions, body gels, treatment creams, skin protection ointments, shaving preparations and skin powders.

### Claim 9 (depends on 6)

The body-care formulation according to claim 6, wherein the body-care products contain fragrances and odoriferous substances which are selected from scents, perfumes, toilet waters and shaving lotions.

### Claim 10 (depends on 6)

The body-care formulation according to claim 6, wherein the body-care products are hair-care products and are selected from shampoos, hair conditioners, products for styling and treating hair, perming agents, hair sprays and lacquers, hair gels, hair fixatives and hair dyeing or bleaching agents.

### Claim 11 (depends on 6)

The body-care formulation according to claim 6, wherein the body-care products are decorative preparations and are selected from lipsticks, nail varnishes, eye shadows, mascaras, dry and moist make-up, rouge, powders, depilatory agents and suntan lotions.

### Claim 12 (depends on 6)

The body-care formulation according to claim 6, wherein the body-care products contain active ingredients and are selected from hormone preparations, vitamin preparations, vegetable extract preparations and antibacterial preparations.

### Claim 13 (depends on 1)

The body-care formulation according to claim 1, wherein the benzotropolone derivative of formula (1) is formula
wherein
R′2 and R′4 independently from each other are C1-C30alkyl;
R′1, R′5, R′6 and R′7 are C1-C30alkyl; or COR8.

### Claim 14 (depends on 1)

The body-care formulation according to claim 1, wherein the benzotropolone of formula (1) is formula
wherein
R′3 is a radical of formula
R′20 is C3-C30alkyl;
R′1, R′6 and R′7 are hydrogen; COR9; or C1-C30alkyl; and
R′9 is C1-C30alkyl.

### Claim 15 (depends on 1)

The body-care formulation according to claim 1 comprising therein anyone of the compounds selected from the group consisting of formulae (1′), (2′), (3′), (4′) and (5′)
wherein
R′1, R′2 and R′7 independently from each other are hydrogen; C1-C30alkyl; or COR8;
R′3 is hydrogen; or COOR9;
R′4 is hydrogen; or C1-C30alkyl;
R′5 is hydrogen; hydroxy; C1-C30-alkoxy; or —O—(CO)—R10;
R′6 is hydrogen; C1-C30alkyl; or COR8; or
R′5 and R′6 together may form a five or six membered ring; or
R′6 and R′7 together form a five or six membered ring; and
R′8, R′9, R′10 independently of each other are C1-C30alkyl;
with the proviso that in the compounds of formula (1′) either R7 and R8 together form a five or six membered ring; or R6 and R7 together form a five or six membered ring;
wherein
R′21 and R′22 independently of one another are hydrogen; OH; C1-C30alkyl; or C1-C30alkoxy, and
R′1, R′2, R′3, R′4, and R′7 are defined as in formula (1′);
wherein
R′21 and R′22 independently of one another are hydrogen; OH; C1-C30alkyl; or C1-C30alkoxy; and
R′1, R′2, R′3, R′4 and R′5 are defined as in formula (1′);
wherein
R′2 and R′4 independently from each other are C1-C30alkyl;
R′1, R′5, R′6 and R′7 are C1-C30alkyl; or COR8; and
R′8 is defined as in formula (1′);
and
wherein
R′3 is a radical of formula
R′20 is C3-C30alkyl;
R′1, R′6 and R′7 are hydrogen; COR9; or C1-C30alkyl; and
R′9 is C1-C30alkyl.
