# US 7,611,725 B2 · Additives and products including oligoesters

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- Number: US 7,611,725 B2
- Document ID: US7611725B2
- Status: Granted
- Kind: B2
- Application number: 10/356,208
- Filed: 2003-01-31
- Published: 2003-10-23
- Granted: 2009-11-03
- Earliest claimed: 2002-01-31
- Assignees: Croda, Inc.
- Inventors: Abel G. Pereira; Helena S. Barinova; Christopher Westergom
- Web page: https://patentgrep.com/patent/US7611725B2

## CPC

- A61K 8/585: {Organosilicon compounds}
- A61K 8/45: Derivatives containing from 2 to 10 oxyalkylene groups
- A61P 17/00: Drugs for dermatological disorders
- A61Q 5/02: Preparations for cleaning the hair
- A61Q 5/12: Preparations containing hair conditioners
- A61Q 15/00: Anti-perspirants or body deodorants (deodorisation of air A61L9/00)
- A61Q 17/04: Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
- 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

## Abstract

The present invention relates to oligoesters and their use or the creation of additives. Oligoester containing additives and/or oligoesters themselves may be used for formulating pharmaceutical preparations, cosmetics or personal care products such as shampoos and conditioners. These oligoesters are particularly useful for the creation of multi-purpose additives that can impart conditioning, long substantivity and/or UV protection. Individual oligoesters and oligoester mixtures are described.

## Claims

### Claim 1

A compound of Formula (VIII)
wherein R1 and R2 are independently
hydrogen, or a saturated or unsaturated, straight chain or branched, substituted or unsubstituted alkyl, alkylene, or alkoxy group having 1 to 60 carbon atoms;
R3, R5, R6, and R11 are independently hydrogen or a saturated or unsaturated, straight chain or branched, substituted or unsubstituted alkyl, alkylene, or alkoxy group having 1 to 60 carbon atoms;
R4 is a saturated or unsaturated, straight chain or branched, substituted or unsubstituted alkyl, alkylene, or alkoxy group having 1 to 60 carbon atoms;
R12 and R13 are independently straight chain or branched, saturated or unsaturated, substituted or unsubstituted, lower alkyl groups having 1 to 6 carbon atoms;
RUV has the structure —(CHx)b—NH—C(O)—R10;
(CHx)n, (CHx)m, and (CHx)b are independently straight chain or branched, saturated or unsaturated, alkyl or alkylene groups;
R10 is a substituted or unsubstituted, saturated or unsaturated group, wherein said group contains a substituted or unsubstituted 6-membered aromatic ring;
Y is a salt-forming anion;
Z is a salt-forming cation;
Z is 2-100;
x is 0, 1, or 2;
b is 1 to 10;
n is 1 to 6;
m is 1 to 300; and
N and M are independently 0 to 100.

### Claim 2 (depends on 1)

The compound of claim 1, wherein R12 and R13 are —CH(CH3)CH2—.

### Claim 3 (depends on 1)

The compound of claim 1, wherein R12O or R13O are independently ethoxy or propoxy.

### Claim 4 (depends on 1)

The compound of claim 1, wherein N is 0 to 40.

### Claim 5 (depends on 4)

The compound of claim 4, wherein N is 0 to 3.

### Claim 6 (depends on 1)

The compound of claim 1, wherein M is 0 to 40.

### Claim 7 (depends on 6)

The compound of claim 6, wherein M is 0 to 3.

### Claim 8 (depends on 1)

The compound of claim 1, wherein R10 is derived from para-aminobenzoic acid (PABA), benzophenone-1, benzophenone-2, benzophenone-3, benzophenone-4, benzophenone-6, benzophenone-8, benzophenone-12, methoxycinnamate, ethyl dihydroxypropyl-PABA, glyceryl PABA, homosalate, methyl anthranilate, octocrylene, octyl dimethyl PABA, octyl methoxycinnamate, octyl salicylate, PABA, 2-phenylbenzimidazole-5-sulphonic acid, triethanolamine salicylate, 3-(4-methylbenzylidene)-camphor, avobenzone, and 2,6-dicarboxynaphtalenic acid.

### Claim 9 (depends on 1)

The compound of claim 1, wherein R10 is
and where R11 is hydrogen, lower alkyl, halide or methoxy.

### Claim 10 (depends on 1)

The compound of claim 1, wherein RUV is
and R14 and R15 are independently H, —NH2, NO2, CH3O—, or (CH3)2N—.

### Claim 11 (depends on 10)

The compound of claim 10, wherein R14 and R15 are H.

### Claim 12 (depends on 1)

The compound of claim 1, said compound having the Formula (IX)
where R14 and R15 are independently hydrogen, —NH2, NO2, CH3O—, or (CH3)2N—;
m is 1 to 5; and
z is 4 to 6.

### Claim 13 (depends on 12)

The compound of claim 12, wherein R1 and R2 are H.

### Claim 14 (depends on 12)

The compound of claim 12, wherein R1 and R2 are independently
and m is 1-5.

### Claim 15 (depends on 12)

The compound of claim 12, wherein one of R1 or R2 is hydrogen and the other of R1 or R2 is
and m is 1-5.

### Claim 16 (depends on 1)

The compound of claim 1, further comprising at least one end cap.

### Claim 17 (depends on 1)

The compound of claim 1, further comprising two end caps.

### Claim 18

A compound of Formula (VIII)
wherein R1 and R2 are independently
hydrogen, or a saturated or unsaturated, straight chain or branched, substituted or unsubstituted alkyl, alkylene, or alkoxy group having 1 to 60 carbon atoms;
R3, R5, R6, and R11 are independently hydrogen or a saturated or unsaturated, straight chain or branched, substituted or unsubstituted alkyl, alkylene, or alkoxy group having 1 to 60 carbon atoms;
R4 is a saturated or unsaturated, straight chain or branched, substituted or unsubstituted alkyl, alkylene, or alkoxy group having 1 to 60 carbon atoms;
R12 and R13 are independently straight chain or branched, saturated or unsaturated, substituted or unsubstituted, lower alkyl groups having 1 to 6 carbon atoms;
RUV has the structure —(CHx)b—NH—C(O)—R10;
(CHx)n, (CHx)m, and (CHx)b are independently straight chain or branched, saturated or unsaturated alkyl or alkylene groups;
R10 is a substituted or unsubstituted, saturated or unsaturated group, wherein said group contains a substituted or unsubstituted 6-membered aromatic ring;
Y is a salt-forming anion;
Z is a salt-forming cation;
Z is 2-100;
x is 0, 1, or 2;
b is 1 to 10;
n is 1 to 6;
m is 1 to 300; and
N and M are independently 0 to 100,
with the proviso that there is at least one alkoxy group.

### Claim 19 (depends on 18)

The compound of claim 18, wherein R12 and R13 are —CH(CH3)CH2—.

### Claim 20 (depends on 18)

The compound of claim 18, wherein R12O or R13O are independently ethoxy or propoxy.

### Claim 21 (depends on 18)

The compound of claim 18, wherein R10 is derived from para-aminobenzoic acid (PABA), benzophenone-1, benzophenone-2, benzophenone-3, benzophenone-4, benzophenone-6, benzophenone-8, benzophenone-12, methoxycinnamate, ethyl dihydroxypropyl-PABA, glyceryl PABA, homosalate, methyl anthranilate, octocrylene, octyl dimethyl PABA, octyl methoxycinnamate, octyl salicylate, PABA, 2-phenylbenzimidazole-5-sulphonic acid, triethanolamine salicylate, 3-(4-methylbenzylidene)-camphor, avobenzone, and 2,6-dicarboxynaphtalenic acid.

### Claim 22 (depends on 18)

The compound of claim 18, wherein R10 is
and where R11 is hydrogen, lower alkyl, halide or methoxy.

### Claim 23 (depends on 18)

The compound of claim 18, wherein RUV is
and R14 and R15 are independently H, —NH2, NO2, CH3O—, or (CH3)2N—.

### Claim 24 (depends on 23)

The compound of claim 23, wherein R14 and R15 are H.

### Claim 25

A compound Poly(N-Hydroxypolyoxypropylethyl) N-Adipyl-Poly-Oxypropyl)-N-Methyl-N-(2-Hydroxy-3-Cinnamidopropyl Dimethyl Ammonium Chloride) Methane Sulfonate.

### Claim 26

A compound having the structure:
wherein
Y is a salt-forming anion; and
Z is a salt-forming cation.

### Claim 27

A compound having the structure:

### Claim 28 (depends on 1)

A pharmaceutical, cosmetic, or personal care product comprising:
a pharmaceutically or cosmetically-acceptable solvent; and
said oligoester of claim 1 present in an amount of from about 0.01% to about 99.0% by weight based on the combined weight of said oligoester and said solvent; and
at least one active or additional ingredient, provided in an amount which is effective for its intended use,
wherein said pharmaceutical, cosmetic, or personal care product is provided in the form of a lotion, gel, spray, cream and the like, hand cleaner, bath composition, suntan oil, antiperspirant composition, perfume, cologne, cold cream, pre-shave, deodorant, treated powder, nose spray, bandage, transdermal drug applicator, skin moisturizer, facial cleanser, cleansing cream, skin gel, shampoo, hair conditioner rinse, cream rinse, detergent, make-up product, permanent waving product, lipstick, mascara, blush, foundation, rouge, mousse, spray, styling gel, nail polish, nail conditioner, dye or hair coloring product.

### Claim 29 (depends on 28)

The pharmaceutical, cosmetic, or personal care product of claim 28, wherein said oligoester is present in an amount of from about 5% to about 95% by weight based on the combined weight of said oligoester and said solvent.

### Claim 30 (depends on 28)

The pharmaceutical, cosmetic, or personal care product of claim 28, wherein said product is provided in the form of skin moisturizer, facial cleanser, shampoo, hair conditioner, cream rinse, styling gel, dye or hair coloring product.

### Claim 31 (depends on 28)

The pharmaceutical, cosmetic, or personal care product of claim 28, wherein said oligoester includes between about 2 and about 100 structural units.

### Claim 32 (depends on 28)

The pharmaceutical, cosmetic, or personal care product of claim 28, wherein said oligoester has a molecular weight of about 100,000 or less.

### Claim 33 (depends on 28)

The pharmaceutical, cosmetic, or personal care product of claim 28, wherein said oligoester includes at least one alkoxy group bound to, and forming part of at least one of said diol fragments.

### Claim 34 (depends on 28)

The pharmaceutical, cosmetic, or personal care product of claim 28, wherein said at least one active or additional ingredients, provided in an amount which is effective for its intended use include pharmaceutically active ingredients, UV-absorbers, fragrances, pigments, dyes, hair or skin conditioners, cleaning agents, hair styling agents, antidandruff agents, hair growth promoters, perfumes, sunscreen compounds, pigments, moisturizers, film formers, humectants, alpha-hydroxy acids, hair colors, make-up agents, detergents, thickening agents, emulsifiers, antiseptic agents, deodorant actives, surfactants, agents which enhance permeation into or through the skin, emollients, emulsifiers, humectants, softeners, lubricants, penetrants, plasticizers, dispersants, thickening agents, preservatives, buffers, chelating agents, foaming agents, coupling agents, proteins, salts, and oils all provided in conventional and/or approved amounts.

### Claim 35 (depends on 1)

An additive for pharmaceutical, cosmetic, or personal care products comprising:
a pharmaceutically or cosmetically acceptable solvent; and
an oligoester of claim 1, said oligoester being present in an amount of from about 0.01% to about 99.0% by weight of said additive.