Polysiloxane conjugates as fragrance delivery systems

Patent metadata

Field	Value
Publication number	US-9765282-B2
Application number	US-201414900157-A
Country	US
Kind code	B2
Filing date	Jun 17, 2014
Priority date	Jun 19, 2013
Publication date	Sep 19, 2017
Grant date	Sep 19, 2017

Abstract

The present invention relates to the field of perfumery. More particularly, it concerns polymers derived from siloxane derivatives and comprising at least one β-thio carbonyl moiety capable of liberating an active molecule such as, for example, an α,β-unsaturated ketone or aldehyde. The present invention concerns also the use of polymers in perfumery as part of a perfuming or malodor counteracting composition as well as the perfuming compositions or perfumed articles comprising the invention's compounds.

First claim

What is claimed is:

1. A polymer, capable of releasing in a controlled manner an odoriferous α,β-unsaturated ketone or aldehyde, and comprising at least one repeating unit of formula

wherein the double hatched lines indicate the bonding to another repeating unit and
R 1 represents a C 1 to C 16 hydrocarbon group;
P represents a group susceptible of generating an odoriferous α,β-unsaturated ketone or aldehyde and is represented by formula

in which the wavy line indicates the location of the bond between said P and X;
R 2 represents a hydrogen atom, a C 1 to C 15 linear, cyclic or branched alkyl, alkenyl or alkadienyl radical, optionally substituted by one to four C 1 to C 4 alkyl groups; and R 3 , R 4 and R 5 , independently of each other, represent a hydrogen atom, a C 6 to C 10 aromatic ring or a C 1 to C 15 linear, cyclic or branched alkyl, alkenyl or alkadienyl radical, possibly substituted by C 1 to C 4 alkyl groups; or two, or three, of the groups R 1 to R 4 are bound together to form a saturated or unsaturated ring having 5 to 20 carbon atoms and, including the carbon atom to which said R 2 , R 3 , R 4 or R 5 groups are bound, this ring being optionally substituted by one or two C 1 to C 8 linear, branched or cyclic alkyl or alkenyl groups;
X represents a sulfur atom; and
G represents a C 2 -C 5 hydrocarbon group optionally comprising 1 or 2 oxygen, sulfur and/or nitrogen atoms.

2. A polymer according to claim 1 , characterized in that P represents a group of the formulae (P-1) to (P-13), in the form of any one of its isomers:

in which formulae the wavy lines have the meaning indicated in claim 1 and the dotted lines represent a single or double bond, R 9 being a hydrogen atom or a methyl group and R 10 representing a hydrogen atom, a hydroxy or methoxy group or a C 1 -C 4 linear or branched alkyl group.

3. A method to confer, enhance, improve or modify the odor properties of a perfuming composition or of a perfumed article, which method comprises adding to said composition or article an effective amount of at least one polymer according to claim 2 .

4. A polymer according to claim 1 , wherein R 1 represents a methyl group.

5. A polymer according to claim 1 , wherein polymer is characterized by a viscosity comprised in the range between 0.5 (Pa·s) and 60 (Pa·s).

6. A perfuming composition comprising:
i) as perfuming ingredient, at least one polymer according to claim 1 ;
ii) at least one ingredient selected from the group consisting of a perfumery carrier and a perfumery base; and
iii) optionally at least one perfumery adjuvant.

7. A perfuming consumer product comprising as perfuming ingredient, at least one polymer according to claim 1 .

8. A perfuming consumer product according to claim 7 , in the form of a perfume, a fabric care product, a body-care product, an air care product or a home care product.

9. A perfuming consumer product according to claim 7 , in the form of a rinse-off product.

10. A method to confer, enhance, improve or modify the odor properties of a perfuming composition or of a perfumed article, which method comprises adding to said composition or article an effective amount of at least one polymer according to claim 1 .

11. A polymer, capable of releasing in a controlled manner an odoriferous α,β-unsaturated ketone or aldehyde, and comprising at least one repeating unit of formula

wherein the double hatched lines indicate the bonding to another repeating unit and
R 1 represents a C 1 to C 16 hydrocarbon group;
P represents a group susceptible of generating an odoriferous α,β-unsaturated ketone or aldehyde and is represented by formula

in which the wavy line indicates the location of the bond between said P and X;
R 2 represents a hydrogen atom, a C 1 to C 15 linear, cyclic or branched alkyl, alkenyl or alkadienyl radical, optionally substituted by one to four C 1 to C 4 alkyl groups; and
R 3 , R 4 and R 5 , independently of each other, represent a hydrogen atom, a C 6 to C 10 aromatic ring or a C 1 to C 15 linear, cyclic or branched alkyl, alkenyl or alkadienyl radical, possibly substituted by C 1 to C 4 alkyl groups; or two, or three, of the groups R 1 to R 4 are bound together to form a saturated or unsaturated ring having 5 to 20 carbon atoms and, including the carbon atom to which said R 2 , R 3 , R 4 or R 5 groups are bound, this ring being optionally substituted by one or two C 1 to C 8 linear, branched or cyclic alkyl or alkenyl groups;
X represents a sulfur atom; and
G represents a C 2 -C 8 hydrocarbon group optionally comprising 1 or 2 oxygen, sulfur and/or nitrogen atoms; and
repeating units of the formulae (III) or (IV)

wherein the double hatched lines, G and R 1 have the same meaning as in any one of claims 1 to 2 ; each R 11 group represents independently of each other a C 6 to C 12 aromatic ring or a C 1 to C 18 linear, cyclic or branched alkyl group, or a C 1 to C 6 linear, cyclic or branched alkyloxy group; and Y represents a group of formulae a) to g)

with A being a hydrogen atom or an alkali metal atom, R 12 being a C 1 to C 18 linear or branched alkyl group, R 13 being a hydrogen atom or a R 12 group and Z being a monoanion.

12. A polymer according to claim 11 , wherein each R 11 is a methyl group.

13. A polymer according to claim 11 , wherein Y represents a group of formula d), f) or g).

14. A polymer according to claim 11 , wherein polymer is linear and comprises only:
siloxane units of formula (III) and/or (IV); and/or
siloxane units of formula (V)
—O—Si(OR 13 ) a (G-B) b (R 14 ) c   (V)

wherein each a, b and c is either 0, 1, 2 or 3 and (a+b+c)=3;
G represents a group as defined in claim 1 or 2 ;
each B represents independently from each other a X-P group, as defined in claim 1 or 2 , or a Y group;
each R 13 represents independently from each other a hydrogen atom or a R 12 group; and
each R 14 represents independently from each other a R 1 or a R 11 group as defined in claims 1 to 2 ; and
siloxane units of formula (I), as defined in any one of claims 1 to 2 .

15. A polymer according to claim 11 , wherein polymer is a linear co-polymer wherein the molar ratio of the repeating units (I)/[(III)+(IV)] is between 85/15 and 45/55;
X represents a sulfur atom;
R 1 is a methyl group;
G represents a linear C 3 -C 5 alkanediyl group; and
said polymer having
a weight average molecular weight comprised in the range between 1000 Da and 5000 Da;
terminal groups of formula:
—O—Si(OR 13 ) a (R 14 ) c   (V′)

wherein each a and c is either 0, 1, 2 or 3 and (a+c)=3;
each R 13 represents independently from each other a hydrogen atom or a R 12 group as defin

Assignees

• Firmenich & Cie

Inventors

• Berthier Damien
• Wu Yongtao
• Herrmann Andreas
• Struillou Arnaud
• Rassat Estelle
• Paret Nicolas

Classifications

• A61Q5/12

  Preparations containing hair conditioners · CPC title

• C11D3/507

  Compounds releasing perfumes by thermal or chemical activation · CPC title

• C11B9/0042

  compounds containing condensed hydrocarbon rings · CPC title

• C11B9/0053

  both rings being six-membered · CPC title

• D06M13/005

  Compositions containing perfumes; Compositions containing deodorants · CPC title