NOVEL HETEROCYCLIC SUBSTITUTED CONDENSATION POLYMERS

• US 20090068124A1
• Filed: 02/23/2007
• Published: 03/12/2009
• Est. Priority Date: 03/03/2006
• Status: Active Grant

• Current Assignee: DSM IP Assets BV (DSM-Firmenich AG)
• Original Assignee: DSM IP Assets BV (DSM-Firmenich AG)
• Inventors: Derks, Franciscus, Mendrok, Christine, Beumer, Raphael
• Granted Patent: US 8,951,509 B2
• Time in Patent Office: Days
• US Class Current: 424/54
• CPC Class Codes: A61K 2800/5426 cationic
• CPC Class Codes: A61K 2800/57 Compounds covalently linked to a(n inert) carrier molecule, e.g. conjugates, pro-fragrances
• CPC Class Codes: A61K 8/046 Aerosols; Foams
• CPC Class Codes: A61K 8/85 Polyesters
• CPC Class Codes: A61K 8/88 Polyamides
• CPC Class Codes: A61Q 1/02 Preparations containing skin colorants, e.g. pigments preparations in powder form A61Q1/12
• CPC Class Codes: A61Q 19/00 Preparations for care of the skin
• CPC Class Codes: A61Q 3/02 Nail coatings
• CPC Class Codes: A61Q 5/006 Antidandruff preparations
• CPC Class Codes: A61Q 5/008 Preparations for oily hair
• CPC Class Codes: A61Q 5/02 Preparations for cleaning the hair
• CPC Class Codes: A61Q 5/06 Preparations for styling the hair, e.g. by temporary shaping or colouring
• CPC Class Codes: A61Q 5/12 Preparations containing hair conditioners
• CPC Class Codes: C08G 69/44 Polyester-amides
• CPC Class Codes: C11D 3/3719 Polyamides or polyimides

Abstract

The invention relates to novel optionally quaternized or protonated condensation polymers having at least one heterocyclic end-group connected to the polymer backbone through a unit derived from an alkylamide, the connection comprising an optionally substituted ethylene group and to the use thereof in body care products and household products.

Claims

1. An optionally quaternized or protonated condensation polymer having at least one heterocyclic end-group connected to the polymer backbone through a unit derived from an alkylamide, the connection comprising an optionally substituted ethylene group.

2. A condensation polymer according to claim 1 wherein the condensation polymer contains at least two groups according to formula (I)

wherein

Y is, independently of each other, a hydrogen atom, a (C₁-C₂₀) alkyl group, a (C₆-C₁₀) aryl group or

X is, independently of each other, NHet or

B is a (C₆-C₂₄) aryldiradical or a (C₂-C₂₄) alkyldiradical;

R¹, R², R³, R⁴, R⁵ and R⁶ are, independently of each other, hydrogen atoms, (C₆-C₁₀) aryl groups or (C₁-C₈) alkyl groups;

R⁷ and R⁸ are, independently of each other, hydrogen atoms, optionally heteroatom substituted (C₆-C₁₀) aryl groups or optionally heteroatom substituted (C₁-C₂₈) alkyl groups or

R⁷ and R⁸ together with the nitrogen atom to which they are attached form a 5 or 6 membered ring wherein optionally one or several C-atoms are replaced by —

NH, —

N—

(C₁-C₂₀) alkyl, —

N-aryl, —

O—

or —

S—

;

NHet is, independently of each other, a mono-, bi- or multicyclic nitrogen containing heterocyclyl group attached via a nitrogen atom to the polymer which may be aromatic or partly or completely hydrogenated and may contain additional heteroatoms such as nitrogen, oxygen or sulfur and which may optionally be substituted.

and wherein at least one group NHet is present in the condensation polymer of formula I.

3. A condensation polymer according to claim 2, characterized in that n is 1.

4. A condensation polymer according to claim 1, characterized in that the polymer is of the formula (II):

in which;

Y is

a hydrogen atom, a (C₁-C₂₀) alkyl group or a (C₆-C₁₀) aryl group;

A is

or OH;

B is a (C₆-C₂₄) aryldiradical or a (C₂-C₂₄) alkyldiradical;

X¹ is

X² is a OH group, X¹, NHet or

R¹, R², R³, R⁴, R⁵ and R⁶ are, independently of each other, hydrogen atoms, (C₆-C₁₀) aryl groups or (C₁-C₈) alkyl groups or —

CH₂—

OX²;

R⁷ and R⁸ are, independently of each other, hydrogen atoms, optionally heteroatom substituted (C₆-C₁₀) aryl groups or optionally heteroatom substituted (C₁-C₂₈) alkyl groups or

R⁷ and R⁸ together with the nitrogen atom to which they are attached form a 5 or 6 membered ring wherein optionally one or several C-atoms are replaced by —

NH, —

N—

(C₁-C₂₀) alkyl, —

N-aryl, —

O—

or —

S—

;

NHet is, independently of each other, a mono-, bi- or multicyclic nitrogen containing heterocyclyl group attached via a nitrogen atom to the polymer which may be aromatic or partly or completely hydrogenated and may contain additional heteroatoms such as nitrogen, oxygen or sulfur and which may optionally be substituted.

and wherein at least one group NHet is present in the condensation polymer of formula II.

5. A condensation polymer according to claim 1, characterized in that the condensation polymer is either linear or branched.

6. A condensation polymer according to claim 1, characterized in that the condensation polymer has a number of heterocyclic end-groups equal to or greater than 3.

7. A condensation polymer according to claim 1 characterized in that the condensation polymer is of the formula (III)

in which

A is

or OH

B is a (C₆-C₂₄) aryldiradical or a (C₂-C₂₄) alkyldiradical;

X¹ is

X² is a OH group X¹, NHet or,

R³ and R⁶ are, independently of each other, hydrogen atoms, (C₆-C₁₀) aryl groups or (C₁-C₈) alkyl groups or —

CH₂—

OX²;

R⁷ and R⁸ are, independently of each other, optionally heteroatom substituted (C₆-C₁₀) aryl groups or optionally heteroatom substituted (C₁-C₂₈) alkyl groups or

R⁷ and R⁸ together with the nitrogen atom to which they are attached form a 5 or 6 membered ring wherein optionally one or several C-atoms are replaced by —

NH, —

N—

(C₁-C₂₀) alkyl, —

N-aryl, —

O—

or —

S—

;

NHet is, independently of each other, a mono-, bi- or multicyclic nitrogen containing heterocyclyl group attached via a nitrogen atom to the polymer which may be aromatic or partly or completely hydrogenated and may contain additional heteroatoms such as nitrogen, oxygen or sulfur and which may optionally be substituted.

and wherein at least one group NHet is present in the condensation polymer of formula III.

8. A condensation polymer according to claim 1 characterized in that in the condensation polymer R¹ and R² are hydrogen atoms.

9. A condensation polymer according to claim 1 characterized in that in the condensation polymer R³ and R⁶ are (C₁-C₄) alkyl groups, preferably a methyl or ethyl group.

10. A condensation polymer according to claim 1, characterized in that NHet is selected from imidazole, benzimidazole, 1,2,4-triazole, hydantoin, and derivatives thereof.

11. A condensation polymer according to claim 1, characterized in that the condensation polymer has a weight average molecular mass between 600 g/mol to 50'"'"'000 g/mol, more preferably between 800 g/mol and 25'"'"'000 g/mol.

12. A condensation polymer according to claim 1, characterized in that the condensation polymer has a number average molecular mass between 500 g/mol to 15'"'"'000 g/mol, more preferably between 700 g/mol and 4'"'"'000 g/mol.

13. A condensation polymer according to claim 1, characterized in that the average number of NHet groups or the NHet groups in combination with dialkylamide end-groups per molecule of condensation polymer is between 2 and 250, more preferable between 3 and 50.

14. A condensation polymer according to claim 1, characterized in that one or several nitrogen atoms of the condensation polymer are present in quaternized forms or are protonated.

15. A condensation polymer according to claim 14, characterized in that the quaternized nitrogen atoms are quaternized with branched or cyclic (C₁-C₈) alkyl groups, unsaturated (C₁-C₈) alkyl groups, aryl groups, acrylic groups or mixtures thereof or are in the form of a betaine group.

16. A condensation polymer according to claim 14, characterized in that the quaternized nitrogen atoms of the condensation polymer are quaternized with methyl and/or ethyl groups.

17. Process for the preparation of a condensation polymer according to claim 1, characterized in that the polymer is obtained through polycondensation of a mono- and/or bis-hydroxyalkylamide of a dicarboxylic acid in the presence of a heterocyclic compound having a labile hydrogen atom and, optionally, a (mono-(dialkylamide))dicarboxylic acid.

18. Process for the preparation of a condensation polymer according to claim 1, characterized in that the polymer is obtained in a one-step procedure by reacting a cyclic anhydride, an alkanolamine and a heterocyclic compound having a labile hydrogen atom optionally in combination with a dialkylamine, to form a polyesteramide by polycondensation.

19. A body care product or household product comprising an effective amount of a condensation polymer according to claim 1.

20. A body care product or household product according to claim 19 wherein the effective amount is within a concentration range of 0.01 to 20 wt. % based on the total weight of the product.

21. A body care product or household product according to claim 19 to comprising additional cosmetic adjuvants and/or additives.

22. A body care product according to claim 19 selected from skin-care preparations;

bath and shower preparations;

liquid soaps;

bar soaps;

preparations containing scents, fragrances and odorant ingredients;

hair-care preparations;

dentifrices;

deodorizing and antiperspirant preparations;

decorative preparations;

light protecting preparations and preparations containing active ingredients.

23. A body care product according to claim 22 wherein the hair care preparation comprises additional additives and adjuvants used in hair care.

24. A method of treating hair in which a hair care preparation as described in claim 22 is applied to the hair

25. Use of an optionally quaternized or protonated condensation polymer having at least one heterocyclic end-group connected to the polymer backbone through a unit derived from an alkylamide, the connection comprising an optionally substituted ethylene group as conditioning agent, strengthening agent, film forming agent, surfactant, anti-static agent, moisturizer, emulsifier or hair styling agent.