Functionalized polymers

Patent metadata

Field	Value
Publication number	US-11865374-B2
Application number	US-201816763009-A
Country	US
Kind code	B2
Filing date	Nov 2, 2018
Priority date	Nov 15, 2017
Publication date	Jan 9, 2024
Grant date	Jan 9, 2024

Abstract

The invention relates to functionalized polymers, a process for producing functionalized polymers and the use of functionalized polymers, especially in the field of personal care.

First claim

The invention claimed is:

1. A polymer, comprising: monomeric units of general formula (I)

wherein
R 1 =independently from each other selected from the group consisting of alkyl radicals and alkenyl radicals, which both may be branched or straight chained, unsubstituted or substituted,
R 2 =independently from each other selected from the group consisting of hydroxyl substituted hydrocarbyl radicals,
R 3 and R 4 independently from each other selected from the group consisting of H and methyl, and
with the monomeric units of general formula (I) making up at least 90 wt.-%, of the total weight of the polymer,
with at least 90 wt.-% of all R 1 are selected from the group of alkyl and alkenyl radicals with from 6 to 32, carbon atoms, with the wt.-% referring to the sum of all R 1 present in the polymer, and
with the weight ratio of the sum of all R 2 -bearing-units to the sum of all R 1 -bearing-units being in the range of from 1:100 to 1:0.5,
wherein the polymer has a number average molecular weight M n in the range of from 2,000 to 8,100 g/mol,
wherein the polymer has a weight average molecular weight M w in the range of from 12,000 to 250,000 g/mol, and
wherein the M n and M w are selected such that the polymer has a ratio of weight average molecular weight M w to number average molecular weight M n in the range of from 0.1 to 3.6.

2. The polymer according to claim 1 , wherein the polymer has a melting point in the range of from 41° C. to 69° C.

3. The polymer of claim 1 , wherein the polymer has a ratio of weight average molecular weight Mw to number average molecular weight M n in the range of from 2.3 to 3.3.

4. The polymer of claim 1 , wherein
R 1 =independently from each other selected from the group consisting of stearyl and behenyl,
R 2 =2-Hydroxyethyl, and
R 3 and R 4 =H.

5. A process for preparing a polymer of claim 1 , comprising:
A) providing a monomer (1) of general formula (II) and a monomer (2) of general formula (III)

with
R 1A =independently from each other selected from the group consisting of alkyl radicals and alkenyl radicals, which both may be branched or straight chained, unsubstituted or substituted, R 2A =independently from each other selected from the group consisting of hydroxyl substituted hydrocarbyl radicals,
R 3A and R 4A =independently from each other selected from the group consisting of H and methyl, and
with
at least 90 wt.-% of all R 1A are selected from the group of alkyl and alkenyl radicals with from 6 to 32, carbon atoms, with the wt.-% referring to the sum of all R 1A present in the polymer, and a weight ratio of monomer (1) to monomer (2) in the range of from 1:100 to 1:0.5,
B) addition of at least one initiator to polymerize the monomers and performing a radical polymerization, optionally
C) removal of excess of monomers, and, optionally,
D) purification of the obtained polymer, wherein the initiator is added in an amount of from 5 to 20,000 ppm, wherein the ppm refers to the total weight of the sum of all monomers (1) and (2) provided in process step A).

6. The process according to claim 5 , wherein the initiator is selected from the group consisting of 2,2′-azo-bis(2-methyl propionitrile), 2,2′-azodi(2-methylbutyronitrile), 1,1′-azodi(hexahydrobenzonitrile), 4,4′-azo-bis(4-cyanovaleric acid), 2,2′-azo-bis(2,4-dimethyl valeronitrile), and 2,2′-azo-bis(2-cyclopropyl propionitrile), 2,2′-azo-bis(2-cyclobutyl propionitrile), 2,2′-azo-bis(2-cyclobutyl propionitrile), 2,2′-azo-bis(2,4-dimethyl valeronitrile), 1,1 ‘-azo-bis(1-cycloheptanenitrile), 2,2’-azo-bis(methylheptylonitrile), 2,2′-azo-bis(2-cyclohexyl propionitrile), azo-bisisobutyramidine 2HCl, phenyl-azo-triphenylmethane, 4-hydroxyphenyl-azo-triphenylmethane, peroxide and peroxy compounds, such as benzoyl peroxide, tert-butyl peroxy pivalate, tert-amyl peroxypivalate, acetyl peroxide, propionyl peroxide, 2-isopropionyl peroxide, butyryl peroxide, diisobutyryl peroxide, dilauroyl peroxide, didecanoyl peroxide, cumyl peroxyneodecanoate, 1,1,3,3-tetramethylbutyl peroxyneodecanoate, tert-butyl peroxydiethylacetate, tert-amyl peroxy-2-ethylhexanoate, tertamyl peroxy-2-ethylhexanoate, 2-methoxybenzoyl peroxide, cumyl peroxyneoheptanoate, tert-amyl peroxyneodecanoate, tert-butyl peroxyneodecanoate, tert-butyl peroxyneoheptanoate, tert-amyl peroxyacetate, 4 -benzylidenebutyryl peroxide, methyl phtholoyl peroxide, 1,1-di(tert-amylperoxy)cyclohexane, 3,6,9-triethyl-3,6,9-trimethyl -1,4,7-triperoxonane, isopropylcumyl hydroperoxide, 1,1,3,3-tetramethylbutyl hydroperoxide, cumyl hydroperoxide, tert-butyl hydroperoxide, tert-amyl hydroperoxide, diethyl peroxydicarbonate, tert-butylperoxy isopropyl carbonate, tert-butylperoxy 2-ethylhexyl carbonate, di-sec-butyl peroxydicarbonate, diisopropyl peroxydicarbonate, di(4-tert-butylcyclohexyl) peroxydicarbonate, di(2-ethylhexyl) peroxydicarbonate, dicetyl peroxydicarbonate, dimyristyl peroxydicarbonate, tert-amylperoxy 2-ethylhexyl carbonate, tert-butylperoxy isopropyl carbonate, tertbutyl peroxy 2-ethylhexyl carbonate, ethyltert-butyl peroxalate, benzyl (tert-butyl peroxy) oxalate, tertiary-butyl-N-(3-tolylperoxy) carbamate, potassium persulfate and mixtures thereof.

7. The process according to claim 5 , wherein in step B) at least one chain transfer agent is present, in an amount such that the weight ratio of added initiator and chain transfer agent is in the range of from 1:20 to 1:0.1.

8. The process according to claim 7 , wherein the chain transfer agent is selected from the group consisting of tetrachloromethane, bromotrichloromethane, isooctyl 3-mercaptopropionate, 4-methylbenzenethiol, tert-nonyl mercaptan, pentaerythritol tetrakis(2-mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), 4,4′-thiobisbenzenethiol, trimethylolpropane tris(3-mercaptopropionate), 1,8-dimercapto-3,6-dioxaoctane, n-dodecanethiol, ethyl mercaptan, mercaptoethanol, mercaptopropanol, mercaptobutanol, mercaptohexanol, mercaptooctanol, propanethiol, dithiothreitol, cysteine, homocysteine, glutathione, tertdodecanethiol, thioglycolic acid, dimercaptosuccinic, 2,3-dimercapto-1-propanesulfonic acid, acetylcysteine and thiophenol.

9. The process according to claim 5 , wherein no chain transfer agent is present in the process.

10. The polymer obtained by the process of claim 5 .

11. A personal care formulation containing the polymer of claim 1 .

12. A film comprising the polymer of claim 1 .

13. A fragrance comprising the polymer of claim 1 .

14. An emulsion comprising the polymer of claim 1 .

15. A dispersion for solid pigments comprising the polymer of claim 1 .

16. The polymer according to claim 1 , wherein
R 1 =independently from each other selected from the group consisting of alkyl radicals and alkenyl radicals, which both may be branched or straight chained substituted by hydroxyl-groups,
R 2 =independently from each other selected from the group consisting of alkyl radicals with from 1 to 10 carbon atoms,
R 3 and R 4 =H, and
with the monomeric units of general formula (I) making up for at least 95 wt.-% of the total weight of the polymer,
with at least 90 wt.-% of all R 1 are selected from the group of alkyl and alkenyl radicals with from 10 to 26 carbon atoms, with the wt.-% referring to the s

Assignees

• Evonik Operations Gmbh
• Evonik Corp

Inventors

• Amajjahe Sadik
• Mentel Matthias
• Meyer Juergen
• Wang Andrew Wilson
• Fonseca Arnoldo

Classifications

• A61Q5/00 Primary

  Preparations for care of the hair · CPC title

• A61K8/8152 Primary

  Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers · CPC title

• A61Q1/02

  Preparations containing skin colorants, e.g. pigments (preparations in powder form A61Q1/12) · CPC title

• A61Q1/06

  Lipsticks · CPC title

• A61Q9/02

  Shaving preparations · CPC title