Polymer comprising certain level of bio-based carbon

Patent metadata

Field	Value
Publication number	US-11384186-B2
Application number	US-201716468641-A
Country	US
Kind code	B2
Filing date	Dec 4, 2017
Priority date	Dec 12, 2016
Publication date	Jul 12, 2022
Grant date	Jul 12, 2022

Abstract

The present invention relates to a polymer comprising: (a) from 90 mol-% to 99.9 mol-%, of repeating units according to Formula (1) wherein at least 10 wt.-% of the repeating units according to Formula (1) comprise from 28 wt.-% to 100 wt.-% bio-based carbon content, relative to the total mass of carbon in the repeating unit according to Formula (1), measured according to standard ASTM D6866-12, Method B;and (b) from 0.01 mol-% to 10 mol-% of crosslinking or branching units, wherein the crosslinking or branching units result from the incorporation of a monomer comprising at least two olefinically unsaturated double bonds.

First claim

The invention claimed is:

1. A polymer comprising:
(a) from 90 mol-% to 99.9 mol-% of repeating units according to Formula (1), wherein at least 10 wt.-% of the repeating units according to Formula (1) comprise from 28 wt.-% to 100 wt.-% bio-based carbon content, relative to the total mass of carbon in the repeating unit according to Formula (1), measured according to standard ASTM D6866-12, Method B, calculated by multiplying percent modern carbon value, as determined by measuring carbon-14 content relative to total carbon content, by a correction factor of 0.95;

wherein:
R 1 and R 2 are independently selected from group consisting of H, methyl and ethyl; A is a linear or branched C 1 -C 12 -alkyl group; and Q + is H + , NH 4 + , organic ammonium ions [NHR 5 R 6 R 7 ] + wherein R 5 , R 6 , and R 7 independently of one another may be hydrogen, a linear or branched alkyl group having 1 to 22 carbon atoms, a linear or branched, singularly or multiply unsaturated alkenyl group having 2 to 22 carbon atoms, a C 6 -C 22 alkylamidopropyl group, a linear mono-hydroxyalkyl group having 2 to carbon atoms or a linear or branched dihydroxyalkyl group having 3 to carbon atoms, and where at least one of the radicals R 5 , R 6 , and R 7 is not hydrogen, or Q + is Li + , Na + , K + , ½ Ca ++ , ½ Mg ++ , ½ Zn ++ , ⅓ Al +++ , or combinations thereof; and

(b) from 0.01 mol-% to 10 mol-% of crosslinking or branching units, wherein the crosslinking or branching units result from the incorporation of a monomer comprising at least two olefinically unsaturated double bonds.

2. The polymer according to claim 1 , wherein at least 25 wt.-% of the repeating units (a) according to Formula (1) comprise from 28 wt.-% to 100 wt.-% bio-based carbon content, relative to the total mass of carbon in the repeating unit according to Formula (1), measured according to standard ASTM D6866-12, Method B, calculated by multiplying percent modern carbon value, as determined by measuring carbon-14 content relative to total carbon content, by a correction factor of 0.95.

3. The polymer according to claim 1 , any of claims 1 to 2 , wherein the repeating unit (a) according to Formula (1) comprises from 35 wt.-% bio-based carbon content, relative to the total mass of carbon in the repeating unit (a) according to Formula (1), measured according to standard ASTM D6866-12, Method B, calculated by multiplying percent modern carbon value, as determined by measuring carbon-14 content relative to total carbon content, by a correction factor of 0.95.

4. The polymer according to claim 1 , wherein the repeating units (a) according to Formula (1) have a degree of neutralisation of from 50.0 to 100 mol-%.

5. The polymer according to claim 1 , wherein the polymer comprises at least one repeating unit (a) according to Formula (1), wherein R 1 and R 2 are independently selected from the group consisting of H, methyl and ethyl; A is a linear or branched C 1 -C 12 -alkyl group; and Q + is H + , Li + , Na + , K + , ½ Ca ++ , ½ Mg ++ , ½ Zn ++ , ⅓ Al +++ , or combinations thereof.

6. The polymer according to claim 1 , wherein the polymer comprises from 95 mol-% to 99.9 mol-% of repeating units (a) according to Formula (1).

7. The polymer according to claim 1 , wherein the repeating units (a) according to Formula (1) result from the incorporation of a monomer selected from the group consisting of acryloyldimethyltaurates, acryloyl-1,1-dimethyl-2-methyltaurates, acryloyltaurates, acryloyl-N-methyltaurates, and combinations thereof.

8. The polymer according to claim 7 , wherein the acryloyldimethyltaurate comprises from 35 wt.-% bio-based carbon content, relative to the total mass of carbon in the acryloyldimethyltaurate, measured according to standard ASTM D6866-12, Method B, calculated by multiplying percent modern carbon value, as determined by measuring carbon-14 content relative to total carbon content, by a correction factor of 0.95.

9. The polymer according to claim 1 , wherein the crosslinking or branching units result from the incorporation of a monomer according to Formula (4)

wherein
R 1 is independently selected from the group consisting of H, methyl and ethyl; and
R 2 is a linear or branched alkyl group having 1 to 6 carbon atoms, or is a linear or branched, mono- or polyunsaturated alkylene group having 2 to 6 carbon atoms;
D, E, and F are independently methyleneoxy(—CH 2 O), ethyleneoxy(—CH 2 —CH 2 —O—), propyleneoxy(—CH(CH 3 )—CH 2 —O—), a linear or branched alkylene group having 1 to 6 carbon atoms, a linear or branched, singularly or multiply unsaturated alkenylene group having 2 to 6 carbon atoms, a linear mono-hydroxyalkylene group having 2 to 6 carbon atoms or a linear or branched dihydroxyalkylene group having 3 to 6 carbon atoms; and
o, p, and q each independently are an integer from 1 to 50.

10. The polymer according to claim 1 , wherein the crosslinking or branching units (b) result from the incorporation of a crosslinker selected from the group consisting of trimethylolpropane triacrylatee (TMPTA), glycerol propoxylate triacrylate (GPTA), and mixtures thereof.

11. The polymer according to claim 1 , wherein the polymer consists of:
(a) from 90 mol-% to 99.9 mol-% repeating units according to Formula (1) wherein at least 10 wt.-% of the repeating units according to Formula (1) comprise from 28 wt.-% to 100 wt.-% bio-based carbon content, relative to the total mass of carbon in the repeating unit according to Formula (1), measured according to standard ASTM D6866-12, Method B, calculated by multiplying percent modern carbon value, as determined by measuring carbon-14 content relative to total carbon content, by a correction factor of 0.95;

wherein:

R 1 and R 2 are independently selected from the group consisting of H, methyl and ethyl; A is a linear or branched C 1 -C 12 -alkyl group; and Q + is H + , NH 4 + , organic ammonium ions [NHR 5 R 6 R 7 ] + wherein R 5 , R 6 , and R 7 independently of one another may be hydrogen, a linear or branched alkyl group having 1 to 22 carbon atoms, a linear or branched, singularly or multiply unsaturated alkenyl group having 2 to 22 carbon atoms, a C 6 -C 22 alkylamidopropyl group, a linear mono-hydroxyalkyl group having 2 to carbon atoms or a linear or branched dihydroxyalkyl group having 3 to carbon atoms, and where at least one of the radicals R 5 , R 6 , and R 7 is not hydrogen, or Q + is Li + , Na + , K + , ½ Ca ++ , ½ Mg ++ , ½ Zn ++ , ⅓ Al +++ , or combinations thereof; and
(b) from 0.01 mol-% to 10 mol-% crosslinking or branching units, wherein the crosslinking or branching units result from the incorporation of a monomer comprising at least two olefinically unsaturated double bonds.

12. The polymer according to claim 1 , wherein the polymer has a weight average molecular weight of at least 700 g/mol.

13. The polymer according to claim 1 , wherein at least 20 wt.-% of the repeating units (a) according to Formula (1) comprise from 35 wt.-% bio-based carbon content, relative to the total mass of carbon in the repeating unit (a) according to Formula (1), measured according to standard ASTM D6866-12, Method B, calculated by multiplying percent modern carbon value, as determined by measuring carbon-14 co

Assignees

• Clariant Int Ltd

Inventors

• Fischer Dirk
• Kayser Christoph
• Starkulla Gundula

Classifications

• A61K8/922

  of vegetable origin · CPC title

• C08F2810/50

  wherein the polymer is a copolymer and the modification is taking place only on one or more of the monomers present in minority · CPC title

• C08F2800/10

  as molar percentages · CPC title

• A61Q19/08

  Anti-ageing preparations · CPC title

• C08F220/585 Primary

  and containing other heteroatoms, e.g. 2-acrylamido-2-methylpropane sulfonic acid [AMPS] · CPC title