1-amino-3-(oxyalkylalkoxysilyl)-2-propanol-terminated diene rubbers

Patent metadata

Field	Value
Publication number	US-12371514-B2
Application number	US-202017628125-A
Country	US
Kind code	B2
Filing date	Jul 14, 2020
Priority date	Jul 16, 2019
Publication date	Jul 29, 2025
Grant date	Jul 29, 2025

Abstract

The invention concerns 1-amino-3-(oxyalkylalkoxysilyl)-2-propanol-terminated diene rubbers, their preparation and use.

First claim

The invention claimed is:

1. An 1-amino-3-(oxyalkylalkoxysilyl)-2-propanol-terminated polymer according to general formula (I),

wherein
the polymer contains at least one carbon-carbon double bond;
R 1 is selected from the group consisting of
(i) a —C 1 -C 24 -alkyl that is saturated or unsaturated and that is unsubstituted, mono- or polysubstituted;
(ii) a —C 1 -C 24 -heteroalkyl that is saturated or unsaturated and that is unsubstituted, mono- or polysubstituted;
(iii) a 6-24-membered aryl that is unsubstituted, mono- or polysubstituted;
(iv) a 5-24-membered heteroaryl that is unsubstituted, mono- or polysubstituted;
(v) a 3-24-membered cycloalkyl that is saturated or unsaturated and that is unsubstituted, mono- or polysubstituted; and
(vi) a 3-24-membered heterocycloalkyl that is saturated or unsaturated and is unsubstituted, mono- or polysubstituted;

R 2 is selected from the group consisting of
(i) a —C 1 -C 24 -alkyl, which is saturated or unsaturated, and which is unsubstituted, mono- or polysubstituted;
(ii) a —C 1 -C 24 -heteroalkyl, which is saturated or unsaturated, and which is unsubstituted, mono- or polysubstituted;
(iii) a 6-24-membered aryl, which is unsubstituted, mono- or polysubstituted;
(iv) a 5-24-membered heteroaryl, which is unsubstituted, mono- or polysubstituted;
(v) a 3-24-membered cycloalkyl, which is saturated or unsaturated, and which is unsubstituted, mono- or polysubstituted; and
(vi) a 3-24-membered heterocycloalkyl, which is saturated or unsaturated, and which is unsubstituted, mono- or polysubstituted;

R 3 is selected from the group consisting of
(i) a —C 1 -C 6 -alkylene- that is saturated or unsaturated and that is unsubstituted, mono- or polysubstituted;
(ii) a —C 1 -C 6 -heteroalkylene- that is saturated or unsaturated and that is unsubstituted, mono- or polysubstituted; and
(iii) a 6-14-membered arylene that is unsubstituted, mono- or polysubstituted;

R 4 is selected from the group consisting of
(i) a-C 1 -C 6 -alkylene- that is saturated or unsaturated and that is unsubstituted, mono- or polysubstituted;
(ii) a-C 1 -C 6 -heteroalkylene- that is saturated or unsaturated and that is unsubstituted, mono- or polysubstituted; and
(iii) a 6-14-membered arylene that is unsubstituted, mono- or polysubstituted;

R 5 is selected from the group consisting of
(i) a —C 1 -C 6 -alkyl that is saturated or unsaturated and that is unsubstituted, mono- or polysubstituted;
(ii) a —C 1 -C 6 -heteroalkyl that is saturated or unsaturated and that is unsubstituted, mono- or polysubstituted; and
(iii) a 6-14-membered aryl that is unsubstituted, mono- or polysubstituted;

R 6 is selected from the group consisting of
(i) a —C 1 -C 6 -alkyl that is saturated or unsaturated and that is unsubstituted, mono- or polysubstituted;
(ii) a —C 1 -C 6 -heteroalkyl that is saturated or unsaturated and that is unsubstituted, mono- or polysubstituted; and
(iii) a 6-14-membered aryl that is unsubstituted, mono- or polysubstituted;

wherein “mono- or polysubstituted” means substituted with one substituent in the case of “monosubstituted” or with more than one substituent in the case of “polysubstituted”, wherein the substituents independently of one another are selected from the group consisting of —F, —Cl, —Br, —I, —CN, ═O, —CF 3 , —CF 2 H, —CFH 2 , —CF 2 Cl, —CFCl 2 , —C 1 -C 18 -alkyl that is saturated or unsaturated, and —C 1 -C 18 -heteroalkyl that is saturated or unsaturated;
and
x+y=3 with 1≤x≤3 and 0≤y≤2.

2. The 1-amino-3-(oxyalkylalkoxysilyl)-2-propanol-terminated polymer according to claim 1 , wherein the polymer is a homopolymer or a copolymer of one or more conjugated dienes.

3. The 1-amino-3-(oxyalkylalkoxysilyl)-2-propanol-terminated polymer according to claim 1 , wherein the polymer is obtained by copolymerization of 1,3-butadiene with styrene; or isoprene with styrene.

4. The 1-amino-3-(oxyalkylalkoxysilyl)-2-propanol-terminated polymer according to claim 1 , wherein
R 1 is (i) —C 1 -C 6 -alkyl, which is saturated or unsaturated, and which is unsubstituted;
R 2 is (i) —C 1 -C 6 -alkyl, which is saturated or unsaturated, and which is unsubstituted;
R 3 is (i) —C 1 -C 6 -alkylene-, which is saturated or unsaturated, and which is unsubstituted;
R 4 is —C 1 -C 6 -alkylene-, which is saturated or unsaturated, and which is unsubstituted; and
R 5 is —C 1 -C 6 -alkyl, which is saturated or unsaturated, and which is unsubstituted and R 6 is —C 1 -C 6 -alkyl, which is saturated or unsaturated, and which is unsubstituted; x is 3 and y is 0.

5. The 1-amino-3-(oxyalkylalkoxysilyl)-2-propanol-terminated polymer according to claim 1 , wherein
the polymer is obtained by copolymerization of 1,3-butadiene with styrene;
R 1 is —C 1 -C 2 -alkyl, which is saturated or unsaturated, and which is unsubstituted;
R 2 is —C 1 -C 2 -alkyl, which is saturated or unsaturated, and which is unsubstituted;
R 3 is —C 1 -C 2 -alkylene-, which is saturated or unsaturated, and which is unsubstituted;
R 4 is —C 3 -alkylene-, which is saturated or unsaturated, and which is unsubstituted;
R 5 and R 6 independently of one another are —C 1 -C 2 -alkyl, which is saturated or unsaturated, and which is unsubstituted; and
x+y=3 with 1≤x≤3 and 0≤y≤2.

6. A method for manufacturing a 1-amino-3-(oxyalkylalkoxysilyl)-2-propanol-terminated polymer according to general formula (I),

comprising the following steps:
(a) providing a polymer intermediate containing at least one carbon-carbon double bond prepared by anionic diene polymerization or diene polymerization using a coordination catalyst;
(b) providing a cyclic urea derivative of the general formula (II)

(c) providing a glycidoxyalkylsilane of the general formula (III)

(d) adding the cyclic urea derivative of the general formula (II) to the polymer as a first functionalization reagent to form a functionalized polymer intermediate; and
(e) subsequently adding the glycidoxyalkylsilane of the general formula (III) to the functionalized polymer intermediate as a second functionalization reagent to form the 1-amino-3-(oxyalkylalkoxysilyl)-2-propanol-terminated polymer according to general formula (I);
wherein
R 1 is selected from the group consisting of
(i) a —C 1 -C 24 -alkyl that is saturated or unsaturated and that is unsubstituted, mono- or polysubstituted;
(ii) a —C 1 -C 24 -heteroalkyl that is saturated or unsaturated and that is unsubstituted, mono- or polysubstituted;
(iii) a 6-24-membered aryl that is unsubstituted, mono- or polysubstituted;
(iv) a 5-24-membered heteroaryl that is unsubstituted, mono- or polysubstituted;
(v) a 3-24-membered cycloalkyl that is saturated or unsaturated and that is unsubstituted, mono- or polysubstituted; and
(vi) a 3-24-membered heterocycloalkyl that is saturated or unsaturated and is unsubstituted, mono- or polysubstituted;

R 2 is selected from the group consisting of
(i) a —C 1 -C 24 -alkyl, which is saturated or unsaturated, and which is unsubstituted, mono- or polysubstituted;
(ii) a —C 1 -C 24 -heteroalkyl, which is saturated or unsaturated, and which is unsubstituted, mono- or polysubstituted;
(iii) a 6-24-membered aryl, which is unsubstituted, mono- or polysubstituted

Assignees

• Arlanxeo Deutschland Gmbh

Inventors

• Steinhauser Norbert

Classifications

• C08L9/06

  Copolymers with styrene · CPC title

• C08F236/10 Primary

  with vinyl-aromatic monomers · CPC title

• C08C19/22 Primary

  Incorporating nitrogen atoms into the molecule · CPC title

• C08F8/42

  Introducing metal atoms or metal-containing groups · CPC title

• C08F279/02

  on to polymers of conjugated dienes · CPC title