Polydiene rubbers with functionalized end groups

Patent metadata

Field	Value
Publication number	US-12565550-B2
Application number	US-202117796155-A
Country	US
Kind code	B2
Filing date	Mar 24, 2021
Priority date	Mar 26, 2020
Publication date	Mar 3, 2026
Grant date	Mar 3, 2026

Abstract

An end-group functionalized polymer having one or more end groups according to the general formula (I)

wherein

R1 represents a saturated or unsaturated, linear or branched, preferably aliphatic, hydrocarbon group having from 1 to 20 carbon atoms which, in addition to C and H, may contain one or more heteroatoms, preferably independently of one another selected from O, N, S or Si;

R2, R3 are identical or different and represent saturated or unsaturated hydrocarbon groups having from 1 to 20 carbon atoms and wherein the hydrocarbon group may contain, in addition to C and H atoms, one or more heteroatoms, preferably selected from the group consisting of O, N, S and Si;

A represents a residue selected from the group consisting of O-R4-OH, R5-OH and R6-NH-R7, preferably O-R4-OH wherein R4, R5 and R6 represent a saturated or unsaturated linear or branched hydrocarbon group which, in addition to C and H atoms, may contain one or more heteroatoms, independently selected from O, N, S or Si and which contains from 1 to 20 carbon atoms and wherein

R7 represents H or a linear or branched or cyclic aliphatic or aromatic hydrocarbon group having from 1 to 20 carbon atoms and which, in addition to C and H atoms, may contain one or more heteroatoms, preferably selected from O, N, S or Si;

and wherein the polymer is a homopolymer of a conjugated diene or a copolymer of at least one or more conjugated diene and one or more vinylaromatic monomer and, optionally one or more other comonomers. Also provided are a process for making the polymers and articles made with the polymers.

First claim

The invention claimed is:

1 . An end-group functionalized polymer having one or more end groups according to the general formula (I)

wherein
R1 represents a saturated or unsaturated, linear or branched, hydrocarbon group having from 1 to 20 carbon atoms which, in addition to C and H, may contain one or more heteroatoms;
R2, R3 are identical or different and represent saturated or unsaturated hydrocarbon groups having from 1 to 20 carbon atoms and wherein the hydrocarbon group may contain, in addition to C and H atoms, one or more heteroatoms;
A represents a residue selected from the group consisting of O-R4-OH, R5-OH; R6-NH-R7;
R4, R5 and R6 represent independently from each other a saturated or unsaturated linear or branched hydrocarbon group which, in addition to C and H atoms, may contain one or more heteroatoms, independently selected from O, N, S or Si and which contains from 1 to 20 carbon atoms;
R7 represents H or a linear or branched or cyclic aliphatic or aromatic hydrocarbon group having from 1 to 20 carbon atoms and which, in addition to C and H atoms, may contain one or more heteroatoms, and wherein the polymer is a homopolymer of a conjugated diene or a copolymer of a conjugated diene.

2 . The polymer according to claim 1 , wherein the conjugated diene is selected from 1,3-butadiene, isoprene, 1,3-pentadiene, 2,3-dimethylbutadiene, 1-phenyl-1, 3-butadiene and a combination thereof.

3 . The polymer according claim 1 , wherein the polymer is selected from homopolymers of 1,3-butadiene and copolymers 1,3-butadiene with one or more vinylaromatic monomer and one or more optional comonomers and wherein the vinylaromatic monomer is selected from the group consisting of styrene, orthomethylstyrene, meta-methylstyrene, para-methylstyrene, para-tert-butylstyrene, vinylnaphthalene, divinylbenzene, trivinylbenzene, divinylnaphthalene and combinations thereof.

4 . The polymer according to claim 1 , wherein the polymer is selected from homopolymers of 1,3-butadiene and copolymers of 1,3-butadiene and styrene and one or more optional comonomers.

5 . The polymer according to claim 1 , wherein R1 corresponds to the general formula (IIa):
—[CHX 1 ] o —[CHX 2 ]—[O] z —[CHX 3 ] q —  (IIa)
wherein: z is 1 or 0, o, p and q are independently selected from 0, 1 and 2 with the proviso that at least one of o, p and q is not 0, X 1 , X 2 and X 3 are independently selected from H, from linear or branched alkyl, alkylaryl and aryl groups having from 1 to 12 carbon atoms, and from aminoalkyl groups N-R wherein R is a linear or branched or cyclic alkyl or alkylaryl residue having from 1 to 12 carbon atoms, and from X 1 and X 2 forming together a carbon-carbon bond to provide an unsaturation in the carbon chain, and wherein o, p, q, X 1 , X 2 and X 3 are selected such that the total number of carbon atoms is not more than 20.

6 . The polymer according to claim 1 , wherein R2, R3 are identical or different and are selected from methyl, ethyl, propyl, phenyl, benzyl, and trialkylsilyl wherein each alkyl group of the trialkyl silyl may contain from 1 to 4 carbon atoms and wherein the phenyl and benzyl may contain one or more substituents.

7 . The polymer according to claim 1 , wherein R4, R5 and R6 are selected from the group consisting of unsubstituted alkylene groups corresponding to the general formula —[CH 2 ] n — with n being an integer from 1 to 5, and substituted alkylene groups wherein at least one hydrogen atom of the —[CH 2 ] n — unit has been replaced by an alkyl, aryl, alkaryl or aralkyl group with the proviso that total number of carbon atoms is not more than 20.

8 . The polymer according to claim 1 , wherein R7 is selected from H, methyl, ethyl, propyl, butyl, phenyl, cyclohexyl, 2-phenylethyl, phenylmethyl, and trialkylsilyl.

9 . The polymer according to claim 1 , wherein R1 is —CH 2 CH 2 — and R2 and R3 are selected from the group consisting of methyl and ethyl.

10 . A compound comprising the polymer according to claim 1 , and at least one filler, and wherein the compound can be vulcanized.

11 . A method of making a compound according to claim 10 comprising mixing the polymer according to claim 1 and at least one filler.

12 . An article comprising a composition obtained by vulcanizing the compound according to claim 10 , wherein the article is selected from the group consisting of: tires, components of a tire, cable sheaths, hoses, drive belts, conveyor belts, roll linings, shoe soles, sealing rings and damping elements.

Assignees

• Arlanxeo Deutschland Gmbh

Inventors

• Ruenzi Thomas
• Steinhauser Norbert
• Wuest Kilian

Classifications

• C08F136/04

  conjugated · CPC title

• C08C19/22

  Incorporating nitrogen atoms into the molecule · CPC title

• C08F36/04

  conjugated · CPC title

• C08K5/3442

  having two nitrogen atoms in the ring · CPC title

• C08F136/08

  Isoprene · CPC title