MODIFIED AND CONJUGATED DIENE-BASED POLYMER AND METHOD FOR PREPARING THEREOF

• US 20180162959A1
• Filed: 12/22/2016
• Published: 06/14/2018
• Est. Priority Date: 12/22/2015
• Status: Active Grant

• Current Assignee: LG Chem Limited (LG Corporation)
• Original Assignee: LG Chem Limited (LG Corporation)
• Inventors: Choi, Seung Ho, Kim, Ji Eun, Choi, Won Mun, Kim, Cheol Jae
• Granted Patent: US 10,604,591 B2
• Time in Patent Office: Days
• CPC Class Codes: B60C 1/00 Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
• CPC Class Codes: C07F 7/1804 Compounds having Si-O-C linkages Si-O-acyl linkages C07F7/1896
• CPC Class Codes: C08C 19/22 Incorporating nitrogen atoms into the molecule
• CPC Class Codes: C08C 19/25 Incorporating silicon atoms into the molecule
• CPC Class Codes: C08C 19/44 of polymers containing metal atoms exclusively at one or both ends of the skeleton
• CPC Class Codes: C08F 212/08 Styrene
• CPC Class Codes: C08F 236/06 Butadiene
• CPC Class Codes: C08F 236/10 with vinyl-aromatic monomers
• CPC Class Codes: C08F 36/04 conjugated
• CPC Class Codes: C08F 8/30 Introducing nitrogen atoms or nitrogen-containing groups
• CPC Class Codes: C08F 8/42 Introducing metal atoms or metal-containing groups
• CPC Class Codes: C08K 5/00 Use of organic ingredients
• CPC Class Codes: C08K 5/16 Nitrogen-containing compounds C08K5/0091 takes precedence
• CPC Class Codes: C08K 5/20 Carboxylic acid amides
• CPC Class Codes: C08K 5/54 Silicon-containing compounds C08K5/0091 takes precedence
• CPC Class Codes: C08K 5/5419 containing at least one Si—C bond
• CPC Class Codes: Y02T 10/86 Optimisation of rolling resistance, e.g. weight reduction

Abstract

The present invention provides a compound represented by Formula 1, a modified and conjugated diene-based polymer with a high modification ratio, which includes a functional group derived from the compound, a method for preparing the polymer, a rubber composition including the polymer, and a tire manufactured from the rubber composition.

Claims

1. A compound represented by the following Formula 1:

2. The compound of claim 1, wherein in Formula 1,

R¹ is selected from the group consisting of an alkyl group of 1 to 20 carbon atoms, a cycloalkyl group of 3 to 20 carbon atoms, an aryl group of 6 to 20 carbon atoms, an arylalkyl group of 7 to 20 carbon atoms, an alkoxy group of 1 to 20 carbon atoms, an alkoxyalkyl group of 2 to 20 carbon atoms, a phenoxyalkyl group of 7 to 20 carbon atoms, an aminoalkyl group of 1 to 20 carbon atoms, and —

[R¹¹O]_xR¹² (where R¹¹ is an alkylene group of 2 to 10 carbon atoms, R¹² is selected from the group consisting of a hydrogen atom, an alkyl group of 1 to 10 carbon atoms, a cycloalkyl group of 3 to 12 carbon atoms, an aryl group of 6 to 18 carbon atoms, and an arylalkyl group of 7 to 18 carbon atoms, and x is an integer of 2 to

     10).

3. The compound of claim 1, wherein in Formula 1,

R¹ is selected from the group consisting of an alkyl group of 1 to 10 carbon atoms, a cycloalkyl group of 3 to 12 carbon atoms, an aryl group of 6 to 12 carbon atoms, an arylalkyl group of 7 to 12 carbon atoms, an alkoxyalkyl group of 2 to 10 carbon atoms, a phenoxyalkyl group of 7 to 12 carbon atoms, an aminoalkyl group of 1 to 10 carbon atoms, and —

[R¹¹O]_xR¹² (where R¹¹ is an alkylene group of 2 to 10 carbon atoms, R¹² is selected from the group consisting of a hydrogen atom, an alkyl group of 1 to 10 carbon atoms, a cycloalkyl group of 3 to 12 carbon atoms, an aryl group of 6 to 18 carbon atoms, and an arylalkyl group of 7 to 18 carbon atoms, and x is an integer of 2 to

     10),

R² is an alkylene group of 1 to 6 carbon atoms,

R³ and R⁴ are each independently an alkyl group of 1 to 5 carbon atoms,

R⁵ is an alkyl group of 1 to 5 carbon atoms or a cycloalkyl group of 3 to 8 carbon atoms,

m is an integer of 0 to 2, and n is an integer of 1 or 2, provided that R¹ is an alkyl group of 1 to 10 carbon atoms, a cycloalkyl group of 3 to 10 carbon atoms, an aryl group of 6 to 12 carbon atoms, or an arylalkyl group of 7 to 12 carbon atoms, n is an integer of 2.

4. The compound of claim 1, wherein in Formula 1,

R¹ is one selected from the group consisting of an alkyl group of 1 to 10 carbon atoms, an alkoxyalkyl group of 2 to 10 carbon atoms and a phenoxyalkyl group of 7 to 12 carbon atoms,

R² is an alkylene group of 1 to 5 carbon atoms,

R³ and R⁴ are each independently an alkyl group of 1 to 5 carbon atoms,

m is an integer of 0 or 1, and n is an integer of 2.

5. The compound of claim 1, wherein the compound represented by Formula 1 is one selected from the group consisting of N,N-bis(3-triethoxysilyl)propyl)acetamide, N-methyl-N-(3-(trimethoxysilyl)propyl)acetamide, N,N-bis(3-(diethoxy(methyl)silyl)propyl)acetamide, and N-butyl-N-(3-(trimethoxysilyl)propyl)acetamide.

6. The compound of claim 1, wherein the compound is used as a modifier for modifying a conjugated diene-based polymer.

7. The compound of claim 6, wherein the conjugated diene-based polymer is a homopolymer comprising a derived unit of a conjugated diene-based monomer, or a copolymer comprising derived units of a conjugated diene-based monomer and an aromatic vinyl-based monomer.

8. A modified and conjugated diene-based polymer comprising a functional group derived from a compound represented by the following Formula 1:

9. The modified and conjugated diene-based polymer of claim 8, wherein the compound represented by Formula 1 is one selected from the group consisting of N,N-bis(3-triethoxysilyl) propyl) acetamide, N-methyl-N-(3-(trimethoxysilyl)propyl)acetamide, N,N-bis(3-(diethoxy(methyl)silyl)propyl)acetamide, and N-butyl-N-(3-(trimethoxysilyl)propyl)acetamide.

10. The modified and conjugated diene-based polymer of claim 8, wherein the conjugated diene-based polymer is a homopolymer comprising a derived unit of a conjugated diene-based monomer, or a copolymer comprising derived units of a conjugated diene-based monomer and an aromatic vinyl-based monomer.

11. The modified and conjugated diene-based polymer of claim 10, wherein the copolymer comprises 60 wt % or less of the derived unit of the aromatic vinyl-based monomer.

12. The modified and conjugated diene-based polymer of claim 8, wherein the polymer has a number average molecular weight of 1,000 g/mol to 2,000,000 g/mol.

13. The modified and conjugated diene-based polymer of claim 8, wherein the polymer has molecular weight distribution (Mw/Mn) of 1.05 to 10.

14. The modified and conjugated diene-based polymer of claim 8, wherein the polymer has a vinyl content of 5 wt % or more.

15. A method for preparing a modified and conjugated diene-based polymer of claim 8, the method comprising:

1) a step of polymerizing conjugated diene-based monomers, or an aromatic vinyl-based monomer and a conjugated diene-based monomer in the presence of an organometal compound in a hydrocarbon solvent to prepare an active polymer which is bonded to an organometal; and

2) a step of reacting the active polymer with a compound represented by the following Formula 1;

16. The method for preparing a modified and conjugated diene-based polymer of claim 15, wherein the organometal compound is used in an amount of 0.01 mmnol to 10 mmol based on total 100 g of the monomers.

17. The method for preparing a modified and conjugated diene-based polymer of claim 15, wherein the polymerizing of step 1) is conducted by further adding a polar additive.

18. The method for preparing a modified and conjugated diene-based polymer of claim 17, wherein the polar additive is used in an amount of 0.001 g to 10 g based on total 1 mmol of the organometal compound.

19. The method for preparing a modified and conjugated diene-based polymer of claim 15, wherein the compound represented by Formula 1 is one selected from the group consisting of N,N-bis(2-triethoxysilyl)propyl)acetamide, N-methyl-N-(3-(trimethoxysilyl)propyl)acetamide, N,N-bis(3-(diethoxy(methyl)silyl)propyl)acetamide, and N-butyl-N-(3-(trimethoxysilyl)propyl)acetamide.

20. The method for preparing a modified and conjugated diene-based polymer of claim 15, wherein the compound represented by Formula 1 is used in an amount of 0.1 mol to 10 mol based on 1 mol of the organometal compound.