Rubber composition containing main-chain benzoxazine, and preparation method therefor

Patent metadata

Field	Value
Publication number	US-10538648-B2
Application number	US-201615736432-A
Country	US
Kind code	B2
Filing date	Jun 16, 2016
Priority date	Jun 16, 2015
Publication date	Jan 21, 2020
Grant date	Jan 21, 2020

Abstract

Disclosed is a rubber composition containing main-chain benzoxazine, in which benzoxazine generates no harmful materials during vulcanization and can thus be used in lieu of a phenol novolac resin used as a resin component of a conventional rubber composition, and also in which the use of benzoxazine, especially main-chain benzoxazine having a high molecular weight, is capable of maintaining excellent mechanical properties and exhibiting high flexibility. The rubber composition of the invention can be utilized for a rubber product, especially a tire product.

First claim

The invention claimed is:

1. A rubber composition comprising
a raw rubber and
a polymer comprising a benzoxazine ring in its main chain (main-chain benzoxazine).

2. The rubber composition of claim 1 , wherein the main-chain benzoxazine has a weight average molecular weight of 500 g/mol to 10,000 g/mol.

3. The rubber composition of claim 1 , wherein the main-chain benzoxazine is represented by Chemical Formula 1 or 2 below:

in Chemical Formula 1, n=1-10 and in Chemical Formula 2, n=1-10.

4. The rubber composition of claim 1 , wherein the main-chain benzoxazine is prepared by reacting a diphenol compound, an amine compound, and an aldehyde compound.

5. The rubber composition of claim 4 , wherein the diphenol compound is at least one selected from the group consisting of bisphenol A (2,2-bis(4-hydroxyphenyl)propane, BPA), bisphenol AP (1,1-bis(4-hydroxyphenyl)-1-phenyl-ethane), bisphenol AF (2,2-bis(4-hydroxyphenyl)hexafluoropropane), bisphenol B (2,2-bis(4-hydroxyphenyl)butane), bisphenol BP (bis-(4-hydroxyphenyl)diphenylmethane), bisphenol C (2,2-bis(3-methyl-4-hydroxyphenyl)propane), (bis(4-hydroxyphenyl)-2,2-dichloroethylene), bisphenol E (1,1-bis(4-hydroxyphenyl)ethane), bisphenol F (bis(4-hydroxyphenyl)methane), bisphenol G (2,2-bis(4-hydroxy-3-isopropyl-phenyl)propane), bisphenol M (1,3-bis(2-(4-hydroxyphenyl)-2-propyl)benzene), bisphenol S (bis(4-hydroxyphenyl)sulfone), bisphenol P (1,4-bis(2-(4-hydroxyphenyl)-2-propyl)benzene), bisphenol PH (5,5′-(1-methylethyliden)-bis[1,1′-(bisphenyl)-2-ol]propane), bisphenol TMC (1,1-bis(4-hydroxyphenyl)-3,3,5-trimethyl-cyclohexane), and bisphenol Z (1,1-bis(4-hydroxyphenyl)-cyclohexane).

6. The rubber composition of claim 4 , wherein the amine compound is monoamine or diamine.

7. The rubber composition of claim 6 , wherein the monoamine is at least one selected from the group consisting of ethanolamine, allylamine, methylamine, ethylamine, propylamine, butylamine, isopropylamine, hexylamine, octadecylamine, cyclohexylamine, 2-aminofluorene and aniline.

8. The rubber composition of claim 6 , wherein the diamine is at least one selected from the group consisting of diamino diphenyl methane, o-phenylene diamine, m-phenylene diamine, p-phenylene diamine, benzidine, furfurylamine, 1,4-diaminobenzene, 2-aminobenzylamine, 4,4′-methylenedianiline, 4,4′-diaminodiphenylether, 4,4′-diaminodiphenylsulfone, 4,4′-diaminophenylsulfide and 4,4′-oxydianiline; alicyclic diamine, including 1,4-diaminocyclohexane; and 1,2-diaminoethane, 1,3-diaminopropane, 1,4-diaminobutane, 1,6-diaminohexane, 1,10-diaminodecane, 1,12-diaminododecane, 1,14-diaminotetradecane and 1,18-diaminooctadecane.

9. The rubber composition of claim 4 , wherein the aldehyde compound is at least one selected from the group consisting of paraformaldehyde, formaldehyde, acetaldehyde, propionaldehyde, butylaldehyde and polyoxymethylene.

10. The rubber composition of claim 1 , wherein the main-chain benzoxazine is contained in an amount of 1 to 30 parts by weight based on 100 parts by weight of raw rubber.

11. The rubber composition of claim 10 , wherein the raw rubber comprises 100 parts by weight of styrene-butadiene rubber and 10 to 60 parts by weight of natural rubber.

12. The rubber composition of claim 1 , wherein the rubber composition includes zinc oxide, stearic acid, carbon black, processing oil, sulfur, and N-tert-butylbenzothiazole-2-sulfenamide (TBBS).

13. The rubber composition of claim 12 , wherein the rubber composition includes, based on 100 parts by weight of raw rubber, 1-10 parts by weight of zinc oxide, 0.5-5 parts by weight of stearic acid, 30-75 parts by weight of carbon black, 2-10 parts by weight of processing oil, 0.5-25 parts by weight of sulfur, and 0.2-10 parts by weight of N-tert-butylbenzothiazole-2-sulfenamide (TBBS).

Assignees

• Kolon Inc

Inventors

• Sung Do Kyung
• Park Ki Hyun

Classifications

• C08L19/00 Primary

  Compositions of rubbers not provided for in groups C08L7/00 - C08L17/00 · CPC title

• C08L21/00

  Compositions of unspecified rubbers · CPC title

• C08G73/06

  Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule · CPC title

• C08K2003/2296

  of zinc · CPC title

• C08L2205/035

  containing four or more polymers in a blend · CPC title