Use of an esterified aromatic polyphenol derivative for the production of a phenol-aldehyde resin for reinforcement of a rubber composition
US-2019077952-A1 · Mar 14, 2019 · US
US10544298B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-10544298-B2 |
| Application number | US-201615545195-A |
| Country | US |
| Kind code | B2 |
| Filing date | Jan 20, 2016 |
| Priority date | Jan 21, 2015 |
| Publication date | Jan 28, 2020 |
| Grant date | Jan 28, 2020 |
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A rubber composition comprises at least one phenol/aldehyde resin based on at least one aromatic polyphenol comprising at least one aromatic ring bearing at least two hydroxyl functions in the meta position relative to one another, the two positions ortho to at least one of the hydroxyl functions being unsubstituted, and at least one aromatic polyaldehyde selected from 1,3-benzenedicarboxaldehyde, 1,4-benzenedicarboxaldehyde and mixtures of these compounds, the rubber composition having a nominal secant modulus at 10% elongation, measured according to standard ASTM D 412, 1998, of greater than or equal to 25 MPa.
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The invention claimed is: 1. A rubber composition comprising at least one phenol/aldehyde resin based on: at least one aromatic polyphenol comprising at least one aromatic ring bearing at least two hydroxyl functions in the meta position relative to one another, the two positions ortho to at least one of the hydroxyl functions being unsubstituted; and at least one aromatic polyaldehyde selected from 1,3-benzenedicarboxaldehyde, 1,4-benzenedicarboxaldehyde and mixtures thereof, wherein the rubber composition has a nominal secant modulus at 10% elongation, measured according to standard ASTM D 412, 1998, of greater than or equal to 25 MPa; and wherein the rubber composition comprises from 30 to 90 phr total reinforcing filler. 2. The rubber composition according to claim 1 , wherein at least one aromatic ring bears three hydroxyl functions in the meta position relative to one another. 3. The rubber composition according to claim 1 , wherein the two positions ortho to each hydroxyl function are unsubstituted. 4. The rubber composition according to claim 1 , wherein the remainder of the at least one aromatic ring is unsubstituted. 5. The rubber composition according to claim 1 , wherein at least one aromatic polyphenol comprises several aromatic rings, at least two of these each bearing at least two hydroxyl functions in the meta position relative to one another, the two positions ortho to at least one of the hydroxyl functions of at least one aromatic ring being unsubstituted. 6. The rubber composition according to claim 5 , wherein at least one of the aromatic rings of the at least one aromatic polyphenol bears three hydroxyl functions in the meta position relative to one another. 7. The rubber composition according to claim 5 , wherein the two positions ortho to each hydroxyl function of at least one aromatic ring are unsubstituted. 8. The rubber composition according to claim 5 , wherein the two positions ortho to each hydroxyl function of each aromatic ring are unsubstituted. 9. The rubber composition according to claim 1 , wherein at least one, or each, aromatic ring of the at least one aromatic polyphenol is a benzene ring. 10. The rubber composition according to claim 1 , wherein the at least one aromatic polyphenol is selected from the group consisting of resorcinol, phloroglucinol, 2,2′,4,4′-tetrahydroxydiphenyl sulphide, 2,2′,4,4′-tetrahydroxybenzophenone, resins pre-condensed from at least one of these phenols, and mixtures thereof. 11. The rubber composition according to claim 1 , wherein the at least one aromatic polyaldehyde is 1,4-benzenedicarboxaldehyde. 12. The rubber composition according to claim 1 further comprising a diene elastomer selected from the group consisting of polybutadienes, synthetic polyisoprenes, natural rubber, butadiene copolymers, isoprene copolymers, and mixtures thereof. 13. The rubber composition according to claim 1 , wherein the rubber composition has a nominal secant modulus at 10% elongation, measured according to standard ASTM D 412, 1998, of greater than or equal to 30 MPa. 14. The rubber composition according to claim 13 , wherein the rubber composition has a nominal secant modulus at 10% elongation, measured according to standard ASTM D 412, 1998, of greater than or equal to 35 MPa. 15. The rubber composition according to claim 14 , wherein the rubber composition has a nominal secant modulus at 10% elongation, measured according to standard ASTM D 412, 1998, of greater than 39 MPa. 16. A rubber composite reinforced with at least one reinforcing element embedded in a rubber composition, wherein the rubber composition is a rubber composition according to claim 1 . 17. A tire comprising a rubber composition according to claim 1 . 18. A method for manufacturing a rubber composition comprising the step of: mixing at least one elastomer, at least one aromatic polyphenol comprising at least one aromatic ring bearing at least two hydroxyl functions in the meta position relative to one another, the two positions ortho to at least one of the hydroxyl functions being unsubstituted, and at least one aromatic polyaldehyde selected from 1,3-benzenedicarboxaldehyde, 1,4-benzenedicarboxaldehyde and mixtures thereof, wherein the rubber composition has a nominal secant modulus at 10% elongation, measured according to standard ASTM D 412, 1998, of greater than or equal to 25 MPa. 19. The method according to claim 18 , in which the at least one elastomer is a diene elastomer, further comprising the steps of: incorporating, in the diene elastomer, during a first step, a reinforcing filler, to make a mixture and kneading the mixture thermomechanically until a maximum temperature of between 110° C. and 190° C. is reached; cooling the mixture to a temperature of less than 100° C.; then incorporating, during a second step, a crosslinking system, the at least one aromatic polyphenol and the at least one aromatic polyaldehyde; and kneading the mixture up to a maximum temperature of less than 110° C.
Processes for mixing polymers · CPC title
Compositions of homopolymers or copolymers of conjugated diene hydrocarbons · CPC title
Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition · CPC title
Phenols; Phenolates · CPC title
Crosslinking, e.g. vulcanising, of macromolecules (mechanical aspects B29C35/00; crosslinking agents C08K) · CPC title
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