Process for preparing compounds for tyres and tyres comprising them

Patent metadata

Field	Value
Publication number	US-2022010104-A1
Application number	US-201917296064-A
Country	US
Kind code	A1
Filing date	Nov 27, 2019
Priority date	Nov 28, 2018
Publication date	Jan 13, 2022
Grant date	—

Abstract

The present invention relates to a compound represented by the formula (II): CB-O-ROS-GC-Zn (II) where CB represents the white filler, O represents one or more oxygen bridge bonds, ROS represents an organo-silane residue, GC represents one or more coordinating groups forming a chelate with zinc in ionic form represented by linear, branched or cyclic alkyl chains, comprising one or more heteroatoms inside or at the end of the alkyl chain, and Zn represents zinc in ionic form coordinated with the coordinating groups, a process for the preparation thereof, and the use thereof in the vulcanisation process of elastomeric compounds.

First claim

1 . A compound represented by the following formula (II):
CB-O-ROS-GC-Zn  (II)
wherein CB represents the white filler, O represents one or more oxygen bridge bonds, ROS represents an organo-silane residue, GC represents one or more coordinating groups forming a chelate with zinc in ionic form, and Zn represents zinc in ionic form coordinated with the coordinating groups, wherein said coordinating groups GC are linear, branched or cyclic alkyl chains, comprising one or more heteroatoms inside or at the end of the alkyl chain.

2 . A process for the preparation of the compound of formula (II) as claimed in claim 1 , wherein said method comprises at least:
providing a white filler (CB) providing a coupling agent having the following formula (I):
GR-ROS-GC  (I)

wherein GR represents one or more reactive groups capable of forming oxygen bridges with the surface of said white filler, ROS represents an organo-silane residue, and GC represents one or more coordinating groups, providing a zinc compound (Zn 2+ ), reacting the white filler (CB) with one or more reactive groups (GR) of said compound of formula (I) so as to form oxygen bridges (—O—) between said white filler (CB) and said organo-silane residue (ROS), and reacting one or more coordinating groups (GC) of said compound of formula (I) with the zinc compound so as to form a chelate, and separating the resulting compound of formula (II) as claimed in claim 1 .

3 . The compound as claimed in claim 1 or the process as claimed in claim 2 , wherein said white filler is selected from the group consisting of silica and silicates in the form of fibres, lamellae or granules.

4 . The compound or process as claimed in claim 3 , wherein said white filler is selected from the group consisting of bentonite, nontronite, beidellite, volkonskoite, hectorite, saponite, sauconite, vermiculite, sericite, sepiolite, paligorskite also known as attapulgite, montmorillonite, alloisite and the like, possibly modified by acid treatment and/or derivatized, and mixtures thereof.

5 . The compound or process as claimed in claim 1 , wherein said coordinating groups GC are functional groups represented by the formula —C n H 2n —XC m H 2m —Y, where n and m, equal or different from each other, are an integer from 1 a 6 inclusive and Y and X, equal or different from each other, are a group selected from mercapto and amino.

6 . The process as claimed in claim 2 , wherein said GR reactive groups are alkoxy groups having 1 to 4 carbon atoms.

7 . The process as claimed in claim 2 , wherein said coupling agent is represented by the general formula (Ia):
(R) 3 Si—C n H 2n —X—C m H 2m —Y  (Ia)
wherein the R groups, equal to or different from each other, are selected from alkyl or alkoxy groups having 1 to 4 carbon atoms, provided that at least one of the R groups is an alkoxy group; n and m, equal or different from each other, are an integer from 1 to 6 inclusive; Y and X, equal or different from each other, are a group selected from mercapto and amino.

8 . The process as claimed in claim 2 , wherein said coupling agent is selected from the group consisting of (3-aminopropyl)triethoxysilane (APTES), N-(2-aminoethyl)-3-aminopropyl-trimethoxysilane (also known as N-[3-(trimethoxysilyl)propyl]ethylenediamine (EDTMS)), N-(2-aminoethyl)-3-aminopropyl-triethoxysilane, N-(2-aminoethyl)-3-aminopropyl-methyl-dimethoxysilane, 3-aminopropylmethyl-diethoxysilane, 3-ureidopropyl-trimethoxy silane, 3-ureidopropyl-triethoxysilane, N-cyclohexyl(aminomethyl) methyldiethoxy silane, N-cyclohexyl(aminomethyl) triethoxysilane, N-cyclohexyl-3-aminopropyl-trimethoxysilane, 3-(2-aminomethylamino)propyl-triethoxysilane, N-(n-butyl)-3-aminopropyltrimethoxy-silane, N-(2-aminoethyl)-3-aminopropylmethyldiethoxysilane, N-(2-aminoethyl)-3-aminoisobutyl-methyldimethoxysilane, 3-aminopropylmethyldimethoxysilane, 3-(2-(2-aminoethylamino)ethylamino)propyl-trimethoxysilane, N-(n-butyl)-3-aminopropyl-triethoxysilane, N, N-diethylaminopropyl-trimethoxysilane, N, N-dimethylaminopropyl-trimethoxysilane, butylaminemethyl-triethoxysilane, N-cyclohexyl(aminomethyl) trimethoxy-silane, 2-aminoethylaminomethyl-triethoxysilane, diethylaminomethyl-triethoxysilane, (3-mercaptopropyl)triethoxysilane and (3-mercaptopropyl)trimethoxysilane.

9 . The process as claimed in claim 8 , wherein said coupling agent is selected from the group consisting of (3-mercaptopropyl)trimethoxysilane, (3-aminopropyl)triethoxysilane (APTES), (3-aminopropyl)trimethoxysilane, N-(2-aminoethyl)-3-aminopropyltrimethoxysilane (also known as N-[3-(trimethoxysilyl)propyl]ethylenediamine (EDTMS)), and N-(2-aminoethyl)-3-aminopropyltriethoxysilane.

10 . The process as claimed in claim 2 , wherein said zinc compound is selected from the group consisting of zinc oxide, zinc hydroxide and organic or inorganic zinc salts.

11 . The process as claimed in claim 10 , wherein said organic or inorganic zinc salts are selected from the group consisting of zinc nitrate, zinc sulfate, zinc chloride, zinc bromide and zinc acetate.

12 . A process for the preparation of a vulcanisable elastomeric compound for tyres, where said process comprises at least:
a mixing step (1) of at least one elastomeric polymer and of at least one additive for elastomeric compounds, with the exception of a vulcanising agent, to give a non-vulcanisable elastomeric compound; a mixing step (2) of the non-vulcanisable elastomeric compound and of at least one vulcanising agent, to give a vulcanisable elastomeric compound, and a step of unloading of the vulcanisable elastomeric compound,
wherein the compound of formula (II) as claimed in claim 1 is added in at least one of said mixing steps (1) and (2).

13 . A vulcanisable elastomeric compound obtained as claimed in the process of claim 12 .

14 . A tyre component comprising the vulcanisable compound of claim 13 or the vulcanised compound obtained by vulcanisation thereof.

15 . A tyre for vehicle wheels comprising a component as claimed in claim 14 .

Assignees

• Pirelli

Inventors

• Susanna Antonio
• Donetti Raffaella
• Hanel Thomas
• Scotti Roberto
• Di Credico Barbara
• Mostoni Silvia
• D'Arienzo Massimiliano

Classifications

• B60C1/00 Primary

  Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition · CPC title

• C08K3/36

  Silica · CPC title

• C08L2312/00

  Crosslinking · CPC title

• C08L9/00 Primary

  Compositions of homopolymers or copolymers of conjugated diene hydrocarbons · CPC title

• C01P2002/86

  by NMR- or ESR-data · CPC title