Polymer network forming silane compositions

Patent metadata

Field	Value
Publication number	US-11267955-B2
Application number	US-201916674713-A
Country	US
Kind code	B2
Filing date	Nov 5, 2019
Priority date	Nov 5, 2018
Publication date	Mar 8, 2022
Grant date	Mar 8, 2022

Abstract

A silane based additive, rubber formulations including the additive and tires having tread portions made with the additive, together with methods of forming those products, are provided. Uncured rubber formulations in accordance with preferred embodiments of the invention comprise (1) a rubbery primary polymer or polymer blend, such as natural rubber and/or synthetic rubber; (2) reinforcing silica filler; (3) a network forming monomer or polymer, especially a thermosetting network forming moiety, for forming a secondary polymeric network; and (4) a silane containing one or more moieties of the aforementioned network forming polymer. In particular networks which can be generated in-situ are preferred. The cured rubber formulation should comprise the silica, having the secondary polymer network coupled thereto, within the rubber matrix, and not directly to the rubber chains via sulfidic linkages.

First claim

What is claimed is:

1. A hydrolyzable alkoxymethylamino-functional silane, comprising:
at least one hydrolyzable silyl group and at least one alkoxymethylamino-functional group, wherein the alkoxymethylamino-functional group and the hydrolyzable silyl group are each bonded to an sp 2 carbon atom on an organic group to form a N—C covalent bond, and wherein the at least one alkoxymethylamino-functional group has the structure
(R 1 OCH 2 ) 2 N—  (I)

where R 1 is independently hydrogen, an alkyl group having from 1 to 10 carbon atoms, a cycloalkyl group having from 3 to 10 carbon atoms, an alkenyl group having from 2 to 10 carbon atoms, an aryl group having from 6 to 12 carbon atoms or an aralkyl group having from 7 to 12 carbon atoms; and
the at least one hydrolyzable silyl group has the chemical Formula (II):

wherein
each R 2 is independently hydrogen, an alkyl group having from 1 to 10 carbon atoms and optionally at least one oxygen atom, a cycloalkyl group having from 3 to 10 carbon atoms, an alkenyl group having from 2 to 10 carbon atoms, an aryl group having from 6 to 12 carbon atoms or an aralkyl group having from 7 to 12 carbon atoms;
each R 3 is independently an alkyl group having from 1 to 3 carbon atoms or phenyl;
R 4 is an alkylene group having from 1 to 10 carbon atoms and optionally at least one oxygen atom, a cycloalkylene group having from 3 to 10 carbon atoms, an alkenylene group having from 2 to 10 carbon atoms, an arylene group having from 6 to 12 carbon atoms, an aralkylene group having from 7 to 14 carbon atoms;
each X is a

SCH 2 —,

 —NR 1 C(═O)N(R 1 )CH 2 —,

 —NR 1 (C═O)OCH 2 —, —OCH 2 —, —NR 1 CH 2 — or —OCH 2 CH(OH)CH 2 OCH 2 — group, wherein the methylene carbon atom of the group is bonded to the nitrogen atom, or —NH(C═O)—, —OCH 2 CH(OH)CH 2 — or a chemical bond which forms the bond between the R 4 group and the nitrogen atom shown in Formula (II); and
the subscript a is an integer equal to 1, 2 or 3, with the proviso that the nitrogen atom shown in Formula (II) is bonded to a sp 2 -hybridized carbon atom.

2. The hydrolyzable alkoxymethylamino-functional silane of claim 1 , wherein the at least one of the hydrolyzable alkoxymethylamino-functional silanes has the chemical structure of Formulae III or IV or stereoisomers thereof:

wherein
each R 1 is independently hydrogen, an alkyl group having from 1 to 10 carbon atoms, a cycloalkyl group having from 3 to 10 carbon atoms, an alkenyl group having from 2 to 10 carbon atoms, an aryl group having from 6 to 12 carbon atoms or an aralkyl group having from 7 to 12 carbon atoms;
each R 2 is independently hydrogen, an alkyl group having from 1 to 10 carbon atoms and optionally at least one oxygen atom, a cycloalkyl group having from 3 to 10 carbon atoms, alkenyl group having from 2 to 10 carbon atoms, an aryl group having from 6 to 12 carbon atoms or an aralkyl group having from 7 to 12 carbon atoms;
each R 3 is independently an alkyl group having from 1 to 3 carbon atoms or phenyl;
each R 4 is independently an alkylene group having from 1 to 10 carbon atoms and optionally at least one oxygen atom, a cycloalkylene group having from 3 to 10 carbon atoms, an alkenylene group having from 2 to 10 carbon atoms, an arylene group having from 6 to 12 carbon atoms, an aralkylene group having from 7 to 14 carbon atoms;
each R 5 and R 7 is independently phenyl, —N(CH 2 OR 1 ) 2 , —N(CH 2 OR 1 )(XR 4 Si(R 3 ) 3-a (OR 2 ) a ), —N(XR 4 Si(R 3 ) 3-a (OR 2 ) a ) 2 ,

each R 6 , R 8 and R 9 is independently hydrogen, —CH 2 OR 1 or —XR 4 Si(R 3 ) 3-a (OR 2 ) a ;
each X is independently —SCH 2 —, R 1 OC(═O)NCH 2 —, —NR 1 C(═O)N(R 1 )CH 2 —, R 1 2 N(C═O)NCH 2 —, —NR 1 (C═O)OCH 2 —, —OCH 2 —,

or —OCH 2 CH(OH)CH 2 OCH 2 — group, where the methylene carbon atom of the group is bonded to the nitrogen atom, or —NH(C═O)—, —OCH 2 CH(OH)CH 2 — or a chemical bond which forms the bond between the R 4 group and the nitrogen atom, with the proviso that the nitrogen atom is bonded to a sp 2 -hybridized carbon atom; the subscripts a, b, c, d, x and y are independently integers where a is 1, 2 or 3; b is 0 or 1; c is 0 or 1; x is from 1 to 20; and y is from 0 to 20.

3. The hydrolyzable alkoxymethylamino-functional silane of claim 2 , wherein
each R 1 is independently an alkyl group having from 1 to 3 carbon atoms;
each R 2 is independently an alkyl group having from 1 to 3 carbon atoms;
each R 3 is independently an alkyl group having from 1 to 3 carbon atoms; each R 4 is independently an alkylene group having from 1 to 6 carbon atoms;
each R 5 and R 7 is independently —N(CH 2 OR 1 ) 2 or —N(CH 2 OR 1 )(CH 2 XR 4 Si(R 3 ) 3-a (OR 2 ) a );
each R 6 , R 8 and R 9 is —CH 2 OR 1 ;
each X is independently —SCH 2 — or —NR 1 CH 2 — group; the subscripts a, b, c, d, x and y are independently integers where a is 3; b is 1; c is 1; x is 1, 2 or 3; and y is 0.

4. The hydrolyzable alkoxymethylamino-functional silane of claim 1 , wherein said silane is selected from the group consisting of 1-(5-trimethoxysilyl-2-thiapentyl)-1,3,3-tris-methoxymethylurea, 1,3-bis-(1-(5-trimethoxysilyl-2-thiapentyl)-1,3-bis-methoxymethylurea, 3,3-bis-(3-dimethoxysilyl-2-thiapropyl)-1,1-bis-methoxymethylurea, 1-(5-triethoxysilyl-2-thiapentyl)-1,3,3-tetra-ethoxymethylurea, 1-(5-triethoxysilyl-2-aza-2-methyl-pentyl)-1,3,3-tris-ethoxymethylurea, 1,3-bis-(7-triethoxysilyl-2,4-diaza-3-oxo-heptyl)-1,3-bis-ethoxymethylurea, 3,3-bis-(1-(5-triethoxysilyl-2-thiapentyl)-1,1-bis-ethoxymethylurea, 1-(5-triethoxysilyl-2-thiapentyl)-1,3,3-tris-propoxymethylurea, 1-(5-triethoxysilyl-2-thiapentyl)-1,3,3-tris-propoxymethylurea, 1,3-bis-(5-tripropoxysilyl-2-thiapentyl)-1,3-bis-propoxymethylurea, 3,3-bis-(5-tripropoxysilyl-2-thiapentyl)-1,1-bis-propoxymethylurea, 1,3-bis-(5-tripropoxysilyl-2-thiapentyl)-1,3,3-tetra-butoxymethylurea, 1-(5-triphenoxysilyl-2-thiapentyl)-1,3,3-tetra-phenoxymethylurea, N-[1-(5-triethoxysilyl-2-thiapentyl)-1,3-tris-ethoxymethylureidomethyl]-1,3,3-tetra-ethoxymethylurea, N, N′-bis-[(1-(5-triethoxysilyl-2-thiapentyl)-1,3-bis-ethoxymethylureidomethyl]-1,3-bis-ethoxymethylurea, N, N′-bis-[1-(5-triethoxysilyl-2-thiapentyl)-1,3-bis-ethoxymethylureido-methoxymethyl]-1,3-bis-ethoxymethylurea, N-(5-triethoxysilyl-2-thiapentyl)-N,N′,N′,N″,N″-pentakis-methoxymethyl-[1,3,5]triazine-2,4,6-triamine, N, N″-bis-(5-triethoxysilyl-2-thiapentyl)-N,N′,N′,N″-tetrakis-methoxymethyl-[1,3,5]triazine-2,4,6-triamine, N′,N″-(5-triethoxysilyl-2-thiapentyl)-N,N,N′,N″-tetrakis-methoxymethyl-[1,3,5]triazine-2,4,6-triamine, N-(5-triethoxysilyl-2-aza-2-methyl-pentyl)-N,N′,N′,N″,N″-pentakis-ethoxymethyl-[1,3,5]triazine-2,4,6-triamine, N″-(7-triethoxysilyl-2,4-diaza-3-oxo-heptyl)-N,N,N′,N′,N″-pentakis-ethoxymethyl-[1,3,5]triazine-2,4,6-triamine, N′,N″-(7-triethoxysilyl-2,4-diaza-3-oxo-heptyl)-N,N,N′,N″-tetrakis-ethoxymethyl-[1,3,5]triazine-2,4,6-triamine, N-(5-triethoxysilyl-2-aza-2-methyl-pentyl)-N,N′,N′,N″,N″-pentakis-propoxymethyl-[1,3,5]triazine-2,4,6-triamine and N-(5-triethoxysilyl-2-aza-2-methyl-pentyl)-N,N′,N′,N″,N″-pentakis-phenoxymethyl-[1,3,5]triazine-2,4,6-triamine.

5. A process for prepa

Assignees

• Momentive Performance Mat Inc

Inventors

• York William Michael
• Adepetun Adeyemi Adedayo
• Hwang Lesley
• Pohl Eric

Classifications

• C08K5/3492

  Triazines · CPC title

• C08K5/5477

  containing nitrogen in a heterocyclic ring · CPC title

• C09C1/3081

  Treatment with organo-silicon compounds · CPC title

• C08K9/02

  Ingredients treated with inorganic substances · CPC title

• C08K5/13

  Phenols; Phenolates · CPC title