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EP-4741404-A1 - FUNCTIONALIZED AMINOSILANE IN THE MANUFACTURE OF POLYMERS

EP4741404A1EP 4741404 A1EP4741404 A1EP 4741404A1EP-4741404-A1

Abstract

The present invention relates to aminosilane compounds useful in the manufacture of polymers that can be used in rubber articles such as tires. The present invention further relates to a process for preparing a polymer in the presence of aminosilane compounds, a polymer obtainable by such process, non-vulcanized and vulcanized polymer compositions comprising the polymer and articles comprising one or more components formed from the vulcanized polymer composition, such as tires or components thereof.

Inventors

  • Boomhoff, Michael
  • THIELE, SVEN
  • KÜHN, Martin
  • Thielemann, Dominique

Assignees

  • Synthos Dwory 7 spolka z ograniczona odpowiedzialnoscia

Dates

Publication Date
20260513
Application Date
20241112

Claims (19)

  1. An aminosilane compound of the following Formula (I): wherein, in Formula (I), m is 1 to 3; n is 0 to 3; o is 1 to 3; A is a C 2 -C 20 hydrocarbon group which optionally comprises at least one heteroatom, selected from S, O and Si; B is a C 2 -C 20 hydrocarbon group which optionally comprises at least one heteroatom, selected from S, O and Si; C independently is Si(R 1 ) x (OR 2 ) y , wherein R 1 and R 2 are each independently a C 1 -C 20 hydrocarbon group, x is 1, 2 or 3, y is 0, 1 or 2 with y = 3-x; when x is 3 then at least one R 1 is a vinyl group; D is a C 1 -C 20 hydrocarbon group; X is D or C; a is 0, 1 or 2; b is 0, 1 or 2; and a + b = 2; and when n is 0 and a is 1 or 2, then A and D may be connected so as to form a cyclic structure.
  2. The compound of claim 1, wherein, in Formula (I), m is 1 to 2; n is 0 to 2; o is 1 to 2; m + n + o = 2, 3 or 4; A and B each independently are a C 2 -C 6 aliphatic hydrocarbon group which optionally comprises at least one heteroatom, selected from S, O and Si; C independently is Si(R 1 ) x (OR 2 ) y , wherein R 1 and R 2 are each independently a C 1 -C 10 aliphatic hydrocarbon group; x is 1, 2 or 3, y is 0, 1 or 2, and y = 3-x; when x is 3 then at least one R 1 is a vinyl group; and D is a C 1 -C 10 hydrocarbon group.
  3. The compound of claim 1 or 2, wherein, in Formula (I), A and B each independently are a C 2 -C 6 aliphatic hydrocarbon group which comprises at least one heteroatom, selected from S and O; C independently is Si(R 1 ) x (OR 2 ) y , wherein R 1 and R 2 are each independently a C 1 -C 10 aliphatic hydrocarbon group; x is 1, and y is 2; D is a C 1 -C 6 hydrocarbon group; a is 0 or 1; b is 1 or 2; and a + b = 2; and when a is 1, then A and D may be connected so as to form a cyclic structure.
  4. The compound of any of claims 1-3, wherein, in Formula (I), A is a C 2 -C 6 hydrocarbon group which comprises one or two heteroatoms, selected from S and O; D is a C 1 -C 6 hydrocarbon group a is 0 or 1; b is 1 or 2; and a + b = 2 n is 0; and when a is 1, then A and D may be connected so as to form a cyclic structure.
  5. The compound of any of claims 1-4, wherein, in Formula (I), m is 1; and/or n is 0; and/or o is 1; and/or A is a C 2 -C 6 hydrocarbon group, preferably a C 2 hydrocarbon group, or is a C 2 -C 6 hydrocarbon group which contains two S or two O atoms; and/or C independently is Si(R 1 ) x (OR 2 ) y , wherein R 1 and R 2 are each independently a C 1 -C 6 hydrocarbon group, preferably a C 1 -C 3 hydrocarbon group, more preferably a C 1 hydrocarbon group, x is land y is 2, preferably 2.
  6. The compound of claim 1, which corresponds to the one of the following structures: or
  7. A process for preparing a polymer, wherein the process comprises the following steps: (a) reacting conjugated diene monomers and optionally one or more aromatic vinyl monomers in the presence of one or more initiator compounds in a polymerization process to form a living polymer chain, (b) reacting the living polymer chain with an aminosilane compound of formula (I) as defined in any of claims 1-6, (c) optionally reacting the remaining living chain ends with a chain end modifier.
  8. The process of claim 7, wherein the polymerization process is an anionic or radical or transition metal-catalyzed polymerization.
  9. A polymer, obtainable by the process of claim 7 or 8.
  10. A polymer which comprises the following structure: wherein A, B, R 1 , R 2 , D, a, b, m, n and o are defined as in any of claims 1-5; X is SiR 1 x (OR 2 ) y P z or a C 1 -C 10 hydrocarbon; P is a conjugated diene polymer optionally comprising vinylaromatic monomers; and x is 0, 1, 2 or 3; y is 0, 1 or 2; z is 1 or 2; and x + y + z = 3 .
  11. A non-vulcanized polymer composition comprising the polymer as defined in claim 9 or 10 and one or more additives.
  12. The polymer composition according to claim 11, wherein the one or more additives are selected from extender oils, stabilizers and further polymers.
  13. The polymer composition according to claim 11 or 12, further comprising one or more fillers.
  14. The polymer composition according to claim 13, wherein the one or more fillers are selected from carbon black, carbon nanotubes, graphite, graphene, silica, carbon-silica dual-phase filler, clays calcium carbonate, magnesium carbonate, lignin, glass particle-based fillers and starch-based fillers, preferably the filler is silica.
  15. The polymer composition according to any one of claims 11 to 14, further comprising one or more vulcanizing agents.
  16. A vulcanized polymer composition obtainable by vulcanizing the polymer composition as defined in claim 15.
  17. A method of making a vulcanized polymer composition, wherein the method comprises the step of vulcanizing the polymer composition as defined in claim 15.
  18. An article comprising at least one component formed from the vulcanized polymer composition as defined in claim 16.
  19. The article according to claim 18, which is a rubber-comprising article, and preferably is a tire, a tire tread, a tire side wall, a tire carcass, a belt, a gasket, a seal, a hose, a vibration damper, a footwear component, a golf ball or a hose, more preferably a summer, winter, all-weather passenger car tire or truck tire.

Description

FIELD OF THE INVENTION The present invention relates to novel aminosilane compounds which can be useful in the manufacture of polymers that can be used in rubber articles such as tires. The present invention further relates to a process for preparing a polymer in the presence of aminosilane compounds, a polymer obtainable by this process, non-vulcanized and vulcanized polymer compositions comprising the polymer and articles comprising one or more components formed from the vulcanized polymer composition. BACKGROUND OF THE INVENTION Articles such as a tire may be formed in the process of vulcanizing a polymer composition that includes a polymer and one or more additives such as for example fillers. Generally, in such compositions, when increasing the polymer functionalization degree by introducing functional groups capable of reacting and/or interacting with the filler, improved dynamic properties in the vulcanized article may be obtained. As a consequence, the rolling resistance and wet grip balance may be improved leading to a lower fuel consumption of the tire and improved tire safety characteristics on a wet road. On the other hand, the viscosity of a non-vulcanized polymer composition increases with increasing functionalization degree due to stronger polymer-filler interactions and more interconnected polymer-filler aggregates. Usually, high viscosities negatively impact the throughput of tire production, rubber sheet quality and rubber formulation extrusion characteristics. Therefore, there is a need for providing polymer compositions with low viscosity of polymers with increased the functionalization degree. The present invention aims at the provision of such polymer composition and provides a hydrolysable aminosilane compound that can be used as a coupling agent when preparing a polymer included in the polymer composition. Standard coupling agents such as tin tetrachloride (SnCl4), tetrachloro silane, etc., may functionalize the polymer chain end and react with components of a composition, for example with a filler or with unsaturated portions of a polymer. Generally, coupling agents may reduce hysteresis loss by reducing the number of free chain ends of the polymer and may reduce the polymer solution viscosity compared with non-coupled, essentially linear, polymer macromolecules of identical molecular weight. By using the coupling agent according to the present invention, the coupled fraction is hydrolyzed during compounding leading to lower molecular weights with functional groups at the chain ends capable of interacting with the filler. As a result, lower viscosities of the corresponding formulations are obtained by maintaining dynamic properties of the cured formulations when compared to polymers coupled with a standard coupling agent and optionally functionalized with similar chain end modifiers. Due to the lower compound viscosities the processing properties are improved although the functionalization degree is increased. SUMMARY OF THE INVENTION The present invention is based on the finding that the above objects can be solved by carrying out the polymerization of conjugated diene monomers in the presence of an aminosilane compound. Thus, in a first aspect, the present invention provides an aminosilane compound of the following Formula (I): wherein, in formula (I), m is 1 to 3; n is 0 to 3; o is 1 to 3; A is a C2-C20 hydrocarbon group which optionally comprises at least one heteroatom, selected from S, O and Si; B is a C2-C20 hydrocarbon group which optionally comprises at least one heteroatom, selected from S, O and Si; C independently is Si(R1)x(OR2)y, wherein R1 and R2 are each independently a C1-C20 hydrocarbon group, x is 1, 2 or 3, y is 0, 1 or 2 with y = 3-x, and when x is 3 then at least one R1 is a vinyl group; D is a C1-C20 hydrocarbon group; X is D or C; a is 0, 1 or 2; b is 0, 1 or 2; and a + b = 2; and when n is 0 and a is 1 or 2, then A and D may be connected so as to form a cyclic structure. In a second aspect, the present invention provides a process for preparing a polymer, wherein the process comprises the following steps: (a) reacting conjugated diene monomers and optionally one or more aromatic vinyl monomers in the presence of one or more initiator compounds in a polymerization process to form a living polymer chain, (b) reacting the living polymer chain with an aminosilane compound of formula (I) as defined in the first aspect of the invention, and (c) optionally reacting the remaining living chain ends with a chain end modifier. In a third aspect, the present invention provides a polymer obtainable by the process as defined in the second aspect of the invention. In a fourth aspect, the present invention provides a non-vulcanized polymer composition comprising the polymer of the third aspect of the present invention and one or more additives. In a fifth aspect, the present invention provides a vulcanized polymer composition which is obtainable by vulcanizing the polymer