# US 11,299,602 B2 · Silane mixtures and process for preparing same

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- Number: US 11,299,602 B2
- Document ID: US11299602B2
- Status: Granted
- Kind: B2
- Application number: 16/766,462
- Filed: 2018-11-16
- Published: 2020-12-03
- Granted: 2022-04-12
- Earliest claimed: 2017-11-28
- Assignees: Evonik Operations GmbH
- Applicants: Evonik Operations GmbH
- Inventors: Alexander Koepfer; Caren Roeben; Andre Hasse; Frank Forster
- Web page: https://patentgrep.com/patent/US11299602B2

## CPC

- C08K 5/548: containing sulfur {(C08K5/5477 takes precedence)}
- C08L 83/14: in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms (C08L83/10 takes precedence)
- C07F 7/081: {comprising at least one atom selected from the elements N, O, halogen, S, Se or Te}
- C07F 7/1804: {Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896)}
- C08J 3/242: {Applying crosslinking or accelerating agent onto compounding ingredients such as fillers, reinforcements}
- C08K 5/5419: containing at least one Si—C bond
- C08L 7/00: Compositions of natural rubber
- C08L 9/06: Copolymers with styrene
- C08L 21/00: Compositions of unspecified rubbers
- C08K 3/36: Silica
- C08L 2205/025: containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
- C08L 2205/03: containing three or more polymers in a blend
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)

## Abstract

The invention relates to silane mixtures comprising a silane of the formula I (R1)y(R2)3-ySi—R3—(S—R4)n—Sx—R5 (I) and a silane of the formula II (R1)y(R2)3-ySi—R3—S—R4—S—R3—Si(R1)y(R2)3-y (II) where the molar ratio of silane of the formula I to silane of the formula II is 15:85-90:10. The silane mixture according to the invention can be prepared by mixing the silanes of the formula I and silanes of the formula II.

## Claims

### Claim 1

A silane mixture, comprising
a silane of formula (I)
(R1)y(R2)3-ySi—R3—(S—R4)n—Sx—R5 (I); and
a silane of formula (II)
(R1)y(R2)3-ySi—R3—S—R3—Si(R1)y(R2)3-y (II),
wherein
R1 is independently a C1-C10-alkoxy group, phenoxy group, C4-C10-cycloalkoxy group, or alkyl polyether group —O—(R6—O)r—R7 where R6 being a divalent C1-C30 hydrocarbon group, r being an integer in a range of from 1 to 30, and R7 being a monovalent alkyl, alkenyl, aryl, or aralkyl group,
R2 is independently a C6-C20-aryl groups, C1-C10-alkyl groups, C2-C20-alkenyl groups, C7-C20-aralkyl group, or halogen,
R3 is independently a divalent C1-C30 hydrocarbon group,
R4 is independently a divalent C1-C30 hydrocarbon group,
x is an integer in a range of from 1 to 10,
wherein, when x is 1, R5 is a —C(═O)—R8 group with R8 being H, a C1-C20 alkyl group, C6-C20-aryl group, C2-C20-alkenyl group, or a C7-C20-aralkyl group and n is 0, 1, 2, or 3,
wherein, when x is in a range of from 2 to 10, R5 is —(R4—S)n—R3—Si(R1)y(R2)3-y and n is 1, 2 or 3, and
y is independently 1, 2, or 3, or
wherein the silane of the formula (I) is (EtO)3Si—(CH2)3—S—(CH2)6—S2—(CH2)6—S—(CH2)3—Si(OEt)3, (EtO)3Si—(CH2)—S—(CH2)6—S—C(═O)—CH3, (EtO)3Si—(CH2)3—S—(CH2)6—S—C(═O)—C7H15, or (EtO)3Si—(CH2)3—S—(CH2)6—S-—C(═O)—C17H35, and the silane of the formula (II) is (EtO)3Si—(CH2)3—S—(CH2)3—Si(OEt)3,
and
wherein a molar ratio of the silane of the formula (I) to the silane of the formula (II) is in a range of from 20:80 to 90:10.

### Claim 2 (depends on 1)

The mixture of claim 1, wherein n is 1.

### Claim 3 (depends on 2)

The mixture of claim 2, wherein the silane of the formula (I) is
(EtO)3Si—(CH2)3—S—(CH2)6—S2—(CH2)3—Si(OEt)3,
(EtO)3Si—(CH2)3—S—(CH2)6—S—C(═O)—CH3,
(EtO)3Si—(CH2)3—S—(CH2)6—S—C(═O)—C7H15, or
(EtO)3Si—(CH2)3—S—(CH2)6—S—C(═O)—C17H35, and
wherein the silane of the formula (II) is (EtO)3Si—(CH2)3—S—(CH2)3—Si(OEt)3.

### Claim 4 (depends on 1)

The mixture of claim 1, wherein the molar ratio of the silane of the formula (I) to the silane of the formula (II) is in a range of from 35:65 to 90:10.

### Claim 5 (depends on 1)

A process for preparing the silane mixture of claim 1, the process comprising:
mixing the silane of the formula (I)
(R1)y(R2)3-ySi—R3—(S—R4)n—Sx—R5 (I),
and a silane of the formula (II)
(R1)y(R2)3-ySi—R3—S—R3—Si(R1)y(R2)3-y (II),
in a molar ratio in a range of from 15:85 to 90:10.

### Claim 6 (depends on 5)

The process of claim 5, wherein n is 1.

### Claim 7 (depends on 5)

The process of claim 5, wherein the molar ratio of the silane of the formula (I) to the silane of the formula (II) is in a range of from 35:65 to 90:10.

### Claim 8 (depends on 5)

The process of claim 5, wherein the silane of the formula (I) is
(EtO)3Si—(CH2)3—S—(CH2)6—S2—(CH2)3—Si(OEt)3,
(EtO)3Si—(CH2)3—S—(CH2)6—S—C(═O)—CH3,
(EtO)3Si—(CH2)3—S—(CH2)6—S—C(═O)—C7H15, or
(EtO)3Si—(CH2)3—S—(CH2)6—S—C(═O)—C17H35, and
wherein the silane of the formula (II) is (EtO)3Si—(CH2)3—S—(CH2)3—Si(OEt)3.

### Claim 9 (depends on 1)

The mixture of claim 1, wherein R1 in the silane of the formula (I) and (II) is independently a C1-C10-alkoxy group.

### Claim 10 (depends on 1)

The mixture of claim 1, wherein R1 in the silane of the formula (I) and (II) is independently a phenoxy group.

### Claim 11 (depends on 1)

The mixture of claim 1, wherein R1 in the silane of the formula (I) and (II) is independently a C4-C10-cycloalkoxy group.

### Claim 12 (depends on 1)

The mixture of claim 1, wherein R1 in the silane of the formula (I) and (II) is independently an alkyl polyether group —O—(R6—O)r—R7,
wherein R7 is a monovalent alkyl, alkenyl, aryl, or aralkyl group.

### Claim 13 (depends on 1)

The mixture of claim 1, wherein R1 in the silane of the formula (I) and (II) is independently an alkyl polyether group —O—(R6—O)r—R7, and
wherein R7 is a monovalent alkyl.

### Claim 14 (depends on 1)

The mixture of claim 1, wherein the silane of the formula (I) is (EtO)3Si—(CH2)3—S—(CH2)6—S2—(CH2)6—S—(CH2)3—Si(OEt)3.

### Claim 15 (depends on 1)

The mixture of claim 1, wherein the silane of the formula (I) is (EtO)3Si—(CH2)3—S—(CH2)6—S—C(═O)—CH3.

### Claim 16 (depends on 1)

The mixture of claim 1, wherein the silane of the formula (I) is (EtO)3Si—(CH2)3—S—(CH2)6—S—C(═O)—C7H15.

### Claim 17 (depends on 1)

The mixture of claim 1, wherein the silane of the formula (I) is (EtO)3Si—(CH2)3—S—(CH2)6—S—C(═O)—C17H35.

### Claim 18 (depends on 5)

The process of claim 5, wherein the silane of the formula (I) is (EtO)3Si—(CH2)3—S—(CH2)6—S2—(CH2)6—S—(CH2)3—Si(OEt)3.

### Claim 19 (depends on 5)

The process of claim 5, wherein the silane of the formula (I) is (EtO)3Si—(CH2)3—S—(CH2)6—S—C(═O)—CH3.

### Claim 20 (depends on 5)

The process of claim 5, wherein the silane of the formula (I) is (EtO)3Si—(CH2)3—S—(CH2)6—S—C(═O)—C7H15 or (EtO)3Si—(CH2)3—S—(CH2)6—S—C(═O)—C17H35.