Silane mixtures and process for preparing same

Patent metadata

Field	Value
Publication number	US-11299602-B2
Application number	US-201816766462-A
Country	US
Kind code	B2
Filing date	Nov 16, 2018
Priority date	Nov 28, 2017
Publication date	Apr 12, 2022
Grant date	Apr 12, 2022

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.

First claim

The invention claimed is:

1. A silane mixture, comprising
a silane of formula (I)
(R 1 ) y (R 2 ) 3-y Si—R 3 —(S—R 4 ) n —S x —R 5   (I); and

a silane of formula (II)
(R 1 ) y (R 2 ) 3-y Si—R 3 —S—R 3 —Si(R 1 ) y (R 2 ) 3-y   (II),

wherein
R 1 is independently a C1-C10-alkoxy group, phenoxy group, C4-C10-cycloalkoxy group, or alkyl polyether group —O—(R 6 —O) r —R 7 where R 6 being a divalent C1-C30 hydrocarbon group, r being an integer in a range of from 1 to 30, and R 7 being a monovalent alkyl, alkenyl, aryl, or aralkyl group,
R 2 is independently a C6-C20-aryl groups, C1-C10-alkyl groups, C2-C20-alkenyl groups, C7-C20-aralkyl group, or halogen,
R 3 is independently a divalent C1-C30 hydrocarbon group,
R 4 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, R 5 is a —C(═O)—R 8 group with R 8 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, R 5 is —(R 4 —S) n —R 3 —Si(R 1 ) y (R 2 ) 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) 3 Si—(CH 2 ) 3 —S—(CH 2 ) 6 —S 2 —(CH 2 ) 6 —S—(CH 2 ) 3 —Si(OEt) 3 , (EtO) 3 Si—(CH 2 )—S—(CH 2 ) 6 —S—C(═O)—CH 3 , (EtO) 3 Si—(CH 2 ) 3 —S—(CH 2 ) 6 —S—C(═O)—C 7 H 15 , or (EtO) 3 Si—(CH 2 ) 3 —S—(CH 2 ) 6 —S-—C(═O)—C 17 H 35 , and the silane of the formula (II) is (EtO) 3 Si—(CH 2 ) 3 —S—(CH 2 ) 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.

2. The mixture of claim 1 , wherein n is 1.

3. The mixture of claim 2 , wherein the silane of the formula (I) is
(EtO) 3 Si—(CH 2 ) 3 —S—(CH 2 ) 6 —S 2 —(CH 2 ) 3 —Si(OEt) 3 ,

(EtO) 3 Si—(CH 2 ) 3 —S—(CH 2 ) 6 —S—C(═O)—CH 3 ,

(EtO) 3 Si—(CH 2 ) 3 —S—(CH 2 ) 6 —S—C(═O)—C 7 H 15 , or

(EtO) 3 Si—(CH 2 ) 3 —S—(CH 2 ) 6 —S—C(═O)—C 17 H 35 , and

wherein the silane of the formula (II) is (EtO) 3 Si—(CH 2 ) 3 —S—(CH 2 ) 3 —Si(OEt) 3 .

4. 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.

5. A process for preparing the silane mixture of claim 1 , the process comprising:
mixing the silane of the formula (I)
(R 1 ) y (R 2 ) 3-y Si—R 3 —(S—R 4 ) n —S x —R 5   (I),

and a silane of the formula (II)
(R 1 ) y (R 2 ) 3-y Si—R 3 —S—R 3 —Si(R 1 ) y (R 2 ) 3-y   (II),

in a molar ratio in a range of from 15:85 to 90:10.

6. The process of claim 5 , wherein n is 1.

7. 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.

8. The process of claim 5 , wherein the silane of the formula (I) is
(EtO) 3 Si—(CH 2 ) 3 —S—(CH 2 ) 6 —S 2 —(CH 2 ) 3 —Si(OEt) 3 ,

(EtO) 3 Si—(CH 2 ) 3 —S—(CH 2 ) 6 —S—C(═O)—CH 3 ,

(EtO) 3 Si—(CH 2 ) 3 —S—(CH 2 ) 6 —S—C(═O)—C 7 H 15 , or

(EtO) 3 Si—(CH 2 ) 3 —S—(CH 2 ) 6 —S—C(═O)—C 17 H 35 , and

wherein the silane of the formula (II) is (EtO) 3 Si—(CH 2 ) 3 —S—(CH 2 ) 3 —Si(OEt) 3 .

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

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

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

12. The mixture of claim 1 , wherein R 1 in the silane of the formula (I) and (II) is independently an alkyl polyether group —O—(R 6 —O) r —R 7 ,
wherein R 7 is a monovalent alkyl, alkenyl, aryl, or aralkyl group.

13. The mixture of claim 1 , wherein R 1 in the silane of the formula (I) and (II) is independently an alkyl polyether group —O—(R 6 —O) r —R 7 , and
wherein R 7 is a monovalent alkyl.

14. The mixture of claim 1 , wherein the silane of the formula (I) is (EtO) 3 Si—(CH 2 ) 3 —S—(CH 2 ) 6 —S 2 —(CH 2 ) 6 —S—(CH 2 ) 3 —Si(OEt) 3 .

15. The mixture of claim 1 , wherein the silane of the formula (I) is (EtO) 3 Si—(CH 2 ) 3 —S—(CH 2 ) 6 —S—C(═O)—CH 3 .

16. The mixture of claim 1 , wherein the silane of the formula (I) is (EtO) 3 Si—(CH 2 ) 3 —S—(CH 2 ) 6 —S—C(═O)—C 7 H 15 .

17. The mixture of claim 1 , wherein the silane of the formula (I) is (EtO) 3 Si—(CH 2 ) 3 —S—(CH 2 ) 6 —S—C(═O)—C 17 H 35 .

18. The process of claim 5 , wherein the silane of the formula (I) is (EtO) 3 Si—(CH 2 ) 3 —S—(CH 2 ) 6 —S 2 —(CH 2 ) 6 —S—(CH 2 ) 3 —Si(OEt) 3 .

19. The process of claim 5 , wherein the silane of the formula (I) is (EtO) 3 Si—(CH 2 ) 3 —S—(CH 2 ) 6 —S—C(═O)—CH 3 .

20. The process of claim 5 , wherein the silane of the formula (I) is (EtO) 3 Si—(CH 2 ) 3 —S—(CH 2 ) 6 —S—C(═O)—C 7 H 15 or (EtO) 3 Si—(CH 2 ) 3 —S—(CH 2 ) 6 —S—C(═O)—C 17 H 35 .

Assignees

• Evonik Operations Gmbh

Inventors

• Koepfer Alexander
• Roeben Caren
• Hasse Andre
• Forster Frank

Classifications

• C08K5/5419

  containing at least one Si—C bond · CPC title

• C07F7/188

  by reactions involving the formation of Si-O linkages · CPC title

• C08J3/242

  Applying crosslinking or accelerating agent onto compounding ingredients such as fillers, reinforcements · CPC title

• C08K5/54 Primary

  Silicon-containing compounds {(C08K5/0091 takes precedence)} · CPC title

• C07F7/1804

  Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896) · CPC title