IP Library Granted Patent US 10,266,655
Granted Patent B2
US 10,266,655 · App. 15/530,148 · Granted Apr 23, 2019

Aqueous composition comprising [3-(2,3-dihydroxyprop-1-oxy)propyl] silanol oligomers, process for preparation thereof and use thereof

Inventors: Philipp Albert (Rheinfelden, DE); Julia Kirberg (Rheinfelden, DE); Jennifer Schrantz (Rheinfelden, DE); Eckhard Just (Rheinfelden, DE)
Assignee: Evonik Degussa GmbH
C08G77/18C08L83/04C08L83/06C09D7/65C09D163/00C08G77/045C08G77/14C08G77/16
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Quick Facts
Patent No.
US 10,266,655
App. No.
15/530,148
Granted
Apr 23, 2019
Kind
B2
Abstract

The present invention relates to a composition comprising water and a mixture of [3-(2,3-dihydroxyprop-1-oxy)propyl]silanol oligomers and ethers thereof, wherein the proportion of epoxy groups bound within Si compounds which may be present in the composition is not more than 0.05 mol of epoxy groups per mole of Si in the composition. The invention further relates to a particular process for preparing a composition according to the invention and to the use thereof.

Claims (39)

1. A composition, comprising:

water; and

a mixture of [3-(2,3-dihydroxyprop-1-oxy)propyl]silanol oligomers and ethers thereof;

wherein the proportion of epoxy groups bound within Si compounds which may be present in the composition is not more than 0.05 mol of epoxy groups per mole of Si in the composition; and

wherein the composition comprises [3-(2,3-dihydroxyprop-1-oxy)propyl]silanol oligomers or ethers thereof of the general formula I

Y—Si(OH) 2 O 1/2 [Y—Si(OH)O 2/2 ] n [Y—SiO 3/2 ] m (Y—)Si(OH) 2 O 1/2   (I)

wherein n>0 and m>0, Y groups are R″O—CH 2 —CH(OR′)—CH 2 —O—C 3 H 6 — and the R′ and R″ groups are the same or different and may be H, methyl and ethyl and

optionally comprises silanols of the general formula II

Y—Si(OH)(OR) 2   (II)

wherein Y group is R″O—CH 2 —CH(OR′)—CH 2 —O—C 3 H 6 — and the R, R′ and R″ groups are the same or different and may be H, methyl and ethyl.

2. The composition according to claim 1 ,

wherein the proportion of epoxy groups bound within Si compounds which may be present in the composition is 0 to 0.04 mol of epoxy groups per mole of Si in the composition.

3. The composition according to claim 1 ,

wherein the composition has an active ingredient content of compounds of the formula I including compounds of the formula II of up to 80% by weight, based on the overall composition.

4. The composition according to claim 1 ,

wherein the composition has been acidified and contains formic acid or acetic acid.

5. The composition according to claim 1 ,

wherein the composition contains not more than 1% by weight of free alcohol, wherein the % by weight figure is based on the composition and the alcohol is selected from the group of methanol and ethanol.

6. The composition according to claim 1 ,

wherein the composition is water-dilutable.

7. A component in an epoxy resin formulation, a coupling reagent in a primer solution, a sealant on an inorganic substrate, a reactive binder or a co-binder, comprising:

the composition according to claim 1 .

8. A process for producing a composition comprising:

water; and

a mixture of [3-(2,3-dihydroxyprop-1-oxy)propyl]silanol oligomers and ethers thereof;

wherein the proportion of epoxy groups bound within Si compounds which may be present in the composition is not more than 0.05 mol of epoxy groups per mole of Si in the composition,

said process comprising:

1) combining 3-glycidyloxypropyltrimethoxysilane or 3-glycidyloxypropyltriethoxysilane or a mixture of 3-glycidyloxypropyltrimethoxysilane and 3-glycidyloxypropyltriethoxysilane as 3-glycidyloxypropyltrialkoxysilane and mixing it in the presence of an acid with a defined amount of distilled, demineralized or deionized water within 10 to 30 minutes,

2) heating the reaction mixture and stirring it at 55 to 70° C. for 1.5 to 5 hours,

3) then, under reduced pressure at a temperature in the range from 40 to 55° C. over at least 10 hours, distilling an alcohol/water mixture and at the same time replacing it, based on weight, with distilled, demineralized or deionized water and conducting the distillation over at least 10 hours until the top product of the distillation column ultimately contains only water.

9. The process according to claim 8 ,

wherein, in 1, the 3-glycidyloxypropyltrialkoxysilane and water are used in a molar ratio of 1:3 to 60.

10. The process according to claim 8 ,

wherein, in 1, the acid used is formic acid or acetic acid in a molar ratio to 3-glycidyloxypropyltrialkoxysilane of 0.03 to 0.06:1.

11. An aqueous composition obtainable according to the process of claim 8 .

12. An aqueous composition obtained by a process comprising:

1) combining 3-glycidyloxypropyltrimethoxysilane or 3-glycidyloxypropyltriethoxysilane or a mixture of 3-glycidyloxypropyltrimethoxysilane and 3-glycidyloxypropyltriethoxysilane as 3-glycidyloxypropyltrialkoxysilane and mixing it in the presence of an acid with a defined amount of distilled, demineralized or deionized water within 10 to 30 minutes,

2) heating the reaction mixture and stirring it at 55 to 70° C. for 1.5 to 5 hours,

3) then, under reduced pressure at a temperature in the range from 40 to 55° C. over at least 10 hours, distilling an alcohol/water mixture and at the same time replacing it, based on weight, with distilled, demineralized or deionized water and conducting the distillation over at least 10 hours until the top product of the distillation column ultimately contains only water.

Assignments (2)
CHANGE OF NAME Recorded Nov 18, 2019
From: EVONIK DEGUSSA GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 051045/0872 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 10, 2017
From: ALBERT, PHILIPP; KIRBERG, JULIA; SCHRANTZ, JENNIFER; JUST, ECKHARD
To: EVONIK DEGUSSA GMBH
Reel/Frame 042314/0129 →
Priority Claims (1)
EP 15198353 · Dec 8, 2015 · regional
Continuity (1)
Related Publication 20170166702A1 · Jun 15, 2017