IP Library Granted Patent US 9,528,036
Granted Patent B2
US 9,528,036 · App. 14/629,177 · Granted Dec 27, 2016

Low-voc dialkyl-functional alkoxysiloxanes, processes and use thereof as hydrophobizing impregnating agents for mineral building materials

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Quick Facts
Patent No.
US 9,528,036
App. No.
14/629,177
Granted
Dec 27, 2016
Kind
B2
Abstract

Low-VOC compositions of dialkyl-functional siloxane oligomers, especially of methylalkylalkoxysiloxanes, and processes for producing them are provided. Additionally methods for hydrophobizing porous mineral substrates employing the low-VOC compositions, in the course of which few or no volatile organic compounds are released, are provided.

Claims (51)

1. A composition comprising:

a dialkyl-functional siloxane oligomer of formula (I):

and, optionally,

a dialkyl-functional cyclic siloxane oligomer of formula (II):

wherein

each R′ is independently a linear or branched octyl group,

each R″ is a methyl group,

each R is independently hydrogen or an alkyl group having 1 to 2 C atoms,

n is an integer from 0 to 10 and

m is an integer from 2 to 10.

2. The composition according to claim 1 , wherein

R′ is an alkyl group selected from the group consisting of n-octyl, 2-methylheptyl, 3-methylheptyl, 4-methylheptyl, 2,2-dimethylhexyl, 2,3-dimethylhexyl, 2,4-dimethylhexyl, 2,5-dimethylhexyl, 3,3-dimethylhexyl, 3,4-dimethylhexyl, 3-ethylhexyl, 2,2,3-trimethylpentyl, 2,2,4-trimethylpentyl (isooctyl), 2,3,3-trimethylpentyl, 2,3,4-trimethylpentyl, 3-ethyl-2-methylpentyl, 3-ethyl-3-methylpentyl, and 2,2,3,3-tetramethylbutyl.

3. The composition according to claim 2 , wherein R′ is n-octyl, or 2,2,4-trimethylpentyl(isooctyl).

4. The composition according to claim 1 , wherein

n is an integer from 1 to 5.

5. The composition according to claim 1 , further comprising one or more different

dialkyl-functional linear siloxane oligomers of formula I.

6. The composition according to claim 1 , comprising the dialkyl-functional cyclic siloxane oligomer of formula (II).

7. The composition according to claim 6 , wherein a molar ratio of the dialkyl-siloxane oligomer of formula I to the dialkyl-functional cyclic siloxane oligomer of formula (II) is from 100:1 to 1:100.

8. The composition according to claim 1 , wherein a total wt % of the the dialkyl-siloxane oligomers of the formula I and of the formula II is from 0.01 to 99.9 wt % of the composition.

9. The composition according to claim 1 , further comprising an organosilane or organosiloxane of formula (IV):

R 1 —Si(O) y R 2 z   (IV),

wherein

R 1 is a linear or branched alkyl group having 3 to 20 C atoms,

each R 2 is independently a linear or branched alkoxy group having 1 to 4 C atoms or is a hydroxyl group, and

y is from 0 to 1.5, z is 0, 1, 2or 3,

with the proviso that when y is 1.5, z is 0, when y is 1, z is 1, when y is 0.5, z is 2 and when y is 0, z is 3.

10. A process for producing the composition according to claim 1 , comprising:

subjecting at least one silane of formula (III) to hydrolysis and condensation in the presence of a diluent or reaction medium and a molar amount of water based on moles of silicon atoms in the silanes of the formula III, and optionally

removing the diluent or the reaction medium:

R′—SiR″(X) 2   (III),

wherein

R′ is a linear or branched alkyl group having 3 to 8 C atoms,

R″ is an alkyl group having 1 to 3 C atoms,

each X is independently halogen, —OR or —OH, and

R is independently an alkyl group having 1 to 2 C atoms.

11. The process according to claim 10 , wherein

a molar ratio of water to silicon atoms (mol H 2 O/mol Si) is from 0.3 to 1.0 mol of water per mole of silicon atoms.

12. The process according to claim 10 , wherein the diluent or reaction medium comprises an alcohol.

13. The process according to claim 10 wherein X is chlorine.

14. The process according to claim 10 , wherein X is —OR and/or —OH and each R is independently an alkyl group having 1 to 2 C atoms.

15. The process according to claim 10 wherein the hydrolysis and/or condensation takes place in the presence of a catalyst.

16. The process according to claim 10 , wherein the hydrolysis and/or condensation takes place in a temperature range from 25 to 80° C. and the diluent and/or water is removed from the composition under reduced pressure at a composition temperature of less than or equal to 70° C.

17. The process according to claim 10 , further comprising:

adding the diluent or reaction medium and the water in the form of an alcohol/water mixture to the silane of formula (III); or

separately adding the diluent or reaction medium alcohol and water;

carrying out hydrolysis and/or condensation in the temperature range from 25 to 80° C., for 20 minutes to 2 hours; and

removing the diluent or reaction medium alcohol and water under reduced pressure at a liquid-phase temperature below 65° C. to obtain the composition.

18. A method for hydrophobizing a surface of a substrate or for hydrophobizing materials in mass, comprising applying the composition according to claim 1 to the substrate surface or to the material mass.

19. The method according to claim 18 , wherein the substrate or material is a mineral building material, a porous mineral substrate, or a silicatic material selected from the group consisting of concrete, fibre cement, clay, brick, marble, granite, sandstone, lime sandstone, bricks, screed, render, plaster, a silicatic composite, ceramics, wood, wood composites and wood polymers.

20. A polymeric composition comprising the composition according to claim 1 , wherein the polymeric composition is selected from the group of formulations consisting of a coating material, a composite material, a formulation for forming a water barrier or a water-vapour barrier, an adhesive for forming water and vapour barriers, a drying agent, an anti-foam agent, a care composition adjuvant, a cosmetic formulation, a textile formulation, a formulation for natural or synthetic leather, and a textile or fibre composition adjuvant.

Assignments (3)
CHANGE OF NAME Recorded Jan 31, 2020
From: EVONIK DEGUSSA GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 051765/0166 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 1, 2015
From: EVONIK INDUSTRIES AG
To: EVONIK DEGUSSA GMBH
Reel/Frame 037174/0982 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 20, 2015
From: STUDTE, CHRISTOPHER; LJESIC, SPOMENKO
To: EVONIK INDUSTRIES AG
Reel/Frame 036137/0057 →