Organoalkoxysilanes

• US 20090075096A1
• Filed: 05/05/2008
• Published: 03/19/2009
• Est. Priority Date: 04/29/2005
• Status: Abandoned Application

• Current Assignee: Sika Technology Ag (Compagnie de Saint-Gobain SA)
• Original Assignee: Sika Technology Ag (Compagnie de Saint-Gobain SA)
• Inventors: Jucker, Barbara, Burckhardt, Urs, Pfenninger, Ueli, Butikofer, Pierre-Andre
• Application Number:
  US12/149,561
• Publication Number:
  US 20090075096A1
• Time in Patent Office: Days
• US Class Current: 428/447
• CPC Class Codes: C07F 7/1804 Compounds having Si-O-C linkages Si-O-acyl linkages C07F7/1896
• CPC Class Codes: C08K 5/544 containing nitrogen
• CPC Class Codes: C08K 5/5455 containing at least one group
• CPC Class Codes: C08K 5/548 containing sulfur C08K5/5477 takes precedence
• CPC Class Codes: C08L 75/04 Polyurethanes
• CPC Class Codes: C08L 83/00 Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 83/08 containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
• CPC Class Codes: Y10T 428/31663 As siloxane, silicone or silane

Abstract

The present invention relates to organoalkoxysilanes containing a urea or thiourea or carbamate or thiocarbamate group of formula (I), as well as preparation and use thereof. It further relates to a composition containing the organoalkoxysilane of formula (I). Such compositions are especially suitable as adhesives and sealants, and have high stretchability and high strength.

Claims

1. An organoalkylsilane of formula (I)

wherein:

R¹ is chosen from substituted and unsubstituted members of the group consisting of alkyl, cycloalkyl, aryl, and arylalkyl groups, which members optionally include one or more heteroatoms, and which members do not include any groups that react with water, silane, amino groups or polymerizable double bonds;

R² is chosen from linear, branched and cyclic alkylene groups with 1 to 20 C atoms, which alkylene groups optionally include one or more aromatic moieties and optionally include one or more heteroatoms;

R³ is chosen from alkyl groups with 1 to 8 C atoms;

R⁴ is chosen from alkyl groups with 1 to 5 C atoms;

a represents 0 or 1 or 2;

X represents O or S;

Y represents O, S or N—

R⁵;

wherein;

R⁵ is chosen from linear and branched hydrocarbon residues having 1 to 20 C atoms, which optionally include cyclic moieties, and which optionally include at least one functional group chosen from the group consisting of alkoxysilyl, ether, sulfone, nitrile, nitro, carboxylic acid ester, sulfonic acid ester, and phosphonic acid ester groups.

2. The organoalkoxysilane according to claim 1, wherein a represents 0 or 1.

3. The organoalkoxysilane according to claim 1, wherein R³ is chosen from methyl and ethyl groups.

4. The organoalkoxysilane according to claim 3, wherein R³ is a methyl group.

5. The organoalkoxysilane according to claim 1, wherein R⁴ is chosen from methyl, ethyl and isopropyl groups.

6. The organoalkoxysilane according to claim 5, wherein R⁴ is chosen from methyl and ethyl groups.

7. The organoalkoxysilane according to claim 1, wherein Y represents N—

R⁵.

8. The organoalkoxysilane according to claim 7, wherein R⁵ is chosen from methyl groups, ethyl groups, butyl groups, cyclohexyl groups, phenyl groups and residues of formula (III):

wherein;

R⁶ and R⁷ each independently are chosen from the group consisting of hydrogen atoms and residues of members of the group consisting of R⁹, —

COOR⁹, and —

CN; and

R⁸ is chosen from the group consisting of hydrogen atoms and residues of members of the group consisting of —

CH₂—

COOR⁹, —

COOR⁹, —

CN, —

NO₂, —

PO(OR⁹)₂, —

SO₂R⁹, and —

SO₂OR⁹;

wherein;

R⁹ is chosen from the group consisting of hydrocarbon residues with 1 to 20 C atoms, which optionally contain at least one heteroatom.

9. The organoalkoxysilane according to claim 7, wherein in formula (III), R⁶ is —

COOR⁹, R⁷ is H, R⁸ is —

COOR⁹, and R⁹ is chosen from optionally branched alkyl groups with 1 to 8 C atoms.

10. The organoalkoxysilane according to claim 9, wherein the organoalkoxysilane has formula (IV),

wherein:

R¹ is chosen from the group consisting of ethyl, butyl, cyclohexyl, and phenyl groups;

R² is chosen from the group consisting of methylene, propylene, butylene, methylpropylene, and dimethylbutylene groups; and

R⁹ is chosen from the group consisting of methyl, ethyl, and butyl groups.

11. A method for preparing the organoalkoxysilane according to claim 1, wherein a silane of formula (V) is reacted with a monoisocyanate or a monoisothiocyanate of formula (V),

R¹—

N═

C═

X 

 

(VI).

12. An adhesion promoter comprising the organoalkoxysilane according to claim 1.

13. A drying agent comprising the organoalkoxysilane according to claim 1.

14. A crosslinker comprising the organoalkoxysilane according to claim 1.

15. A reactive diluent comprising the organoalkoxysilane according to claim 1.

16. A composition comprising at least one organoalkoxysilane according to claim 1.

17. A moisture-curing composition comprising at least one organoalkoxysilane according to claim 1 and at least one polymer chosen from silane-functional polymers and isocyanate-functional polymers.

18. The moisture-curing composition according to claim 17, wherein the polymer is a silane-functional polymer.

19. The moisture-curing composition according to claim 17, wherein the polymer is an isocyanate-functional polyurethane polymer that is obtained by reaction of a polyol with a polyisocyanate.

20. The moisture-curing composition according to claim 17, wherein the polymer is a polyurethane polymer containing both silane and isocyanate groups, which is obtained by reaction of an isocyanate-functional polyurethane polymer with an organoalkoxysilane having an NCO-reactive group, wherein the organoalkoxysilane is used in a substoichiometric amount relative to the isocyanate groups of the polyurethane polymer.

21. The moisture-curing composition according to claim 18, wherein the polymer is a silane-functional polymer, which is obtained by reaction of an isocyanate-functional polyurethane polymer with an organoalkoxysilane having an NCO-reactive group.

22. The moisture-curing composition according to claim 18, wherein the polymer is a silane-functional polymer, which is obtained by reaction of a hydroxyl group-containing polymer with an isocyanate-functional organoalkoxysilane.

23. The moisture-curing composition according to claim 18, wherein the polymer is a silane-functional polymer, which is obtained by a hydrolysis reaction of a polymer with terminal double bonds.

24. The moisture-curing composition according to claim 20, wherein the organoalkoxysilane having an NCO-reactive group is an aminosilane.

25. The moisture-curing composition according to claim 24, wherein the aminosilane has formula (VII),

wherein:

R² is chosen from linear, branched and cyclic alkylene groups with 1 to 20 C atoms, which alkylene groups optionally include one or more aromatic moieties and optionally include one or more heteroatoms;

R³ is chosen from alkyl groups with 1 to 8 C atoms;

R⁴ is chosen from alkyl groups with 1 to 5 C atoms;

R⁵ is chosen from linear and branched hydrocarbon residues having 1 to 20 C atoms, which optionally include cyclic moieties, and which optionally include at least one functional group chosen from the group consisting of alkoxysilyl, ether, sulfone, nitrile, nitro, carboxylic acid ester, sulfonic acid ester, and phosphonic acid ester groups; and

a represents 0, 1 or 2.

26. The moisture-curing composition according to claim 25, wherein a represents 0 or 1.

27. The moisture-curing composition according to claim 25, wherein in the aminosilane of formula (VII), R³ is chosen from methyl and ethyl groups, and R⁴ is chosen from methyl, ethyl and isopropyl groups.

28. The moisture-curing composition according to claim 27, wherein in the aminosilane of formula (VII), R³ is a methyl group.

29. The moisture-curing composition according to claim 27, wherein in the aminosilane of formula (VII), R⁴ is chosen from methyl and ethyl groups.

30. The moisture-curing composition according to claim 25, wherein in the aminosilane of formula (VII), R⁵ is chosen from methyl groups, ethyl groups, butyl groups, cyclohexyl groups, phenyl groups and residues of formula (III),

wherein:

R⁶ and R⁷ each independently are chosen from the group consisting of hydrogen atoms and residues of members of the group consisting of R⁹, —

COOR⁹, and —

CN; and

R⁸ is chosen from the group consisting of hydrogen atoms and residues of members of the group consisting of —

CH₂—

COOR⁹, —

COOR⁹, —

CN, —

NO₂, —

PO(OR⁹)₂, —

SO₂R⁹, and —

SO₂OR⁹;

wherein;

R⁹ is chosen from the group consisting of hydrocarbon residues with 1 to 20 C atoms, which optionally contain at least one heteroatom.

31. The moisture-curing composition according to claim 30, wherein in formula (III), R⁶ is —

COOR⁹, R⁷ is H, R⁸ is —

COOR⁹, and R⁹ is chosen from optionally branched alkyl groups with 1 to 8 C atoms.

32. The moisture-curing composition according to claim 17, wherein the organoalkoxysilane is present in an amount of 0.5-40 wt. % relative to the total weight of the polymer.

33. The moisture-curing composition according to claim 32, wherein the organoalkoxysilane is present in an amount of 2-30 wt. % relative to the total weight of the polymer.

34. The moisture-curing composition according to claim 32, wherein the organoalkoxysilane is present in an amount of 4-20 wt. % relative to the total weight of the polymer.

35. An adhesive comprising the composition according to claim 16.

36. A sealant comprising the composition according to claim 16.

37. A paint comprising the composition according to claim 16.

38. A lacquer comprising the composition according to claim 16.

39. A primer comprising the composition according to claim 16.

40. A seal comprising the composition according to claim 16.

41. A protective coating comprising the composition according to claim 16.

42. A floor covering comprising the composition according to claim 16.

43. A bonded article comprising a first substrate and a second substrate that are bonded using the composition according to claim 16, wherein the first substrate and the second substrate are made of different or identical materials.

44. The bonded article according to claim 43, wherein the article is a means of transport.

45. The bonded article according to claim 43, wherein the bonded article is a land or water vehicle.

46. The bonded article according to claim 43, wherein the bonded article is an automobile, a bus, a freight vehicle, a train, or a ship, or a portion thereof.

47. A sealed article comprising a first substrate and a second substrate, wherein the composition according to claim 16 is applied between a surface of the first substrate and a surface of the second substrate to form the sealed article, and the first substrate and the second substrate are made of different or identical materials.

48. A sealed article according to claim 47, wherein the sealed article is a means of transport or a structure.