Alkoxysilane-functionalized allophanates

Patent metadata

Field	Value
Publication number	US-10093765-B2
Application number	US-201715622159-A
Country	US
Kind code	B2
Filing date	Jun 14, 2017
Priority date	Jun 27, 2016
Publication date	Oct 9, 2018
Grant date	Oct 9, 2018

Abstract

The present invention relates to alkoxysilane-functionalized allophanates, to methods for production thereof, and to the use thereof. In particular, the alkoxysilane-functionalized allophanate includes the reaction product of A) at least one alkoxysilane group-containing monourethane A) of the formula 1

R n (OR 1 ) 3-n Si—R 2 —NH—(C═O)—OR 3   formula 1,

where R, R 1 , R 2 and R 3 are each independently hydrocarbyl radicals having 1-8 carbon atoms, which may be linear, branched or cyclic, or else may be integrated together to form a cyclic system, and n is 0-2, and B) at least one diisocyanate B), in a molar ratio of A) to B) of 3:1 to 1.5:1.

First claim

The invention claimed is:

1. An alkoxysilane-functionalized allophanate comprising the reaction product of
A) at least one alkoxysilane group-containing monourethane A) of the formula 1
R n (OR 1 ) 3-n Si—R 2 —NH—(C═O)—OR 3   formula 1,

where R, R 1 , R 2 and R 3 are each independently hydrocarbyl radicals having 1-8 carbon atoms, which may be linear, branched or cyclic, or else may be integrated together to form a cyclic system, and n is 0-2,
and
B) at least one diisocyanate B),
in a molar ratio of A) to B) of 3:1 to 1.5:1.

2. The alkoxysilane-functionalized allophanate according to claim 1 , wherein the molar ratio of A) to B) is from 2.5:1 to 1.8:1.

3. The alkoxysilane-functionalized allophanate according to claim 1 , wherein R, R 1 , R 2 and R 3 are at the same time or each independently methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl or tert-butyl.

4. The alkoxysilane-functionalized allophanate according to claim 1 , wherein n is 0, R 1 and R 3 are at the same time or each independently methyl or ethyl, and R 2 is at the same time or mutually independently methyl or propyl.

5. The alkoxysilane-functionalized allophanate according to claim 1 , wherein n is 0 and R 2 is methyl or propyl, and R 1 is methyl or ethyl and R 3 ═R 1 .

6. The alkoxysilane-functionalized allophanate according to claim 1 , wherein n is 0, R 1 and R 3 are methyl and R 2 is propyl.

7. The alkoxysilane-functionalized allophanate according to claim 1 , wherein the diisocyanate B) is selected from isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), 2,2-di cyclohexylmethane diisocyanate (2,2′-H12MDI), 2,4′-dicyclohexylmethane diisocyanate (2,4′-H12MDI), 4,4′-dicyclohexylmethane diisocyanate (4,4′-H12MDI), 2-methylpentane diisocyanate (MPDI), pentane diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate (2,2,4-TMDI), 2,4,4-trimethylhexamethylene diisocyanate (2,4,4-TMDI), norbornane diisocyanate (NBDI), methylenediphenyl diisocyanate (MDI), toluidine diisocyanate (TDI), tetramethylxylylene diisocyanate (TMXDI), xylylene diisocyanate (MXDI), individually or in a mixture.

8. The alkoxysilane-functionalized allophanate according to claim 1 , wherein the diisocyanate B) is selected from IPDI, 4,4′-H12MDI, HDI and mixtures of 2,2,4-TMDI and 2,4,4-TMDI, individually or in a mixture.

9. A composition, which may be coating compositions and paint compositions for metal, plastic, glass, wood, MDF (Middle Density Fibreboards) or leather substrates or other heat-resistant substrates, the composition comprising the alkoxysilane-functionalized allophanates according to claim 1 .

10. An adhesive composition for bonding of metal, plastic, glass, wood, MDF or leather substrates or other heat-resistant substrates, the adhesive composition comprising the alkoxysilane-functionalized allophanates according to claim 1 .

11. A coating composition, adhesives or sealant, comprising at least one alkoxysilane-functionalized allophanate according to claim 1 .

12. An alkoxysilane-functionalized allophanate, obtained by reacting
A) at least one alkoxysilane group-containing monourethane A) of the formula 1
R n (OR 1 ) 3-n Si—R 2 —NH—(C═O)—OR 3   formula 1,

where R, R 1 , R 2 and R 3 are each independently hydrocarbyl radicals having 1-8 carbon atoms, which may be linear, branched or cyclic, or else may be integrated together to form a cyclic system, and n is 0-2,
and
B) at least one diisocyanate B),
in a molar ratio of A) to B) of from 3:1 to 1.5:1;
C) optionally in the presence of at least one catalyst C),
and
D) optional reaction of the residual amount of NCO groups of B) with an alcohol D).

13. The alkoxysilane-functionalized allophanate according to claim 12 , wherein the component c) is selected from the group consisting of metal carboxylates, tert-amines, amidine, guanidine, quaternary ammonium salts, tetraalkylammonium salts, quaternary phosphonium salts, metal acetylacetonates, quaternary ammonium acetylacetonates, quaternary phosphonium acetylacetonates, alone or in a mixture.

14. The alkoxysilane-functionalized allophanate according to claim 12 , wherein the component c) is zinc acetylacetonate and/or zinc ethylhexanoate.

15. The alkoxysilane-functionalized allophanate according to claim 12 , wherein the alcohol D) is selected from methanol, ethanol, propanol, isopropanol, 1-butanol, 2-butanol, pentanol, ethyl-2-hexanol, 1-hexanol.

16. A method for preparing alkoxysilane-functionalized allophanates according to claim 12 , by reacting
A) at least one alkoxysilane group-containing monourethane A) of the formula 1
R n (OR 1 ) 3-n Si—R 2 —NH—(C═O)—OR 3   formula 1,

where R, R 1 , R 2 and R 3 are each independently hydrocarbyl radicals having 1-8 carbon atoms, which may be linear, branched or cyclic, or else may be integrated together to form a cyclic system, and n is 0-2,
and
B) at least one diisocyanate B),
in a molar ratio of A) to B) of from 3:1 to 1.5:1;
C) optionally in the presence of at least one catalyst C),
and
D) optional reaction of the residual amount of NCO groups of B) with an alcohol D).

17. The method according to claim 16 , wherein the reaction is carried out at temperatures in the range from 15 to 40° C.

18. The method according to claim 16 , wherein the reaction is carried out at temperatures in the range from 80 to 220° C.

19. The method according to claim 16 , wherein the reaction of the residual amount of NCO groups of B) with an alcohol D) is carried out at temperatures in the range of 30-150° C.

20. The method according to claim 16 , wherein the reaction is carried out in the presence of zinc acetylacetonate and/or zinc ethylhexanoate as catalyst C).

21. The method according to claim 16 , wherein the residual amount of NCO groups of B) is reacted with an alcohol D) at the ratio of the NCO groups to OH groups of the alcohol D) of from 0.8:1 to 1.2:1.

Assignees

• Evonik Degussa Gmbh

Inventors

• Stache Wiebke
• Unkelhäusser Tobias
• Spyrou Emmanouil
• Lilienthal Annegret
• Brückner Iris
• Pfingsten Jan

Classifications

• C08G18/718

  containing silicon · CPC title

• C08G18/7837

  containing allophanate groups · CPC title

• C07F7/1872

  Preparation; Treatments not provided for in C07F7/20 · CPC title

• C08G18/10

  Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step · CPC title

• C08G18/222

  metal compounds not provided for in groups C08G18/225 - C08G18/26 · CPC title