Compounds having guanidine groups and containing semi-organic silicon groups

Patent metadata

Field	Value
Publication number	US-9353225-B2
Application number	US-201414457933-A
Country	US
Kind code	B2
Filing date	Aug 12, 2014
Priority date	Aug 23, 2013
Publication date	May 31, 2016
Grant date	May 31, 2016

Abstract

This invention relates to compounds having guanidine groups and containing semi-organic silicon groups, their use for the curing of compounds containing alkoxysilyl groups, compositions comprising the curing catalysts of the invention, and use of the compositions as adhesives and sealants and also as coating materials.

First claim

The invention claimed is:

1. A compound having guanidine groups and containing semi-organic silicon groups, of the formula (I):
M a M G b D c D G d T e Q f   (I);

where:
a =0 to 10;
b =0 to 10;
c =0 to 350;
d =0 to 50;
e =0 to 50;
f =0 to 10;
where the sum of the indices b and d is greater than or equal to 1 to 20;
with the proviso that:
when the index a is 2 and at the same time the sum of the indices b, c, e, and f is zero, the index d is other than 1; or
when the sum of the indices a, c, d, e, and f is zero, the index b is 2; and

where:
M=[R 3 SiO 1/2 ];
M G =[R G R 2 SiO 1/2 ];
D=[R 2 SiO 2/2 ];
D G =[R G 2 SiO 2/2 ];
T=[RSiO 3/2 ];
Q=[SiO 4/2 ];
R are, independently of one another, identical or different and are OR 2 groups and/or linear or branched, saturated or else mono- or polyunsaturated hydrocarbon radicals, which may be interrupted by heteroatoms and/or may be substituted one or more times by hydroxyl, amino, carboxyl or aryl radicals;
where R a is identical or different and is hydrogen and/or alkyl groups having 1 to 12 carbon atoms; and

R G is a radical containing guanidine groups and selected from the group consisting of the formulas (IIa), (IIb), and (IIc), and tautomers and salts thereof:

 where:
R 3 are divalent radicals which, independently of one another, are identical or different, linear or branched hydrocarbon radicals containing 1 to 50 carbon atoms, and may be interrupted by heteroatoms, and/or which may be substituted one or more times by hydroxyl or amino radicals; and
R 11 , R 12 , R 21 , R 22 , and R 31 are, independently of one another, identical or different and are hydrogen, linear or branched or cyclic hydrocarbons containing 1 to 15 carbon atoms, it being possible for the hydrocarbons also to contain 1 or 2 heteroatoms, preferred heteroatoms being nitrogen, oxygen and silicon;

wherein at least one R G in the formula (I) is of the formula (IIa) or (IIb).

2. The compound according to claim 1 ;
wherein:
the sum of the indices a, c, d, e and f is zero; and
the index b is 2.

3. The compound according to claim 1 ;
wherein the index d is 1 to 4.

4. A method comprising:
utilizing compounds having guanidine groups and containing semi-organic silicon groups according to claim 1 to cure compounds containing alkoxysilyl groups.

5. The method according to claim 4 ;
wherein the compound containing alkoxysilyl groups are polymers of the formula (III):
P(SiX w Y (3-w) ) p   (III);

 where:
P may be any desired polymer;
X is an alkoxy radical having 1 to 8 carbon atoms;
Y is an alkyl radical;
w is an index from 1 to 3; and
p is 1 to 100.

6. A compound having guanidine groups and containing semi-organic silicon groups, of the formula (I):
M a M G b D c D G d T e Q f   (I);

where:
a =0;
b =0;
c 0 to 7;
d =1 to 8;
e =0;
f =0;
wherein the sum of the indices c +d is from 3 to 8;

where:
D=[R 2 SiO 2/2 ];
D G =[R G 2 SiO 2/2 ];
R is an OR a group, or a linear or branched, saturated or else mono- or polyunsaturated hydrocarbon radical, which may be interrupted by heteroatoms and/or may be substituted one or more times by hydroxyl, amino, carboxyl, or aryl radicals;
where R a is hydrogen or an alkyl group having 1 to 12 carbon atoms; and

R G is a radical containing guanidine groups and selected from the group consisting of the formulas (IIa), (IIb), and (IIc), and tautomers and salts thereof:

 where:
R 3 are divalent radicals which, independently of one another, are identical or different, linear or branched hydrocarbon radicals containing 1 to 50 carbon atoms, and may be interrupted by heteroatoms, and/or which may be substituted one or more times by hydroxyl or amino radicals; and
R 11 , R 12 , R 21 , R 22 , and R 31 are, independently of one another, identical or different and are hydrogen, linear or branched or cyclic hydrocarbons containing 1 to 15 carbon atoms, it being possible for the hydrocarbons also to contain 1 or 2 heteroatoms, preferred heteroatoms being nitrogen, oxygen and silicon.

7. A composition comprising:
(a) at least one compound having guanidine groups and containing semi-organic silicon groups; and
(b) at least one compound containing alkoxysilyl groups of the formula (III):
P(SiX w Y (3-w) ) p   (III);

 where:
P may be any desired polymer;
X is an alkoxy radical having 1 to 8 carbon atoms;
Y is an alkyl radical;
w is an index from 1 to 3 and
p is 1 to 100;

wherein the polymers of formula (III) containing alkoxysilyl groups comprise oxypropylene units.

8. The composition according to claim 7 ;
wherein the compounds of (a) are silanes and/or siloxanes having guanidine groups.

9. The composition according to claim 8 , further comprising:
additives as well as the components (a) and (b).

10. The composition according to claim 7 ;
wherein the siloxanes of (a) are compounds having guanidine groups and containing semi-organic silicon groups of the formula (I):
M a M G b D c D G d T e Q f   (I);

wherein:
a =0 to 10;
b =0 to 10;
c =0 to 350;
d =0 to 50;
e =0 to 50;
f =0 to 10;
where the sum of the indices b and d is greater than or equal to 1 to 20;
with the proviso that:
when the index a is 2 and at the same time the sum of the indices b, c, e, and f is zero, the index d is other than 1; or
when the sum of the indices a, c, d, e, and f is zero, the index b is greater than 1; and

wherein:
M=[R 3 SiO 1/2 ];
M G =[R G R 2 SiO 1/2 ];
D=[R 2 SiO 2/2 ];
D G =[R G 2 SiO 2/2 ];
T=[RSiO 3/2 ];
Q=[SiO 4/2 ];
R are, independently of one another, identical or different and are OR 2 groups and/or linear or branched, saturated or else mono- or polyunsaturated hydrocarbon radicals, which may be interrupted by heteroatoms and/or may be substituted one or more times by hydroxyl, amino, carboxyl or aryl radicals;
where R a is identical or different and is hydrogen and/or alkyl groups having 1 to 12 carbon atoms; and

R G is a radical containing guanidine groups and selected from the group consisting of the formulas (IIa), (IIb), and (IIc), and tautomers and salts thereof:

 where:
R 3 are divalent radicals which, independently of one another, are identical or different, linear or branched hydrocarbon radicals containing 1 to 50 carbon atoms, and may be interrupted by heteroatoms, and/or which may be substituted one or more times by hydroxyl or amino radicals; and
R 11 , R 12 , R 21 , R 22 , and R 31 are, independently of one another, identical or different and are hydrogen, linear or branched or cyclic hydrocarbons containing 1 to 15 carbon atoms, it being possible for the hydrocarbons also to contain 1 or 2 heteroatoms, preferred heteroatoms being nitrogen, oxygen and silicon.

11. An adhesive or sealant comprising:
the composition according to claim 7 .

12. A coating material comprising: the composition according to claim 7 .

13. A method comprising:
utilizing at least one compound according to claim 1 to cure compounds containing alkoxysilyl groups by forming Si—O—Si bonds.

14. The method according to claim 13 ;
wherein the curing of compounds containing alkoxysilyl groups is carrie

Assignees

• Evonik Degussa Gmbh

Inventors

• Knott Wilfried
• Ferenz Michael
• Fiedel Michael
• Hojak Wolfgang
• Brugger Bastian Matthias
• Schubert Frank
• Lewin Anke

Classifications

• C09D183/04

  Polysiloxanes · CPC title

• C07F7/21

  Cyclic compounds having at least one ring containing silicon, but no carbon in the ring · CPC title

• C09D183/08

  containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen · CPC title

• C08G77/18

  to alkoxy or aryloxy groups · CPC title

• C09J183/08

  containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen · CPC title