Alkoxysilyl-containing adhesive sealants with intrinsically reduced viscosity

Patent metadata

Field	Value
Publication number	US-9896534-B2
Application number	US-201415101819-A
Country	US
Kind code	B2
Filing date	Nov 26, 2014
Priority date	Dec 3, 2013
Publication date	Feb 20, 2018
Grant date	Feb 20, 2018

Abstract

The present invention provides specific alkoxylation products, a process for preparing them, compositions comprising these alkoxylation products, and their use.

First claim

The invention claimed is:

1. A composition comprising alkoxylation product mixtures with intrinsically reduced viscosity, obtained by alkoxylation of epoxy-functional compounds in the presence of at least two different OH-functional starters, a starter (1) and a starter (2),
wherein the starter (1) has a molar mass of greater than 400 g/mol and the starter (2) has a molar mass of less than or equal to 400 g/mol, wherein the epoxy functional compounds comprise an epoxide carrying an alkoxysilyl group, an alkoxysilylalkyl glycidyl ether group, or both.

2. The composition according to claim 1 , wherein the molar mass of the starter (1) exceeds the molar mass of the starter (2) by at least 200 g/mol.

3. The composition according to claim 1 , wherein the molar mass of the starter (1) exceeds the molar mass of the starter (2) by at least 600 g/mol.

4. The composition according to claim 1 , wherein the starter (1) has t OH groups and the starter (2) has t−1 OH groups, wherein t=2 to 8.

5. The composition according to claim 1 , wherein the alkoxylation products (1) from the starter (1) are obtained from alkylene oxide, from at least one epoxide carrying alkoxysilyl groups, and optionally from further monomers, and the alkoxylation products (2) from the starter (2) are obtained from alkylene oxide and optionally from at least one epoxide carrying alkoxylsilyl groups, from further monomers, or both.

6. The composition according to claim 5 , wherein the starter 1 is polypropylene glycol, the starter 2 is selected from the group consisting of 1-butanol, 2-propyl-1-heptanol, 2-ethyl-1-hexanol, and 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate, the alkylene oxide is propylene oxide, and the epoxide carrying alkoxysilyl is (3-glycidyloxypropyl)triethoxysilane, and
wherein the composition has an intrinsic viscosity of less than 10 Pa·s at 25° C.

7. The composition according to claim 1 , wherein the alkoxylation products (1) from the starter (1) are obtained from ethylene oxide, propylene oxide, or both, from at least one alkoxysilylalkyl glycidyl ether and optionally from further monomers, and the alkoxylation products (2) from the starter (2) are obtained from ethylene oxide, propylene oxide, or both, and from at least one alkoxysilylalkyl glycidyl ether, from further monomers or both.

8. The composition according to claim 1 , wherein the alkoxylation products (1) are obtained from the following monomer fractions, comprising:
10 to 97 wt % of propylene oxide, 0 to 60 wt % of ethylene oxide, 0 to 25 wt % of alkoxysilylalkyl glycidyl ethers and 0 to 25 wt % of further monomers, based on the total weight of the alkoxylation products (1); and
the alkoxylation products (2) are obtained from the following monomer fractions, comprising:
10 to 97 wt % of propylene oxide, 0 to 60 wt % of ethylene oxide, 0 to 25 wt % of alkoxysiylalkyl glycidyl ethers and 0 to 25 wt % of further monomers, based on the total weight of the alkoxylation products (2).

9. The composition according to claim 8 , wherein the alkoxylation products (1), the alkoxylation products (2) or both are obtained from monomer fractions comprising 0.1 to 25 wt % of alkoxysilylalkyl glycidyl ethers based on the total weight of the alkoxylation products.

10. The composition according to claim 1 , wherein the starter (1) is selected from the group consisting of polyetherols, polycarbonate polyols, polyethercarbonates, and mixtures thereof.

11. The composition according to claim 1 , wherein the starter (2) is selected from the group consisting of butanol, ethanol, ethylhexanol, and mixtures thereof.

12. The composition according to claim 1 , wherein the composition comprises at least an alkoxylation product (1) and an alkoxylation product (2), wherein the alkoxylation product (1) obtained by the starter (1) conforms to formula (I) and the alkoxylation product (2) obtained by the starter (2) conforms to formula (IIa):
M i D j T k Q l UR u AP v   formula (I)

wherein fragments M, D, T, and Q are linked not to one another but instead with one another via the groups UR, AP, or both and the groups UR and AP are not linked to one another but are linked with one another via fragments M, D, T, or Q, wherein
i=0 to 16,
j=0 to 10,
k=0 to 6,
l=0 to 4,
u=0 to 17, and
v=0 to 6,
with the proviso that i+j+k+1 is greater than or equal to 1,
M independently at each occurrence is an oxygen-radical carrying hydrocarbon radical having a minimum numerical molar mass of 32 g/mol, which may optionally be interrupted by heteroatoms,
Or is a radical of the formula (Ia) or of the formula (Ib) or of the formula (Ic) with

wherein
a=0 to 100,
b=1 to 1000,
c=0 to 200,
d=0 to 200,
m is an integer from 0 to 200,
n is an integer from 0 to 500,
e=1 to 10,
f=0 to 2
g=1 to 3
with the proviso that g+f=3 and g is at least 1, and
h=0 to 10
with the proviso that the various monomer units of the fragments with the indices a, b, c, d, w, and y may be constructed blockwise among one another or else are subject to a statistical distribution and are freely permutable among one another, it being disallowed for each of the groups with the indices w and y to follow itself or the other respective group, and
wherein
R 1 =independently at each occurrence a saturated or unsaturated, linear or branched organic hydrocarbon radical which may contain at least one of O, S and N as heteroatoms,
R 2 =independently at each occurrence an alkyl group having 1 to 8 carbon atoms,
R 3 =independently at each occurrence an alkyl group having 1 to 8 carbon atoms,
R 4 =independently at each occurrence a hydrogen radical, an alkyl group having 1 to 20 carbon atoms, or an aryl or alkaryl group, or
R 4 and one of the radicals R 5 may together form a ring which includes the atoms to which R 4 and R 5 are bonded,
R 5 =independently at each occurrence a hydrogen radical or an alkyl group having 1 to 8 carbon atoms,
R 6 , R 7 =independently at each occurrence a hydrogen radical, an alkyl group having 1 to 20 carbon atoms, or at least one of an aryl or alkaryl group, and an alkoxy group,
R 11 =independently at each occurrence a saturated or unsaturated, aliphatic or aromatic hydrocarbon radical having 2 to 30 C atoms, which is optionally substituted,
R 13 , R 14 =independently at each occurrence hydrogen, an organic radical, or both, or else optionally R 13 , R 14 , or both may be absent, and, if R 13 and R 14 are absent, there is a C═C double bond in place of the radicals R 13 and R 14 ,
the bridging fragment Z may be present or absent;
if the bridging fragment Z is absent, then
R 15 , R 16 =independently at each occurrence hydrogen, and/or an organic radical, or both, and, if one of the radicals R 13 or R 14 is absent, the respective germinal radical, R 15 if R 13 is absent and R 16 if R 14 is absent, is an alkylidene radical,
if the bridging fragment Z is present, then
R 15 and R 16 =hydrocarbon radicals which are bridged cycloaliphatically or aromatically via the fragment Z, Z representing a divalent alkylene or alkenylene radical which may be further substituted,

wherein
R 17 =independently at each occurrence a linear or branched, saturated or unsaturated, optionally further-substituted alkyl group ha

Assignees

• Evonik Degussa Gmbh

Inventors

• Lobert Matthias
• Lewin Anke
• Ferenz Michael
• Schubert Frank

Classifications

• C08G18/5096 Primary

  containing silicon · CPC title

• C09J175/08

  from polyethers · CPC title

• C08G18/755

  and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate · CPC title

• C08G18/4808

  Mixtures of two or more polyetherdiols · CPC title

• C08G65/2639

  the other compounds containing elements other than oxygen, nitrogen or sulfur · CPC title