Modified alkoxylation products which have alkoxysilyl groups and contain urethane groups, and their use

Patent metadata

Field	Value
Publication number	US-9334354-B2
Application number	US-201414332838-A
Country	US
Kind code	B2
Filing date	Jul 16, 2014
Priority date	Aug 23, 2013
Publication date	May 10, 2016
Grant date	May 10, 2016

Abstract

The invention relates to alkoxylation products, their preparation, compositions comprising the alkoxylation products of the invention, and the use thereof as or for producing adhesives and sealants.

First claim

The invention claimed is:

1. An alkoxylation product which comprises the structural elements of the formula (I)
M i D j T k Q l UR u AP v   formula (I)

wherein M, D, T and Q are linked not to one another but instead with one another via the groups UR and/or AP, and the groups UR and AP are not linked to one another,
i=1 to 16,
j=0 to 10,
k=0 to 6,
l=0 to 4,
u=1 to 17,
v=0 to 6,
M radicals independently of one another are identical or different radicals from the following group:
a) —NH—R 12   formula (IVa),

b) —NR 12 2   formula (IVb),

c) —OR 12   formula (IVc) and

d)

where
R 1 =independently at each occurrence a saturated or unsaturated, linear or branched organic hydrocarbon radical which may contain O, S and/or 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 or an alkyl group having 1 to 8 carbon atoms,
R 5 =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 6 and R 7 =independently at each occurrence the same as R 5 and/or alkoxy,
R 11 =independently at each occurrence a saturated or unsaturated alkyl group having 1 to 24 carbon atoms, whose chain may be interrupted by oxygen and may further carry functional groups;
a=0 to 1000,
b=0 to 1000,
c=0 to 1000,
d=0 to 1000,
with the proviso that the groups having the indices a, b, c and d are freely permutable over the molecular chain,
e=1 to 10,
g+f=3 and g is at least 1,
h=0 to 10,
where the different monomer units both of the fragments having the indices a, b, c and d and of the polyoxyalkylene chain of the substituent R 1 may be constructed in blocks with one another or else may be subject to a statistical distribution and, moreover, are freely permutable with one another,
with the proviso that at least 10 mol % of the radicals M, based on the total amount of the radicals M, conform to —NH—R 12 of the formula (IVa) and/or —NR 12 2 of the formula (IVb),
where for the formulae (IVa), (IVb) and (IVc):
R 12 of the formulae (IVa), (IVb) and (IVc) are independently of one another identical or different, optionally substituted hydrocarbon radicals which are interrupted by heteroatoms or are optionally substituted hydrocarbon radicals having 1 to 30 C atoms,
D is a polyether radical -(D A ) t D X where t is 2,
T is a polyether radical -(D A ) t D X where t is 3 and
Q is a polyether radical -(D A ) t D X where t is 4,
where
D X is a t-valent functional, saturated or unsaturated, linear or branched organic hydrocarbon radical which may contain O, S, Si and/or N as heteroatoms, and
D A is a fragment of the formula (II)

where a to h and R 2 to R 7 and R 11 are defined as in formula (Ia), and with the proviso that the sum total of all indices b of the formulae (Ia) and (II) makes at least 1, and the sum total of all indices a of the formulae (Ia) and (II) makes at least 1,
UR is a divalent radical of the form —U-D C -U—, where U is a —C(O)—NH group which is bonded via the nitrogen to D C , where D C is a divalent hydrocarbon radical,
AP are independently of one another identical or different radicals of the general formula (IIIa) or (IIIb)

2. The alkoxylation products according to claim 1 , wherein k and l are zero.

3. The alkoxylation products according to claim 1 , wherein formula (Ia) a=0.

4. The alkoxylation products according to claim 1 , wherein the sum total of all indices a from formula (Ia) and formula (II) makes at least 2, and/or the sum total of all indices b from formula (Ia) and formula (II) makes at least 3.

5. The alkoxylation products according to claim 1 , wherein at least 25 mol % of the radicals M, based on the total amount of the radicals M, conform to —NH—R 12 of the formula (IVa) and/or —NR 12 2 of the formula (IVb).

6. A process for preparing alkoxylation products comprising reacting polyethers carrying OH groups, with polyfunctional isocyanates and with compounds of the formula H—NH—R 12 2 as per formula (IVa) and/or H—NR 12 2 as per formula (IVb).

7. The process according to claim 6 , wherein the polyfunctional isocyanates are diisocyanates.

8. The process according to claim 6 , wherein in the compounds of the formula H—NH—R 12 2 as per formula (IVa) and/or H—NR 12 2 as per formula (IVb), at least one compound is used which is selected from ethylamine, diethylamine, propylamine, dipropylamine, butylamine, dibutylamine, dicyclohexylamine, dihexylamine, 2-ethylhexylamine, di(2-ethylhexyl)amine, ditridecylamine, aniline, 1-phenylethylamine, 2,6-xylidene, 2-phenylethylamine, benzylamine, toluidine, 2-methoxyethylamine, 3-methoxypropylamine, di(2-methoxyethyl)amine, 2-(diethylamino)ethylamine, 3-(dimethylamino)-1-propylamine, bis[(3-dimethylamino)propyl]amine, N-(3-aminopropyl)imidazole and amino-functional polyethers.

9. The process according to claim 6 , wherein in a first reaction step (a) polyethers of the formula (HD A ) t D X are reacted with diisocyanates and in a second reaction step (b) the product of the first reaction step (a) is reacted with a molecule of the formula H-M, where -(D A ) t D X and M are defined as in claim 1 .

10. The process according to claim 6 , wherein the diisocyanates are used in a molar excess relative to the polyethers (HD A ) t D X .

11. The process according to claim 6 , further comprising adding at least one further component which is selected from catalysts, polyethers (HD A ) t D X , diisocyanates and/or molecules of the formula H-M after the first reaction step (a) and/or after the second reaction step (b).

12. A composition comprising the alkoxylation products according to claim 1 .

13. The composition according to claim 12 , further comprising at least one curing catalyst.

14. The composition according to claim 12 , further comprising at least one adjuvant selected from the group of diluents, catalysts, plasticizers, fillers, solvents, emulsifiers, adhesion promoters, rheology additives, additives for chemical drying, and/or stabilizers against thermal and/or chemical exposures and/or exposures to ultraviolet and visible light, thixotropic agents, flame retardants, blowing agents or defoamers, deaerating agents, film-forming polymers, antimicrobial and preservative substances, antioxidants, dyes, colorants and pigments, frost preventatives, fungicides, reactive diluents, complexing agents, wetting agents, co-crosslinkers, spraying assistants, vitamins, growth substances, hormones, active pharmacological ingredients, fragrances, radical scavengers and/or other adjuvants.

15. A method of utilizing the alkoxylation products, as claimed in claim 1 for producing adhesives or sealants or coating materials, shaped articles, liquid pastes, powder coating curing agents, particles, fabrics or c

Assignees

• Evonik Industries Ag
• Evonik Degussa Gmbh

Inventors

• Ferenz Michael
• Lobert Matthias
• Schubert Frank
• Lewin Anke
• Zellmer Volker
• Knott Wilfried
• Roessing Melanie

Classifications

• C08G18/48

  Polyethers · CPC title

• C08G65/33303

  containing amino group · CPC title

• C08J2375/08

  from polyethers · CPC title

• C08G65/336

  containing silicon · CPC title

• C08J9/00

  Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof (mechanical aspects of shaping of plastics or substances in a plastic state for the production of porous or cellular articles B29C) · CPC title