Amine epoxy resin adduct

Patent metadata

Field	Value
Publication number	US-12516148-B2
Application number	US-202117785553-A
Country	US
Kind code	B2
Filing date	Feb 22, 2021
Priority date	Feb 24, 2020
Publication date	Jan 6, 2026
Grant date	Jan 6, 2026

Abstract

An amine-functional adduct from the reaction of an amine mixture containing at least one diamine of formula (I) and at least one diamine of formula (II) in a weight ratio ranging from 65/35 to 95/5 with at least one diepoxide in a stoichiometric ratio of at least 1.2 moles of diamine of the formula (I) to 1 mole equivalent of epoxide groups. The adduct is liquid at room temperature without diluent even in the presence of a small excess of diamine and is surprisingly low in viscosity. In addition, it is particularly cost-effective, as it is available from an amine mixture that is technically easy to produce. The adduct enables low-emission or emission-free epoxy resin coatings with surprisingly good workability at surprisingly fast curing, which have a high hardness and low tendency to yellowing, and which hardly tend to blushing-related defects even in cold and humid conditions.

First claim

The invention claimed is:

1 . An amine-functional adduct from the reaction of
(i) an amine mixture comprising at least one diamine of formula (I) and at least one diamine of formula (II) in a weight ratio within a range from 65/35 to 95/5,

where
A is an alkylene radical, cycloalkylene radical or arylalkylene radical having 2 to 12 carbon atoms, and
R is an alkyl radical, cycloalkyl radical or arylalkyl radical having 1 to 12 carbon atoms, wherein the two nitrogen atoms in the diamine of formula (I) and (II) are in each case separated from one another by at least two carbon atoms and the diamine of formula (I) has a total of 8 to 15 carbon atoms,
(ii) with at least one diepoxide

in a stoichiometric ratio of at least 1.2 moles of diamine of formula (I) to 1 mole equivalent of epoxy groups,
wherein the amine mixture used for production of the adduct has a content of diamine of formula H 2 N-A-NH 2 of not more than 5% by weight.

2 . The adduct as claimed in claim 1 , wherein the radicals A and R in the diamines of formulas (I) and (II) are identical radicals.

3 . The adduct as claimed in claim 1 , wherein the diamine of formula (I) is N-benzylethane-1,2-diamine and the diamine of formula (II) is N,N′-dibenzylethane-1,2-diamine.

4 . The adduct as claimed in claim 1 , wherein the weight ratio between the diamine of formula (I) and the diamine of formula (II) is within a range from 70/30 to 95/5.

5 . The adduct as claimed in claim 1 , wherein the amine mixture is a reaction product from the reductive alkylation of at least one amine of formula H 2 N-A-NH 2 with at least one aldehyde or ketone and hydrogen.

6 . The adduct as claimed in claim 1 , wherein the diepoxide is an aromatic diepoxide.

7 . The adduct as claimed in claim 1 , wherein the stoichiometric ratio is within a range from 1.3 to 2, moles of diamine of formula (I) to 1 molar equivalent of epoxy groups of the diepoxide.

8 . The adduct as claimed in claim 7 , wherein it contains 2:1 adducts derived from 2 moles of diamine of formula (I) or (II) and 1 mole of diepoxide, and higher adducts selected from the group consisting of one or more of 3:2 adducts derived from 3 moles of diamine of formula (I) or (II) and 2 moles of diepoxide, 4:3 adducts derived from 4 moles of diamine of formula (I) or (II) and 3 moles of diepoxide and 5:4 adducts derived from 5 moles of diamine of formula (I) or (II) and 4 moles of diepoxide, wherein a weight ratio of the 2:1 adducts to the higher adducts is within a range from 30/70 to 80/20.

9 . The adduct as claimed in claim 1 , wherein it contains less than 1% by weight of thinner or water.

10 . A curing agent for epoxy resins comprising the adduct as claimed in claim 1 and at least one further constituent selected from the group consisting of further amines, accelerators, and thinners.

11 . The curing agent for epoxy resins as claimed in claim 10 , wherein at least one further amine having aliphatic amino groups and at least three amine hydrogens is present that was not present during the preparation of the adduct.

12 . The curing agent for epoxy resins as claimed in claim 10 , wherein the further amine is selected from the group consisting of N-benzylethane-1,2-diamine, 2,2 (4),4-trimethylhexane-1,6-diamine, 1,2-diaminocyclohexane, 1,3-bis(aminomethyl) cyclohexane, 1,4-bis(aminomethyl) cyclohexane, 1-amino-3-aminomethyl-3,5,5-trimethylcyclohexane, 2 (4)-methyl-1,3-diaminocyclohexane, 1,3-bis(aminomethyl) benzene, polyoxypropylene diamines having an average molecular weight M n within a range from 200 to 500 g/mol, and polyoxypropylene triamines having an average molecular weight M n within a range from 300 to 500 g/mol is present.

13 . An epoxy resin composition comprising
a resin component comprising at least one epoxy resin and a curing agent component comprising the adduct as claimed in claim 1 .

14 . A coating, primer, adhesive, sealant, potting compound, casting resin, impregnating resin, or matrix for fiber composites, comprising the epoxy resin composition as claimed in claim 13 .

15 . An article obtained from claim 14 .

Assignees

• Sika Tech Ag

Inventors

• Kasemi Edis
• Sarioglu Oguz
• Burckhardt Urs
• Kramer Andreas
• Stadelmann Ursula
• Grötzinger Jochen
• Von Der Brüggen Uwe

Classifications

• C08G2190/00

  Compositions for sealing or packing joints · CPC title

• C08G2170/00

  Compositions for adhesives · CPC title

• C08G2150/00

  Compositions for coatings · CPC title

• C08G59/5033

  aromatic · CPC title

• C08G59/245

  aromatic · CPC title