IP Library › Granted Patent US 11,485,887
Granted Patent B2
US 11,485,887 · App. 16/772,500 · Granted Nov 1, 2022

Light-fixable and heat-curing compounds based on epoxy resins and thiols

Inventors: Andreas Zillessen (Augsburg, DE); Sabrina Roediger (Herrsching, DE); Bastian Sueveges (Windach, DE); Robert Born (Gilching, DE)
Assignee: DELO INDUSTRIE KLEBSTOFFE GMBH & CO. KGAA
C09J163/00C08G59/184C08G59/245C08G59/66C08K3/36C08K5/13C08K5/43C08K13/02C09D7/61C09D7/63C09D163/00C09J11/04C09J11/06C09K3/10C08F222/102C08F222/1063C09K2200/0247C09K2200/0488C09K2200/0647
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Quick Facts
Patent No.
US 11,485,887
App. No.
16/772,500
Granted
Nov 1, 2022
Kind
B2
Abstract

The invention relates to a composition that is liquid at room temperature, can be fixed by radiation and cured by heat, comprising the following components: (A) an at least bifunctional epoxy-containing compound; (B) an at least bifunctional thiol; (C) a radiation-curable compound; (D) a photoinitiator; (E) a stabilizer blend that contains at least one sulfonyl isocyanate and at least one acid; and (F) a nitrogen compound as an accelerator. The compositions are processable at room temperature over a period of at least 24 h and can be completely cured even at low temperatures.

Claims (40)

1. A one-pack composition that is liquid at room temperature, can be fixed by radiation and cured by heat, comprising:

(A) an at least bifunctional epoxy-containing compound;

(B) an at least bifunctional thiol;

(C) a radiation-curable compound;

(D) a photoinitiator;

(E) a stabilizer blend that contains (E1) at least one sulfonyl isocyanate and (E2) at least one acid; and

(F) a nitrogen compound as an accelerator.

2. The one-pack composition of claim 1 , wherein (B) the at least bifunctional thiol comprises an ester-free thiol.

3. The one-pack composition of claim 1 , wherein (B) the at least bifunctional thiol comprises a thiol-terminated isocyanurate.

4. The one-pack composition of claim 1 , wherein (B) the at least bifunctional thiol comprises or consists of tris(3-mercaptopropyl)isocyanurate.

5. The one-pack composition of claim 1 , wherein (C) the radiation-curable compound is present in a proportion of up to 50 wt %, based on a total weight of components (A) to (F).

6. The one-pack composition of claim 1 , wherein (C) the radiation-curable compound is present in a proportion of 10 to 50 wt %, based on a total weight of components (A) to (F).

7. The one-pack composition of claim 1 , wherein (C) the radiation-curable compound comprises an at least bifunctional (meth)acrylate and is present in a proportion of 15 to 50 wt %, based on a total weight of components (A) to (F).

8. The one-pack composition of claim 1 , wherein (E) the stabilizer blend contains 0.01 to 1 wt % of (E1) the at least one sulfonyl isocyanate and 0.01 to 1 wt % of (E2) the at least one acid, based on a total weight of components (A) to (F).

9. The one-pack composition of claim 1 , wherein (E) the stabilizer blend contains 0.01 to 0.5 wt % of (E1) the at least one sulfonyl isocyanate and 0.01 to 0.5 wt % of (E2) the at least one acid based on a total weight of components (A) to (F).

10. The one-pack composition of claim 1 , wherein (E1) the at least one sulfonyl isocyanate comprises or consists of p-toluene sulfonyl isocyanate.

11. The one-pack composition of claim 1 , wherein (E2) the at least one acid comprises or consists of an acidic phenol.

12. The one-pack composition of claim 1 , wherein (E2) the at least one acid comprises or consists of pyrogallol.

13. The one-pack composition of claim 1 , wherein (F) the nitrogen compound as an accelerator is a nitrogen compound that is solid at room temperature and is present in a dispersed form in the one-pack composition.

14. The one-pack composition of claim 1 , wherein (F) the nitrogen compound as an accelerator comprises a photolatent base.

15. The one-pack composition of claim 1 , wherein the composition, based on a total weight of components (A) to (F), comprises the following components:

5-80 wt % of (A) the at least bifunctional epoxy-containing compound;

15-80 wt % of (B) the at least bifunctional thiol;

up to 50 wt % of (C) the radiation-curable compound, which comprises an at least bifunctional (meth)acrylate;

0.1-5 wt % of (D) the photoinitiator;

(E) the stabilizer blend containing 0.01-0.5 wt % of (E1) the at least one sulfonyl isocyanate and 0.01-0.5 wt % of (E2) the at least one acid, which comprises at least one organic acid;

0.5-15 wt % of (F) the nitrogen compound as an accelerator, which is solid at room temperature and is present in a dispersed form in the one-pack composition; and

(G) 0 to 90 wt % of fillers and 0.1 to 15 wt % of a thixotropic agent.

16. The one-pack composition of claim 1 , wherein the composition has an increase in viscosity of less than 25% after storage for at least 24 h, at room temperature.

17. The one-pack composition of claim 1 , wherein the composition completely cures at a temperature of 40 to 100° C., within a period of up to 90 min.

18. The one-pack composition of claim 1 , wherein the composition has an increase in viscosity of less than 25% after storage for at least 72 h, at room temperature.

19. The one-pack composition of claim 1 , wherein the composition completely cures at a temperature from 60° C. to 90° C., within a period of up to 90 min.

20. The one-pack composition of claim 1 , which is adapted for use as an adhesive or sealant for bonding, casting, sealing and/or coating of substrates.

21. The one-pack composition of claim 20 , wherein the substrate is at least one of an optical, electronic, or optoelectronic part.

22. A method for bonding, casting, sealing and/or coating of substrates using the composition of claim 1 , the method comprising:

a) dosing the composition onto a first substrate;

b) irradiating the composition with actinic radiation;

c) optionally supplying a second substrate prior to or after step b) to form a substrate composite, wherein the second substrate is brought into contact with the composition; and

d) heat-curing the irradiated composition on at least one of the substrate or the substrate composite.

23. The method of claim 22 , wherein the composition, after irradiation with actinic radiation, has a shear strength of at least 0.9 MPa.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 15, 2020
From: ZILLESSEN, ANDREAS; ROEDIGER, SABRINA; SUEVEGES, BASTIAN; BORN, ROBERT
To: DELO INDUSTRIE KLEBSTOFFE GMBH & CO KGAA
Reel/Frame 052935/0529 →
Priority Claims (1)
DE 102017129780.4 · Dec 13, 2017 · national
Continuity (1)
Related Publication 20200385513A1 · Dec 10, 2020