IP Library Granted Patent US 12,410,346
Granted Patent B2
US 12,410,346 · App. 17/441,319 · Granted Sep 9, 2025

Process of manufacturing a curable precursor of a structural adhesive composition

Inventors: Elisabeth Cura (Düsseldorf, DE); Boris Tasch (Düsseldorf, DE); Adrian Jung (Kaarst, DE)
Assignee: 3M Innovative Properties Company
C09J163/00C08G59/686
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Quick Facts
Patent No.
US 12,410,346
App. No.
17/441,319
Granted
Sep 9, 2025
Kind
B2
Abstract

The present disclosure relates to a process of manufacturing curable precursor of a structural adhesive composition. According to another aspect, the present disclosure is directed to method of bonding two parts.

Claims (33)

1. A process of manufacturing a curable precursor of a structural adhesive composition, comprising the steps of:

providing an extruder comprising a reaction chamber and an extrusion die;

providing a curable precursor of a structural adhesive composition, comprising:

a cationically self-polymerizable monomer, wherein the cationically self-polymerizable monomer is a polyfunctional compound comprising at least one cyclic amine;

a polymerization initiator of the cationically self-polymerizable monomer which is initiated at a temperature T 1 ;

a curable monomer which is different from the cationically self-polymerizable monomer, wherein the curable monomer which is different from the cationically self-polymerizable monomer comprises at least one functional group selected from the group consisting of epoxy groups; and

a curing initiator of the curable monomer which is initiated at a temperature T 2 and which is different from the polymerization initiator of the cationically self-polymerizable monomer;

incorporating and mixing the curable precursor of the structural adhesive composition in the reaction chamber of the extruder, thereby forming an extrudable composition;

pressing the extrudable composition of the preceding step through the extrusion die, thereby forming an extrudate of the curable precursor of the hybrid structural adhesive composition;

optionally, cooling down the extrudate of preceding step; and

allowing the self-polymerization reaction of the cationically self-polymerizable monomers in the extrudate; and

wherein the polymerization initiator of the cationically self-polymerizable monomer or the cationically self-polymerizable monomer is incorporated and mixed in the curable precursor of the structural adhesive composition immediately prior to the step of pressing the extrudable composition through the extrusion die.

2. A process according to claim 1 , wherein the temperature T 2 is greater than T 1 , and wherein the temperature T 1 at which the polymerization initiator of the cationically self-polymerizable monomer is initiated is insufficient to cause initiation of the curing initiator of the curable monomer.

3. A process according to claim 1 , wherein the cationically self-polymerizable monomers remain substantially unpolymerized before the extrudable composition is pressed through the extrusion die.

4. A process according to claim 1 , wherein the cationically self-polymerizable monomer is an oligomer having a number average molecular weight no greater than 20,000 g/mol.

5. A process according to claim 1 , wherein the cationically self-polymerizable monomer is a polyfunctional compound comprising two cyclic amines.

6. A process according to claim 1 , wherein the cationically self-polymerizable monomer is an aziridino-functional polyether oligomer.

7. A process according to claim 1 , wherein the curable monomer which is different from the cationically self-polymerizable monomer comprises at least one functional group selected from the group consisting of glycidyl groups.

8. A process according to claim 1 , wherein the polymerization initiator of the cationically self-polymerizable monomer is selected from the group consisting of protonating agents, alkylating agents, and any mixtures thereof.

9. A process according to claim 1 , wherein the curing initiator of the curable monomer is selected from the group consisting of primary amines, secondary amines, and any mixtures thereof.

10. A process according to claim 1 , wherein the extrudate comprises:

a polymeric material comprising the self-polymerization reaction product of a polymerizable material comprising a cationically self-polymerizable monomer, wherein the cationically self-polymerizable monomer is a polyfunctional compound comprising at least one cyclic amine;

optionally, some residual polymerization initiator of the cationically self-polymerizable monomer which is initiated at a temperature T 1 ;

a curable monomer which is different from the cationically self-polymerizable monomer, wherein the curable monomer which is different from the cationically self-polymerizable monomer comprises at least one functional group selected from the group consisting of epoxy groups;

a curing initiator of the curable monomer which is initiated at a temperature T 2 and which is different from the polymerization initiator of the cationically self-polymerizable monomer; and

wherein the curable monomers are substantially uncured and are embedded into the polymeric material comprising the self-polymerization reaction product of a polymerizable material comprising a cationically self-polymerizable monomer.

11. A process according to claim 1 , which further comprises the step of shaping the extrudate in the form of a three-dimensional object.

12. A process according to claim 11 , wherein the three-dimensional object has a shape selected from the group consisting of circular, semi-circular, ellipsoidal, square, rectangular, triangular, trapezoidal, polygonal shape, or any combinations thereof.

13. A method of bonding two parts, which comprises the steps of:

applying an extrudate as described in claim 1 to a surface of at least one of the two parts;

joining the two parts so that the extrudate is positioned between the two parts; and

substantially fully curing the extrudate by initiating the curing initiator of the cationically curable monomer, thereby obtaining a structural adhesive composition having a degree of polymeriaztion of at least 95% and bonding the two parts.

14. A method of bonding two parts according to claim 13 , wherein the two parts are metal or composite material parts, and wherein the method is for hem flange bonding of metal or composite material parts.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 21, 2021
From: CURA, ELISABETH; TASCH, BORIS; JUNG, ADRIAN
To: 3M INNOVATIVE PROPERTIES COMPANY
Reel/Frame 057539/0971 →
Priority Claims (1)
EP 19166871 · Apr 2, 2019 · regional
Continuity (1)
Related Publication 20220177749A1 · Jun 9, 2022
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