IP Library Granted Patent US 11,879,078
Granted Patent B2
US 11,879,078 · App. 17/281,104 · Granted Jan 23, 2024

Curable precursor of a structural adhesive composition

Inventors: Adrian T. Jung (Kaarst, DE); Boris Tasch (Düsseldorf, DE); Dirk Hasenberg (Raeren, BE); Olaf Ludewig (Düsseldorf, DE); Elisabeth Cura (Düsseldorf, DE)
Assignee: 3M Innovative Properties Company
C09J5/06C08G59/50C08G65/20C08G65/33317C08K5/0025C09J9/00
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Quick Facts
Patent No.
US 11,879,078
App. No.
17/281,104
Granted
Jan 23, 2024
Kind
B2
Abstract

The present disclosure relates to a curable precursor of a structural adhesive composition, comprising: a) a cationically self-polymerizable monomer; b) a polymerization initiator of the cationically self-polymerizable monomer which is initiated at a temperature T1; c) a curable monomer which is different from the cationically self-polymerizable monomer; and d) a curing initiator of the curable monomer which is initiated at a temperature T2 and which is different from the polymerization initiator of the cationically self-polymerizable monomer. According to another aspect, the present disclosure is directed to a partially cured precursor of a structural adhesive composition. According to still another aspect, the present disclosure relates to a method of bonding to parts. In yet another aspect, the disclosure relates to the use of a curable precursor or a partially cured precursor as described above, for industrial applications, in particular for body-in-white bonding applications for the automotive industry.

Claims (32)

1. A curable precursor of a structural adhesive composition, comprising:

a cationically self-polymerizable monomer which comprises at least one cyclic amine;

a polymerization initiator of the cationically self-polymerizable monomer which is initiated at a temperature T1;

a curable monomer which is different from the cationically self-polymerizable monomer which comprises at least one epoxy group; and

a curing initiator of the curable monomer which is initiated at a temperature T2 and which is different from the polymerization initiator of the cationically self-polymerizable monomer.

2. A curable precursor according to claim 1 , wherein the temperature T2 is greater than T1, and wherein the temperature T1 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 curable precursor according to any of claim 1 , wherein the temperature T1 is no greater than 90° C.

4. A curable precursor according to claim 1 , wherein the temperature T2 is greater than 90° C.

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

6. A curable precursor according to claim 1 , wherein the cationically self-polymerizable monomer is a polyfunctional compound comprising at least one two cyclic amines.

7. A curable precursor according to claim 1 , wherein the cationically self-polymerizable monomer comprising at least one cyclic amine is an aziridino-functional polyether oligomer.

8. A curable precursor according to claim 1 , wherein the curable monomer which is different from the cationically self-polymerizable monomer comprises at least one glycidyl group.

9. A curable precursor 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 combinations or mixtures thereof.

10. A curable precursor 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 combinations or mixtures thereof.

11. A curable precursor according to claim 1 , which further comprises a curing accelerator of the curable monomer which is selected from the group consisting of polyamines, polyamine adducts, ureas, substituted urea adducts, imidazoles, imidazole salts, imidazolines, aromatic tertiary amines, and any combinations or mixtures thereof.

12. A curable precursor according to claim 1 , which further comprises a thermoplastic resin having in particular a glass transition temperature (Tg) in a range from 60° C. to 140° C., when measured by Differential Scanning Calorimetry (DSC).

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

applying the curable precursor according to claim 1 to a surface of at least one of the two parts;

joining the two parts so that the curable precursor or the partially cured precursor structural adhesive composition is positioned between the two parts; and

optionally, partially curing the curable precursor according of step a) by initiating the polymerization initiator of the cationically self-polymerizable monomer, thereby forming a partially cured precursor comprising a polymeric material resulting from the self-polymerization reaction product of the cationically self-polymerizable monomer; and/or

substantially fully curing the partially cured precursor of step a) or c) by initiating the curing initiator of the cationically curable monomer, thereby obtaining a substantially fully cured structural adhesive composition and bonding the two parts.

14. A partially cured precursor of a structural adhesive composition, comprising:

a polymeric material comprising the self-polymerization reaction product of a polymerizable material comprising a cationically self-polymerizable monomer which comprises at least one cyclic amine

optionally, some residual polymerization initiator of the cationically self-polymerizable monomer which is initiated at a temperature T1;

a curable monomer which is different from the cationically self-polymerizable monomer which comprises at least one epoxy group; and

a curing initiator of the curable monomer which is initiated at a temperature T2 and which is different from the polymerization initiator of the cationically self-polymerizable monomer; and

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

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

applying the partially cured precursor according to claim 14 to a surface of at least one of the two parts;

joining the two parts so that the curable precursor or the partially cured precursor structural adhesive composition is positioned between the two parts; and

optionally, partially curing the curable precursor according of step a) by initiating the polymerization initiator of the cationically self-polymerizable monomer, thereby forming a partially cured precursor comprising a polymeric material resulting from the self-polymerization reaction product of the cationically self-polymerizable monomer; and/or

substantially fully curing the partially cured precursor of step a) or c) by initiating the curing initiator of the cationically curable monomer, thereby obtaining a substantially fully cured structural adhesive composition and bonding the two parts.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 29, 2021
From: JUNG, ADRIAN T.; TASCH, BORIS; HASENBERG, DIRK; LUDEWIG, OLAF; CURA, ELISABETH
To: 3M INNOVATIVE PROPERTIES COMPANY
Reel/Frame 055754/0962 →
Priority Claims (1)
EP 18198473 · Oct 3, 2018 · regional
Continuity (1)
Related Publication 20210340406A1 · Nov 4, 2021
Cited By (1)
US 12,729,328