IP Library Granted Patent US 12,152,175
Granted Patent B2
US 12,152,175 · App. 17/779,406 · Granted Nov 26, 2024

Composition made from (meth)acrylate monomers

Inventors: Guillaume Michaud (Lyons, FR); Frédéric Simon (Venette, FR); Stéphane Fouquay (Venette, FR); Jacques Lalevee (Mulhouse, FR)
Assignees: BOSTIK SA; UNIVERSITE DE HAUTEALSACE; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE
C09J4/06C09J4/00C09J5/00C09J11/06C09J11/08C09J133/14C09J2433/00C09J2491/00
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Quick Facts
Patent No.
US 12,152,175
App. No.
17/779,406
Granted
Nov 26, 2024
Kind
B2
Abstract

The present invention relates to a two-component composition comprising: —a composition A comprising: —at least one reducing agent; —at least one (meth)acrylate monomer; —a composition B comprising: —at least one oxidising agent; and—optionally at least one (meth)acrylate monomer; the composition being characterised in that: —it comprises at least one radical photoinitiator in composition A and/or B; —it comprises at least one polymerisation inhibitor in an amount less than or equal to 0.3% by weight relative to the total weight of the composition.

Claims (80)

1. Two-component composition comprising:

a composition A comprising:

at least one reducing agent; and

at least one (meth)acrylate monomer;

a composition B comprising:

at least one oxidizing agent; and

optionally at least one (meth)acrylate monomer;

said composition being characterized in that:

it comprises at least one radical photoinitiator in composition A and/or B; and

it comprises at least one polymerization inhibitor in a content of less than or equal to 0.3% by weight relative to the total weight of said composition,

the radical photoinitiator being selected from the group consisting of:

radical photoinitiators of type I selected from the group consisting of:

the family of the acetophenones and alkoxyacetophenones;

the family of the hydroxyacetophenones;

the family of the alkylaminoacetophenones;

the family of the benzoin ethers;

the family of the phosphine oxides; and

the family of the metallocenes;

radical photoinitiators of type II selected from the group consisting of:

the family of the benzophenones;

the family of the thioxanthones;

the family of the benzoylformate esters;

the family of the dibenzylidene ketones; and

the family of the coumarins;

radical photoinitiators of the family of the dyes;

and of mixtures thereof,

wherein the at least one reducing agent is a tertiary amine of formula (I):

in which:

m and n are, independently of one another, an integer ranging from 1 to 150;

R 1 represents a radical selected from the group consisting of a linear or branched, saturated or unsaturated alkyl comprising from 1 to 20 carbon atoms; a (hetero)aryl comprising from 6 to 12 carbon atoms; a cycloalkyl comprising from 3 to 12 carbon atoms;

v represents an integer ranging from 0 to 5;

R 2 and R 3 represent, independently of one another, a halogen atom, a hydrogen atom or a linear or branched alkyl group comprising from 1 to 12 carbon atoms, said alkyl group being optionally interrupted by at least one oxygen atom;

on the condition that m+n>2.

2. Composition according to claim 1 , wherein the total content of polymerization inhibitor(s) is less than or equal to 0.25% by weight relative to the total weight of said composition.

3. Composition according to claim 1 , wherein the total content of polymerization inhibitor(s) ranges from 0.01% to 0.20% by weight relative to the total weight of said composition.

4. Composition according to claim 1 , wherein the reducing agent is selected from the group consisting of tertiary amines, sodium metabisulfite, sodium bisulfite, transition metals, azo compounds, alpha-aminosulfones, and mixtures thereof.

5. Composition according to claim 1 , wherein the oxidizing agent is selected from the group consisting of peroxides, organic salts of transition metals, compounds containing a labile chlorine, and mixtures thereof.

6. Composition according to claim 1 , wherein the radical photoinitiator is selected from the group consisting of:

the family of the phosphine oxides;

the family of the thioxanthones.

7. Composition according to claim 1 , wherein composition B does not comprise any epoxy resin.

8. Composition according to claim 1 , wherein it comprises from 0.1% to 5% by weight, of radical photoinitiator(s), relative to the total weight of the composition.

9. Composition according to claim 1 , wherein the (meth)acrylate monomer is selected from the group consisting of:

compounds having formula (III) below:

H 2 C═C(R 5 )—COOR 6   (III)

in which:

R 5 represents a hydrogen atom or a methyl group;

R 6 is selected from the group consisting of alkyls, cycloalkyls, alkenyls, cycloalkenyls, alkylaryls, arylalkyls or aryls, it being possible for said alkyls, cycloalkyls, alkenyls, cycloalkenyls, alkylaryls, arylalkyls or aryls to be optionally substituted and/or interrupted by at least one silane, one silicone, one oxygen, one halogen, one carbonyl, one hydroxyl, one ester, one urea, one urethane, one carbonate, one amine, one amide, one sulfur, one sulfonate, or one sulfone;

polyethylene glycol di(meth)acrylates;

tetrahydrofuran (meth)acrylates;

hydroxypropyl (meth)acrylate;

hexanediol di(meth)acrylate;

trimethylol propane tri(meth)acrylate;

diethylene glycol di(meth)acrylate;

triethylene glycol di(meth)acrylate;

tetraethylene glycol di(meth)acrylate;

dipropylene glycol di(meth)acrylate;

di(pentamethylene glycol) di(meth)acrylate;

diglyceryl tetra(meth)acrylate;

tetramethylene di(meth)acrylate;

ethylene di(meth)acrylate;

bisphenol A mono- and di(meth)acrylates;

bisphenol F mono- and di(meth)acrylates;

compounds of formula (IV) or (V) below:

in which:

R7 represents H or a methyl;

R8 represents H or ethyl;

p represents 0 or 1; and

Z represents H, ═O, a linear or branched alkyl group, a benzyl group, an aryl group or an alkoxy group;

mixtures thereof.

10. Composition according to claim 1 , wherein the (meth)acrylate monomer is selected from the group consisting of the following monomers and mixtures thereof:

11. Composition according to claim 1 , wherein composition A comprises a total content of (meth)acrylate monomer(s) of greater than or equal to 30%, by weight relative to the total weight of composition A.

12. Composition according to claim 1 , wherein composition B comprises a total content of (meth)acrylate monomer(s) of greater than or equal to 40% by weight relative to the total weight of composition B.

13. Composition according to claim 1 , wherein the composition comprises at least one additive selected from the group consisting of catalysts, fillers, antioxidants, light stabilizers/UV absorbers, metal deactivators, antistatics, film-preventing agents, foaming agents, biocides, plasticizers, lubricants, emulsifiers, dyes, pigments, rheological agents, impact modifiers, adhesion promoters, optical brighteners, flame retardants, anti-sweating agents, nucleating agents, solvents, and mixtures thereof.

14. Composition according to claim 1 , wherein the composition A/composition B ratio by volume ranges from 20/1 to 1/1.

15. An adhesive, sealant, or coating comprising the composition according to claim 1 .

16. Method for assembling two substrates by adhesive bonding, comprising:

the coating, onto at least one of the two substrates to be assembled, of a composition obtained by mixing compositions A and B as defined according to claim 1 ; then

actually bringing the two substrates into contact; and

crosslinking the composition by submission to electromagnetic irradiation.

Assignments (3)
CHANGE OF ADDRESS Recorded Jul 30, 2025
From: BOSTIK SA
To: BOSTIK SA
Reel/Frame 072277/0238 →
CORRECTIVE ASSIGNMENT TO CORRECT THE 2ND AND 3RD INVENTOR'S EXCLUSION OF ACCENT MARKS PREVIOUSLY RECORDED AT REEL: 060002 FRAME: 0232. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT . Recorded Jun 13, 2022
From: MICHAUD, GUILLAUME; SIMON, FRÉDÉRIC; FOUQUAY, STÉPHANE; LALEVEE, JACQUES
To: BOSTIK SA; UNIVERSITE DE HAUTE-ALSACE; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE
Reel/Frame 060352/0766 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 24, 2022
From: MICHAUD, GUILLAUME; SIMON, FREDERIC; FOUQUAY, STEPHANE; LALEVEE, JACQUES
To: BOSTIK SA; UNIVERSITE DE HAUTE-ALSACE; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE
Reel/Frame 060002/0232 →
Priority Claims (1)
FR FR1913176 · Nov 25, 2019 · national
Continuity (1)
Related Publication 20230022325A1 · Jan 26, 2023
Cited By (1)
US 12,421,430