IP Library Patent Application 18576182
Patent Application
App. No. 18/576,182

COMPOSITION BASED ON (METH)ACRYLATE MONOMERS

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Quick Facts
Patent No.
US None
App. No.
18/576,182
Abstract

The present invention relates to a crosslinkable two-component composition comprising: a component A comprising: an iodonium salt having one of the formulae (I-A), (I-B) or (I-C); at least one (meth)acrylate monomer M1 having one of the formulae (II), (III) or (IV); an organic or mineral acid having a pKa or pKa1 ranging from 0.3 to 5 measured in water at 25° C.; a copper salt or a copper complex; a component B comprising at least one dihydropyridine compound having one of the formulae (VI) to (X); said composition not comprising any peroxide.

Claims (46)

1 - 16 . (canceled)

17 . A crosslinkable two-component composition comprising:

a component A comprising:

an iodonium salt having one of the formulae (I-A), (I-B) or (I-C) below:

in which:

R 1 and R 2 each represent, independently of each other, a hydrogen atom, an alkyl radical, an alkenyl radical, a cycloalkyl radical, a cycloalkenyl radical, an aryl radical, a chlorine atom, a bromine atom, an iodine atom, a carboxylic radical, or an —NO 2 radical;

X − represents a monovalent anion; and

W represents O or S;

an organic or mineral acid having a pKa or pKa1 ranging from 0.3 to 5 measured in water at 25° C.;

at least one (meth)acrylate monomer M1 having one of the formulae (II), (III) or (IV) below:

in which:

R 3 represents H or a methyl;

R 4 represents H, methyl or ethyl;

p represents 0 or 1; and

Z represents H, O, S, an alkyl group, a benzyl group, an aryl group or an alkoxy group;

Y represents O, S, NH or CH 2 ;

is a single bond or a double bond,

on condition that when Z represents O, then the bond is a double bond;

optionally a copper salt of formula (V-1) or a copper complex of formula (V-2):

in which:

R and R″ each represent, independently of each other, an alkyl radical, a cycloalkyl radical, an aryl radical or a heteroaryl radical,

R′ represents a hydrogen atom, an alkyl radical, a cycloalkyl radical, an aryl radical or a heteroaryl radical,

or R and R′ (or R′ and R″) may also be engaged in one and the same ring comprising from 5 to 8 carbon atoms, said ring optionally comprising at least one heteroatom;

a component B comprising at least one dihydropyridine compound having one of the formulae (VI) to (X) below:

in which:

each of the radicals R 5 to R 11 represents, independently of each other, a hydrogen, an alkyl, an alkenyl, an alkynyl, a cycloalkyl, a heterocycloalkyl, a heteroaryl, an aryl, an alkylaryl, an arylalkyl, a radical —COOR a ; said alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, heteroalkyl, aryl, alkylaryl and arylalkyl groups being optionally substituted; and R a represents an alkyl or aryl radical;

or two radicals from among R 5 to R 11 together form an optionally substituted monocyclic or polycyclic ring;

said crosslinkable two-component composition not comprising any peroxide.

18 . The composition as claimed in claim 17 , characterized in that, in formula (I-A) or (I-B) or (I-C), X − represents F − , Cl − , Br − , I − , NO 3 − , HSO 4 − , H 2 PO 4 − , HCOO − , CH 3 COO − , BF 4 − , AsF 6 − , PF 6 − , CH 3 —Ph—SO 3 − , SbF 6 − or (F 5 Ph) 4 B − .

19 . The composition as claimed in claim 17 , characterized in that the iodonium salt of formula (I-A) or (I-B) or (I-C) is chosen from diphenyliodonium hexafluorophosphate, diphenyliodonium fluoroborate, diphenyliodonium 2-carboxylate, bis(4-tert-butylphenyl)iodonium hexafluorophosphate, 3,3′-dimethyldiphenyliodonium hexafluorophosphate and (4-isopropylphenyl)(4-methylphenyl)iodonium tetrakis(pentafluorophenyl)borate.

20 . The composition as claimed in claim 17 , characterized in that the iodonium salt is (4-isopropylphenyl)(4-methylphenyl)iodonium tetrakis(pentafluorophenyl)borate.

21 . The composition as claimed in claim 17 , in which the total content of iodonium salt of formula (I-A) or (I-B) or (I-C) ranges from 0.05% to 5.0% by weight, relative to the total weight of said crosslinkable two-component composition.

22 . The composition as claimed in claim 17 , characterized in that the (meth)acrylate monomer M1 is chosen from the following monomers:

23 . The composition as claimed in claim 17 , characterized in that the total content of (meth)acrylate monomer(s) M1 ranges from 20% to 99% by weight, relative to the total weight of said crosslinkable two-component composition.

24 . The composition as claimed in claim 17 , characterized in that the copper salt of formula (V-1) is copper acetate, and the copper complex of formula (V-2) is copper acetylacetonate.

25 . The composition as claimed in claim 17 , characterized in that the dihydropyridine compound has the formula (IX) or (X) as defined in claim 17 .

26 . The composition as claimed in claim 17 , characterized in that the dihydropyridine compound is chosen from the following compounds:

27 . The composition as claimed in claim 17 , characterized in that the mole ratio of dihydropyridine compound(s) of formulae (VI) to (X)/iodonium salt(s) of formula (I-A) or (I-B) or (I-C) ranges from 0.25 to 9 in said composition.

28 . The composition as claimed in claim 17 , characterized in that the acid having a pKa or pka1 ranging from 0.3 to 5 is an organic acid chosen from carboxylic acids.

29 . The composition as claimed in claim 17 , characterized in that the acid has a pka or pka1 ranging from 2 to 5.

30 . The composition as claimed in claim 17 , characterized in that the composition does not comprise any hydroxyalkyl (meth)acrylate.

31 . An adhesive, mastic or coating comprising the composition as defined in claim 17 .

32 . A process 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 components A and B as defined in claim 17 ; and then

bringing the two substrates into effective contact; and

crosslinking the composition.

Assignments (2)
CHANGE OF ADDRESS Recorded Jul 30, 2025
From: BOSTIK SA
To: BOSTIK SA
Reel/Frame 072277/0238 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 25, 2024
From: MAZAJCZYK, JÉRÔME; FOUQUAY, STÉPHANE; SIMON, FRÉDÉRIC; MICHAUD, GUILLAUME; BARRAT, ALEXIS; LALEVEE, JACQUES
To: BOSTIK SA; UNIVERSITE DE HAUTE-ALSACE; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE
Reel/Frame 066243/0211 →