IP Library Patent Application 18576224
Patent Application
App. No. 18/576,224

COMPOSITION BASED ON (METH)ACRYLATE MONOMERS

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Patent No.
US None
App. No.
18/576,224
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; 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 photoinitiator P1; a component B comprising at least one dihydropyridine compound having one of the formulae (III) to (VI); said composition not comprising any peroxide.

Claims (80)

1 - 17 . (canceled)

18 . 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;

at least one (meth)acrylate monomer M1;

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

at least one photoinitiator P1;

a component B comprising at least one dihydropyridine compound having one of the formulae (III) to (VII) 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 Ra 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.

19 . The composition as claimed in claim 18 , 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 − ; (F 5 Ph) 4 B − or SbF 6 − , X − .

20 . The composition as claimed in claim 18 , 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.

21 . The composition as claimed in claim 18 , characterized in that the (meth)acrylate monomer M1 has the formula (II) below:

in which R 3 represents H or methyl, G represents an organic radical, and f represents an integer from 1 to 4.

22 . The composition as claimed in claim 18 , characterized in that the (meth)acrylate monomer M1 is chosen from the group consisting of:

compounds having the formula (II-1) below:

in which:

R 3 represents H or methyl;

G is chosen from the group consisting of alkyls, cycloalkyls, alkenyls, cycloalkenyls, alkylaryls, arylalkyls or aryls, said alkyls, cycloalkyls, alkenyls, cycloalkenyls, alkylaryls, arylalkyls or aryls possibly being optionally substituted with and/or interrupted with at least one silane, silicone, oxygen, halogen, carbonyl, hydroxyl, ester, urea, urethane, carbonate, amine, amide, sulfur, sulfonate or sulfone;

polyethylene glycol di(meth)acrylates;

hexanediol di(meth)acrylate;

trimethylolpropane 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;

diglycerol 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 (VIII), (IX) or (X) below

in which:

R 3 represents H or methyl;

R 4 represents H, methyl or ethyl;

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;

and mixtures thereof.

23 . The composition as claimed in claim 18 , characterized in that G is an organic radical comprising at least one oxygen atom, said radical G being a polar aprotic radical.

24 . The composition as claimed in claim 18 , characterized in that the monomer M1 is chosen from the following compounds:

25 . The composition as claimed in claim 18 , characterized in that the content of (meth)acrylate monomer(s) M1 in the crosslinkable two-component composition ranges from 30% to 99% by weight relative to the total weight of said crosslinkable two-component composition.

26 . The composition as claimed in claim 18 , characterized in that the photoinitiator P1 is chosen from the group consisting of:

type I photoinitiators chosen from:

the family of acetophenones and alkoxyacetophenones;

the family of hydroxyacetophenones;

the family of alkylaminoacetophenones;

the family of benzoin ethers;

the family of phosphine oxides;

the family of metallocenes;

type II photoinitiators chosen from:

the family of benzophenones;

the family of thioxanthones;

the family of benzoylformate esters;

the family of dibenzylidene ketones;

the family of coumarins;

photoinitiators of the family of dyes;

and mixtures thereof.

27 . The composition as claimed in claim 18 , characterized in that the photoinitiator P1 is chosen from:

the family of phosphine oxides;

the family of thioxanthones.

28 . The composition as claimed in claim 18 , characterized in that the total content of photoinitiator(s) P1 may range from 0.1% to 5% by weight relative to the total weight of the crosslinkable two-component composition according to the invention.

29 . The composition as claimed in claim 18 , characterized in that the dihydropyridine compound has the formula (VI) or (VII) as defined in claim 18 .

30 . The composition as claimed in claim 18 , characterized in that the dihydropyridine compound is chosen from the following compounds:

31 . The composition as claimed in claim 18 , characterized in that the mole ratio of dihydropyridine compound(s) of formulae (III) to (VII)/iodonium salt(s) of formula (I-A) or (I-B) or (I-C) ranges from 0.70 to 9.

32 . The composition as claimed in claim 18 , characterized in that the acid having a pKa or pka1 ranging from 0.3 to 5 is an organic acid chosen from carboxylic acids.

33 . An adhesive, mastic or coating comprising the composition as defined in claim 18 .

34 . 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 18 ; and then

bringing the two substrates into effective contact; and

crosslinking of the composition by means of 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 THE MISSING ASSIGNEE INFORMATION BY ADDING THE FOLLOWING TWO ADDITIONAL ASSIGNEES: UNIVERSITE DE HAUTE-ALSACE AND CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE, PREVIOUSLY RECORDED AT REEL: 66512 FRAME: 683. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Feb 27, 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 066694/0863 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 21, 2024
From: MAZAJCZYK, JÉRÔME; FOUQUAY, STÉPHANE; SIMON, FRÉDÉRIC; MICHAUD, GUILLAUME; BARRAT, ALEXIS; LALEVEE, JACQUES
To: BOSTIK SA
Reel/Frame 066512/0683 →