IP Library › Granted Patent US 12,516,147

Granted Patent B2

US 12,516,147 · App. 17/785,095 · Granted Jan 6, 2026

Aldimines and uses thereof

Inventors: Stéphane Fouquay (Venette, FR); Federico Sanz (Venette, FR)

Assignee: BOSTIK SA

C08G18/4812 C08G18/12 C08G18/246 C08G18/307 C08G18/4825 C08G18/4829 C08G18/724 C08G18/755 C08G18/7621 C08G18/7642 C09D175/08 C09J175/08

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Quick Facts

Patent No.: US 12,516,147
App. No.: 17/785,095
Granted: Jan 6, 2026
Kind: B2

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Abstract

The present invention relates to compounds having one of the following formulae (I) and (II): and also to the uses thereof.

Claims (198)

1 . A compound having one of the following formulae (I) and (II):

in which:

X 1 represents F 1 or —N═C(H)-G 1 or -Ph-XH, or —XH, with X representing O or S or Se and Ph representing a phenyl group;

X 2 represents F 2 or —N═C(H)-G 1 or -Ph-XH, or —XH, with X representing O or S or Se and Ph representing a phenyl group;

X 3 represents F 3 or —N═C(H)-G 1 or -Ph-XH, or —XH, with X representing O or S or Se and Ph representing a phenyl group;

provided that at most just one radical from among the radicals X 1 , X 2 and X 3 represents —N═C(H)-G 1 ;

provided that at most just one radical from among the radicals X 1 , X 2 and X 3 represents —XH or -Ph-XH;

provided that when X 1 =—N═C(H)-G 1 , then q=1;

provided that when X 1 =—N═C(H)-G 1 or -Ph-XH or —XH, then X 2 =F 2 and X 3 =F 3 ;

provided that when X 2 =—N═C(H)-G 1 or -Ph-XH or —XH, then X 1 =F 1 and X 3 =F 3 ;

provided that when X 3 =—N═C(H)-G 1 or -Ph-XH or —XH, then X 2 =F 2 and X 1 =F 1 ;

F 1 represents a radical selected from the group consisting of a hydrogen atom, a linear or branched alkyl group comprising from 1 to 20 carbon atoms, an arylalkyl group comprising from 7 to 20 carbon atoms, a (hetero)aryl group comprising from 4 to 12 carbon atoms, and a (hetero)cycloalkyl group comprising from 3 to 20 carbon atoms, a —COOZ group, a —C(O)NH 2 group, an —SMe group, or a guanidyl group of formula —NH—C(═NH)—NH 2 ,

F 2 represents a radical selected from the group consisting of a hydrogen atom, a linear or branched alkyl group comprising from 1 to 20 carbon atoms, an arylalkyl group comprising from 7 to 20 carbon atoms, a (hetero)aryl group comprising from 4 to 12 carbon atoms, and a (hetero)cycloalkyl group comprising from 3 to 20 carbon atoms, a —COOZ group, a —C(O)NH 2 group, an —SMe group, or a guanidyl group of formula —NH—C(═NH)—NH 2 ,

F 3 represents a radical selected from the group consisting of a hydrogen atom, a linear or branched alkyl group comprising from 1 to 20 carbon atoms, an arylalkyl group comprising from 7 to 20 carbon atoms, a (hetero)aryl group comprising from 4 to 12 carbon atoms, and a (hetero)cycloalkyl group comprising from 3 to 20 carbon atoms, a —COOZ group, a —C(O)NH 2 group, an —SMe group, or a guanidyl group of formula —NH—C(═NH)—NH 2 ,

R 1 , R 2 , R 3 and R 4 each represent, independently of one another, a radical selected from the group consisting of a hydrogen atom, a linear or branched alkyl group comprising from 1 to 20 carbon atoms, said alkyl group optionally comprising one or more heteroatoms, a (hetero)cycloalkyl group comprising from 3 to 20 carbon atoms, an arylalkyl group comprising from 7 to 20 carbon atoms and a (hetero)aryl group comprising from 4 to 12 carbon atoms;

n is an integer ranging from 0 to 28;

p is an integer ranging from 0 to 10;

m represents 0 or 1;

q represents 0 or 1;

e is an integer ranging from 1 to 3;

f is an integer or non-integer ranging from 1 to 3;

f is an integer or non-integer ranging from 0 to 2;

the sum f+f represents an integer ranging from 1 to 3;

Z represents a monovalent organic radical Z′, divalent organic radical Z d or trivalent organic radical Z t , having a molar mass or a number-average molecular mass (Mn) ranging from 16 to 22 000 g/mol,

R ac represents a hydrogen atom or a monovalent hydrocarbon radical comprising from 1 to 60 carbon atoms, wherein said radical optionally comprises one or more heteroatoms;

G 1 represents a monovalent hydrocarbon radical of molar mass or of number-average molecular mass (Mn) ranging from 15 to 4000 g/mol, wherein said radical optionally comprises one or more heteroatoms, provided that G 1 does not represent a substituted or unsubstituted aryl radical;

in which:

X 1 represents F 1 or -Ph-XH, or —XH;

X 2 represents F 2 or -Ph-XH, or —XH;

X 3 represents F 3 or -Ph-XH, or —XH;

F 1 represents a radical selected from the group consisting of a hydrogen atom, a linear or branched alkyl group comprising from 1 to 20 carbon atoms, an arylalkyl group comprising from 7 to 20 carbon atoms, a (hetero)aryl group comprising from 4 to 12 carbon atoms, and a (hetero)cycloalkyl group comprising from 3 to 20 carbon atoms, a —COOZ′ group, a —C(O)NH 2 group, an —SMe group, or a guanidyl group of formula —NH—C(═NH)—NH 2 ,

F 2 represents a radical selected from the group consisting of a hydrogen atom, a linear or branched alkyl group comprising from 1 to 20 carbon atoms, an arylalkyl group comprising from 7 to 20 carbon atoms, a (hetero)aryl group comprising from 4 to 12 carbon atoms, and a (hetero)cycloalkyl group comprising from 3 to 20 carbon atoms, a —COOZ′ group, a —C(O)NH 2 group, an —SMe group, or a guanidyl group of formula —NH—C(═NH)—NH 2 ,

F 3 represents a radical selected from the group consisting of a hydrogen atom, a linear or branched alkyl group comprising from 1 to 20 carbon atoms, an arylalkyl group comprising from 7 to 20 carbon atoms, a (hetero)aryl group comprising from 4 to 12 carbon atoms, and a (hetero)cycloalkyl group comprising from 3 to 20 carbon atoms, a —COOZ′ group, a —C(O)NH 2 group, an —SMe group, or a guanidyl group of formula —NH—C(═NH)—NH 2 ,

X, R 1 , R 2 , R 3 , R 4 , n, q, m, p, e and Z′ being as defined for formula (I) above;

G 3 represents a monovalent hydrocarbon radical of molar mass or of number-average molecular mass (Mn) ranging from 14 to 4000 g/mol, it being possible fer wherein said radical optionally comprises one or more heteroatoms, provided that G 3 does not represent a substituted or unsubstituted arylene radical;

provided that at most just one radical from among the radicals X 1 , X 2 and X 3 represents —XH or -Ph-XH;

provided that when X 1 =-Ph-XH or —XH, then X 2 =F 2 and X 3 =F 3 ;

provided that when X 2 =-Ph-XH or —XH, then X 1 =F 1 and X 3 =F 3 ;

provided that when X 3 =-Ph-XH or —XH, then X 2 =F 2 and X 1 =F 1 .

2 . The compound as claimed in claim 1 , wherein Z m represents a radical selected from the group consisting of —OR 5 , —NH 2 , —NH—R′ and —N(R′)(R″), in which:

R 5 represents a linear or branched alkyl group comprising from 1 to 60 carbon atoms which may optionally comprise one or more heteroatoms, a (hetero)cycloalkyl group comprising from 3 to 20 carbon atoms, an arylalkyl group comprising from 7 to 20 carbon atoms, or a (hetero)aryl group comprising from 4 to 12 carbon atoms;

R′ represents a linear or branched alkyl group comprising from 1 to 60 carbon atoms which may optionally comprise one or more heteroatoms, an arylalkyl group comprising from 7 to 20 carbon atoms, a (hetero)aryl group comprising from 4 to 12 carbon atoms, or a (hetero)cycloalkyl group comprising from 3 to 20 carbon atoms;

R″ represents a linear or branched alkyl group comprising from 1 to 60 carbon atoms which may optionally comprise one or more heteroatoms, an arylalkyl group comprising from 7 to 20 carbon atoms, a (hetero)aryl group comprising from 4 to 12 carbon atoms, or a (hetero)cycloalkyl group comprising from 3 to 20 carbon atoms.

3 . The compound as claimed in claim 1 , wherein the radical -G 1 represents a radical —C(R 6 )(R 7 )(R′) or a radical -G 2 with:

R 6 and R 7 each representing, independently of one another, a monovalent hydrocarbon radical comprising from 1 to 12 carbon atoms, said radical being optionally substituted by an —OH group; or

R 6 and R 7 together form an aliphatic ring comprising from 4 to 12 carbon atoms, said ring being optionally substituted;

R 8 represents a monovalent hydrocarbon radical comprising from 1 to 60 carbon atoms, said radical optionally comprising a heteroatom;

G 2 represents an optionally substituted heteroaryl radical, or a radical —C(O)—R 12 with R 12 representing an alkoxy radical, an alkenyl radical, or an arylalkenyl radical comprising at least 6 carbon atoms,

said radical G 2 having a molar mass or a number-average molecular mass (Mn) ranging from 15 to 4000 g/mol.

4 . The compound as claimed in claim 1 , wherein, in formula (II), the radical -G 3 represents:

a linear or branched, cyclic or non-cyclic, saturated or unsaturated alkylene radical, or

a radical -G 5 -(G 6 -G 5 )-, of molar mass or of number-average molecular mass (Mn) ranging from 14 to 4000 g/mol, in which:

G 5 represents an optionally substituted hetero(arylene) radical;

G 6 represents an oxygen atom, a sulfur atom or a radical selected from the group consisting of one of the following radicals: —O—R 27 —O—, —CH 2 —O—R 28 —O—CH 2 —, —CH 2 —O—C(═O)—R 29 —C(═O)—O—CH 2 —, —CH 2 —O—C(═O)—NH—R 30 —NH—C(═O)—O—CH 2 —, —O—C(═O)—NH—R 31 —NH—C(═O)—O—, and —O—C(═O)—R 32 —C(═O)—O—, with R 27 , R 28 , R 29 , R 30 , R 31 and R 32 each representing, independently of one another, a hydrocarbon radical optionally comprising at least one heteroatom;

r represents 0 or 1;

provided that when r=0, then G 5 represents an optionally substituted heteroarylene;

a radical —CH(R 25 )(R 26 )-[G 4 -CH(R 25 )(R 26 )]W—, of molar mass or of number-average molecular mass (Mn) ranging from 42 to 4000 g/mol, in which:

R 25 and R 26 each represent, independently of one another, a monovalent hydrocarbon radical comprising from 1 to 12 carbon atoms, said radical being optionally substituted by an —OH group;

or R 25 and R 26 together form an aliphatic ring comprising from 4 to 12 carbon atoms, said ring being optionally substituted;

G 4 represents a carbon-carbon bond or a divalent hydrocarbon radical, said radical optionally comprising at least one heteroatom; and

w represents an integer equal to 0 or 1.

5 . The compound as claimed in claim 1 , wherein, in formulae (I) and (II):

n represents 0, 1, 2, 3, 4, 9 or 28;

m represents 0 or 1;

p represents 0 or 1 or 9 or 10;

q represents 0 or 1;

F 1 represents a radical selected from the group consisting of a hydrogen atom, a (hetero)aryl group comprising from 4 to 12 carbon atoms, a —COOZ group (formula (I) with Z being as defined above in formula (I), or, respectively, a —COOZ group with Z′ being as defined in formula (II)), a —C(O)NH 2 group, an —SMe group, and a guanidyl group of formula —NH—C(═NH)—NH 2 ,

F 2 represents a radical selected from the group consisting of a hydrogen atom and a linear or branched alkyl group comprising from 1 to 10 carbon atoms,

F 3 represents a radical selected from the group consisting of a hydrogen atom and a linear or branched alkyl group comprising from 1 to 10 carbon atoms;

R 1 , R 2 , R 3 and R 4 each represent, independently of one another, a hydrogen atom, or a linear or branched alkyl group comprising from 1 to 10 carbon atoms, or an arylalkyl group comprising from 7 to 20 carbon atoms, or an aryl group comprising from 6 to 12 carbon atoms.

6 . The compound as claimed in claim 1 , wherein, in formulae (I) and (II):

n represents 0, 1, 2, 3 or 4;

m represents 0 or 1;

p represents 0 or 1;

q represents 0 or 1;

F 1 represents a radical selected from the group consisting of a hydrogen atom, a heteroaryl group comprising from 4 to 12 carbon atoms, a —COOZ group (Z being as defined above in formula (I)), a —C(O)NH 2 group, an —SMe group, and a guanidyl group of formula —NH—C(═NH)—NH 2 ,

F 2 represents a radical selected from the group consisting of a hydrogen atom and a linear or branched alkyl group comprising from 1 to 5 carbon atoms,

F 3 represents a radical selected from the group consisting of a hydrogen atom;

R 1 , R 2 , R 3 and R 4 each represent, independently of one another, a hydrogen atom, or a linear or branched alkyl group comprising from 1 to 5 carbon atoms, or a benzyl group, or a phenyl group.

7 . The compound as claimed in claim 1 , wherein it is selected from the group consisting of the compounds of the following formulae (I-A), (I-B), (I-C) and (I-D):

in which:

R 1 , R 2 , R 3 , R 4 , n, m, p, q, e, f, f, Z, G 1 and R ac are as defined in formula (I) in claim 1 ,

X 1 represents F 1 as defined in formula (I) in claim 1 , or -Ph-XH, or —XH with X representing O or S or Se and Ph representing a phenyl group;

X 2 represents F 2 as defined in formula (I) in claim 1 , or -Ph-XH, or —XH with X representing O or S or Se and Ph representing a phenyl group;

X 3 represents F 3 as defined in formula (I) in claim 1 , or -Ph-XH, or —XH with X representing O or S or Se and Ph representing a phenyl group;

provided that at most one of the radicals X 1 , X 2 or X 3 represents a radical -Ph-XH or —XH with X representing O or S or Se and Ph representing a phenyl radical;

in which F 2 , F 3 , R 1 , R 2 , R 3 , R 4 , n, m, p, e, f, f, Z, G 1 and R ac are as defined in formula (I) in claim 1 ;

in which F 1 , F 3 , R 1 , R 2 R 3 , R 4 , F 2 , m, p, q, e, f, f, G 1 , Z and R a are as defined in formula (I) in claim 1 ;

in which F 1 , F 2 , R 1 , R 2 , R 3 , R 4 , F 2 , m p, q, e f, f, G 1 , Z and R ac are as defined in formula (I) in claim 1 .

8 . The compound as claimed in claim 7 , wherein the compounds of formula (I-A) have one of the following formulae (I-A-1), (I-A-2) or (I-A-3):

in which X, R 1 , R 2 , R 3 , R 4 , n, m, p, e, f, f, Z, F 2 , F 3 , G 1 and R ac are as defined in formula (I-A) in claim 7 ,

in which R 1 , R 2 , R 3 , R 4 m, p, e, f, f, Z, X, G 1 , F 1 , F 3 , G 1 and R a are as defined in formula (I-A) in claim 7 ,

in which R 1 , R 2 , R 3 , R 4 , n, p, q, e, f f, Z, X, G 1 , F 1 , F 2 , R are as defined in formula (I-A) in claim 7 .

9 . The compound as claimed in claim 7 , wherein the compounds of formula (I-B) have one of the following formulae (I-B-1), (I-B-2) or (I-B-3):

in which F 2 , F 3 , R 1 , R 2 , R 3 , R 4 , n, m, p, e, f, G 1 and Z are as defined in formula (I-B) in claim 7 ,

in which F 2 , F 3 , R 2 , R 3 , R 4 , n, m, p, e, f, G 1 , Z and R ac are as defined in formula (I-B) in claim 7 ,

in which F 2 , F 3 , R 1 , R 2 , R 3 , R 4 , n, m, p, e, f, G 1 , Z and R ac are as defined in formula (I-B) in claim 7 .

10 . The compound as claimed in claim 7 , wherein the compounds of formula (I-C) have one of the following formulae (I-C-1), (I-C-2) or (I-C-3):

in which F 1 , F 3 , R 1 , R 2 , R 3 , R 4 , F 2 , m, p, q, e, f, G 1 and Z are as defined in formula (I-C) in claim 7 ,

in which F 1 , F 3 , R 1 , R 2 , R 3 R 4 , F 2 , m, p, q, e, f, G 1 , Z and R ac are as defined in formula (I-C) in claim 7 ,

in which F 1 , F 3 , R 1 , R 2 , R 3 , R 4 , F 2 , m, p, q, e, f, G 1 , Z and R a are as defined in formula (I-C) in claim 7 .

11 . The compound as claimed in claim 7 , wherein the compounds of formula (I-D) have one of the following formulae (I-D-1), (I-D-2) or (I-D-3):

in which F 1 , F 2 , R 1 , R 2 , R 3 , R 4 , F 2 , n, m, p, q, e, f, G 1 and Z are as defined in formula (I-D) in claim 7 ,

in which F 1 , F 2 , R 1 , R 2 , R 3 , R 4 , F 2 , n, m, p, q, e, f, G 1 , Z and R a are as defined in formula (I-D) in claim 7 ,

in which F 1 , F 2 , R 1 , R 2 , R 3 , R 4 , F 2 , n, m, p, q, e, f, G 1 , Z and R ac are as defined in formula (I-D) in claim 7 .

12 . The compound of formula (I) as claimed claim 1 , wherein it is obtained by reaction between:

a compound of formula (III) below:

in which:

Y 1 represents F 1 or —NH 2 or -Ph-XH or —XH with X representing O or S or Se and Ph representing a phenyl group;

Y 2 represents F 2 or —NH 2 or -Ph-XH or —XH with X representing 0 or S or Se and Ph representing a phenyl group;

Y 3 represents F 3 or —NH 2 or -Ph-XH or —XH with X representing 0 or S or Se and Ph representing a phenyl group;

provided that at most just one radical from among the radicals Y 1 , Y 2 and Y 3 represents —NH 2 ,

provided that at most just one radical from among the radicals Y 1 , Y 2 and Y 3 represents -Ph-XH or —XH;

provided that when Y 1 =—NH 2 , then q=1;

provided that when Y 1 =—NH 2 or —XH or -Ph-XH, then Y 2 =F 2 and Y 3 =F 3 ;

provided that when Y 2 =—NH 2 or —XH or -Ph-XH, then Y 1 =F 1 and Y 3 =F 3 ;

provided that when Y 3 =—NH 2 or —XH or -Ph-XH, then Y 2 =F 2 and Y 1 =F 1 ;

n is an integer ranging from 0 to 28;

p is an integer ranging from 0 to 10;

m represents 0 or 1;

q represents 0 or 1;

e is an integer ranging from 1 to 3;

f is an integer or non-integer ranging from 1 to 3;

f is an integer or non-integer ranging from 0 to 2;

the sum f+f represents an integer ranging from 1 to 3;

Z represents a monovalent organic radical Z′, divalent organic radical Z d or trivalent organic radical Z t , having a number-average molecular mass (Mn) ranging from 16 to 000 g/mol,

R ac represents a hydrogen atom or a monovalent hydrocarbon radical comprising from to 60 carbon atoms, wherein said radical optionally comprises one or more heteroatoms;

and a compound of formula (IV) below:

in which G 1 is as defined in formula (I) in claim 1 .

13 . The compounds of formula (II) as claimed in claim 1 , wherein they are obtained by reaction between:

a compound of formula (III′) below:

in which:

Y 1 represents F 1 or -Ph-XH or —XH with X representing 0 or S or Se and Ph representing a phenyl group;

Y 2 represents F 2 or -Ph-XH or —XH with X representing 0 or S or Se and Ph representing a phenyl group;

Y 3 represents F 3 or -Ph-XH or —XH with X representing 0 or S or Se and Ph representing a phenyl group;

provided that at most just one radical from among the radicals Y 1 , Y 2 and Y 3 represents -Ph-XH or —XH;

provided that when Y 1 =—XH or -Ph-XH, then Y 2 =F 2 and Y 3 =F 3 ;

provided that when Y 2 =—XH or -Ph-XH, then Y 1 =F 1 and Y 3 =F 3 ;

provided that when Y 3 =—XH or -Ph-XH, then Y 1 =F 1 and Y 2 =F 2 ;

F 1 represents a radical chosen from a hydrogen atom, a linear or branched alkyl group comprising from 1 to 20 carbon atoms, an arylalkyl group comprising from 7 to 20 carbon atoms, a (hetero)aryl group comprising from to 12 carbon atoms, and a (hetero)cycloalkyl group comprising from 3 to 20 carbon atoms, a —COOZ′ group, a —C(O)NH 2 group, an —SMe group, or a guanidyl group of formula —NH—C(═NH)—NH 2 ,

F 2 represents a radical chosen from a hydrogen atom, a linear or branched alkyl group comprising from 1 to 20 carbon atoms, an arylalkyl group comprising from 7 to 20 carbon atoms, a (hetero)aryl group comprising from to 12 carbon atoms, and a (hetero)cycloalkyl group comprising from 3 to 20 carbon atoms, a —COOZ′ group, a —C(O)NH 2 group, an —SMe group, or a guanidyl group of formula —NH—C(═NH)—NH 2 ,

F 3 represents a radical chosen from a hydrogen atom, a linear or branched alkyl group comprising from 1 to 20 carbon atoms, an arylalkyl group comprising from 7 to 20 carbon atoms, a (hetero)aryl group comprising from to 12 carbon atoms, and a (hetero)cycloalkyl group comprising from 3 to 20 carbon atoms, a —COOZ′ group, a —C(O)NH 2 group, an —SMe group, or a guanidyl group of formula —NH—C(═NH)—NH 2 ,

R 1 , R 2 , R 3 and R 4 each represent, independently of one another, a radical chosen from a hydrogen atom, a linear or branched alkyl group comprising from 1 to 20 carbon atoms, said alkyl group optionally comprising one or more heteroatoms, a (hetero)cycloalkyl group comprising from 3 to 20 carbon atoms, an arylalkyl group comprising from 7 to 20 carbon atoms and a (hetero)aryl group comprising from 5 to 12 carbon atoms;

n is an integer ranging from 0 to 28;

p is an integer ranging from 0 to 10;

m represents 0 or 1;

q represents 0 or 1;

e is an integer ranging from 1 to 3;

Z m represents a monovalent organic radical having a number-average molecular mass (Mn) ranging from 16 to 22 000 g/mol;

and a compound of formula (VIII) below:

in which G 3 is as defined in formula (II) above in claim 1 .

14 . A compound having a formula (X) or (XI), wherein the compound is used as a moisture absorber (water scavenger) in a polyurethane-based composition or as curing agent in an epoxy resin-based composition:

in which:

X 1 represents F 1 or —N═C(H)-G 1 or -Ph-XH, or —XH, with X representing 0 or S or Se and Ph representing a phenyl group;

X 2 represents F 2 or —N═C(H)-G 1 or -Ph-XH, or —XH, with X representing 0 or S or Se and Ph representing a phenyl group;

X 3 represents F 3 or —N═C(H)-G 1 or -Ph-XH, or —XH, with X representing 0 or S or Se and Ph representing a phenyl group;

provided that at most just one radical from among the radicals X 1 , X 2 and X 3 represents —N═C(H)-G 1 ;

provided that at most just one radical from among the radicals X 1 , X 2 and X 3 represents —XH or -Ph-XH;

provided that when X 1 =—N═C(H)-G 1 , then q=1;

provided that when X 1 =—N═C(H)-G 1 or -Ph-XH or —XH, then X 2 =F 2 and X 3 =F 3 ;

provided that when X 2 =—N═C(H)-G 1 or -Ph-XH or —XH, then X 1 =F 1 and X 3 =F 3 ;

provided that when X 3 =—N═C(H)-G 1 or -Ph-XH or —XH, then X 2 =F 2 and X 1 =F 1 ;

R 1 , R 2 , R 3 and R 4 each represent, independently of one another, a radical selected from the group consisting of a hydrogen atom, a linear or branched alkyl group comprising from 1 to 20 carbon atoms, said alkyl group optionally comprising one or more heteroatoms, a (hetero)cycloalkyl group comprising from 3 to 20 carbon atoms, an arylalkyl group comprising from 7 to 20 carbon atoms anda (hetero)aryl group comprising from 4 to 12 carbon atoms;

n is an integer ranging from 0 to 28;

p is an integer ranging from 0 to 10;

m represents 0 or 1;

q represents 0 or 1;

e is an integer ranging from 1 to 3;

f is an integer or non-integer ranging from 1 to 3;

f is an integer or non-integer ranging from 0 to 2;

the sum f+f represents an integer ranging from 1 to 3;

Z represents a monovalent organic radical Z m , divalent organic radical Z d or trivalent organic radical Z t , having a molar mass or a number-average molecular mass (Mn) ranging from 16 to 22 000 g/mol,

R ac represents a hydrogen atom or a monovalent hydrocarbon radical comprising from 1 to 60 carbon atoms, wherein said radical optionally comprises one or more heteroatoms;

in which:

X 1 represents F 1 or -Ph-XH, or —XH;

X 2 represents F 2 or -Ph-XH, or —XH;

X 3 represents F 3 or -Ph-XH, or —XH;

F 1 represents a radical selected from the group consisting of a hydrogen atom, a linear or branched alkyl group comprising from 1 to 20 carbon atoms, an arylalkyl group comprising from 7 to 20 carbon atoms, a (hetero)aryl group comprising from 4 to 12 carbon atoms, and a (hetero)cycloalkyl group comprising from 3 to 20 carbon atoms, a —COOZ′ group, a —C(O)NH 2 group, an —SMe group, or a guanidyl group of formula —NH—C(═NH)—NH 2 ,

F 2 represents a radical selected from the group consisting of a hydrogen atom, a linear or branched alkyl group comprising from 1 to 20 carbon atoms, an arylalkyl group comprising from 7 to 20 carbon atoms, a (hetero)aryl group comprising from 4 to 12 carbon atoms, and a (hetero)cycloalkyl group comprising from 3 to 20 carbon atoms, a —COOZ′ group, a —C(O)NH 2 group, an —SMe group, or a guanidyl group of formula —NH—C(═NH)—NH 2 ,

F 3 represents a radical chosen from a hydrogen atom, a linear or branched alkyl group comprising from 1 to 20 carbon atoms, an arylalkyl group comprising from 7 to 20 carbon atoms, a (hetero)aryl group comprising from 4 to 12 carbon atoms, and a (hetero)cycloalkyl group comprising from 3 to 20 carbon atoms, a —COOZ m group, a —C(O)NH 2 group, an —SMe group, or a guanidyl group of formula —NH—C(═NH)—NH 2 ,

X, R 1 , R 2 , R 3 , R 4 , n, q, m, p, e and Z′ being as defined for formula (I) above;

G 3 represents a monovalent hydrocarbon radical of molar mass or of number-average molecular mass (Mn) ranging from 14 to 4000 g/mol, wherein said radical optionally comprises one or more heteroatoms;

provided that at most just one radical from among the radicals X 1 , X 2 and X 3 represents —XH or -Ph-XH;

provided that when X 1 =-Ph-XH or —XH, then X 2 =F 2 and X 3 =F 3 ;

provided that when X 2 =-Ph-XH or —XH, then X 1 =F 1 and X 3 =F 3 ;

provided that when X 3 =-Ph-XH or —XH, then X 2 =F 2 and X 1 =F 1 .

15 . A moisture-crosslinkable composition C1 comprising:

at least one compound of formula (X) or (XI) as defined in claim 14 ; and

at least one polymer P comprising at least two NCO end functions or at least one epoxy resin.

16 . An adhesive, sealant or coating composition comprising the composition C1 as claimed in claim 15 .

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 Jun 14, 2022

From: FOUQUAY, STÉPHANE; SANZ, FEDERICO

To: BOSTIK SA

Reel/Frame 060364/0537 →

Priority Claims (1)

EP 19306694 · Dec 19, 2019 · regional

Continuity (1)

Related Publication 20230038642A1 · Feb 9, 2023

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