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US 12,516,147 B2Granted
Aldimines and uses thereof
AssigneeBostik SA
InventorsStéphane Fouquay, Federico Sanz
Life of this patent
Estimating the term…
Abstract
The present invention relates to compounds having one of the following formulae (I) and (II): and also to the uses thereof.
Claims16
A compound having one of the following formulae (I) and (II):
- in which:
- X1 represents F1 or —N═C(H)-G1 or -Ph-XH, or —XH, with X representing O or S or Se and Ph representing a phenyl group;
- X2 represents F2 or —N═C(H)-G1 or -Ph-XH, or —XH, with X representing O or S or Se and Ph representing a phenyl group;
- X3 represents F3 or —N═C(H)-G1 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 X1, X2 and X3 represents —N═C(H)-G1;
- provided that at most just one radical from among the radicals X1, X2 and X3 represents —XH or -Ph-XH;
- provided that when X1=—N═C(H)-G1, then q=1;
- provided that when X1=—N═C(H)-G1 or -Ph-XH or —XH, then X2=F2 and X3=F3;
- provided that when X2=—N═C(H)-G1 or -Ph-XH or —XH, then X1=F1 and X3=F3;
- provided that when X3=—N═C(H)-G1 or -Ph-XH or —XH, then X2=F2 and X1=F1;
- F1 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)NH2 group, an —SMe group, or a guanidyl group of formula —NH—C(═NH)—NH2,
- F2 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)NH2 group, an —SMe group, or a guanidyl group of formula —NH—C(═NH)—NH2,
- F3 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)NH2 group, an —SMe group, or a guanidyl group of formula —NH—C(═NH)—NH2,
- R1, R2, R3 and R4 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 Zd or trivalent organic radical Zt, having a molar mass or a number-average molecular mass (Mn) ranging from 16 to 22 000 g/mol,
- Rac 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;
- G1 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 G1 does not represent a substituted or unsubstituted aryl radical;
- in which:
- X1 represents F1 or -Ph-XH, or —XH;
- X2 represents F2 or -Ph-XH, or —XH;
- X3 represents F3 or -Ph-XH, or —XH;
- F1 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)NH2 group, an —SMe group, or a guanidyl group of formula —NH—C(═NH)—NH2,
- F2 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)NH2 group, an —SMe group, or a guanidyl group of formula —NH—C(═NH)—NH2,
- F3 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)NH2 group, an —SMe group, or a guanidyl group of formula —NH—C(═NH)—NH2,
- X, R1, R2, R3, R4, n, q, m, p, e and Z′ being as defined for formula (I) above;
- G3 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 G3 does not represent a substituted or unsubstituted arylene radical;
- provided that at most just one radical from among the radicals X1, X2 and X3 represents —XH or -Ph-XH;
- provided that when X1=-Ph-XH or —XH, then X2=F2 and X3=F3;
- provided that when X2=-Ph-XH or —XH, then X1=F1 and X3=F3;
- provided that when X3=-Ph-XH or —XH, then X2=F2 and X1=F1.
35 more elements
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:
- X1 represents F1 or —N═C(H)-G1 or -Ph-XH, or —XH, with X representing 0 or S or Se and Ph representing a phenyl group;
- X2 represents F2 or —N═C(H)-G1 or -Ph-XH, or —XH, with X representing 0 or S or Se and Ph representing a phenyl group;
- X3 represents F3 or —N═C(H)-G1 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 X1, X2 and X3 represents —N═C(H)-G1;
- provided that at most just one radical from among the radicals X1, X2 and X3 represents —XH or -Ph-XH;
- provided that when X1=—N═C(H)-G1, then q=1;
- provided that when X1=—N═C(H)-G1 or -Ph-XH or —XH, then X2=F2 and X3=F3;
- provided that when X2=—N═C(H)-G1 or -Ph-XH or —XH, then X1=F1 and X3=F3;
- provided that when X3=—N═C(H)-G1 or -Ph-XH or —XH, then X2=F2 and X1=F1;
- F1 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)NH2 group, an —SMe group, or a guanidyl group of formula —NH—C(═NH)—NH2,
- F2 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)NH2 group, an —SMe group, or a guanidyl group of formula —NH—C(═NH)—NH2,
- F3 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)NH2 group, an —SMe group, or a guanidyl group of formula —NH—C(═NH)—NH2,
- R1, R2, R3 and R4 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 Zm, divalent organic radical Zd or trivalent organic radical Zt, having a molar mass or a number-average molecular mass (Mn) ranging from 16 to 22 000 g/mol,
- Rac 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;
- G1 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;
- in which:
- X1 represents F1 or -Ph-XH, or —XH;
- X2 represents F2 or -Ph-XH, or —XH;
- X3 represents F3 or -Ph-XH, or —XH;
- F1 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)NH2 group, an —SMe group, or a guanidyl group of formula —NH—C(═NH)—NH2,
- F2 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)NH2 group, an —SMe group, or a guanidyl group of formula —NH—C(═NH)—NH2,
- F3 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 —COOZm group, a —C(O)NH2 group, an —SMe group, or a guanidyl group of formula —NH—C(═NH)—NH2,
- X, R1, R2, R3, R4, n, q, m, p, e and Z′ being as defined for formula (I) above;
- G3 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 X1, X2 and X3 represents —XH or -Ph-XH;
- provided that when X1=-Ph-XH or —XH, then X2=F2 and X3=F3;
- provided that when X2=-Ph-XH or —XH, then X1=F1 and X3=F3;
- provided that when X3=-Ph-XH or —XH, then X2=F2 and X1=F1.
35 more elements
Dependencies are inferred from the claim text.