Granted Patent B2

US 12,421,345 · App. 17/783,307 · Granted Sep 23, 2025

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

Assignee: BOSTIK SA

C08G18/307C08G18/12C08G18/4808C08G18/606C08G2190/00

Abstract

Claims (60)

1. A moisture-crosslinkable sealant composition comprising:

at least one polyurethane P comprising at least two NCO end functions; and

at least one polyimine A obtained via a process comprising a step of reaction between at least:

a) a (poly) urethane-aldehyde comprising at least 2 aldehyde functions;

b) a primary diamine;

c) optionally in the presence of a primary monoamine or a monoaldehyde if a —CHO/NH 2 molar ratio is other than 1.

2. The composition as claimed in claim 1 , wherein the (poly)urethane-aldehyde a) is obtained by reaction between:

at least one polyisocyanate C; and

at least one hydroxyaldehyde.

3. The composition as claimed in claim 2 , wherein the at least one polyisocyanate C is selected from the group consisting of triisocyanates, diisocyanates and polyurethanes comprising at least two NCO end functions.

4. The composition as claimed in claim 1 , wherein the (poly)urethane-aldehyde a) is a (poly)urethane-dialdehyde comprising an allophanate radical.

5. The composition as claimed in claim 2 , wherein the at least one polyisocyanate C is a HDI allophanate having the following formula (Y1):

6. The composition as claimed in claim 2 , wherein the at least one polyisocyanate C is a polyurethane comprising at least two NCO end functions which is prepared by a process comprising a polyaddition reaction E1):

i. of at least one polyisocyanate;

ii. with at least one polyol,

in amounts such that a NCO/OH molar ratio (r1) is strictly greater than 1;

step E1) using at least one HDI allophanate, having the following formula (Y1):

7. The composition as claimed in claim 2 , wherein the at least one hydroxyaldehydes have one of the following formulae:

with R 6 and R 7 each representing, independently of one another, a monovalent hydrocarbon radical comprising from 1 to 12 carbon atoms, or R 6 and R 7 together form an aliphatic ring comprising from 4 to 12 carbon atoms, said ring being optionally substituted; R 9 representing a hydrogen, a linear or branched alkyl radical, a cycloalkyl radical, an arylalkyl radical, or an alkoxycarbonyl radical comprising from 1 to 12 carbon atoms; R b represents H or a linear or branched alkyl radical comprising from 1 to 7 carbon atoms; u represents an integer ranging from 1 to 380; and t represents an integer ranging from 0 to 18;

wherein:

t is an integer ranging from 0 to 18;

u represents an integer ranging from 1 to 380; and t represents an integer ranging from 0 to 18; and

R b represents H or an alkyl radical ranging from 1 to 7 carbon atoms.

8. The composition as claimed in claim 1 , wherein the (poly)urethane-aldehyde a) has one of the following formulae (I) or (II):

wherein:

R a is as defined above;

R d represents the following radical:

wherein i is an integer ranging from 1 to 2, j is an integer ranging from 0 to 9, r is an integer ranging from 1 to 10, R represents a saturated or unsaturated, cyclic or acyclic, linear or branched, hydrocarbon chain comprising from 1 to 20 carbon atoms, and R 3 represents a linear or branched divalent alkylene group having from 2 to 4 carbon atoms;

R 4 represents a divalent hydrocarbon radical derived from a polyol by replacement of each of the two hydroxyl groups with a free valency;

v is an integer such that the number-average molecular weight of the polyether block of formula -[OR 4] v - ranges from 60 g/mol to 22 000 g/mol;

w is an integer such that the number-average molecular weight (Mn) of the (poly)urethane-dialdehyde of formula (I) ranges from 500 g/mol to 22 000 g/mol.

9. The composition as claimed in claim 1 , wherein the primary diamine is selected from the group consisting of linear or branched aliphatic amines; aliphatic polyamines; polyetheramines; polyamidoamines; dimer fatty amines; derivatives of diamino acids; amines of the following formula (B): H 2 N—CH 2 —Z—CH 2 —NH 2 wherein Z represents a linear or branched, cyclic, aliphatic or aromatic, saturated or unsaturated divalent hydrocarbon radical, said hydrocarbon radical being optionally interrupted by one or more heteroatoms chosen from —S—, —O— and/or one or more tertiary amine divalent groups —NR— with R representing a linear or branched, saturated or unsaturated alkyl group, comprising 1 to 22 carbon atoms; and mixtures thereof.

10. The composition as claimed in claim 1 , wherein a —C═N-aldimine function/-NCO function molar ratio may range from 0.50 to 2.0.

11. The composition as claimed in claim 1 , wherein it further comprises at least one additive selected from the group consisting of plasticizers, solvents, pigments, adhesion promoters, moisture absorbers, UV stabilizers (or antioxidants), molecular sieves, glitter, fluorescent materials, rheological additives, fillers, and mixtures thereof.

12. A polyimine A obtained via a process comprising a step of reaction between at least:

a) a (poly)urethane-aldehyde comprising at least 2 aldehyde functions;

b) a primary diamine;

c) optionally in the presence of a primary monoamine or a monoaldehyde if a —CHO/NH 2 molar ratio is other than 1;

wherein said (poly)urethane-aldehyde a) is a (poly)urethane-dialdehyde comprising an allophanate radical.

13. The polyimine A as claimed in claim 12 , wherein the (poly)urethane-dialdehyde is obtained by reaction between:

at least one polyisocyanate C comprising at least one allophanate radical; and

at least one hydroxyaldehyde.

14. The polyimine A as claimed in claim 13 , wherein the (poly)urethane-dialdehyde is obtained by reaction between:

at least one polyisocyanate C comprising at least one allophanate radical; and

at least one hydroxyaldehyde;

in amounts such that a NCO/OH molar ratio (r2) ranges from 0.95 to 1.05.

15. The polyimine as claimed in claim 13 , wherein the at least one polyisocyanate C is the HDI allophanate having the following formula (Y1):

16. The polyimine as claimed in claim 13 , wherein the at least one polyisocyanate C is a polyurethane comprising at least two NCO end functions which is prepared by a process comprising a polyaddition reaction E1):

i. of at least one polyisocyanate;

ii. with at least one polyol,

in amounts such that a NCO/OH molar ratio (r1) is strictly greater than 1;

step E1) using at least one HDI allophanate, having the following formula (Y1):

17. The polyimine A as claimed in claim 12 , wherein the (poly)urethane-aldehyde a) has one of the following formulae (I) or (II):

wherein:

R a is as defined above;

R d represents the following radical:

wherein i is an integer ranging from 1 to 2, j is an integer ranging from 0 to 9, r is an integer ranging from 1 to 10, R represents a saturated or unsaturated, cyclic or acyclic, linear or branched, hydrocarbon chain comprising from 1 to 20 carbon atoms, and R 3 represents a linear or branched divalent alkylene group having from 2 to 4 carbon atoms;

R 4 represents a divalent hydrocarbon radical derived from a polyol by replacement of each of the two hydroxyl groups with a free valency;

v is an integer such that the number-average molecular weight of the polyether block of formula -[OR 4] v -ranges from 60 g/mol to 22 000 g/mol;

w is an integer such that the number-average molecular weight (Mn) of the (poly)urethane-dialdehyde of formula (I) ranges from 500 g/mol to 22 000 g/mol.

Assignments (2)

Priority Claims (1)

Continuity (1)

References Cited (9)