IP Library Granted Patent US 12,545,823
Granted Patent B2
US 12,545,823 · App. 17/604,794 · Granted Feb 10, 2026

Lamination adhesive for sterilisation

Inventors: Francis Pardal (Venette, FR); David Penet (Venette, FR)
Assignee: BOSTIK SA
C09J175/06C08G18/10C08G18/4216C08G18/425C08J7/042
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,545,823
App. No.
17/604,794
Granted
Feb 10, 2026
Kind
B2
Abstract

A solvent-based two-component polyurethane-type adhesive composition comprises an —OH component and an —NCO component. The —OH component comprises an amorphous prepolymer including two —OH end groups, with a number-average molar mass M n of 8000 to 12,000 g and is chosen from: a) a copolyester (A1) obtained by a polycondensation reaction of at least one aliphatic diol (i) with at least one aromatic diacid (ii) and at least one aliphatic diacid (iii); and b) a polyurethane (A2) obtained by a polyaddition reaction between an aliphatic diisocyanate compound and an amorphous copolyester diol with a number-average molecular weight M n ranging from 4000 to 11 500 g/mol. The —NCO component comprises a compound (B1) including three —NCO end groups, obtained by the reaction of meta-xylylene diisocyanate (m-XDI) with a triol, said compound (B1) being alone or as a mixture with a compound (B2) derived from an aliphatic diisocyanate.

Claims (34)

1 . A solvent-based two-component polyurethane adhesive composition, comprising an —OH component and an —NCO component, such that:

the —OH component is a composition (A) comprising an amorphous prepolymer which includes two —OH end groups, the number-average molar mass M n of which ranges from 8000 to 12,000 g/mol and which is chosen from:

a copolyester (A1) obtained by a polycondensation reaction:

of at least one aliphatic diol (i); with

at least one aromatic diacid (ii) chosen from terephthalic acid, isophthalic acid, phthalic acid and one of their diester or anhydride derivatives; and

at least one aliphatic diacid (iii) or one of its diester or anhydride derivatives; and

a polyurethane (A2) obtained by a polyaddition reaction between an aliphatic diisocyanate compound (A2.P1) and an amorphous copolyester diol (A2.P2), the number-average molecular weight M n of which ranges from 4000 to 11 500 g/mol, said copolyester being obtained by the polycondensation reaction as defined above for (A1); and

the component —NCO is a composition (B) comprising a compound (B1) which includes three —NCO end groups, and which is obtained by the reaction of meta-xylylene diisocyanate (m-XDI) with a triol, said compound (B1) being:

either the only compound comprised in (B) including three-NCO end groups;

or else a mixture with another compound (B2) including three-NCO end groups, (B2) being an isocyanurate (B2-1) of an aliphatic diisocyanate and the content of (B1) in said mixture being at least 40% by weight, based on the total weight of said mixture.

2 . The adhesive composition as claimed in claim 1 , wherein the amorphous prepolymer included in the composition (A) is the amorphous copolyester diol (A1) and the diol (i) is selected from the group consisting of ethylene glycol, diethylene glycol, trimethylene glycol, hexamethylene glycol, propylene glycol, propane-1,3-diol, (1,4-, 1,3- or 1,2-) butanediol, neopentyl glycol, 2-methyl-1,3-propanediol, hexanediol and cyclohexanedimethanol.

3 . The adhesive composition as claimed in claim 2 , wherein the aliphatic diacid (iii) is selected from the group consisting of adipic acid, azelaic acid, sebacic acid, cyclohexanedicarboxylic acid, dodecanedicarboxylic acid, 1,10-decanedicarboxylic acid and succinic acid.

4 . The adhesive composition as claimed in claim 2 , wherein the copolyester diol (A1) is obtained by polycondensation:

of two aliphatic diols (i) consisting respectively of ethylene glycol and diethylene glycol; with

two diacids (ii) consisting respectively of terephthalic acid and isophthalic acid; and

adipic acid as aliphatic diacid (iii).

5 . The adhesive composition as claimed in claim 1 , wherein the compound (B1) is the only compound comprised in the composition (B) including three-NCO end groups.

6 . The adhesive composition as claimed in claim 1 , wherein the compound (B1) is the adduct of m-XDI and of trimethylolpropane (TMP).

7 . The adhesive composition as claimed in claim 1 , wherein the compound (B1) is as a mixture with the compound (B2).

8 . The adhesive composition as claimed in claim 7 , wherein the compound (B2) is an isophorone diisocyanate (IPDI) derivative.

9 . The adhesive composition as claimed in claim 7 , wherein the composition (B) comprises a mixture of:

the adduct (B1) of m-XDI and of trimethylolpropane (TMP); and of

IPDI isocyanurate as compound (B2).

10 . The adhesive composition as claimed in claim 7 , wherein the content of (B1) in the mixture of (B1) and (B2) is within a range extending from 40% to 80% weight/weight.

11 . The adhesive composition as claimed in claim 1 , wherein the composition further comprises an adhesion promoter included in the —NCO component or in the —OH component.

12 . The adhesive composition as claimed in claim 11 , wherein the adhesion promoter is an aminosilane.

13 . The adhesive composition as claimed in claim 1 , wherein the amounts of the —NCO and —OH components are such that the —NCO/—OH molar equivalent ratio is within a range extending from 3 to 5.

14 . A multilayer film comprising two thin layers of material bonded together by a continuous layer, wherein said layer is constituted by the two-component adhesive composition as defined in claim 1 in the crosslinked state, in a proportion of an amount of less than 7 g/m 2 .

15 . A process for the continuous preparation of the multilayer film as defined in claim 14 , comprising the sequential stages of:

(i) combining the —NCO and —OH components and, if appropriate, diluting with a solvent, in order to form an adhesive mixture;

(ii) coating, with said adhesive mixture, a first thin layer of material in the form of a substantially continuous layer;

(iii) evaporating the organic solvent;

(iv) laminating a second thin layer over the first thin layer coated in accordance with stage (ii), then

(v) crosslinking the adhesive mixture.

Assignments (3)
CHANGE OF ADDRESS Recorded Jul 30, 2025
From: BOSTIK SA
To: BOSTIK SA
Reel/Frame 072277/0238 →
INVENTOR'S OBLIGATION TO ASSIGN TO EMPLOYER WITH TRANSLATION PROVIDED Recorded Aug 28, 2024
From: PENET, DAVID
To: BOSTIK SA
Reel/Frame 068794/0760 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 4, 2022
From: PARDAL, FRANCIS
To: BOSTIK SA
Reel/Frame 060716/0621 →
Priority Claims (1)
FR 1904454 · Apr 26, 2019 · national
Continuity (1)
Related Publication 20220204825A1 · Jun 30, 2022
References Cited (8)
US 5478897A · Sasano et al. · 1995 [cited by applicant]
US 20190004336A1 · Mori · 2019 [cited by examiner]
EP 1283232A2 · 2003 [cited by applicant]
EP 1985679A1 · 2008 [cited by applicant]
EP 3101044A1 · 2016 [cited by applicant]
WO 2015093583A1 · 2015 [cited by applicant]
WO 2015095583A1 · 2015 [cited by applicant]
ISA/EP; International Search Report and Written Opinion for International Patent Application No. PCT/FR2020/050690 dated Sep. 3, 2020, 10 pages. [cited by applicant]