Retort adhesive composition

Patent metadata

Field	Value
Publication number	US-12344774-B2
Application number	US-202017621230-A
Country	US
Kind code	B2
Filing date	May 19, 2020
Priority date	Jun 18, 2019
Publication date	Jul 1, 2025
Grant date	Jul 1, 2025

Abstract

A solvent-based polyurethane retort adhesive composition for producing laminates including: (A) at least one isocyanate compound, Component A; and (B) at least one isocyanate (NCO)-reactive component, Component B, comprising (i) at least one phosphate ester compound and (ii) at least one polyester polyol having an average molecular weight of greater than 3,000 g/mol; a process for producing the above adhesive; a multi-layer laminate product including the above adhesive; and a process for producing a laminate product using the above adhesive.

First claim

What is claimed is:

1. A solvent-based retort adhesive composition comprising:
(A) an isocyanate compound, Component A, wherein the isocyanate compound, Component A, consists of a single aliphatic-based isocyanate; or wherein the isocyanate compound, Component A, consists of a single aromatic-based isocyanate; and
(B) an isocyanate-reactive component, Component B; comprising:
(i) at least one phosphate ester compound,
(ii) an aliphatic polyester polyol having an average molecular weight of greater than or equal to 3,000 g/mol, and
(iii) an optional polyether polyol, wherein (B)(i), (B)(ii), and (B)(iii) amount to 100 wt % of the isocyanate-reactive component (B).

2. The adhesive of claim 1 , wherein the isocyanate compound, Component A, is the single aliphatic-based isocyanate.

3. The adhesive of claim 1 , wherein the isocyanate compound, Component A is the single aromatic-based isocyanate.

4. The adhesive of claim 1 , wherein the at least one phosphate ester compound component (i) of Component B, is selected from the group consisting of: a phosphate ester compound having the following Structure (I):

wherein R 1 is an organic group, wherein R 1 may or may not have one or more additional pendant —OH groups, wherein R 1 may or may not have one or more additional pendant groups of Structure (I), and wherein two or more of the —OH groups and the group(s) of Structure (I) may or may not be attached to the same atom of R 1 ; a phosphate ester compound containing urethane linkages; and mixtures thereof.

5. The adhesive of claim 1 , wherein Component B consists of
(i) the phosphate ester compound, and
(ii) the aliphatic polyester polyol.

6. The adhesive of claim 1 , wherein the isocyanate-reactive component, Component B, includes further (iii) the polyether polyol having an average molecular weight less than 1,500 g/mol.

7. The adhesive of claim 1 , further comprising (C) from 40 wt % to 70 wt % of at least one solvent selected from the group consisting of ethyl acetate, methyl ether ketone, toluene, and mixtures thereof, and weight percent is based on the total weight of the composition,
wherein Component (A), Component (B), and the solvent (C) amount to 100 wt % of the adhesive composition.

8. The adhesive of claim 2 , wherein the single aliphatic-based isocyanate is a hexamethylene diisocyanate-based polyisocyanate.

9. The adhesive of claim 3 , wherein the single aromatic-based isocyanate is a xylylene diisocyanate-based polyisocyanate.

10. A solvent-based retort adhesive composition comprising:
(A) an isocyanate compound, Component A, wherein the isocyanate compound, Component A, is a blend consisting of (i) a single aliphatic-based isocyanate and (ii) a single aromatic-based isocyanate; and
(B) an isocyanate-reactive component, Component B; comprising
(i) at least one phosphate ester compound,
(ii) an aliphatic polyester polyol having an average molecular weight of greater than or equal to 3,000 g/mol, and
(iii) an optional polyether polyol, wherein (B) (i), (B) (ii), and (B) (iii) amount to 100 wt % of the isocyanate-reactive component (B).

11. The adhesive of claim 10 wherein the single aliphatic-based isocyanate is a hexamethylene diisocyanate-based polyisocyanate.

12. The adhesive of claim 11 wherein the single aromatic-based isocyanate is a xylylene diisocyanate-based polyisocyanate.

13. The adhesive of claim 12 further comprising
(C) from 40 wt % to 70 wt % of at least one solvent selected from the group consisting of ethyl acetate, methyl ether ketone, toluene, and mixtures thereof, and weight percent is based on the total weight of the composition,
wherein Component (A), Component (B), and the solvent (C) amount to 100 wt % of the adhesive composition.

14. A solvent-based retort adhesive composition comprising:
(A) an isocyanate compound, Component A, wherein the isocyanate compound, Component A, is a blend consisting of (i) a first aromatic-based isocyanate and (ii) a second aromatic-based isocyanate different than the first aromatic-based isocyanate; and
(B) an isocyanate-reactive component, Component B; comprising:
(i) at least one phosphate ester compound,
(ii) an aliphatic polyester polyol having an average molecular weight of greater than or equal to 3,000 g/mol, and
(iii) an optional polyether polyol, wherein (B) (i), (B) (ii), and (B) (iii) amount to 100 wt % of the isocyanate-reactive component (B).

15. The adhesive of claim 14 wherein the first aromatic-based isocyanate is a diphenylmethane diisocyanate.

16. The adhesive of claim 15 wherein the second aromatic-based isocyanate is a xylylene diisocyanate-based polyisocyanate.

17. The adhesive of claim 16 further comprising
(C) from 40 wt % to 70 wt % of at least one solvent selected from the group consisting of ethyl acetate, methyl ether ketone, toluene, and mixtures thereof, and weight percent is based on the total weight of the composition,
wherein Component A, Component B, and the solvent (C) amount to 100 wt % of the adhesive composition.

Assignees

• Dow Global Technologies Llc
• Rohm & Haas
• Arkema France

Inventors

• Wu Jie
• Chen Mai
• Dewasthale Sudhanwa D

Classifications

• C08G18/7671 Primary

  containing only one alkylene bisphenyl group · CPC title

• C08G18/7642

  containing at least two isocyanate or isothiocyanate groups linked to the aromatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate groups, e.g. xylylene diisocyanate or homologues substituted on the aromatic ring · CPC title

• C08G18/73

  acyclic · CPC title

• C08G18/5084

  Phosphate compounds · CPC title

• C08G18/4829

  Polyethers containing at least three hydroxy groups (C08G18/4833 - C08G18/5096 take precedence) · CPC title