IP Library Granted Patent US 12,252,636
Granted Patent B2
US 12,252,636 · App. 17/451,331 · Granted Mar 18, 2025

Two-component solvent free polyurethane laminating adhesive composition

Inventors: Nan Zhang (Shanghai, CN); Jingjing Liang (Shanghai, CN); Guan Yew Low (Shanghai, CN); Grant Kenion (Easton, PA)
Assignee: Henkel AG & Co. KGaA
C09J175/04C08G18/42C08G18/4825C08G18/4833C08G18/73C09J5/00C09J2475/00
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Quick Facts
Patent No.
US 12,252,636
App. No.
17/451,331
Granted
Mar 18, 2025
Kind
B2
Abstract

The present invention provides a two-component solvent free polyurethane adhesive composition, comprising: (A) a OH-containing component, and (B) an NCO-containing component; wherein the mass ratio between the OH-containing component (A) and the NCO-containing component (B) is greater than 1:1, and the molar ratio between the OH group in the component (A) and the NCO group in the component (B) is less than 1:1.

Claims (36)

1. A two-component, solvent free polyurethane adhesive composition comprising:

(A) an OH-containing component; and

(B) a NCO-containing component, wherein:

the mass ratio between the OH-containing component (A) and the NCO-containing component (B) is greater than 1:1,

the molar ratio between the OH group in the OH-containing component (A) and the NCO group in the NCO-containing component (B) is less than 1:1, and

the OH-containing component (A) comprises at least 90 wt. % of one or more polyether-ester polyols having a hydroxyl value of 70 to 150 mg KOH/g.

2. The composition of claim 1 , wherein the NCO-containing component (B) has an NCO group content of 8 wt. % to 25 wt. %, based on the total weight of the NCO-containing component (B).

3. The composition of claim 1 , wherein the NCO-containing component (B) consists essentially of one or more NCO-terminated polyurethane prepolymers having an NCO group content of 8 wt. % to 25 wt. %.

4. The composition claim 1 , wherein the one or more polyether-ester polyols comprises repeat units derived from at least one of:

one or more polycarboxylic acids,

one or more C 2 -C 15 monomeric polyols, or

one or more polyols containing ether groups with a number average molecular weight (Mn) of 200 Da to 4000 Da.

5. The composition of claim 4 , wherein the one or more polycarboxylic acids are selected from the group consisting of C 1 -C 15 aliphatic dicarboxylic acids, C 6 -C 20 aromatic dicarboxylic acids, 2,6-naphthalenedicarboxylic acid, and any mixture thereof.

6. The composition of claim 4 , wherein the one or more polycarboxylic acids are selected from the group consisting of malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, sebacic acid, dodecanedioic acid, azelaic acid, phthalic acid, isophthalic acid, terephthalic acid, diphenic acid, 2,6-naphthalenedicarboxylic acid, and any mixture thereof.

7. The composition of claim 4 , wherein the one or more C 2 -C 15 monomeric polyols are selected from the group consisting of ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, butylene glycol, dibutylene glycol, tributylene glycol, pentylene glycol, dipentylene glycol, tripentylene glycol, glycerin, trimethylolpropane, 2-methylpropylene glycol, and any mixture thereof.

8. The composition of claim 4 , wherein the one or more polyols containing ether groups are selected from the group consisting of polyethylene glycol, polypropylene glycol, polybutylene glycol, polypentylene glycol, polyhexylene glycol, poly(ethylene oxide-co-propylene oxide) glycol, poly(ethylene oxide-co-butylene oxide) glycol, poly(ethylene oxide-co-pentylene oxide) glycol, poly(ethylene oxide-co-hexylene oxide) glycol, poly(propylene oxide-co-butylene oxide) glycol, poly(propylene oxide-co-pentylene oxide) glycol, poly(propylene oxide-co-hexylene oxide) glycol, poly(butylene oxide-co-pentylene oxide) glycol, poly(butylene oxide-co-hexylene oxide) glycol, and poly(pentylene oxide-co-hexylene oxide) glycol, and any mixture thereof.

9. The composition of claim 4 , wherein the one or more polyether-ester polyols have a viscosity in the range of 500 mPa·s to 10000 mPa·s at 25° C.

10. The composition of claim 1 , wherein the OH-containing component (A) has a viscosity in the range of 500 mPa·s to 10000 mPa·s at 25° C.

11. The composition of claim 1 , wherein the mass ratio between the OH-containing component (A) and the NCO-containing component (B) is in the range of 1:1 to 1:2.

12. The composition of claim 1 , wherein the molar ratio between the OH group in the OH-containing component (A) and the NCO group in the NCO-containing component (B) is in the range of 1:1.2 to 1:2.

13. The composition of claim 1 , wherein the NCO-containing component (B) comprises at least 95 wt. % of one or more NCO-terminated polyurethane prepolymers based on the total weight of the NCO-containing component (B).

14. A cured reaction product comprising the two-component, solvent free polyurethane adhesive composition of claim 1 .

15. An article comprising the cured reaction product of claim 14 .

16. A method of bonding two flexible substrates, the method comprising:

mixing an OH-containing component (A) and a NCO-containing component (B) to form a mixed adhesive composition, wherein:

the mass ratio between the OH-containing component (A) and the NCO-containing component (B) is greater than 1:1,

the molar ratio between the OH group in the OH-containing component (A) and the NCO group in the NCO-containing component (B) is less than 1:1, and

the OH-containing component (A) comprises at least 90 wt. % of one or more polyether-ester polyols having a hydroxyl value of 70 to 150 mg KOH/g;

applying the mixed adhesive composition to at least a first substrate; and

laminating the first substrate with the applied mixed adhesive composition to a second substrate.

17. The composition of claim 1 , wherein the OH-containing component (A) comprises 100 wt. % of one or more polyether-ester polyols having a hydroxyl value of 70 to 150 mg KOH/g.

18. The composition of claim 4 , wherein:

(i) the one or more polycarboxylic acids are selected from the group consisting of adipic acid, isophthalic acid, and a combination thereof,

(ii) the one or more C 2 -C 15 monomeric polyols are selected from the group consisting of diethylene glycol, glycerl, and a combination thereof, and

(iii) the one or more polyols containing ether groups are selected from the group consisting of polypropylene glycol, poly(ethylene coxide-copropylene oxide) glycol, and a combination thereof.

19. The composition of claim 1 , wherein the molar ratio between the OH group in the OH-containing component (A) and the NCO group in the NCO-containing component (B) is about 1:1.5.

Assignments (6)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 15, 2025
From: LIANG, JINGJING
To: HENKEL (CHINA) INVESTMENT CO., LTD.
Reel/Frame 069880/0209 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 15, 2025
From: LOW, YEW GUAN
To: HENKEL (CHINA) INVESTMENT CO., LTD.
Reel/Frame 069880/0379 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 15, 2025
From: ZHANG, NAN
To: HENKEL (CHINA) INVESTMENT CO., LTD.
Reel/Frame 069881/0325 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 15, 2025
From: KENION, GRANT
To: HENKEL IP & HOLDING GMBH
Reel/Frame 069881/0614 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 15, 2025
From: HENKEL (CHINA) INVESTMENT CO., LTD.
To: HENKEL AG & CO. KGAA
Reel/Frame 069882/0029 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 22, 2022
From: HENKEL IP & HOLDING GMBH
To: HENKEL AG & CO. KGAA
Reel/Frame 059207/0627 →
Continuity (2)
Continuation PCTCN2019084037 · Apr 24, 2019
Related Publication 20220162485A1 · May 26, 2022
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