IP Library › Granted Patent US 12,275,869
Granted Patent B2
US 12,275,869 · App. 16/817,850 · Granted Apr 15, 2025

High strength long open time polyurethane reactive hot melt

Inventors: Yingjie Li (Elgin, IL); Shuhui Qin (Elgin, IL); Jeanne Li (Elgin, IL)
Assignee: Henkel AG & Co. KGaA
C09J175/08C08G18/4018C08G18/4063C08G18/4238C08G18/4277C08G18/4808C08G18/4825C08G18/6225C08G18/6229C08G18/7671C09J5/00C08G2170/20C08K2003/265C09J2475/00
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Quick Facts
Patent No.
US 12,275,869
App. No.
16/817,850
Granted
Apr 15, 2025
Kind
B2
Abstract

Disclosed is a moisture reactive hot melt adhesive composition prepared from a combination comprising a polyisocyanate, at least one polyether polyol polymer, an acrylic polymer, an inorganic filler and a polyester diol having a structure of Formula 1 or of Formula 2. Formula 1 is: H-[O(CH 2 ) m OOC(CH 2 ) n CO] k -O(CH 2 ) m-OH; m and n are each an even integer; m+n=8; m and n are each independently selected from 2, 4 or 6; k is an integer from 9 to 55; and the polyol of Formula 1 has a number average molecular weight of about 2,000 to about 11,000. Formula 2, a polycaprolactone polyol, is: HO-[(CH 2 ) 5 COO] p R 1 -[OOC(CH 2 ) 5 ] q -OH; R 1 is an initiator such as 1,4′-butanediaol, 1,6′-hexanediol, or ethylene glycol; p is an integer from 0 to 96; q is an integer from 0 to 96; p+q=16 to 96; and the polyol has a number average molecular weight of about 2,000 to about 11,000 or less.

Claims (44)

1. A moisture reactive hot melt adhesive composition that is the product of a mixture comprising a polyisocyanate, at least one polyether polyol polymer, an acrylic polymer, from about 10 to about 50% by weight of an inorganic filler, and a having a structure of Formula 2, wherein:

HO-[(CH 2 ) 5 COO] p -R 1 -[OOC(CH 2 ) 5 ] q -OH, wherein:

R 1 is an initiator;

p is an integer from 0 to 96;

q is an integer from 0 to 96;

p+q=16 to 96; and

the polycaprolactone polyol of Formula 2 has a number average molecular weight of from about 2,000 to about 11,000; and

the acrylic polymer is free of active hydrogen groups.

2. The moisture reactive hot melt adhesive composition of claim 1 , wherein R 1 is a residue of a glycol initiator selected from the group consisting of 1,4′-butanediol, 1,6′-hexanediol, ethylene glycol, and any combination thereof.

3. The moisture reactive hot melt adhesive composition of claim 1 , wherein the at least one polyether polyol polymer has a number average molecular weight of from about 2,000 to about 10,000 and is present in an amount of from about 10 to about 35% by weight, based on the total weight of the adhesive composition.

4. The moisture reactive hot melt adhesive composition of claim 1 , wherein the at least one polyether polyol polymer has a number average molecular weight of from about 1,500 to about 6,000 and is present in an amount of from about 15 to about 40% by weight, based on the total weight of the adhesive composition.

5. The moisture reactive hot melt adhesive composition claim 1 , wherein the acrylic polymer has a weight average molecular weight of from 30,000 to 80,000, and is present in an amount of from about 10 to about 40% by weight, based on the total weight of the adhesive composition.

6. The moisture reactive hot melt adhesive composition of claim 1 , wherein the acrylic polymer has a glass transition temperature of from about 35° C. to about 85° C. and a hydroxyl number of less than 8.

7. The moisture reactive hot melt adhesive composition of claim 1 , wherein the polyisocyanate is present in an amount of from about 5 to about 40% by weight, based on the total weight of the adhesive composition.

8. The moisture reactive hot melt adhesive composition of claim 1 , wherein the polyisocyanate comprises 4,4′-methylenebisphenyldiisocyanate.

9. The moisture reactive hot melt adhesive composition of claim 1 , wherein the inorganic filler comprises calcium carbonate.

10. The moisture reactive hot melt adhesive composition of claim 1 , further comprising an additive selected from the group consisting of an additional filler, a plasticizer, a catalyst, a colorant, a rheology modifier, a flame retardant, a UV pigment, a nanofiber, a defoamer, a tackifier, a curing catalyst, an anti-oxidant, an adhesion promoter, a stabilizer, a thixotropic agent, and any mixture thereof.

11. The moisture reactive hot melt adhesive composition of claim 1 , wherein the adhesive composition has an open time of from about 6 to about 10 minutes.

12. The moisture reactive hot melt adhesive composition of claim 1 , wherein the adhesive composition exhibits a green strength of greater than about 120 pounds per square inch (psi) within 30 minutes after application to a substrate.

13. An article of manufacture comprising the moisture reactive hot melt adhesive composition of claim 1 .

14. The moisture reactive hot melt adhesive composition of claim 1 , wherein the adhesive composition consists of:

from about 5 to about 40% by weight of the polyisocyanate;

from about 15 to about 40% by weight of the polyether polyol polymer;

from about 10 to about 40% by weight of the acrylic polymer;

from about 15 to about 50% by weight of the inorganic filler; and

from about 10 to about 35% by weight of the polycaprolactone polyol.

15. The moisture reactive hot melt adhesive composition of claim 1 , wherein the acrylic polymer is free of aminofunctional groups and/or acrylonitrile monomers.

16. The moisture reactive hot melt adhesive composition of claim 1 , wherein the acrylic polymer is a polymer or copolymer formed from acrylates, methacrylates, and any mixture thereof.

17. The moisture reactive hot melt adhesive composition of claim 1 , wherein the at least one polyether polyol polymer comprises a first polypropylene glycol having a number average molecular weight of from about 1500 to about 3000, and a second polypropylene glycol having a number average molecular weight of from about 3000 to about 6000.

18. The moisture reactive hot melt adhesive composition of claim 1 , wherein the adhesive composition:

has an open time of from about 6 to about 10 minutes,

exhibits a green strength of greater than about 120 pounds per square inch (psi) within 30 minutes after application to a substrate,

a yield strength of greater than or equal to 607 psi and/or a tensile strength of greater than or equal to 1415 psi, and

a temperature stability with a storage modulus at 90° C. of equal to or greater than 2.59 E+06.

19. A moisture reactive hot melt adhesive composition that is the product of a mixture comprising a polyisocyanate, at least one polyether polyol polymer, an acrylic polymer, from about 10 to about 50% by weight of an inorganic filler, and a polycaprolactone polyol having a structure of Formula 2, wherein:

Formula 2 is:

HO-[(CH 2 ) 5 COO] p -R 1 -[OOC(CH2) 5 ] q -OH, wherein:

R 1 is an initiator;

p is an integer from 0 to 96;

q is an integer from 0 to 96;

p+q=16 to 96; and

the polycaprolactone polyol of Formula 2 has a number average molecular weight of from about 2,000 to about 11,000; and

the adhesive composition is free of stabilizer and has an open time of between about 6 and about 10 minutes.

20. The moisture reactive hot melt adhesive composition of claim 1 , wherein R 1 is a residue of ethylene glycol.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 12, 2025
From: QIN, SHUHUI; LI, JEANNE; LI, YINGJIE
To: HENKEL IP & HOLDING GMBH
Reel/Frame 070194/0326 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 22, 2022
From: HENKEL IP & HOLDING GMBH
To: HENKEL AG & CO. KGAA
Reel/Frame 059207/0627 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 23, 2020
From: QIN, SHUHUI; LI, JEANNE; LI, YINGJIE
To: HENKEL IP & HOLDING GMBH
Reel/Frame 053009/0134 →
Continuity (3)
Continuation PCTUS2018052121 · Sep 21, 2018
Provisional Application 62561786 · Sep 22, 2017
Related Publication 20200216730A1 · Jul 9, 2020
References Cited (38)
US 4775719A · Markevka et al. · 1988 [cited by applicant]
US 4808255A · Markevka et al. · 1989 [cited by applicant]
US 4999407A · Gilch et al. · 1991 [cited by applicant]
US 5021507A · Stanley · 1991 [cited by examiner]
US 5173538A · Gilch et al. · 1992 [cited by applicant]
US 5827393A · Kinzelmann et al. · 1998 [cited by applicant]
US 5866656A · Hung et al. · 1999 [cited by applicant]
US 6465104B1 · Krebs et al. · 2002 [cited by applicant]
US 6635722B2 · Li · 2003 [cited by examiner]
US 7025853B2 · Kesselmayer · 2006 [cited by applicant]
US 8246777B2 · Pind et al. · 2012 [cited by applicant]
US 9464155B2 · Kanagawa et al. · 2016 [cited by applicant]
US 9487687B2 · Ninomiya et al. · 2016 [cited by applicant]
US 10800957B2 · Schmider et al. · 2020 [cited by applicant]
US 20040010095A1 · Kesselmayer · 2004 [cited by examiner]
US 20130345354A1 · Tamogami · 2013 [cited by examiner]
US 20150322314A1 · Franken · 2015 [cited by examiner]
US 20170058162A1 · Slark et al. · 2017 [cited by applicant]
US 20220235249A1 · Sutyak · 2022 [cited by examiner]
CA 3010144A1 · 2017 [cited by applicant]
CN 1468926A · 2004 [cited by applicant]
CN 101314267A · 2008 [cited by applicant]
CN 103865465A · 2014 [cited by applicant]
CN 106459723A · 2017 [cited by applicant]
EP 0764670A1 · 1997 [cited by applicant]
JP H1036481A1 · 1998 [cited by applicant]
JP 2007211150A · 2007 [cited by applicant]
JP 2008500406A · 2008 [cited by applicant]
JP 2009286883A · 2009 [cited by applicant]
JP 2016088948A · 2016 [cited by applicant]
WO 9216592A1 · 1992 [cited by applicant]
WO 2013153907A1 · 2013 [cited by applicant]
WO 2015045635A1 · 2015 [cited by applicant]
WO 2017004178A1 · 2017 [cited by applicant]
WO 2017103070A1 · 2017 [cited by applicant]
Elvacite 2013 Technical Data Sheet 07132022 (Year: 2022). [cited by examiner]
Evonik http://adhesive-resins.evonik.com/sites/lists/RE/DocumentsAC/DYNACOLL%20brochurel_06_09_2016.pdf. [cited by applicant]
International Search Report for International PCT Patent Application No. PCT/US2018/052121 dated Jan. 13, 2019. [cited by applicant]