IP Library Granted Patent US 12,203,013
Granted Patent B2
US 12,203,013 · App. 17/466,001 · Granted Jan 21, 2025

Two-part, cyanoacrylate/cationically curable adhesive systems

Inventors: Aine Mooney (Dublin, IE); Susan Reilly (Clane, IE); Deborah Moore (Bray, IE)
Assignee: Henkel AG & Co. KGaA
C09J4/06C08F4/14C08F20/34C08K3/36C08L63/00C08K2201/006C08K2201/011C09J133/06
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 12,203,013
App. No.
17/466,001
Granted
Jan 21, 2025
Kind
B2
Abstract

Two-part cyanoacrylate/cationically curable adhesive systems, are provided.

Claims (28)

1. A two-part curable composition comprising:

(a) a first part comprising a cyanoacrylate component, a silica having hydrophobic groups that comprise organosilane groups and hydrophilic groups on a surface thereof that comprise silanol groups, and a cationic catalyst; and

(b) a second part comprising a cationic curable component, wherein when mixed together the cationic catalyst initiates cure of the cationic curable component.

2. The composition of claim 1 , wherein the cyanoacrylate component comprises H 2 C═C(CN)—COOR, wherein R is selected from alkyl, alkoxyalkyl, cycloalkyl, alkenyl, aralkyl, aryl, allyl and haloalkyl groups.

3. The composition of claim 1 , wherein the cationic catalyst comprises salts of lithium and metals from Group Il of the Periodic Table, and non-nucleophilic acids.

4. The composition of claim 1 , wherein the cationic catalyst is a non-nucleophilic acid having a pH of less than 1.0 when measured as a 10% by weight solution in water.

5. The composition of claim 1 , wherein the cationic catalyst is a member selected from the group consisting of fluoroboric, fluoroarsenic, fluoroantimonic and fluorophosphoric acids; lithium tetrafluoroborate, calcium di-tetrafluoroborate, magnesium di-tetrafluoroborate, lithium hexafluorophosphate, calcium di-hexafluorophosphate, magnesium di-hexafluorophosphate, lithium hexafluoroantimonate and lithium hexafluoroarsenate; lanthanide triflate salts, aryl iodonium salts, aryl sulfonium salts, lanthanum triflate, ytterbium triflate, trimethoxyboroxine, trimethoxyboroxine-aluminum acetyl acetonate, amine-boron trihalide complexes, quaternary ammonium salts, quaternary phosphonium salts, tri-aryl sulfonium salts, di-aryl iodonium salts, and diazonium salts; trialkoxyboroxine curing agents; and combinations thereof.

6. The composition of claim 1 , wherein the cationic curable component is selected from an epoxy component, an episulfide component, an oxetane component, a vinyl ether component and combinations thereof.

7. The composition of claim 1 , wherein the cationic curable component is an epoxy component selected from the group consisting of cycloaliphatic epoxy, aromatic epoxy, aliphatic epoxy and hydrogenated aromatic epoxy.

8. The composition of claim 7 , wherein the epoxy component comprises a member selected from the group consisting of epoxy-functionalized hydrogenated bisphenol-A, bisphenol-F, bisphenol-E, bisphenol-S and biphenyl.

9. The composition of claim 1 , wherein the first part is housed in a first chamber of a dual chamber syringe and the second part is housed in a second chamber of the dual chamber syringe.

10. The composition of claim 1 , wherein the first part further comprises phosphoric acid.

11. The composition of claim 1 , wherein the second part further comprises at least one of a plasticizer, a filler, a thixotrope and a toughener.

12. The composition of claim 11 , wherein the toughener is a member selected from the group consisting of (1) (a) reaction products of the combination of ethylene, methyl acrylate and monomers having carboxylic acid cure sites, (2) (b) dipolymers of ethylene and methyl acrylate, (3) combinations of (a) and (b), (4) vinylidene chloride-acrylonitrile copolymers, (5) and vinyl chloride/vinyl acetate copolymer, (6) copolymers of polyethylene and polyvinyl acetate, and combinations thereof.

13. The composition of claim 1 , wherein the first part and the second part are present in a ratio of about 1:1 by volume.

14. The composition of claim 1 , wherein the first part and the second part are each housed in a separate chamber of a dual chambered container.

15. The composition of claim 1 , wherein the hydrophobic groups on a surface of the silica comprise alkyltrialkoxysilane groups.

16. The composition of claim 1 , wherein the hydrophobic groups on a surface of the silica comprise alkyltrimethoxysilane groups.

17. The composition of claim 1 , wherein the hydrophobic groups on a surface of the silica comprise hexadecyltrimethoxysilane groups.

18. A composition comprising a cyanoacrylate component, a silica having hydrophobic groups that comprise organosilane groups and hydrophilic groups on a surface thereof that comprise silanol groups, and a cationic catalyst.

19. The composition of claim 18 , wherein the silica has a BET surface area of 170-210 and a carbon content of 0.9-1.8%.

20. The composition of claim 18 , wherein the silica is after-treated with hexadecyl silane.

21. A two-part curable composition comprising:

(a) a first part comprising a cyanoacrylate component, a silica having hydrophobic groups and hydrophilic groups on a surface thereof, and a cationic catalyst; and

(b) a second part comprising a cationic curable component,

wherein when mixed together the cationic catalyst initiates cure of the cationic curable component;

wherein the silica has a BET surface area of 170-210 and a carbon content of 0.9-1.8% and is after-treated with hexadecyl silane; and

wherein the cationic catalyst is selected from lithium tetrafluoroborate, calcium di-tetrafluoroborate, magnesium di-tetrafluoroborate, lithium hexafluorophosphate, calcium di-hexafluorophosphate, magnesium di-hexafluorophosphate, lithium hexafluoroantimonate and lithium hexafluoroarsenate.

Assignments (3)
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 Feb 3, 2022
From: MOONEY, AINE; MOORE, DEBORAH; REILLY, SUSAN
To: HENKEL IRELAND OPERATIONS & RESEARCH LIMITED
Reel/Frame 058870/0436 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 3, 2022
From: HENKEL IRELAND OPERATIONS & RESEARCH LIMITED
To: HENKEL IP & HOLDING GMBH
Reel/Frame 058870/0480 →
Priority Claims (1)
GB 1902903 · Mar 4, 2019 · national
Continuity (2)
Continuation PCTEP2020054946 · Feb 25, 2020
Related Publication 20210395571A1 · Dec 23, 2021
References Cited (43)
US 4102945A · Gleave · 1978 [cited by applicant]
US 4336367A · Morris et al. · 1982 [cited by applicant]
US 4419496A · Henton et al. · 1983 [cited by applicant]
US 4440910A · O'Connor · 1984 [cited by applicant]
US 4444933A · Columbus et al. · 1984 [cited by applicant]
US 4477607A · Thompson et al. · 1984 [cited by applicant]
US 4556700A · Harris et al. · 1985 [cited by applicant]
US 4622414A · Mckervey · 1986 [cited by applicant]
US 4636539A · Harris et al. · 1987 [cited by applicant]
US 4695615A · Leonard et al. · 1987 [cited by applicant]
US 4718966A · Harris et al. · 1988 [cited by applicant]
US 4778851A · Henton et al. · 1988 [cited by applicant]
US 4837260A · Sato et al. · 1989 [cited by applicant]
US 4855461A · Harris et al. · 1989 [cited by applicant]
US 4906317A · Liu · 1990 [cited by applicant]
US 5312864A · Wenz et al. · 1994 [cited by applicant]
US 5382635A · Mcinnis et al. · 1995 [cited by applicant]
US 5506283A · Mcinnis et al. · 1996 [cited by applicant]
US 5530037A · Mcdonnell et al. · 1996 [cited by applicant]
US 5693714A · Bauman et al. · 1997 [cited by applicant]
US 5969053A · Bauman et al. · 1999 [cited by applicant]
US 5981659A · Geck et al. · 1999 [cited by applicant]
US 6111015A · Eldin et al. · 2000 [cited by applicant]
US 6147142A · Geck et al. · 2000 [cited by applicant]
US 6180693B1 · Tang et al. · 2001 [cited by applicant]
US 6429281B1 · Dershem et al. · 2002 [cited by applicant]
US 6607632B1 · Mcdonnell et al. · 2003 [cited by applicant]
US 6617400B2 · Yeager et al. · 2003 [cited by applicant]
US 7777064B2 · Mizori · 2010 [cited by applicant]
US 8742048B2 · Hersee et al. · 2014 [cited by applicant]
US 9499978B2 · Glancy · 2016 [cited by applicant]
US 20100305236A1 · Scholz · 2010 [cited by examiner]
US 20130053497A1 · Tully et al. · 2013 [cited by applicant]
US 20140275419A1 · Ward · 2014 [cited by examiner]
CN 103228747A · 2013 [cited by applicant]
EP 0209067 · 1987 [cited by applicant]
JP H04173884A · 1992 [cited by applicant]
JP 2010528133A · 2010 [cited by applicant]
JP 2016515153A · 2016 [cited by applicant]
WO 2004108825 · 2004 [cited by applicant]
WO 2012035112A1 · 2012 [cited by applicant]
International Search Report issued in connection with International Application No. PCT/EP2020/054946 mailed Aug. 21, 2020. [cited by applicant]
“Basic characteristics of Aerosil? fumed silica Technical Bulletin Fine Particles 11”, Sep. 22, 2015 (Sep. 22, 2015), pp. 1-70, XP055215228, Retrieved from the Internet: URL: https://www.aerosil.com/sites/lists/IM / Doc… [cited by applicant]