IP Library Granted Patent US 9,523,019
Granted Patent B2
US 9,523,019 · App. 14/533,129 · Granted Dec 20, 2016

Method and formulations for the manufacture of coated articles and composites

Inventors: Carl Fredrik Carlborg (Stockholm, SE); Tommy Haraldsson (Järfälla, SE)
Assignee: Mercene Labs AB
C09D163/04B05D3/06B05D7/58C08F283/105C08G59/4064C09D4/00C09D163/00H05K3/0091C08F222/1006G03F7/0275G03F7/038Y10T428/24851Y10T428/269Y10T428/31515Y10T428/31522
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 9,523,019
App. No.
14/533,129
Granted
Dec 20, 2016
Kind
B2
Abstract

An object with a coating comprising: a) covalent bonds formed by reaction of a thiol group and a carbon-carbon double bond, b) covalent bonds formed by reaction of a thiol group and epoxide group, c) covalent bonds formed by a reaction of a carbon-carbon double bond and an epoxide group, said coating comprising a first primer coating and a second coating, said coating comprising covalent bonds between said first and second coatings, said first primer coating comprising covalent cross links between compounds, in the first coating the fraction (r3=ta/tc) of unreacted thiol groups (ta) to thiol groups which have reacted to form a covalent bond (tc) does not exceed 0.11, wherein the half height peak width of tan delta does not exceed 30° C. Advantages of the dual cure composition is that excellent strength is obtained and that the second curing is slow compared to the first initial curing.

Claims (19)

1. A coated object comprising a coating which is at least partially applied to said object, said coating comprising:

a) covalent bonds formed by reaction of a thiol group and a carbon-carbon double bond,

b) covalent bonds formed by reaction of a thiol group and epoxide group,

c) covalent bonds formed by a reaction of a carbon-carbon double bond and an epoxide group,

said coating comprising a first coating and a second coating,

said coating comprising covalent bonds between said first and second coatings,

said first coating comprising covalent cross links between compounds,

in the first coating the fraction (r 3 =ta/tc) of unreacted thiol groups (ta) to thiol groups which have reacted to form a covalent bond (tc) does not exceed 0.11,

wherein, for the first coating the half height peak width of tan delta does not exceed 30° C., said tan delta peak temperature (Tp) and said half height peak width being obtained from a viscoelasticity (tan delta) temperature distribution curve which is determined using a viscoelastic spectrometer at a frequency of 1 Hz, an initial strain of 1%, an amplitude of 15 μm and a temperature elevating rate of 5° C./min, temperatures being equal to and greater than Tp to the temperature defined by the point of intersection of the line of tan delta=1/2P, wherein P is the peak value of tan δ, with the distribution curve.

2. The coated object according to claim 1 , wherein said second coating comprises at least one compound comprising at least one chemical group selected from the group consisting of a hydroxyl group, an amine group, a thiol group, an anhydride group, a cyanoacrylate group, an epoxide group, and a metal oxide.

3. The coated object according to claim 1 , wherein said second coating comprises at least one compound comprising a chemical group selected from the group consisting of an acrylate, a methacrylate, a thiol, an isocyanate, a maleate, a fumarate, a vinyl ether, an alkene, an alkyne, an allyl ether.

4. The coated object according to claim 1 , wherein said second coating comprises at least one selected from the group consisting of a metal, a polymer sheet, and a powder.

5. The coated object according to claim 1 , wherein the surface of said object comprises at least one selected from the group consisting of a metal, a rubber, silicon, a thermoplastic elastomer, cellulose fibers, a textile, wood, a composite material, concrete, and stone.

6. The coated object according to claim 1 , wherein the object to be at least partially coated is a printed circuit board.

7. The coated object according to claim 1 , wherein the first coating comprises at least one compound selected from the group consisting of pentaerythritol tetrakis (2-mercaptoacetate), pentaerythritol tetramercaptopropionate (PETMP); 1-octanethiol; butyl 3-mercaptopropionate; 2,4,6-trioxo-1,3,5-triazina-triy (triethyl-tris (3-mercapto propionate); 1,6-Hexanedithiol; 2,5-dimercaptomethyl-1,4-dithiane, pentaerythritol tetramercaptoacetate, trimethylolpropane trimercaptoacetate, 2,3-dimercapto-1-propanol, 2,3-(dimercaptoethylthio)-1-mercaptopropane, 1,2,3-trimercaptopropane, toluenedithiol, xylylenedithiol, 1,8-octanedithiol, and trimethylolpropane tris(3-mercaptopropionate), and glycol dimercaptopropionate and pentaerythritol tetramercaptopropionate (PETMP), wherein at least one thiol group has formed a covalent bond with at least one selected from a carbon-carbon double bond and an epoxide group.

8. The coated object according to claim 1 , wherein the first coating comprises at least one compound selected from the group consisting of triallyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione; triethyleneglycol divinyl ether (TEGDVE); trimethylolpropane diallyl ether; 1,6-heptadiyne; 1,7-octadiyne; bis-2,2-[4-(2-[norborn-2-ene-5-carboxylate]ethoxy)phenyl]propane (BPAEDN); 1,6-hexanediol di-(endo,exo-norborn-2-ene-5-carboxylate) (HDDN); trimethylolpropane tri-(norborn-2-ene-5-carboxylate) (TMPTN); pentaerythritoltri-(norborn-2-ene-5-carboxylate) (PTN3); pentaerythritol tetra-(norborn-2-ene-5-carboxylate) (PTN4); tricyclodecane dimethanol di-(endo, exo-norborn-2-ene-5-carboxylate) (TCDMDN); and di(trimethylolpropane) tetra-(norbom-2-ene-5-carboxylate) (DTMPTN), wherein at least one carbon-carbon double bond has formed a covalent bond with at least one selected from a thiol group and an epoxide group.

9. The coated object according to claim 1 , wherein the first coating comprises at least one compound selected from the group consisting of Tris(2,3-epoxidepropyl) isocyanurate, trimethylolpropane triglycidyl ether, tris(4-hydroxyphenyl)methane triglycidyl ether, poly(ethylene glycol) diglycidyl ether, bisphenol A diglycidyl ether 1,2,5,6-diepoxidecyclooctane, 1,2,7,8-diepoxideoctane, 1,2-Epoxide-5-hexene, 1,4-cyclohexanedimethanol diglycidyl ether, 3,4-epoxidecyclohexylmethyl 3,4-epoxidecyclohexanecarboxylate, 4,4′-meth-ylenebis(N,N-diglycidylaniline), bis[4-(glycidyloxy)phenyl]methane, bis[4-(glycidyloxy)phenyl]methane, diglycidyl 1,2-cyclohexanedicarboxylate, N,N-diglycidyl-4-glycidyloxyaniline, neopentyl glycol diglycidyl ether, resorcinol diglycidyl ether, and tris(4-hydroxyphenyl)methane triglycidyl ether, wherein at least one epoxide group has formed a covalent bond with at least one selected from a thiol group and a carbon-carbon double bond.

10. The coated object according to claim 1 , wherein the thickness of the coating is in the interval 0.01-2000 μm.

11. The coated object according to claim 1 , wherein the coating forms a barrier impermeable to liquid.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 8, 2016
From: HARALDSSON, TOMMY; CARLBORG, CARL FREDRIK
To: MERCENE LABS AB
Reel/Frame 040249/0491 →
Priority Claims (1)
SE 1200269 · May 7, 2012 · national
Continuity (2)
Continuation PCTEP2013059462 · May 7, 2013
Related Publication 20150118456A1 · Apr 30, 2015