IP Library Granted Patent US 9,169,352
Granted Patent B2
US 9,169,352 · App. 14/626,745 · Granted Oct 27, 2015

Aromatic dicyanate compounds with high aliphatic carbon content

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 9,169,352
App. No.
14/626,745
Granted
Oct 27, 2015
Kind
B2
Abstract

Aromatic dicyanate compounds which comprise aliphatic moieties having at least about six carbon atoms and resins and thermoset products based on these compounds.

Claims (21)

1. A polymer or prepolymer of a dicyanate compound of formula (Ia):

wherein:

each m independently is 1 or 2;

the moieties R independently represent halogen, cyano, nitro, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkoxy, optionally substituted alkenyl, optionally substituted alkenyloxy, optionally substituted aryl having from 6 to about 10 carbon atoms, optionally substituted aralkyl having from 7 to about 12 carbon atoms, optionally substituted aryloxy having from 6 to about 10 carbon atoms, and optionally substituted aralkoxy having from 7 to about 12 carbon atoms and

n has a value of from about 7 to about 24;

and any non-aromatic cyclic moieties comprised in the above formula (Ia) may optionally carry one or more substituents and/or may optionally comprise one or more double bonds and/or may optionally be polycyclic.

2. A polymerizable mixture, wherein the mixture comprises at least one dicyanate compound of claim 1 and/or a prepolymer thereof, and one or more substances which are selected from polymerization catalysts, co-curing agents, flame retardants, synergists for flame retardants, solvents, fillers, glass fibers, adhesion promoters, wetting aids, dispersing aids, surface modifiers, thermoplastic polymers, and mold release agents.

3. A polymerizable mixture, wherein the mixture comprises at least one (i) dicyanate compound of claim 1 and/or a prepolymer thereof and (ii) at least one compound and/or a prepolymer thereof which is capable of reacting with (i).

4. The mixture of claim 3 , wherein the at least one compound (ii) is selected from compounds which comprise one or more polymerizable ethylenically unsaturated moieties, aromatic di- and polycyanates which are different from a dicyanate compound of formula (Ia), aromatic di- and polycyanamides, di- and polymaleimides, and di- and polyglycidyl ethers.

5. The mixture of claim 3 , wherein the mixture further comprises one or more substances which are selected from polymerization catalysts, co-curing agents, flame retardants, synergists for flame retardants, solvents, fillers, glass fibers, adhesion promoters, wetting aids, dispersing aids, surface modifiers, thermoplastic polymers, and mold release agents.

6. The mixture of claim 2 , wherein the mixture is partially or completely polymerized.

7. A product which comprises a polymerized mixture of claim 2 .

8. The product of claim 7 , wherein the product is at least one of an electrical laminate, an IC substrate, a casting, a coating, a die attach and mold compound formulation, a composite, and an adhesive.

9. A process for preparing the dicyanate compound of claim 1 , wherein the process comprises reacting a compound of formula (II):

wherein m, R a , R b and R are as set forth in claim 1 in a solvent with an at least about stoichiometric quantity of a cyanogen halide in the presence of an at least about stoichiometric quantity of a base.

10. The process of claim 9 , wherein the cyanogen halide comprises at least one of cyanogen chloride and cyanogen bromide.

11. The process of claim 9 , wherein the reaction is carried out at a temperature of from about −40° C. to about 60° C.

12. The process of claim 9 , wherein the base comprises one or more of sodium hydroxide, potassium hydroxide, trimethylamine, and triethylamine.

13. The process of claim 9 , wherein the base comprises triethylamine.

14. The process of claim 9 , wherein the solvent comprises one or more of water, an aliphatic ketone, a chlorinated hydrocarbon, an aliphatic or cycloaliphatic ether or diether, and an aromatic hydrocarbon.

15. The process of claim 9 , wherein the solvent comprises one or more of acetone, methylethylketone, methylene chloride, and chloroform.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 29, 2015
From: DOW GLOBAL TECHNOLOGIES LLC
To: BLUE CUBE IP LLC
Reel/Frame 035926/0739 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 5, 2015
From: MULLINS, MICHAEL J.; HEFNER, ROBERT E., JR.; WILSON, MARK B.
To: DOW GLOBAL TECHNOLOGIES INC.
Reel/Frame 035792/0120 →
CHANGE OF NAME Recorded Jun 5, 2015
From: DOW GLOBAL TECHNOLOGIES INC.
To: DOW GLOBAL TECHNOLOGIES LLC
Reel/Frame 035832/0610 →