Encapsulated polymerization initiators, polymerization systems and methods using the same

• US 9,683,147 B2
• Filed: 04/08/2016
• Issued: 06/20/2017
• Est. Priority Date: 05/29/2015
• Status: Active Grant

• Current Assignee: Sirrus, Inc (Nippon Shokubai Company Limited)
• Original Assignee: Sirrus, Inc (Nippon Shokubai Company Limited)
• Inventors: Stevenson, Peter Rulon, Palsule, Aniruddha Sudhir, Sullivan, Jeffrey M.
• Primary Examiner(s): NGUYEN, VU ANH
• Application Number:
  US15/094,705
• Publication Number:
  US 20160347976A1
• Time in Patent Office: 438 Days
• Field of Search: None
• CPC Class Codes: B01J 13/185 in an organic phase
• CPC Class Codes: C08F 222/14 Esters having no free carboxylic acid groups , e.g. dialkyl maleates or fumarates
• CPC Class Codes: C08J 3/241 Preventing premature crosslinking by physical separation of components, e.g. encapsulation
• CPC Class Codes: C08K 3/01 characterized by their specific function
• CPC Class Codes: C08K 5/0008 Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
• CPC Class Codes: C08K 5/11 of acyclic polycarboxylic acids
• CPC Class Codes: C08K 9/10 Encapsulated ingredients
• CPC Class Codes: C08L 27/06 Homopolymers or copolymers of vinyl chloride
• CPC Class Codes: C09J 135/02 Homopolymers or copolymers of esters C09J135/06, C09J135/08 take precedence
• CPC Class Codes: C09J 4/06 Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00

Abstract

A polymerizable system includes a curable composition and one or more encapsulated initiator particles. The curable composition can include one or more 1,1-disubstituted alkene compounds and the encapsulated initiator particles can include one or more polymerization initiators encapsulated by a cured composition. The cured composition includes one or more 1,1-disubstituted alkene compounds.

Claims

1. A polymerizable system comprising:

a curable composition comprising one or more 1,1-disubstituted alkene compounds; and

one or more encapsulated initiator particles, each of the one or more encapsulated initiator particles comprising;

one or more polymerization initiators substantially encapsulated by a cured composition comprising one or more 1,1-disubstituted alkene compounds;

wherein each polymerization initiator is capable of initiating polymerization of the curable composition, and wherein the one or more polymerization initiators comprise spherical, non-spherical, irregular, angular, textured or layered particles having an average granulometry of about 0.1 microns to about 1,000 microns.

2. The polymerizable system of claim 1, wherein the one or more encapsulated initiator particles are dispersed in the curable composition.

3. The polymerizable system of claim 1, wherein the one or more 1,1-disubstituted alkene compounds of the curable composition and the one or more 1,1-disubstituted alkene compounds of the cured composition are each selected from the group consisting of methylene malonates, methylene β

-ketoesters, methylene β

-diketones, dialkyl disubstituted vinyls, dihaloalkyl disubstituted vinyls, monofunctional, difunctional or multifunctional monomers, oligomers, or polymers thereof, and combinations thereof.

4. The polymerizable system of claim 1, wherein the one or more 1,1-disubstituted alkene compounds of the curable composition and the one or more 1,1-disubstituted alkene compounds of the cured composition are different.

5. The polymerizable system of claim 1 further comprises one or more of a plasticizer, a stabilizer, a thickening agent, and a thixotropic agent.

6. The polymerizable system of claim 1 has a viscosity of about 1 cPs to about 30,000 cPs.

7. The polymerizable system of claim 1 can be applied to a substrate and initiate polymerization of the curable composition when one or more of said encapsulated initiator particles is ruptured.

8. The polymerization system of claim 7, wherein said encapsulated initiator particles can be ruptured through about 5 psi of mechanical force applied to the polymerizable system.

9. The polymerizable system of claim 1 is an adhesive composition or a threadlocking composition and wherein the system has a set time of about 1 hour or less and a cure time of about 4 hours or less.

10. The polymerizable system of claim 1 has a shelf life of about 20 weeks or more at ambient conditions.

11. The polymerizable system of claim 1, wherein the ratio of the cured composition to the one or more polymerization initiators is a ratio of about 1:

1 to about 2;

1, by weight.

12. The polymerizable system of claim 1, wherein the one or more polymerization initiators comprise one or more alkali metal salts, alkaline earth metal salts, ammonium salts, amine salts, halides, or metal oxides.

13. The polymerizable system of claim 1, wherein the encapsulated initiator particles are mononuclear or polynuclear encapsulated initiator particles.

14. The polymerizable system of claim 1, wherein the encapsulated initiator particles further comprise a shell layer surrounding and encapsulating the encapsulated initiator particles.

15. A polymerizable system comprising:

a curable composition comprising one or more 1,1-disubstituted alkene compounds; and

one or more encapsulated initiator particles comprising;

an initiator matrix comprising;

a first cured composition comprising one or more 1,1-disubstituted alkene compounds; and

one or more polymerization initiators substantially encapsulated by the first cured composition;

wherein the one or more polymerization initiators are capable of initiating polymerization of the curable composition, and wherein the ratio of the cured composition to the one or more polymerization initiators is a ratio of about 1;

1 to about 2;

1 by weight.

16. The polymerizable system of claim 15, wherein the encapsulated initiator particle further comprises a shell layer, wherein the shell layer surrounds and encapsulates the initiator matrix.

17. The polymerizable system of claim 16, wherein the shell layer is formed of one or more of a second cured composition formed of one or more 1,1-disubstituted alkene compounds;

a urea formaldehyde resin;

a polyvinyl alcohol;

a gelatin;

an acrylate; and

a cured oligomeric reactive monomer.

18. The polymerizable system of claim 15, wherein the one or more polymerization initiators comprise spherical, non-spherical, irregular, angular, textured, or layered particles having an average granulometry of about 0.1 microns to about 1,000 microns.