Electroinitiated polymerization of compositions having a 1,1-disubstituted alkene compound

• US 9,617,354 B2
• Filed: 11/23/2015
• Issued: 04/11/2017
• Est. Priority Date: 06/01/2015
• Status: Active Grant

• Current Assignee: Sirrus, Inc (Nippon Shokubai Company Limited)
• Original Assignee: Sirrus, Inc (Nippon Shokubai Company Limited)
• Inventors: Stevenson, Peter Rulon, Sullivan, Jeffrey M.
• Primary Examiner(s): CHEUNG, WILLIAM K
• Application Number:
  US14/948,734
• Publication Number:
  US 20160347871A1
• Time in Patent Office: 505 Days
• Field of Search: 526236, 526319, 525 10
• CPC Class Codes: C08F 2/58 Polymerisation initiated by direct application of electric current electrolytic processes, e.g. electrophoresis C25
• CPC Class Codes: C08F 20/16 of phenols or of alcohols containing two or more carbon atoms
• CPC Class Codes: C08K 3/36 Silica
• CPC Class Codes: C08L 2201/10 Transparent films; Clear coatings; Transparent materials
• CPC Class Codes: C08L 35/02 Homopolymers or copolymers of esters C08L35/06, C08L35/08 take precedence
• CPC Class Codes: C09J 4/00 Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
• CPC Class Codes: C25B 3/29 Coupling reactions

Abstract

Electropolymerizable compositions are disclosed. Certain electropolymerizable compositions include one or more 1,1-disubstituted alkene compounds and one or more conductive synergists. Other certain electropolymerizable compositions include one or more 1,1-disubstituted alkene compounds and one or more acid stabilizers and one or more free radical stabilizers.

Claims

1. An electropolymerizable composition comprising:

one or more 1,1-disubstituted alkene compounds;

one or more acid stabilizers;

one or more free radical stabilizers; and

about 1% to about 2% of one or more conductive synergists, the one or more conductive synergists selected from the group including a metal, a conductive inorganic material, a conductive polymer, an organic material, a metalloid material, a composite material, and an ionic compound; and

wherein the one or more acid stabilizers and the one or more free radical stabilizers are included in a ratio of about 10;

100 parts-per million (“

ppm”

) to a ratio of about 10;

1,000 ppm or more.

2. The electropolymerizable composition of claim 1, wherein the one or more 1,1-disubstituted alkene compounds comprise one or more of methylene malonate, methylene β

-ketoester, methylene β

-diketone, dialkyl disubstituted vinyl, dihaloalkyl disubstituted vinyl, and monofunctional, difunctional, and multifunctional monomers, oligomers, and polymers thereof.

3. The electropolymerizable composition of claim 1, wherein the one more 1,1-disubstituted alkene compounds comprise one or more of diethyl methylene malonate, fenchyl methyl methylene malonate, methylmethoxy ethyl methylene malonate, hexyl methyl methylene malonate, and dibutyl methylene malonate.

4. The electropolymerizable composition of claim 1, further comprising one or more members from the group including dyes, pigments, toughening agents, impact modifiers, rheology modifiers, plasticizing agents, natural or synthetic rubbers, filler agents, reinforcing agents, thickening agents, opacifiers, inhibitors, fluorescence markers, thermal degradation reducers, thermal resistance conferring agents, surfactants, and wetting agents.

5. The electropolymerizable composition of claim 4, wherein the thickening agents and plasticizers comprise one or more of vinyl chloride terpolymer and dimethyl sebacate.

6. The electropolymerizable composition of claim 4, wherein the filler agents comprise fumed silica.

7. The electropolymerizable composition of claim 1 is substantially transparent.

8. The electropolymerizable composition of claim 1 is substantially free of a solvent.

9. The electropolymerizable composition of claim 1 has a viscosity of about 1,500 cPs to about 2,500 cPs.

10. The electropolymerizable composition of claim 1 is configured to cure when exposed to an electrical charge.

11. An electropolymerizable composition comprising:

one or more 1,1-disubstituted alkene compounds; and

about 1% to about 2% of one or more conductive synergists, the one or more conductive synergists selected from the group including a metal, a conductive inorganic material, a conductive polymer, an organic material, a metalloid material, a composite material, and an ionic compound.

12. The electropolymerizable composition of claim 11, wherein the one or more 1,1-disubstituted alkene compounds comprise one or more of diethyl methylene malonate, fenchyl methyl methylene malonate, methylmethoxy ethyl methylene malonate, hexyl methyl methylene malonate, and dibutyl methylene malonate.

13. The electropolymerizable composition of claim 11, wherein the conductive synergist comprises one or more of carbon black, tetrabutylammonium bromide, graphite, graphene, silver, ammonium trifluoromethane sulfonate, and ammonium sulfonate.

14. The electropolymerizable composition of claim 11, wherein the conductive synergist comprises carbon black.

15. The electropolymerizable composition of claim 11, further comprising one or more acid stabilizers and one or more free radical stabilizers, and wherein the one or more acid stabilizers and the one or more free radical stabilizers are included in a ratio of about 10:

100 parts-per million (“

ppm”

) to a ratio of about 10;

1,000 ppm.

16. An electropolymerizable composition comprising:

diethyl methylene malonate;

carbon black;

ammonium trifluoromethanesulfonate;

vinyl chloride terpolymer;

fumed silica;

methanesulfonic acid (“

MSA”

); and

mono methyl ether of hydroquinone (“

MeHQ”

).

17. The electropolymerizable composition of claim 16 comprises by weight:

about 83.399% diethyl methylene malonate;

about 2.000% carbon black;

about 1.000% ammonium trifluoromethanesulfonate;

about 13.000% vinyl chloride terpolymer;

about 0.5000% fumed silica;

about 0.001% MSA; and

about 0.100% MeHQ.

18. The electropolymerizable composition of claim 16 has a viscosity of about 1,500 cPs to about 2,500 cPs.

19. The electropolymerizable composition of claim 16 exhibits a substantially black appearance.