Emulsion including polymers containing a 1,1-disubstituted alkene compound, adhesives, coatings, and methods thereof

Patent metadata

Field	Value
Publication number	US-10184073-B2
Application number	US-201715467597-A
Country	US
Kind code	B2
Filing date	Mar 23, 2017
Priority date	Sep 8, 2014
Publication date	Jan 22, 2019
Grant date	Jan 22, 2019

Abstract

The present teachings show that it is possible to polymerize 1,1-disubstituted alkene compounds in an emulsion (for example using a water based carrier liquid), despite the possible reactions between the monomer and water. Polymerization of 1,1-disubstituted alkene compounds in an emulsion provides opportunities to better control the polymerization compared with bulk polymerization. The emulsion polymerization techniques can be employed for preparing homopolymers, copolymers (e.g., random copolymers), and block copolymers.

First claim

What is claimed is:

1. An emulsion comprising:
i) 30 weight percent or more of a continuous phase including a carrier fluid including water;
ii) a dispersed phase including a polymer and having a surfactant layer in contact with the polymer and with the carrier fluid;
wherein the polymer is present in an amount of about 10 weight percent or more, includes one or more monomers including one or more 1,1-disubstituted alkene compounds, and has a number average molecular weight of about 700 g/mole or more, and wherein the polymer has a polydispersity index of about 1.7 or less.

2. The emulsion of claim 1 , wherein the polymer has a number average molecular weight of about 2,000 g/mole to about 1,000,000 g/mole.

3. The emulsion of claim 1 , wherein the dispersed phase includes micelles having a number average radius of about 0.10 μm to about 300 μm.

4. The emulsion of claim 3 , wherein the concentration of the polymer is about 20 weight percent or more.

5. The emulsion of claim 4 , wherein the carrier liquid consists essentially of water, and
i) the concentration of the carrier liquid is sufficiently high so that the emulsion is capable of flowing; or
ii) the ratio of the zero shear viscosity of the emulsion to the zero shear viscosity of the polymer at 25° C. is about 0.2 or less.

6. The emulsion of claim 5 , wherein the carrier liquid is present in an amount of about 65 weight percent or less, based on the total weight of the emulsion.

7. The emulsion of claim 6 , wherein the polymer is formed by a polymerization activated by one or more monomer activators including an ionic metal amide, an hydroxide, a cyanide, a phosphine, an alkoxide, an amine, an organometallic compound, or a metal benzoate; wherein the molar ratio of the one or more monomers to the monomer activators is greater than about 50:1.

8. The emulsion of claim 6 , wherein the one or more 1,1-disubstituted alkenes includes methyl propyl methylene malonate, dihexyl methylene malonate, di-isopropyl methylene malonate, butyl methyl methylene malonate, ethoxyethyl ethyl methylene malonate, methoxyethyl methyl methylene malonate, hexyl methyl methylene malonate, dipentyl methylene malonate, ethyl pentyl methylene malonate, methyl pentyl methylene malonate, ethyl ethylmethoxy methylene malonate, ethoxyethyl methyl methylene malonate, butyl ethyl methylene malonate, dibutyl methylene malonate, diethyl methylene malonate (DEMM), diethoxy ethyl methylene malonate, dimethyl methylene malonate, di-n-propyl methylene malonate, ethyl hexyl methylene malonate, methyl fenchyl methylene malonate, ethyl fenchyl methylene malonate, 2-phenylpropyl ethyl methylene malonate, 3-phenylpropyl ethyl methylene malonate, or dimethoxy ethyl methylene malonate.

9. The emulsion of claim 8 , wherein the polymer includes a first 1,1-disubstituted alkene and a second 1,1-disubstituted alkene.

10. An emulsion comprising:
i) 30 weight percent or more of a continuous phase including a carrier fluid including water, wherein the carrier liquid is present in an amount of about 65 weight percent or less, based on the total weight of the emulsion; and
ii) a dispersed phase including a polymer and having a surfactant layer in contact with the polymer and with the carrier fluid, wherein the dispersed phase includes micelles having a number average radius of about 0.10 μm to about 300 μm and wherein the concentration of the polymer is about 20 weight percent or more;
wherein the polymer is present in an amount of about 10 weight percent or more, includes one or more monomers including one or more 1,1-disubstituted alkene compounds, and has a number average molecular weight of about 700 g/mole or more;
wherein the one or more 1,1-disubstituted alkenes includes methyl propyl methylene malonate, dihexyl methylene malonate, di-isopropyl methylene malonate, butyl methyl methylene malonate, ethoxyethyl ethyl methylene malonate, methoxyethyl methyl methylene malonate, hexyl methyl methylene malonate, dipentyl methylene malonate, ethyl pentyl methylene malonate, methyl pentyl methylene malonate, ethyl ethylmethoxy methylene malonate, ethoxyethyl methyl methylene malonate, butyl ethyl methylene malonate, dibutyl methylene malonate, diethyl methylene malonate (DEMM), diethoxy ethyl methylene malonate, dimethyl methylene malonate, di-n-propyl methylene malonate, ethyl hexyl methylene malonate, methyl fenchyl methylene malonate, ethyl fenchyl methylene malonate, 2-phenylpropyl ethyl methylene malonate, 3-phenylpropyl ethyl methylene malonate, or dimethoxy ethyl methylene malonate wherein the polymer includes a first polymer block including about 10 weight percent or more of a first 1,1-disubstituted alkene; and a second polymer block including less than 10 weight percent of the first 1,1-disubstituted alkene.

11. The emulsion of claim 9 , wherein the polymer is a random copolymer including the 1,1-disubstituted alkene and a second monomer.

12. The emulsion of claim 6 , wherein the one or more monomers includes:
i) a first 1,1-disubstituted alkene including methyl propyl methylene malonate, dihexyl methylene malonate, di-isopropyl methylene malonate, butyl methyl methylene malonate, ethoxyethyl ethyl methylene malonate, methoxyethyl methyl methylene malonate, hexyl methyl methylene malonate, dipentyl methylene malonate, ethyl pentyl methylene malonate, methyl pentyl methylene malonate, ethyl ethylmethoxy methylene malonate, ethoxyethyl methyl methylene malonate, butyl ethyl methylene malonate, dibutyl methylene malonate, diethyl methylene malonate (DEMM), diethoxy ethyl methylene malonate, dimethyl methylene malonate, di-n-propyl methylene malonate, ethyl hexyl methylene malonate, methyl fenchyl methylene malonate, ethyl fenchyl methylene malonate, 2-phenylpropyl ethyl methylene malonate, 3-phenylpropyl ethyl methylene malonate, or dimethoxy ethyl methylene malonate; and
ii) a different 1,1-disubstituted alkene including methyl propyl methylene malonate, dihexyl methylene malonate, di-isopropyl methylene malonate, butyl methyl methylene malonate, ethoxyethyl ethyl methylene malonate, methoxyethyl methyl methylene malonate, hexyl methyl methylene malonate, dipentyl methylene malonate, ethyl pentyl methylene malonate, methyl pentyl methylene malonate, ethyl ethylmethoxy methylene malonate, ethoxyethyl methyl methylene malonate, butyl ethyl methylene malonate, dibutyl methylene malonate, diethyl methylene malonate (DEMM), diethoxy ethyl methylene malonate, dimethyl methylene malonate, di-N-propyl methylene malonate, ethyl hexyl methylene malonate, methyl fenchyl methylene malonate, ethyl fenchyl methylene malonate, 2 phenylpropyl ethyl methylene malonate, 3 phenylpropyl ethyl methylene malonate, or dimethoxy ethyl methylene malonate.

13. An emulsion comprising:
i) 30 weight percent or more of a continuous phase including a carrier fluid including water;
ii) a dispersed phase including a polymer and having a surfactant layer in contact with the polymer and with the carrier fluid;
wherein the polymer is present in an amount of about 10 weight percent or more, includes one or more monomers including one or more 1,1-disubstituted alkene compounds, and has a number average molecular weight of about 700 g/mole or more and, wherein the polymer includes a first polymer block including about 10 weight percent or more of a first 1,1-disubstituted alkene; and a second polymer block including less than 10 weight percent of the first 1,1-disubstituted alkene.

14. An emulsion comprising:
i) 30 weight percent or more of a continuous phase including a carrier fluid including water;
ii) a dispersed phase including a polymer and having a surfactant la

Assignees

• Sirrus Inc

Inventors

• Stevenson Peter Rulon
• Holzer Alexander R
• Palsule Aniruddha Sudhir
• Sullivan Jeffrey M

Classifications

• C08F22/10

  Esters · CPC title

• C08F122/14

  Esters having no free carboxylic acid groups · CPC title

• C08F267/06

  on to polymers of esters · CPC title

• C08F2/22

  Emulsion polymerisation · CPC title

• C09D135/02

  Homopolymers or copolymers of esters (C09D135/06, C09D135/08 take precedence) · CPC title