IP Library Granted Patent US 10,550,280
Granted Patent B2
US 10,550,280 · App. 15/319,127 · Granted Feb 4, 2020

Hollow particles, method for producing same, use thereof, and method for producing microcapsule particles

Inventors: Yugo Katayama (Nara, JP); Kengo Nishiumi (Nara, JP); Ayumi Kiyohara (Nara, JP); Shuichi Sasahara (Nara, JP); Haruhiko Matsuura (Nara, JP); Junko Kubo (Nara, JP)
Assignee: SEKISUI PLASTICS CO., LTD.
C09D133/14B01J13/18C08F220/32C09D5/006C09D7/67C09D7/68C09D7/70C09K5/14G02B1/11G02B5/0242G02B5/0247C08F2220/325C08F2500/24C08F2500/26C08F2800/20C08F2810/20
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Quick Facts
Patent No.
US 10,550,280
App. No.
15/319,127
Granted
Feb 4, 2020
Kind
B2
Abstract

Provided are hollow particles each having a shell including at least one layer, wherein the hollow particles have an average particle diameter of 10 to 200 nm and the at least one layer contains a vinyl-based resin.

Claims (44)

1. Hollow particles each having a shell including at least one layer, wherein

said hollow particles have an average particle diameter of 10 to 200 nm, and

said at least one layer contains a vinyl-based resin

wherein said vinyl-based resin comprises a crosslinked copolymer derived from a copolymer and a component derived from a crosslinking agent being a polyamine-based compound, wherein the copolymer is derived from at least one radical reactive vinyl monomer having an epoxy group or an oxetane group, and at least one radical reactive vinyl monomer having a silyl group.

2. The hollow particles according to claim 1 , wherein said hollow particles exhibit a 5% degradation initiation temperature of from 250 to 350° C.

3. The hollow particles according to claim 1 , wherein said radical reactive vinyl monomer having an epoxy group or an oxetane group is p-glycidylstyrene, glycidyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate glycidyl ether, (3-ethyloxetan-3-yl)methyl (meth)acrylate, or 3,4-epoxycyclohexylmethyl (meth)acrylate.

4. The hollow particles according to claim 1 , wherein said radical reactive vinyl monomer having a silyl group is vinyltrichlorosilane, vinyltrimethoxysilane, vinyltriethoxysilane, p-styrylmethoxysilane, 3-methacryloxypropyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropyltriethoxysilane, or 3-acryloxypropyltrimethoxysilane.

5. The hollow particles according to claim 1 , wherein

said hollow particles are hollow particles each having a shell including at least one layer,

said hollow particles have an average particle diameter of 10 to 150 nm and a gel fraction of 95% or more,

a BET specific surface area S B of said hollow particles and a theoretical specific surface area S T which is calculated from an average particle diameter and a hollow rate satisfy the following equation:

0.5≤ S B /S T ≤2.5.

6. The hollow particles according to claim 5 , wherein said hollow particles have a hollow rate of 5 to 90%.

7. A dispersion comprising the hollow particles according to claim 1 .

8. A coating agent comprising the hollow particles according to claim 1 .

9. An antireflection film comprising the hollow particles according to claim 1 .

10. A light extraction film comprising the hollow particles according to claim 1 .

11. A heat insulating film comprising the hollow particles according to claim 1 .

12. A heat conductivity adjusting agent in the form of hollow particles each having a shell comprising at least one layer, wherein

said hollow particles have an average particle diameter of 10 to 150 nm and a gel fraction of 95% or more, and

said at least one layer contains a vinyl-based resin,

wherein said vinyl-based resin comprises a crosslinked copolymer derived from a copolymer and a component derived from a crosslinking agent being a polyamine-based compound, wherein the copolymer is derived from at least one radical reactive vinyl monomer having an epoxy group or an oxetane group, and at least one radical reactive vinyl monomer having a silyl group.

13. The heat adjusting agent according to claim 12 having a 5% degradation initiation temperature of from 250 to 350° C.

14. A method for producing the hollow particles according to claim 1 , comprising:

(a) vinyl-based polymerizing:

i) the at least one radical reactive vinyl monomer having epoxy group or an oxetane group, and

ii) the at least one radical reactive vinyl monomer having a silyl group,

in a dispersing medium, in the presence of a non-reactive solvent incompatible with said dispersing medium, and

(b) crosslinking with the polyamine-based compound to produce the hollow particles; or

(c) vinyl-based polymerizing:

i) the at least one radical reactive vinyl monomer having an epoxy group or an oxetane group, and

ii) the at least one radical reactive vinyl monomer having a silyl group,

in the absence of said non-reactive solvent, and

absorbing said non-reactive solvent, thereby, preparing polymer particles containing said non-reactive solvent, and

(d) crosslinking with the polyamine-based compound, thereby phase-separating said non-reactive solvent from said polymer particles containing said non-reactive solvent to produce the hollow particles.

15. The method according to claim 14 , wherein:

the at least one radical reactive vinyl monomer having an epoxy group or an oxetane group comprises a vinyl group, a (meth)acryloyl group, an allyl group, a maleoyl group, a fumaroyl group, a styryl group, or a cinnamoyl group, and

the at least one radical reactive vinyl monomer having a silyl group comprises a vinyl group, a (meth)acryloyl group, an allyl group, a maleoyl group, a fumaroyl group, a styryl group, or a cinnamoyl group.

16. The method according to claim 14 , wherein

the radical reactive vinyl monomer having an epoxy group or an oxetane group is p-glycidylstyrene, glycidyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate glycidyl ether, or 3,4-epoxycyclohexylmethyl (meth)acrylate; and

the radical reactive vinyl monomer having a silyl group is vinyltrichlorosilane, vinyltrimethoxysilane, vinyltriethoxysilane, p-styrylmethoxysilane, 3-methacryloxypropyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropyltriethoxysilane, or 3-acryloxypropyltrimethoxysilane;

said dispersing medium is selected from water, ethanol, methanol, isopropyl alcohol, butane, pentane, hexane, cyclohexane, heptane, decane, hexadecane, toluene, xylene, ethyl acetate, butyl acetate, methyl ethyl ketone, methyl isobutyl ketone, methyl chloride, methylene chloride, chloroform, and carbon tetrachloride; and

said non-reactive solvent is a solvent incompatible with said dispersing medium, and is selected from butane, pentane, hexane, cyclohexane, heptane, decane, hexadecane, toluene, xylene, ethyl acetate, butyl acetate, methyl ethyl ketone, methyl isobutyl ketone, 1,4-dioxane, methyl chloride, methylene chloride, chloroform, and carbon tetrachloride.

17. The method according to claim 14 further comprising removing a non-reactive solvent encapsulated in the hollow particles.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 15, 2016
From: KATAYAMA, YUGO; NISHIUMI, KENGO; KIYOHARA, AYUMI; SASAHARA, SHUICHI; MATSUURA, HARUHIKO; KUBO, JUNKO
To: SEKISUI PLASTICS CO., LTD.
Reel/Frame 040990/0236 →
Priority Claims (5)
JP 2015-002463 · Jan 8, 2015 · national
JP 2015-054828 · Mar 18, 2015 · national
JP 2015-188269 · Sep 25, 2015 · national
JP 2015-191354 · Sep 29, 2015 · national
JP 2015-228797 · Nov 24, 2015 · national
Continuity (1)
Related Publication 20170114243A1 · Apr 27, 2017
Cited By (1)
US 12,528,934