EMULSION OF NITROGEN ATOM-CONTAINING POLYMER OR SALT THEREOF, PRODUCTION METHOD THEREFOR, AND PRODUCTION METHOD FOR PARTICLES

• US 20190315932A1
• Filed: 06/27/2019
• Published: 10/17/2019
• Est. Priority Date: 12/28/2016
• Status: Active Grant

• Current Assignee: Fujifilm Corporation (Fujifilm Holdings Corporation)
• Original Assignee: Fujifilm Corporation (Fujifilm Holdings Corporation)
• Inventors: TOKUOKA, Shinsuke, YOSHIDA, Hayato, SHIMONO, Katsuhiro, ITO, Takayuki
• Granted Patent: US 11,186,685 B2
• Time in Patent Office: Days
• CPC Class Codes: B29B 2009/125 Micropellets, microgranules, microparticles
• CPC Class Codes: B29B 2009/166 Deforming granules to give a special form, e.g. spheroidizing, rounding
• CPC Class Codes: B29B 9/12 characterised by structure or composition
• CPC Class Codes: C08J 2339/00 Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Derivatives of such polymers
• CPC Class Codes: C08J 2339/02 Homopolymers or copolymers of vinylamine
• CPC Class Codes: C08J 2379/00 Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
• CPC Class Codes: C08J 3/07 from polymer solutions
• CPC Class Codes: C08J 3/092 Hydrocarbons
• CPC Class Codes: C08J 3/095 Oxygen containing compounds
• CPC Class Codes: C08J 3/098 Other compounds
• CPC Class Codes: C08J 3/24 Crosslinking, e.g. vulcanising, of macromolecules mechanical aspects B29C35/00; crosslinking agents C08K
• CPC Class Codes: C08K 5/0025 Crosslinking or vulcanising agents; including accelerators
• CPC Class Codes: C08L 1/26 Cellulose ethers

Abstract

Provided are an emulsion of a nitrogen atom-containing polymer or a salt thereof, the emulsion having high emulsion stability and having a low dispersity of the particle diameter of emulsified particles, and a method for producing the emulsion. Also provided is a method for producing particles including a crosslinked nitrogen atom-containing polymer or a salt thereof by using the emulsion described above. Disclosed is a method for producing an emulsion of a nitrogen atom-containing polymer or a salt thereof, the method including a step of mixing a first solution that includes a nitrogen atom-containing polymer or a salt thereof and a hydrophilic solvent and has a viscosity of 10 to 2,000 mPa·s, and a second solution that includes a hydrophobic solvent and has a viscosity of 1 to 100 mPa·s, stirring the mixture, and thus obtaining an emulsion of the nitrogen atom-containing polymer or a salt thereof, wherein a ratio between the viscosity of the first solution and the viscosity of the second solution is in a range of 0.1:1 to 300:1.

Claims

1. A method for producing an emulsion of a nitrogen atom-containing polymer or a salt thereof, the method comprising:

a step of mixing a first solution that includes a nitrogen atom-containing polymer or a salt thereof and a hydrophilic solvent and has a viscosity of 10 to 2,000 mPa·

s, and a second solution that includes a hydrophobic solvent and has a viscosity of 1 to 100 mPa·

s, stirring the mixture, and thus obtaining an emulsion of the nitrogen atom-containing polymer or a salt thereof,

wherein a ratio between the viscosity of the first solution and the viscosity of the second solution is in a range of 0.1;

1 to 300;

1.

2. The method according to claim 1, wherein the viscosity of the first solution is 10 to 1,500 mPa·

s.

3. The method according to claim 1, wherein the ratio between the viscosity of the first solution and the viscosity of the second solution is in a range of 0.2:

1 to 100;

1.

4. The method according to claim 1, wherein an amine value of the nitrogen atom-containing polymer or a salt thereof is 10 mmol/g or more.

5. The method according to claim 1, wherein the nitrogen atom-containing polymer is at least one selected from the group consisting of polyallylamine, a polyalkyleneimine, and polyvinylamine.

6. The method according to claim 1, wherein the nitrogen atom-containing polymer includes polyallylamine.

7. The method according to claim 1, wherein the second solution includes an emulsifier having a weight-average molecular weight or a number-average molecular weight of 2,000 or more.

8. The method according to claim 7, wherein the emulsifier includes a sugar.

9. The method according to claim 7, wherein the emulsifier includes cellulose ether.

10. The method according to claim 1, wherein the hydrophobic solvent is at least one selected from the group consisting of an aromatic hydrocarbon-based solvent, an ester-based solvent, and olive oil.

11. The method according to claim 1, wherein an average particle diameter of emulsified particles of the emulsion of a nitrogen atom-containing polymer or a salt thereof is 1 to 200 μ

m.

12. An emulsion, comprising:

spherical objects formed from a first solution including a nitrogen atom-containing polymer or a salt thereof and a hydrophilic solvent and having a viscosity of 10 to 2,000 mPa·

s; and

a dispersing medium including a second solution including a hydrophobic solvent and having a viscosity of 1 to 100 mPa·

s,

wherein a ratio between the viscosity of the first solution and the viscosity of the second solution is in a range of 0.1;

1 to 300;

1.

13. A method for producing particles containing a crosslinked nitrogen atom-containing polymer or a salt thereof, the method comprising:

a step of mixing a first solution that includes a nitrogen atom-containing polymer or a salt thereof and a hydrophilic solvent and has a viscosity of 10 to 2,000 mPa·

s, and a second solution that includes a hydrophobic solvent and has a viscosity of 1 to 100 mPa·

s, stirring the mixture, and thus obtaining an emulsion of the nitrogen atom-containing polymer or a salt thereof; and

a step of adding a crosslinking agent to the emulsion in which the nitrogen atom-containing polymer or a salt thereof is emulsified, and performing a crosslinking reaction,

wherein a ratio between the viscosity of the first solution and the viscosity of the second solution is in a range of 0.1;

1 to 300;

1.

14. The method for producing particles according to claim 13, wherein the nitrogen atom-containing polymer is a crosslinked polymer having a substituent containing an NR^A1R^A2 structure:

in Formula, R^A1 and R^A2 each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aminoalkyl group having 1 to 20 carbon atoms or a salt thereof, an alkylaminoalkyl group having 2 to 20 carbon atoms or a salt thereof, a dialkylaminoalkyl group having 3 to 20 carbon atoms or a salt thereof, a trialkylammoniumalkyl group having 4 to 20 carbon atoms, an alkylcarbonyl group having 1 to 20 carbon atoms, a carboxyalkyl group having 1 to 20 carbon atoms, or a hydroxyalkyl group having 1 to 20 carbon atoms.

15. The method for producing particles according to claim 13, wherein the particles have an average particle diameter of 20 to 150 μ

m and a swelling rate of 9 to 16 ml/g, provided that the average particle diameter is determined by converting areas of 1,000 or more particle images of optical microscopic photographs into diameters, and calculating the average particle diameter as the volume average particle diameter using those diameters, and the swelling rate is determined by swelling particles by repeating shaking and standing for one hour or longer in an aqueous solution at pH 6.3 of 2.2% by mass of sodium 2-morpholinoethanesulfonate and 0.5% by mass of sodium chloride at 20°

C. twenty or more times, and calculating the swelling rate by dividing the particle volume after swelling by the particle mass before swelling.

16. The method for producing particles according to claim 13, wherein each of the particles has an outer shell portion and a central portion having a lower degree of crosslinking than the outer shell portion.