Aqueous dispersion of microcapsules, and uses thereof

Patent metadata

Field	Value
Publication number	US-12023640-B2
Application number	US-202217826481-A
Country	US
Kind code	B2
Filing date	May 27, 2022
Priority date	May 27, 2021
Publication date	Jul 2, 2024
Grant date	Jul 2, 2024

Abstract

The invention relates to an aqueous dispersion of microcapsules, said microcapsules comprising a hydrophobic core and a polymeric shell wherein said polymeric shell is formed of the reaction product of (i) at least one monofunctional or multifunctional α,β-unsaturated carbonyl compound, and (ii) at least one nanocellulose or microcrystalline cellulose. The invention also relates to a process for the manufacture of such an aqueous dispersion, as well as consumer products containing an aqueous dispersion of microcapsules according to the invention.

First claim

The invention claimed is:

1. An aqueous dispersion of microcapsules, said microcapsules comprising a hydrophobic core and a polymeric shell wherein said polymeric shell is formed of the reaction product of:
(i) at least one multifunctional α,β-unsaturated carbonyl compound,
(ii) at least one nanocellulose or microcrystalline cellulose,
(iii) optionally, at least one monoethylenically α,β-unsaturated carbonyl compound and/or poly(alkylene itaconate),
(iv) optionally, at least one monofunctional and/or multifunctional thiol compound, and
(v) optionally, at least one silyl (meth)acrylate compound, and
wherein the weight ratio between the multifunctional α,β-unsaturated carbonyl compound(s) (i) and the nanocellulose or microcrystalline cellulose (ii) is lower or equal to 1.

2. The aqueous dispersion of claim 1 , wherein the at least one multifunctional α,β-unsaturated carbonyl compound (i) is selected from the group consisting of a multifunctional (meth)acrylate compound, an anhydride and a multifunctional (meth)acrylamide compound.

3. The aqueous dispersion of claim 2 , wherein the at least one multifunctional α,β-unsaturated carbonyl compound (i) is a multifunctional (meth)acrylate compound.

4. The aqueous dispersion of claim 3 , wherein the multifunctional (meth)acrylate compound is an ester of (meth)acrylic acid with a linear or branched, alicyclic, aromatic or heterocyclic (C 2 -C 24 )alcohol, or an ester of (meth)acrylic acid with a (C 2 -C 24 )polyethylene glycol.

5. The aqueous dispersion of claim 4 , wherein the multifunctional (meth)acrylate compound is selected from the group consisting of glycerol dimethacrylate, ethylene glycol dimethacrylate, 1,3-butylene glycol dimethacrylate, 1,4-butylene glycol dimethacrylate, 1,2-propylene glycol dimethacrylate, 1,3-propylene glycol dimethacrylate, diethylene glycol dimethacrylate, 1,6-hexane diol dimethacrylate, bisphenol A dimethacrylate, bisphenol A ethoxylate dimethacrylate, pentaerythritol trimethacrylate, glycerol trimethacrylate, trimethylolpropane trimethacrylate, tris-2-hydroxyethyl isocyanurate trimethacrylate, ethoxylated pentaerythritol tetramethacrylate, 1,4-butylene glycol diacrylate, ethylene glycol diacrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, neopentylglycol diacrylate, triglycerol diacrylate, 1,6-hexane diol diacrylate, trimethylolpropane triacrylate, trimethylolpropane ethoxylate triacrylate, trimethylolpropane propoxylate triacrylate, pentaerythritol triacrylate, tris-2-hydroxyethyl isocyanurate triacrylate, glycerol triacrylate, pentaerythritol tetraacrylate, di-trimethylolpropane tetraacrylate, dipentaerythritol pentaacrylate, dipentaerythritol hexaacrylate, tris[2-(acryloyloxy)ethyl]isocyanurate, 2-[4,6-bis(2-propenoyloxyethyl)-1,3,5-triazin-2-yl]ethyl prop-2-enoate, and mixtures thereof.

6. The aqueous dispersion of claim 5 , wherein the multifunctional (meth)acrylate compound is selected from the group consisting of glycerol dimethacrylate, 1,4-butylene glycol dimethacrylate, ethylene glycol dimethacrylate, trimethylolpropane trimethacrylate, glycerol trimethacrylate, pentaerythritol triacrylate, 1,4-butylene glycol diacrylate, ethylene glycol diacrylate, trimethylolpropane triacrylate, glycerol triacrylate, pentaerythritol tetraacrylate, di-trimethylolpropane tetraacrylate, and mixtures thereof.

7. The aqueous dispersion of claim 1 , wherein the weight ratio between the multifunctional α,β-unsaturated carbonyl compound(s) (i) and the nanocellulose or microcrystalline cellulose (ii) ranges from 0.1 to 1.

8. The aqueous dispersion of claim 1 , wherein the nanocellulose or microcrystalline cellulose (ii) is in the form of fibrils having a median volume diameter (D(v; 0.5)) ranging from 150 nm to 8 μm.

9. The aqueous dispersion of claim 1 , wherein the nanocellulose or microcrystalline cellulose (ii) is dispersible in a solvent or a fragrance with a Log P of at least 1.5.

10. The aqueous dispersion of claim 1 , wherein the polymeric shell comprises at least one monoethylenically α,β-unsaturated carbonyl compound and/or poly(alkylene itaconate) (iii) selected from the group consisting of methacrylic acid, itaconic acid, 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, methyl methacrylate, ethyl methacrylate, isopropyl methacrylate, isobornyl methacrylate, and mixtures thereof.

11. The aqueous dispersion of claim 1 , wherein the polymeric shell comprises at least one multifunctional thiol compound (iv) selected from the group consisting of ethylene glycol bismercaptoacetate, glycol dimercaptoacetate, 1,8-dimercapto-3,6-dioxaoctane, dimercaptodiethyl sulfide, 1,6-hexanedithiol, propane-1,2,3-trithiol, 1,2-bis[(2-mercaptoethyl)thio]-3-mercaptopropane, tetrakis(7-mercapto-2,5-dithiaheptyl]methane, trimethylolpropane tris(2-mercaptoacetate), pentaerythritol tetrakis(2-mercaptoacetate), ethylene glycol bis(3-mercaptopropionate), dipentaerythritol hexakis(3-mercaptopropionate), 1,4-butanediol bis(3-mercaptopropionate), polycaprolactone tetra(3-mercaptopropionate), tris[2-(3-mercaptopropionyloxy)ethyl]isocyanurate, tetraethylene glycol bis(3-mercaptopropionate), ethoxylated trimethylolpropane tri(3m-ercapto-propionate), trimethylolethane trimercaptoacetate, 1,4-butanediol bismercaptoacetate, trithiocyanuric acid, pentaerythritol tetrakis(3-mercaptopropionate), trimethylolpropane tris(3-mercaptopropionate), trimethylolpropane tris(3-mercaptobutyrate), 1,4-butanediol bis(3-mercaptobutyrate), poly-2-mercaptoacetate, benzene-1,2-dithiol, 1,4-butanedithiol, 4,4′-biphenyldithiol, benzene-1,4-dithiol, toluene-3,4-dithiol, 1,4-dithiothreitol, 1,3,4-thiadiazole-2,5-dithiol, 1,3,5-benzenetrithiol, 4,4′-bis(mercaptomethylbiphenyl), 1,3,5-tris(3-mercaptobutyryloxyethyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, 3,7-dithia-1,9-nonanedithiol, and mixtures thereof.

12. The aqueous dispersion of claim 11 , wherein the at least one multifunctional thiol compound (iv) is selected from the group consisting of ethylene glycol bismercaptoacetate, glycol dimercaptoacetate, trimethylolpropane tris(3-mercaptopropionate), pentaerythritol tetrakis(3-mercaptopropionate), and mixtures thereof.

13. The aqueous dispersion of claim 1 , wherein the polymeric shell comprises at least one monofunctional thiol compound (iv) selected from the group consisting of 1-octanethiol, 1-decanethiol, 1-dodecanethiol, tert-octanethiol, tert-dodecanethiol, thioglycolic acid, and mixtures thereof.

14. The aqueous dispersion of claim 1 , wherein the aqueous dispersion comprises solid colloidal inorganic particles.

15. The aqueous dispersion of claim 1 , wherein the polymeric shell comprises at least one silyl (meth)acrylate compound (v) selected from the group consisting of trimethylsilyl (meth)acrylate, triethylsilyl (meth)acrylate, tripropylsilyl (meth)acrylate, triisopropylsilyl (meth)acrylate, tributylsilyl (meth)acrylate, tri-sec-butylsilyl (meth)acrylate, triisobutylsilyl (meth)acrylate, sec-butylmethylsilyl (meth)acrylate, sec-butyldimethylsilyl (meth)acrylate, dimethylpropylsilyl (meth)acrylate, monomethyldipropylsilyl (meth)acrylate, and methylethylpropylsilyl (meth)acrylate, 3-(trimethoxysilyl)propyl (meth)acrylate, 3-(triethoxysilyl)propyl (meth)acrylate, 3-(trichlorosilyl)propyl (meth)acrylate, and mixtures thereof.

16. The aqueous dispersion of claim 1 , wherein the hydrophobic core comprises a fragrance.

17. A process for the manufacture of an aqueous dispersion of claim 1 , comprising the following steps:
a—providing an oil-in-water emulsion having an oil phase and an aqueous phase, wherein the oil phase comprises the constituent(s) of

Assignees

• Takasago Perfumery Co Ltd

Inventors

• Ribaut Tiphaine
• Le Moue Laura
• Povazson Jeremy
• Bett William
• Warr Jonathan

Classifications

• C11D17/0013

  Liquid compositions with insoluble particles in suspension (C11D17/0021, C11D17/0026, C11D17/003 take precedence) · CPC title

• C11D3/3765

  in liquid compositions · CPC title

• C11D3/222

  Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin · CPC title

• C11D3/505

  encapsulated or adsorbed on a carrier, e.g. zeolite or clay · CPC title

• C08F2800/20

  as weight or mass percentages · CPC title