IP Library › Granted Patent US 9,358,189
Granted Patent B2
US 9,358,189 · App. 14/357,433 · Granted Jun 7, 2016

Stable formaldehyde-free microcapsules

Inventors: Damien Berthier (Geneva, CH); Géraldine Leon (Geneva, CH); Nicolas Paret (Geneva, CH); Lahoussine Ouali (Geneva, CH)
Assignee: Firmenich SA
A61K8/11A61K8/062A61K8/416A61K8/84A61L9/012A61Q5/00A61Q13/00A61Q19/00B01J13/14C11B9/00C11D3/505C11D17/0039A61K2008/115A61K2800/30A61K2800/412
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Quick Facts
Patent No.
US 9,358,189
App. No.
14/357,433
Granted
Jun 7, 2016
Kind
B2
Abstract

The present invention relates to water-dispersible core-shell microcapsules essentially free of formaldehyde. In particular it concerns core-shell microcapsules having a shell obtained by reacting polyisocyanates or polyoxirans cross-linkers and oligomeric compositions which are the reaction products between a polyamine component and a particular mixture of glyoxal and a C 4-6 2,2-dialkoxy-ethanal. The present invention comprises also the invention's core-shell microcapsules as part of a perfuming composition or of a perfuming consumer product.

Claims (30)

1. A process for the preparation of a core-shell microcapsule, said process comprising the steps of:

1) preparing an oligomeric composition comprising the reaction product of, or obtainable by reacting together:

a) a polyamine component in the form of melamine or of a mixture of melamine and at least one C 1-4 compound comprising two NH 2 functional groups;

b) an aldehyde component in the form of a mixture of glyoxal, a C 4-6 2,2-dialkoxy-ethanal and optionally a glyoxalate, said mixture having a molar ratio glyoxal/C 4-6 2,2-dialkoxy-ethanal comprised between 1/1 and 10/1; and

c) a protic acid catalyst;

2) preparing an oil-in-water dispersion, wherein the droplet size is comprised between 1 and 600 μm, and comprising:

i) an oil;

ii) a water medium;

iii) at least an oligomeric composition as obtained in step 1);

iv) at least a cross-linker selected amongst:

A) C 4 -C 12 aromatic or aliphatic di- or tri-isocyanates and their biurets, triurets, trimers and trimethylol propane-adduct; and/or

B) a di- or tri-oxiran compounds of formula

A-(oxiran-2-ylmethyl) n

wherein n stands for 2 or 3 and A represents a C 2 -C 6 group optionally comprising from 2 to 6 nitrogen and/or oxygen atoms;

v) optionally a C 1-4 compound comprising two NH 2 functional groups;

3) heating said dispersion;

4) cooling said dispersion; and

5) optionally adding to the dispersion of step 4) at least one cationic polymer and/or urea or ethylene urea; and

6) optionally drying the final dispersion to obtain the dried core-shell microcapsule.

2. A process according to claim 1 , wherein the dispersion comprises:

between 10% and 50% of oil;

between 1% and 20% of oligomeric composition;

between 0.5% and 15% of at least a cross-linker percentage being expressed on a w/w basis relative to the total weight of the dispersion.

3. A process according to claim 1 , wherein the water medium comprises between 0% and 5% of at least a stabilizer and between 0% and 10% of at least a polyol, percentage being expressed on a w/w basis relative to the total weight of the dispersion.

4. A process according to claim 3 , wherein said stabilizer is an ionic surfactant and said polyol is an aliphatic polymeric polyol.

5. A process according to claim 1 , wherein said polyamine component is a mixture of melamine and at least one compound selected amongst urea, 1H-1,2,4-triazole-3,5-diamine and mixtures thereof, and the molar ratio melamine/C 1-4 compound comprising two NH 2 functional groups comprised between 2/1 and 1/3.

6. A process according to claim 1 , wherein said aldehyde component is a mixture of glyoxal and at least one of a glyoxalate, 2,2-dimethoxy-ethanal, 2,2-diethoxy-ethanal and mixtures thereof, and has a molar ratio glyoxal/2,2-dialkoxy-ethanal comprised between 2.2/1 and 6.5/1 and the molar ratio glyoxal/glyoxalate is comprised between 4/1 and 1/1.

7. A process according to claim 1 , wherein there is added an amount of at least one cationic polymer comprised between 0% and 60% percentage being expressed on a w/w basis relative to the total weight of the resin.

8. A process according to claim 1 , wherein said di- or thi-isocyanate is selected amongst hexamethylene diisocyanate, isophorone diisocyanate, xylylene diisocyanate, toluene diisocyanate, a trimethylol propane-adduct of toluene diisocyanate, a trimethylol propane-adduct of xylylene diisocyanate, a trimer of hexamethylene diisocyanate, a trimer of isophorone diisocyanate, a trimethylol propane-adduct of hexamethylene diisocyanate or a biuret of hexamethylene diisocyanate.

9. A process according to claim 1 , wherein said di- or tri-oxiran compound is selected amongst 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione, 4-(oxiran-2-ylmethoxy)-N,N-bis(oxiran-2-ylmethyl)aniline, 1,3-bis(oxiran-2-ylmethoxy)benzene, 1,2-bis(oxiran-2-ylmethoxy)ethane and 2,2′-(2-ethyl-2-((oxiran-2-ylmethoxy)methyl)propane-1,3-diyl)bis(oxy)bis(methylene)dioxirane.

Assignments (2)
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNOR NAME AND APPL. NO. ON INSIDE ASSIGNMENT PREVIOUSLY RECORDED AT REEL: 032862 FRAME: 0103. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Oct 30, 2014
From: BERTHIER, DAMIEN; LEON, GERALDINE; PARET, NICOLAS; OUALI, LAHOUSSINE
To: FIRMENICH SA
Reel/Frame 034112/0984 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 9, 2014
From: BERTHIER, DAMIEN; LEON, GERALDINE; PARET, NICOLAS; OUALI, LAHOUSSINE
To: FIRMENICH SA
Reel/Frame 032862/0103 →
Priority Claims (2)
EP 11188600 · Nov 10, 2011 · regional
EP 12156387 · Feb 21, 2012 · regional
Continuity (1)
Related Publication 20140322283A1 · Oct 30, 2014