Process for the preparation of microcapsules

Active Publication Date: 2019-09-05
FIRMENICH SA
View PDF0 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0007]There is therefore still a need to provide polyurea-based capsules prepared by simplified and cost-effective processes that would be olfactively performing and stable in challenging media such as surfactant-based consumer products.
[0008]It has now been found, that contrary to what could be expected based on prior teachings, performing polyurea-based microcapsules encapsulating a hydrophobic active ingredient such as a perfume oil could be obtained with a shell essentially formed from a polyisocyanate other than a diisocyanate. The process of the invention therefore provides a solution to the above-mentioned problems as it allows preparing capsules in the absence of an additional cross-linker with a membrane consisting of polymerised polyisocyanate essentially formed from a polyisocyanate comprising at least three isocyanate functional groups, preferably aromatic and free from diisocyanate. Unexpectedly, even with very limited amounts of such polyisocyanate used, those capsules demonstrate a high performance in terms of stability and olfactive performance.

Problems solved by technology

One of the problems faced by the perfumery industry lies in the relatively rapid loss of olfactive benefit provided by odoriferous compounds due to their volatility, particularly that of “top-notes”.
For instance, fragranced personal and household cleansers containing high levels of aggressive surfactant detergents are very challenging for the stability of microcapsules.
However, capsules such as aminoplast ones suffer from stability problems when used in consumer products comprising surfactants, such as perfumery consumer products, especially after prolonged storage at elevated temperatures.
The leakage phenomenon reduces the efficiency of the capsules to protect the active and provide its controlled release.
However, these capsules are not always satisfactory in terms of mechanical properties as that are not friable, which can negatively impact their olfactive performance represented by the odor intensity perceived during handling and after intentional breakage e.g. by rubbing.
However, although diisocyanates are known to be very reactive and therefore attractive to form a polymeric shell, there are not always considered as suitable component from a safety standpoint.
More particularly, according to this article, even if close to an equiweight of polyisocyanate is used to encapsulate large, high log P molecule (di-2-ethylhexylphtalate) expected to show low propension to leakage through a thick capsule shell, the obtained capsules show poor storage stability when placed in organic solvent, with very high leakage of the (di-2-ethylhexylphtalate) out of the capsule, thus suggesting the polyisocyanate (triisocyanate) used is not suited to yield shell capable of preventing core oil leakage in tough media potentially inducing leakage, be organic solvent or aqueous solutions with high levels of surfactants.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Process for the preparation of microcapsules
  • Process for the preparation of microcapsules
  • Process for the preparation of microcapsules

Examples

Experimental program
Comparison scheme
Effect test

Example

Example 1

Preparation of Capsules A to I

[0133]Microcapsules A to I were prepared with the following ingredients:

CapsulesCapsulesCapsulesCapsulesComparativeA to EFGHcapsule IAmountAmountAmountAmountAmountIngredient[g][g][g][g][g]Oil Phase21.727.033.738.620.9Perfume oil (perfume A) 1)variable24.330.434.819.65Polyisocyanate2)variable2.73.33.81.25Water phase77.7272.665.8560.9878.61Guanidine Carbonate3)00000.4Gum Arabic4)0.981.121.211.351.16Water76.7471.4864.6459.6377.051) see Table 22)Takenate ® D-110N (trimethylol propane adduct of xylylene diisocyanate); origin and trademark from Mitsui Chemicals, 75% polyisocyanate / 25% ethyl acetate3)origin: Fluka4)origin Alland & Robert

TABLE 2Composition of Perfume ARaw mat% in formulaSTIRRALLYL ACETATE4.5%BENZYL ACETATE0.9%ALDEHYDE C102.1%HEXYLCINNAMIC ALDEHYDE14.3% ALLYL CAPROATE0.7%Ethyl 2-methyl-pentanoate0.9%BENZYL BENZOATE35.3% CITRONELLYL NITRILE1.8%CORANOL 1)5.4%DIHYDROMYRCENOL5.4%FRUCTALATE ®2)5.4%HEDIONE ®3)14.9% LIMONENE2.4%LINALOOL1.0%METH

Example

Example 2

Preparation of Capsules J

[0139]The oil phase was prepared by admixing 1.6 g of polyisocyanate (trimethylol propane adduct of xylylene diisocyanate, Takenate® D-110N, origin and trademark from Mitsui Chemicals) with 25.4 g of perfume oil A (compositions defined in Table 2).

[0140]The aqueous phase was prepared by dissolving 0.1 g of sugar beet pectin (origin from CP Kelco) in 72.36 g of water. The emulsion was prepared by dispersing the perfume / polyisocyanate premix oil in the aqueous phase with the stirrer at 230 rpm. The temperature was raised to 70° C. and was kept at 70° C. for 1 h30 to allow the curing of the capsules. At this point, capsules were formed, cross-linked and stable. The mixture was left to cool down to room temperature.

[0141]After encapsulation and use of the Takenate D-110N to produce the capsule wall, the residual level of unreacted polyisocyanate in the perfume oil was very low and therefore the internal core of the capsule was essentially made of the per

Example

Example 3

Preparation of Capsules K

[0143]The oil phase was prepared by admixing 2.2 g of polyisocyanate (trimethylol propane adduct of xylylene diisocyanate, Takenate® D-110N, origin and trademark from Mitsui Chemicals) with 19.6 g of perfume oil A (compositions defined in Table 2).

[0144]The aqueous phase was prepared by dissolving 1.2 g of modified starch (Hicap-100® origin from Ingredion Inc) in 76.7 g of water. The emulsion was prepared by dispersing the perfume / polyisocyanate premix oil in the aqueous phase with the stirrer at 230 rpm. The temperature was raised to 70° C. and was kept at 70° C. for 1 h30 to allow the curing of the capsules. At this point, capsules were formed, cross-linked and stable. The mixture was left to cool down to room temperature.

[0145]After encapsulation and use of the Takenate D-110N to produce the capsule wall, the residual level of unreacted polyisocyanate in the perfume oil was very low and therefore the internal core of the capsule was essentially ma

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

PropertyMeasurementUnit
Percent by massaaaaaaaaaa
Fractionaaaaaaaaaa
Fractionaaaaaaaaaa
Login to view more

Abstract

The present invention relates to a new process for the preparation of microcapsules. Microcapsules obtainable by said process are also an object of the invention. Perfuming compositions and consumer products comprising said capsules, in particular perfumed consumer products in the form of home care or personal care products, are also part of the invention.

Description

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Owner FIRMENICH SA
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products