IP Library Granted Patent US 8,648,028
Granted Patent B2
US 8,648,028 · App. 12/995,615 · Granted Feb 11, 2014

Capsule with organic/inorganic hybrid wall

Inventor: Jan Looft (Niederbachem, DE)
Assignee: Symrise AG
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Quick Facts
Patent No.
US 8,648,028
App. No.
12/995,615
Granted
Feb 11, 2014
Kind
B2
Abstract

The present disclosure relates to a capsule having a core and a shell surrounding the core. The shell comprises a polymeric material produced by reacting a component (A) with a component (B). Component (A) comprises a polysiloxane bearing one or more amino groups and component (B) comprises one or more polyisocyanates. The disclosure also relates to processes for producing the capsules, methods of using the capsules, and to products containing the capsules.

Claims (87)

1. A capsule comprising a core and a shell surrounding the core,

wherein the shell comprises a polymeric material, and wherein the polymeric material is produced by reacting a component (A) with a component (B), wherein component (A) comprises one or more polysiloxanes bearing one or more amino groups and component (B) comprises one or more polyisocyanates; and the polymeric material comprises groups of structure G1:

[NH—CO—NR 1 —R 2 —Si(R 3 ) n O( 3-n )  (G1)

and optionally comprises groups of structure G2:

[NH—CO—NH]  (G2)

wherein:

R 1 is selected from the group consisting of H, an NH 2 -substituted unbranched alkyl, an NH 2 -substituted branched alkyl and an NH 2 -substituted cycloalkyl;

R 2 is an unsaturated or saturated hydrocarbon;

R 3 is selected from the group consisting of unbranched or branched alkyl and cycloalkyl;

n=0 or 1; and

each O atom bound directly to the Si atom of G1 is bound directly to a further Si atom.

2. The capsule as claimed in claim 1 , wherein the reaction is an interfacial reaction comprising contacting a first phase comprising component (A) with a second phase comprising component (B).

3. The capsule as claimed in claim 2 , wherein the second phase is dispersed in the first phase during the interfacial reaction and wherein the second phase further comprises one or more further ingredients of the core.

4. The capsule as claimed in claim 3 , wherein the further ingredient or ingredients are chemically inert with respect to component (B).

5. The capsule as claimed in claim 3 , wherein the second phase is emulsified in the first phase during the interfacial reaction.

6. The capsule as claimed in claim 1 , wherein (i) the amino group-bearing polysiloxanes of component (A) are water-soluble and/or (ii) the polyisocyanates of component (B) are water-insoluble.

7. The capsule as claimed in claim 1 , wherein (i) the amino group-bearing polysiloxanes of component (A) are present in the form of an aqueous solution or an aqueous colloid and/or (ii) the polyisocyanates of component (B) are present in the form of a dispersion in water during the reaction.

8. The capsule as claimed in claim 1 , wherein the amino group-bearing polysiloxanes of component (A) are produced by a process comprising:

(i) providing or producing:

(a) one or more aminoalkylalkoxysilanes of formula (I)

R 1 —NH—R 2 —Si(R 4 ) x (X 1 ) 3-x   (I),

and

(b) optionally providing or producing one or more further silanes of formula (II)

Si(R 5 ) y (X 2 ) 4-y   (II),

wherein:

R 1 is selected from the group consisting of H, an NH 2 -substituted unbranched alkyl, an NH 2 -substituted branched alkyl and an NH 2 -substituted cycloalkyl,

R 2 is an unbranched or branched alkylene,

R 4 is selected from the group consisting of unbranched or branched alkyl and cycloalkyl,

each X 1 is, independently of each further X 1 , a hydrolyzable group,

each R 5 is, independently of each further R 5 , selected from the group consisting of unbranched or branched alkyl and cycloalkyl,

each X 2 is, independently of each further X 2 , a hydrolyzable group,

x=0 or 1,

y=0, 1 or 2,

(ii) producing an aqueous solution of the aforementioned compounds,

(iii) setting process conditions to ensure the hydrolyzable groups are hydrolyzed,

(iv) removing compounds HX 1 and HX 2 from the mixture.

9. The capsule as claimed in claim 8 , wherein:

R 1 is selected from the group consisting of H, an NH 2 -substituted unbranched alkyl, an NH 2 -substituted branched alkyl containing 1 to 8 C atoms, and cycloalkyl containing 3 to 6 C atoms,

R 2 is an unbranched or branched alkylene containing 1 to 8 C atoms,

R 4 is selected from the group consisting of unbranched or branched alkyl containing 1 to 8 C atoms and cycloalkyl containing 3 to 6 C atoms,

each X 1 is, independently of each further X 1 , an alkyloxy containing 1 to 4 C atoms,

each R 5 is, independently of each further R 5 , selected from the group consisting of unbranched or branched alkyl containing 1 to 8 C atoms and cycloalkyl containing 3 to 6 C atoms,

and/or

each X 2 is, independently of each further X 2 , an alkyloxy containing 1 to 4 C atoms.

10. The capsule as claimed in claim 1 , wherein, component (A) comprises 0.2 to 4 mol of amino groups per 1 mol of isocyanate groups present in component (B).

11. The capsule as claimed in claim 1 , wherein the polyisocyanate or polyisocyanates of component (B) comprise two or more isocyanate groups per molecule.

12. The capsule as claimed in claim 11 , wherein the polyisocyanate or polyisocyanates of component (B) are selected from the group consisting of hexamethylene diisocyanate, isophorone diisocyanate and derivatives thereof, wherein each of the derivatives comprises two or more isocyanate groups and further comprises one or more groups selected from the group consisting of biuret, isocyanurate, uretdione and iminooxadiazinedione.

13. The capsule as claimed in claim 1 , wherein the capsule has a diameter of 1 to 500 μm.

14. The capsule as claimed in claim 1 , wherein the core comprises one or more further ingredients selected from the group consisting of odorous substance, dye, dye precursor, catalyst for chemical reactions, adhesive, reactive substance for adhesive applications, pharmaceutical active substance, cosmetic active substance, plant protection active substance, water repellent, flame retardant and solvent.

15. The capsule as claimed in claim 1 , wherein the core comprises one or more odorous substances selected from the group consisting of

extracts of natural raw materials and also fractions thereof, or ingredients isolated therefrom;

individual odorous substances from a group of hydrocarbons;

aliphatic aldehydes and acetals thereof;

aliphatic ketones and oximes thereof;

aliphatic sulfur-containing compounds;

aliphatic nitriles;

esters of aliphatic carboxylic acids;

formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoates of acyclic terpene alcohols;

acyclic terpene aldehydes and ketones and also dimethyl and diethyl acetals thereof;

cyclic terpene aldehydes and ketones;

cyclic and cycloaliphatic ethers;

cyclic and macrocyclic ketones;

cycloaliphatic aldehydes;

cycloaliphatic ketones;

esters of cyclic alcohols;

esters of cycloaliphatic alcohols;

esters of cycloaliphatic carboxylic acids;

esters of araliphatic alcohols and aliphatic carboxylic acids;

araliphatic ethers;

aromatic and araliphatic aldehydes;

aromatic and araliphatic ketones;

aromatic and araliphatic carboxylic acids and esters thereof;

nitrogen-containing aromatic compounds;

phenyl ethers and phenyl esters;

heterocyclic compounds; and

lactones,

wherein the shell is completely or substantially impervious to the odorous substance or substances.

16. A product comprising a capsule as claimed in claim 1 .

17. The product as claimed in claim 16 , wherein the product is a consumer goods product selected from the group consisting of personal care product, home care product and laundry care product.

18. A perfumed product comprising a capsule as claimed in claim 1 .

19. A process for producing a capsule as claimed in claim 1 , comprising:

(i) providing one or more substances to be encapsulated, one or more polyisocyanates and optionally providing a solvent,

(ii) providing or producing polysiloxanes bearing one or more amino groups,

(iii) producing a solution (1) comprising the substance or substances to be encapsulated, the polyisocyanate or polyisocyanates and the solvent, if present, wherein the solution (1) is not soluble in water,

(iv) producing a dispersion of solution (1) in an aqueous solution or an aqueous colloid of the polysiloxane or polysiloxanes,

(v) reacting the polyisocyanate or polyisocyanates with the polysiloxane or polysiloxanes, and

(vi) optionally subsequently maintaining the temperature in a range of 40 to 80° C. for 0.5 to 5 hours.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 19, 2011
From: LOOFT, JAN
To: SYMRISE AG
Reel/Frame 025662/0754 →
Priority Claims (1)
DE 10 2008 002 145 · Jun 2, 2008 · national
Continuity (1)
Related Publication 20110118161A1 · May 19, 2011