Core-shell capsules prepared with linear and cyclic aliphatic polyisocyanates
The present invention relates to core-shell capsules prepared with linear and/or branched and cyclic aliphatic polyisocyanates. In particular, the present invention discloses a core-shell capsule, wherein the shell comprises or consists of a polymeric material which is produced or producible by reacting two components, the first component comprising or consisting of at least one linear aliphatic polyisocyanate and/or at least one branched aliphatic polyisocyanate having more than one isocyanate group, respectively, and at least one cyclic aliphatic polyisocyanate having more than one isocyanate group, the second component comprising or consisting of one or more crosslinking agent(s). Furthermore, a product comprising the present core-shell capsule, a process for producing the present core-shell capsules and the use of the present core-shell capsules is provided.
1. A core-shell capsule comprising a core and a shell,
the shell consisting of a product produced or producible by reacting one or more linear and/or branched aliphatic polyisocyanates having more than one isocyanate group and one or more cyclic aliphatic polyisocyanates having more than one isocyanate group with one or more crosslinking agents, wherein:
the one or more linear and/or branched aliphatic polyisocyanates are selected from the group consisting of pentamethylene diisocyanate, hexamethylene diisocyanate, ethyl ester lysine triisocyanate, lysine diisocyanate ethyl ester, and oligomers and/or adducts thereof, wherein the oligomers are biurets, isocyanurates, uretdiones, or iminooxadiazinediones and the adducts are trimethylol propane adducts, and
the one or more cyclic aliphatic polyisocyanates are selected from the group consisting of 1,3-bis(isocyanatomethyl)cyclohexane, 1,2-bis(isocyanatomethyl)-cyclohexane, 1,4-bis(isocyanatomethyl)cyclohexane, and derivatives thereof.
2. The core-shell capsule of claim 1 , wherein the one or more linear and/or branched aliphatic polyisocyanates and the one or more cyclic aliphatic polyisocyanates are free of aromatic structures.
3. The core-shell capsule of claim 1 , wherein the one or more crosslinking agents are selected from polyamines with more than one amino group and salts thereof.
4. The core-shell capsule of claim 3 , wherein the one or more crosslinking agents contain 0.5 to 4 moles of amino groups per mole of isocyanate groups in the one or more linear and/or branched aliphatic polyisocyanates and the one or more cyclic aliphatic polyisocyanates.
5. The core-shell capsule of claim 3 , wherein the one or more crosslinking agents are selected from guanidine carbonate, guanidine hydrochloride, tris(2-aminoethyl)amine, ethylenediamine, butylenediamine, propanediamine, pentane-1,5-diamine, phenylenediamine, and linear or branched polyethyleneimines, and diethylenetriamine.
6. The core-shell capsule of claim 3 , wherein
the one or more linear and/or branched aliphatic polyisocyanates are selected from the group consisting of pentamethylene diisocyanate, hexamethylene diisocyanate, and oligomers and/or adducts thereof, wherein the oligomers are biurets, isocyanurates, uretdiones, or iminooxadiazinediones and the adducts are trimethylol propane adducts, and
the one or more cyclic aliphatic polyisocyanates are selected from the group consisting of 1,3-bis(isocyanatomethyl)cyclohexane, 1,2-bis(isocyanatomethyl)-cyclohexane, 1,4-bis(isocyanatomethyl)cyclohexane, and derivatives thereof.
7. The core-shell capsule of claim 6 , wherein the one or more cyclic aliphatic polyisocyanates is 1,3-bis(isocyanatomethyl)cyclohexane.
8. The core-shell capsule of claim 1 , wherein the capsule is a microcapsule with a diameter of 2 to 500 μm.
9. The core-shell capsule of claim 1 , wherein the core comprises one or more ingredients selected from odorous substances, aroma molecules, cooling agents, transient receptor potential vanilloid 1/transient receptor potential vanilloid 3 modulators, dyes, dye precursors, phase change materials, catalysts for chemical reactions, adhesives, reactive substances for adhesive applications, pharmaceutical active substances, UV-filters, cosmetic active substances, plant protection active substances, insect repellents, water repellents, flame retardants, agrochemicals, lubricants, and solvents.
10. The core-shell capsule of claim 1 , wherein the one or more linear and/or branched aliphatic polyisocyanates and the one or more cyclic aliphatic polyisocyanates are in a weight ratio of 9:1 to 1:9.
11. A product comprising the core-shell capsule of claim 1 .
12. A process for producing the core-shell capsule of claim 1 comprising:
(i) providing the one or more linear and/or branched aliphatic polyisocyanates and the one or more cyclic aliphatic polyisocyanates, one or more ingredients to be encapsulated, and optionally, one or more solvents;
(ii) providing the one or more crosslinking agents;
(iii) producing a solution (I) comprising the components of (i), wherein the solution (I) is not water-soluble;
(iv) producing a dispersion of the solution (I) in an aqueous solution (II) comprising the components of (ii);
(v) reacting the one or more linear and/or branched aliphatic polyisocyanates and the one or more cyclic aliphatic polyisocyanates of the solution (I) with the one or more crosslinking agents of the solution (II); and
(vi) optionally, maintaining a reaction temperature of 40 to 80° C. for 0.5 to 5 hours.
13. A method for perfuming a textile, hair, skin, a surface, and/or ambient air comprising applying or releasing the core-shell capsule of claim 1 to the textile, the hair, the skin, the surface, and/or the ambient air.
14. A core-shell capsule comprising a core and a shell,
the shell consisting of polymeric material produced or producible by reacting one or more linear and/or branched aliphatic polyisocyanates having more than one isocyanate group and one or more cyclic aliphatic polyisocyanates having more than one isocyanate group with one or more crosslinking agents, wherein:
the one or more linear and/or branched aliphatic polyisocyanates are selected from pentamethylene diisocyanate, hexamethylene diisocyanate, and oligomers and/or adducts thereof, wherein the oligomers are biurets, isocyanurates, uretdiones, or iminooxadiazinediones and the adducts are trimethylol propane adducts,
the one or more cyclic aliphatic polyisocyanates are selected from 1,3-bis(isocyanatomethyl)cyclohexane, 1,2-bis(isocyanatomethyl)-cyclohexane, 1,4-bis(isocyanatomethyl)cyclohexane, and derivatives thereof, and
the one or more crosslinking agents are selected from polyamines with more than one amino group and salts thereof.
15. The core-shell capsule of claim 14 , wherein the one or more cyclic aliphatic polyisocyanates is 1,3-bis(isocyanatomethyl)cyclohexane.