Aqueous peptide-stabilized polyurethane dispersions

Patent metadata

Field	Value
Publication number	US-2017342192-A1
Application number	US-201715480535-A
Country	US
Kind code	A1
Filing date	Apr 6, 2017
Priority date	Oct 14, 2014
Publication date	Nov 30, 2017
Grant date	—

Abstract

The present invention relates to aqueous peptide-stabilized polyurethane dispersions that can be used in various applications including adhesives and cosmetics, as they are surfactant and solvent free and have low VOC emissions. As hybrid materials, they provide for a versatile system that can be finely tuned and combine the advantageous properties of polyurethane and peptide materials. Also encompassed are processes for their production including dispersing an NCO-terminated polyurethane prepolymer into a continuous aqueous phase comprising one or more peptides, thereby forming peptide-stabilized polyurethane particles, compositions containing them and their use in cosmetics and adhesives.

First claim

1 . A process for manufacturing a peptide-stabilized polyurethane dispersion comprising:
(1) providing an NCO-terminated polyurethane prepolymer; and (2) dispersing said NCO-terminated polyurethane prepolymer into a continuous aqueous phase, wherein the continuous aqueous phase is an aqueous solution comprising one or more peptides, thereby forming a plurality of peptide-stabilized polyurethane particle.

2 . The process of claim 1 , wherein the aqueous solution comprises the one or more peptides in an amount of greater than or equal to 4 wt relative to the total weight of the prepolymer.

3 . The process of claim 1 , wherein the aqueous solution has a pH greater than the isoelectric point of the one or more peptides.

4 . The process of claim 1 , wherein the one or more peptides is prepared by hydrolysis of a natural protein.

5 . The process of claim 1 , wherein the NCO-terminated polyurethane prepolymer of step (1) is prepared from a reaction mixture comprising:
(a) at least one polyol, preferably with a number average molecular weight M n in the range of 400 g/mol to 10000 g/mol; and (b) at least one polyisocyanate, wherein the at least one polyisocyanate is used in molar excess relative to the hydroxy groups of the at least one polyol.

6 . The process of claim 5 , wherein the at least one polyol comprises
(a) a polyether polyol; (b) a polyester polyol; and/or (c) a polydimethylsiloxane polyol.

7 . The process according to claim 5 , wherein the reaction mixture comprises:
(a) a polyester polyol, having a number average molecular weight M n in the range of 400 g/mol to 5000 g/mol, a crystallinity of at least 20%, and a melting temperature T m in the range of 30° C. to 150° C., and (b) a polyether polyol, having a number average molecular weight M n in the range of 400 g/mol to 5000 g/mol, a crystallinity of less than 10% and a glass transition temperature T g in the range of −60° C. to 40° C., preferably wherein the crystallinity and the glass transition temperature are determined according to ISO11357, wherein the molar ratio of the polyester polyol (a) to the polyether polyol (b) is in the range of 1:10 to 10:1.

8 . The process according to claim 5 , wherein
(1) the ratio of the OH/NCO is 1:1.1 to 1:4, and/or (2) the at least one polyisocyanate is selected from the group consisting of isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), polymeric polyisocyanates based on IPDI or HDI, and mixtures thereof.

9 . The process of claim 1 , wherein the NCO-terminated polyurethane prepolymer:
(a) is a solution in an organic solvent; (b) has an average number molecular weight M n of 3000 to 12000; (c) comprises crystalline segments; and/or (d) is essentially free of electrically charged groups or monomeric units.

10 . The process according to claim 1 , wherein step (2) comprises:
(a) emulsifying the polyurethane prepolymer into the continuous aqueous phase to form a pre-emulsion; and (b) homogenizing the pre-emulsion to form a stable miniemulsion.

11 . The process according to claim 1 , wherein the dispersing step (2),
(a) is conditioned under a shear rate of at least 1,000,000/s, and/or (ii) an application of energy per time of at least 10 3 J per second per liter of the emulsion; and/or (b) comprises dispersing the prepolymer or the prepolymer solution into the continuous aqueous phase under a shear force to obtain an emulsion with droplet sizes of between 50 and 500 nm.

12 . The process of claim 1 , wherein the process further comprises the step (3) separating the plurality of peptide-stabilized polyurethane particle from the unreacted peptides.

13 . The process of claim 1 , wherein
the plurality of peptide-stabilized polyurethane particle is a plurality of polyurethane particle having a peptide corona; and/or wherein essentially no additional stabilizer molecules different from the peptides are added.

14 . An aqueous peptide-stabilized polyurethane dispersion obtained according to the process of claim 1 .

15 . A composition comprising the aqueous peptide-stabilized polyurethane dispersion of claim 14 .

Assignees

• Henkel Ag & Co Kgaa
• Max-Planck-Gesselschaft Zur Förderung Der Wss E V

Inventors

• Taden Andreas
• Landfester Katharina
• Breucker Laura

Classifications

• C08G18/4837 Primary

  and other oxyalkylene units · CPC title

• C08G18/4261

  prepared by oxyalkylation of polyesterpolyols · CPC title

• C08G18/3203 Primary

  Polyhydroxy compounds · CPC title

• C08G18/61

  Polysiloxanes · CPC title

• C07K1/12

  by hydrolysis {, i.e. solvolysis in general} · CPC title