EP-4734929-A1 - SYSTEM AND METHODS FOR MODIFYING SURFACE PROPERTIES OF KERATIN-CONTAINING SURFACES

Abstract

The technology disclosed teaches the tuning of surface properties of keratin-containing material, such as hair. One or more implementations include a catechol derivative that can be linked with a surface modifying component at a reactive handle removed from an aromatic ring; thereby maintaining the degree of substitution of the aromatic ring. The interaction of the catechol in the resulting structure with the keratin of the keratin-containing material increases adhesion of the surface modifying component. The technology disclosed provides an approach for modifying one or more properties of the keratin-containing material, such as the color, gloss, or frizz-resistance of hair, without using harsh conditions. Furthermore, the tunable nature of the resultant polymer, which may include a single surface modifying compound or combination of two or more, enables the simultaneous control of one or more cosmetic properties, such as hair repair and gray coverage.

Inventors

• WARNER, Nina Cochran

Assignees

• Edulis Labs Inc.

Dates

Publication Date

20260506

Application Date

20240516

Claims (1)

1. Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 CLAIMS 1. A system for tuning at least one surface property of a keratin-containing material, the system comprising: a first compound of a structure (I): wherein (i) the first compound comprises a keratin-binding catechol derivative, (ii) R2 represents an optional spacer, and (iii) R3 represents a first reactive handle; and a second compound having a second reactive handle, wherein the first reactive handle of the first compound reacts with the second reactive handle of the second compound in response to a stimulus, the stimulus causing the first compound to be linked with the second compound such that a degree of substitution of an aromatic ring of the first compound is maintained during the reaction. The system of claim 1, further comprising at least one of a crosslinker. 3. The system of claim 1, further comprising a metal ion configured to increase at least one of an adhesion property and a color of the keratin-containing material. 4. The system of claim 1, wherein R1 represents H or OH. 5. The system of claim 1, wherein the first reactive handle R3 is a polymerizable handle selected from one of a methacrylamide, an acrylamide, a methacrylate, or an acrylate. 6. The system of claim 1, wherein the first reactive handle R3 is selected from one of an amine, a carboxylic acid, a thiol, a hydroxyl, an alkene, an alkyne, an aldehyde, a succinimide ester, an azide, a dichlorotriazine, or an alcohol. {00944416.DOCX } Page 48 of 51 Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 7. The system of claim 1, wherein the optional spacer R2 represents a C1-4 alkyl group. 8. The system of claim 1, wherein the second reactive handle of the second compound is a polymerizable handle selected from one of a methacrylamide, an acrylamide, a methacrylate, or an acrylate. 9. The system of claim 1, wherein the second reactive handle of the second compound is selected from one of an amine, a carboxylic acid, a thiol, a hydroxyl, an alkene, an alkyne, an aldehyde, a succinimide ester, an azide, a dichlorotriazine, or an alcohol. 10. The system of claim 1, the system further comprising at least one of an initiator compound, wherein (i) the initiator compound is activatable by one or more stimuli and (ii) the one or more stimuli include one or more of a chemical stimulus, a heat stimulus, and a light stimulus. 11. The system of claim 1, wherein the second compound is a surface modifying compound configured to produce a microscale smoothing effect on a surface of the keratin- containing material. 12. The system of claim 1, wherein the second compound is a surface modifying compound configured to increase a hydrophobicity of a surface of the keratin-containing material, and the surface modifying compound further comprises a hydrophobic moiety selected from an alkyl chain or a siloxane. 13. The system of claim 1, wherein the second compound is a surface modifying compound configured to absorb, scatter, or emit light, thereby producing a color change in the keratin-containing material. 14. The system of claim 1, further including microfibers. 15. The system of claim 1, further including at least one of an organic nanoparticle, an inorganic nanoparticle, an optical brightening agent, a light-reflecting compound, a light- refracting compound, or a light-emitting compound. 16. The system of claim 1, wherein the stimulus is configured to cause the first compound to be linked with the second compound upon mixture of components of the system, prior to an application of the mixture to the keratin-containing material. {00944416.DOCX } Page 49 of 51 Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 17. The system of claim 1, wherein the stimulus is configured to cause the first compound to be linked with the second compound via an in situ reaction, subsequent to an application of system components the keratin-containing material. 18. The system of claim 1, wherein a pH of the system is less than or equal to 7.5. {00944416.DOCX } Page 50 of 51

Description

Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 SYSTEM AND METHODS FOR MODIFYING SURFACE PROPERTIES OF KERATIN-CONTAINING SURFACES Inventors: Nina WARNER PRIORITY APPLICATIONS [0001] This application claims the benefit of and priority to U.S. Provisional Patent Application No.63/523,627, titled “CATECHOL DERIVATIVES WITH STIMULI- RESPONSIVE ADHESION TO HUMAN HAIR”, filed 27 June 2023 (Atty Docket No. EDUL 1000-1), the content of which is incorporated herein by reference in its entirety. FIELD OF THE TECHNOLOGY DISCLOSED [0002] The technology disclosed generally relates to a class of coatings for human hair based on catechol derivatives, and more specifically to a class of coatings used to tune the feel, color, or appearance of human hair through stimuli-responsive adhesion of derivatized catechols. BACKGROUND [0003] The subject matter discussed in this section should not be assumed to be prior art merely as a result of its mention in this section. Similarly, a problem mentioned in this section or associated with the subject matter provided as background should not be assumed to have been previously recognized in the prior art. The subject matter in this section merely represents different approaches, which in and of themselves can also correspond to implementations of the claimed technology. [0004] Semi-permanent or permanent modification of the surface properties of human hair (i.e., for the purpose of tuning apparent color, gloss/shine, smoothness, or thickness) is a widely desired, yet largely unrealized cosmetic goal. Development of a haircare system capable of performing said task requires satisfying a diverse suite of material requirements. For example, the material should be biocompatible; further, the conditions used during application should not compromise human or hair health. Additionally, the material should exhibit strong, versatile adhesion to achieve semi-permanence or permanence. An enormous variety of hair surface chemistry exists dependent upon hair condition, several physical characteristics (e.g., fine or coarse, presence and extent of curl), individual ethnicity, processing history, and so on. The design of a single material or material class capable of adhering to all hair is technically challenging as a result of this variability. {00944416.DOCX } Page 1 of 51 Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 [0005] Certain properties of the material are of particular interest to the consumer. Ideally, the material is stable under routine weathering and/or grooming conditions. A material with long-duration adhesion onto the surface of human hair, e.g., a hair colorant, should be capable of withstanding exposure to routine conditions the hair is likely to encounter throughout the day (e.g., friction from brushing, heat from styling, hydration during bathing, and/or surfactant exposure from washing) without significant loss of adhesive strength. Additionally, orthogonal control of the material properties is of significant value. This is to say that key coating properties (apparent color, adhesive strength, elasticity, hydrophobicity, etc.) should be controllable in such a way that altering one property does not, in turn, significantly alter other properties. For example, this may be tuning the color of hair to achieve a blonde appearance without compromising the longevity or stiffness of the coating. [0006] An opportunity arises for the modification of one or more hair properties to achieve a desired cosmetic result without unduly impacting another hair property. An opportunity also arises for the mitigation of hair damage and detrimental impacts to health resulting from modification of one or more hair properties. Accordingly, one or more implementations of the technology disclosed herein include systems, methods, and compositions for achieving one or more desirable cosmetic results via semi-permanent or permanent modifications of hair properties including, but not limited to, color, shine, hydrophobicity, smoothness, and frizz. One or more implementations of the disclosed technology further include semi-permanent or permanent modifications of one or more hair properties that are associated with at least one of (i) reduced damage to the hair itself and (ii) reduced toxicity, relative to alternative products and techniques traditionally used to achieve similar results. BRIEF DESCRIPTION OF THE DRAWINGS [0007] In the drawings, like reference characters generally refer to like parts throughout the different views. Also, the drawings are not necessarily to scale, with an emphasis instead generally being placed upon illustrating the principles of the technology disclosed. In the following description, one or more implementations of the technology disclosed are described with reference to the following drawings. [0008] FIG.1 illustrates an example hair surface modifying system, according to many implementations of the technology described herein. {00944416.DOCX