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.

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 51Nonprovisional 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 }Page 2 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2

[0009] FIG.2 illustrates a schematic diagram of catechol adhesion to keratin-containing surfaces.

[0010] FIG.3 illustrates a schematic diagram of example reaction pathways by which an adhesive catechol-containing compound and an example surface modifying compound may be linked.

[0011] FIGS.4A, 4B, 5A and 5B illustrate example hair surface modifying methods, according to one or more implementations of the technology described herein.

[0012] FIGS.6A and 6B illustrate light microscope images of damaged hair before and after treatment with an example hair surface modifying composition. DETAILED DESCRIPTION

[0013] The following detailed description is made with reference to the figures. Sample implementations are described to illustrate the technology disclosed, not to limit its scope, which is defined by the claims. Those of ordinary skill in the art will recognize a variety of equivalent variations on the description that follows.

[0014] The cosmetics industry is substantial in terms of both market value and the variety of product offerings available to consumers. A subset of the cosmetics industry is directed towards haircare to address an array of consumer desires related to hair health and beauty via products marketed to consumers for personal use as well as professional haircare services. Haircare alone accounts for a sizable portion of the cosmetics industry, as evidenced the haircare industry’s total market value of over 100 billion USD. In order to achieve consumer goals, haircare products often modify the material properties of hair for cosmetic purposes. Modifiable properties of hair frequently targeted by haircare products may include, for example, hydrophobicity, light reflectance, porosity, fiber alignment, elasticity, pigmentation, the density and type of chemical bonds, and countless others. The modification of hair properties including, but not limited to, those listed can address countless concerns commonly cited by consumers, such as hair shape, thickness, volume and texture; surface smoothness and shine; hair strength and resistance to breakage; hair color, including tone and shade; frizz-resistance; and oil build-up or resistance.

[0015] Modification of one or more hair properties, discussed above, can be achieved in a temporary, semi-permanent, or permanent manner. Achieving these benefits in a semi- permanent or permanent manner is often desirable to consumers, but the production of longer-lasting results is frequently associated with less desirable consequences. Semi- permanent or permanent techniques for hair modification, generally speaking, are{00944416.DOCX }Page 3 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 significantly more complex, rely upon the use of highly toxic chemicals, and cause damage with respect to the hair shaft itself. While safer, less-abrasive alternatives exist, these alternatives tend to offer temporary results. For example, improvement of hair shine and smoothness can be safely achieved by conventional conditioning agents such as oils or silicones, however, conventional conditioning agents are readily removed with washing, reducing the effective lifespan of the applied treatment. More permanent modification of hair shine is achievable through use of toxic aldehyde-based crosslinkers such as formaldehyde, a classified carcinogen that exposes both the consumer receiving the treatment and the technician or stylist applying the treatment to the health risks associated with formaldehyde or other similarly-used toxic compounds.

[0016] The average consumer is most likely aware of the issues associated with haircare treatment permanence within the context of hair dyeing. Temporary or semi-permanent dyeing of hair typically uses pre-formed dyes loosely bound to the hair surface by non-covalent interactions, but this type of dye yields only temporary modification of hair color that deteriorates with routine hair washing. More permanent dyeing of hair is achievable by processes like oxidative polymerization of aromatic diamines within the hair cortex. Aromatic diamines are often highly toxic and their application to hair dyeing processes requires the use of harsh oxidants, such as hydrogen peroxide and alkalizing agents (ammonia, ethanolamine, etc.) to swell the hair and catalyze the polymerization. The chemical compounds used in this example of permanent hair dyeing and many other chemicals used in alternative permanent dyeing techniques cause irreversible damage to the structure of the hair. Hair damage is even more pronounced when lightening the hair, sometimes referred to as “bleaching” one’s hair. A common hair lightening process that includes using alkaline hydrogen peroxide in the presence of catalysts (e.g., persulfates) results in extensive off-target oxidation of surface-bound lipids, amino acid side groups, disulfide bonds, and structural proteins. The off-target oxidation leads to hair damage in the form of dullness, frizz, and strength reduction amongst other undesirable cosmetic effects. In effect, these existing hair treatment or modification systems are plagued by a ‘trade-off’ conundrum in which the realization of one desirable trait, such as a cosmetic property is coupled with the loss of a second, as well as the potential risk of exposure to highly toxic compounds.

[0017] The technology disclosed provides a solution to the issues described above relating to haircare treatments. The technology disclosed includes systems, methods, and compositions for tuning the surface properties of keratin-containing material, such as hair. The technology disclosed includes a catechol derivative that can be linked with a surface modifying{00944416.DOCX }Page 4 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 component at a reactive handle removed from the aromatic ring; thus, the reaction between the catechol derivative and the surface modifying component maintains the degree of substitution of the aromatic ring.

[0018] The interaction of the catechol (or catechols) in the resulting structure with the keratin of the keratin-containing material increases adhesion of the surface modifying component, improving longevity of treatment (see, e.g., the description below with reference to Tables 1 through 5 and FIGs.6A through 6B). The technology disclosed modifies one or more properties of the keratin-containing material without using strongly oxidizing conditions or strongly basic conditions, and therefore provides a mild approach for durable modification of the cosmetic properties of the material, such as the color, gloss, frizz-resistance, or lightness of hair. 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.

[0019] One or more implementations of the disclosed technology are described below. First, certain terminology and acronyms will be introduced to complement later-described aspects of the technology disclosed. Next, the composition and structure of a surface modifying compound, as well as the application of the surface modifying compound to a keratin-containing surface resulting in modification of surface properties, are described. The discussion continues to expand upon this chemistry with one or more methods for application to human hair and other keratin-containing material, further examples of use cases, and objective indicia of non-obviousness and novelty for the technology disclosed. Terminology and Overview of the Modification of Hair

[0020] The description below refers to a system for tuning the surface properties of a keratin-containing material (e.g., hair), the system comprising a keratin-binding catechol derivative and a surface modifying compound. Some implementations alternatively include a keratin-binding catechol derivative and a compound configured to react with a surface modifying compound. A first reactive handle of the keratin-binding catechol derivative reacts with a second reactive handle of the surface modifying compound (or compound configured to react with a surface modifying compound, described further below) in response to a stimulus, causing the keratin-binding catechol derivative to be linked with the surface modifying compound such that a degree of substitution of an aromatic ring of the first compound is maintained during the reaction.{00944416.DOCX }Page 5 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2

[0021] A plurality of terms referenced herein will first be defined, as well as specifying analogous terms that may be used interchangeably and should be considered conceptually equivalent. The terms defined below (and terms derived therefrom) will be used in the present disclosure in the broadest meaning thereof. Additionally, a glossary of acronyms is provided.

[0022] Implementations of the technology disclosed relate to the modification of surface properties of keratin-containing surfaces, such as hair, nails, skin, teeth, and other keratin- containing material readily recognizable to a user skilled in the art. For clarity and conciseness, the implementations and examples herein are described with reference to hair, the surface of hair, and one or more modifiable surface properties of hair. However, it is to be understood that any references to hair, or omissions of other keratin-containing surfaces, is purely for illustrative purposes and should not be considered limiting to the spirit or scope of the technology disclosed. Many disclosed systems and methods herein include particular compounds, chemical structures, chemical and physical reactions, and processes comprising ordered lists of two or more reactions configured to modify one or more surface properties of keratin-containing materials. A user of ordinary skill in the art will recognize that the adhesion compound(s) and / or surface modifying compound(s) described herein with reference to the technology disclosed are broadly applicable to one or more keratin- containing surfaces. General Chemistry Terminology

[0023] The description below refers to a variety of different reactive groups, i.e., one or more chemical functional groups or functionalities that can participate in a chemical reaction resulting in the linkage of one molecule to another. An alkyl is a functional group that is aliphatic in nature, i.e., compounds with only carbon and hydrogen, and can be saturated or unsaturated. An aromatic ring refers to a compound comprising a conjugated planar six- membered ring system. Azo compounds refer to compounds containing the azo functionality including two nitrogen atoms linked to one another, i.e., -N=N-. A catechol, as referred to herein, can include any molecule containing an aromatic group with two or more hydroxyl groups directly bonding to the ring. A siloxane compound contains a functional group including two silicon atoms bound to an oxygen, i.e., -Si-O-Si-.

[0024] A polymer refers to a chemical structure composed of repeating subunits (i.e., each subunit is a monomer). Polymers usually have a high molecular weight due to the multiple monomers linked together. A monomer is a molecule capable of reacting with at{00944416.DOCX }Page 6 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 least one other monomer to form a polymer or network through polymerization. Copolymerization refers to simultaneous polymerization of two or more different monomers. Herein, a polymerizable handle is a functional group capable of polymerizing with itself, such as methacrylate, acrylate, methacrylamide, acrylamide, vinyl, and a number of additional polymerizable handles readily recognizable to a user skilled in the art. For example, an acrylic compound refers to a compound containing a polymerizable handle comprising acrylate or methacrylate. A non-polymerizable handle refers to a functional group that does not polymerize with itself. However, it is to be understood that a non-polymerizable handle may be able to react with a functional group of another class in order to form a bond and / or eventually form a polymer.

[0025] An initiator is a source of chemical species that reacts with a monomer to form an intermediate compound capable of linking with at least one other monomer, thereby creating a polymer. The activation of an initiator is triggered by a stimulus. A stimulus is an electromagnetic, chemical, or mechanical event that triggers the onset of a chemical reaction. An electromagnetic stimulus could refer to a change in UV light, visible light, or infrared radiation. A chemical stimulus could refer to a change in pH, ionic strength, redox potential, or introduction of a specific chemical substance. A mechanical stimulus could refer to a change in pressure, friction, or mixing. A user skilled in the art will recognize that a broad range of chemical stimuli exist, as well as their appropriate and / or compatible applications. The examples listed above are purely illustrative and should not be considered limiting. Moreover, it is to be understood that the activation of an initiator may be triggered by a combination of multiple stimuli. However, for the sake of clarity and conciseness, the implementations disclosed herein will be described with reference to a “stimulus” even though a particular stimulus may technically include a combination of numerous stimuli (e.g., a chemical stimulus combined with heat, multiple chemical stimuli further activated by mixing, and so on). Surface Property Modification in Keratin-Containing Surfaces

[0026] The keratin family of proteins are a family of structural fibrous proteins found in materials such as hair, wool, skin, nail, and teeth. Herein, for the sake of clarity and conciseness, the technology disclosed is described with reference to the modification of hair surface properties, but it is to be understood that the description translates similarly to other keratin-containing materials, such as the cosmetic modification of skin or nails. Accordingly, the technology disclosed is not intended to be limited to the implementations described with{00944416.DOCX }Page 7 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 references to the figures, and one or more modifications to the disclosed implementations resulting in alternative implementations relating to other keratin-containing surfaces will be apparent.

[0027] Broadly speaking, a hair property, such as a surface property or characteristic, is any property, characteristic, feature, and / or attribute related to one or more of the chemical, physical, health, or cosmetic nature of the hair. A surface property, for example, can be any cosmetically relevant feature of a keratin-containing material that can be affected by chemical modification of the first 20 µm in depth of the keratin-containing material. Accordingly, a “surface” refers to the outermost layers of a keratin-containing material, like hair, up to 20 µm in depth. Cosmetically relevant surface properties that can be modified by the disclosed system and methods can include, for example, hydrophobicity, surface energy, shine, smoothness, color, tone, intensity, thickness, absorption, frizz, moisture, elasticity, porosity, shape, density, stiffness, static charge, texture, and so on.

[0028] Hair damage can be defined by a degraded quality of one or more hair properties, including hair surface properties. Degradation of quality can be defined quantitatively, such as a particular percentage, differential, or shift increase or decrease in value from an industry / researcher defined value or range of values (see, for example, experimental results described herein that expand upon one or more approaches to quantify damaged hair quality). Degradation of quality may also be defined qualitatively, such as a classification of hair texture or color or an individual’s subjective assessment of a hair sample (e.g., ease of maintenance / styling, feel, confidence, or adherence to one or more personally defined preferences). In one example, damage may be loss of lipid, which contributes to commercially undesirable properties such as dryness, dullness, or frizziness.

[0029] Hair damage can be caused by several sources of weathering (and grooming) conditions. Certain sources of damage are difficult to prevent such as those caused by day-to- day mechanical friction and climate. Other sources of damage result from treatments that are highly popular with consumers, such as the physical and chemical processing of hair for styling purposes. Generally, the removal of the 18-MEA layer can occur with routine grooming (e.g., brushing, UV-degradation from sun, etc.) but it is significantly accelerated by chemical processing. This can include the use of permanent oxidative color, perming agents, straightening agents, and especially, bleach and hair lighteners. This damage can be observed directly by measuring the hydrophobicity of the hair surface before and after hair bleaching using a technique called dynamic contact angle; by this technique, one can assess the hydrophobicity of a surface by evaluating the extent to which water beads up when dropped{00944416.DOCX }Page 8 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 on the substrate. Hence, the ability to engage creatively with hair styling without the concern of irreversible damage to hair is highly desirable to a large market audience.

[0030] In another example, degradation of quality may be longevity of a treatment, such as color fastness (i.e., characterization of color resistance to fading or running) or a conditioning treatment (i.e., treatment of hair in an attempt to mimic the properties associated with lipids on the hair surface, thereby improving shine, moisture, feel, or tangle-resistance). Regarding longevity, a permanent treatment effect is one which lasts long enough to still produce a measurable effect after 50 or more standard washes that include the application of a shampoo, physical massaging, and warm water. A semi-permanent effect is one which lasts long enough to still produce a measurable effect after at least 12, but less than 50, standard washes. A temporary effect is one which does not last long enough to produce a measurable effect after 11 or fewer standard washes. A hair treatment refers to an application of a particular chemical formulation or physical technique onto the hair.

[0031] Herein, treatment with the technology disclosed refers to an application of the disclosed system onto a hair sample or other keratin-containing material. In many implementations, the treatment is applied to hair, thereby enabling an in situ reaction, or a reaction happening in the hair. In some implementations, the technology disclosed relates to orthogonal tuning of hair properties. An orthogonal property refers to a first property of a material, surface, or composition that can be changed without inducing a significant change in a second property of the material, surface, or composition. Significance of change is measured by the perceivability of an effect without the use of scientific equipment, such as a property or changed property that can be perceived by more than half of the total number of participants in a double-blind testing scenario.

[0032] One or more implementations of the disclosed system are configured to modify one or more surface properties of a keratin-containing surface via the use of a surface modifying compound. A surface modifying compound is a compound containing both a reactive handle and a surface modifying group configured to affect at least one cosmetic property of a keratin-containing surface, such as hair hydrophobicity, surface energy, shine, smoothness, color, thickness, or absorption. Herein, unless otherwise stated, it is to be understood that the terms “adhesion compound,” “catechol derivative,” “first compound,” and similar terminology are used synonymously. Similarly, unless stated otherwise, a “second compound” refers to a surface modifying compound, or a reactive compound configured to react with a surface modifying compound.{00944416.DOCX }Page 9 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2

[0033] The description herein is presented to enable the making and use of the technology disclosed. One or more modifications to the disclosed implementations will be apparent, and the general principles defined herein may be applied to other implementations and applications without departing from the spirit or scope of the technology disclosed. Many implementations of the technology disclosed can include one or more of the following features and / or components described in connection with additional implementations disclosed. In the interest of conciseness, the combination of features disclosed in this application are not individually enumerated and are not repeated with each base set of features. Thus, the technology disclosed is not intended to be limited to the implementations described with reference to the figures below but is to be accorded the widest scope consistent with the principles and features disclosed herein. The scope of the technology disclosed is defined by the appended claims.

[0034] Now, the technology disclosed will be described in further detail with reference to FIGs.1-6B. System and Composition Overview

[0035] Implementations including systems, methods, and compositions for modifying hair to achieve one or more long-lasting cosmetic changes are disclosed. Specifically, the compositions provide orthogonal property tuning of a wide variety of hair properties such as hydrophobicity, color, shine, feel, and manageability, on a semi-permanent to permanent timescale.

[0036] Many implementations of the disclosed compositions contain at least one catechol-bearing adhesion compound which can interact with the hair via non-covalent and covalent interactions and at least one hair-modifying compound which reacts (directly or indirectly) with the catechol-bearing compound. In one or more implementations of the disclosed methods, the catechol-bearing compound, including at least one catechol functional group or catechol derivative, increases the adhesion of the hair-modifying compound to the hair. Accordingly, the disclosed technology enables more permanent tuning of properties via the grafting of dyes, low surface energy compounds, lipids, film forming agents, and so on.

[0037] The disclosed invention avoids the use of harsh conditions for semi-permanent or permanent hair modification, such as strong oxidizing agents, thereby reducing damage to the hair structure.

[0038] FIG.1 illustrates an example hair surface modifying system or composition 100, according to many implementations of the technology disclosed. First, the individual{00944416.DOCX }Page 10 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 components of system 100 will be introduced, followed by a discussion of the interconnectedness of the components. In FIG.1, optional components of system 100, present in certain implementations of the technology disclosed, are illustrated with a dotted- line border, in contrast to components of system 100 illustrated with a solid-line border which are included in most implementations. Herein, an “optional” component refers to a component that may be present in specific implementations but is not a required component of system 100.

[0039] One or more implementations of a hair surface modifying system or composition 100, described with reference to FIG.1, include an adhesion compound 110 and a second compound 120. System 100 can optionally further include an additive 130, an initiator 140, and / or a crosslinker 150, or combination(s) thereof. The system 100 modifies, supplements, or otherwise affects one or more properties of hair, such as a surface property, to cause one or more cosmetic changes thereto. In one example, a surface property such as microscale surface roughness is modified to achieve increased gloss or improved feel (smoothness), or increased combability and mechanical damage-resistance by reducing strand-to-strand or strand-to-brush friction (i.e., increased lubrication). In another example, surface energy is modified to achieve increased gloss, reduced water sorption (and in turn, frizz-resistance), grease-resistance, reduced splaying (i.e., reduced split ends). In another example, surface color is modified to achieve coverage of gray hair, tonality change, or shade change. In another example, surface opacity is changed to achieve a lightening or blonding effect. In another example, surface thickness is modified to change the perceived density of hair. A user skilled in the art will recognize that these examples are provided for illustrative purposes and should not be considered limiting to the spirit or scope of the technology disclosed. Cosmetic changes resulting from a modified property of hair can be temporary, semi- permanent or substantially permanent. The system 100 provides orthogonal property tuning of a variety of hair properties, such as hydrophobicity, color, shine, feel, manageability, etc., or combinations thereof.

[0040] The adhesion compound 110 is able to bind to keratin-containing materials, such as hair, teeth, nails, skin and / or other keratin-containing materials. Features of the adhesion compound 110 that assist with binding to the keratin-containing materials can include a first structure 112 of the adhesion compound 110. In one example implementation, the structure 112 of the adhesion compound 110 can include a catechol-derivative.

[0041] The first structure 112 of the adhesion compound 110 further includes a first reactive handle 114, according to one implementation of disclosed system 100. The reactive{00944416.DOCX }Page 11 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 handle 114 is positioned at a location such that its reaction with another compound does not result in an increase in the degree of substitution in the aromatic ring of the catechol derivative. In one example, the first reactive handle 114 is polymerizable with another compound to form a polymer. In a further example, the adhesion compound 110 can be a monomer, oligomer, or polymer. In another example, the reactive handle 114 of the first structure is such that it can react and polymerize with the other compound. In a further example, the reactive handle 114 can include methacrylamide, acrylamide, methacrylate, acrylate, or other polymerizable handle. Additional details and / or information regarding the first reactive handle 114 are discussed below.

[0042] The first structure 112 of the adhesion compound 110 can also include a spacer 116 in another implementation. The spacer 116 is bound, at a first end, to the first reactive handle 114 and, at a second end, to another portion of the first structure 112 of the adhesion compound 110. In one example, the spacer 116 can be positioned between an aromatic ring of the first structure 112 and the reactive handle 114. The first structure 112 of the adhesion compound 110 and the adhesion compound 110 are further discussed below.

[0043] The hair surface modifying system 100 can also include a second compound 120. The second compound 120, in one or more implementations, can include a surface modifying component 126a and / or react with a surface modifying component 126b. The adhesion compound 110 binds to the keratin-containing material (e.g., hair) and polymerizes with the second compound 120 to affect a modification to one or more properties of the keratin- containing compound. One or more of the resulting modified hair properties can include a modification of the appearance of the treated hair, or another subjective and / or objective property of the hair that has been treated using the surface modifying system 100.

[0044] The second compound 120 includes a second structure 122 that further includes a second reactive handle 124. The second reactive handle 124 is such that the first and second reactive handles 114, 124 will interact when the adhesion compound 110 and the second compound 120 are combined. The interaction between the adhesion compound 110 and the second compound 120 can result in a bond formed therebetween, e.g., by polymerization. A stimulus can be applied to catalyze or otherwise assist in formation of the bond between the adhesion compound 110 and the second compound 120, such as between the first reactive handle 114 and the second reactive handle 124, causing the adhesion compound 110 and the second compound 120, or at least a portion(s) thereof, to be interconnected.

[0045] As previously introduced, the second structure 122 of the second compound 120 can include a surface modifying component 126a. Alternatively, or additionally, the second{00944416.DOCX }Page 12 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 compound 120 can be bound to and / or react with a surface modifying component 126b. In this embodiment, the second compound 120 acts as a bridge between the adhesion compound 110 and the surface modifying component 126b, allowing the surface modifying component 126b to be applied separately from the second compound 120. The surface modifying component 126a, 126b modifies a cosmetic property of the keratin-containing material, such as hydrophobicity, color, shine, feel, manageability, etc., or combinations thereof. The cosmetic modification(s) can be permanent or semi-permanent in nature, with the permanence being based on, at least, the interaction between the adhesion compound 110 and the keratin-containing compound to which the adhesion compound 110 is adhered.

[0046] Some implementations of the hair modifying system 100 of FIG.1 include one or more additive(s) 130. The additive(s) 130 can provide, supplement, modify or otherwise affect one or more characteristic of the hair modifying system 100 which may improve the system performance, usability, appearance, or other characteristic. Example additive(s) 130 can include one or more of an emulsifier 132, diluent 134, an opacifier 136 and / or other additives. The emulsifier 132 assists with efficacious mixing of immiscible components of the system 100. The diluent 134 assists with diluting the overall system 100 and / or components thereof. The dilution of the system 100, such as diluting a composition of the adhesion and second compounds 110, 120, can increase the volume of the system 100, alter a viscosity of the system 100, and / or alter other characteristics of system 100 such as improving one or more of the wetting, penetration, or spreadability of the system 100 to a keratin-containing material. The opacifier 136 can increase or decrease the opacity of the system 100, thereby increasing or decreasing the opacity of an applied color to hair, for example.

[0047] The hair modifying system 100 of FIG.1 includes an initiator 140 in some implementations. The initiator can assist with the interaction and interconnection processes between the adhesion compound 110 and the second compound 120. In one example, the initiator 140 can assist in the polymerization between the adhesion compound 110 and the second compound 120, which can include, or otherwise bind to, a surface modifying component 126a, 126b. Further discussion of the initiator 140 is provided below.

[0048] Certain implementations of the hair modifying system 100 of FIG.1 include a crosslinker 150. The crosslinker 150 can assist in linking two or more polymeric, oligomeric, or dimeric chains together. Further discussion of the crosslinker 150 is provided below.

[0049] One or more implementations of the disclosed systems, methods, and compositions (e.g., system 100) include the adhesion of a catechol derivative to hair or other{00944416.DOCX }Page 13 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 keratin-containing surfaces. The chemistry of catechol adhesion will now be described in further detail with reference to FIGs.2 and 3.

[0050] FIG.2 shows a schematic diagram of catechol adhesion to keratin-containing surfaces. Bonding motifs 203, 204, 205, 206, and 207 respectively model different possible non-covalent interactions between the catechol and keratin-containing surface (keratin surface 201) or oxidized keratin-containing surface (damaged keratin surface 202). A more detailed description of the binding mechanism and other binding chemistry considerations is omitted for the bonding motifs shown within FIG.2, as a user skilled in the art will be familiar with the associated processes and reactions thereof.

[0051] Bonding motif 203 illustrates a potential pi-pi stacking interaction between the catechol aromatic group and an aromatic side chain of a keratin amino acid of keratin surface 201, such as tyrosine. Bonding motif 204 illustrates a potential hydrogen bonding interaction between the catechol hydroxyl groups and hydrogen bonding side chain of a keratin amino acid of keratin surface 201, such as lysine. Bonding motif 205 illustrates a potential cation-pi interaction between the catechol aromatic ring and the cationic side chain of a keratin amino acid of keratin surface 201, such as arginine. In other implementations, the keratin amino acid is another amino acid other than tyrosine, lysine, or arginine.

[0052] Bonding motif 206 illustrates a potential metal ion-assisted catechol bonding to a damaged keratin surface 202. The damaged keratin surface 202 contains thiolate anion groups (i.e., SO3-) formed by oxidation of cysteine residues. The metal ion M++or M+++is coordinated with the hydroxyl groups of the catechol and the thiolate anions of the damaged keratin, thereby forming an adhesion-amplifying bridge between the vicinal hydroxyl groups of the catechol and the thiolate anions. Bonding motif 207 illustrates a potential hydrophobic interaction between the keratin-containing surface 201 and a catechol aromatic group. Bonding motifs 208 and 209 each respectively illustrate potential covalent bonding between the catechols and keratin-containing surface. As depicted within bonding motif 208, catechols may covalently bond with cysteine sulfhydryl groups in the keratin-containing surface via Michael addition. Alternatively, primary amine groups of keratin-containing surfaces may covalently bond to the catechol via a Schiff base reaction as shown in bonding motif 209.

[0053] FIG.3 shows a schematic diagram for the possible reaction pathways, i.e., schemes, 300A, 300B by which the adhesion catechol compound and a surface modifying compound may be linked without causing an increase in the degree of substitution of the aromatic ring of the adhesion catechol compound. The linkage between an adhesion catechol compound 301 and the surface modifying compound (such as surface modifying compounds{00944416.DOCX }Page 14 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 302, 307) may be direct, as depicted in reaction scheme 300A. In 300A, a stimulus 303 induces chemical conjugation between (i) the adhesion catechol compound 301 containing an optional spacer (denoted as R2 within adhesion catechol compound 301) and a reactive handle (denoted as R3 within adhesion catechol compound 301) and (ii) the first surface modifying compound 302 containing a second reactive handle (denoted as R4 within the first surface modifying compound 302). The first consequent structure 304, resulting from the adhesion catechol compound 301 and the first surface modifying compound 302 having been bound at their reactive handles, may be dimeric, oligomeric, or polymeric in nature.

[0054] Alternatively, the linkage between the adhesion catechol compound 301 and a surface modifying compound may be indirect, as depicted in reaction scheme 300B. In 300B, a stimulus 303 induces a chemical reaction between the reactive handle of the adhesion catechol compound 301 and a second reactive handle (denoted as R4 within additional reactant compound 305). The consequent structure 306, resulting from the adhesion catechol compound 301 and the additional reactant compound 305 having been bound at reactive handles R4 and R3, may be dimeric, oligomeric, or polymeric in nature. Second consequent structure 306 is then further reacted at a reactive handle R5 with a second surface modifying compound 307 containing a reactive handle R6. The consequent structure 308, resulting from linkage of the adhesion catechol compound 301 and the second surface modifying compound 307 linked via additional reactant compound 305. A number of stimuli may be used as stimulus 303, including stimuli of electromagnetic, chemical, or mechanical nature, and stimulus 303 need not be the same stimulus within reaction scheme 300A and 300B.

[0055] FIGs.4A, 4B, 5A and 5B illustrate respective example approaches 400a, 400b, 500a, 500b for applying a hair surface modifying system and / or composition, such as system 100 shown in FIG.1 or the one or more alternative implementations disclosed herein. Respective approaches 400a, 400b of FIGs.4A, 4B illustrate an example implementation in which a first compound and a second compound, such as the adhesion compound 110 and second compound 120 of FIG.1, are applied individually to a hair surface and bonded thereon. Respective approaches 500a, 500b of FIGs.5A, 5B illustrate another example implementation in which a first and a second compound, such as the adhesion compound 110 and second compound 120 of FIG.1, are combined and applied to a hair surface.

[0056] At operation 402 of the approaches 400a, 400b of FIGs.4A, 4B, a first compound having a first reactive handle is applied to hair. The first compound can be an adhesion compound, such as 110 of FIG.1, that binds to the hair.{00944416.DOCX }Page 15 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2

[0057] At operation 404, a second compound having a second reactive handle is applied to the hair. For example, the second compound can be the second compound 120 of FIG.1 and can further include (or be configured to bind to) a surface modifying component, such as 126a, 126b. As noted, each of the first and second compounds includes a respective reactive handle. The reactive handles of each of the first and second compounds are configured to react, so as to bond the first and second compounds together and interconnect them, such as in a manner described herein.

[0058] In certain implementations, at operations 406a, 406b, a third compound having a surface modifying group can be applied. Operations 406a, 406b are not included in other implementations (i.e., optional operations) as indicated by the dotted-line border of said components, in contrast to solid-line border components which are not optional. In FIG.4A, the third compound is optionally applied at an operation 406a to the already-applied first and second compound. In FIG.4B, the third compound is optionally applied at operation 406b to the already-bound first and second compounds. As described previously, the second compound can be configured or structured to link the first compound to a third compound that is a surface modifying component, such as 126b of FIG.1. In some instances, the third compound having a surface modifying group, such as surface modifying component 126b, may have one or more physical / chemical features that inhibits its ability to be otherwise directly linked or joined to the first compound. Examples of such physical / chemical features can include, steric hindrance, molecular weight of the surface modifying group, and other properties readily recognizable by a user skilled in the art.

[0059] At operation 408, the applied compounds are exposed to an external stimulus, such as stimulus 303 of FIG.3. The applied compounds can include the first and second compounds applied at operations 402, 404, and optionally the third compound applied at operation 406. The external stimulus can include light, heat, and / or other stimulus. The exposure to the external stimulus at operation 408 causes the first reactive handle of the first compound and the second reactive handle of the second compound to react and form at least a bond therebetween at operation 410. Additional discussion of the stimulus and bonding between the first and second compounds is discussed further herein.

[0060] At operation 412, at least one surface property of the hair is modified in response to the bonding between the first and second compounds. As previously discussed, in an example, the second compound can include a surface modifying component, such as 126a of FIG.1. The bonding of the first and second compounds thus causes the modification of a surface property of the hair. In another example, the surface modifying component can be{00944416.DOCX }Page 16 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 included in the third compound, such as 126b of FIG.1, that has the surface modifying group and this third compound binds to the second compound, which is in turn bound to the first compound, thus causing the modification of a surface property of the hair.

[0061] At operation 502 of FIGs.5A, 5B the first and second compounds having first and second reactive handles, respectively, are combined. As discussed, the first compound can be an adhesion compound, such as an adhesion catechol compound 110 of FIG.1. The second compound can include a surface modifying component, such as 126a of FIG.1 or bind to a surface modifying component, such as a third compound that includes a surface modifying group, such as shown at 126b of FIG.1.

[0062] At operation 504, the mixture of compounds is exposed to an external stimulus, such as stimulus 303 of FIG.3. As discussed, the external stimulus can include light, heat, chemical introduction or other stimulus. This causes the respective reactive handles of the compounds to react and form a bond between the first and second compounds at operation 506. Additional discussion of the bond formation between the first and second compounds and the stimulus is described herein with reference to certain implementations of the technology disclosed. In an example, the stimulus can cause the polymerization of the first and second compounds at operation 506.

[0063] At operation 508, the composition of compounds is applied to hair. In an example, the first compound can be an adhesion compound that binds to keratin-containing material, such as hair. In this manner, the first compound anchors or bonds the complex of the first and second compounds to the hair.

[0064] At operation 510a of FIG.5A, a third compound can optionally be applied. The third compound includes a surface modifying group, such as the surface modifying component 126b of FIG.1. In this example, the second compound interconnects the first and third compounds. At 510b of FIG.5B, the third compound can be optionally mixed with the combined first and second compounds prior to application to the hair at operation 508.

[0065] At operation 512, at least one surface property of the hair is modified in response to the bonding between the first and second compounds. As previously discussed, in an example, the second compound can include a surface modifying component, such as 126a of FIG.1. The bonding of the first and second compounds thus causes the modification of a surface property of the hair. In another example, the surface modifying component can be included in the third compound that has the surface modifying group, such as 126b of FIG.1, and this third compound binds to the second compound, which is in turn bound to the first compound, thus causing the modification of a surface property of the hair.{00944416.DOCX }Page 17 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 Composition for Tuning One or More Surface Properties of Keratinous Materials

[0066] As previously discussed, many implementations described herein involve a composition for tuning one or more surface properties of keratinous materials, such as hair. The one or more surface properties can be tuned for cosmetic effect(s), including coloring, lightening, glossing and / or other cosmetic properties of hair that will be readily apparent to users skilled in the art. The composition includes at least a first compound, such as the adhesion compound 110 of FIG.1. In an example, the first compound can include a catechol derivative of the structure (I), shown below:

[0067] The structure (I) includes an optional spacer R2 and a reactive handle R3, such as shown at 114 of FIG.1. Additionally, the composition includes a second compound, such as the surface modifying compound 120 of FIG.1, that has a second reactive handle. In response to a stimulus such as light, heat, mixing, and / or other, the first reactive handle of the first compound and second reactive handle of the second compound react with one another causing the formation of at least a bond between the compounds, such as by polymerization. This reaction may be covalent or noncovalent in nature and can result in a growing chain of molecules bearing multiple catechols. In some examples, this reaction refers to a radically mediated process such as free radical polymerization.

[0068] The second compound has a second structure, such as 122 of FIG.1, and can be structured such that it modifies at least one or more properties of the hair, such as imparting one or more desirable cosmetic effects. Alternatively, the second compound can have a second structure that is structured to react with a compound that modifies at least one or more properties of the hair, such as imparting one or more desirable cosmetic effects. The second compound or the compound the second compound reacts therewith, as previously described, can tune or modify one or more properties of the hair, including the color, hydrophobicity, gloss, dirt-resistance, and / or other cosmetic feature(s) of the hair. {00944416.DOCX } Page 18 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2

[0069] Chemical conjugation of a hair-modifying compound, such as the second compound, directly or indirectly to the catechol derivative improves the longevity of the cosmetic effect related to the hair-modifying compound. This is achieved in the absence of harsh conditions that are required for typical hair-modifying treatments. For example, strong base and oxidant treatments are commonly used to increase penetration of molecules of interest into the cortex of the hair where they become sterically trapped. In contrast, the adhesion of the technology disclosed, such as implementations involving system 100 of FIG. 1, results from multiple non-covalent and covalent interactions between a catechol group of the first compound and keratin of the hair in the surface layer or cuticle. As shown in FIG.2, non-covalent interactions can include, but are not limited, to hydrogen bonding, hydrophobic interactions, pi-pi stacking, and other non-covalent interactions readily recognizable to a user skilled in the art. Covalent interactions can include, for example, Michael addition and Schiff base formation. It is to be understood that the non-covalent and covalent interactions listed here are examples purely for illustrative purposes relating to one or more implementations of the technology disclosed and should not be considered limiting to the spirit or scope of the technology disclosed. The adhesion may optionally be further enhanced by pre-treatment of the hair with positively charged metal ions that can bridge interactions between the keratin and the catechol of the first compound via coordination.

[0070] In one implementation of the disclosed system, the first compound, such as an adhesion compound, and the second compound, such as a monomer configured to modify a surface property or configured to bind to another compound configured to modify a surface property, bond by a polymerization reaction, resulting in a polymeric structure. Polymeric structures comprising catechol side-groups or backbone components often have improved adhesion relative to other polymeric structures that possess no catechols. Thus, polymeric structures in which catechol-functionalized monomers are chained together with monomers possessing, or otherwise linked to, cosmetic property-modifying groups often demonstrate good durability achieving modifications to one or more cosmetic properties of the hair on an extended timescale. To create a polymeric structure, such as described herein with reference to implementations of the technology disclosed, catechol containing monomers may be directly copolymerized with surface modifying monomers. Alternatively, catechol containing monomers may be copolymerized with monomers possessing a reactive handle which then may, in turn, be reacted with a surface-modifying compound through post-polymerization modification. The reverse is also possible; surface modifying monomers may be copolymerized with reactive monomers which are subsequently reacted with catechols.{00944416.DOCX }Page 19 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 Another approach includes a polymerization initiator that is (i) functionalized with catechol and (ii) subsequently used to induce the polymerization of cosmetic property-modifying monomers, yielding surface modifying polymers with catechol end-functionalization. Yet another approach includes reactive pre-polymers containing catechol pendant groups and / or surface-modifying pendant groups to be tethered together at their reactive handles. Implementations including any of these approaches can be achieved in situ, before or after application to the hair.

[0071] Many implementations of the disclosed composition contain at least one adhesion compound, which increases adhesion of the resulting polymer to the hair, thereby improving the longevity of the treatment. The adhesion compound contains a reactive handle and an aromatic group with two or more alcohol groups. The adhesion compound adheres to the surface of the hair through non-covalent interactions, covalent interactions, or a combination of both. In one implementation, the reactive handle of the adhesion compound is a polymerizable handle. In a further implementation, the reactive handle is an acrylamide or meth(acrylamide). Examples of adhesion catechol compounds with acrylamide functionalities include, but are not limited to, dopamine acrylamide and dopamine methacrylamide. In other implementations, the reactive handle is not an acrylamide. Examples of adhesion catechol compounds with a non-acrylamide reactive handle include, but are not limited to: dopamine; norepinephrine; epinephrine L-3,4-dihydroxyphenylalanine (L-Dopa); esters of L-Dopa; gallic acid; poly(catechol) compounds such as tannic acid; EGCG, and so on; dihydrocaffeic acid; dihydroxycinnamic acid (caffeic acid); esters or caffeic acid or dihydrocaffeic acid, such as caffeic acid methyl ester; catechol-thiol; 2-chloro-3,4-dihydroxyacetophenone; 4- vinylcatechol; hydroxytyrosol; and esters of hydroxytyrosol such as oleuropein. Surface Modifying Compound

[0072] The disclosed composition contains at least one surface modifying compound. The surface modifying compound contains at least one reactive handle and a surface- modifying group. It may be reacted directly when the surface modifying compound is the second compound 120 of system 100. Alternatively, it may be reacted indirectly, when the surface modifying compound is component 126b of system 100, along with the adhesion compound. In some implementations, the surface modifying compound modifies the surface hydrophobicity, gloss, feel, lubrication, manageability, combability, frizz-propensity, color, blondeness, surface energy, thickness, and / or permeability to sunlight, water, and / or dyes.{00944416.DOCX }Page 20 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 Repairing Hair Damage with a Surface Modifying Compound: Polymerizable Handle

[0073] Many cosmetically desirable properties— for example, gloss, feel, lubrication, manageability, combability, or frizz-propensity— occur naturally in virgin (i.e., untreated by cosmetic hair treatments) hair, but these properties can become compromised when the outermost layer of the hair (the cuticle) is damaged. More specifically, these properties are compromised when the lipid coating, also referred to as the F-Layer, of the outermost layer is damaged. This damage may occur due to chemical damage, such as exposure to strong oxidants, alkalizing agents, or reducing agents; UV-catalyzed degradation, such as by sun exposure; mechanical damage, such as by brushing; as well as many other forms of hair damage readily recognizable to users skilled in the art. Accordingly, restoration of the hydrophobic F-Layer is a means by which properties such as gloss, feel, lubrication, manageability, combability, and frizz-propensity can be improved, especially in damaged hair. In some implementations, the surface modifying compound is configured to improve one or multiple of these properties of the hair surface compromised by prior damage to the F- Layer. In these implementations of the disclosed system including the surface modifying component, the system is configured to mimic the behavior of a healthy F-Layer. In further implementations, the reactive handle of the surface modifying compound configured to repair the F-layer function is a polymerizable handle.

[0074] Examples of such compounds include, but are not limited to: acrylic siloxanes; fluorinated acrylic monomers; PEG methacrylates; alkyl methacrylates; alkyl acrylates; and vinyl siloxanes. Examples of acrylic siloxanes include, but are not limited to: Acryloxy Terminated Ethylene oxide - Dimethylsiloxane-Ethyleneoxide ABA Block Copolymers; Acryloxypropyl T-structure Siloxanes; (Acryloxypropyl)methylsiloxane - Dimethylsiloxane Copolymers; (3-Acryloxy-2-hydroxypropoxypropyl) Terminated PolyDimethylsiloxanes; (3- Acryloxy-2-Hydroxypropoxypropyl)Methylsiloxane-Dimethylsiloxane Copolymer; Methacryloxypropyl Terminated Branched PolyDimethylsiloxanes; Methacryloxypropyl T- structure Siloxanes; (Methacryloxypropyl)methylsiloxane - Dimethylsiloxane Copolymers; and Methacryloxypropyl Terminated PolyDimethylsiloxanes. Examples of fluorinated acrylic monomers include, but are not limited to: 1H,1H,2H,2H-Heptadecafluorodecyl methacrylate; 1H,1H,5H-Octafluoropentyl methacrylate; 2,2,2-Trifluoroethyl acrylate; 2,2,2-Trifluoroethyl methacrylate; Hexafluoro-iso-propyl methacrylate; and Pentafluorophenyl acrylate. Examples of PEG methacrylates include, but are not limited to: Behenyl Polyethyleneglycol Methacrylate and Methyl Polyethyleneglycol Methacrylate. Alkyl methacrylates include, but{00944416.DOCX }Page 21 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 are not limited to, the following examples: behenyl methacrylate; cyclohexyl methacrylate; isotridecyl methacrylate; lauryl methacrylate; n-butyl methacrylate; octyl methacrylate; iso- decyl methacrylate; stearyl methacrylate; and tert-butyl methacrylate. Examples of alkyl acrylates include, but are not limited to: behenyl acrylate; ethyl acrylate; heptadecyl acrylate; iso-butyl acrylate; iso-decyl acrylate; lauryl acrylate; methyl acrylate; 2-ethylhexyl acrylate; n-butyl acrylate; 2-propylheptyl acrylate; stearyl acrylate; and tert-butyl acrylate. Examples of vinyl siloxanes include, but are not limited to: ^-MonoVinyl-MonoPhenyl-^- MonoHydride Terminated PolyDimethylsiloxane and MonoVinyl Functional PolyDimethylsiloxane - symmetric. Repairing Hair Damage with a Surface Modifying Compound: Post-Polymerization Modification

[0075] In other implementations, the surface modifying compound is (i) configured to repair the surface hair surface hydrophobicity or related property and (ii) reacted indirectly with the adhesion compound. In further implementations, the surface modifying compound is reacted with a coupled form of the second reactive compound and the adhesion compound. In further implementations, the coupled form is a copolymer. In another implementation, the reactive handle of the surface modifying compound may be a primary amine, an activated ester, a maleimide, a thiol, an azide, or vinyl sulfone.

[0076] Examples of amine functionalized surface modifying compounds include, but are not limited to: aminoethylaminopropylmethoxysiloxane - dimethylsiloxane copolymers; aminoethylaminopropylmethylsiloxane - dimethylsiloxane copolymers; aminopropyl terminated polydimethylsiloxanes; aminopropylmethylsiloxane - dimethylsiloxane copolymers, decylamine; heptylamine; hexylamine; nonylamine; octylamine; oleylamine; pentylamine; stearylamine; and 1,2-Distearoyl-sn-glycero-3-phosphoethanolamine. Examples of activated ester surface modifying compounds include, but are not limited to: PEG NHS ester; Oleic-NHS ester; and DSPE-PEG-NHS. Examples of maleimide surface modifying compounds include, but are not limited to: MS(PEG)4, TMM(PEG)12 (Methyl-PEG12 ) 3- PEG4-maleimide; 1,2-distearoyl-sn-glycero-3-phosphoethanolamine-N- [maleimide(polyethylene glycol)-2000]; Alkyl(C8) maleimide; Alkyl(C10) maleimide; Alkyl(C12) maleimide; Alkyl(C18) maleimide; DSPE-PEG8-Mal; and DSPE-PEG12-Mal. Examples of thiol functionalized surface modifying compounds include, but are not limited to: tert-Nonanethiol; 3-Mercaptopropionic Acid Methyl Ester; tert-Dodecanethiol; n- Propylmercaptan, n-Dodecyl mercaptan; n-Octyl mercaptan; 1-octadecanethiol; 11-{00944416.DOCX }Page 22 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 Mercapto-1-undecanol; 1H,1H,2H,2H-Perfluorodecanethiol; and 2-Ethyl-1-hexanethiol. Examples of alkyne functionalized surface modifying compounds include, but are not limited to: DSPE-PEG-Azide and DSPE-PEG-DBCO. Examples of vinyl sulfone functionalized surface modifying compounds include, but are not limited to: mPEG5K-Vinyl sulfone; DSPE-PEG-Vinylsulfone; ethyl vinyl sulfone; and DSPE-PEG-Vinylsulfone. Modifying the Color of the Hair Surface with a Surface Modifying Compound: Polymerizable Dye

[0077] In some implementations, the surface modifying compound is configured to modify the color of the hair surface. In such implementations, the reactive handle of the surface modifying compound configured to modify the color of the hair surface is polymerizable. Examples of color-modifying surface modifying compounds having a polymerizable handle include, but are not limited to, (meth)acrylate visible and fluorescent dyes. Examples of (meth)acrylate visible dyes include, but are not limited to: disperse red 1 acrylate; disperse red 1 methacrylate; disperse red 13 methacrylate; and disperse yellow 7 methacrylate. Examples of (meth)acrylate fluorescent dyes include, but are not limited to: 2- Naphthyl methacrylate; 9-Anthracenylmethyl methacrylate; Acryloxyethyl thiocarbamoyl Rhodamine B; Fluorescein dimethacrylate; Fluorescein O-methacrylate, Fluorescein O- acrylate, Methacryloxyethyl thiocarbamoyl rhodamine B; Nile Blue Acrylamide; and Nile Blue Methacrylamide. Modifying the Color of the Hair Surface with a Surface Modifying Compound: Post- Polymerization Modification

[0078] In other implementations, the reactive handle of the color modifying compound is not polymerizable. Examples of color-modifying compounds with non-polymerizable reactive handles include, but are not limited to: “Reactive Dyes”; metal ions; amine functionalized dyes; activated-ester dyes; maleimide dyes; azide-functionalized dyes; or isothiocyanate dyes.

[0079] Examples of Reactive Dyes include, but are not limited to: Reactive Black 5; Reactive Black 8; Reactive Blue 4; Reactive Blue 5; Reactive Blue 13; Reactive Blue 14; Reactive Blue 19; Reactive Blue 19; Reactive Blue 21; Reactive Blue 74; Reactive Blue 104; Reactive Blue 160; Reactive Blue 171; Reactive Brown 2; Reactive Brown 9; Reactive Green 19; Reactive Orange 1; Reactive Orange 5; Reactive Orange 16; Reactive Red 1; Reactive Red 2; Reactive Red 3; Reactive Red 11; Reactive Red 11; Reactive Red 15; Reactive Red{00944416.DOCX }Page 23 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 23; Reactive Red 88; Reactive Red 108; Reactive Red 120; Reactive Red 141; Reactive Violet 2; Reactive Yellow 1; Reactive Yellow 2; Reactive Yellow 3; Reactive Yellow 4; Reactive Yellow 17; Reactive Yellow 18; Reactive Yellow 81; Reactive Yellow 86; and Reactive Yellow 135.

[0080] Examples of metal ions include, but are not limited to: Cobalt(II) nitrate; Copper(II) nitrate; Iron(III) chloride; Manganese(III) acetate; Nickel(II) nitrate; Titanium(IV) chloride; Vanadium(III) chloride; and Vanadium(IV) sulfate. Examples of amine dyes include, but are not limited to: acridine yellow G; acriflavine; neutral red; bismarck brown R; bismarck brown Y; chrysoidine R; chrysoidine Y; acid fuchsine; pararosaniline; azure C; thionine; and toluidine blue. Examples of activated-ester dyes include, but are not limited to: CF™ 647 succinimidyl ester; CF™ 568 succinimidyl ester; CF™ 568 succinimidyl ester; and Atto 488 NHS ester. Examples of maleimide dyes include, but are not limited to: Cyanine5 Maleimide; Fluorescein-5-Maleimide; Alexa Fluor™ 488 C 5 Maleimide; and AZDye™ 647 Maleimide. Examples of azide dyes include, but are not limited to: 3-Azido-7- hydroxycoumarin; 5-FAM-Azide; 5-FAM-Azide; 5 / 6-Carboxyrhodamine 110-PEG^-Azide; 5-TAMRA-Azide; 5 / 6-TAMRA-PEG^-Azide; 6-FAM-Azide; AF488-Azide; AF488-Picolyl- Azide; AF546-Azide; AF546-Picolyl-Azide; AF555-Azide; AF555-Picolyl-Azide; AF594- Azide; AF594-Picolyl-Azide; AF647-Azide; AF647-Picolyl-Azide; Azide - BDP-FL; Cy3- Azide; Cy5-Azide; Cy5-Azide; Cy5.5-Azide; Picolyl-Azide-5 / 6-FAM; Picolyl-Azide-Cy7; Picolyl-Azide-Sulfo-Cy3; Picolyl-Azide-Sulfo-Cy5; Picolyl-Azide-Sulfo-Cy5; and Sulfo- Cy3-Azide. Examples of isothiocyanate dyes include, but are not limited to: Fluorescein Isothiocyanate, Tetramethylrhodamine-5-isothiocyanate, and Rhodamine B isothiocyanate. Linker Molecules

[0081] In some implementations of the disclosed composition, the second compound is not itself a surface modifying compound, but is configured to react with both the adhesion compound and an additional surface modifying compound. In further implementations, the second compound reacts with the adhesion compound through a polymerizable handle. Examples of second compounds configured (i) to react with the adhesion compound through a polymerizable handle and (ii) to react further with the surface modifying compound include, but are not limited to: amine acrylates, alkyne acrylates, or activated ester acrylates. Amine acrylates include, but are not limited to: 2-(Diethylamino)ethyl acrylate; 2- (Diethylamino)ethyl methacrylate; 2-(Dimethylamino)ethyl acrylate; 2-(Dimethylamino)ethyl methacrylate; 2-Aminoethyl methacrylate hydrochloride; allylamine; and N-(3-{00944416.DOCX }Page 24 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 Aminopropyl)methacrylamide hydrochloride. Alkyne acrylates include, but are not limited to: N-propargylacrylamide; propargyl acrylate; propargyl methacrylamide; propargyl methacrylate. Activated ester acrylates include, but are not limited to: Acrylic acid N- hydroxysuccinimide ester; Methacrylic acid N-hydroxysuccinimide ester; Pentafluorophenyl methacrylate; and Pentabromophenyl methacrylate. Opacifying Agents

[0082] In certain implementations, the composition may include one or more opacifying agents. Specifically, the opacifying agent may be an inorganic or organic nanoparticle between 1-500 nm that complexes with the catechol and confers opaqueness to the coating. Examples of opacifiers include, but are not limited to: nanoparticles of aluminum oxide; apigenin; Copper; Zinc Oxide Quantum Dots; Gold Nanosheets; Hesperidin; Silicon Quantum Dots; Rutin; Silicon dioxide; Silver; Titanium dioxide; Zinc oxide; and Zirconium oxide. Initiators

[0083] In one or more implementations, the composition may include one or more initiators. The initiator initiates the polymerization process between the adhesion compound and the second compound, wherein the second modifying compound is either a surface modifying compound or compound configured to react with a surface modifying compound. In some implementations, the initiator is of a type that generates a radical upon heating (thermal initiator) or light treatment (photoinitiator).

[0084] Examples of thermal initiators include, but are not limited to: 1,1-Bis(tert- butylperoxy)-3,3,5-trimethylcyclohexane; 1,1-Bis(tert-butylperoxy)cyclohexane; 1,1-Bis(tert- butylperoxy)cyclohexane; 2,2-Azobis(2,4-dimethylvaleronitrile) (AIBN); 2,2-Bis(tert- butylperoxy)butane; 2,4-Pentanedione peroxide; 4,4'-Azobis(4-cyanovaleric acid); Benzoyl peroxide; Cumene hydroperoxide; Cyclohexanone peroxide; Dicumyl peroxide; Lauroyl peroxide; Peroxyacetic acid; Potassium persulfate; tert-Amyl peroxybenzoate; tert-Butyl peroxyacetate; tert-Butyl peroxide; tert-Butylperoxy isopropyl carbonate; 1,1,7,7- Tetramethyl-1,3,5-triazacyclohexane. Examples of photoinitators include, but are not limited to, 2,2-Diethoxyacetophenone; 2,2-Dimethoxy-2-phenylacetophenone; 2-Benzyl-2- (dimethylamino)-4'-morpholinobutyrophenone; 2-Chloroanthraquinone-9-one; 2- Ethylanthraquinone; 3,3',4,4'-Benzophenonetetracarboxylic dianhydride, sublimed; 3'- Hydroxyacetophenone; 3-Hydroxy-2-methylpropiophenone; 3-Hydroxybenzophenone; 3-{00944416.DOCX }Page 25 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 Hydroxyphenyl phenyl ketone; 4-(3-Hydroxypropoxy)benzophenone; Lithium phenyl-2,4,6- trimethylbenzoylphosphinate; 2^hydroxy-2-methylpropiophenone; 4,4'- Bis(dimethylamino)benzophenone; 4,4'-Dihydroxybenzophenone; 4,4'- Dihydroxybenzophenone; 4,4'-Dimethoxybenzil; 4,4'-Dimethoxybenzophenone; 4- Benzylphenyl; 4-Hydroxy-2-methylpropiophenone; 4-Hydroxybenzophenone; 4- Hydroxyphenyl phenyl ketone; 4-Methylbenzophenone; 4-Morpholinobenzophenone; 4- Phenoxyacetophenone; 4-Thioxanthen-9-one; Acetophenone; Anisoin; Anthraquinone; Anthraquinone-2-sulfonic acid, sodium salt monohydrate; Benzil; Benzoin ethyl ether; Benzoin isobutyl ether, tech.; Benzoin methyl ether; Benzoin, sublimed; Benzophenone; Benzophenone-1-Hydroxycyclohexyl phenyl ketone; Camphorquinone; Cumylperoxycyclohexane(trifluoroacetylperoxy)cyclononane; Diethylbenzene; Diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide / 2-Hydroxy-2-methylpropiophenone, 50 / 50 blend; Ethyl 4-(dimethylamino)benzoate; F420; Methylbenzoylformate; 2-Methyl-4-(1- methyl-2-morpholinopropiophenone; 2-Methyl-4'-(methylthio)-2-morpholinopropiophenone; 2-Methyl-4'-(trimethylsilyl)-2-morpholinopropiophenone; Triarylsulfonium hexafluorophosphate salts, mixed, 50% in propylene carbonate; and Triarylsulfonium hexafluoroantimonate salts, mixed, 50% in propylene carbonate. In some implementations, the initiator is an azo initiator having an azo group of the structure (R-N=N-R'). Examples of azo initiators include, but are not limited to: 1,1’-azobis(cyclohexane-1-carbonitrile); 2,2’- azobis(2-methylbutyronitrile); 2,2’-azobis(2-methylpropionamidine)dihydrochloride; 2,2’- azobis(2-methylpropionitrile); 2,2’-azobis(4-methoxy-2,4-dimethylvaleronitrile); 2,2’- azobis[2-(2-imidazolin-2-yl)propane]; 2,2’-azobis[2-(2-imidazolin-2- yl)propane]dihydrochloride; 2,2’-azobis[2-methyl-n-(2-hydroxyethyl)propionamide]; 2,2’- azobis(n-butyl-2-methylpropionamide); 4,4’–azobis(4–cyanovaleric acid); and dimethyl 2,2’- azobis(2-methylpropionate). Crosslinkers

[0085] In other implementations, the composition may include one or more crosslinkers. The crosslinker is a component that links two or polymeric, oligomeric, or dimeric chains together. The crosslinker contains two or more reactive or polymerizable handles. In some implementations, these reactive or polymerizable handles are equivalent or homobifunctional. In other implementations, the crosslinker is of the form of a compound containing two or more (meth)acrylates, two or more (meth)acrylamides, two or more vinyl groups, two or more thiols, two or more allyl groups, two or more epoxy groups, two or more activated{00944416.DOCX }Page 26 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 esters, or two or more amines. In yet other implementations, the second compound configured to react with the adhesion compound and surface modifying compound may also be a crosslinker.

[0086] Examples of crosslinkers containing two or more (meth)acrylates include, but are not limited to: 1,3-butanediol diacrylate; 1,4-butanediol diacrylate; 1,6-hexanediol diacrylate; 9-(acryloyloxy)nonyl acrylate; di(ethylene glycol) diacrylate; ethylene glycol diacrylate; glycerol 1,3-diglycerolate diacrylate; neopentyl glycol diacrylate; poly(ethylene glycol) diacrylate; poly(propylene glycol) diacrylate; polycaprolactone diacrylate; tetra(ethylene glycol) diacrylate; tri(ethyleneglycol) diacrylate, glycerol propoxylate (1po / oh) triacrylate; trimethylolpropane ethoxylate triacrylate; trimethylolpropane propoxylate triacrylate; trimethylolpropane triacrylate; di(trimethylolpropane) tetraacrylate and pentaerythritol tetraacrylate; methacryloxypropyl-terminated polydimethylsiloxane; 1,3-bis (3- methacryloxypropyl) tetrakis(trimethylsiloxy)disiloxane; (3-acryloxy-2- hydroxypropoxypropyl) terminated polydimethylsiloxane; (methacryloxypropyl)methylsiloxane] - dimethylsiloxane copolymer; (methacryloxypropyl)methylsiloxane, homopolymer; (acryloxypropyl)methylsiloxane homopolymer; (acryloxypropyl) methylsiloxane] - dimethylsiloxane copolymer; and (3- acrloxy-2-hydroxypropoxypropyl) methylsiloxane]- dimethylsiloxane copolymer. Examples of crosslinkers containing two or more acrylamides include, but are not limited to: N,N^-(1,2- Dihydroxyethylene)bisacrylamide and N,N^-Methylenebis(acrylamide).

[0087] Examples of crosslinkers containing two or more vinyl groups include, but are not limited to: Dimethylsiloxane-vinylmethylsiloxane – (Propylene Oxide – Ethylene Oxide) Block Copolymers; Vinyl Terminated Diethylsiloxane - Dimethylsiloxane Copolymers, Vinyl Terminated Diphenylsiloxane-Dimethylsiloxane Copolymers; Vinyl Terminated Ethylene-Siloxane Copolymer Fluids; Vinyl Terminated Nonafluorohexylmethylsiloxane – Dimethylsiloxane Copolymer; Vinyl Terminated PolyDimethylsiloxanes; Vinyl Terminated TrifluoropropylMethylsiloxane - Dimethylsiloxane Copolymer; VinylMethylsiloxane - Dimethylsiloxane Copolymers, trimethylsiloxy terminated; VinylMethylsiloxane – Dimethylsiloxane copolymer, hydride terminated; Vinylmethylsiloxane Homopolymers; VinylMethylsiloxane Terpolymers, 1,4-butanediol divinyl ether; diethylene glycol divinyl ether; 1,4-divinyl-1,1,2,2,3,3,4,4-octamethyltetrasilane; and Tri(ethylene glycol) divinyl ether.

[0088] Examples of crosslinkers containing two or more thiol groups include, but are not limited to: 2,3-dimercapto-1-propanesulfonic acid; dimercaprol; propane-1,3-dithiol;{00944416.DOCX }Page 27 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 dithiothreitol; Trimethylolpropane tris(3-mercaptopropionate); Pentaerythritol tetrakis(3- mercaptopropionate); and 2,2^-(Ethylenedioxy)diethanethiol. Examples of crosslinkers containing two or more allyl groups include, but are not limited to: Pentaerythritol allyl ether; Allyl ether; 1,3,5-Triallyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione; Allyl disulfide; and Allyl sulfide.

[0089] Examples of crosslinkers containing two or more epoxy groups include, but are not limited to: Poly(glycidyl methacrylate); Poly(ethylene glycol) diglycidyl ether; and 1,4- Butanediol diglycidyl ether. Examples of crosslinkers containing two or more activated esters include, but are not limited to: EGS (ethylene glycol bis(succinimidyl succinate)); DST (disuccinimidyl tartrate); Sulfo-EGS (ethylene glycol bis(sulfosuccinimidyl succinate)); TSAT (tris-(succinimidyl) aminotriacetate); DMP (dimethyl pimelimidate); DMS (dimethyl suberimidate); and Bis(pentafluorophenyl) carbonate. Examples of crosslinkers containing two or more amines include, but are not limited to: 2,2^-(Ethylenedioxy)bis(ethylamine); 1,11-Diamino-3,6,9-trioxaundecane; Tris(3-aminopropyl)amine; tris(2-aminoethyl)-amine; diethylenetriamine; and Poly(ethylene glycol) bis(3-aminopropyl) terminated.

[0090] In other implementations, the crosslinker is heterobifunctional in nature. Examples of heterobifunctional crosslinkers include, but are not limited to: N-^- maleimidopropyl-oxysuccinimide ester; 2,6-Difluorophenyl pentafluorophenyl adipate; 2,6- Difluorophenyl pentafluorophenyl decanedioate; Poly(pentachlorophenyl methacrylate-co- glycidyl methacrylate); Poly[(phenyl glycidyl ether)-co-formaldehyde]; Allyl glycidyl ether; Allyl methacrylate; and Maleimide-PEG12-succinimidyl ester. Emulsifiers

[0091] Certain implementations of the disclosed composition include one or more emulsifiers. An emulsifier is an additive which helps immiscible components mix together. The emulsifier contains both hydrophilic and hydrophobic functionalities. The emulsifier plays a crucial role in preserving the stability and uniformity of the formulation. In some implementations, the emulsifier is an oil-in-water emulsifier, water-in-oil emulsifier, synthetic emulsifier, or natural emulsifier. Examples of oil-in-water emulsifiers include, but are not limited to: glycol stearate; glyceryl stearate; glyceryl stearate se; peg-8 propylene glycol cocoate; peg-100 stearate; polyglyceryl-4 oleate; and stearamide AMP. Examples of water-in-oil emulsifiers include, are not limited to: glyceryl caprate; methoxy peg-22 / dodecyl glycol copolymer; peg-7 hydrogenated castor oil; and polyglyceryl-2 dipolyhydroxy stearate. Examples of synthetic emulsifiers include, but are not limited to: alkyl dimethicone{00944416.DOCX }Page 28 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 copolyols; ammonium lauryl sulfate; dimethicone copolyols; poly(acrylic acid); polysorbate 20 (polyoxyethylene (20) sorbitan monolaurate); polysorbate 40 (polyoxyethylene (20) sorbitan monopalmitate); polysorbate 60 (polyoxyethylene (20) sorbitan monostearate); polysorbate 80 (polyoxyethylene (20) sorbitan monooleate). Examples of natural emulsifiers include, but are not limited to: glycine soja sterols; hydrogenated lecithin; hydrogenated lecithin; palm kernelamide DEA; and sodium cocamidopropyl pg-dimonium chloride phosphate. Diluents

[0092] Many implementations of the disclosed composition include one or more diluents. A diluent is an additive used to dilute the components of the formulation. In some implementations, the diluent is added to reduce the concentration of the composition, change the viscosity, or improve wettability of the substrate. Examples of diluents include, but are not limited to: 1,2-hexanediol; 1,3-propanediol; 1,5-pentanediol; 1,6-hexanediol; 1-propanol; 1-tetradecene; 2-(2-ethoxyethoxy)ethyl acetate; hexadecan-1-ol, benzyl benzoate; bis(2- ethylhexyl) phthalate; di(propylene glycol) methyl ether acetate; diacetin; dibutyl phthalate; dimethyl glutarate; dimethyl phthalate; dimethyl sulfone; dimethyl succinate; dipropylene glycol; dipropylene glycol monomethyl ether; dodecamethylcyclohexasiloxane (d6); decamethylcyclopentasiloxane (d5); ethanol; ethyl laurate; ethylene carbonate; glycerol; shea butter ; water, acetone, dimethyl formamide, and dimethyl sulfoxide. Example Use Cases and Objective Indicia of Non-Obviousness and Novelty

[0093] The composition is applied to the hair for the purpose of modifying one or more surface properties. The composition is activated via a stimulus that induces a reaction between (i) the adhesion compound containing a first reactive handle and (ii) a second compound containing a second reactive handle. The stimulus may be applied before or after application to the hair. In some implementations, the second compound includes a surface modifying group. In other implementations, the reaction between the adhesion compound and second compound results in the formation of a polymer or network. In further implementations, these compounds are copolymerized, yielding a copolymer. In another implementation, the adhesion compound is allowed to polymerize before addition of the second compound, yielding a pseudo block copolymer.

[0094] In one implementation, the second compound does not include a surface modifying group, but instead has a third reactive group that can react with a surface{00944416.DOCX }Page 29 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 modifying compound. The reaction between the third reactive group in the second compound and the surface modifying compound may occur simultaneously with the reaction between the adhesion compound and the second compound. Alternatively, the reaction between the third reactive group in the second compound and the surface modifying compound may occur in a separate step from the reaction between the adhesion compound and the second compound. In some implementations, the reaction between the adhesion compound and second compound results in the formation of a copolymer. In further implementations, the surface modifying compound reacts with the second compound in the pre-formed polymer in a post-polymerization reaction, forming a covalent link between the polymer and the surface modifying compound. In other one or more implementations, the surface modifying compound is inorganic in nature, and bonds non-covalently to the polymer inducing a change in a cosmetic property. This cosmetic property can be color or opacity, for example.

[0095] One or more implementations disclosed herein include a process of “activating” the composition, or inducing the chemical reaction between the adhesion compound and second compound by way of a stimulus (e.g., light, heat, chemical introduction, or some combination thereof) before application of the composition to the hair. In other implementations, the activation occurs after application to the hair.

[0096] In one example implementation, the adhesion compound and second compound with are packaged in separate containers. The separate containers are mixed prior to application to the hair. In another implementation, the separate containers are applied consecutively to the substrate. In many implementations, the pH of the combined composition does not exceed 8, and more preferably, falls in the range of 5.5-7.5. In some implementations, the combined molar concentration of the adhesion compound and second compound is 0.1-3.0 M, and more preferably falls in the range of 1.0-2.0 M. In some implementations, the molar percentage of adhesion compound to adhesion compound and second compound is 1%-99%, and more preferably falls in the range of 5-50%. In some implementations, the composition includes an initiator wherein the initiator is present at a molar percentage of 0.001-20% relative to the adhesion compound and second compound, and more preferably the initiator is present at a molar percentage of 0.5-10 mol% relative to the adhesion compound and second compound.

[0097] In some implementations, the applied stimulus is of chemical nature. In one implementation, the chemical stimulus involves addition of a catalyst to the composition. In another implementation, the stimulus is in the form of an electromagnetic wave or heat. Preferably, the electromagnetic wave has a wavelength of 300nm or longer, and more{00944416.DOCX }Page 30 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 preferably the wavelength is longer than 340nm and shorter than 10µm. The electromagnetic wave can be in the UV, visible or infrared region. Preferably, a stimulus in the form of heat is characterized by a temperature of 30^-200^, and more preferably falls in the range of 30^-60^. In one implementation, the heat is applied to the composition by direct or indirect contact with the surface of a hot plate. In one implementation, a styling tool provides the heat source as stimulus. In another implementation, the heat is applied via a device that produces hot air, such as a hair dryer. In yet another implementation, the heat is derived from human body temperature and is trapped by use of a thermally insulating material. In a further implementation, this thermally insulating material is a thermal bonnet.

[0098] The composition may be applied as a solution, suspension, aerosol, paste, cream, or gel. In one implementation, the composition is applied to the keratin-containing surface by spraying. In another implementation, the composition is applied to the keratin-containing surface by air brush. In a further implementation, the composition is applied to the keratin- containing surface by massaging. In another implementation, the composition is applied to the keratin-containing surface by painting or brushing. In some implementation, the keratin- containing material is teeth, skin, or nails. In many implementations, the keratin-containing material is hair.

[0099] In some implementations, the composition is applied to a keratin-containing surface after a pre-treatment. In one implementation, the pre-treatment consists of treating a keratin-containing surface with a solution of inorganic ions configured to improve the adhesion of the catechol compounds via a bridging interaction. In another implementation, the pre-treatment consists of treating a keratin-containing surface with a swelling agent configured to improve the penetration of the catechol compounds within the superficial. The swelling agent can be urea, but a number of alternative swelling agents may also be used.

[0100] In some implementations, the composition is configured to reduce the penetrability of the surface to harmful UV rays. For example, these implementations may include a surface modifying compound that is configured to absorb UV radiation. Suitable compounds include UV-absorbing (meth)acrylates such as 2-(2’-Methacryloxy-5’- methylphenyl)benzotriazole, benzyl acrylate, Dicyclopentenyloxyethyl acrylate, 4- Methacryloxy-2-hydroxybenzophenone, Cinnamyl methacrylate, phenyl methacrylate, 2- phenylethyl acrylate, 2-phenylethyl methacrylate, or phenyl acrylate. The UV-absorbing agent may also be an additive such as aminobenzoic acid, 2-(2-Hydroxy-5-tert- octylphenyl)benzotriazole, avobenzone, benzocaine, benzophenone-4, dioxybenzone, esculin,{00944416.DOCX }Page 31 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 ferulic acid, green tea extract, octinoxate, octylmethoxycinnamate, octisalate, octocylene, oxybenzone, padimate O, titanium dioxide, zinc oxide, et cetera.

[0101] In other implementations, the composition is configured to increase lubrication or feel of the surface. For example, these implementations may include a surface modifying compound that is configured form a smooth film or coating that reduces microscale surface roughness. Examples of surface modifying compounds configured to achieve a lubricating effect by reducing surface roughness include acrylic siloxanes; PEG methacrylates; alkyl methacrylates; alkyl acrylates; vinyl siloxanes, or other as previously described. In another implementation, the composition is configured to reduce water sorption or frizzing of the hair. For example, this implementation may include a surface modifying compound of hydrophobic nature, such as an acrylic siloxane; fluorinated acrylic monomers; PEG methacrylate; alkyl methacrylate; alkyl acrylate; vinyl siloxane; or other as previously described.

[0102] In another implementation, the composition is configured to increase shine or gloss of the surface. For example, this implementation may include a surface modifying compound of high refractive index. In addition, the surface modifying compound may be configured to form a smooth film or coating that enhances shine by reducing microscale roughness, and in turn, diffuse reflectance or scattering associated with dull appearance. Reactive silicones, for example, are particularly well-suited for this use as they are both high in refractive index and adept at forming smooth coatings on a microscale. In another implementation, the composition is configured to change the thickness of the surface. For example, the implementation may include an additive in the form of microfibers which may covalently or non-covalently bind to the adhesion compound. These fibers may, for example, be comprised of keratin, silk, polyester, polyamide (nylon), plant material, or other. In a further implementation, the composition is configured to change the whiteness of the surface. For example, the implementation may include an additive in the form of an opacifier such as a nanoparticle of aluminum oxide; apigenin; Copper; Zinc Oxide Quantum Dots; Gold Nanosheets; Hesperidin; Silicon Quantum Dots; Rutin; Silicon dioxide; Silver; Titanium dioxide; Zinc oxide; or Zirconium oxide.

[0103] In further implementations, the composition is configured to change the surface energy of the surface, such as to reduce grease build-up in hair or inhibit the efflux of cosmetic agents within the hair, such as dyes or whitening agents. For example, the implementation may include a surface modifying agent of oleophobic and hydrophobic nature. Examples of suitable surface modifying agents include functionalized siloxanes and{00944416.DOCX }Page 32 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 fluorinated structures such as fluorinated acrylic monomers, acrylic siloxanes, or vinyl siloxanes. In another implementation, the composition is configured to achieve more than one of the previous cosmetic changes. For example, this may be achieved by combining two or more of the described surface modifying compounds, additives, or both. Modification of Target Surface Properties of Hair Without Compromising Other Secondary Cosmetic Properties

[0104] The technology disclosed addresses a long-standing need for a platform capable of modifying an array of hair properties in a semi-permanent or permanent manner with reduced damage and toxicity, demonstrated by market demand as well as a growing body of scientific evidence from research conducted by the health and medicine sectors. Unlike oxidatively polymerized catechol systems that yield brown or black results, the technology disclosed yields a colorless or color-tunable result with similar longevity. Further, the system does not compromise any secondary cosmetic properties at the expense of the property of interest, as compared to the reduced surface feel in oxidatively polymerized catechol systems, poly(catechol styrene) usage, and poly(dopamine methacrylamide-co-methylmethacrylate) usage. The disclosed system also demonstrates improved longevity relative to alternatives like poly(catechol styrene) and poly(dopamine methacrylamide-co-methylmethacrylate) which can be readily removed by one washing cycle with shampoo.

[0105] The technology disclosed also affords a means to tune multiple surface properties at once with complete orthogonality. Table 1, provided below, summarizes the behavior of three example catechol systems evaluated for adhesion, feel and color on equivalent hair sources. Adhesion of the systems was evaluated by direct visual assessment in the case of the colored system (catechol, base, and / or oxidant) and by visual assessment following catechol staining with iron trichloride in the case of the naturally colorless systems (poly(catechol styrene) and poly(dopamine methacrylaide-co-methylmethacrylate)).{00944416.DOCX }Page 33 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 TABLE 1

[0106] After one wash, only catechol, base, and / or oxidant system could be visualized, suggesting the removal of the other two systems by washing, and in turn, poor adhesion. The feel and color immediately after treatment were also qualitatively evaluated for each system. Feel was assessed by running one’s fingers through the untreated and treated tress multiple times. All three treated tresses demonstrated cosmetically undesirable changes in feel relative to the pre-treatment tresses. The catechol, base, and / or oxidant system demonstrated increased roughness whilst the other two systems were stiffened relative to the pre-treatment tresses. Color was assessed visually. Hair treated with the catechol, base, and / or oxidant system became dark brown or black regardless of starting color following treatment whilst the other two systems demonstrated no visible change in color. Durable Restoration of Surface Hydrophobicity

[0107] Damaged hair (for example, hair that is damaged by lightening techniques commonly referred to as hair bleaching) is characterized by a reduction in surface lipids, yielding increased hydrophilicity, frizz, dullness, and breakage / splitting potential. Repair of the damaged hair surface can be achieved by coating the hair with weakly bound oils and silicones, which are easily removed with routine cleansing regimens and do not alter the structure of the hair on an appreciable timescale. The technology disclosed enables long- lasting restoration of hair surface hydrophobicity, mimicking the bio-function of the removed or damaged ‘F layer,’ via in situ polymerization of catechol-functionalized monomers with surface modifying agents.

[0108] Experimental data collected in association with the disclosed systems, methods, and composition will now be discussed to demonstrate objective indicia of non-obviousness and novelty. In one experiment, hair surface hydrophobicity was measured by the contact angle of water on the flattened hair surface using an Ossila contact angle goniometer. This{00944416.DOCX }Page 34 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 technique indirectly assesses surface hydrophobicity by the spreadability of a water on a surface; a water droplet administered on a hydrophillic surface spreads out, assuming a contact angle of 0^, whilst a water droplet administered on a hydrophobic surface will bead up to minimize high energy contact surface area, assuming a contact angle of ^ 90^. Contact angle was defined as the angle formed at the intersection of the tangent to the water droplet– air interface and the tangent to the hair–water interface after administering a single droplet and allowing for stabilization for 20 seconds. Contact angles were calculated using Ossila contact angle software.

[0109] Hair samples were obtained from virgin Caucasian hair prepared as 2.5 cm tresses using silicone-lined micro links rings. To obtain damaged hair samples, a subset of hair samples was bleached twice for one hour, i.e., a total period of two cumulative hours, using Clairol Professional® BW2 Powder Lightener with Salon Care™ 30 Volume Crème Developer at a 1:1.5 weight ratio prior to treatment to damage the surface, yielding a contact angle of 0°. The damaged hair samples were subsequently washed with an over-the-counter shampoo to remove residual reagent and dried using a hair dryer. The shampoo used to remove residual reagent, belonging to the family of shampoo products commonly referred to as “baby shampoo” for its use of non-abrasive and / or hypoallergenic ingredients, contains the following ingredients: water; peg-80 sorbitan laurate; cocamidopropyl betaine; sodium laureth sulfate; peg-150 distearate; tetrasodium EDTA; polyquaternium-10; peg-175 diisostearate; phenoxylethanol; caprylyl glycol; sodium hydroxide; and sodium chloride.

[0110] Damaged hair samples were treated with either the disclosed composition or a control formulation. The disclosed composition, in accordance with one implementation, includes (A) a surface modifying compound, comprising a lipid-functionalized compound with polymerizable handle, more specifically an acrylate; (B) an adhesion compound consisting of a catechol functionality and a reactive handle (wherein the reactive handle is a polymerizable handle), more specifically an acrylate; and (C) an initiator, more specifically a thermally sensitive azo-initiator. The adhesion compound was dissolved together with the initiator in a suitable solvent and applied to the hair by brush and allowed to sit for 10 minutes before a second layer of material, containing the neat surface modifying compound, was applied by brush. The treated hair was then heated for one hour. Two controls were selected for reference, processed substantially in an equivalent manner. However, one control treatment lacked the adhesion compound, and the other control treatment lacked both the adhesion compound and the initiator. The predominate purpose of including both control treatments was to demonstrate that (i) the adhesion compound is necessary for long lasting{00944416.DOCX }Page 35 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 restoration of hydrophobicity at the hair surface (wherein “long lasting” is defined, for purposes of this experiment, as lasting for at least 40 cycles of washing with shampoo) and furthermore (ii) the adhesion compound is not sufficient for long lasting restoration of hydrophobicity at the hair surface without the presence of the initiator. Put differently, the adhesion compound is not sufficient without polymerization. Hair was subject to 5 or 40 cycles of washing with shampoo before analysis.

[0111] After two bleaching treatments, the contact angle of all hair samples decreased from 95° to 0°, indicative of the increased hydrophilicity associated with surface lipid removal. Treatment of these damaged hair samples yielded restoration of hydrophobicity, exhibited by an increase in contact angle by 100° or more. Table 2, provided below, shows the hydrophobicity restoration results in further detail. This effect lasted for at least 5 shampoo cycles in all cases, however after 40 shampoo cycles, subsequent contact angle measurement indicated loss of hydrophobicity in all samples except that treated with the disclosed composition. TABLE 2Restoration of Hair Smoothing

[0112] In addition to increased hydrophilicity, damaged hair often additionally presents with increased surface roughness. The surface roughness is caused by detachment or partial detachment of surface cuticle cells. On a macroscopic scale, the surface roughness is associated with poor feel, dullness, frizz, and poor manageability. FIGS.6A and 6B illustrate light microscope images of damaged hair before and after treatment with an example hair surface modifying composition.

[0113] The disclosed composition demonstrates smoothing of the damaged hair surface. Many details of the following experimental procedure overlap with that of the hydrophobicity{00944416.DOCX }Page 36 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 experiment described above and will not be repeated for the sake of conciseness. Any changes to methodology from that which was previously described will be indicated. To demonstrate this, a damaged hair sample, prepared in a similar procedure as described above, was treated with the disclosed composition in an equivalent manner as described above, except with a smoothing surface modifying compound instead of a hydrophobic surface modifying compound. The hair was washed with the aforementioned over-the-counter shampoo five times after treatment and subsequently dried with a blow dryer.

[0114] To assess the surface morphology of hair fibers, light microscopy is commonly utilized, as many of the features of interest can be visualized even at the lowest standard magnification (40x). For example, cuticle cell stripping, peeling, or misshaping, a classic indicator of hair surface damage, can be detected as the thickness of each cuticle cell is generally 0.5 – 1^m thick and a magnification of 40x can resolve features as small as 0.37^ ^m.

[0115] The surface morphology (roughness / smoothness) of untreated damaged hair and treated damaged hair were evaluated by optical microscopy using an OMAX MD82EZ Series Digital Integrated Compound Microscope (100x). FIG.6A is a light microscope image at 100x of the damaged hair before treatment with the disclosed composition. The damaged hair presented visible, irregular roughness, consistent with surface damage. This was particularly evident along the edges of the fiber, where lifted cuticle cells could be observed. FIG.6B is a light microscope image at 100x of the damaged hair after treatment with the disclosed composition. After treatment, the treated damaged hair presented a smooth surface almost entirely absent of defects at both the edges and middle parts, consistent with repair. Colorlessness of Adhesive Coating

[0116] Systems of polymerized catechols on hair can be characterized by intense color formation (i.e., dyeing of the hair) during application. However, this limits the application of these coatings to instances wherein only black to brown colored hair results can be obtained. As such, the adhesive character of the catechol cannot be leveraged for the sake of tuning other surface properties (such as hydrophobicity) without inducing an intense color change.

[0117] The technology disclosed provides a solution involving strong catechol adhesion in the absence of intense color change, consequently enabling a durable surface tuning platform unlimited by color. To demonstrate the absence of color change upon application of the disclosed composition, according to one example implementation, a hair sample was prepared and treated with the disclosed composition in an equivalent manner as described{00944416.DOCX }Page 37 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 above, except the addition of surface modifying compound was omitted. The control sample was treated with a commercial catechol system. Change in the color intensity (lightness) of hair was analyzed using Fiji software. The color analysis window was chosen to encompass all pixels corresponding to a given sample and samples were analyzed before and after treatment. Intensity is defined as the average gray value of the selected area of hair tresses where a value of 0 is equivalent to black and a value of 255 is equivalent to white. Photograph lighting was controlled using a light box (PULUX 20cm Photography Shooting Light Tent Kit™). The measured values resulting from measurement are summarized in Table 3, which includes a measurement of the intensity value before and after treatment, respectively, for both the disclosed composition and the control system. As demonstrated by the results of Table 3, treatment with the disclosed composition imparts no significant change in intensity to the hair, whilst a significant decrease in intensity is observed for the control commercial catechol system. TABLE 3Longevity of Color Modification

[0118] Incumbent hair dyeing technology can be categorized as oxidative or non- oxidative. Oxidative color, including that originating from poly(dopamine), is formed in situ by a reaction catalyzed by an exogenous oxidant (e.g., H2O2, ammonium persulfate, sodium periodate, etc.), molecular oxygen, base, or some combination thereof. These conditions simultaneously induce polymerization of colorless monomers into a colored polymer and oxidative damage to the hair itself. Further, the color precursors used in these formulations tend to be associated with risks pertaining to both environmental and human health.

[0119] Non-oxidative color, on the contrary, uses pre-formed colored compounds that diffuse into and bind weakly to outer layers of the hair. While typically considered to be safer and less damaging, the noncovalent interactions these colorants form the hair are weak{00944416.DOCX }Page 38 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 enabling them to diffuse out of the hair during routine shampooing. As such, these colorants have poor retention.

[0120] Strongly bound, non-oxidative color is desirable as it offers the possibility for reduced damage together with good longevity. For example, one approach can involve using pre-formed reactive dyes capable of covalently bonding free nucleophiles in the hair. These dyes, however, may only significantly dye hair after it has been structurally perturbed by damaging pre-treatments, such as reduction or acid treatment.

[0121] The technology disclosed solves this problem by increasing the binding strength of pre-formed dyes to the hair via linking to a catechol-containing compound. In effect, this approach avoids damage from strong oxidative chemistries, reduces health and environmental risk associated with oxidative color precursors, increases longevity of the colorant, and broadens the scope of colors relative to existing catechol-based polymers.

[0122] The utility of the disclosed system in improving the colorfastness of a pre-formed colored compound is demonstrated by the following experiment.

[0123] Hair samples, prepared and treated equivalent to that described above, were treated with either the disclosed composition or a control system. The disclosed formulation consists of (A) an adhesion compound comprising a catechol functionality and a reactive handle, wherein the reactive handle is a polymerizable handle, more specifically an acrylate; (B) a second compound, more specifically a compound configured to react with the reactive handle of the adhesion compound and also configured to react with the surface modifying compound (“reactive compound”); (C) a third compound, more specifically a surface modifying compound configured to react with second compound (e.g., a reactive dye; “surface modifying compound”); and (D) an initiator, wherein the initiator can be a thermally sensitive azo-initiator. To prepare the composition, the adhesion compound, reactive compound, and initiator were dissolved in a suitable solvent and applied to the hair by brush and allowed to sit for 10 minutes before heating for one hour. The hair was then washed and blown dry, as previously described, before incubating in a solution of the surface modifying compound, more specifically the reactive dye. The hair was again washed and blown dry before analysis. Control samples were treated with all components except the adhesion compound or all components except the adhesion compound and initiator. Washing was performed only until the control sample (reactive dye only) showed complete restoration of its original color (complete removal of the dye).

[0124] Color change of hair was evaluated by RGB analysis using Fiji software. The color analysis window was chosen to encompass all pixels corresponding to a given sample.{00944416.DOCX }Page 39 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 Specifically, the blueness of each sample was assessed as this was the color of the reactive dye studied. Blueness was defined as the ratio of Blue (B) to Red (R) components (B / R) in each pixel. The influence of lighting on perceived color was mitigated by using a light box (PULUX 20cm Photography Shooting Light Tent Kit™). Table 4 reports experimental data comparing the color fastness of the blue reactive dye surface modifying compound in the absence and presence of the disclosed composition components. Higher B / R ratios are interpreted as high color fastness, exhibited by a higher degree of blueness, and thereby retention of the blue surface modifying compound. TABLE 4

[0125] After treatment and one cycle of washing, the hair treated with all components of the disclosed composition showed the highest blueness, which is accordingly indicative of the greatest color fastness. The control containing the initiator showed marginally better color fastness than the control lacking both the initiator and adhesion compound, suggesting that the polymerization of the system components improved adhesion. The blueness of the initiator containing control was still, however, roughly 50% lower than that of the complete composition, underlining the essential nature of all components. After 20 wash cycles, the control lacking both the initiator and adhesion compound showed complete restoration of its original color, indicating complete removal of the surface modifying compound. In contrast, the sample treated with the complete disclosed composition showed only a 4% change in color, whilst the control treated with the disclosed composition in the absence of the adhesion compound showed a greater than 30% reduction in blueness. These results demonstrate the substantial improvement in retention of pre-formed dyes by the complete disclosed composition.{00944416.DOCX }Page 40 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 Tuning of Multiple Surface Properties: Hydrophobicity and Color

[0126] The disclosed technology has the advantage of being able to controllably modify multiple cosmetic properties of a single hair surface through a single treatment with good longevity. The following experiment provides an example demonstration of this particular feature. Hair samples were prepared and treated in a similar manner to that previously described. The disclosed composition comprises (A) a surface modifying compound, wherein the surface modifying compound is a lipid-functionalized compound with a polymerizable handle, and more specifically an acrylate; (B) an adhesion compound consisting of a catechol functionality and a reactive handle, wherein the reactive handle is a polymerizable handle, more specifically an acrylate; and (C) an initiator, such as a thermally sensitive azo-initiator. The adhesion compound was dissolved together with the initiator in a suitable solvent and applied to the hair by brush and allowed to sit for 10 minutes before a second layer of material, containing the neat surface modifying compound was applied by brush. The treated hair was then heated for one hour. The hair was then washed and blown dry before being treated with a reactive surface modifying compound configured to react with the formed polymer, for example a metallic salt, inducing a visually recognizable color change. The hair was again washed and blown dry before analysis. The control sample was processed with a commercial catechol system according to the manufacturer’s instructions.

[0127] Assessments of surface hydrophobicity and color change were made by measuring the contact angle of water on the hair surface and measuring the change in intensity of the hair color, as previously described. Both the present invention and the commercial catechol treatment yielded a color change from blonde to brown (demonstrated by the reduction in intensity after treatment in Table 5). Only the disclosed composition, however, yielded a change in the surface hydrophobicity after treatment, as demonstrated by an increase in contact angle from 0^ (hydrophilic) to over 100^ (hydrophobic), alongside a color change. The results shown in Table 5 accordingly demonstrate that the disclosed composition may be used to simultaneously restore the hydrophobicity of the hair surface and color the hair, providing a novel advancement to the haircare market.{00944416.DOCX }Page 41 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 TABLE 5Particular Implementations

[0128] Some particular implementations and features for the technology disclosed are described in the following discussion.

[0129] Many implementations of the technology disclosed include a system for tuning at least one surface property of a keratin-containing material, the system comprising a first compound including a keratin-binding catechol derivative, an optional spacer, and a first reactive handle. The system also includes a second compound having a second reactive handle, where 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.

[0130] Some implementations may include at least one of a crosslinker. Other implementations may include a metal ion configured to increase at least one of an adhesion property and a color of the keratin-containing material.

[0131] In one implementation, the first compound includes hydroxyl or hydrogen groups bound to an aromatic ring. In another implementation, the first reactive handle of the first compound is a polymerizable handle selected from one of a methacrylamide, an acrylamide, a methacrylate, or an acrylate. In other implementations, the first reactive handle 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. Certain implementations include a first compound comprising an optional spacer including a C1-4alkyl group. 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 in some{00944416.DOCX }Page 42 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 implementations. Alternatively, in other implementations, 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.

[0132] Some implementations include an initiator compound. The initiator compound is activatable by one or more stimuli and the one or more stimuli can include one or more of a chemical stimulus, a heat stimulus, and a light stimulus.

[0133] The second compound can be a surface modifying compound configured to produce a microscale smoothing effect on a surface of the keratin-containing material. The second compound can also be a surface modifying compound configured to increase a hydrophobicity of a surface of the keratin-containing material, and the surface modifying compound further may include a hydrophobic moiety selected from an alkyl chain or a siloxane. The second compound can alternatively be a surface modifying compound configured to absorb, scatter, or emit light, thereby producing a color change in the keratin- containing material. The system may further include microfibers. The system can also further include 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. Preferably, the pH of the system is equal to or less than 7.5. The one or more implementations described herein enumerate many examples of surface modifying compounds able to induce the above-mentioned modifications (smoothing, hydrophobicity, and so on). It is to be understood that the preceding description is presented to enable the use of the disclosed system and methods, but a user skilled in the art will recognize that many variations and similar components can be used for the same purpose without deviating from the scope of the technology disclosed.

[0134] In one implementation, the components of the disclosed system are mixed and exposed to the stimulus prior to an application of the mixture to the keratin-containing material. In another implementation, the reaction between the first compound and the second compound is an in situ reaction, exposed to the stimulus following application to the keratin- containing material.

[0135] The technology disclosed includes systems, methods, and compositions for tuning the surface properties of keratin-containing material, such as hair. The technology disclosed includes a catechol derivative that can be linked with a surface modifying component at a reactive handle removed from the aromatic ring; thus, the reaction between the catechol{00944416.DOCX }Page 43 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 derivative and the surface modifying component maintains the degree of substitution of the aromatic ring.

[0136] 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 modifies one or more properties of the keratin-containing material without using strongly oxidizing conditions or strongly basic conditions, and therefore provides a mild approach for modifying the cosmetic properties of the material, such as the color, gloss, frizz-resistance, or lightness of hair. 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.

[0137] The technology disclosed has been described in an illustrative manner, and it is to be understood that the terminology which has been used is intended to be in the nature of words of description rather than of limitation. Obviously, many modifications and variations of the technology disclosed are possible in light of the above teachings. It is, therefore, to be understood that within the scope of the appended claims, wherein reference numerals are merely for convenience and are not to be in any way limiting, the technology disclosed may be practiced otherwise than as specifically described. For example, the relative quantities of the components within the disclosed composition may be varied to optimize the desired effects, additional reactants or ingredients may be added, and / or similar compounds may be substituted for one or more of the compounds described. Additional advantageous features and functionalities associated with the systems, methods, and processes of the present disclosure will be apparent from the appended claims. Moreover, those skilled in the art will recognize, or be able to ascertain using no more than routine experimentation, many equivalents to the implementations described herein.

[0138] Many implementations of the technology disclosed relate to a method for modifying the surface properties of a keratin-containing material, such as hair. The method can include contacting the keratin-containing material with (i) a reactive adhesion compound comprising a catechol and (ii) a surface modifying compound configured to modify a surface property of the hair and react with the adhesion compound. The method further includes facilitating a reaction between the reactive adhesion compound and the surface modifying compound, triggering a modification of a surface property of the hair. In some implementations, the keratin-containing material is contacted with the reactive adhesion compound, a surface modifying compound, and a third additional compound configured to{00944416.DOCX }Page 44 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2 react with the reactive adhesion compound and a surface modifying compound. In such implementations, the method further includes facilitating a reaction between the reactive adhesion compound, the surface modifying compound, and the third additional compound, thereby triggering a modification of a surface property of the hair. The facilitation of the reaction can further include introduction of one or more stimuli, as described herein, such that the stimuli induce the reaction between the surface modifying compound and the adhesion compound.

[0139] In some implementations, the disclosed composition contains a compound that absorbs, reflects, or refracts electromagnetic waves such as UV. In other implementations, the surface modifying compound produces an increase in specular reflectance, thereby improving the shine or gloss of the hair surface. In one implementation, the surface modifying compound reduces the permeability of the hair surface, thereby improving longevity of colorants or other cosmetic ingredients applied to the hair. One or more implementations further include light reflecting, refracting, or emitting compounds configured to increase the perceived lightness of a hair shade.

[0140] In one disclosed implementation, a method for modifying a surface property of hair, or another keratin-containing material, includes modifying a surface property of human hair with stimuli-responsive adhesion of a catechol derivative-based coating. The modification further includes applying a coating material comprising a catechol derivative to the hair surface, activating the coating material, and facilitating adhesion of the adhesive coating to the hair surface such that the adhesive coating modifies at least one property of the hair surface. The activation of the coating material includes a stimuli-responsive reaction further comprising converting the catechol derivative to an adhesive catechol, thereby producing an adhesive coating. In certain implementations, the catechol derivative further comprises one or more pro-adhesive reaction sites. A pro-adhesion reaction site exists at a hydroxyl group of the catechol derivative, or at a chemical handle bonded directly or indirectly to an aromatic ring of the catechol derivative.

[0141] In many implementations, the adhesive catechol is produced by polymerization of the catechol derivative. Alternative implementations involve producing the adhesive catechol by conjugating the catechol derivative to a pre-formed polymer and / or crosslinking the catechol derivative. Some implementations involve a combination of certain components from these processes to produce the adhesive catechol. Several implementations further comprise the introduction of an additive to the coating, such as a colorant, inorganic pigment or dye, organic pigment or dye, and so on.{00944416.DOCX }Page 45 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2

[0142] In one or more disclosed implementations, the method includes modifying a particular property of the hair surface such as a color, a texture, a thickness, a strength, an elasticity, or a hydrophobicity of hair. In one implementation, the method further includes modifying more than one property of the hair surface such that the modification is orthogonally controllable. That is to say, modifying a particular hair surface property is orthogonally controllable in relation to at least one of another hair surface property, the longevity of the adhesive coating, the strength or resiliency of the adhesive coating, and / or the biocompatibility metric of the adhesive coating. For example, one implementation of the technology disclosed involves modification of the apparent color of the hair surface without effecting the biocompatibility of the adhesive coating. Another implementation involves modification of the physical properties, e.g., curl, of the hair fiber without effecting the hydrophobicity of the hair fiber. A user skilled in the art will recognize the one or more factors relating to the adhesive coating, the application of the adhesive coating, and the effect of the adhesive coating on the human hair that can be orthogonally controlled in one or more combinations. While not all implementations of the technology disclosed involve orthogonal control of a plurality of properties simultaneously, most implementations of the technology disclosed involve orthogonal control of at least one property in relation to at least one other property.

[0143] One disclosed implementation includes the use of an energetic stimulus such as heat or light. In yet another disclosed implementation, the stimulus for adhesion is a chemical stimulus such as a change in pH. In yet other implementations, a combination of stimuli is used.

[0144] The method described in this section and other sections of the technology disclosed can include one or more of the following features and / or features described in connection with additional methods disclosed. In the interest of conciseness, the combinations of features disclosed in this application are not individually enumerated and are not repeated with each base set of features. The reader will understand how features identified in this method can readily be combined with sets of base features identified as implementations.

[0145] Some implementations of the disclosed method further include facilitation of adhesion via the application of a bridging ion species to the hair surface. Other implementations of the disclosed method further include removing the adhesive coating by at least one of an ion wash, a borax-based wash, or a wash that changes the pH of the adhesive coating.{00944416.DOCX }Page 46 of 51Nonprovisional Patent Application Atty. Docket No. EDUL 1000-2

[0146] In some implementations, a method is disclosed for hair coloring wherein the method comprises applying a coloring material (i.e., a catechol derivative) and at least one of an inorganic colorant or an organic colorant to the surface of human hair. The coloring material can be activated via a stimuli-responsive reaction that further involves converting the catechol derivative to an adhesive catechol, thereby producing an adhesive colorant. Adhesion of the adhesive coating to the hair surface results in the modification of the apparent color of the hair surface. Certain implementations include repairing a hydrophobic cuticle layer of human hair, wherein the method comprises applying a coating material (i.e., a catechol derivative) to the surface of human hair. The coating material can be activated via a stimuli-responsive reaction that further involves converting the catechol derivative to an adhesive catechol, thereby producing an adhesive coating. Adhesion of the adhesive coating to the hair surface results in the modification of a hydrophobic character, a frizz-resistance, a manageability, or a gloss of the hair surface. However, these implementations are explicitly listed for convenience of description and should not be considered limitations of the implementations of the technology disclosed.

[0147] The preceding description is presented to enable the making and use of the technology disclosed. One or more modifications to the disclosed implementations will be apparent, and the general principles defined herein may be applied to other implementations and applications without departing from the spirit and scope of the technology disclosed. Thus, the technology disclosed is not intended to be limited to the implementations shown but is to be accorded the widest scope consistent with the principles and features disclosed herein. The scope of the technology disclosed is defined by the appended claims.

[0148] What is claimed is:{00944416.DOCX }Page 47 of 51

Claims

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 51Nonprovisional 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 51Nonprovisional 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

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