Plant extract compositions for forming protective coatings

A method of forming a composition, comprising:

• adding cutin-containing plant matter to a first solvent to form a first mixture, the first solvent having a boiling point at a first temperature at a pressure of one atmosphere;
• heating the first mixture to a second temperature, wherein the second temperature is higher than the first temperature, and to a second pressure, wherein the second pressure is higher than one atmosphere, to form a second mixture comprising monomers, oligomers, or combinations thereof derived from the cutin-containing plant matter;
• separating the first solvent from the monomers, oligomers, or combinations thereof in the second mixture;
• and
• adding the monomers, oligomers, or combinations thereof to a second solvent;
• wherein the first solvent comprises a nucleophilic solvent, liquid CO2, supercritical CO2, or combinations thereof.

A method of forming a composition, comprising:

• adding cutin-containing plant matter to a solvent to form a first mixture, the solvent having a boiling point at a first temperature at a pressure of one atmosphere;
• and
• heating the first mixture to a second temperature, wherein the second temperature is higher than the first temperature, and to a second pressure, wherein and the second pressure is higher than one atmosphere, to form a second mixture comprising monomers, oligomers, or combinations thereof derived from the cutin-containing plant matter;
• wherein
• at least a portion of the monomers or oligomers in the second mixture are unsaturated;
• and wherein the solvent comprises a nucleophilic solvent, liquid CO2, supercritical CO2, or combinations thereof.

A method of forming a composition, comprising:

• adding cutin-containing plant matter to water to form a first mixture;
• and
• heating the first mixture from a first temperature and first pressure to a second temperature and second pressure, wherein the second temperature is higher than the boiling point of water at one atmosphere and the second pressure is higher than one atmosphere, to form a second mixture comprising a group of compounds of Formula II, esters thereof, or compounds of Formula III, wherein Formula II and Formula III are:
• wherein for Formula II:
• R1, R2, R4 and R5 are each independently —H, —OR11, —NR11R12, —SR11, halogen, —C1-C6 alkyl, —C1-C6 alkenyl, —C1-C6 alkynyl, —C3-C7 cycloalkyl, aryl, or 5- to 10-membered ring heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with —OR11, —NR11R12, —SR11, or halogen;
• R11 and R12 are each independently —H, —C1-C6 alkyl, —C1-C6 alkenyl, or —C1-C6 alkynyl;
• the symbol represents an optionally single or cis or trans double bond;
• the symbol ══ represents a cis or trans double bond;
• R3 is —OH and R3′ is selected from the group consisting of —H, —C1-C6 alkyl, —C1-C6 alkenyl, —C1-C6 alkynyl, —C3-C7 cycloalkyl, and aryl when between R3 and R3′ is a single bond, and R3 and R3′ are absent when between R3 and R3′ represents a double bond;
• n is an integer in the range of 0 to 11;
• m is an integer in the range of 0 to 25;
• and
• 0≤m+n≤25;
• wherein for Formula III:
• R1, R2, R5, R6, R9, R10, R11, R12, and R13 are each independently, at each occurrence, —H, —OR14, —NR14R15, —SR14, halogen, —C1-C6 alkyl, —C2-C6 alkenyl, —C2-C6 alkynyl, —C3-C7 cycloalkyl, aryl, or heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more —OR14, —NR14R15, —SR14, or halogen;
• R3, R4, R7, and R8 are each independently, at each occurrence, —H, —OR14, —NR14R15, —SR14, halogen, —C1-C6 alkyl, —C2-C6 alkenyl, —C2-C6 alkenyl, —C2-C6 alkynyl, —C3-C7 cycloalkyl, aryl, or heteroaryl wherein each alkyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more —OR14, —NR14R15, —SR14, or halogen;
• or
• R3 and R4 can combine with the carbon atoms to which they are attached to form a C3-C6 cycloalkyl, a C4-C6 cycloalkenyl, or 3- to 6-membered ring heterocycle;
• and/or
• R7 and R8 can combine with the carbon atoms to which they are attached to form a C3-C6 cycloalkyl, a C4-C6 cycloalkenyl, or 3- to 6-membered ring heterocycle;
• R14 and R15 are each independently, at each occurrence, —H, —C1-C6 alkyl, —C2-C6 alkenyl, or —C2-C6 alkynyl;
• the symbol represents a single bond or a cis or trans double bond;
• the symbol ══ represents a cis or trans double bond;
• n is 0, 1, 2, 3, 4, 5, 6, 7 or 8;
• m is 0, 1, 2 or 3;
• q is 0, 1, 2, 3, 4 or 5;
• r is 0, 1, 2, 3, 4, 5, 6, 7 or 8;
• and
• R is selected from —H, —C1-C6 alkyl, —C2-C6 alkenyl, —C2-C6 alkynyl, —C3-C7 cycloalkyl, aryl, 1-glyceryl, 2-glyceryl, or heteroaryl.