CN113631632A - Dihydroxylactam-based polymers, compositions thereof and uses thereof - Google Patents

Abstract

A lactam-functionalized polymer is disclosed. The dihydroxylactam-based polymers include polyesters, polycarbonates, polyethers, polyesterethers, polyesteramides, polyimides, polyamides, polyacrylates and polyesterimides, and polyurethanes. Also disclosed is the use of the dihydroxylactam-based polymers.

Description

Dihydroxylactam-based polymers, compositions thereof and uses thereof

Technical Field

The present application relates to dihydroxylactam-based polymers, compositions thereof, and uses thereof.

Background

N-vinyl lactam-based polymers are those polymers which have lactam groups, such as pyrrolidone or caprolactam, wherein the nitrogen atoms of the lactam are directly bonded to the polymer main chain. These polymers include poly (N-vinyl-2-pyrrolidone), poly (N-vinyl-epsilon-caprolactam) and poly (N-vinyl-2-pyrrolidone-co-N-vinyl acetate), which can have a wide range of molecular weights, which makes them useful in many applications, such as film formers, protective colloids, suspending agents, and many other uses. A description of these applications and properties can be found in the technical Manual "PVP Polyvinylpyrrolidine Polymers" published by International Specialty Products, which is incorporated herein by reference in its entirety.

The success of N-vinyl lactam polymers is due in part to the chemical structure of the lactam group. The nitrogen atom of the lactam can form hydrogen bonds with compounds containing-OH and-NH groups by virtue of its lone pair of electrons. This interaction may be manifested by a variety of properties, including adhesion (e.g., glue stick, hair styling, tablet adhesive), crystallization inhibitors (e.g., gas hydrates, sucrose solutions), and complexing agents (e.g., dyes, active ingredients).

In addition to molecular weight, the number of carbon atoms in the lactam ring may vary. Well known lactams include those having three carbon atoms per nitrogen atom in the ring (propiolactam) to six carbon atoms per nitrogen atom in the ring (heptanolactam). Increasing the number of carbon atoms in the ring changes the hydrophilicity/hydrophobicity balance of the molecule. Although both poly (N-vinyl-2-pyrrolidone) and poly (N-vinyl-epsilon-caprolactam) are water soluble, the former is more hydrophilic and can absorb more water in a humid environment than the latter.

However, the available range of lactam ring sizes and polymer molecular weights is not sufficient to design new monomers and polymers with truly new functionalities. For example, because the nitrogen atom of the N-vinyl lactam is directly attached to the polymer backbone without a spacer group, there is limited choice for adjusting the hydrophilic/hydrophobic balance of the molecule or changing the relatively high glass transition temperature [ e.g., about 180 ℃ for poly (N-vinyl-2-pyrrolidone) ]. A new approach is needed to modify the structure of N-vinyl lactams to facilitate new properties and end-user applications.

To obtain different properties, current technology relies on copolymerizing other monomer units with the N-vinyl lactam units. Many such non-homopolymers are known, including those formed from N-vinyl acetate, styrene, dimethylaminoethyl methacrylate, dimethylaminopropyl methacrylamide, acrylic acid, and lauryl methacrylate. Through these copolymerizations, properties can be altered, including hydrophobicity/hydrophilicity, film formation, flexibility, foamability, moisture response, viscosity, gloss, and tackiness. Although copolymerization can produce valuable products, it is essential that copolymerization be carried out when the homopolymer does not provide the desired properties. There is a need for novel lactam-based monomers and polymers thereof that provide extended functionality.

In addition to functional limitations, N-vinyl lactam-based polymers require preparation methods and analytical test means that can ensure sufficiently low residual monomers. There is a need for a next generation of lactam-based compounds with new properties and without N-vinyl lactam monomers.

There is a related family of compounds, also based on N-alkyl lactams, which help to extend the lactam part, where the alkyl group is covalently bonded to the nitrogen of the lactam. A variety of N-alkyllactams are known, including, but not limited to, N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone, N-hydroxyethyl-2-pyrrolidone, N-cyclohexyl-2-pyrrolidone, N-octyl-2-pyrrolidone, and N-dodecyl-2-pyrrolidone, all of which are commercially available from Ashland LLC (Bridgewater, N.J.). Also known is N-hydroxymethyl-2-caprolactam (Benson, 1948). These non-polymeric chemicals are useful as solvents, surface tension reducers and low foaming surface wetting agents.

The prior art teaches several modified N-vinyl lactams from N-alkyl lactams. These documents include: U.S. patent nos. 2,882,262; 4,008,247, respectively; 4,189,601, respectively; 4,190,582, respectively; 4,191,833, respectively; 4,191,834, respectively; 4,439,616, respectively; 4,609,706, respectively; 5,209,347, respectively; 5,252,689, respectively; 5,466,770, respectively; 6,369,163, respectively; 6,630,599, respectively; and U.S. patent applications: 2007/123,673, respectively; and foreign patents: EP385,918; EP550,744; and foreign patent applications: WO 91/12243; WO 02/42383; WO 03/006568; WO 2007/051738; WO 2008/098885; WO 2008/098887; WO 2011/022457; WO 2011/085280; and WO 2011/022457. Many of these publications describe various esters of N-hydroxyalkylceramides, such as N-hydroxyethylpyrrolidone.

Lipids based on 1- (2, 3-dihydroxypropyl) pyrrolidin-2-one are described in WO 2011/056682.

Furthermore, Kim et al describe linear oligomers and polyurethanes with pyrrolidone side rings. (Uzbek Chemical Journal, volume 17, No. 2, pages 48-50, 1973).

Summary of The Invention

One object of the present application relates to a polymer obtainable from a reaction mixture comprising: (i) at least one dihydroxylactam moiety; (ii) at least one functional moiety having a hydroxyl-reactive functional group; wherein the amounts of (i) and (ii) are independently about 0.01 mole% to about 99.99 mole%, and the polymer is selected from the group consisting of polyesters, polycarbonates, polyethers, polyester ethers, polyester amides, polyimides, polyamides, polyacrylates, and polyesterimides; or wherein (i) and (ii) are each present in an amount other than 50 mol% and the polymer is a polyurethane.

One object of the present application relates to a polymer obtainable from a reaction mixture comprising: (i) at least one dihydroxylactam moiety or modified dihydroxylactam moiety having a reactive functional group; the modified dihydroxylactam moiety may be comprised of esters, epoxies, ethers, urethanes, acrylates, anhydrides, and combinations thereof, as additional functional groups attached to the dihydroxylactam moiety and (ii) at least one functional moiety having a hydroxyl-reactive group or a modified hydroxyl-reactive functional group; wherein the amounts of (i) and (ii) are independently about 0.01 mol% to about 99.99 mol% and the polymer is selected from the group consisting of polyesters, polycarbonates, polyethers, polyester ethers, polyester amides, polyimides, polyamides, polyacrylates, polyesterimides, and polyurethanes.

Another object of the present application relates to a polymer obtainable from a reaction mixture comprising: (i) a dihydroxylactam moiety selected from the group consisting of:

wherein n is an integer from 1 to 6; and (ii) at least one functional moiety having hydroxyl-reactive functional groups, wherein the amounts of (i) and (ii) are independently about 0.01 mole% to about 99.99 mole%, and the polymer is selected from the group consisting of polyesters, polycarbonates, polyethers, polyester ethers, polyesteramides, polyimides, polyamides, polyacrylates, and polyesterimides; or wherein (i) and (ii) are each present in an amount other than 50 mol% and the polymer is a polyurethane.

Another object of the present application relates to a polymer obtained from a reaction mixture comprising: (i) n- (2, 3-dihydroxypropyl) -2-pyrrolidone and/or 1- [2- (2, 3-dihydroxypropoxy) ethyl ] -2-pyrrolidone, and (ii) poly (D, L-lactide); wherein the amounts of (i) and (ii) are independently about 0.01 mol% to about 99.99 mol%, and the polymer is a polyester.

Another object of the present application relates to a polymer obtained from a reaction mixture comprising: (i) n- (2, 3-dihydroxypropyl) -2-pyrrolidone and/or 1- [2- (2, 3-dihydroxypropoxy) ethyl ] -2-pyrrolidone, and (ii) diphenyl carbonate; wherein the amounts of (i) and (ii) are independently about 0.01 mol% to about 99.99 mol%, and the polymer is a polycarbonate.

Another object of the present application relates to a polymer obtained from a reaction mixture comprising: (i) n- (2, 3-dihydroxypropyl) -2-pyrrolidone and/or 1- [2- (2, 3-dihydroxypropoxy) ethyl ] -2-pyrrolidone, (ii) dibromoethane, (iii) glycidyl ether; wherein the amounts of (i), (ii), and (iii) are independently about 0.01 mol% to about 99.99 mol%, and the polymer is a polyether.

Another object of the present application relates to a polymer obtained from a reaction mixture comprising: (i) n- (2, 3-dihydroxypropyl) -2-pyrrolidone and/or 1- [2- (2, 3-dihydroxypropoxy) ethyl ] -2-pyrrolidone, and (ii)1, 4-dibromobutane, and the reaction products of (i) and (ii) with adipoyl chloride or adipic acid; wherein the amounts of (i), (ii), and (iii) are independently about 0.01 mol% to about 99.99 mol%, and the polymer is a polyester ether.

A different object of the present application relates to polymers obtained from a reaction mixture comprising: (i) n- (2, 3-dihydroxypropyl) -2-pyrrolidone and/or 1- [2- (2, 3-dihydroxypropoxy) ethyl ] -2-pyrrolidone, and (ii) an alpha-amino acid under p-toluenesulfonic acid; wherein the product of (i) and (ii) is reacted with (iii) bis (p-nitrophenylsuccinate) and the levels of (i), (ii) and (iii) are independently from about 0.01 mol% to about 99.99 mol%, the polymer being a polyesteramide.

Another object of the present application relates to a polymer obtained from a reaction mixture comprising (i) N- (2, 3-dihydroxypropyl) -2-pyrrolidone and/or 1- [2- (2, 3-dihydroxypropoxy) ethyl ] -2-pyrrolidone, and (ii) p-fluoronitrobenzene; wherein the product of (i) and (ii) is further hydrogenated to produce a diamine (iii) and reacted with (iv) pyromellitic dianhydride, and the amounts of (i), (ii), and (iv) are independently from about 0.01 mol% to about 99.99 mol%, and the polymer is a polyimide.

Another object of the present application relates to a polymer obtained from a reaction mixture comprising: (i) n- (2, 3-dihydroxypropyl) -2-pyrrolidone and/or 1- [2- (2, 3-dihydroxypropoxy) ethyl ] -2-pyrrolidone, and (ii) p-fluoronitrobenzene; wherein the product of (i) and (ii) is further hydrogenated to produce diamine (iii) and reacted with (iv) adipic acid chloride or adipic acid, and the content of (i), (ii) and (iv) is independently from about 0.01 mol% to about 99.99 mol%, and the polymer is a polyamide.

Another object of the present application relates to a polymer obtained from a reaction mixture comprising: (i) n- (2, 3-dihydroxypropyl) -2-pyrrolidone and/or 1- [2- (2, 3-dihydroxypropoxy) ethyl ] -2-pyrrolidone, and (ii) methacryloyl chloride; wherein the product of (i) and (ii) is reacted with (iii) methyl methacrylate, and the amounts of (i), (ii), and (iii) are independently from about 0.01 mol% to about 99.99 mol%, and the polymer is a polyacrylate.

Another object of the present application relates to a polymer obtained from a reaction mixture comprising: (i) n- (2, 3-dihydroxypropyl) -2-pyrrolidone and/or 1- [2- (2, 3-dihydroxypropoxy) ethyl ] -2-pyrrolidone, and (ii) p-fluoronitrobenzene; wherein the product of (i) and (ii) is further hydrogenated to produce a diamine (iii) and reacted with (iv) N- (4-chlorocarbonylphenyl) trimellitimide acid chloride, and the levels of (i), (ii) and (iv) are independently from about 0.01 mole% to about 99.99 mole%, and the polymer is a polyesterimide.

Another object of the present application relates to polymers obtained from a reaction mixture comprising (i) N- (2, 3-dihydroxypropyl) -2-pyrrolidone and/or 1- [2- (2, 3-dihydroxypropoxy) ethyl ] -2-pyrrolidone, and (ii) a) isophorone diisocyanate, b) polyethylene glycol, and optionally c) octanol; wherein (i) and (ii) are each present in an amount other than 50 mol% and the polymer is a polyurethane.

Another object of the present application relates to a composition comprising: (I) a polymer obtained from a reaction mixture comprising: (i) at least one dihydroxylactam moiety, and (ii) at least one functional moiety having a hydroxyl-reactive functional group, wherein (i) and (ii) are independently present in an amount of about 0.01 mole% to about 99.99 mole%, and the polymer is selected from the group consisting of polyesters, polycarbonates, polyethers, polyester ethers, polyesteramides, polyimides, polyamides, polyacrylates, and polyesterimides; or wherein neither of (i) and (II) is present in an amount of 50 mol% and the polymer is a polyurethane, and (II) one or more additives.

Another object of the present application relates to a personal care composition comprising (I) a polymer obtained from a reaction mixture comprising (I) at least one dihydroxylactam moiety, and (ii) at least one functional moiety having a hydroxyl-reactive functional group; wherein the amounts of (i) and (ii) are independently about 0.01 mole% to about 99.99 mole%, and the polymer is selected from the group consisting of polyesters, polycarbonates, polyethers, polyester ethers, polyester amides, polyimides, polyamides, polyacrylates, and polyesterimides; or wherein neither of (i) and (II) are present in an amount of 50 mol% and the polymer is a polyurethane, and (II) one or more cosmetically acceptable additives.

Another object of the present application relates to a coating composition comprising: (I) a polymer obtained from a reaction mixture comprising: (i) at least one dihydroxylactam moiety, and (ii) at least one functional moiety having a hydroxyl-reactive functional group; wherein the amounts of (i) and (ii) are independently about 0.01 mole% to about 99.99 mole%, and the polymer is selected from the group consisting of polyesters, polycarbonates, polyethers, polyester ethers, polyesteramides, polyimides, polyamides, polyacrylates, and polyesterimides; or wherein neither of (i) and (II) are present in an amount of 50 mol% and the polymer is a polyurethane, and (II) one or more coating additives.

Another object of the present application relates to a pharmaceutical composition comprising: (I) a polymer obtained from a reaction mixture comprising: (i) n- (2, 3-dihydroxypropyl) -2-pyrrolidone and/or 1- [2- (2, 3-dihydroxypropoxy) ethyl ] -2-pyrrolidone; (ii) poly (D, L-lactide); wherein the amounts of (i) and (II) are independently about 0.01 mol% to about 99.99 mol%, and the polymer is a polyester, and (II) one or more pharmaceutically acceptable additives.

Another object of the present application relates to a process for preparing a polymer comprising: (A) (ii) at least one functional moiety having a hydroxyl-reactive functional group; wherein the amounts of (i) and (ii) are independently about 0.01 mole% to about 99.99 mole%, and the polymer is selected from the group consisting of polyesters, polycarbonates, polyethers, polyester ethers, polyester amides, polyimides, polyamides, polyacrylates, and polyesterimides; or wherein neither of (i) and (ii) is present in an amount of 50 mol% and the polymer is a polyurethane; (B) charging (a) to a reaction vessel under an inert gas atmosphere and adding a solvent; (C) stirring the reaction mixture (B) and maintaining the temperature at 55-70 ℃ for about 30 minutes; (D) adding an additional reactive moiety to (C); (E) polymerizing (D) with a catalyst for 3 to 5 hours; (F) recovering the desired polymer from (E).

Another object of the present application relates to a process for preparing a polymer comprising: (A) (i) at least one dihydroxylactam moiety, and (ii) at least one functional moiety having a hydroxyl-reactive functional group, wherein (i) and (ii) are independently present in an amount of about 0.01 to about 99.99 mole%, and the polymer is selected from the group consisting of polyesters, polycarbonates, polyethers, polyester ethers, polyesteramides, polyimides, polyamides, polyacrylates, and polyesterimides; or wherein the content of each of (i) and (ii) is not 50 mol% and the polymer is a polyurethane; (B) charging (a) to a reaction vessel under an inert gas atmosphere; (C) stirring the reaction mixture (B) and maintaining the temperature at 65-80 ℃ for about 30 minutes; (D) adding an additional reactive moiety to (C); (E) polymerizing (D) with a catalyst; (F) raising the temperature of (E) to 90-110 ℃ and maintaining the temperature for about 2-3 hours; (G) recovering the desired polymer from (F).

Detailed Description

Before explaining at least one embodiment of the disclosure in detail, it is to be understood that the disclosure is not limited in its application to the details of construction and the arrangement of the components or steps or methods set forth in the following description or illustrated in the drawings. The disclosure is capable of other embodiments or of being practiced or carried out in various ways. Also, it is to be understood that the phraseology and terminology employed herein is for the purpose of description and should not be regarded as limiting.

Unless otherwise defined herein, technical terms used in connection with the present disclosure shall have meanings that are commonly understood by those of ordinary skill in the art. Furthermore, unless the context requires otherwise, singular terms shall include the plural and plural terms shall include the singular.

All patents, published patent applications, and non-patent publications mentioned in this specification are indicative of the level of skill of those skilled in the art to which this disclosure pertains. All patents, published patent applications, and non-patent publications cited in any section of this application are expressly incorporated by reference in their entirety to the same extent as if each individual patent or publication were expressly and individually indicated to be incorporated by reference.

All of the articles and/or methods disclosed herein can be made and executed without undue experimentation in light of the present disclosure. While the articles and methods of this disclosure have been described in terms of preferred embodiments, it will be apparent to those of ordinary skill in the art that variations may be applied to the articles and/or methods and in the steps or in the sequence of steps of the methods described herein without departing from the concept, spirit and scope of the disclosure. All such similar substitutes and modifications apparent to those skilled in the art are deemed to be within the spirit, scope and concept of the disclosure.

As used in accordance with this disclosure, the following terms, unless otherwise indicated, shall be understood to have the following meanings.

The use of the terms "a" or "an" when used in conjunction with the term "comprising" may mean "one," but it is also consistent with the meaning of "one or more," at least one, "and" one or more than one. The use of the term "or" means "and/or" unless explicitly indicated to refer to alternatives only when the alternatives are mutually exclusive, although the present disclosure supports definitions only referring to alternatives and "and/or". In this application, the term "about" is used to indicate that a numerical value includes the inherent variation of error that quantifies the error in the means used to determine the value, or the subject of study. For example, and without limitation, when the term "about" is used, the specified value may vary by plus or minus 12%, or 11%, or 10%, or 9%, or 8%, or 7%, or 6%, or 5%, or 4%, or 3%, or 2%, or 1%. The use of the term "at least one" is to be understood to include one as well as any number greater than one, including, but not limited to, 1, 2, 3, 4, 5, 10, 15, 20, 30, 40, 50, 100, etc. The term "at least one" may extend to 100 or 1000 or more, depending on the term to which it is connected. Further, the amount of 100/1000 should not be considered limiting, as lower or upper limits may also produce satisfactory results. Further, use of the term "X, Y and at least one of Z" will be understood to include X alone, Y alone, and Z alone, as well as any combination of X, Y and Z. Ordinal terms (i.e., "first," "second," "third," "fourth," etc.) are used merely to distinguish two or more items and do not imply a sequence or order or importance, or any order of addition, of any one item relative to another item unless otherwise stated.

Reference herein to "one embodiment," or "one aspect," or "one version," or "one object," or "another embodiment," or "another aspect," or "another version," or "another object" of the invention may include one or more such embodiments, aspects, versions, or objects, unless the context clearly dictates otherwise.

The term "at least one" refers to one and any number greater than one, including but not limited to 1, 2, 3, 4, 5, 10, 15, 20, 30, 40, 50, 100, etc. The term "at least one" may extend to 100 or 1000 or more, depending on the term to which it is connected.

All percentages, parts, ratios and ratios used herein are by weight of the total composition, unless otherwise specified. Unless otherwise indicated. All such weights as they pertain to listed ingredients are based on the active ingredient, and therefore, do not include solvents or by-products that may be included in commercially available materials, unless otherwise specified.

All references to singular features or limitations of the present invention shall include the corresponding plural features or limitations and vice versa unless otherwise indicated or clearly implied to the contrary in the context in which the reference is made.

As used herein, a range of numbers is intended to include each number and subset of numbers subsumed within the range, whether or not specifically disclosed. Furthermore, these numerical ranges should be construed as providing support for a claim directed to any number or subset of numbers within the range.

As used herein, the words "comprising" (and any form of comprising, e.g., "comprises" and "comprising" in the plural), "having" (and any form of having, e.g., "has" in the plural and "having" in the singular), "including" (and any form of including, e.g., "includes" in the plural and "including" in the singular) or "containing" (and any form of containing, e.g., "contains" in the plural and "containing" in the singular) are inclusive or open-ended and do not exclude additional, unrecited elements or method steps. As used herein, the terms "or combinations thereof" and/or combinations thereof "refer to all permutations and combinations of the items listed prior to that term. For example, "A, B, C or a combination thereof" is intended to include at least one of: A. b, C, AB, AC, BC, or ABC, if the order is important in a particular context, also includes BA, CA, CB, CBA, BCA, ACB, BAC, or CAB. Continuing with this example, combinations containing repetitions of one or more items or terms are expressly included, such as BB, AAA, AAB, BBC, aaabccccc, CBBAAA, CABABB, and the like. The skilled person will appreciate that there is generally no limitation to the number of items or terms in any combination, unless it is clear from the context that this is not the case.

For the purposes of the following detailed description, other than in any operating examples, or where otherwise indicated, the numbers expressing quantities of ingredients used, for example, in the specification and claims are to be understood as being modified in all instances by the word "about". The numerical parameters set forth in the specification and attached claims are approximations that may vary depending upon the desired properties to be obtained by the practice of the present invention.

As used herein, the terms "or combinations thereof," "and combinations thereof," and "combinations thereof," refer to all permutations and combinations of the items listed prior to that term.

The term "about" refers to a range of values + 10% of the specified value. For example, the phrase "about 200" includes 10% of 200, or 180, 220.

The term "monomer" refers to a small molecule that is chemically bonded to one or more of the same or different types of monomers during polymerization to form a polymer.

The term "polymerization" or "polymerization" refers to a process in which monomeric compounds are chemically reacted to form polymer chains. The polymer chains may be alternating, block or random. The type of polymerization process may be selected from a variety of processes and includes the following non-limiting examples: polycondensation, step-wise polymerization, and free radical polymerization.

The term "macromolecule" refers to any large molecule, including polymers.

The term "polymer" refers to a macromolecule comprising one or more types of monomeric residues (repeating units) linked by covalent chemical bonds. Non-limiting examples of polymers include homopolymers and non-homopolymers such as copolymers, terpolymers, tetrapolymers, and higher analogs.

The term "heteroatom" refers to oxygen, nitrogen, sulfur, silicon, phosphorus, or halogen. The heteroatom may be present as part of one or more heteroatom-containing functional groups. Non-limiting examples of heteroatom-containing functional groups include ether, hydroxyl, epoxy, carbonyl, formamide, carboxylate, carboxylic acid, imine, imide, amine, sulfonic acid, sulfonamide, phosphonic acid, and silane groups. Heteroatoms may also be present as part of a ring, as in heteroaryl and heteroarylene groups.

The term "moiety" refers to a portion or functional group of a molecule.

The term "lactam" refers to a group having the structure:

wherein A is a functionalized or unfunctionalized alkylene or alkenylene group containing from 2 to 50 carbon atoms

Group and

2-4 carbon atoms are present in the lactam ring between the groups; r is selected from the group consisting of hydrogen, functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, any of which may or may not have heteroatoms.

The lactam-containing moiety may comprise a general lactam structure including beta-lactam, gamma-lactam, delta-lactam and epsilon-lactam. In one non-limiting embodiment, the lactam-containing moiety may comprise a lactam structure including beta-propiolactam, gamma-butyrolactam, delta-valerolactam, and epsilon-caprolactam.

The term "alkyl" refers to a functionalized or unfunctionalized monovalent linear, branched, or cyclic C1-C60 group optionally having one or more heteroatoms. Specifically, alkyl is a C1-C45 group, more specifically, a C1-C30 group. Specific but non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclobutyl, n-pentyl, isopentyl, cyclopentyl, n-hexyl, cyclohexyl, n-heptyl, cycloheptyl, methylcyclohexyl, n-octyl, 2-ethylhexyl, tert-octyl, isobornyl, n-dodecyl, tert-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, and n-eicosyl.

The term "branched and unbranched alkyl" refers to an alkyl group that may be straight-chain or branched. For example, the alkyl group has 1 to about 60 carbon atoms, more specifically, 1 to about 30 carbon atoms, and more specifically, 1 to about 6 carbon atoms. The branched group includes isopropyl group, tert-butyl group and the like.

The term "alkylene" refers to a divalent linear, branched or cyclic C, optionally functionalized or unfunctionalized, optionally with one or more heteroatoms₁-C₅₀A group. In particular, alkylene is C₁-C₄₅Radical and more particularly C₁-C₃₀A group. Specifically, non-limiting examples of alkylene groups include-CH₂–、–CH₂–CH₂–、–CH(CH₃)–CH₂–、–CH₂–CH(CH₃)–、–C(CH₃)₂–CH₂–、–CH₂–C(CH₃)₂–、–CH(CH₃)–CH(CH₃)–、–C(CH₃)₂–C(CH₃)₂–、–CH₂–CH₂–CH₂–、–CH(CH₃)–CH₂–CH₂–、–CH₂–CH(CH₃)–CH₂–、–CH₂–CH₂–CH(CH₃)–、–CH₂–CH₂–CH₂–CH₂–、–CH₂–CH₂–CH₂–CH₂–CH₂–、–CH₂–CH₂–CH₂–CH₂–CH₂–CH₂–、–CH₂–CH₂–CH₂–CH₂–CH₂–CH₂–CH₂-, cyclopropylene, cyclobutylene, cyclopentylene, cyclohexylene, etc.

The term "aryl" refers to a functional group derived from an aromatic hydrocarbon. The aromatic hydrocarbon may be mononuclear or polynuclear. Examples of mononuclear aryl groups include phenyl, tolyl, xylyl, mesityl, cumenyl, and the like. Examples of polynuclear aryl groups include naphthyl, anthryl, phenanthryl, and the like. The aryl group may have at least one substituent selected from halogen, hydroxy, cyano, carboxy, carbamoyl, nitro, amino, aminomethyl, lower alkyl, lower alkoxy, mercapto, trichloroethyl, or trifluoromethyl. Examples of such substituted aryl groups include 2-fluorophenyl, 3-nitrophenyl, 4-methoxyphenyl, 4-hydroxyphenyl, and the like.

The term "cycloalkyl" refers to a non-aromatic monocyclic or polycyclic ring system having about 3 to about 10 carbon atoms. The cycloalkyl group may be partially unsaturated. The cycloalkyl groups may also be substituted with alkyl substituents as defined herein. The cycloalkyl chain may contain oxygen, sulfur, or a substituted or unsubstituted nitrogen atom, where the nitrogen substituent may be hydrogen, alkyl, substituted alkyl, aryl, or substituted aryl, thereby providing a heterocyclic group. Representative monocyclic cycloalkyl rings include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and the like. Further, the cycloalkyl group may be substituted with a linking group such as alkyl, alkylene, etc., to form a cyclopropylmethyl group, a cyclobutylmethyl group, etc. The cycloalkyl group can also be a polycyclic cycloalkyl ring, such as adamantyl, octahydronaphthyl, decalin, camphor, bornane, and noradamantyl.

The term "functionalized" refers to a state of a moiety having one or more functional groups introduced by one or more functionalization reactions known to one of ordinary skill in the art. Specifically, non-limiting examples of functionalization reactions include epoxidation, sulfonation, hydrolysis, amidation, esterification, hydroxylation, dihydroxylation, amination, ammonolysis, acylation, nitration, oxidation, dehydration, elimination, hydration, dehydrogenation, hydrogenation, acetalization, halogenation, dehydrohalogenation, michael (michael) addition, aldol condensation, cannizzaro reaction, mannich reaction, krassen (claisen) condensation, suzuki coupling, and the like. Specifically, functionalization of a moiety replaces one or more hydrogens in the moiety with one or more non-hydrogen groups (e.g., alkyl, alkoxy, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, and/or aryl). Specific, but non-limiting, examples of cycloalkyl groups include cyclopentane, cyclohexane, cycloheptane, and the like. Specific, but non-limiting examples of alkoxy groups include methoxy, ethoxy, n-propoxy, isopropoxy, and the like. Specific, but non-limiting, examples of aryl groups include benzene, naphthalene (2 rings), anthracene (3 rings), and the like.

The terms "pharmaceutically acceptable" and "cosmetically acceptable" refer to molecular entities and compositions that are generally considered safe. In particular, as used herein, the terms "pharmaceutically acceptable" and "cosmetically acceptable" refer to those approved by the regulatory agency of the appropriate governmental agency or listed in the U.S. pharmacopoeia (u.s.pharmacopoeia) or other generally recognized pharmacopoeia for use in animals, and more particularly in humans.

The term "pharmaceutically active ingredient" refers to any ingredient that is considered to have a therapeutic effect when delivered to a subject in need thereof and is regulated by pharmaceutical authorities such as CDER, EMEA, TAG, and the like. The pharmaceutically active ingredient may be administered orally for systemic effect or for topical use, for example when present in the mouth, skin, etc. They may also be delivered through the skin as in transdermal drug delivery systems.

All percentages, ratios, and proportions used herein are by weight unless otherwise specified.

The present disclosure relates to polymers obtained from a reaction mixture comprising (i) at least one dihydroxylactam moiety and (ii) at least one functional moiety having a hydroxyl-reactive functional group; wherein the amounts of (i) and (ii) are independently about 0.01 mole% to about 99.99 mole%, and the polymer is selected from the group consisting of polyesters, polycarbonates, polyethers, polyester ethers, polyester amides, polyimides, polyamides, polyacrylates, and polyesterimides; or wherein (i) and (ii) are each present in an amount other than 50 mol% and the polymer is a polyurethane.

According to one embodiment, the dihydroxylactam moiety has the structure:

wherein "R" is independently selected from the group consisting of hydrogen, functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, any of which may or may not have heteroatoms and which may be straight or branched;

"A" is an alkylene or alkenylene group containing 2 to 50 carbon atoms; wherein, in

Group and

between the groups 2-4 carbon atoms are present in the lactam ring;

"n" is an integer between 1 and 55; "m" is an integer between 0 and 5.

More specifically, A in each lactam is in

Group and

the groups can be independently selected from the group consisting of:

more specifically, A in each lactam is in

Group and

between the radicals may each independently be

-CH₂-CH₂-or-CH₂-CH₂-CH₂-CH₂-.

More specifically, each R may be independently selected from the group consisting of hydrogen, functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups containing 1-10 carbon atoms, any of which may or may not have heteroatoms. More specifically, each R may contain 1 to 8 carbon atoms. Most particularly, each R may contain 1 to 6 carbon atoms.

Non-limiting examples of said dihydroxylactam moiety include

Wherein n is an integer between 1 and 6, and "m" is an integer between 0 and 6.

According to one embodiment, the dihydroxylactam moiety compound is selected from the group consisting of N- (2, 3-dihydroxypropyl) -2-pyrrolidone, 1- [2- (2, 3-dihydroxypropoxy) ethyl ] -2-pyrrolidone, and combinations thereof.

According to another embodiment, the dihydroxylactam moiety compound is present in an amount from about 0.01% to about 99.99% by weight of the total reaction mixture. In another embodiment, other possible ranges for the dihydroxylactam moiety compound include, but are not limited to, about 0.1 wt.% to about 10 wt.%; about 10 wt.% to about 20 wt.%; about 20 wt.% to about 30 wt.%; about 30 wt.% to about 40 wt.%; about 40 wt.% to about 50 wt.%; about 50 wt.% to about 60 wt.%; about 60 wt.% to about 70 wt.%; about 70 wt.% to about 80 wt.%; about 80 wt.% to about 90 wt.%; or about 90 wt.% to about 99.99 wt.%.

According to one embodiment, the functional moiety having a hydroxyl-reactive functional group is selected from the group consisting of: (a) carbamates, (b) acyl halides, (c) sulfonyl halides, (d) isothiocyanates, (e) cyanoacrylates, (f) isocyanates, (g) oxiranes, (h) imines, (i) thiocarbonates, (j) thiols, (k) aldehydes, (l) aziridines, (m) acids and their anhydrides, (n) azides, (o) phosphorus halides and alcohols, (p) esters, (q) amines, (r) haloalkanes,(s) dihalomethanes, and combinations thereof.

According to another embodiment, the carbamate is selected from the group consisting of hydroxyethyl carbamate, hydroxypropyl carbamate, hydroxybutyl carbamate, and combinations thereof.

According to one embodiment, the acyl halide compound is selected from the group consisting of acryloyl chloride, succinyl chloride, methacryloyl chloride, crotonyl chloride, benzoyl chloride, cinnamoyl chloride, hydrocinnamoyl chloride, acetyl chloride, 2-acetoxyacetyl chloride, diphenylacetyl chloride, 2-methoxybenzoyl chloride, 3,4,5 trimethoxybenzoyl chloride, 3,4 (methylenedioxy) benzoyl chloride, cyclopropanecarbonyl chloride, pentadecenyl chloride, 2-cyclohexene-1-carbonyl chloride, 2-thiopheneacetyl chloride and combinations thereof.

According to another embodiment, the sulfonyl halide compound is selected from the group consisting of methanesulfonyl chloride, benzenesulfonyl chloride, and combinations thereof.

According to another embodiment, the isothiocyanate compound is selected from the group consisting of methyl isothiocyanate, allyl isothiocyanate, aryl isothiocyanate and combinations thereof.

According to another embodiment, the cyanoacrylate compound is selected from the group consisting of ethyl cyanoacrylate, N-butyl-cyanoacrylate (NBCA), 2-octyl cyanoacrylate (2-OCA), and combinations thereof.

According to another embodiment, the isocyanate compound is selected from the group consisting of: hexamethylene diisocyanate, Toluene Diisocyanate (TDI), diphenylmethane diisocyanate (MDI), m-phenylene diisocyanate, p-phenylene diisocyanate, xylene diisocyanate, cyclohexane diisocyanate (CHDI), bis (isocyanatomethyl) cyclohexane (H6XDI), dicyclohexylmethane diisocyanate (H12MDI), dimer acid diisocyanate (DDI), trimethylhexamethylene diisocyanate, lysine diisocyanate and its methyl ester, isophorone diisocyanate, methylcyclohexane diisocyanate, 1, 5-naphthalene diisocyanate, xylene and xylene diisocyanate and their methyl derivatives, polymethylene polyphenyl isocyanates, chlorobenzene-2, 4-diisocyanate, polyphenylene diisocyanate, isophorone diisocyanate (IPDI), Hydrogenated Methylene Diphenyl Isocyanate (HMDI), Tetramethylxylene diisocyanate (TMXDI), Hexamethylene Diisocyanate (HDI), and their respective dimers, trimers, and oligomers, and combinations thereof.

According to another embodiment, the oxirane compound is selected from the group consisting of: ethylene Oxide (EO), Propylene Oxide (PO), butylene oxide, 1-octene oxide, cyclohexene oxide, styrene oxide, bisphenol A diglycidyl ether, epichlorohydrin, glycidic acid, allyl glycidyl ether ([ (2-propenyloxy) methyl ] -oxirane), glycidyl (meth) acrylate, vinylcyclohexene diepoxide, 3, 4-epoxycyclohexylmethyl 3, 4-epoxycyclohexane carboxylate, 3, 4-epoxy-6-methylcyclohexylmethyl 3, 4-epoxy-6-methylcyclohexane carboxylate, dipentene dioxide, 2- (3, 4-epoxycyclohexyl-5, 5-spiro-3, 4-epoxy) cyclohexane-dioxane, and combinations thereof.

According to another embodiment, the imine compound is selected from the group consisting of polyaldimines, hydroxyaldimines, polyketimines, hydroxyketimines, and combinations thereof.

According to another embodiment, the thiocarbonate compound is selected from the group consisting of bis- (phenylthiocarbonyloxymethyl) ester, bis- (isopropylthiocarbonyloxymethyl) ester, and combinations thereof.

According to another embodiment, the thiol compound is selected from the group consisting of glutathione, 3-acetylthiolpropanic acid, thioanhydride, thioacid, and combinations thereof.

According to another embodiment, the aldehyde compound is selected from the group consisting of acetaldehyde diethyl acetal, propionaldehyde diethyl acetal, di (acetaldehyde diethyl acetal), chloroacetaldehyde diethyl acetal, and combinations thereof.

According to another embodiment, the aziridine compound is selected from the group consisting of 2, 2-bishydroxymethylbutanoic acid tris [3- (1-aziridinyl) propionate ], bis-N-aziridinemethane, and combinations thereof.

According to another embodiment, the acid and anhydride compound thereof is selected from the group consisting of maleic acid, maleic anhydride, fumaric acid, citric acid, alkenyl succinic anhydride, phthalic anhydride, terephthalic acid, succinic anhydride, tetrahydrophthalic anhydride, maleic anhydride copolymers, and combinations thereof.

According to another embodiment, the azide compound is selected from the group consisting of azide-functionalized DNA, azide-functionalized peptides, azide-functionalized proteins, azide-functionalized sugars, azide-functionalized metals, azide-functionalized nanoparticles, azide-functionalized antimicrobial agents, 4 '-diazide stilbene-2, 2' -disulfonic acid sodium, aromatic bis-azide compounds, calcium azide, 4-diphenyl disulfonyl azide, and p-toluenesulfonyl azide, and combinations thereof.

According to another embodiment, the phosphorus oxyhalide compound is selected from the group consisting of phosphorus oxychloride, phosphorus oxybromide, and combinations thereof.

According to another embodiment, the ester compound is selected from the group consisting of dimethyl itaconate, di-n-butyl itaconate, vinyl hexanoate, glycolide, epsilon-caprolactone, gamma-caprolactone, poly (D, L-lactide), poly (D-lactide), poly (L-lactide), poly (epsilon-caprolactone), poly (gamma-caprolactone), polyglycolide, valerolactone, butyrolactone, polyether-polyesters, polyanhydride-glycol-polyesters, and combinations thereof.

According to another embodiment, the amine compound is selected from the group consisting of amino alcohols, methyl amines, ethyl amines, hexyl amines, isopropyl amines, isobutyl amines, pentyl amines, cyclohexyl amines, octyl amines, benzyl amines, dimethyl amines, diethyl amines, dipropyl amines, dibutyl amines, diphenyl amines, dibenzyl amines, ethyl methyl amines, N-methyl anilines, ethylene diamines, propylene diamines, butylene diamines, hexamethylene diamines, cyclohexyl diamines, piperazine, toluene diamines, isophorone diamine, N-dimethyl anilines, N-dimethyl-1-naphthylamines, N-dimethyl p-toluidine, N-diethyl anilines, N-diallyl anilines, 1-phenyl piperidine and 4-phenyl morpholine, amino ethoxylates, coconut oil saddles, soy amines and combinations thereof.

According to another embodiment, the alkyl halide compound is selected from the group consisting of bromohexane, bromododecane, bromohexadecane, 1-bromooctadecane, and combinations thereof.

According to another embodiment, the dihalomethane compound is selected from the group consisting of dibromomethane, methylene chloride, and combinations thereof.

According to yet another embodiment, the functional moiety having a hydroxyl-reactive functional group is present in an amount of about 0.01 wt.% to about 99.99 wt.% based on the weight of the total reaction mixture. In another embodiment, other possible ranges for functional moieties having hydroxyl reactive functional groups include, but are not limited to, about 0.1 wt.% to about 10 wt.%; about 10 wt.% to about 20 wt.%; about 20 wt.% to about 30 wt.%; about 30 wt.% to about 40 wt.%; about 40 wt.% to about 50 wt.%; about 50 wt.% to about 60 wt.%; about 60 wt.% to about 70 wt.%; about 70 wt.% to about 80 wt.%; about 80 wt.% about 90 wt.%; about 90 wt.% to about 99.99 wt.%.

The present disclosure also relates to polymers obtained from a reaction mixture comprising (i)0.01 mol% to about 99.99 mol% of at least one dihydroxylactam moiety, and (ii)0.01 mol% to about 99.99 mol% of at least one functional moiety having a hydroxyl-reactive functional group; wherein the polymer is selected from the group consisting of polyesters, polycarbonates, polyethers, polyester ethers, polyesteramides, polyimides, polyamides, polyacrylates, and polyesterimides; or wherein (i) and (ii) are each present in an amount other than 50 mol% and the polymer is a polyurethane.

According to another embodiment, the reaction mixture further comprises one or more non-lactam moieties.

According to another embodiment, the non-lactam moiety is selected from the group comprising the following functionalized/unfunctionalized compounds: carbon chain length of C₁-C₁₈Aliphatic/aromatic alcohol of carbon chain length C₁-C₁₈Alkoxylated alcohol-C18, ethylene glycol, methyl (acrylate) alcohol, polyvinyl alcohol, polycarbonate polyols, polybutylene glycol, polyethylene glycol, polypropylene glycol, hydroxyl polyesters, hydroxyl polyethers, hydroxyl polythioesters, hydroxyl polyacetals, hydroxyl polycarbonates, polyether polyols, polycarbonate polyether polyols, hydroxyl polythioesters, hydroxyl polythiols, hydroxyl polycarbonates, aliphatic and aromatic polyether polyols, caprolactone polyols, poly (ethylene glycol) soyamines, poly (ethylene glycol) castor oil, poly (ethylene glycol) hydrogenated castor oil, poly (ethylene glycol) lanolin wax, poly (ethylene glycol) polyvinylidene fluoride, poly (ethylene glycol) poly (vinyl acetate), poly (ethylene glycol) polyoxymethylene, poly (ethylene glycol) esters, and combinations thereof.

According to another embodiment, the non-lactam moiety compound is present in an amount of about 0.01% to about 99.98% by weight of the total reaction mixture. In another embodiment, other possible ranges of non-lactam moieties include, but are not limited to, about 0.1 wt.% to about 10 wt.%; about 10 wt.% to about 20 wt.%; about 20 wt.% to about 30 wt.%; about 30 wt.% to about 40 wt.%; about 40 wt.% to about 50 wt.%; about 50 wt.% to about 60 wt.%; about 60 wt.% to about 70 wt.%; about 70 wt.% to about 80 wt.%; about 80 wt.% to about 90 wt.%; or about 90 wt.% to about 99.98 wt.%.

The molecular weight of the dihydroxylactam-functionalized polymer is from about 3,000g/mol to about 1,000,000 g/mol. Other preferred molecular weight ranges include, but are not limited to, from about 10,000g/mol to about 100,000 g/mol; about 100,000g/mol to about 200,000 g/mol; about 200,000g/mol to about 300,000 g/mol; about 300,000g/mol to about 400,000 g/mol; about 400,000g/mol to about 500,000 g/mol; about 500,000g/mol to about 600,000 g/mol; about 600,000g/mol to about 700,000 g/mol; about 700,000g/mol to about 800,000 g/mol; about 800,000g/mol to about 900,000 g/mol; and/or from about 900,000g/mol to about 1000,000 g/mol.

The present disclosure also relates to polymers obtained from a reaction mixture comprising (i) N- (2, 3-dihydroxypropyl) -2-pyrrolidone and/or 1- [2- (2, 3-dihydroxypropoxy) ethyl ] -2-pyrrolidone, and (ii) poly (D, L-lactide); wherein the amounts of (i) and (ii) are independently about 0.01 mol% to about 99.99 mol%, and the polymer is a polyester.

The present disclosure also relates to polymers obtained from a reaction mixture comprising (i) N- (2, 3-dihydroxypropyl) -2-pyrrolidone and/or 1- [2- (2, 3-dihydroxypropoxy) ethyl ] -2-pyrrolidone, and (ii) a) isophorone diisocyanate, b) polyethylene glycol, and optionally c) octanol; wherein (i) and (ii) are each present in an amount other than 50 mol% and the polymer is a polyurethane.

Types of polymerization processes for preparing the polymers of the present invention include, but are not limited to, polycondensation, step-wise polymerization, and free radical polymerization.

By reacting: (i) at least one dihydroxylactam moiety, and (ii) at least one functional moiety having a hydroxyl-reactive functional group; wherein the amounts of (i) and (ii) are independently about 0.01 to about 99.99 mole% and the polymer is selected from the group consisting of polyesters, polycarbonates, polyethers, polyester ethers, polyester amides, polyimides, polyamides, polyacrylates, and polyesterimides; or wherein (i) and (ii) are each present in an amount other than 50 mol%, and the polymer is a polyurethane, non-limiting illustrative examples of structures of the polymers of the invention prepared include the following:

polyisocyanates based on PDIOL-DIOL-diisocyanate:

wherein x + y + z is 100.

Polyisocyanate based on EPDIOL-DIOL-diisocyanate:

wherein x + y + z is 100.

Polyisocyanate based on EPDIOL-DIOL-diisocyanate-alcohol:

wherein x + y + z is 100; and the alcohol may be hexanol.

Polyisocyanate based on EPDIOL-DIOL-DMPA-diisocyanate-alcohol:

wherein x + y + z + w ═ 100 and the alcohol may be ethanol.

The present disclosure also relates to compositions comprising: (I) a polymer obtained from a reaction mixture comprising: (i) at least one dihydroxylactam moiety, and (ii) at least one functional moiety having a hydroxyl-reactive functional group; wherein the amounts of (i) and (ii) are independently about 0.01 mole% to about 99.99 mole%, and the polymer is selected from the group consisting of polyesters, polycarbonates, polyethers, polyester ethers, polyester amides, polyimides, polyamides, polyacrylates, and polyesterimides; or wherein (i) and (II) are each present in a content other than 50 mol% and the polymer is a polyurethane, and (II) one or more additives.

According to one embodiment, the additive may be used in an application selected from the group consisting of: adhesives, aerosols, agricultural agents, anti-soil redeposition agents, batteries, beverages, biocides, biomaterials, adhesives and construction agents, cleaning agents, paints and coatings, rheology modifiers, conductive materials, cosmetic agents, dental agents, decorative pigments, detergents, dispersants, pharmaceuticals, electronics, packaging, food, hair care agents, home industry institutional agents, inks and coatings, interlayers, lithographic printing solutions, film additives, metal working fluids, oilfield agents, paper sizing agents, polishes, personal care agents, pharmaceuticals, pigment additives, gypsum, plastics, textiles, lubricants, printing, refractive index modifiers, chelants, soil release agents, static control agents, and wood care agents.

The compounds, monomers, and polymers described herein can be used alone or in combination with other ingredients in various compositions and product forms. Such compositions include, but are not limited to, adhesives, aerosols, agricultural compositions, anti-soil redeposition compositions, batteries, beverage compositions, biocide compositions, biomaterial compositions, cement and construction compositions, cleaning compositions, paint and coating compositions, rheology modifier compositions, conductive material compositions, cosmetic compositions, dental compositions, decorative pigment compositions, detergent compositions, dispersant compositions, electronic application compositions, encapsulating polymer compositions, food compositions, hair care compositions, home and industrial establishment compositions, inks and coating compositions, interlayer compositions, photolithography application compositions, film compositions, metalworking fluid compositions, oil field compositions, paper size compositions, polishing compositions, personal care compositions, pharmaceutical compositions, gypsum compositions, plastic additive compositions, water-soluble polymers, and water-soluble polymers, and water-soluble polymers, and water-soluble polymers, water-soluble polymers, Textile compositions, lubricant compositions, printing compositions, refractive index modifier compositions, chelant compositions, soil release compositions, static control agents, and wood care compositions.

The term "personal care composition" refers to compositions intended for use on or in the human body. Non-limiting but specific types of personal care compositions include hair care compositions (including styling and non-styling compositions), sunscreen compositions (including after-sun compositions), skin care compositions, and oral care compositions.

The personal care composition may be formulated into any product form known to one of ordinary skill in the art. Non-limiting product forms are described below.

The product form is as follows:

non-limiting hair care product forms include: shampoos, conditioners, aerosols, mousses, sprays, mists, gels, waxes, creams, emulsions, glues, pomades, sprays, solutions, oils, liquids, solids, W/O emulsions, O/W emulsions, suspensions, multiple emulsions, microemulsions, microcapsule products, sticks, balms, tonics, pastes, reconstitutable products, nanoemulsions, solid lipid nanoparticles, liposomes, cubes, niosomes, putties, lacquers, essences, perms, volumizers, packaging, wafers, two-in-one shampoo/conditioner products, and three-in-one shampoo/conditioner/styling products.

The compositions according to the invention may also take the form of post-shampoo compositions, with or without rinsing, for perming, straightening, curling, dyeing or bleaching, or of rinse-off compositions before or after coloring, bleaching, perming, straightening, relaxing, curling or even between the two stages of perming or straightening.

Non-limiting sunscreen product forms include: solutions, liquids, creams, powders, emulsions, gels, pastes, waxes, aerosols, sprays, mists, roll-ons, sticks, emulsions, and wipes.

Non-limiting skin care product forms include: solutions, oils, emulsions, creams, ointments, liquids, gels, solids, W/O emulsions, O/W emulsions, suspensions, microemulsions, dispersions, microencapsulated products, sticks, balms, tonics, pastes, mists, reconstitutable products, fruit peels, soaps, aerosols, mousses, waxes, glues, pomades, sprays, putties, varnishes, essences, perms, powders, pencils, flakes, blushes, highlighters, bronzes, concealers, and 2-way cake products.

The compositions of the invention may also take the form of skin cleansing compositions, in particular solutions or gels for use in the bath or shower, or make-up removal products.

The following non-limiting six skin care product categories can be considered a subset of skin care and sunscreen products:

(1) eye nursing:

non-limiting forms of eye care products include: mascara, eyeliner, eye shadow, eyelash clip, eyebrow pencil, and eyeliner.

(2) Lip care:

non-limiting lip care product forms include: lipstick sticks, lipsticks, lip pencils, lip glosses, lip sprays, clear lip bases, colored lip moisturizers, and multi-functional color sticks that can also be used on the cheeks and eyes.

(3) Nail care:

non-limiting nail care product forms include: nail polishes, enamels, nail polish removers, household nail products such as cuticle softeners and nail enhancers, and artificial nails.

(4) And (3) face care:

non-limiting facial care product forms include: creams, lotions, solutions, oils, liquids, peels, scrubs, emulsions, suspensions, microemulsions, microencapsulated products, pastes, reconstitutable products, aerosols, mousses, gels, waxes, glues, pomades, sprays, facial wipes, putties, paints, essences, perms, dusting powders, blushes, highlighters, bronzes, masks and concealers.

(5) And (3) body care:

non-limiting body care product forms include: foams, peels, masks, gels, sticks, aerosols, emulsions, salts, oils, spheres, liquids, powders, peels, pearls, bar soaps, liquid soaps, body washes, cleansers, scrubs, creams, wafers, other bath and shower products, shaving products, waxing products, and disinfectants.

(6) And (3) foot nursing:

non-limiting forms of footcare products include: mousses, creams, lotions, powders, liquids, sprays, aerosols, gels, flakes and scrubs.

Non-limiting oral care product forms include: toothpastes, binders, gums, gels, powders, creams, solutions, lotions, liquids, dispersions, suspensions, emulsions, tablets, capsules, rinses, flosses, aerosols, strips, films, pads, bandages, microencapsulated products, syrups, and lozenges.

Personal care compositions comprising the polymers described herein complexed with iodine are also contemplated. These compositions are useful for treating skin disorders, non-limiting examples of which include dermatitis, wounds, bacterial infections, burns, rashes, and herpes. These complex compositions may be dyed, substantially undyed, or substantially undyed.

Examples of related personal care compositions are disclosed in the following patents: U.S. patent nos. 5,599,800; 5,650,166, respectively; 5,916,549, respectively; and 6,812,192; U.S. patent application 2009/0317432; EP 556,660; 661,037, respectively; 661,038, respectively; 662,315, respectively; 676,194, respectively; 796,077, respectively; 970,682, respectively; 976383, respectively; 1,415,654, respectively; and 2,067,467; and WO 2005/032506; each of which is hereby incorporated by reference in its entirety.

It is also contemplated that the personal care compositions may be used in products for personal grooming and/or toileting of men and/or women, such as: sanitary napkins, baby diapers, adult diapers, feminine products, incontinence products, and other related products.

The present disclosure also relates to coating compositions comprising the dihydroxylactam-based polymers as described above. The coating composition may further comprise at least one coating agent selected from the group consisting of solvents/co-solvents, secondary rheology modifiers, thixotropic agents, binders, cross-linking agents, pH modifiers, pigments/fillers, flow control agents, gloss control agents, coalescing agents, toughening resins, surfactants, waxes, wetting agents, dispersants, plasticizers, antioxidants, ultraviolet radiation absorbers, biocides, extenders, colorants, adhesion promoters, defoaming/antifoaming agents, drying agents, matting agents, and combinations thereof.

Examples of the pigment/filler may include, but are not limited to, calcium carbonate, mica, barium sulfate, lithopone, zinc oxide, zinc sulfide, titanium dioxide (anatase, rutile), chalk, precipitated calcium carbonate, calcite, dolomite, silica, silicic acid, silica fume, pyrogenic silicic acid, precipitated silicic acid, silicates, talc, kaolin, barium sulfate, magnesium silicate, lead oxide, barite, white mortar, sand, and glass beads. Specific pigments/fillers may include graphene, graphite, carbon nanotubes, carbon, copper, silver, nanosilver, titanium nanotubes, specially decorated inorganic particles and structures, and the like.

Non-limiting examples of such solvents/co-solvents can include, but are not limited to, aromatic hydrocarbon solvents such as benzene, toluene and xylene, ethylbenzene, cumene, alcohols (ethylene glycol monobutyl ether, ethylene glycol monomethyl ether, diethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, hexanol, octanol, ethanol, isopropanol, butanol, n-butanol, ethylene glycol, diethylene glycol), ketones (acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone), diacetone alcohol, dimethylformamide, n-methyl-2-pyrrolidone, butyrolactone, ethyl acetate, butyl propionate, water, and the like.

Non-limiting examples of the binder may include, but are not limited to, latex emulsion polymers, which are polymerization products of one or more ethylenically unsaturated monomers. Examples of ethylenically unsaturated monomers may include, but are not limited to, acrylic acid, acrylonitrile, acetoacetoxyethyl methacrylate, acetoacetoxyethyl acrylate, butyl acrylate, butadiene, butyl methacrylate, butyl acrylamide, chloromethylstyrene, crotonic acid, ethyl acrylate, ethylacrylamide, ethylene, ethyl methacrylate, ethylhexyl acrylate, 2-ethylhexyl methacrylate, glycidyl methacrylate, hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, isobutyl methacrylate, isoprene, isooctyl acrylate, isooctyl methacrylate, itaconic acid, methyl acrylate, octyl methacrylate, methyl methacrylate, methacrylic acid, alpha-methylstyrene, alpha-methyl styrene, alpha-ethyl acrylate, alpha-butyl acrylate, alpha-ethyl acrylate, or alpha-ethyl acrylate, alpha-butyl acrylate, or alpha-methyl acrylate, or alpha-butyl acrylate, or alpha-methyl acrylate, or alpha-acrylate, or the like, Styrene, vinyl chloride, vinyl naphthalene, vinyl toluene, vinylidene chloride, vinyl acetate, and the like.

Other adhesives used in the present disclosure may include, but are not limited to, alkyd resins, polyurethane resins, epoxy resins, and the like. Alkyd resins are generally composed of a polyacid, a polyol, and a fatty acid which may be unsaturated. Such as aromatic, aliphatic and alicyclic saturated and unsaturated compounds, such as adipic acid, chlorendic acid, pimelic acid, isophthalic acid, maleic acid, naphthoic acid, phthalic acid, sebacic acid, succinic acid, trimellitic acid, terephthalic acid, and tetrahydrophthalic acid. The polyol component includes 1, 3-butanediol, diethylene glycol, dipentaerythritol, dipropylene glycol, ethylene glycol, glycerol, 1, 6-hexanediol, neopentyl glycol, pentaerythritol, propylene glycol, sorbitol, trimethylolethane, trimethylolpropane and triethylene glycol. Fatty acids used in the manufacture of alkyd resins typically include dehydrated castor oil, coconut oil, cottonseed oil, fish oil, linseed oil, tung oil, safflower oil, soybean oil, tall oil acid, and the like.

The polyurethane resin is formed from a polyisocyanate (aliphatic, aromatic, or a combination thereof) compound. Examples of the aliphatic isocyanate include butane diisocyanate, 4' -diisocyanatodicyclohexylmethane, hexamethylene diisocyanate, hexahydroxylylene diisocyanate (hexahydroxyylene diisocyanate), isophorone diisocyanate, 1-methyl-2, 4(2,6) -diisocyanatocyclohexane, norbornane diisocyanate, and tetramethylxylene diisocyanate. Examples of aliphatic and aromatic isocyanates include 4,4' -biphenyl diisocyanate, 4-chloro-1, 3-phenylene diisocyanate, 1, 4-cyclohexyldiisocyanate, 1, 10-decaethylene diisocyanate, methylenebis- (4-phenylisocyanate), 4, 4-methylenebis (cyclohexylisocyanate), 1, 5-naphthalene diisocyanate, 1, 3-phenylene diisocyanate, 2, 4-toluene diisocyanate, 2, 6-toluene diisocyanate, 1, 4-tetramethylene diisocyanate, 1, 5-tetrahydronaphthalene diisocyanate, and the like.

In addition to isocyanates, the alcohols and carboxylic acids that form the polyester composition may also be used to prepare polyurethane resins. The carboxylic acids may be aliphatic, cycloaliphatic, aromatic and/or heterocyclic in nature and may contain halogen atoms and/or unsaturated moieties. Suitable acids include adipic acid, azelaic acid, bis (ethylene) terephthalate, dimer fatty acids, dimethyl terephthalate, endomethylene tetrahydrophthalic anhydride, fumaric acid, glutaric anhydride, hexahydrophthalic anhydride, isophthalic acid, maleic anhydride, phthalic acid, suberic acid, succinic acid, sebacic acid, tetrahydrophthalic anhydride, and tetrachlorophthalic anhydride. Examples of the alcohols include 1,4-, 1, 3-and 2, 3-butanediol, cyclohexanedimethanol (1, 4-bis-hydroxymethylcyclohexane), diethylene glycol, dipropylene glycol, dibutylene glycol, ethylene glycol, 1, 2-and 1, 3-propanediol, 1, 6-hexanediol, 2-methyl-1, 3-propanediol, neopentyl glycol, 1, 8-octanediol, polyethylene glycol, polypropylene glycol, polybutylene glycol, triethylene glycol and tetraethylene glycol. Diols comprising carboxyl or carboxylate groups suitable for supporting ionic or potentially ionic groups are contemplated. These moieties may be composed of dihydroxysuccinic acid, dimethylolacetic acid, 2-dimethylolpropionic acid, 2-dimethylolbutyric acid and 2, 2-dimethylolpentanoic acid.

Polyester compositions may also be prepared as part of the present invention. Polyesters containing carboxyl groups and terminal carboxyl groups are contemplated. Furthermore, polyesters composed of lactones are also envisaged. A polyester obtained from a reaction mixture comprising at least one dihydroxylactam moiety and at least one functional moiety having a hydroxyl-reactive functional group, wherein the functional moiety having a hydroxyl-reactive functional group is selected from the group consisting of phthalic anhydride, isophthalic acid, maleic anhydride, chlorine/bromine-containing anhydrides, and fumaric acid. The polyester may further comprise one or more non-lactam moieties selected from the group consisting of aliphatic/aromatic alcohols having a carbon chain length of C1-C18, alkoxylated alcohols of alcohols having a carbon chain length of C1-C18, ethylene glycol, hydroxymethyl (acrylate), polyvinyl alcohol, polycarbonate polyols, polybutylene glycols, polyethylene glycols, polypropylene glycols, hydroxyl polyesters, hydroxyl polyethers, hydroxyl polythioesters, hydroxyl polyacetals, hydroxyl polycarbonates, polyether polyols, polycarbonate polyols, hydroxyl polyesters, hydroxyl polyethers, hydroxyl polythioesters, hydroxyl polyacetals, hydroxyl polycarbonates, aliphatic and aromatic polyether polyols, caprolactone-based polyols, poly (ethylene glycol) -soya amines, poly (ethylene glycol) -castor oil, poly (ethylene glycol) -hydrogenated castor oil, poly (ethylene glycol) -lanolin, poly (ethylene glycol) fatty acid esters, poly (ethylene glycol) -fatty acid esters, poly (ethylene glycol) fatty acid esters, poly (ethylene glycol) fatty acid esters, poly (ethylene glycol) s, poly (ethylene glycol esters, poly (ethylene glycol) s, poly (ethylene glycol esters, poly (ethylene glycol) s, poly (ethylene glycol esters, and/or mixtures of fatty acid esters, and/or mixtures of fatty acids, and/or mixtures of a mixture (ethylene glycol) s, and/or mixtures of a mixture (ethylene glycol esters of a mixture (ethylene glycol) s, and/or mixtures of a mixture (ethylene glycol) and/or mixtures of a mixture (s, Poly (ethylene glycol) -lanolin wax, poly (ethylene glycol) -polyvinylidene fluoride, poly (ethylene glycol) -poly (vinyl acetate), poly (ethylene glycol) -polyoxymethylene, poly (ethylene glycol) -ester, and combinations thereof.

Polycarbonates containing hydroxyl groups are useful, and can be prepared by reacting diols with dicarbonates, such as diphenyl carbonate or phosgene.

Polyethers containing diols formed from polymers derived from ethylene oxide, propylene oxide, and/or tetrahydrofuran are also useful. Amine functionality can be used to introduce terminal hydroxyl functionality, such as diethanolamine, ethanolamine, N-methylethanolamine, propanolamine, N, N, N' -tris-2-hydroxyethylethylenediamine.

The epoxy resin is composed mainly of straight-chain molecules. These molecules are formed by reacting bisphenols with halohydrins to epoxy resins containing epoxy groups. Common bisphenols include bisphenol-A, bisphenol-F, bisphenol-S, and 4,4' -dihydroxy bisphenol. Common halogenated alcohols include epichlorohydrin, dichloropropanol and 1, 2-dichloro-3-hydroxypropane. Examples of commercially available epoxy resins include d.e.r.tm333 and d.e.r.tm661 from Dow Chemical Company; EPONTM828, EPONTM836, and EPONTM1001 by Momentive Specialty Chemicals inc; Ciba-Geigy epoxy resins GT-7013, GT-7014, GT-7074, GT-259 from Huntsman; and Ancarez AR 555, Air Products.

Non-limiting examples of such secondary rheology modifiers may include cellulose and cellulose derivatives, guar gum and guar gum derivatives, modified ureas, polyurethane thickeners and associative thickeners, Alkali Swelling Emulsions (ASE), hydrophobically modified alkali swelling emulsions (HASE), hydrophobically modified polyurethanes (HEUR), Hydrophobically Modified Polyethers (HMPE), attapulgite, hydrophobically modified polyacetal polyethers (HMPAPE), acrylate thickeners, amides and organic derivatives, fumed silica, synthetic layered silicates, organoclays, mixed minerals, thixotropic accelerators, polyalkylene ether derivatives, starches, polyacrylates, and the like.

Non-limiting examples of the pH modifier may include, but are not limited to, monoethanolamine, triethanolamine, methylaminoethanol, 2-amino-2-methyl-1-propanol, 2- (n-butylamino) ethanol, ammonium hydroxide, ammonia, caustic alkali, potassium hydroxide, formic acid, acetic acid, citric acid, organic acids, inorganic acids, hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, and the like.

Non-limiting examples of the biocide may include, but are not limited to, 2-n-octyl-3-isothiazolinone, chlorothalonil, carbendazim, diuron, isothiazolinone, 2-octyl-2H-isothiazolin-3-One (OIT), iodopropynyl butyl carbamate (IPBC), sodium 2-pyridinethiol-1-oxide, zinc 2-pyridinethiol-1-oxide, 1, 2-dibromo-2, 4-dicyanobutane, 2- (4-thiazolyl) benzimidazole, thiabendazole, tebuconazole, methylenebis (thiocyanate), 2- (thiocyanomethylthio) benzothiazole, octreone, barium metaborate, propiconazole, diiodomethyl-p-tolyl sulfone, 3-iodo-2-propynyl butyl carbamate, n- (trichloromethylthio) phthalimide, tributyltin benzoate, alkylamine hydrochloride, n-trichloromethylthio-4-cyclohexene-1, 2-dicarboximide, 2-methylthio-4-tert-butylamino-6-cyclopropylamino-s-triazine, tetrachloroisophthalonitrile, zinc dimethyldithiocarbamate, zinc 2-mercaptobenzothiazole, trans-1, 2-bis (n-propylsulfonyl) ethane, 4, 5-dichloro-2-n-octyl-3- (2H) -isothiazolone, 4, 5-dichloro-2-octyl-4-isothiazolin-3-one (DCOIT), carbendazim, 2-tert-butylamino-4-cyclopropylamino-6-methylthio-s-triazine, di-n-butylthio-4-cyclohexylene, di-ethylthio-1, 2-trifluoromethylthio-1, 2-benzothiazol, 4, 5-dichloro-2-octyl-4-isothiazolin-3-one (DCOIT), carbendazim, 2-tert-butylamino-4-cyclopropylamino-6-methylthio-s-triazine, di-ethylthio-triazine, and mixtures thereof, 10,10 '-oxybis-phenoxarsine, triclosan, 2-methylthio-4-tert-butylamino-6-cyclopropylamino-s-triazine, N-cyclopropyl-N' - (1, 1-dimethylethyl) -6-methylthio) -1,3, 5-triazine-2, 4-diamine, zinc dimethyldithiocarbamate (Ziram),

1051 (commercially available from BASF SE), tributyltin oxide (TBTO), 5-chloromethyl-2H-isothiazol-3-one/2-methyl-2H-isothiazol-3-one (CIT/MIT), Benzisothiazolinone (BIT), Methylisothiazolinone (MIT), hexahydro-1, 3, 5-tris (2-hydroxyethyl) -S-triazine, sodium pyrithione, zinc 2-pyridylthio-1-oxide, 1, 2-benzisothiazolin-3-one, glutaraldehyde, 2-dibromo-3-nitrilopropionamide (DBNPA), polyhexamethylene biguanide hydrochloride (PHMB), 2-bromo-2-nitropropane-1, 3-diol (Branopol), 1, 2-dibromo-2-4-dicyanobutane, 1-bromo-1- (bromomethyl) -1, 3-malononitrile, 2-dibromo-3-nitropropionamide, benzyl bromoacetate, 1-bromo-1- (bromomethyl) -1, 3-malononitrile, dazomet, dodecylguanidine hydrochloride, methylene dithiocyanate, 1-methyl-3, 5, 7-triaza-1-nitrilo-adamantane chloride, 2-bromo-4' -hydroxyacetophenone, dibromo-3-nitrilopropionamide, 1, 2-benzisothiazolin-3-one, hexahydrotriazine, bromo-beta-nitrostyrene, ethyldihydro-1H, 3H, 5H-oxazolo (3,4-C) oxazole, acetoxy-2, 4-dimethyl-m-dioxane, nitrobutylmorpholine, ethyl-2-nitrotrimethylenedimorpholine, sodium orthophenylphenoxide, chloroallyl-3, 5, 7-azaadamantane chloride, diphenol sodium salt, tributyltin benzoate, alkylamine hydrochloride, monocyclic oxazolidine mixture, n-methyl-2-hydroxymethyloxypropyl-2' -hydroxypropylamine, sodium hydroxymethylglycinate, bicyclic oxazolidine mixture, 1, 3-bis (hydroxymethyl) -5, 5-dimethylhydantoin, hydroxymethyl 5, 5-dimethylhydantoin, 5-chloro-2-methyl-4-isothiazolin-3-one, 2-methyl-4-isothiazolin-3-one, 2-methyl-4-isothiazolin-3-one and combinations thereof.

Non-limiting examples of colorants can include pigments and/or dyes. Suitable pigment materials can be found in Hunger's "Industrial Organic Pigments," Itoh's "Dictionary of Pigments," and Leach and Pierce's "Printing Ink Manual. Examples of inorganic pigments may include, but are not limited to, pigment black (lamp black, furnace black, channel black), iron oxides (red, yellow, brown, black, transparent, etc.), spinel black, chromium oxide green, chromate yellow, iron blue, zinc chromate, molybdate orange, molybdate red, ultramarine, cadmium, mixed phase pigments (nickel titanium yellow, chromium titanium yellow, cobalt green, cobalt blue, zinc iron brown, iron manganese black), various types of metal powder pigments such as aluminum powder, gold powder, silver powder, copper powder, bronze powder, brass powder, and the like; or metallic flake pigments thereof; mica flake pigments; mica flake pigments which have been coated with metal oxides; mica-shaped oxide pigments, and the like.

Organic pigments may include, but are not limited to, monoazo pigments (acetoacetanilides, benzimidazolones, naphthol AS, colored b-naphthol dyes), disazo pigments (azo condensation pigments, dipyrazolones), polycyclic pigments (quinacridones, dioxazines, perylenes, diketopyrrolopyrroles, isoindolines) and metal complex pigments (copper phthalocyanines). Examples of the dye may include metal complex dyes, anionic dyes, azo dyes, and the like.

The cellulose derivative may include, but is not limited to, Ethyl Cellulose (EC), hydroxyethyl cellulose (HEC), hydroxypropyl cellulose (HPC), ethyl hydroxyethyl cellulose (EHEC), carboxymethyl cellulose (CMC), carboxymethyl hydroxyethyl cellulose (CMHEC), hydroxypropyl hydroxyethyl cellulose (HMHEC), Methyl Cellulose (MC), methylhydroxypropyl cellulose (MHPC), methylhydroxyethyl cellulose (MHEC), carboxymethyl methyl cellulose (CMMC), hydrophobically modified carboxymethyl cellulose (HMCMC), hydrophobically modified hydroxyethyl cellulose (HMHEC), hydrophobically modified hydroxypropyl cellulose (hmhphc), hydrophobically modified ethyl hydroxyethyl cellulose (HMEHEC), hydrophobically modified carboxymethyl hydroxyethyl cellulose (HMCMHEC), hydrophobically modified hydroxypropyl hydroxyethyl cellulose (HMHPHEC), Hydrophobically Modified Methyl Cellulose (HMMC), hydrophobically modified methyl hydroxypropyl cellulose (hmpc), Hydrophobically modified methyl hydroxyethyl cellulose (HMMHEC), hydrophobically modified carboxymethyl methyl cellulose (HMCMMC), cationic hydroxyethyl cellulose (cationic HEC), cationic hydrophobically modified hydroxyethyl cellulose (cationic HMHEC), nanofibrillated cellulose (NFC), and microfibrillated cellulose (MFC).

The guar and guar derivatives may include, but are not limited to, carboxymethyl guar, carboxymethyl hydroxypropyl guar, cationic hydroxypropyl guar, hydroxyalkyl guar such as hydroxyethyl guar, hydroxypropyl guar and hydroxybutyl guar, carboxyalkyl guar such as carboxypropyl guar, carboxybutyl guar, and the like.

Examples of the defoaming agent or defoaming agent may include, but are not limited to, silicone defoaming agents comprising polysiloxane and hydrophobic particles, non-silicone defoaming agents comprising hydrophobic particles and polymers, non-silicone defoaming agents comprising polymers, mineral oil defoaming agents composed of paraffin-based mineral oil, hydrophobic particles, and polysiloxanes.

Surfactants provide excellent surface tension lowering capability to wet substrates. The surfactants used in the present disclosure may be nonionic surfactants and anionic surfactants.

Examples of the nonionic surfactant may include, but are not limited to, C12-C18 fatty alcohol ethoxylate, C12-C14 fatty alcohol ethoxylate, C16-C18 fatty alcohol ethoxylate, C13-C15 oxoalcohol ethoxylate, C10-C18 alcohol ethoxylate, C13 oxoalcohol ethoxylate, C10 Guerbet (Guerbet) alcohol ethoxylate, C10 Guerbet alcohol alkoxylate, C10 oxoalcohol ethoxylate, alkylpolyglycoside (e.g., C8-C10 alkylpolyglycoside, C8-C14 alkylpolyglycoside, C12-C14 alkylpolyglycoside, blend of C12-C14 alkylpolyglycoside on inorganic and organic carriers), amine ethoxylate (e.g., oleyl amine +12EO, coco amine +12EO), amino polyol (e.g., triethanolamine +18EO, ethylene diamine +4PO), alkylpyrrolidone (e.g., N-octyl pyrrolidone), N-butylpyrrolidone, N-dodecylpyrrolidone), resin precursors and additives (e.g., bisphenol A ethoxylate, BIS A +3EO, BIS A +4EO, BIS A +6EO), emulsifiers and solubilizers (e.g., 4-C10-13-secondary alkylbenzene sulfonate calcium salt derivative, castor oil + -20 EO, castor oil + -35 EO, castor oil + -40 EO, epoxidized vegetable oil, ethoxylated rapeseed oil, ethoxylated sorbitan ester, decanol + -3 EO, C8 fatty alcohol +4EO, fatty alcohol ethoxylate, C8-C10 fatty alcohol + -5 EO, C12-C14 fatty alcohol + -50 EO, ethoxylated sorbitan trioleate, castor oil ethoxylate, phenol ethoxylate, alcohol ethoxylate, ethoxylated mono/diglyceride), foam inhibitors (e.g., polyalkoxy esters and solvents), Fatty alcohol alkoxylates, carboxylic acid esters, phosphoric acid esters, combinations of paraffin wax and silicon on a carrier, alkyl polyalkylene glycol ethers, Guerbet alcohol C16+ 2EO, fatty alcohol alkoxylates), low-foaming nonionic surfactants (such as fatty alcohol alkoxylates, modified fatty alcohol polyglycol ethers, amine alkoxylates, capped Guerbet alcohol alkoxylates, capped fatty alcohol alkoxylates, PO/EO block copolymers), laurylamine oxide, cocamidopropyl amine oxide, alkylamidopropyl betaines, polyglycol ethers of fatty diols, oleamide +10EO, emulsifiable methyl oleate, unsaturated fatty alcohol ethoxylates, fatty alcohol polyglycol ethers containing fatty acids, unsaturated fatty alcohol ethoxylates, polyethylene glycols, polypropylene glycols, methyl polyethylene glycols, alkyl polyalkylene glycol copolymers, Alkyl polypropylene glycols, polyfunctional polyalkylene glycols, reactive polyalkylene glycols.

Other nonionic surfactants can include, but are not limited to, alkylphenol ethoxylates such as nonylphenol ethoxylate and octylphenol ethoxylate, secondary alcohol alkoxylates such as secondary alcohol ethoxylate (TERGITOL)^TM15-S-9, commercially available from Dow Chemical Company) and primary alcohol alkoxylates.

Examples of anionic surfactants may include, but are not limited to, sodium lauryl ether sulfate +2EO, sodium isotridecyl alcohol ether sulfate +20EO, sodium fatty alcohol ether sulfate +2EO, sodium fatty alcohol ether sulfate +4EO, sodium fatty alcohol ether sulfate +7EO, sodium fatty alcohol ether sulfate +12EO, sodium fatty alcohol ether sulfate +30EO, sodium fatty alcohol ether sulfate +50EO, C12-C14 sodium fatty alcohol ether sulfate +1EO, C12-C14 sodium fatty alcohol ether sulfate +2EO, C12-C14 sodium fatty alcohol ether sulfate +3EO, C8-C14 ammonium fatty alcohol sulfate, sodium 2-ethylhexyl sulfate, C16-C18 fatty alcohol sulfate, sodium C12 fatty alcohol sulfate, sodium C12-C14 fatty alcohol sulfate, C12-C16 fatty alcohol sulfate, C12-C18 fatty alcohol sulfate, C16-C18 fatty alcohol sulfate, sodium C12 fatty alcohol sulfate, sodium C6332 fatty alcohol sulfate, sodium C12-C12 fatty alcohol sulfate, sodium C18 fatty alcohol sulfate, C8 fatty alcohol sodium sulfate salt, linear C10-C13 sodium alkyl benzene sulfonate, linear C10-C13 sodium alkyl benzene sulfonate and potassium oleate sulfonate.

Other surfactants used in the present disclosure may include, but are not limited to, ester quaternary ammonium salts, alkyl ether phosphate sodium salts, sodium N-lauryl- β -iminodipropionate, acid phosphate esters of fatty alcohol ethoxylates +3EO, monoalkenyl sulfosuccinic acid sodium salts +5EO, diisodecyl sulfosuccinic acid sodium salts, dioctyl sulfosuccinic acid sodium salts, acid phosphate esters, dodecylbenzene sulfonic acid amine salts, alkyl phosphates, and the like.

Non-limiting examples of the coalescent may include ethylene glycol monobutyl ether acetate, diethylene glycol monoethyl ether, lower monoalkyl ethers of ethylene glycol or propylene glycol (propylene glycol methyl ether), dimethyl succinate, diethyl succinate, diisopropyl succinate, toluates (e.g., 2-ethoxyethyl p-toluate, 2-propoxyethyl o-toluate, 2-ethoxyethyl benzoate, 2- (2-ethoxyethoxy) ethyl p-toluate), benzoates (e.g., 2- (2-ethoxyethoxy) ethyl benzoate, 2-propoxyethyl benzoate, 2-methoxy-1-methylethyl benzoate, 2- (2-methoxy-1-methylethoxy) -1-methylethyl benzoate, methyl ethyl benzoate, and mixtures thereof, 2-propoxy-1-methylethylbenzoate). Levulinic acid ester of 2-hexyl-1-decanol, levulinic acid ester of 1-tetradecanol/2-hexyldecanol, dioctyl succinate, polytrimethylene ether glycol, hexylene glycol, butoxyethoxypropanol, n-propoxypropanol, n-butoxypropanol, diethylene glycol monobutyl ether acetate, phenyl glycol ether, 2, 4-trimethylpentanediol-1, 3-monoisobutyrate, n-dibutyl glutarate, n-dipentyl glutarate, n-dihexyl glutarate, n-diheptyl glutarate, n-dioctyl glutarate, diisobutyl glutarate, di-2-methylbutyl glutarate, di-4-methyl-2-pentyl glutarate, di-2-ethylhexyl glutarate, amyl glutarate, dipropylene glycol monobutyl glutarate, and the like. Mixtures of these compounds are also suitable as coalescing agents.

Coating compositions comprising dihydroxylactam-based polymers according to the present disclosure can be applied to a variety of surfaces and substrates. These surfaces and substrates may include, but are not limited to, asphalt, cement, concrete, gypsum board, glass, masonry, metal, paper, plastic, textiles, wallpaper, and wood. Coating compositions according to the present disclosure can provide enhanced hiding power to substrates coated with the compositions.

The present disclosure also relates to a pharmaceutical composition comprising: (I) from a mixture comprising (i) N- (2, 3-dihydroxypropyl) -2-pyrrolidone and/or 1- [2- (2, 3-dihydroxypropoxy) ethyl ] -2-pyrrolidone; (ii) a polymer obtained from a reaction mixture of poly (D, L-lactide), wherein the amounts of (i) and (II) are independently about 0.01 mol% to about 99.99 mol%, and the polymer is a polyester, and (II) one or more pharmaceutically acceptable additives.

According to one embodiment, the pharmaceutically acceptable additive is selected from the group consisting of plasticizers, disintegrants, surfactants, lubricants, glidants, carriers, anti-adherents, fillers, wetting agents, pH modifiers, binders, solubility modifiers, recrystallization inhibitors, coating agents, diluents, colorants, preservatives, anti-foaming agents, antioxidants, buffers, acidulants, alkalizing agents, complexing enhancers, cryoprotectants, electrolytes, gelling agents, emulsifiers, solubilizers, stabilizers, tonicity modifiers, flavoring agents, sweeteners, complexing agents, fragrances, and viscosity modifiers.

The present disclosure also relates to a method of making a polymer comprising: (A) (ii) at least one functional moiety having a hydroxyl-reactive functional group; wherein the amounts of (i) and (ii) are independently about 0.01 mole% to about 99.99 mole%, and the polymer is selected from the group consisting of polyesters, polycarbonates, polyethers, polyester ethers, polyester amides, polyimides, polyamides, polyacrylates, and polyesterimides; or wherein each of (i) and (ii) is present in an amount other than 50 mol% and the polymer is a polyurethane; (B) charging (a) to a reaction vessel under an inert atmosphere and adding a solvent; (C) stirring the reaction mixture of (B) and maintaining the temperature at 55-70 ℃ for about 30 minutes; (D) adding an additional reactive moiety to (C); (E) polymerizing (D) with a catalyst for 3 to 5 hours; (F) recovering the desired polymer from (E).

Solvents may be used to synthesize the polymers according to the present disclosure. Any solvent that does not contain active hydrogen may be used. Non-limiting examples of the solvent may include acetone, dimethylacetamide, toluene, xylene, aliphatic hydrocarbons, dialkyl ethers of alkylene glycols, and diethoxymethane.

According to another embodiment, the solvent system is present in an amount from about 60% to about 99.9% by weight of the thickener system. In another embodiment, other possible ranges for the solvent system include, but are not limited to, about 60 wt.% to about 70 wt.%; about 70 wt.% to about 80 wt.%; about 80 wt.% to about 90 wt.%; about 90 wt.% to about 99.9 wt.%.

Catalysts may be used to synthesize the polymers according to the present disclosure. Non-limiting examples of the catalyst may include dibutyltin dilaurate, 1, 4-diazabicyclo [2,2,2] octane, triethylamine, pyridine, and p-toluenesulfonic acid.

The present disclosure relates to a method of thickening a composition comprising adding to the composition a dihydroxylactam-based polymer as described above. Examples of the composition may include, but are not limited to, coating compositions, construction compositions, personal care compositions, oilfield compositions, drilling fluids, drilling muds, well cementing fluids, servicing fluids, gravel packing muds, fracturing fluids, completion fluids, workover fluids, spacer fluids, household, industrial, and institutional compositions, pharmaceutical compositions, food compositions, biocides, adhesives, inks, papers, polishes, films, metal working fluids, plastics, textiles, printing compositions, lubricants, preservatives, agrochemicals, and wood care compositions.

The polymers and their applications according to the present disclosure may be prepared and used according to the examples set forth below. These examples are given herein for the purpose of illustrating the present disclosure and are not intended to be limiting, e.g., of the preparation of the polymers and their use.

Example (b):

in the examples, the following abbreviations are used:

EPDLOLs: 1- [2- (2, 3-dihydroxypropoxy) ethyl ] -2-pyrrolidone

PEG 1: polyethylene glycol, about Mn 7860, Mw 8240

PEG 2: polyethylene glycol, about Mn 3640, Mw 3790

DBTD: dibutyl tin dilaurate

HMDI: 4,4' -methylenebis (cyclohexyl isocyanate)

HDI: hexamethylene diisocyanate

IPDI: isophorone diisocyanate

DMBA: dimethylolbutanoic acid

DMAc: dimethylacetamide

MBPI: 4,4' -methylenebis (phenylisocyanate)

DMPA: dimethylolpropionic acid

MDEA: methyldiethanolamine

TEA: triethylamine

DMI: itaconic acid dimethyl ester

MA: maleic anhydride

acr.Cl: acryloyl chloride

GMA: glycidyl methacrylate

Example 1: reaction of EPDIOL with glycidol

Glycidol (5.45g) and EPDIOL (15g) were mixed into a mixture of acetone and TEA (40g) in a round bottom flask equipped with a stir bar and heating mantle and the mixture was stirred at 55 ℃ for 6 hours. The resulting mixture was clear and the resulting product passed the disappearance of the epoxy absorption band and the ether absorption band in the 800 region by IR (1,100-1,200 cm) ^-1) The formation of (d) was verified.

Example 2: reaction of EPDIOL with succinyl chloride

In a round bottom flask equipped with a stir bar and heating mantle, a mixture of succinyl chloride (11.44g) and EPDIOL (15g) was mixed into acetone (50g) and the mixture was stirred at 55 ℃ for 2 hours. The resulting mixture was dark brown and the product obtained was purified by IR at 1735cm^-1The formation of the absorption band of the ester of (a) was verified.

Example 3: reaction of EPDIOL with DMI

In a round bottom flask equipped with a stir bar and heating mantle, a mixture of DMI (11.65g) and EPDIOL (15g) was mixed into a mixture of acetone and TEA (50g), and the mixture was stirred at 55 ℃ for 4 hours. The resulting mixture was clear and the resulting product was passed through IR at 2840cm^-1In the methoxy group CH₃Band reduction at 1730cm^-1The formation of the absorption band of the ester was verified.

Example 4: reaction of EPDIOL with MA

In a round bottom flask equipped with a stir bar and heating mantle, a mixture of MA (15g) and EPDIOL (31.10g) was mixed into acetone (65g) and the mixture was stirred at 55 ℃ for 6 hours. The resulting mixture was pale yellow and the product was obtained by passing the anhydride at 1850cm^-1、1774cm^-1Disappearance of the peak of (1) and 1717cm^-1The appearance of an ester peak was confirmed.

Example 5: reaction of EPDIOL with acr.cl

A mixture of acr.cl (6.68g) and EPDIOL (43g) was mixed into acetone (43g) in a round bottom flask equipped with a stir bar and heating mantle. To the mixture was further added triethylamine as a catalyst, and the mixture was stirred at 55 ℃ for 2 hours. The resulting mixture was orange and the resulting product was passed through IR at 1730cm^-1The ester peak of (a) was verified.

Example 6: reaction of EPDIOL and GMA

In a round bottom flask equipped with a stir bar and heating mantle, a mixture of GMA (10.49g) and EPDLOL (15g) was mixed into acetone (50 g). To the mixture was further added triethylamine as a catalyst, and the mixture was stirred at 55 ℃ for 2 hours. The resulting mixture was transparent, and the resulting product disappeared by IR at the 844 absorption band of the epoxide and at 1,100cm^-1The formation of the ether absorption band was verified.

Example 7: EPDIOL and phosphorus oxychloride

A mixture of phosphorus oxychloride (11.30g) and EPDIOL (15g) was mixed into acetone (50g) in a round bottom flask equipped with a stir bar and heating mantle. To the mixture was added triethylamine as a catalyst, and the mixture was stirred for 4 hours. The resulting mixture was dark brown.

EPDIOL-based polyurethanes

Example 8: reaction of EPDIOL with MBPI

EPDIOL (0.5mol) and DMAc were added to the process reactor. The reaction mixture was stirred and heated to 65-70 ℃. Further, MBPI (1.1mol) was added to the reaction mixture and the resulting reaction mixture was stirred for 5-15 minutes. DBTD (2.0% by weight of isocyanate) was added to the reaction mixture and stirred for 5 hours. The contents were discharged and allowed to cool to ambient temperature to give the polymer.

Example 9: reaction of EPDIOL with PEG2, DMBA, HDI and hexanol

EPDIOL (0.73mol), PEG2(0.32mol) and DMBA (0.95mol) and acetone were added to the process reactor. The resulting reaction mixture was stirred and heated to 70-75 ℃. Furthermore, HDI (2.1mol) was added to the reaction mixture and the reaction mixture was stirred for 5 to 15 minutes. DBTD (2.0% by weight of isocyanate) was added to the reaction mixture and stirred for 4 hours. Hexanol (0.2mol) was added and stirred for 1.0 h. Triethylamine was added to neutralize the DMBA, the contents were drained and cooled to ambient temperature to give a polymer.

Example 10: reaction of EPDIOL with MDEA, PEG2, HDI and hexanol

EPDIOL (0.73mol), PEG2(0.32mol) and methyldiethanolamine (0.95mol) and acetone were added to the reactor. The reaction mixture was stirred and heated to 70-75 ℃. Furthermore, HDI (2.1mol) was added to the reaction mixture and the reaction mixture was stirred for 5 minutes. DBTD (2.0% by weight of isocyanate) was added to the reaction mixture and stirred for 5 hours. Hexanol (0.2mol) was added and stirred for 1.0 h. Acetic acid was added, the contents were discharged and allowed to cool to ambient temperature to give a polymer.

Example 11: the reaction of example 9 was repeated by replacing DMBA with DMPA and HDI with IPDI.

Hydrophobically modified urethane-ethoxylate (HEUR) polymers

Hydrophobically modified urethane-ethoxylate (HEUR) polymers are prepared by introducing EPDIOL monomers into the backbone of urethane ethoxylate polymer "structure-1".

Structure-1

Example 12 (a): EPDIOL-IPDI-HEUR

Hydrophobically modified urethane-ethoxylate (HEUR) polymers are prepared from a reaction mixture comprising EPDIOL monomer and IPDI, shown in structure-2 and described in the examples below.

Structure-2

Table 1: EPDIOL-PEG 1-IPDI-hexanol-HEUR

Table 2: EPDIOL-PEG 2-IPDI-hexanol-HEUR

Table 3: EPDIOL-PEG 1-IPDI-hexanol-HEUR

nedliol refers to the number of targets of EPDIOL on each chain.

Example 13: solvent process

EPDIOL (12.71g) was dissolved in 15g of anhydrous acetone and fed into the process reactor together with 182.53g of PEG2 and 175.0g of anhydrous acetone. The reaction mixture was mixed and heated to 65-70 ℃. A solution of IPDI (27.46g) in 15g of anhydrous acetone was added at this temperature and mixed for 5 to 15 minutes. A solution of 0.590g DBTDL (dibutyltin dilaurate) in 10g acetone was then added. Mix for 5 hours. 2.53g of hexanol was added thereto, and the reaction was continued for 1.0 hour. Finally, the product is drained, dried in a vacuum oven or the solvent is exchanged for water.

Example 14: EPDIOL-HMDI HEUR polymers

TABLE 4 EPDLOL-PEG 1-HMDI-hexanol-HEUR

Example 14 (c): melting process

Polyethylene glycol (PEG1) (1,376.50g), EPDIOL (18.88g) were charged to the process reactor. The reaction mixture was heated to 100 ℃ and 110 ℃ and stirred under vacuum for 0.5-1.0 h. The reaction mixture was cooled to 75-80 ℃ and further HMDI (89.30g) was added and mixed for 5-15 minutes. Thereafter, dibutyltin dilaurate (1.92g) was added and mixed at 100 ℃ and 110 ℃ for 2.0-2.5 hours. Once mixing was complete, hexanol (16.83g) was added and the reaction was continued for 1.0 hour. After the reaction was complete, the contents were discharged and cooled to ambient temperature to give a polymer.

Example 14 (d): solvent process

EPDIOL (1.89g) was dissolved in anhydrous acetone (15g) and added to the process reactor along with polyethylene glycol 1(PEG1) (137.65g) and acetone (245 g). The mixture was stirred and heated to 65-70 ℃. At this temperature, a mixture of (8.93g) HMDI in (15g) acetone was added and mixed for 5-15 minutes. A solution of dibutyltin dilaurate in (10g) acetone was then added and mixed for 5 hours, followed by addition of a solution of hexanol (1.68g) in (15g) acetone and reaction continued for 1.0 hour. The product was drained and dried in a vacuum oven or the solvent was exchanged for water.

Example 15: EPDLOL-HDI-HEUR polymers

The EPDIOL-HDI-HEUR polymer of Structure-3 was prepared using the composition of EODIOL described below.

Structure-3

Table 5: EPDIOL-PEG 1-HDI-hexanol-HEUR

TABLE 6 EPDIOL-PEG 2-HDI-hexanol-HEUR

Table 7: EPDIOL-PEG 1-HDI-decyl alcohol-HEUR

Table 8: EPDIOL-PEG 1-HDI-decyl alcohol-HEUR

Example 15 (d): solvent process

EPDIOL (12.69g) dissolved in 15g of anhydrous acetone was fed into the process reactor together with 188.96g of PEG2 and 175.0g of anhydrous acetone. The reaction mixture was mixed and heated to 65-70 ℃. Furthermore, a mixture of 21.05g HDI in 15g anhydrous acetone was mixed at this temperature for 5 to 15 minutes. A solution of 0.453g DBTDL in 10g acetone was then added to the reaction mixture. The reaction mixture was mixed for 5 hours. In addition, 2.53g of hexanol was added to the reaction mixture and the reaction was continued for 1.0 hour. At the end of the reaction, the product is discharged and dried in a vacuum oven or the solvent is exchanged for water.

Example 15 (I): melting process

EPDIOL (18.88g) and polyethylene glycol (PEG) were fed to the process reactor. The reaction mixture was heated to 100 ℃ and 110 ℃ and stirred under vacuum for 0.5-1.0 h. Cooled to 75-80 ℃ and HMDI (89.30g) was added and mixed for 5-15 minutes. Then, dibutyltin dilaurate (1.92g) was added and mixed at 100 ℃ and 110 ℃ for 2.5 hours. Once mixing was complete, hexanol (16.83g) was added and the reaction was continued for 1.0 hour. After the reaction was complete, the contents were discharged and allowed to cool to ambient temperature to obtain the product.

EPDLOL-HEUR example application in coatings:

example 16: preparation of the primer

Semi-gloss primer formulations without low shear and high shear thickeners were prepared by mixing the grind formulation given in table 9A and the let down formulation given in table 9B. During the let down phase, the low shear polymer, high shear polymer examples and water were retained.

Table 9A: grinding formula

Drewplus TM T-4304: antifoam agents, commercially available from Ashland Inc

7: micronized functional filler having a median particle size of 3.5 microns, commercially available from The Cary Company.

Table 9B: paint mixing formula

Rhoplex VS 1050: acrylic emulsion, Dow Chemical company

OptifilmTM Enhancer 400: coalescents, commercially available from Eastman Chemical Company.

Polypase 678: fungicides, commercially available from Troy Corporation.

Example 17: EPDLOL HEUR polymeric compositions

Table 10: EPDLOL HEUR polymeric compositions

Example 18 (a): comparative reference example 1 semi-gloss formulation

In comparative reference example 17(a), Aquaflow XLS 530 as Low Shear (LS) polymer, Acrysol RM2020(C6 HMDI) as High Shear (HS) polymer, and water were added together to the primer formulations shown in tables 9A and 9B. The dosages of LS, HS polymer and water were adjusted to achieve the target Krebs Stormer viscosity of 105 + -5 KU units and ICI viscosity of 130 + -10 m.Pa.s.

Example 19: semi-gloss formulations

In comparative example 17(B), Aquaflow XLS530 as Low Shear (LS) polymer, polymer solution example 17(B) as High Shear (HS) polymer, and water were added together to the primer formulation as shown in tables 9A and 9B. The dosages of LS, HS polymer and water were adjusted to achieve the target Krebs Stormer viscosity of 105 + -5 KU units and ICI viscosity of 130 + -10 m.Pa.s.

Example 20: semi-gloss formulations

In comparative example 17(c), Aquaflow XLS530 was added as a Low Shear (LS) polymer, polymer solution example 17(c) was added as a High Shear (HS) polymer, and water were added together to the primer formulations shown in tables 9A and 9B. The dosages of LS, HS polymer and water were adjusted to achieve the target Krebs Stormer viscosity of 105 + -5 KU units and ICI viscosity of 130 + -10 m.Pa.s.

Example 21: semi-gloss formulations

In comparative example 17(d), Aquaflow XLS530 was added as a Low Shear (LS) polymer, polymer solution example 17(d) was added as a High Shear (HS) polymer, and water were added together to the primer formulations shown in tables 9A and 9B. The dosages of LS, HS polymer and water were adjusted to achieve the target Krebs Stormer viscosity of 105 + -5 KU units and ICI viscosity of 130 + -10 m.Pa.s.

Example 22: semi-gloss formulations

In comparative example 17(e), Aquaflow XLS530 was added to the primer formulations shown in tables 9A and 9B as a Low Shear (LS) polymer, polymer solution example 17(e), and water together. The dosages of LS, HS and water were adjusted to achieve a target Krebs stormer viscosity of 105 + -5 KU units and an ICI viscosity of 130 + -10 m.Pa.s.

Example 23: wet paint properties

TABLE 11 Wet lacquer Properties

Example 24: dry film properties

TABLE 12 Dry film Properties

Test method

Stormer viscosity is measured by a Stormer viscometer according to standard test method ASTM D562 and expressed in Kreb Units (KU).

ICI viscosity is measured by an ICI cone and plate viscometer according to standard test method ASTM D4287, expressed in poise (P).

Brookfield viscosity is measured on a Brookfield viscometer using spindle 5 at 30 RPM.

Sag resistance was measured using a Leneta chart based on the standard ASTM D4400. Wet Film Thickness (WFT) in mils is measured, above which sag occurs.

Leveling is measured in the range of 0-10 based on the standard ASTM D4062 method using the Leneta diagram; 0 is worst and 10 is best.

Gloss was measured using a spectrophotometer at 60 ° and 80 ° angles.

Tables 11 and 12 show the wet paint and dry film properties of the polymer examples of the present disclosure. The results show that the polymers from the present disclosure exhibit good sag/leveling balance and gloss characteristics.

Table 12: dry film properties of the examples given in this disclosure are shown. The polymers provided in the present disclosure exhibit higher gloss and good sag/leveling balance.

While the invention has been described in detail with reference to certain preferred embodiments, it is to be understood that the invention is not limited to those precise embodiments. Rather, in view of this disclosure, many modifications and variations may be made by one of ordinary skill in the art without departing from the scope or spirit of the present invention.

Claims (19)

1. A polymer obtained from a reaction mixture comprising:

(i) at least one dihydroxylactam moiety; and

(ii) at least one functional moiety having a hydroxyl-reactive functional group;

wherein the amounts of (i) and (ii) are independently about 0.01 mole% to about 99.99 mole%, and the polymer is selected from the group consisting of polyesters, polycarbonates, polyethers, polyester ethers, polyester amides, polyimides, polyamides, polyacrylates, and polyesterimides; or wherein (i) and (ii) are each present in an amount other than 50 mol%, and wherein the polymer is a polyurethane.

2. The polymer of claim 1, wherein the dihydroxylactam moiety has the structure:

Wherein "R" is independently selected from the group consisting of hydrogen, and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, any of which may or may not have heteroatoms and which are straight or branched chain;

"A" is an alkylene or alkenylene group containing 2 to 50 carbon atoms; and

wherein, in

Group and

between the groups 2-4 carbon atoms are present in the lactam ring;

"n" is an integer from 1 to 6; and "m" is an integer from 0 to 6.

3. The polymer of claim 2, wherein the dihydroxylactam moiety is selected from the group comprising:

wherein "n" is an integer from 1 to 6; and "m" is an integer from 0 to 6.

4. The polymer of claim 3, wherein the dihydroxylactam moiety is selected from the group consisting of N- (2, 3-dihydroxypropyl) -2-pyrrolidone, 1- [2- (2, 3-dihydroxypropoxy) ethyl ] -2-pyrrolidone, and combinations thereof.

5. The polymer of claim 1, wherein the functional moiety is selected from the group consisting of: (a) carbamates, (b) acyl halides, (c) sulfonyl halides, (d) isothiocyanates, (e) cyanoacrylates, (f) isocyanates, (g) oxiranes, (h) imines, (i) thiocarbonates, (j) thiols, (k) aldehydes, (l) aziridines, (m) acids and their anhydrides, (n) azides, (o) phosphorus halides and alcohols, (p) esters, (q) amines, (r) alkyl halides,(s) dihalomethanes, and combinations thereof.

6. The polymer of claim 1, wherein the functional moiety is selected from the group consisting of:

(a) hydroxyethyl carbamate, hydroxypropyl carbamate, hydroxybutyl carbamate, and combinations thereof;

(b) acryloyl chloride, succinyl chloride, methacryloyl chloride, crotonyl chloride, benzoyl chloride, cinnamoyl chloride, hydrocinnamoyl chloride, acetyl chloride, 2-acetoxyacetyl chloride, diphenylacetyl chloride, 2-methoxybenzoyl chloride, 3,4,5 trimethoxybenzoyl chloride, 3,4 (methylenedioxy) benzoyl chloride, cyclopropane carbonyl chloride, pentadecenyl acyl chloride, 2-cyclohexene-1-carbonyl chloride, 2-thiopheneacetyl chloride, and combinations thereof;

(c) methanesulfonyl chloride, benzenesulfonyl chloride, and combinations thereof;

(d) methyl isothiocyanate, allyl isothiocyanate, aryl isothiocyanate and combinations thereof;

(e) ethyl cyanoacrylate, N-butyl-cyanoacrylate (NBCA), 2-octyl cyanoacrylate (2-OCA), and combinations thereof;

(f) hexamethylene diisocyanate, Toluene Diisocyanate (TDI), diphenylmethane diisocyanate (MDI), m-phenylene diisocyanate, p-phenylene diisocyanate, xylene diisocyanate, cyclohexane diisocyanate (CHDI), bis (isocyanatomethyl) cyclohexane (H6XDI), dicyclohexylmethane diisocyanate (H12MDI), dimer acid diisocyanate (DDI), trimethylhexamethylene diisocyanate, lysine diisocyanate and its methyl ester, isophorone diisocyanate, methylcyclohexane diisocyanate, 1, 5-naphthalene diisocyanate, xylene and xylene diisocyanate and their methyl derivatives, polymethylene polyphenyl isocyanates, chlorobenzene-2, 4-diisocyanate, polyphenyl diisocyanates, isophorone diisocyanate (IPDI), Hydrogenated Methylene Diphenyl Isocyanate (HMDI), Tetramethylxylene diisocyanate (TMXDI), Hexamethylene Diisocyanate (HDI), and their respective dimers, trimers, and oligomers;

(g) Ethylene Oxide (EO), Propylene Oxide (PO), butylene oxide, 1-octene oxide, cyclohexene oxide, styrene oxide, bisphenol A diglycidyl ether, epichlorohydrin, glycidol, allyl glycidyl ether ([ (2-propenyloxy) methyl ] -oxirane), (meth) acrylic acid glycidyl ester, vinylcyclohexene diepoxide, 3, 4-epoxycyclohexylmethyl-3, 4-epoxycyclohexane carboxylate, 3, 4-epoxy-6-methylcyclohexylmethyl-3, 4-epoxy-6-methylcyclohexane carboxylate, dipentene dioxide, 2- (3, 4-epoxycyclohexyl-5, 5-spiro-3, 4-epoxy) cyclohexane-m-dioxane, and combinations thereof;

(h) polyaldimines, hydroxyaldimines, polyketimines, hydroxyketimines, and combinations thereof;

(i) bis- (phenylthiocarbonyloxymethyl) esters, bis- (isopropylthiocarbonyloxymethyl) esters, and combinations thereof;

(j) glutathione, 3-acetylthiolpropanoic acid, thioanhydride, thioacid, and combinations thereof;

(k) acetaldehyde diethyl acetal, propionaldehyde diethyl acetal, di (acetaldehyde diethyl acetal), chloroacetaldehyde diethyl acetal, and combinations thereof;

(l)2, 2-bis-hydroxymethylbutanol tris- [3- (1-aziridinyl) propionate ], bis-N-aziridinemethane, and combinations thereof;

(m) maleic acid, maleic anhydride, fumaric acid, citric acid, alkenyl succinic anhydride, phthalic anhydride, terephthalic acid, succinic anhydride, tetrahydrophthalic anhydride, maleic anhydride copolymers, and combinations thereof;

(n) azide-functionalized DNA, azide-functionalized peptides, azide-functionalized proteins, azide-functionalized sugars, azide-functionalized metals, azide-functionalized nanoparticles, azide-functionalized antimicrobial agents, disodium 4,4 '-diazide stilbene-2, 2' -disulfonate, aromatic bis-azide, calcium azide, 4-diphenyl disulfonyl azide, and p-toluenesulfonyl azide, and combinations thereof;

(o) phosphorus oxychloride, phosphorus oxybromide, and combinations thereof;

(p) dimethyl itaconate, di-n-butyl itaconate, vinyl hexanoate, glycolide, epsilon-caprolactone, gamma-caprolactone, poly (D, L-lactide), poly (D-lactide), poly (L-lactide), poly (epsilon-caprolactone), poly (gamma-caprolactone), polyglycolide, valerolactone, butyrolactone, polyether-polyester, polyanhydride-diol-polyester, and combinations thereof;

(q) aminoalcohols, methylamines, ethylamines, hexylamines, isopropylamine, isobutylamine, pentylamine, cyclohexylamine, octylamine, benzylamine, dimethylamine, diethylamine, dipropylamine, dibutylamine, diphenylamine, dibenzylamine, ethylmethylamine, N-methylaniline, ethylenediamine, propylenediamine, butylenediamine, hexamethylenediamine, cyclohexanediamine, piperazine, toluenediamine, isophoronediamine, N-dimethylaniline, N-dimethyl-1-naphthylamine, N-dimethyl-p-toluidine, N-diethylaniline, N-diallylaniline, 1-phenylpiperidine, and 4-phenylmorpholine, aminoethoxylates, coconut oil saddles, soy amines and combinations thereof,

(r) bromohexane, bromododecane, bromohexadecane, 1-bromooctadecane and combinations thereof, and

(s) dibromomethane, methylene chloride, and combinations thereof.

7. The polymer of claim 1, wherein the reaction mixture further comprises one or more non-lactam moieties.

8. The polymer of claim 7, wherein the non-lactam moiety is selected from the group comprising: carbon chain length of C₁-C₁₈With a carbon chain length of C₁-C₁₈Alkoxylated alcohols, ethylene glycol, methyl (acrylate) alcohols, polyvinyl alcohol, polycarbonate polyols, polytetramethylene glycol, polyethylene glycol, polypropylene glycol, hydroxyl polyesters, hydroxyl polyethers, hydroxyl polythioesters, hydroxyl polyacetals, hydroxyl polycarbonates, polyether polyols, polyester polyols, polycarbonate polyols, hydroxyl polyesters, hydroxyl polyethers, hydroxyl polythioesters, hydroxyl polyacetals, hydroxyl polycarbonates, aliphatic and aromatic polyether polyols, caprolactone polyols, poly (ethylene glycol) -soyamines, poly (ethylene glycol) -castor oil, poly (ethylene glycol) -hydrogenated castor oil, poly (ethylene glycol) -lanolin wax, poly (ethylene glycol) -polyvinylidene fluoride, poly (ethylene glycol) -poly (vinyl acetate), poly (ethylene glycol) -polyoxymethylene, Poly (ethylene glycol) -esters and combinations thereof.

9. The composition of claim 1, wherein the polymer has an average molecular weight of about 3000g/mol to about 1,000,000 g/mol.

10. A polymer obtained from a reaction mixture comprising:

(i) n- (2, 3-dihydroxypropyl) -2-pyrrolidone and/or 1- [2- (2, 3-dihydroxypropoxy) ethyl ] -2-pyrrolidone, and

(ii) poly (D, L-lactide);

wherein the amounts of (i) and (ii) are independently about 0.01 mol% to about 99.99 mol%, and the polymer is a polyester.

11. A polymer obtained from a reaction mixture comprising:

(i) n- (2, 3-dihydroxypropyl) -2-pyrrolidone and/or 1- [2- (2, 3-dihydroxypropoxy) ethyl ] -2-pyrrolidone, and

(ii) a) isophorone diisocyanate, b) polyethylene glycol, and optionally c) octanol; wherein (i) and (ii) are each present in an amount other than 50 mol% and the polymer is a polyurethane.

12. A composition comprising:

(I) a polymer obtained from a reaction mixture comprising:

(i) at least one dihydroxylactam moiety; and

(ii) at least one functional moiety having a hydroxyl-reactive functional group;

wherein the amounts of (i) and (ii) are independently about 0.01 mole% to about 99.9 mole%, and the polymer is selected from the group consisting of polyesters, polyamides, polyesteramides, polyesterimides, polycarbonates, and polyethers; or

Wherein (i) and (ii) are each present in an amount other than 50 mol% and the polymer is a polyurethane; and

(II) one or more additives.

13. The composition of claim 13, wherein the additive is used in an application selected from the group consisting of: adhesives, aerosols, agricultural agents, anti-soil redeposition agents, batteries, beverages, biocides, biomaterials, adhesives and construction agents, cleaning agents, paints & coatings, rheology modifiers, conductive materials, cosmetic agents, dental agents, decorative pigments, detergents, dispersants, pharmaceuticals, electronics, packaging, food, hair care agents, home industry institutional agents, inks and coatings, interlayers, lithographic printing solutions, film additives, metal working fluids, oilfield agents, paper sizing agents, polishes, personal care agents, pharmaceuticals, pigment additives, gypsum, plastics, textiles, lubricants, printing, refractive index modifiers, chelants, soil release agents, static control agents, and wood care agents.

14. A pharmaceutical composition comprising:

I. a polymer obtained from a reaction mixture comprising: (i) n- (2, 3-dihydroxypropyl) -2-pyrrolidone and/or 1- [2- (2, 3-dihydroxypropoxy) ethyl ] -2-pyrrolidone; and (ii) poly (D, L-lactide); wherein the amounts of (i) and (ii) are independently about 0.01 mol% to about 99.99 mol%, and the polymer is a polyester, and

One or more pharmaceutically acceptable additives.

15. The pharmaceutical composition of claim 15, wherein the pharmaceutically acceptable additive is selected from the group comprising: plasticizers, disintegrants, surfactants, lubricants, glidants, carriers, anti-adherents, fillers, wetting agents, pH modifiers, binders, solubility modifiers, recrystallization inhibitors, coating agents, diluents, colorants, preservatives, anti-foaming agents, antioxidants, buffers, acidulants, alkalizing agents, complexing enhancers, cryoprotectants, electrolytes, gelling agents, emulsifiers, dissolution enhancers, stabilizers, tonicity adjusting agents, flavors, sweeteners, complexing agents, fragrances, and viscosity adjusting agents.

16. A coating composition comprising:

I. a polymer obtained from a reaction mixture comprising: (i) n- (2, 3-dihydroxypropyl) -2-pyrrolidone and/or 1- [2- (2, 3-dihydroxypropoxy) ethyl ] -2-pyrrolidone, and (ii) a) isophorone diisocyanate, b) polyethylene glycol, and optionally c) octanol; wherein neither (i) nor (ii) is present in an amount of 50 mol%, and the polymer is a polyurethane, and

one or more coating agents.

17. The coating composition of claim 17, wherein the coating agent is selected from the group comprising: solvents/co-solvents, secondary rheology modifiers, thixotropic agents, binders, cross-linking agents, pH adjusting agents, pigments/fillers, flow control agents, gloss control agents, coalescents, toughening resins, surfactants, waxes, wetting agents, dispersants, plasticizers, antioxidants, ultraviolet radiation absorbers, bactericides, extenders, colorants, adhesion promoters, defoaming/antifoaming agents, drying agents, matting agents, and combinations thereof.

18. A method of making a polymer comprising:

(A) (ii) at least one functional moiety having a hydroxyl-reactive functional group; wherein the amounts of (i) and (ii) are independently about 0.01 mole% to about 99.99 mole%, and the polymer is selected from the group consisting of polyesters, polycarbonates, polyethers, polyester ethers, polyester amides, polyimides, polyamides, polyacrylates, and polyesterimides; or wherein neither (i) nor (ii) is present in an amount of 50 mol% and the polymer is a polyurethane;

(B) adding (a) and a solvent to a reaction vessel under an inert gas atmosphere;

(C) Stirring the reaction mixture of (B) and maintaining the temperature at 55-70 ℃ for about 30 minutes;

(D) adding an additional reactive moiety to (C);

(E) polymerizing (D) with a catalyst for 3 to 5 hours; and

(F) recovering the desired polymer from (E).

19. A method of making a polymer comprising:

(A) (ii) at least one functional moiety having a hydroxyl-reactive functional group; wherein the amounts of (i) and (ii) are independently about 0.01 mole% to about 99.99 mole%, and the polymer is selected from the group consisting of polyesters, polycarbonates, polyethers, polyester ethers, polyester amides, polyimides, polyamides, polyacrylates, and polyesterimides; or wherein neither (i) nor (ii) is present in an amount of 50 mol% and the polymer is a polyurethane;

(B) adding (a) to a reaction vessel under an inert gas atmosphere;

(C) stirring the reaction mixture of (B) and maintaining the temperature at 65-80 ℃ for about 30 minutes;

(D) adding an additional reactive moiety to (C);

(E) polymerizing (D) with a catalyst;

(F) raising the temperature of (E) to 90-110 ℃ and maintaining the temperature for about 2-3 hours; and

(G) recovering the desired polymer from (F).