Dihydroxylactam polymers, compositions and their uses

Abstract

Lactam-functionalized polymers are disclosed. Dihydroxylactam-based polymers include polyesters, polycarbonates, polyethers, poly(ester ethers), poly(ester amides), polyimides, polyamides, polyacrylates, poly(ester imides), and polyurethanes. Applications for the dihydroxylactam-based polymers are also disclosed.

Description

[Technical field]

[0001] This application relates to dihydroxylactam-based polymers, compositions and their uses. [Background technology]

[0002] N-vinyl lactam polymers are polymers having lactam groups, such as pyrrolidone or caprolactam, in which the lactam nitrogen is directly attached to the polymer backbone. These polymers, such as poly(N-vinyl-2-pyrrolidone), poly(N-vinyl-ε-caprolactam), and poly(N-vinyl-2-pyrrolidone-co- N-vinyl acetate), are available in a wide range of molecular weights and find use in many application techniques, such as film formers, protective colloids, suspending agents, and other applications. A description of these applications and properties can be found in the technical brochure "PVP Polyvinylpyrrolidone Polymers," published by International Specialty Products, which is incorporated herein by reference in its entirety.

[0003] The success of N-vinyl lactam polymers is believed to be due in part to the chemical structure of the lactam group. Due to its lone pair of electrons, the lactam nitrogen can form hydrogen bonds to compounds containing -OH and -NH groups. Such interactions can be found in a variety of properties including adhesives (e.g., adhesive sticks, hair styling products, tablet binders), crystallization inhibitors (e.g., gas hydrates, sucrose solutions), and complexing agents (e.g., dyes, active ingredients).

[0004] In addition to molecular weight, the number of carbon atoms in the lactam ring can vary. Commonly known lactams range from 3 carbon atoms / 1 nitrogen atom in the ring (propiolactam) to 6 carbon atoms / 1 nitrogen atom in the ring (heptanolactam). Increasing the number of carbon atoms in the ring changes the hydrophilic / hydrophobic balance of the molecule. Both poly(N-vinyl-2-pyrrolidone) and poly(N-vinyl-ε-caprolactam) are water-soluble, but the former is more hydrophilic and will absorb more water in humid environments than the latter. Summary of the Invention [Problem to be solved by the invention]

[0005] However, the available range in lactam ring size and polymer molecular weight is insufficient to design new monomers and polymers with truly novel functionalities. For example, the nitrogen atom of N-vinyl lactams is directly attached to the polymer backbone without a spacer group, limiting the options to modulate the hydrophilic / hydrophobic balance of the molecule or to vary the relatively high glass transition temperature [e.g., 180° for poly(N-vinyl-2-pyrrolidone)]. New approaches to modify N-vinyl lactam structures are needed to facilitate novel properties and end-user applications.

[0006] To obtain different properties, current technology relies on copolymerizing other monomer units with N-vinyl lactam units. Many such non-homopolymers are known and include those formed with N-vinyl acetate, styrene, dimethylaminoethyl methacrylate, dimethylaminopropyl methacrylamide, acrylic acid, and lauryl methacrylate. Many properties can be altered by these copolymerizations, including hydrophilicity / hydrophobicity, film forming, flexibility, foaming ability, humidity response, viscosity, gloss, and tackiness. Copolymerizations produce useful products, but these products are primarily sought after when homopolymers fail to provide the desired properties. Novel lactam monomers and polymers thereof that provide extended functionality are desired.

[0007] In addition to limited functionality, N-vinyl lactam polymers require production methods and analytical testing to ensure sufficiently low residual monomers. Next generation lactam compounds that offer new properties and are also free of N-vinyl lactam monomers are needed.

[0008] A related family of compounds, the N-alkyllactams, useful for extending the lactam moiety, has an alkyl group covalently bonded to the lactam nitrogen. A variety of N-alkyllactams are known and include, but are 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, NJ). In addition, N-hydroxymethyl-2-caprolactam (1948, Benson) is also known. These non-polymeric chemicals find use as solvents, surface tension reducers, and low foaming surface wetting agents.

[0009] The prior art teaches several N-vinyl lactams modified via N-alkyl lactams, including the following patents: US Pat. Nos. 5,993, 6,149, 6,111, 6,149, 6,151, 6,163, 6,171, 6,182, 6,193, 6,196, 6,197, 6,198, 6,199, 7,199, 7,199, 8,199, 9,103, 9,104, 9,105, 9,116, 9,117, 9,118, 9,119, 9,121, 9,133, 9,142, 9,152, 9,166, 9,177, 9,187, 9,198, 9,1

[0010] Lipids of the 1-(2,3-dihydroxypropyl)pyrrolidin-2-one type are described in US Pat. No. 5,993,336.

[0011] Additionally, linear oligo- and polyurethanes with pyrrolidinone side chains have been described by Kim et al. in Polymers and Polymeric Materials, Vol. [Prior art documents] [Patent documents]

[0012] [Patent Document 1] U.S. Patent No. 2,882,262 [Patent Document 2] U.S. Pat. No. 4,008,247 [Patent Document 3] U.S. Pat. No. 4,189,601 [Patent Document 4] U.S. Pat. No. 4,190,582 [Patent Document 5] U.S. Pat. No. 4,191,833 [Patent Document 6] U.S. Pat. No. 4,191,834 [Patent Document 7] U.S. Pat. No. 4,439,616 [Patent Document 8] U.S. Pat. No. 4,609,706 [Patent Document 9] U.S. Pat. No. 5,209,347 [Patent Document 10] U.S. Pat. No. 5,252,689 [Patent Document 11] U.S. Pat. No. 5,466,770 [Patent Document 12] U.S. Patent No. 6,369,163 [Patent Document 13] U.S. Patent No. 6,630,599 [Patent Document 14] U.S. Patent Publication No. 2007 / 123,673 [Patent Document 15] European Patent No. 385,918 [Patent Document 16] European Patent No. 550,744 [Patent Document 17] International Publication No. 91 / 12243 Brochure [Patent Document 18] International Publication No. 02 / 42383 Brochure [Patent Document 19] International Publication No. 03 / 06568 Brochure [Patent Document 20] International Publication No. 2007 / 051738 Brochure [Patent Document 21] International Publication No. 2008 / 098885 Brochure [Patent Document 22] International Publication No. 2008 / 098887 Brochure [Patent Document 23] International Publication No. 2011 / 022457 Brochure [Patent Document 24] International Publication No. 2011 / 085280 Brochure [Patent Document 25] International Publication No. 2011 / 022457 Brochure [Patent Document 26] International Publication No. 2011 / 056682 Brochure [Non-patent literature]

[0013] [Non-Patent Document 1] Kim et al. (Uzbek Chemical Journal, Volume17, Issue2, Pages 48-50, 1973).

[0014] [Means for solving the problem] One object of the present application relates to a polymer obtained from a reaction mixture having (i) at least one dihydroxylactam moiety, and (ii) at least one functional moiety having a hydroxyl reactive functional group, wherein (i) and (ii) are each independently present in an amount from about 0.01 mol % to about 99.99 mol %, and the polymer is selected from the group consisting of polyesters, polycarbonates, polyethers, poly(ester ethers), poly(ester amides), polyimides, polyamides, polyacrylates, and poly(ester imides), or wherein each of (i) and (ii) is present in an amount other than 50 mol %, and the polymer is a polyurethane.

[0015] One object of the present application relates to a polymer obtained from a reaction mixture having (i) at least one dihydroxylactam moiety or modified dihydroxylactam moiety having a reactive functional group, the modified dihydroxylactam moiety having an additional functional group attached to the dihydroxylactam moiety, which may consist of esters, epoxies, ethers, urethanes, acrylates, anhydrides, and combinations thereof, and (ii) at least one functional moiety having a hydroxyl reactive functional group or a modified hydroxyl reactive functional group, each of (i) and (ii) being independently present in an amount of from about 0.01 mol % to about 99.99 mol %, and the polymer is selected from the group consisting of polyesters, polycarbonates, polyethers, poly(ester ethers), poly(ester amides), polyimides, polyamides, polyacrylates, and poly(ester imides), and polyurethanes.

[0016] Another object of the present application relates to a polymer obtained from a reaction mixture, said reaction mixture comprising: (i) a polymer selected from the group consisting of: [ka] A dihydroxylactam moiety selected from the group consisting of:

[0017] wherein n is an integer in the range of 1 to 6, and (ii) at least one functional moiety having a hydroxyl-reactive functional group, wherein (i) and (ii) are each independently present in an amount from about 0.01 mol % to about 99.99 mol %, and the polymer is selected from the group consisting of polyesters, polycarbonates, polyethers, poly(ester ethers), poly(ester amides), polyimides, polyamides, polyacrylates, and poly(ester imides); or wherein each of (i) and (ii) is present in an amount other than 50 mol %, and the polymer is a polyurethane.

[0018] 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-dihydroxypropyloxy)ethyl]-2-pyrrolidone; and (ii) poly(D,L-lactide). wherein (i) and (ii) are each independently present in an amount from about 0.01 mol % to about 99.99 mol %, and the polymer is a polyester.

[0019] Another object of the present application relates to a polymer obtained from a reaction mixture having (i) N-(2,3-dihydroxypropyl)-2-pyrrolidone and / or 1-[2-(2,3-dihydroxypropyloxy)ethyl]-2-pyrrolidone, and (ii) diphenyl carbonate, (i) and (ii) each independently being present in an amount from about 0.01 mol % to about 99.99 mol %, and the polymer is a polycarbonate.

[0020] Yet another object of the present application relates to a polymer obtained from a reaction mixture having (i) N-(2,3-dihydroxypropyl)-2-pyrrolidone and / or 1-[2-(2,3-dihydroxypropyloxy)ethyl]-2-pyrrolidone, (ii) dibromoethane, and (iii) a glycidyl ether, wherein (i), (ii) and (iii) are each independently present in an amount from about 0.01 mol % to about 99.99 mol %, and wherein the polymer is a polyether.

[0021] Another object of the present application relates to a polymer obtained from a reaction mixture having (i) N-(2,3-dihydroxypropyl)-2-pyrrolidone and / or 1-[2-(2,3-dihydroxypropyloxy)ethyl]-2-pyrrolidone, and (ii) 1,4-dibromobutane, reacting the product of (i) and (ii) with adipic acid chloride or adipic acid, wherein (i), (ii) and (iii) are each independently present in an amount of about 0.01 mol % to about 99.99 mol %, and the polymer is a polyester ether.

[0022] A different object of the present application relates to a polymer obtained from a reaction mixture having (i) N-(2,3-dihydroxypropyl)-2-pyrrolidone and / or 1-[2-(2,3-dihydroxypropyloxy)ethyl]-2-pyrrolidone, and (ii) an α-amino acid under p-toluenesulfonic acid, reacting the product of (i) and (ii) with (iii) bis(p-nitrophenyl succinate), wherein (i), (ii) and (iii) are each independently present in an amount of about 0.01 mol % to about 99.99 mol %, and the polymer is a polyesteramide.

[0023] A different object of the present application relates to a polymer obtained from a reaction mixture having (i) N-(2,3-dihydroxypropyl)-2-pyrrolidone and / or 1-[2-(2,3-dihydroxypropyloxy)ethyl]-2-pyrrolidone, and (ii) p-fluoronitrobenzene, wherein the product of (i) and (ii) is further hydrogenated to diamine (iii), and (iv) reacted with pyromellitic dianhydride, and wherein (i), (ii) and (iv) are each independently present in an amount of from about 0.01 mol % to about 99.99 mol %, and wherein the polymer is a polyimide.

[0024] Another object of the present application relates to a polymer obtained from a reaction mixture having (i) N-(2,3-dihydroxypropyl)-2-pyrrolidone and / or 1-[2-(2,3-dihydroxypropyloxy)ethyl]-2-pyrrolidone, and (ii) p-fluoronitrobenzene, wherein the product of (i) and (ii) is further hydrogenated to diamine (iii), and (iv) reacted with adipoyl chloride or adipic acid, and wherein (i), (ii) and (iv) are each independently present in an amount of about 0.01 mol % to about 99.99 mol %, and wherein the polymer is a polyamide.

[0025] Yet another object of the present application relates to a polymer obtained from a reaction mixture having (i) N-(2,3-dihydroxypropyl)-2-pyrrolidone and / or 1-[2-(2,3-dihydroxypropyloxy)ethyl]-2-pyrrolidone, and (ii) methacryloyl chloride, reacting the product of (i) and (ii) with (iii) methyl methacrylate, and (i), (ii) and (iii) are each independently present in an amount of about 0.01 mol % to about 99.99 mol %, and the polymer is a polyacrylate.

[0026] Yet another object of the present application relates to a polymer obtained from a reaction mixture having (i) N-(2,3-dihydroxypropyl)-2-pyrrolidone and / or 1-[2-(2,3-dihydroxypropyloxy)ethyl]-2-pyrrolidone, and (ii) p-fluoronitrile, the product of (i) and (ii) is further hydrogenated to diamine (iii), and (iv) reacted with (iv) N-(4-chlorocarbonylphenyl), and (i), (ii) and (iv) are each independently present in an amount of about 0.01 mol % to about 99.99 mol %, and the polymer is a polyesterimide.

[0027] 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-dihydroxypropyloxy)ethyl]-2-pyrrolidone, and (ii) a) isophorone diisocyanate, b) polyethylene glycol, and optionally c) octanol, wherein each of (i) and (ii) is present in an amount other than 50 mol %, and wherein the polymer is a polyurethane.

[0028] Another object of the present application relates to a composition comprising: (I) a polymer obtained from a reaction mixture having (i) at least one dihydroxylactam moiety, and (ii) at least one functional moiety having a hydroxyl reactive functional group, (i) and (ii) each independently being present in an amount of from about 0.01 mol % to about 99.99 mol %, and the polymer is selected from the group consisting of polyesters, polycarbonates, polyethers, poly(ester ethers), poly(ester amides), polyimides, polyamides, polyacrylates, and poly(ester imides), or each of (i) and (ii) being present in an amount other than 50 mol %, and the polymer is a polyurethane; and (II) one or more additives.

[0029] Another object of the present application relates to a personal care composition comprising: (I) a polymer obtained from a reaction mixture having (i) at least one dihydroxylactam moiety, and (ii) at least one functional moiety having a hydroxyl reactive functional group, (i) and (ii) each independently being present in an amount of from about 0.01 mol % to about 99.99 mol %, and the polymer is selected from the group consisting of polyesters, polycarbonates, polyethers, poly(ester ethers), poly(ester amides), polyimides, polyamides, polyacrylates, and poly(ester imides), or each of (i) and (ii) being present in an amount other than 50 mol %, and the polymer is a polyurethane; and (II) one or more pharma- ceutically acceptable additives.

[0030] Another object of the present application relates to a coating composition comprising: (I) a polymer obtained from a reaction mixture having (i) at least one dihydroxylactam moiety, and (ii) at least one functional moiety having a hydroxyl reactive functional group, (i) and (ii) each independently being present in an amount of from about 0.01 mol % to about 99.99 mol %, and the polymer being selected from the group consisting of polyesters, polycarbonates, polyethers, poly(ester ethers), poly(ester amides), polyimides, polyamides, polyacrylates, and poly(ester imides), or each of (i) and (ii) being present in an amount other than 50 mol %, and the polymer being a polyurethane; and (II) one or more coating additives.

[0031] Another object of the present application relates to a pharmaceutical composition comprising: (I) a polymer obtained from a reaction mixture, the reaction mixture having (i) N-(2,3-dihydroxypropyl)-2-pyrrolidone and / or 1-[2-(2,3-dihydroxypropyloxy)ethyl]-2-pyrrolidone, and (ii) poly(D,L-lactide), wherein (i) and (ii) are each independently present in an amount of from about 0.01 mol % to about 99.99 mol %, and the polymer is a polyester; and (II) one or more pharma- ceutically acceptable excipients.

[0032] Another object of the present application relates to a process for preparing a polymer, the process comprising the steps of: (A) preparing a polymer having (i) at least one dihydroxylactam moiety, and (ii) at least one functional moiety having a hydroxyl-reactive functional group, wherein (i) and (ii) are each independently present in an amount of about 0.01 mol % to about 99.99 mol %, and the polymer is selected from the group consisting of polyesters, polycarbonates, polyethers, poly(ester ethers), poly(ester amides), polyimides, polyamides, polyacrylates, and poly(ester imides); 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) with a solvent in a reaction vessel under an inert gas atmosphere; (C) stirring and maintaining the reaction mixture of (B) at a temperature of 55-70° C. for about 30 minutes; and (D) reacting (C) with a solvent to form a polymer having a hydroxyl-reactive functional group. (E) catalytically polymerizing said (D) for 3 to 5 hours; and (F) recovering the desired polymer from said (E).

[0033] Yet another object of the present application relates to a process for preparing a polymer, the process comprising the steps of: (A) formulating a polymer having (i) at least one dihydroxylactam moiety, and (ii) at least one functional moiety having a hydroxyl-reactive functional group, wherein (i) and (ii) are each independently present in an amount of about 0.01 mol % to about 99.99 mol %, and the polymer is selected from the group consisting of polyesters, polycarbonates, polyethers, poly(ester ethers), poly(ester amides), polyimides, polyamides, polyacrylates, and poly(ester imides), 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) into a reaction vessel under an inert gas atmosphere; (C) stirring and maintaining the reaction mixture of (B) at a temperature of 65-80° C. for about 30 minutes; and (D) reacting (C) with (D) a hydroxyl-reactive functional group having at least one dihydroxylactam moiety ... (E) polymerizing said (D) with a catalyst; (F) raising the temperature of said (E) to 90-110° C. and maintaining said temperature for about 2-3 hours; and (G) recovering the desired polymer from said (F). DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0034] Detailed Description of the Invention Before describing at least one embodiment of the present disclosure in detail, it is to be understood that the present disclosure is not limited to the details of the configuration and arrangement of components, steps or methodologies set forth in the following description or drawings within this application. The present disclosure is capable of other embodiments and of being practiced or carried out in various ways. Moreover, 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.

[0035] Unless otherwise defined herein, technical terms used in connection with this disclosure shall have meanings commonly understood by those of ordinary skill in the art. Further, unless otherwise required by context, singular terms include plurals and plural terms include the singular.

[0036] All patents, published patent applications, and non-patent literature mentioned herein 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 literature mentioned in any part of this application are expressly incorporated by reference in their entirety into this specification to the same extent as if each individual patent or publication was specifically and individually incorporated by reference.

[0037] All of the descriptions and / or methods described herein can be made and executed without undue experimentation in light of the present disclosure. Although the descriptions and / or methods of the present disclosure are described in terms of preferred embodiments, it will be apparent to those skilled in the art that changes can be applied to the descriptions and / or methods described herein, and to the steps or sequence of steps in the methods, without departing from the concept, spirit and scope of the present 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 present disclosure.

[0038] As utilized in accordance with the present disclosure, the following terms, unless otherwise indicated, shall be understood to have the following meanings:

[0039] The use of the word "a" or "an" when used in connection with the term "comprising" means "one," but is consistent with the meanings "one or more," "at least one," and "one or more than one." The use of the term "or" means "and / or," unless otherwise specified to refer to alternatives only when the alternatives are mutually exclusive, but the present disclosure supports a definition that refers only to alternatives and "and / or." Throughout this application, the term "about" indicates that the value includes an inherent error variation for the device in which the method of determining the value or variation present in the subject of study is employed to quantify. For example, and not as a limitation, when the term "about" is utilized, the indicated value may vary by + or - 12%, or 11%, or 10%, or 9%, or 8%, or 7%, or 6%, or 5%, or 4%, or 3%, or 2%, or 1%. The term "at least one" should be understood to include one as well as any quantity 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" can go up to 100 or 1000 or more based on the item to which it is attached. Additionally, the quantity 100 / 1000 should not be considered limiting when lower or higher limits can also produce satisfactory results. Additionally, use of the term "at least one of X, Y, and Z" should be understood to include X alone, Y alone, and Z alone, as well as any combination of X, Y, and Z. The use of ordinal terminology (i.e., "first," "second," "third," "fourth," etc.) is solely for the purpose of differentiating between two or more items and does not imply any sequence or ordering or importance of one item relative to other items, nor any additional ordering, unless otherwise stated.

[0040] Reference to "one embodiment" or "one aspect" or "one version" or "one objective" of the present invention or "another embodiment" or "another aspect" or "another version" or "another objective" may include one or more of such embodiments, aspects, versions or objectives unless the context clearly indicates otherwise.

[0041] The term "at least one" refers to any quantity from one to more 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" can reach 100 or 1000 or more depending on the item to which it is attached.

[0042] All percentages, parts, proportions, and ratios set forth herein are by weight of the total composition unless otherwise specified. All such weights pertaining to listed ingredients are based on the active level and, therefore, do not include solvents or by-products that may be included in commercially available materials, unless otherwise specified.

[0043] All references to singular features or limitations of the invention may include the corresponding plural features or limitations unless expressly stated otherwise or unless the context in which the reference is made makes clear to the contrary.

[0044] Numeric ranges used herein are intended to include all numbers and subsets of numbers contained within the range, whether or not expressly stated, and these numerical ranges should be construed as providing support to any claim that contemplates any number or subset of numbers within that range.

[0045] As used herein, the words "comprising" (and any form of comprising, e.g., plural "comprise" and singular "comprises"), having (and any form of having, e.g., plural "have" and singular "has"), including (and any form of including, e.g., singular "includes" and plural "include"), containing (and any form of containing, e.g., singular "contains" and plural "contain") are inclusive or open-ended and do not exclude additional, unrecited elements or method steps. As used herein, the terms "or combinations thereof" and "and / or combinations thereof" refer to all permutations and combinations of the items listed preceding the term. For example, "A, B, C, or combinations thereof" is intended to include at least one of A, B, C, AB, AC, BC, or ABC, and, where order is important in a particular context, at least one of BA, CA, CB, CBA, BCA, ACB, BAC, or CAB. Continuing with this example, combinations containing repeats of one or more items are expressly included, such as AAA, AAB, BBC, AAABCCCC, CBBAAA, CABABB, etc. One of skill in the art will understand that generally there are no limitations on the number of items or on any combination of items unless otherwise clear from the context.

[0046] For purposes of the following detailed description, other than as provided by any operating examples or otherwise, for example, the numerical values ​​expressing amounts of ingredients used in the specification and claims are to be understood as being modified in all instances by the term "about." The numerical parameters set forth in the specification and appended claims are approximations that may vary depending upon the desired properties to be obtained by the practice of the invention.

[0047] As used herein, the terms "or combinations thereof," "and combinations thereof," and "combinations thereof" refer to all permutations and combinations of the items listed preceding the term.

[0048] The term "about" refers to a range of plus or minus 10% of a particular value. For example, the phrase "about 200" includes ±10% of 200, or from 180 to 220.

[0049] The term "monomer" refers to a small molecule that chemically bonds during polymerization to one or more monomers of the same or different type to form a polymer.

[0050] The term "polymerization" or "polymerizing" refers to a process of chemically reacting monomer compounds to form polymer chains. The polymer chains can be in alternating, block or random arrangement. The type of polymerization process can be selected from a variety of methods and can include the following non-limiting examples: polycondensation, step-growth polymerization, and free radical polymerization.

[0051] The term "macromolecule" refers to any large molecule, including a polymer.

[0052] The term "polymer" refers to a macromolecule having one or more types of monomeric residues (repeating units) joined by covalent chemical bonds. Non-limiting examples of polymers include homopolymers and non-homopolymers such as copolymers, terpolymers, tetrapolymers and higher analogues.

[0053] The term "heteroatom" refers to oxygen, nitrogen, sulfur, silicon, phosphorus, or halogen. Heteroatoms can be present as part of one or more heteroatom-containing functional groups. Non-limiting examples of heteroatom-containing functional groups include ether groups, hydroxyl groups, epoxy groups, carbonyl groups, carboxamide groups, carboxylic ester groups, carboxylic acid groups, imine groups, imide groups, amine groups, sulfonic acid groups, sulfonamide groups, phosphonic acid groups, and silane groups. Heteroatoms can also be present as part of rings, such as in heteroaryl and heteroarylene groups.

[0054] The term "moiety" refers to a portion of a molecule or a functional group of a molecule.

[0055] The term "lactam" refers to a group having the structure: [ka] where A is a functionalized or non-functionalized alkylene or alkenyl group having 2 to 50 carbon atoms, and is between the groups shown below in formula (3) and (4), i.e. [ka] Based on [ka] and R is selected from the group consisting of hydrogen, functionalized or non-functionalized alkyl groups, cycloalkyl groups, alkenyl groups, and aryl groups, any of which may or may not have heteroatoms.

[0056] The lactam-containing moiety can have a general lactam structure including β-lactam, γ-lactam, δ-lactam, and ε-lactam. In one non-limiting embodiment, the lactam-containing moiety can have a lactam structure including β-propiolactam, γ-butyrolactam, δ-valerolactam, and ε-caprolactam.

[0057] The term "alkyl" refers to a C1-C60 monovalent straight, branched, or cyclic chain, functionalized or unfunctionalized, optionally containing one or more heteroatoms. In particular, alkyl is a C1-C45 group, more particularly a C1-C30 group. In particular, also 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, iso-norbornyl, n-dodecyl, tert-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, and n-eicosyl.

[0058] The term "branched and unbranched alkyl groups" refers to alkyl groups that can be straight chain or branched. For example, the alkyl groups have 1 to 60 carbon atoms, more specifically 1 to 30 carbon atoms, and even more specifically 1 to 6 carbon atoms. Branched groups include isopropyl, tert-butyl, and the like.

[0059] The term "alkylene" refers to a divalent linear, branched or cyclic chain, C1-C6, optionally with one or more heteroatoms, which may be functionalized or not. 50 In particular, alkylene refers to a group having a C1-C 45 More specifically, the C1-C 30 In particular, non-limiting examples of alkylene groups include -CH-, -CH-CH-, -CH(CH)-CH-, -CH-CH(CH), -C(CH)-CH-, -CH-C(CH)-, CH(CH)-CH(CH)-, -C(CH)-C(CH)-, -CH-CH-CH-, -CH(CH)-CH(CH)-, -C(CH)-C(CH)-, -CH-CH-CH-, -CH(CH)-CH-CH-, -CH- These include 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-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-, cyclopropylene, cyclobutylene, cyclopentylene, cyclohexylene, and so on.

[0060] The term "aryl" refers to a functional group derived from an aromatic hydrocarbon. The aromatic hydrocarbon may be monocyclic or polycyclic. Examples of monocyclic aryl groups include phenyl, tolyl, xylyl, mesityl, cumenyl, and the like. Examples of polycyclic aryl groups include naphthyl, anthryl, phenanthryl, and the like. The aryl group may have at least one substituent selected from halogen, hydroxyl, cyano, carboxy, carbamoyl, nitro, amino, aminomethyl, lower alkyl, lower alkoxy, mercapto, trichloroethyl, or trifluoroethyl. Such substituted aryl groups include 2-fluorophenyl, 3-nitrophenyl, 4-nitrophenyl, 4-methoxyphenyl, 4-hydroxyphenyl, and the like.

[0061] The term "cycloalkyl group" refers to a non-aromatic monocyclic or polycyclic chain system having about 3 to about 10 carbon atoms. The cycloalkyl group may be partially unsaturated. The cycloalkyl group may also be substituted with alkyl group substituents as defined herein. The cycloalkyl chain may contain oxygen, sulfur, or a substituted or unsubstituted nitrogen atom, and the nitrogen substituent may be hydrogen, an alkyl group, a substituted alkyl group, an aryl group, or a substituted aryl group, thereby resulting in a heterocyclic group. Representative monocyclic cycloalkyl rings include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and the like. Additionally, the cycloalkyl group may be substituted with a linking group such as an alkyl group, an alkylene group, and the like to form a cyclopropylmethyl group, a cyclobutylmethyl group, and the like. The cycloalkyl group may further be a polycyclic cycloalkyl ring, such as adamantyl, octahydronaphthyl, decalin, camphor, camphane, and noradamantyl.

[0062] The term "functionalized" refers to the state of a moiety in which one or more functional groups have been introduced by one or more functionalization reactions known to those skilled in the art. In particular, 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 addition, aldol condensation, Cannizzaro reaction, Mannich reaction, Claisen condensation, Suzuki coupling, and the like. In particular, functionalization of a moiety replaces one or more hydrogens in the moiety with one or more non-hydrogen groups, such as alkyl groups, alkoxy groups, cycloalkyl groups, alkenyl groups, cycloalkenyl groups, alkynyl groups, and / or aryl groups. Specific non-limiting examples of cycloalkyl groups include cyclopentane, cyclohexane, cycloheptane, etc. Specific non-limiting examples of alkoxy groups include methoxy, ethoxy, n-propoxy, isopropoxy, etc. Specific non-limiting examples of aryl groups include benzene, naphthalene (2 rings), anthracene (3 rings), etc.

[0063] The terms "pharmaceutical acceptable" and "cosmetically acceptable" refer to molecular entities and compositions that are generally regarded as safe. In particular, as used herein, the terms "pharmaceutical acceptable" and "cosmetically acceptable" refer to those approved by the regulatory authorities of an appropriate governmental agency or listed in the United States Pharmacopoeia or other drug classes recognized for use in animals in general, and more specifically, in humans.

[0064] The terms "physically active ingredient" and "cosmetically acceptable" refer to any ingredient that is deemed to have a therapeutic effect when administered to a subject in need thereof and further regulated by pharmaceutical agencies such as CDER, EMEA, TAG, etc. Pharmaceutical active ingredients can act systemically when taken orally or locally when present on the skin, such as in the oral cavity. They can also be delivered through the skin, such as in a transdermal delivery system.

[0065] All percentages, ratios and proportions used herein are on a weight basis unless otherwise specified.

[0066] The present disclosure contemplates a polymer obtained from a reaction mixture having (i) at least one dihydroxylactam moiety, and (ii) at least one functional moiety having a hydroxyl reactive functional group, wherein (i) and (ii) are each independently present in an amount from about 0.01 mol % to about 99.99 mol %, and the polymer is selected from the group consisting of polyesters, polycarbonates, polyethers, poly(ester ethers), poly(ester amides), polyimides, polyamides, polyacrylates, and poly(ester imides), or wherein each of (i) and (ii) is present in an amount other than 50 mol %, and the polymer is a polyurethane.

[0067] According to one embodiment, the dihydroxylactam moiety has the following chemical structure: [ka] It has the following structure: wherein "R" is independently selected from the group consisting of hydrogen, functionalized and non-functionalized alkyl groups, cycloalkyl groups, alkenyl groups, and aryl groups, any of the foregoing groups may be linear or branched, with or without heteroatoms; "A" is an alkylene or alkenylene group containing 2 to 50 carbon atoms, and wherein 2 to 4 of the carbon atoms are between the following groups: [ka] Base and [ka] is present in a lactam ring between the A polymer, wherein "n" is an integer in the range of 1 to 55 and "m" is an integer in the range of 0 to 5.

[0068] More specifically, between the following groups: [ka] Base and [ka] Each A in the lactam ring between the groups is selected from the following (propylene) and (butylene) groups: [ka] The compounds may be independently selected from the group consisting of:

[0069] More specifically, between the following groups: [ka] Base and [ka] Each A in the lactam ring between the groups is independently selected from the following groups: [ka] It can be said that

[0070] More specifically, each R is independently selected from the group consisting of hydrogen, functionalized and non-functionalized alkyl groups, cycloalkyl groups, alkenyl groups, and aryl groups containing 1 to 10 carbon atoms, any of which may contain or not contain heteroatoms. More specifically, each R may contain 1 to 8 carbon atoms. More specifically, each R may contain 1 to 6 carbon atoms.

[0071] Non-limiting examples of the dihydroxylactam moiety include: [ka] There are Here, n is an integer in the range of 1 to 6, and “m” is an integer in the range of 0 to 6.

[0072] According to one embodiment, the dihydroxylactam moiety is selected from the group consisting of N-(2,3-dihydroxypropyl)-2-pyrrolidone, 1-[2-(2,3-dihydroxypropyloxy)ethyl]-2-pyrrolidone, and combinations thereof.

[0073] According to yet another embodiment, the dihydroxylactam moiety is present in an amount of about 0.01% to about 99.0% by weight of the total reaction mixture. According to another embodiment, other possible ranges of the dihydroxylactam moiety compound include, but are not limited to, about 0.1% to about 10% by weight, 10% to about 20% by weight, 20% to about 30% by weight, 30% to about 40% by weight, 40% to about 50% by weight, 50% to about 60% by weight, 60% to about 70% by weight, 70% to about 80% by weight, 80% to about 90% by weight, and 90% to about 99.9% by weight.

[0074] 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 containing alcohols, (p) esters, (q) amines, (r) alkyl halides, (s) dihalogenomethanes, and combinations thereof.

[0075] According to another embodiment, the carbamate is selected from the group consisting of hydroxyethyl carbamate, hydroxypropyl carbamate, hydroxybutyl carbamate, and combinations thereof.

[0076] According to one embodiment, the acyl halide compound is selected from the group consisting of acryloyl chloride, succinyl chloride, methacryloyl chloride, crotonoyl 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, pentadecenoyl chloride, 2-cyclohexene 1 carbonyl chloride, 2-thiopheneacetyl chloride, and combinations thereof.

[0077] According to another embodiment, the sulfonyl halide compound is selected from the group consisting of methanesulfonyl chloride, benzenesulfonyl chloride, and combinations thereof.

[0078] According to another embodiment, the isothiocyanate compound is selected from the group consisting of methyl isothiocyanate, allyl isothiocyanate, aryl isothiocyanate, and combinations thereof.

[0079] 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.

[0080] 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, vitrylene diisocyanate, cyclohexane diisocyanate (CHDI), bis-(isocyanatomethyl)cyclohexane (H6XDI), dicyclohexylmethane diisocyanate (H12MDI), dimer acid diisocyanate (DDI), trimethylhexamethylene diisocyanate, lysine diisocyanate and its methyl ester, isocyanate diisocyanate, methyl ester ... and the like. The isocyanic acid diisocyanate is selected from the group consisting of isophorone, methylcyclohexane diisocyanate, 1,5-naphthalene diisocyanate, xylylene and xylene diisocyanates and methyl derivatives, polymethylene polyphenyl isocyanate, chlorophenylene-2,4-diisocyanate, polyphenylene diisocyanate, isophorone diisocyanate (IPDI), hydrogenated methylene diphenyl isocyanate (HMDI), tetramethylxylene diisocyanate (TMXDI), hexamethylene diisocyanate (HDI), and the corresponding dimers, trimers, and oligomers, and combinations thereof.

[0081] 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-epoxycyclohexanecarboxylate, 3,4-epoxy-6-methylcyclohexylmethyl 3,4-epoxy-6-methylcyclohexanecarboxylate, dipentene dioxide, 2-(3,4-epoxycyclohexyl-5,5-spiro-3,4-epoxy)cyclohexane meta-dioxane, and combinations thereof.

[0082] According to another embodiment, the imine compound is selected from the group consisting of polyaldimines, hydroxyaldimines, polyketimines, hydroxyketimines, and combinations thereof.

[0083] According to another embodiment, the thiocarbonate compound is selected from the group consisting of bis-(phenylthiocarbonyloxymethyl) esters, bis-(isopropylthiocarbonyloxymethyl) esters, and combinations thereof.

[0084] According to another embodiment, the thiol compound is selected from the group consisting of glutathione, 3-acetyl-thiolpropionic acid, thioanhydrides, thioacids, and combinations thereof.

[0085] According to another embodiment, the aldehyde compound is selected from the group consisting of acetaldehyde diethylacetyl, propionaldehyde diethylacetyl, di(acetaldehyde diethylacetal), chloroacetaldehyde diethylacetal, and combinations thereof.

[0086] According to another embodiment, the aziridine compound is selected from the group consisting of 2,2-bis-hydroxymethylbutanol tris-[3-(1-aziridinyl)propionate], bis-N-aziridinomethane, and combinations thereof.

[0087] According to another embodiment, the acids and their anhydride compounds are selected from the group consisting of maleic acid, maleic anhydride, fumaric acid, citric acid, alkenylsuccinic anhydride, phthalic anhydride, terephthalic acid, succinic anhydride, tetrahydrophthalic anhydride, maleic anhydride copolymers, and combinations thereof.

[0088] 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 nano antimicrobial agents, disodium 4,4-diazidostilbene-2,2-disulfate, aromatic bisazide compounds, calcium azide, 4,4-diphenyldisulfonyl azide, p-toluenesulfonyl azide, and combinations thereof.

[0089] According to another embodiment, the phosphorus oxychloride compound is selected from the group consisting of phosphorus oxychloride, phosphorus oxybromide, and combinations thereof.

[0090] According to another embodiment, the ester compound is selected from the group consisting of dimethyl itaconate, di-n-butyl itaconate, vinyl xanthate, glycolide, ε-caprolactone, γ-caprolactone, poly(D,L-lactide), poly(L-lactide), poly(ε-caprolactone), poly(γ-caprolactone), polyglycolide, valerolactone, butralactone, polyether-polyesters, poly-anhydride-diol-polyesters, and combinations thereof.

[0091] According to another embodiment, the amine compound is selected from the group consisting of amino alcohols, methylamines, ethylamines, hexylamines, isopropylamines, isobutylamines, amylamines, cyclohexylamines, octylamines, benzylamines, dimethylamines, diethylamines, dipropylamines, dibutylamines, diphenylamines, dibenzylamines, ethylmethylamines, N-methylaniline, ethylenediamines, propylenediamines, butylenediamines, hexamethylenediamines, cyclohexylenediamines, piperazine, toluenediamines, isophoronediamines, N,N-dimethylaniline, N,N-dimethyl-1-naphthylamines, N,N-dimethyl-p-toluidine, N,N-diethylaniline, N,N-diallylaniline, 1-phenylpiperidine, and 4-phenylmorpholine, amino-ethoxylates, cocaamines, soy amines, and combinations thereof.

[0092] According to another embodiment, the alkyl halide compound is selected from the group consisting of bromohexane, bromododecane, bromohexadecane, 1-bromooctadecane, and combinations thereof.

[0093] According to another embodiment, the dihalogenomethane compound is selected from the group consisting of dibromomethane, dichloromethane, and combinations thereof.

[0094] According to yet another embodiment, the functional moiety having a hydroxyl reactive functional group is present in an amount of about 0.01% to about 99.0% by weight of the total reaction mixture. According to another embodiment, other possible ranges of the functional moiety having a hydroxyl reactive functional group include, but are not limited to, about 0.1% to about 10% by weight, 10% to about 20% by weight, 20% to about 30% by weight, 30% to about 40% by weight, 40% to about 50% by weight, 50% to about 60% by weight, 60% to about 70% by weight, 70% to about 80% by weight, 80% to about 90% by weight, and 90% to about 99.9% by weight.

[0095] The disclosure further contemplates a polymer obtained from a reaction mixture having (i) from about 0.01 mol % to about 99.99 mol % of at least one dihydroxylactam moiety, and (ii) from about 0.01 mol % to about 99.99 mol % of at least one functional moiety having a hydroxyl reactive functional group, the polymer being selected from the group consisting of polyesters, polycarbonates, polyethers, poly(ester ethers), poly(ester amides), polyimides, polyamides, polyacrylates, and poly(ester imides), or each of (i) and (ii) is present in an amount other than 50 mol %, and the polymer is a polyurethane.

[0096] According to another embodiment, the reaction mixture further comprises one or more non-lactam moieties.

[0097] According to another embodiment, the non-lactam moiety is a C1-C 18 Aliphatic / aromatic alcohols with carbon chain lengths of C1-C 18Alkoxylated alcohols with carbon chain lengths of 100 to 2000, ethylene glycol, alcohol meth(acrylates), polyvinyl alcohol, polycarbonate polyols, polybutylene glycol, polyethylene glycol, polypropylene glycol, hydroxy polyesters, hydroxy polyethers, hydroxy polythioesters, hydroxy polyacetals, hydroxy polycarbonates, polyether polyols, polyester polyols, polycarbonate polyols, hydroxy polyesters, hydroxy polyethers, hydroxy polythioesters, hydroxy polyacetals, hydroxy polycarbonates, aliphatic and aromatic polyether polyols, caprolactone polyols, poly(ethylene glycol)-soy amine, poly(ethylene glycol)-castor oil, poly(ethylene glycol)-hydrogenated castor oil, poly(ethylene glycol)-lanolin, poly(ethylene glycol)-lanolin wax, poly(ethylene glycol)-polyvinylidene fluoride, poly(ethylene glycol)-poly(vinyl acetate), poly(ethylene glycol)- The polyoxymethylene, poly(ethylene glycol)-ester, and combinations thereof, functionalized and non-functionalized compounds are selected from the group consisting of polyoxymethylene, poly(ethylene glycol)-ester, and combinations thereof.

[0098] According to yet another embodiment, the non-lactam moiety compound is present in an amount of about 0.01% to about 99.8% by weight of the total reaction mixture. According to another embodiment, other possible ranges of the non-lactam moiety include, but are not limited to, about 0.1% to about 10% by weight, 10% to about 20% by weight, 20% to about 30% by weight, 30% to about 40% by weight, 40% to about 50% by weight, 50% to about 60% by weight, 60% to about 70% by weight, 70% to about 80% by weight, 80% to about 90% by weight, and 90% to about 99.8% by weight.

[0099] The molecular weight of the dihydroxylactam functionalized polymer is in the range of about 3,000 g / mol to about 1,000,000 g / mol. Other suitable molecular weight ranges include, but are not limited to, about 10,000 g / mol to about 100,000 g / mol, about 100,000 g / mol to about 200,000 g / mol, about 200,000 g / mol to about 300,000 g / mol, about 300,000 g / mol to about 400,000 g / mol, and about 400,000 g / mol to about 500,000 g / mol. 0 g / mol, about 500,000 g / mol to about 600,000 g / mol, about 600,000 g / mol to about 700,000 g / mol, about 700,000 g / mol to about 800,000 g / mol, about 800,000 g / mol to about 900,000 g / mol, and / or about 900,000 g / mol to about 1,000,000 g / mol.

[0100] The present disclosure provides a polymer obtained from a reaction mixture, the reaction mixture comprising:

[0013] The present invention contemplates a polymer having (i) N-(2,3-dihydroxypropyl)-2-pyrrolidone and / or 1-[2-(2,3-dihydroxypropyloxy)ethyl]-2-pyrrolidone, and (ii) poly(D,L-lactide), wherein (i) and (ii) are each independently present in an amount from about 0.01 mol % to about 99.99 mol %, and the polymer is a polyester.

[0101] The present disclosure further contemplates a polymer obtained from a reaction mixture comprising (i) N-(2,3-dihydroxypropyl)-2-pyrrolidone and / or 1-[2-(2,3-dihydroxypropyloxy)ethyl]-2-pyrrolidone, and (ii) (a) isophorone diisocyanate, (b) polyethylene glycol, and optionally (c) octanol, wherein each of (i) and (ii) is present in an amount other than 50 mole %, and the polymer is a polyurethane.

[0102] The types of polymerization methods used to prepare the polymers of the present invention include, but are not limited to, polycondensation, step-growth polymerization, and free radical polymerization.

[0103] Non-limiting illustrative examples of polymeric structures of the invention prepared as described below by reacting (i) at least one dihydroxylactam moiety, and (ii) at least one functional moiety having a hydroxyl-reactive functional group, wherein (i) and (ii) are each independently present in an amount of from about 0.01 mol % to about 99.99 mol %, and the polymer is selected from the group consisting of polyesters, polycarbonates, polyethers, poly(ester ethers), poly(ester amides), polyimides, polyamides, polyacrylates, and poly(ester imides); or wherein each of (i) and (ii) is present in an amount other than 50 mol %, and the polymer is a polyurethane:

[0104] PDIOL-DIOL-diisocyanate based polyurethanes of the following structure: [ka] wherein the PDIOL-DIOL-diisocyanate polyurethane has a structure of x+y+z=100;

[0105] EPDIOL-DIOL-diisocyanate based polyurethanes of the following structure: [ka] wherein the EPDIOL-DIOL-diisocyanate polyurethane has a structure of x+y+z=100;

[0106] EPDIOL-DIOL-diisocyanate-alcohol based polyurethanes of the following structure: [ka] wherein x+y+z=100 and the alcohol can be hexanol;

[0107] EPDIOL-DIOL-DMPA-diisocyanate-alcohol based polyurethanes of the following structure: [ka] wherein x+y+z=100 and the alcohol can be ethanol; There is.

[0108] The disclosure further relates to a broad composition comprising: (I) a polymer obtained from a reaction mixture having (i) at least one dihydroxylactam moiety, and (ii) at least one functional moiety having a hydroxyl reactive functional group, (i) and (ii) each independently being present in an amount from about 0.01 mol % to about 99.99 mol %, and the polymer is selected from the group consisting of polyesters, polycarbonates, polyethers, poly(ester ethers), poly(ester amides), polyimides, polyamides, polyacrylates, and poly(ester imides), or each of (i) and (ii) being present in an amount other than 50 mol %, and the polymer is a polyurethane; and (II) one or more additives; and The composition is preferably a medicament for use in a pharmaceutical composition comprising:

[0109] According to one embodiment, the additive is useful in an application selected from the group consisting of adhesives, aerosols, agricultural products, anti-resoiling products, battery products, beverages, biocides, biomaterials, cement and construction products, cleaning products, paints and coatings, rheology modifiers, conductive materials, cosmetics, dental products, decorative pigments, detergents, dispersants, pharmaceuticals, electronics, encapsulation, food products, hair care products, home-industrial fixtures, inks and coatings, interlaminates, lithography solutions, thin film additives, metal working fluids, oil field products, paper sizing products, polishing products, personal care products, pharmaceuticals, pigment additives, ointments, plastics, textiles, lubricants, printing, refractive index modifiers, sequestrants, stain repellents, static control, and wood care products.

[0110] The compounds, monomers, and polymers described herein can be used alone or in combination with other ingredients in a variety of compositions and product forms, including, but not limited to, adhesives, aerosols, agricultural products, anti-resoiling products, battery products, beverages, biocides, biomaterials, cement and construction products, cleaning products, paints and coatings, rheology modifiers, conductive materials, cosmetics, dental products, decorative pigments, detergents, dispersants, pharmaceuticals, electronics, encapsulation, food, hair care products, home-industrial fixtures, inks and coatings, interlaminates, lithography solutions, thin film additives, metalworking fluids, oilfield products, paper sizing products, polishing products, personal care products, pharmaceuticals, pigment additives, ointments, plastics, textiles, lubricants, printing, refractive index modifiers, sequestrants, stain repellents, static control, and wood care products.

[0111] The term "personal care composition" refers to a composition intended for use on or in the human body. Without limitation, specific types of personal care compositions include hair care compositions (including styling and non-styling compositions), sun care compositions (including after-sun compositions), skin care compositions, and oral care compositions.

[0112] The personal care compositions can be formulated into any product form known to those of skill in the art.

[0113] Product form: Non-limiting hair care product forms include shampoos, conditioners, aerosols, mousses, sprays, mists, gels, waxes, creams, lotions, glues, pomades, spritz, solutions, oils, liquids, solids, W / O emulsions, O / W emulsions, suspensions, multiple emulsions, microemulsions, microencapsulated products, sticks, balms, tonics, pastes, reconstitutable products, nanoemulsions, solid lipid nanoparticles, liposomes, cubosomes, neosomes, putties, lacquers, serums, perms, volumizers, packs, flakes, 2-in-1 shampoo / conditioner products, and 3-in-1 shampoo / conditioner / styling products.

[0114] The composition according to the invention can also be in the form of an after-shampoo composition for permanent, straightening, waving, dyeing or bleaching, which may or may not be rinsed off, or a rinse composition, which should be applied before or after dyeing or bleaching, permanenting, straightening, mitigating frizz, waving, or even between two stages of the permanent or straightening process.

[0115] Non-limiting sun care product forms include solutions, liquids, creams, powders, lotions, gels, pastes, waxes, aerosols, sprays, mists, roll-ons, sticks, milks, emulsions, and wipes.

[0116] Non-limiting skin care product forms include solutions, oils, lotions, creams, ointments, liquids, gels, bars, W / O emulsions, O / W emulsions, milks, suspensions, microemulsions, dispersions, microencapsulated products, sticks, balms, tonics, pastes, mists, reconstitutable products, peels, soaps, aerosols, mousses, waxes, glues, pomades, spritz, putties, lacquers, serums, perms, powders, pencils, flakes, blushes, highlighters, tanning agents, concealers, and two-way bar products.

[0117] The compositions according to the invention may furthermore take the form of a skin-cleaning composition, in particular in the form of a solution or gel for the bath or shower, or in the form of a make-up-removing product.

[0118] The six non-limiting skin care product categories discussed below can be considered subsets of skin and sun care products.

[0119] (1) Eye care: Non-limiting eye care product forms include mascara, eyeliner, eyeshadow, eyelash curler, eyebrow pencil, and eye pencil.

[0120] (2) Lip care: Non-limiting lip care product forms include lipsticks, lip balms, lip pencils, lip glosses, lip sprays, clear lip bases, tinted lip moisturizers, and multi-functional color sticks that can also be used on the cheeks and eyes.

[0121] (3) Nail care: Non-limiting nail care product forms include nail polishes, nail varnishes, enamels, nail polish removers, home manicure products such as cuticle softeners and nail strengtheners, and artificial nails.

[0122] (4) Face care: Non-limiting face 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, spritz, facial wet wipes, putties, lacquers, serums, perms, powders, blushes, highlighters, tanning agents, facial masks, and concealers.

[0123] (5) Body Care: Non-limiting body care product forms include foams, peels, masks, gels, sticks, aerosols, lotions, salts, oils, balls, liquids, powders, peels, pearls, bar soaps, liquid soaps, body washes, cleansers, scrubs, creams, flakes, other bath and shower products, shaving products, wax products, and disinfectants.

[0124] (6) Foot care: Non-limiting foot care product forms include mousses, creams, lotions, powders, liquids, sprays, aerosols, gels, flakes, and scrubs.

[0125] Non-limiting oral care product forms include toothpastes, patches, gums, gels, powders, creams, solutions, lotions, liquids, dispersions, suspensions, emulsions, tablets, capsules, rinses, flosses, aerosols, strips, films, pads, bandages, microencapsulated products, syrups, and lozenges.

[0126] Additionally, personal care compositions are contemplated that include the polymers described herein that are complexed with iodine. These compositions can be used to treat skin conditions, non-limiting examples of which include dermatitis, bacterial infections, burns, rashes, and herpes. These complex compositions can be staining, nearly non-staining, or essentially non-staining.

[0127] Examples of relevant personal care compositions are described in U.S. Pat. Nos. 5,599,800, 5,650,166, 5,916,549, and 6,812,192, U.S. Patent Application Publication No. 2009 / 0317432, European Patent Nos. 556,660, 661,037, 661,038, 662,315, 676,194, 796,077, 970,682, 976,383, 1,415,654, and 2,067,467, and International Publication No. WO 2005 / 032506, each of which is incorporated herein by reference in its entirety.

[0128] It is further contemplated that the personal care compositions may be used in personal grooming products for men and / or women, and / or toiletry products such as sanitary napkins, baby diapers, adult diapers, feminine products, incontinence products, and other related products.

[0129] The present disclosure further relates to a coating composition having the above-mentioned dihydroxylactam-based polymer, which further comprises at least one coating agent selected from the group consisting of solvents / cosolvents, modifiers, thixotropic agents, binders, crosslinkers, pH modifiers, pigments / fillers, flow control agents, gloss control agents, coalescing agents, softening resins, surfactants, waxes, wetting agents, dispersants, plasticizers, antioxidants, UV radiation absorbers, biocides, extenders, colorants, adhesion promoters, defoamers / defoamers, drying agents, matting agents, and combinations thereof.

[0130] Examples of pigments / fillers can 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, silicon dioxide, silicic acid, silica fines, calcined silicic acid, precipitated silicic acid, silicates, talc, kaolin, barium sulfate, magnesium silicate, lead, lead oxide, barite, precipitated barium sulfate, gravel, and glass beads. Special pigments / fillers can include graphene, graphite, carbon nanotubes, carbon, copper, silver, nanosilver, titanium nanotubes, specially decorated inorganic particles and structures, and the like.

[0131] Non-limiting examples of solvents / co-solvents can include, but are not limited to, aromatic hydrocarbon solvents such as benzene, toluene, and xylene, ethylbenzene, isopropylbenzene, alcohols (ethylene glycol monobutyl ether, diethylene glycol monobutyl ether, hexanol, octanol, ethanol, isopropanol, butanol, n-butanol, ethylene glycol, diethylene glycol, ketones (acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexane), diacetone alcohol, dimethyl fumarate, n-methyl-2-pyrrolidone, butyrolactone, ethyl acetate, butyl propionate, water, and the like.

[0132] Non-limiting examples of binders include, but are not limited to, latex emulsion polymers, which are the polymerization product of one or more ethylenically unsaturated monomers. Examples of ethylenically unsaturated monomers can include, but are not limited to, acrylic acid, acrylonitrile, acetoacetoxyethyl methacrylate, acetoacetoxyethyl acrylate, butyl acrylate, butadiene, butyl methacrylate, butylacrylamide, chloromethylstyrene, crotonic acid, ethyl acrylate, ethylacrylamide, ethylene, ethyl methacrylate, ethylhexyl acrylate, 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, glycidyl methacrylate, hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, isobutyl acrylate, isobutyl methacrylate, isoprene, isooctyl acrylate, isooctyl itaconate methacrylate, methyl acrylate, octyl acrylate, octyl methacrylate, methyl methacrylate, methacrylic acid, α-methylstyrene, styrene, vinyl chloride, vinyl naphthalene, vinyl toluene, vinylidene chloride, vinyl acetate, and the like.

[0133] Other binders 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 polybasic acids, polyhydric alcohols, and fatty acids that may be unsaturated. Polybasic acids such as aromatic, aliphatic, and cycloaliphatic saturated and unsaturated compounds include, for example, adipic acid, chlorendic acid, heptanedioic acid, isophthalic acid, maleic acid, naphthalic acid, phthalic acid, sebacic acid, succinic acid, trimellitic acid, terephthalic acid, and tetrahydrophthalic acid. Polyhydric alcohol compounds include 1,3-butylene glycol, diethylene glycol, dipentaerythritol, dipropylene glycol, ethylene glycol, glycerin, 1,6-hexanediol, neopentyl glycol, pentaerythritol, propylene glycol, sorbitol, trimethylolethane, trimethylolpropane, and triethylene glycol. Fatty acids commonly used in alkyd resin manufacture include hydrogenated castor oil, coconut oil, cottonseed oil, fish oil, linseed oil, oiticica oil, tung oil, safflower oil, soybean oil, tall oil acids, and the like.

[0134] Polyurethane resins are formed from polyisocyanate compounds (aliphatic, aromatic, or combinations thereof). Examples of aliphatic isocyanates (isocyanates) include butane isocyanate, 4,4'-diisocyanatodicyclohexylmethane, hexamethylene diisocyanate, hexahydroxylylene diisocyanate, isophorone diisocyanate, 1-methyl-2,4(2,6)-diisocyanatocyclohexane, norbornane diisocyanate, and tetramethylxylene diisocyanate. Examples of aliphatic and aromatic isocyanates include 4,4'-biphenylene diisocyanate, 4-chloro-1,3-phenylene diisocyanate, 1,4-cyclohexylene diisocyanate, 1,10-deca-ethylene diisocyanate, methylene bis-(4-phenyl isocyanate), 4,4-methylene-bis(cyclohexyl isocyanate), 1,5-naphthalene diisocyanate, 1,3-phenylene diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 1,4-tetramethylene diisocyanate, 1,5-tetrahydronaphthalene diisocyanate, and many more.

[0135] In addition to isocyanates (isocyanates), alcohols and carboxylic acids forming polyester compositions can also be used to prepare polyurethane resins. The carboxylic acids can be aliphatic, cycloaliphatic, and / or aromatic in nature and can have halogen atoms and / or unsaturation. Suitable acids include adipic acid, azelaic acid, bis-glycol terephthalate, dimer fatty acid, dimethyl terephthalate, endomethylenetetrahydrophthalic anhydride, fumaric acid, glutaric anhydride, hexahydrophthalic anhydride, isophthalic acid, maleic acid, maleic anhydride, phthalic anhydride, phthalic acid, suberic acid, succinic acid, sebacic acid, tetrahydrophthalic anhydride, and tetrachlorophthalic anhydride. Examples of alcohols include 1,4-, 1,3-, and 2,3-butylene glycol, cyclohexanedimethanol (1,4-bis-hydroxymethylchlorohexane), diethylene glycol, dipropylene glycol, dibutylene glycol, ethylene glycol, 1,2-, and 1,3-propylene glycol, 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 that have carboxyl or carboxylate groups and are suitable for containing or potentially supporting ionic groups are contemplated. Such moieties may be constituted by tartaric acid, dimethylolacetic acid, 2,2-dimethylolpropionic acid, 2,2-dimethylolbutyric acid, and 2,2-dimethylolpentanoic acid.

[0136] Polyester compositions may also be made as part of the present invention. Polyesters having carboxyl groups and terminal carboxyl groups are contemplated. Additionally, polyesters comprised of lactones are contemplated. Polyesters obtained from a reaction mixture having at least one dihydroxylactam moiety and at least one functional moiety having a hydroxyl-reactive functionality, wherein the functional moiety having a hydroxyl-reactive functionality is selected from the group consisting of phthalic anhydride, isophthalic acid, maleic anhydride, chlorine / bromine containing anhydrides, and fumaric acid. Polyesters may further comprise any of C1-C 18 Aliphatic / aromatic alcohols with carbon chain lengths of C1-C 18 Alkoxylated alcohols with carbon chain lengths of 100 to 2000, ethylene glycol, alcohol meth(acrylates), polyvinyl alcohol, polycarbonate polyols, polybutylene glycol, polyethylene glycol, polypropylene glycol, hydroxy polyesters, hydroxy polyethers, hydroxy polythioesters, hydroxy polyacetals, hydroxy polycarbonates, polyether polyols, polyester polyols, polycarbonate polyols, hydroxy polyesters, hydroxy polyethers, hydroxy polythioesters, hydroxy polyacetals, hydroxy polycarbonates, aliphatic and aromatic polyether polyols, caprolactone polyols, poly(ethylene glycol)-soy amine, poly(ethylene glycol)-castor oil, poly(ethylene glycol)-hydrogenated castor oil, poly(ethylene glycol)-lanolin, poly(ethylene glycol)-lanolin wax, poly(ethylene glycol)-polyvinylidene fluoride, poly(ethylene glycol)-poly(vinyl acetate), poly(ethylene glycol)- Selected from the group consisting of functionalized and non-functionalized compounds of polyoxymethylene, poly(ethylene glycol)-esters, and combinations thereof;

[0137] Polycarbonates containing hydroxyl groups are useful and are prepared by reacting a diol with a dicarbonate such as diphenyl carbonate or phosgene.

[0138] Polyethers formed from polymers having diols and derived from ethylene oxide, propylene oxide, and / or tetrahydrofuran are also useful. Amine functionality can be employed to introduce terminal hydroxyl functionality to compounds such as diethanolamine, ethanolamine, N-methylethanolamine, propanolamine, N,N,N'-tris-2-hydroxyethyl-ethylenediamine.

[0139] Epoxy resins consist primarily of linear molecules. These molecules are formed from reacting bisphenols with halohydrins to produce epoxy resins containing epoxy groups. Common bisphenols include bisphenol-A, bisphenol-F, bisphenol-S, and 4,4'-dihydroxybisphenol. Common halohydrins include epichlorohydrin, dichlorohydrin, and 1,2-dichloro-3-hydroxypropane. An example of a commercially available epoxy resin is DER from The Dow Chemical Company. TM 333 and DER TM 661, EPON from Momentive Specialty Chemicals TM 828, EPON TM 836 and EPON TM 1001, Ciba-Geigy epoxy resins GT-7013, GT-7014, GT-7074, GT-259 from Huntsman, and Ancarez from Air Products. TM There is an AR 555.

[0140] Non-limiting examples of secondary rheology modifiers can include cellulose and cellulose derivatives, guar and guar derivatives, modified ureas, polyurethane thickeners and associated thickeners, alkali swellable emulsions (ASEs), hydrophobically modified alkali swellable emulsions (HASEs), hydrophobically modified polyurethanes (HEURs), hydrophobically modified polyethers (HMPEs), attapulgite, hydrophobically modified polyacetal polyethers (HMPAPEs), acrylate thickeners, amides and organic derivatives, fumed silica, synthetic layered silica, organoclays, mixed minerals, thixotropic boosters, polyalkylene ether derivatives, starches, polyacrylates, and the like.

[0141] Non-limiting examples of pH adjusters can include monoethanolamine, triethanolamine, methylaminoethanol, 2-amino-2-methyl-1-propanol, 2-(n-butylamino)ethanol, ammonium hydroxide, ammonia, caustic, potassium hydroxide, formic acid, acetic acid, citric acid, organic acids, mineral acids, hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, and the like.

[0142] Non-limiting examples of biocides include, but are not limited to, 2-n-octyl-3-isothiazolone, chlorothalonil, carbendazim, diuron, isothiazolone, 2-octyl-2H-isothiazol-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, methylene Bis(thiocyanate), 2-(thiocyano-methylthio)-benzothiazole, octylinone, barium metaborate, propiconazole, diiodomethyl p-tolylsulfone, 3-iodo-2-propynyl butyl carbamate, n-(trichloromethylthio)phthalimide, tributyltin benzoate, alkylamine hydrochloride, n-(trichloromethylthio)-4-cyclohexane-1,2-dicarboximide, 2-methylthio-4-tert-butyl-amino-6-cyclopropylamino-s-triazine, tetrachloroisophthalonitrile, zinc dimethyldithiocarbamate, zinc 2-mercaptobenzothiazole, trans-1,2-bis(n-propyl-sulfonyl ethane), 4,5-dichloro-2-n-octyl-3-(2H)-isothiazolone, 4,5-dichloro-2-n-octyl-4-isothiazoline 3-one (DCOIT), carbendazim, Irgarol, 10,10'-oxybisphenoxazine, triclosan, 2-methylthio-4-tert-butyl-amino-6-cyclopropylamino-s-triazine, n-cyclopropyl-N'-(1,1-dimethylethyl)-6-(methylthio)-1,3,5-triazine-2,4-diamine, zinc dimethyldithiocarbamate (ziram), Irgarol (registered trademark) ) 1051 (available from BASF), tributyltin oxide (TBTO), 5-chloro-methyl-2H-isothiazol-3-one / 2-methyl-2H-isothiazol-3-one (CITMIT), benzisothiazolinone (BIT), methylisothiazolinone (MIT), hexahydro-1,3,5-tris(2-hydroxyethyl)-S-triazine, sodium pyrithione, 2-pyridinethiol-1-yl, zinc oxide, 1,2-Benzisothiazolin-3-one, glutaraldehyde, 2,2-dibromo-3-nitrilopropionamide (DBNPA), poly(hexamethylene biguanide) hydrochloride (PHMB), 2-bromo-2-nitropropane-1,3-diol (bronopol), 1,2-dibromo-2-4-dicyanobutane, 1-bromo-1-(bromomethyl)-1,3-propanedicarbonitrile, 2,2-dibromo-3-nitro-propionamide, benzoyl bromoacetate, 1-bromo-1-(bromomethyl)-1,3-propanedicarbonitrile, dazomet, dodecylguanidine Hydrochloride, methylene dithiocyanate, 1-methyl-3,5,7-triaza-1-azoniaadamantane chloride, 2-bromo-4'-hydroxyacetophenone, dibromo-3-nitro-propionamide, 1,2-benzisothiazolin-3-one, hexahydrotriazine, bromo-β-nitrostyrene, ethyl dihydro-1H,3H-,5H-oxazolo(3,4-C)oxazole, acetoxy-2 4-Dimethyl-m-dioxane, nitrobutyl morpholine, ethyl-2-nitrotrimethylene dimorpholine, sodium o-phenylphenol, chloroallyl-3,5,7-azoniaadamantane chloride, sodium biphenylol, tributyltin benzoate, alkylamine hydrochloride, mixture of monocyclic oxazolidines, n-methyl-2-hydroxymethyleneoxypropyl-2'-hydroxypropylamine, sodium hydroxymethylglycinate, mixture of bicyclic oxazolidines, 1,3-bis(hydroxymethyl)-5,5'-dimethyl hydantoin, hydroxymethyl 5,5'-dimethyl hydantoin, 5-chloro-2-methyl-4-isothiazolin-3-one, 2-methyl-4-isothiazolin-3-one, 2-methyl-4-isothiazolin-3-one and combinations thereof.

[0143] Non-limiting examples of colorants can include pigments and / or dyes. Suitable pigment materials can be found in "Industrial Organic Pigments" by Hanger, "Dictionary of Pigments" by Ito, and "Printing Ink Manual" by Leach and Pierce. Examples of inorganic pigments can include, but are not limited to, pigment blacks (lamp, furnace, channel black), iron oxides (red, yellow, brown, black, clear, etc.), spinel black, chrome oxide green, chromate yellow, iron blue, zinc chromate, molybdate orange, molybdate red, ultramarine, cadmium, mixed phase pigments (nickel titanium yellow, chrome titanium yellow, cobalt green, cobalt blue, zinc iron brown, iron manganese black), all types of metal powders such as aluminum powder, gold powder, silver powder, copper powder, bronze powder, and brass powder, or flake pigments of these metals, mica flake pigments coated with metal oxides, oxide pigments in the form of mica, and the like.

[0144] The organic pigments can include, but are not limited to, monoazo pigments (acetoacetanilide, benzimidazolone, naphthol AS, pigmented b-naphthol dyes), disazo pigments (azo condensation pigments, dipyrazolones), polycyclic pigments (quinacridones, dioxazines, perylenes, diketopyrrolo-pyrroles, isoindolines), and metal complex pigments (Cu-phthalocyanines). Examples of dyes can include metal complex dyes, anionic dyes, azo dyes, and the like.

[0145] Cellulose derivatives include, but are 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), methyl hydroxypropyl cellulose (MHPC), methyl hydroxyethyl cellulose (MHEC), carboxymethyl methyl cellulose (CMMC), hydrophobically modified carboxymethyl cellulose (HMCMC), hydrophobically modified hydroxyethyl cellulose (HMHEC), hydrophobically modified hydroxypropyl ... Hydrophobically modified cellulose (HMHPC), hydrophobically modified carboxymethyl hydroxyethyl cellulose (HMCMHEC), hydrophobically modified hydroxypropyl hydroxyethyl cellulose (HMHPHEC), hydrophobically modified methyl cellulose (HMMC), hydrophobically modified methyl hydroxypropyl cellulose (HMMHPC), 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), microfibrillated cellulose (MFC).

[0146] Guar and guar derivatives can include, but are not limited to, hydroxyalkyl guars such as carboxymethyl guar, carboxymethyl hydroxypropyl guar, cationic hydroxypropyl guar, hydroxyethyl guar, hydroxypropyl guar, and hydroxybutyl guar, carboxyalkyl guars such as carboxymethyl guar, carboxypropyl guar, carboxybutyl guar, and the like.

[0147] Examples of defoamers or antifoaming agents can include, but are not limited to, silicone antifoamers having polysiloxane and hydrophobic particles, silicone-free antifoamers having hydrophobic particles and polymers, the silicone-free antifoamers including polymers, paraffinic mineral oils, mineral oils consisting of hydrophobic particles and polysiloxanes.

[0148] Surfactants can provide excellent surface tension reduction capabilities for wetting the substrate. Surfactants used in the present disclosure can be non-ionic and anionic surfactants.

[0149] Examples of non-ionic surfactants include, but are not limited to, C12-C18 fatty alcohol ethoxylates, C12-C14 fatty alcohol ethoxylates, C16-C18 fatty alcohol ethoxylates, C13-C15 oxoalcohol ethoxylates, C10-C18 oxoalcohol ethoxylates, C13 oxoalcohol ethoxylates, C10 Guerbet alcohol ethoxylates, C10 Guerbet alcohol alkoxylates, C10 oxoalcohol ethoxylates, alkyl polyglucosides (e.g., C 12-C14 fatty alcohol ethoxylates, C16-C18 fatty alcohol ethoxylates, C13-C15 oxoalcohol ethoxylates, C10-C18 oxoalcohol ethoxylates, C13 oxoalcohol ethoxylates, C10 Guerbet alcohol alkoxylates, C10 oxoalcohol ethoxylates, alkyl polyglucosides (e.g., C 12-C14 fatty alcohol ethoxylates in inorganic and organic carriers), and the like. C8-C10 alkyl polyglucosides, C8-C14 alkyl polyglucosides, C12-C14 alkyl polyglucosides, blends of C12-C10 alkyl polyglucosides), amine ethoxylates (e.g., oleylamine + 12EO, cocoamine + 12EO), amino polyols (e.g., triethanolamine + 18EO, ethylenediamine + 4PO), alkyl pyrrolidones (e.g., N-octyl pyrrolidone, N-butyl pyrrolidone, N-dodecyl pyrrolidone), resin precursors and additives (e.g., bisphenol A ethoxylates, BIS A + 3EO, BIS A + 4EO, BISA+6EO), emulsifiers and solubilizers (e.g. 4-C10-13-sec-alkyl derivatives of calcium benzenesulfonate, castor oil+~20EO, castor oil+~35EO, castor oil+~40EO, epoxidized vegetable oils, ethoxylated rapeseed oil, ethoxylated sorbitan esters, decyl alcohol+~3EO, C8 fatty alcohol+EO, fatty alcohol ethoxylates, C8-C10 fatty alcohol+~5EO, C12-C14 fatty alcohol+~50EO, ethoxylated sorbitan trioleate, castor oil ethoxylate, phenol ethoxylate, alcohol ethoxylate, ethoxylated mono / diglyceride), foam suppressors (e.g. polyalkoxyesters and solvents, fatty alcohol alkoxylates, carboxylic acid esters, phosphate esters, combinations of paraffin and silicon on a carrier, alkyl polyalkylene glycol esters, Guerbet alcohol C16+~2EO, fatty alcohol alkoxylates), low foaming non-isopropyl alcohols, On surfactants (e.g. fatty alcohol alkoxylates, modified fatty alcohol polyglycol ethers, amine alkoxylates, end-capped Guerbet alcohol alkoxylates, end-capped fatty alcohol alkoxylates, PO / EO block copolymers), lauramine oxides, cocamidopropylamine oxides, alkylamidopropyl betaines, polyglycol ethers of fatty diols, oleic acid amide +~10EO, emulsifiable methyl carboxylates, unsaturated fatty alcohol ethoxylates, fatty alcohol polyglycol ethers, fatty alcohol polyglycol ethers with fatty acids, unsaturated fatty alcohol ethoxylates), polyethylene glycols, polypropylene glycols, methyl polyethylene glycols, alkyl polyalkylene glycol copolymers, alkyl polypropylene glycols, multifunctional polyalkylene glycols, reactive polyalkylene glycols.

[0150] Other nonionic surfactants include, but are not limited to, alkylphenol ethoxylates such as nonylphenol ethoxylate and octylphenol ethoxylate, secondary alcohol ethoxylates (such as TERGITOL 100 available from The Dow Chemical Company), and the like. TM 15-S-9) as well as primary alcohol alkoxylates.

[0151] Examples of anionic surfactants include, but are not limited to, sodium lauryl ether sulfate + 2EO, sodium iso-tridecyl 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, sodium C12-C14 fatty alcohol ether sulfate + 1EO, sodium C12-C14 fatty alcohol ether sulfate + 2EO sodium salt, C12-C14 fatty alcohol ether sulfate + 3EO sodium salt, C8-C14 fatty alcohol sulfate ammonium salt, 2-ethylhexyl sulfate sodium salt, C16-C18 fatty alcohol sulfate sodium salt, C12 fatty alcohol sulfate sodium salt, C12-C18 fatty alcohol sulfate sodium salt, C16-C18 fatty alcohol sulfate sodium salt, C8 fatty alcohol sulfate sodium salt, linear C10-C13 alkyl benzene sulfonate sodium salt, linear C10-C13 alkyl benzene sulfonic acid sodium salt, and oleic acid sulfonate potassium salt are possible.

[0152] Other surfactants for use in the present disclosure can include, but are not limited to, ester quats, sodium salts of alkyl ether phosphates, sodium-N-lauryl-β-iminodipropionate, phosphate esters of fatty alcohol ethoxylates + 3EO, sodium salts of monoalkenyl sulfosuccinamates, sodium salts of monoalkenyl sulfosuccinates + 5EO, sodium salts of diisodecyl sulfosuccinates, sodium dioctyl sulfosuccinates, phosphate esters, amine salts of dodecylbenzene sulfosuccinates, phosphate alkyl esters, and the like.

[0153] Non-limiting examples of coalescent agents include ethylene glycol monobutyl ether acetate, diethylene glycol monoethyl ether, lower monoalkyl ethers of ethylene 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 o-toluate, 2-ethoxyethyl benzoate, 2-(2-ethoxyethoxy)ethyl p-Toluates, ), benzoates (e.g., 2-(2-ethoxyethoxy)ethyl benzoate, 2-propoxyethyl benzoate, 2-methoxy-1-methylethyl benzoate, 2-(2-methoxy-1-methylethoxy)-1-methylethyl benzoate, 2-propoxy-1-methylethyl benzoate), levulinic acid ester of 2-hexyl-1-decanol, levulinic acid ester of 1-tetradecanol / 2-hexyldecanol, dioctyl succinate, polytrimethylene ether glycol, hexylene glycol, butoxyethyoxypropanol, n-propoxypropanol, n- Butoxypropanol, diethylene glycol monobutyl ether acetate, phenyl glycol ether, 2,2,4-trimethylpentanediol-1,3-monoisobutyrate, n-dibutyl glutarate, n-dipentyl glutarate, n-dihexyl glutarate, n-diheptyl glutarate, n-dioctyl glutarate, n-diisobutyl glutarate, di-2-methylbutyl glutarate, di-4-methyl-2-pentyl glutarate, di-2-ethylhexyl glutarate, pentylol glutarate, tetrapropylene glycol monobutyl ether, etc. Mixtures of these compounds are also suitable as coalescents.

[0154] The coating composition having the dihydroxylactam polymer according to the present disclosure can be applied to various surfaces and substrates. These surfaces and substrates can include, but are not limited to, asphalt, cement, concrete, drywall, glass, masonry, metal, paper, plastic, textile, wallpaper, and wood. The coating composition according to the present disclosure can provide improved hiding power to the substrate coated with the composition.

[0155] The disclosure further contemplates 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-dihydroxypropyloxy)ethyl]-2-pyrrolidone, and (ii) poly(D,L-lactide), wherein (i) and (ii) are each independently present in an amount from about 0.01 mol % to about 99.99 mol %, and the polymer is a polyester; and (II) one or more pharma- ceutically acceptable excipients.

[0156] According to one embodiment, the pharma- ceutically acceptable excipient is selected from the group consisting of plasticizers, disintegrants, surface active agents, lubricants, glidants, carriers, anti-adherents, enhancers, wetting agents, pH modifiers, binders, dissolution modifiers, recrystallization inhibitors, coating agents, diluents, colorants, preservatives, antifoaming agents, antioxidants, buffers, acidifiers, alkalinizers, complexation enhancers, cryoprotectants, electrolytes, gelling agents, emulsifiers, dissolution enhancers, stabilizers, tonicity modifiers, flavors, sweeteners, complexing agents, fragrances, and viscosity modifiers.

[0157] The present disclosure further contemplates a process for preparing a polymer comprising the steps of: (A) formulating a polymer having (i) at least one dihydroxylactam moiety, and (ii) at least one functional moiety having a hydroxyl-reactive functional group, wherein (i) and (ii) are each independently present in an amount of from about 0.01 mol % to about 99.99 mol %, and the polymer is selected from the group consisting of polyesters, polycarbonates, polyethers, poly(ester ethers), poly(ester amides), polyimides, polyamides, polyacrylates, and poly(ester imides); 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) with a solvent in a reaction vessel under an inert gas atmosphere; (C) stirring and maintaining the reaction mixture of (B) at a temperature of 55-70° C. for about 30 minutes; and (D) reacting the polymer with a solvent to form a polymer having a hydroxyl-reactive functional group; charging (C) with additional reactive moieties; (E) catalytically polymerizing (D) for 3 to 5 hours; and (F) recovering the desired polymer from (E).

[0158] A solvent can be used in the synthesis of the polymer according to the present disclosure. Any solvent without active hydrogen can be used. Non-limiting examples of solvents can include acetone, dimethylacetamide, toluene, xylene, aliphatic hydrocarbons, dialkyl ethers of alkylene glycols, and diethoxymethane.

[0159] According to other embodiments, the solvent system is present in an amount of about 60% to about 90% by weight of the thickening system. In alternative embodiments, other possible ranges of the solvent system can include, but are not limited to, about 60% to about 70% by weight, about 70% to about 80% by weight, about 80% to about 90% by weight, and about 90% to about 99.9% by weight.

[0160] Catalysts can be used in the synthesis of polymers according to the present disclosure. Non-limiting examples of catalysts can include dibutyltin dilaurate, 1,4-diazabicyclo[2,2,2]octane, triethylamine, pyridine, and paratoluenesulfonic acid.

[0161] The present disclosure relates to a method of thickening a composition, comprising adding a dihydroxylactam based polymer as described above to said composition. Examples of compositions may include, but are not limited to, coating compositions, building compositions, personal care compositions, oilfield compositions, drilling fluids, drilling muds, cementing fluids, repair fluids, gravel fill muds, fracturing fluids, completion fluids, workover fluids, spacer fluids, household, industrial and institutional compositions, pharmaceutical compositions, food compositions, biocides, inks, papers, polishes, films, metalworking fluids, plastics, textiles, printing compositions, lubricants, preservatives, pesticides, and wood care compositions.

[0162] The polymers and their applications according to the present disclosure can be prepared and used according to the examples set forth below, which are presented for illustrative purposes of the present disclosure and are not intended to be limiting, e.g., on the preparation of the polymers and their applications. EXAMPLES

[0163] In the examples, the following abbreviations are used: EPDIOL : 1-[2-(2,3-dihydroxypropyloxy)ethyl]-2-pyrrolidone PEG1: Approximate value M n =7860, and M w Polyethylene glycol with =8240 PEG2: Approximate value M n =3640, and M w Polyethylene glycol with =3790 DBTD: Dibutyltin dilaurate HMDI: 4,4'-methylenebis(cyclohexyl isocyanate) HDI: Hexamethylene diisocyanate IPDI: Isophorone diisocyanate DMBA: Dimethylolbutyric acid DMAc: Dimethylacetamide MBPI: 4,4'-methylenebis(phenyl isocyanate) DMPA: Dimethylolpropionic acid MDEA: Methyl diethanolamine TEA: Triethylamine DMI: Dimethyl itaconate MA: Maleic anhydride Acc.Cl: acryloyl chloride GMA: Glycidyl methacrylate

[0164] Example 1: Reaction of EPDIOL with glycidol A mixture of glycidol (5.45 g) and EPDIOL (15 g) was mixed with a mixture of acetone and TEA (40 g) in a round bottom flask equipped with a stir bar and a heating mantle, and the mixture was stirred at 55 °C for 6 hours. The resulting mixture was clear, and the resulting product was analyzed by IR, showing the disappearance of epoxide absorption bonds in the 800 region and the formation of ether absorption bonds (1,100-1,200 cm). -1 ) was confirmed.

[0165] Example 2: Reaction of EPDIOL with succinyl chloride A mixture of succinyl chloride (11.44 g) and EPDIOL (15 g) was mixed with acetone (50 g) in a round bottom flask equipped with a stir bar and a heating mantle, and the mixture was stirred at 55° C. for 2 hours. The resulting mixture was dark brown in color, and the resulting product was found to have a peak at 1735 cm by IR. -1 Ester absorption binding was confirmed.

[0166] Example 3: Reaction of EPDIOL with DMI A mixture of DMI (11.65 g) and EPDIOL (15 g) was mixed with a mixture of acetone and TEA (50 g) in a round bottom flask equipped with a stir bar and a heating mantle, and the mixture was stirred at 55° C. for 4 hours. The resulting mixture was clear and the resulting product was found to have a peak at 2840 cm by IR. -1 The reduction of methoxy CH3 bonds and the formation of ester bonds at 1730 positions were confirmed.

[0167] Example 4: Reaction of EPDIOL with MA A mixture of MA (15 g) and EPDIOL (31.10 g) was mixed with acetone (65 g) in a round bottom flask equipped with a stir bar and a heating mantle, and the mixture was stirred at 55° C. for 6 hours. The resulting mixture was yellowish and the resulting product had a viscosity of 1850 cm -1 Anhydride disappearance, 1774 cm -1 and 1717 cm -1 The appearance of an ester peak was confirmed.

[0168] Example 5: Reaction of EPDIOL and Acc.Cl A mixture of Acc.Cl (6.68 g) and EPDIOL (43 g) was mixed with acetone (43 g) in a round bottom flask equipped with a stir bar and a heating mantle, and the mixture was stirred at 55° C. for 2 hours. The resulting mixture was orange in color, and the resulting product was found to have a peak at 1730 cm by IR. -1 The appearance of the ester peak was confirmed.

[0169] Example 6: Reaction of EPDIOL and GMA A mixture of GMA (10.49 g) and EPDIOL (15 g) was mixed in acetone (50 g) in a round bottom flask equipped with a stir bar and a heating mantle, and the mixture was stirred at 55° C. for 2 hours. The resulting mixture was clear, and the resulting product was characterized by the disappearance of the epoxide 844 absorption bond and the disappearance of the 1,100 cm -1 The formation of ether adsorption bonds was confirmed.

[0170] Example 7: Reaction of EPDIOL and phosphorus oxychloride A mixture of phosphorus oxychloride (11.30 g) and EPDIOL (15 g) was mixed with acetone (50 g) in a round bottom flask equipped with a stir bar and a heating mantle. Triethylamine was added as a catalyst to the mixture and stirred for 4 hours. The resulting mixture was dark brown in color.

[0171] EPDIOL-based polyurethane

[0172] Example 8: Reaction of EPDIOL with MBPI EPDIOL (0.5 moles) and DMAc were charged to a process reactor. The mixture was stirred and heated to a temperature of 65-70°C. MBPI (1.1 moles) was further charged to the reaction mixture and the 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 cooled to ambient temperature to form a polymer.

[0173] Example 9: Reaction of EPDIOL with PEG2, DMBA, HDI, and Hexanol EPDIOL (0.73 moles), PEG2 (0.32 moles), DMBA (0.95 moles) and acetone were charged to a process reactor. The mixture was stirred and heated to a temperature of 70-75°C. HDI (2.1 moles) was then charged to the reaction mixture and the reaction mixture was stirred for 5-15 minutes. DBTD (2.0% based on the weight of isocyanate) was added to the reaction mixture and stirred for 4 hours. Hexanol (0.2 moles) was added and stirred for 1.0 hour. Triethylamine was added to neutralize the DMBA and the contents were drained and cooled to ambient temperature to polymerize.

[0174] Example 10: Reaction of EPDIOL with MDEA, PEG2, HDI, and Hexanol EPDIOL (0.73 moles), PEG2 (0.32 moles), methyldiethanolamine (0.95 moles) and acetone were charged to a process reactor. The mixture was stirred and heated to a temperature of 70-75°C. HDI (2.1 moles) was then charged to the reaction mixture and the reaction mixture was stirred for 5 minutes. DBTD (2.0% based on the weight of isocyanate) was added to the reaction mixture and stirred for 5 hours. Hexanol (0.2 moles) was added and stirred for 1.0 hour. Acetic acid was added and the contents were drained and cooled to ambient temperature to polymerize.

[0175] Example 11: The reaction of Example 9 was repeated substituting DMPA for DMBA and IPDI for HDI.

[0176] Hydrophobically Modified Urethane-Ethoxylate (HEUR) Polymers A hydrophobically modified urethane-ethoxylate (HEUR) polymer was prepared by incorporating EPDIOL monomer into the backbone of the urethane ethoxylate polymer, "Structure-1" below. [ka]

[0177] Example 12(a): EPDIOL-IPDI-HEUR A hydrophobically modified urethane-ethoxylate (HEUR) polymer was prepared by the reaction mixture shown below as "Structure-2" having EPDIOL monomer and IPDI and described in the Examples below. [ka]

[0178] [Table 1]

[0179] [Table 2]

[0180] [Table 3] nEPDIOL means the target number of EPDIOL per chain.

[0181] Example 13: Solvent Process EPDIOL (12.7 g) was dissolved in 15 g of anhydrous acetone and charged to a process reactor along with 182.53 g of PEG2 and 175.0 g of anhydrous acetone. The reaction mixture was mixed and heated to 65-70°C. IPDI (27.46 g) was further charged in 15 g of anhydrous acetone at that temperature and mixed for 5-15 minutes. Next, 0.590 g of DBTDL (dibutyltin dilaurate) was charged in 10 g of acetone. 2.53 g of hexanol was further charged and the reaction was allowed to continue for 1.0 hour. At the end of the reaction, the product was discharged and either dried in a vacuum oven or subjected to a solvent water exchange.

[0182] Example 14: EPDIOL-HMDI HEUR Polymer [Table 4]

[0183] Example 14(c): Melt Process Polyethylene glycol (PEG1) (1,376.50 g) and EPDIOL (18.88 g) were charged to a process reactor. The reaction mixture was heated to 100-110°C and stirred under vacuum for 0.5-1.0 hours. The reaction mixture was cooled to 75-80°C and HMDI (89.30 g) was charged and mixed for 5-15 minutes. Dibutyltin dilaurate (1.92 g) was then charged and mixed at 100-110°C for 2.0-2.5 hours. After mixing was complete, hexanol (16.83 g) was charged and the reaction was continued for 1.0 hour. After the reaction was complete, the contents were discharged and cooled to ambient temperature to polymerize.

[0184] Example 14(d): Solvent Process EPDIOL (1.89 g) was dissolved in 15 g of anhydrous acetone and charged to a process reactor along with polyethylene glycol (PEG1) (137.65 g) and acetone (245 g). The reaction mixture was stirred and heated to 65-70°C. At that temperature, a mixture of (8.93 g) HMDI in (15 g) acetone was charged and mixed for 5-15 minutes. Next, (0.20 g) dibutyltin dilaurate was charged in (15 g) acetone and mixed for 5 hours, then hexanol (1.68 g) was charged in (15 g) acetone and the reaction was continued for 1.0 hour. The product was discharged and either dried in a vacuum oven or subjected to a solvent water exchange.

[0185] Example 15: EPDIOL-HDI-HEUR Polymer The EPDIOL-HDI-HEUR polymer of structure-3 was prepared according to the following structure of EPDIOL. [ka]

[0186] [Table 5]

[0187] [Table 6]

[0188] [Table 7]

[0189] [Table 8]

[0190] Example 15(d): Solvent Process EPDIOL (12.69g) in 15g anhydrous acetone was charged to a process reactor along with 188.95g PEG2 and 175.0g acetone. The reaction mixture was mixed and heated to 65-70°C. A mixture of 21.05g HDI in 15g acetone was mixed at that temperature for 5-15 minutes. Next, 0.453g DBTDL in 10g acetone was charged to the reaction mixture. The reaction mixture was mixed for 5 hours. Then, 2.53g hexanol was added to the reaction mixture and the reaction was allowed to continue for 1.0 hour. At the end of the reaction, the product was discharged and either dried in a vacuum oven or subjected to a solvent water exchange.

[0191] Example 15(l): Melt Process EPDIOL (18.88 g) and polyethylene glycol (PEG) were charged into a process reactor. The reaction mixture was heated to 100-110°C and stirred under vacuum for 0.5-1.0 hours. The reaction mixture was cooled to 75-80°C and HMDI (89.30 g) was charged and mixed for 5-15 minutes. Dibutyltin dilaurate (1.92 g) was then charged and mixed at 100-110°C for 2.5 hours. After mixing was complete, hexanol (16.83 g) was charged and the reaction was continued for 1.0 hour. After the reaction was complete, the contents were discharged and cooled to ambient temperature to obtain the polymer.

[0192] Examples of EPDIOL-HEUR coating applications: Example 16: Preparation of base paint Semi-gloss base paint formulations without low shear thickener and without high shear thickener were prepared by mixing the grind formulations listed in Table 9A and the letdown formulations listed in Table 9B.

[0193] [Table 9A]

[0194] [Table 9B] Rhoplex VSR 1050: Acrylic emulsion from The Dow Chemical Company Optifilm Enhancer 400: A coalescing agent available from Eastman Chemical Company Polyphase 678: A mold inhibitor available from Troy

[0195] Example 17: Composition of EPDIOL-HEUR polymer [Table 10]

[0196] Example 18(a): Comparative Example 1 - Semi-Gloss Formulation In Comparative Example 17(a), Aquaflow XLS 530 was added as the low shear (LS) polymer and Acrysol RM2020 (C6 HMDI) was added as the high shear (HS) polymer along with water to the base paint formulation shown in Tables 9A and 9B. The dosages of LS polymer, HS polymer 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.

[0197] Example 19: Semi-gloss formulation In Comparative Example 17(b), Aquaflow XLS 530 was added as the low shear (LS) polymer and polymer solution Example 17(b) was added as the high shear (HS) polymer along with water to the base paint formulation shown in Tables 9A and 9B. The dosages of LS polymer, HS polymer 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.

[0198] Example 20: Semi-gloss formulation In Comparative Example 17(c), Aquaflow XLS 530 was added as the low shear (LS) polymer and polymer solution Example 17(c) was added as the high shear (HS) polymer along with water to the base paint formulation shown in Tables 9A and 9B. The dosages of LS polymer, HS polymer 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.

[0199] Example 21: Semi-gloss formulation In Comparative Example 17(d), Aquaflow XLS 530 was added as the low shear (LS) polymer and polymer solution Example 17(d) was added as the high shear (HS) polymer along with water to the base paint formulation shown in Tables 9A and 9B. The dosages of LS polymer, HS polymer 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.

[0200] Example 22: Semi-gloss formulation In Comparative Example 17(e), Aquaflow XLS 530 was added as the low shear (LS) polymer and polymer solution Example 17(e) was added as the high shear (HS) polymer along with water to the base paint formulation shown in Tables 9A and 9B. The dosages of LS polymer, HS polymer 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.

[0201] Example 23: Wet Paint Properties [Table 11]

[0202] Example 24: Dry film properties [Table 12]

[0203] Test Method Stormer viscosity was measured by a Stormer viscometer expressed in Krebs Units (KU) as per standard test method ASTM D562.

[0204] ICI viscosity was measured with an ICI cone and plate viscometer expressed in poise (P) as per standard test method ASTM D4287.

[0205] Brookfield viscosity is measured with a Brookfield viscometer using spindle 5 at 30 RPM.

[0206] Settlement resistance is measured with a Leneta chart based on standard ASTM D4400 using a mid-range bar to measure the wet film thickness (WFT) in mils above which settling occurs.

[0207] Smoothness is measured with a Leneta chart based on standard ASTM D4062, a scale of 0 to 10, with 0 being the worst and 10 being the best.

[0208] The gloss is measured at angles of 60° and 80° using a spectrophotometer.

[0209] 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 according to the present disclosure exhibit good settling / leveling balance and gloss properties.

[0210] Table 12 shows the dry film properties of the examples presented in this disclosure. The polymers presented in this disclosure show higher gloss and good settling / leveling balance.

[0211] 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, but rather, numerous variations and modifications will occur to those skilled in the art in light of this disclosure without departing from the scope and spirit of the invention.

Claims

1. A polymer obtained from a reaction mixture, the reaction mixture comprising: (i) at least one dihydroxylactam moiety, and (ii) at least one functional moiety having a hydroxyl-reactive functional group; having (i) and (ii) are each independently present in an amount from 0.01 mol % to 99.99 mol %, and each of (i) and (ii) is present in an amount other than 50 mol %, and the polymer is a polyurethane; In the polymer, the dihydroxylactam moiety has the following chemical structure: 【Chemistry 1】 It has the following structure: wherein "R" is independently selected from the group consisting of hydrogen, functionalized and non-functionalized alkyl groups, cycloalkyl groups, alkenyl groups, and aryl groups, any of the foregoing groups may be linear or branched, with or without heteroatoms; "functionalized" refers to a state in which a moiety has one or more functional groups introduced therein by one or more functionalization reactions selected from the group consisting of epoxidation, sulfonation, hydrolysis, amidation, esterification, hydroxylation, dihydroxylation, amination, ammonolysis, acylation, nitration, oxidation, dehydration, elimination, hydration, dehydrogenation, hydrogenation, acetalization, halogenation, dehydrohalogenation, Michael addition, aldol condensation, Cannizzaro reaction, Mannich reaction, Claisen condensation, Suzuki coupling; "A" is an alkylene or alkenylene group containing from 2 to 50 carbon atoms, and from 2 to 4 carbon atoms are between the following groups: 【Chemistry 2】 Base and 【Chemistry 3】 is present in a lactam ring between the "n" is an integer ranging from 1 to 6 and "m" is an integer ranging from 0 to 6; The functional moiety comprises an isocyanate. polymer.

2. 2. The polymer of claim 1, wherein the dihydroxylactam moiety is selected from the following group: 【Chemistry 4】 selected from the group consisting of wherein "n" is an integer in the range of 1 to 6.

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

4. 2. The polymer of claim 1, wherein the functional moiety is selected from the group consisting of hexamethylene diisocyanate, toluene diisocyanate (TDI), diphenylmethane diisocyanate (MDI), m-phenylene diisocyanate, p-phenylene diisocyanate, vitrylene diisocyanate, cyclohexane diisocyanate (CHDI), bis-(isocyanatomethyl)cyclohexane (H6XDI), dicyclohexylmethane diisocyanate (H12MDI), dimer acid diisocyanate (DDI), trimethylhexamethylene diisocyanate, lysine diisocyanate and its methyl ester, diisocyanate, ... Polymers including isophorone isocyanate, methylcyclohexane diisocyanate, 1,5-naphthalene diisocyanate, xylylene and xylene diisocyanate and methyl derivatives, polymethylene polyphenyl isocyanate, chlorophenylene-2,4-diisocyanate, polyphenylene diisocyanate, isophorone diisocyanate (IPDI), hydrogenated methylene diphenyl isocyanate (HMDI), tetramethylxylene diisocyanate (TMXDI), hexamethylene diisocyanate (HDI), or their corresponding dimers, trimers, or oligomers.

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

6. The polymer of claim 5, １ ~C １８ aliphatic / aromatic alcohols having a carbon chain length of C １ ~C １８ Alkoxylated alcohols having a carbon chain length of 100 to 200 carbon atoms, ethylene glycol, alcohol meth(acrylates), polyvinyl alcohol, polycarbonate polyols, polybutylene glycol, polyethylene glycol, polypropylene glycol, hydroxypolyesters, hydroxypolyethers, hydroxypolythioesters, hydroxypolyacetals, hydroxypolycarbonates, polyether polyols, polyester polyols, polycarbonate polyols, hydroxypolyesters, hydroxypolyethers, hydroxypolythioesters, hydroxypolyacetals, hydroxypolycarbonates, aliphatic and aromatic polyether polyols, caprolactone-based polyols, poly(ethylene glycol)-soy amine, poly(ethylene glycol)-castor oil, poly(ethylene glycol)-hydrogenated castor oil, poly(ethylene glycol)-lanolin, poly(ethylene glycol)-lanolin wax, poly(ethylene glycol)-polyvinylidene fluoride, poly(ethylene glycol)-poly(vinyl acetate), poly(ethylene glycol)- A polymer having one or more non-lactam moieties selected from the group consisting of polyoxymethylene, poly(ethylene glycol)-esters, and combinations thereof.

7. 10. The polymer of claim 1, wherein the polymer has an average molecular weight ranging from 3000 g / mole to 1,000,000 g / mole.

8. A polymer obtained from a reaction mixture, the reaction mixture comprising: (i) N-(2,3-dihydroxypropyl)-2-pyrrolidone and / or 1-[2-(2,3-dihydroxypropyloxy)ethyl]-2-pyrrolidone, and (ii) (a) isophorone diisocyanate, (b) polyethylene glycol, and optionally (c) octanol; having A polymer, wherein (i) and (ii) are each present in an amount other than 50 mole %, and the polymer is a polyurethane.

9. In the composition, (I) A polymer obtained from a reaction mixture, the reaction mixture comprising: (i) at least one dihydroxylactam moiety, and (ii) at least one functional moiety having a hydroxyl-reactive functional group; having (i) and (ii) are each independently present in an amount from 0.01 mol % to 99.99 mol % and the polymer is a polyurethane, or (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; and Equipped with The dihydroxylactam moiety has the following chemical structure: 【Chemistry 5】 It has the following structure: wherein "R" is independently selected from the group consisting of hydrogen, functionalized and non-functionalized alkyl groups, cycloalkyl groups, alkenyl groups, and aryl groups, any of the foregoing groups may be linear or branched, with or without heteroatoms; "functionalized" refers to a state in which a moiety has one or more functional groups introduced therein by one or more functionalization reactions selected from the group consisting of epoxidation, sulfonation, hydrolysis, amidation, esterification, hydroxylation, dihydroxylation, amination, ammonolysis, acylation, nitration, oxidation, dehydration, elimination, hydration, dehydrogenation, hydrogenation, acetalization, halogenation, dehydrohalogenation, Michael addition, aldol condensation, Cannizzaro reaction, Mannich reaction, Claisen condensation, Suzuki coupling; "A" is an alkylene or alkenylene group containing from 2 to 50 carbon atoms, and from 2 to 4 carbon atoms are between the following groups: 【Chemistry 6】 Base and 【Chemistry 7】 is present in a lactam ring between the "n" is an integer ranging from 1 to 6 and "m" is an integer ranging from 0 to 6; The functional moiety comprises an isocyanate. composition.

10. 10. The composition of claim 9, wherein the additive is useful in an application selected from the group consisting of adhesives, aerosols, agricultural agents, anti-resoiling agents, battery agents, beverages, biocides, biomaterials, cement and construction agents, cleaning agents, paints and coatings, rheology modifiers, conductive materials, cosmetics, dental agents, decorative pigments, detergents, dispersants, pharmaceuticals, electronics, encapsulation, foods, hair care agents, home-industrial fixtures, inks and coatings, interlaminates, lithography solutions, thin film additives, metal working fluids, oil field agents, paper sizing agents, polishing agents, personal care agents, pharmaceuticals, pigment additives, ointments, plastics, textiles, lubricants, printing, refractive index modifiers, sequestrants, stain repellents, static control agents, and wood care agents.

11. In the coating composition, I. A polymer obtained from a reaction mixture comprising: (i) N-(2,3-dihydroxypropyl)-2-pyrrolidone and / or 1-[2-(2,3-dihydroxypropyloxy)ethyl]-2-pyrrolidone; and (ii) (a) isophorone diisocyanate, (b) polyethylene glycol, and optionally (c) octanol; having (i) and (ii) each being present in an amount other than 50 mole %, and the polymer being a polyurethane; and II. One or more pharma- ceutically acceptable coating agents; 1. A coating composition comprising:

12. 12. The coating composition of claim 11, wherein the coating agent is selected from the group consisting of solvents / co-solvents, secondary rheology modifiers, thixotropes, binders, crosslinkers, pH modifiers, pigments / fillers, flow control agents, gloss control agents, coalescing agents, softening resins, surfactants, waxes, wetting agents, dispersants, plasticizers, antioxidants, UV radiation absorbers, biocides, extenders, colorants, adhesion promoters, defoamers / defoamers, drying agents, matting agents, and combinations thereof.

13. 1. A process for preparing a polymer, comprising the steps of: (A) having (i) at least one dihydroxylactam moiety, and (ii) at least one functional moiety having a hydroxyl-reactive functional group, wherein (i) and (ii) are each independently present in an amount from 0.01 mol % to 99.99 mol %, and the polymer is a polyurethane, or wherein each of (i) and (ii) is present in an amount other than 50 mol %, and the polymer is a polyurethane; (B) filling (A) with a solvent in a reaction vessel under an inert gas atmosphere; (C) stirring the reaction mixture of (B) and maintaining it at a temperature of 55-70° C. for 30 minutes; (D) charging (C) with an additional reactive moiety; (E) catalytically polymerizing (D) for 3 to 5 hours; and (F) recovering the desired polymer from (E); Equipped with The dihydroxylactam moiety has the following chemical structure: 【Chemistry 8】 It has the following structure: wherein "R" is independently selected from the group consisting of hydrogen, functionalized and non-functionalized alkyl groups, cycloalkyl groups, alkenyl groups, and aryl groups, any of the foregoing groups may be linear or branched, with or without heteroatoms; "functionalized" refers to a state in which a moiety has one or more functional groups introduced therein by one or more functionalization reactions selected from the group consisting of epoxidation, sulfonation, hydrolysis, amidation, esterification, hydroxylation, dihydroxylation, amination, ammonolysis, acylation, nitration, oxidation, dehydration, elimination, hydration, dehydrogenation, hydrogenation, acetalization, halogenation, dehydrohalogenation, Michael addition, aldol condensation, Cannizzaro reaction, Mannich reaction, Claisen condensation, Suzuki coupling; "A" is an alkylene or alkenylene group containing from 2 to 50 carbon atoms, and from 2 to 4 carbon atoms are between the following groups: 【Chemistry 9】 Base and 【Chemistry 10】 is present in a lactam ring between the "n" is an integer ranging from 1 to 6 and "m" is an integer ranging from 0 to 6; The functional moiety comprises an isocyanate. process.

14. A process for preparing a polymer, said polymer comprising: (A) having (i) at least one dihydroxylactam moiety, and (ii) at least one functional moiety having a hydroxyl-reactive functional group, wherein (i) and (ii) are each independently present in an amount from 0.01 mol % to 99.99 mol %, and the polymer is a polyurethane, or wherein each of (i) and (ii) is present in an amount other than 50 mol %, and the polymer is a polyurethane; (B) filling (A) into a reaction vessel under an inert gas atmosphere; (C) stirring the reaction mixture of (B) and maintaining it at a temperature of 65-80° C. for 30 minutes; (D) charging (C) with an additional reactive moiety; (E) polymerizing (D) with a catalyst; (F) raising the temperature of (E) to 90-110° C. and maintaining this temperature for 2-3 hours; and (G) recovering the desired polymer from (F); Equipped with The dihydroxylactam moiety has the following chemical structure: 【Chemistry 11】 It has the following structure: wherein "R" is independently selected from the group consisting of hydrogen, functionalized and non-functionalized alkyl groups, cycloalkyl groups, alkenyl groups, and aryl groups, any of the foregoing groups may be linear or branched, with or without heteroatoms; "functionalized" refers to a state in which a moiety has one or more functional groups introduced therein by one or more functionalization reactions selected from the group consisting of epoxidation, sulfonation, hydrolysis, amidation, esterification, hydroxylation, dihydroxylation, amination, ammonolysis, acylation, nitration, oxidation, dehydration, elimination, hydration, dehydrogenation, hydrogenation, acetalization, halogenation, dehydrohalogenation, Michael addition, aldol condensation, Cannizzaro reaction, Mannich reaction, Claisen condensation, Suzuki coupling; "A" is an alkylene or alkenylene group containing from 2 to 50 carbon atoms, and from 2 to 4 carbon atoms are between the following groups: 【Chemistry 12】 Base and 【Chemistry 13】 is present in a lactam ring between the "n" is an integer ranging from 1 to 6 and "m" is an integer ranging from 0 to 6; The functional moiety comprises an isocyanate. process.

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