EP3914635A1

EP3914635A1 - Dihydroxy lactam based polymers, compositions and applications thereof

Info

Publication number: EP3914635A1
Application number: EP20745778.9A
Authority: EP
Inventors: Bilal S. Marie; Michael A. Tallon; Osama M. Musa
Original assignee: ISP Investments LLC
Current assignee: ISP Investments LLC
Priority date: 2020-01-23
Filing date: 2020-01-23
Publication date: 2021-12-01
Also published as: CN113631632A; CN113631632A8; EP3914635A4; JP2022518806A; WO2020154471A1; JP7671692B2

Abstract

A lactam-functionalized polymer is disclosed. The dihydroxy lactam based polymer includes polyesters, polycarbonates, polyethers, poly (ester ethers), poly (ester amides), polyimides, polyamides, poly acrylates and poly (ester imides), and polyurethanes. The applications of the dihydroxy lactam based polymers are also disclosed.

Description

DIHYDROXY LACTAM BASED POLYMERS, COMPOSITIONS

AND APPLICATIONS THEREOF

FIELD OF THE IN VENTION

10001] The present applicatio relates to dihydroxy lactam based polymers, compositions and applications thereof

BACKGROUND OF THE INVENTION

}QQQ2| N-vinyi lactam based polymers are those polymers having a lactam group, such as pyrroiidone or caprolactam, where tSie lactam nitrogen is directly bonded to the polymer backbone. These polymers, which include poly(N~\iny!~2-pyrrolidone), poly(N~vmyi~s- caprolactam), and poly(N-vinyl-2-pyrrolidone-co-N-viflyi acetate), are available in a wide range of molecular weight, which allows them to find use in many application arts, e.g,, as film formers, protective colloids, suspending agents, and many other uses. A description of these applications and properties is provided in the technical brochure“PVP Polyvinylpyrrolidone Polymers,” published by International Specialty Products, which is incorporated in its entirety by reference. »3] The success of N~ vinyl lactam polymers is attributed in part to the chemical structure of the lactam group. With its lone pair of electrons, the lactam nitrogen can form hydrogen bonds with compounds containing — OH and — NH groups. Such interactions can be manifested in a variety of properties, including adhesion (e.g., glue sticks, hair styling, tablet binder), crystallization inhibitor (e.g., gas hydrates, sucrose solutions), and complexation agent (e.g., dyes, active ingredients).

1001)41 In addition to the molecular weight, the number of carbon atoms in the lactam ring can be varied. Commonly known lactams include those from three carbon atoms/one nitrogen atom in the ring (propiolactam) up to six carbon atoms/one nitrogen atom in the ring (heptanolactam). I ncreasing the number o f carbon atoms in the ring alters the molecule’s water hydrophilicity/hydrophobicity balance. Although both poly(N~vinyl~2-p>Troltdone) andpoly(N-viuyl-£-caprolaeiam) are water soluble, the former is more hydrophilic, absorbing more water in humid environments than the latter. |QQ05] However, the available ranges in lactam ring size and polymer mo ecular weight are insufficient to design new monomers and polymers with truly ne functionality. For example, because the nitrogen atom of N-vinyl lactams is directly attached to the polymer backbone without a spacer group, there are limited options to modulate the hydrephilicity/ hydrophobicity balance of the molecule, or to alter a relatively high glass transition temperature [e.g., about 180°C for poly(N-vmyl-2 -pyrrol tdone)]. A new approach is needed that alters the structure of the N-vinyl lactam structure to facilitate new properties and end user applications. jOeObj To attain different properties current technology relies on copolymerizing other monomer units together with the N-vinyl lactam unit. Many such non-homopoly ers are known, and include those formed with N-vinyl acetate, styrene, dimethylaminoetliylmethacrylate, dimethylaminopropylmethacryiamide, acrylic acid, and lauryl methacrylate. A number of properties can be altered through these copolymerization, including hydrophobieiiy/hydrophiiiciiy, film formation, flexibility, foaming ability, humidity response, viscosity, gloss, and tack. While copolymerization produce valuable products, they are, in essence, pursued when the homppolymer cannot provide the desired properties. Desired are new lactam-based monomers and polymers thereof that offer expanded functionality

10007} In addition to functionality limitations, N-vinyl lactam based polymers require production methods and analytical testing to ensure sufficiently low residual monomer. Needed are next-generation lactam-based compounds that provide new properties and also are free of N-vinyl lactam monomer. jooes] There is a related family of compounds, also based on N-aikyl lactams that help extend the lactam moiety, in which an alkyl group is covalently bonded to the lactam nitrogen. Various N-alky l lactams are known, and include bu t not limited to N~mefhy1_:~2~pym>li ohe N- ethyl-2-pyrrohdone, N-hydroxyethyl-2-pytroMone, N-eyclohexyl-2-pyrroiidone, N-octyl-2- pyrrolidone, and N~dodecyl-2-pyrrolidone, all of which are offered for commercial sale by Ashland LLC (Bridgewater, NJ). Also known is N~hydroxyniethyl~2~eaproiactam (Benson, 1948). These non-pol eric chemicals find application as solvents, surface tension reducers, ari low-foaming surface wetting agen ts.

The prior art teaches several modified N-vinyl lactams via N-alkyl lactam . Thes documents include: U.S, Pat. Nos. 2,882,262· 4,008.247; 4,189,601; 4,190,582; 4,191 ,833; 4,191 ,834; 4,439,616; 4,609,706; 5,209,347; 5,252,689; 5,466,770; 6,369,163; 6,630,599; and OS patent applications: 2007/123,673; and foreign patents EP383,918; EPS50,744; and foreign patent applications: WOO 1 /12243; WO02/42383: WOtB/096568; W02007/051738; WO 2008/098885; WO 2008/098887; WO 201 1/022457; WO 201 1/085280; and WO 2011/022457. Many of these publications describe various esters of N-hydrox alkyllactaras, such as N-hydroxyethylpyrrolidone.

|bb 10] 1 -(2,3- dihydroxypropyl)pyrrolidin~2~one based lipids are described in WO

2011/056682. fee 11] Also, linear oligo and polyurethanes with pynrolidinone side rings are described by Kim et al (Uzbek Chemical Journal, Volume 17, lssue2, Pages 48-50, 1973).

SUMMARY OF THE INVENTION f00l2j One objective of the present application relates to a polymer obtained from a reaction mixture comprising: (i) at least one dihydroxy lactam moiety; and (ii) at least one functional moiety having a hydroxyl-reactive functional group; wherein (i) and (ii) are independently present in amounts of about 0 01 ¾ble% to about 99.99 moles% an the polymer is selected from the group consisting of polyester, polycarbonate, polyether, poly (ester ether), poly (ester amide), poly imide polyamide, poly acry lates and poly (ester i ide); or wherein each (i) and (ii) is present in amounts of other than 50 mo1e% and the polymer is a polyurethane

(0013) One of foe objectives of the present application relates to a polymer obtained from a reaction mixture comprising: (i) at least one dihydroxy lactam moiety or a modified dihydroxy lactam moiety with a reactive functional group; the modified dihydroxy lactam moiety can be constructed from esters, epoxies, ethers, urethanes, acrylates, anhydrides and combinations thereof, as additional functional groups attached te the dthydroxy lactam moiety and (ii) at least one functional moiety having a hydroxyl-reactive or a modified hydroxyl reactive functional group; wherein (i) and (ii) are independently present in amounts of about O.Oi mole% to about 99.99 moies% and the polymer is selected from a group consisting of polyester, polycarbonate, polyether, poly (ester ether), pol (ester amide), pol imide, polyamide, poly acrylates, poly (ester imide), and polyurethanes.

(0014] Another objective of the present application relates to a polymer obtained from areaction ixture comprising: (i) a dihydroxy lactam moiety selected from the group consisting of

(0015) wherein n is an integer ranging from 1 to 6; and (ii) at least one functional moiety having a hydroxyl-reactive functional group, wherein (i) and (ii) are independently present in amounts of about 0.01 mole% to about 99.99 moies% and the polymer is selected from a group consisting of polyester, polycarbonate, polyether, poly (ester ether) poly (ester amide), poly imide, polyamide, poly acrylates and poly (ester imide); or wherein each (i) and (ii) is present in amounts of other than 50 mole% and the polymer is a polyurethane. jt)t)16] One more objective of the present application relates lo a polymer obtained from a reaction mixture comprising: (!) N~(2,3-diltydroxypropyl)~2 pyrrolidone and/or i-[2-(2,3- dihydroxypropyl0xy)eihyi|-2-pyrrelidone, and (ii) poly(D, L-iacti e); wherein (i) and (ii) independently present in amount of about 0.01 moie% to about 99.99 moles% and the polymer is a polyester. 0017] Another objective of the present application relates to a polymer obtained fro a reaction mixture comprising: (i) -(2,3-dihydroxypropyi)-2-pyrrolidone and/or l-[2-(2,3~ dihydroxyi>fopyloxy)e iyi{~2-p>iTolidote, and (ii) diphenyl carbonate; wherein (ij and (il) are independently present in amounts of about 0.01 mole% to about 99.99 rool.es% and the polymer is a polycarbonate.

}0Q18| Yet another objective of the present application relates to a polymer obtained from a reaction mixture comprising: (i) N-(2f5-dihydroxypropyl)-2-pyrrolidone and/or l-[2-(2,3- dihydroxypropyioxy)ethyij-2-py.r.rolido.ne, (Ii) dibromo ethane, (hi) glycidyl ether; wherein (i), (ii) and (iii) are independently present in amounts of about 0.01 mo!e% to about 99.99 moies% and the polymer is a polyether.

(0019} Still another objective of the present application relates toa polymer obtained from a reaction mixture comprising: (i) N-(2 3~dihydroxypr<^yI -2-pyrroBdone and/or 1 ~ j 2-(2 ,3- dibydiOxypropyloxy)ethy!}-2-pyrroiidone, and (it) 1 ,4~dibromobutane and reacting thr product of (i) and (ii) with adipoyl chloride or adipic acid; wherein (i), (ii) and (iii) are independently present in amounts of about 0.01 mo!e% to about 99.99 moles% and the polymer is a polyester ether.

(0020] A different objective of the present application relates to a polymer obtained from a reaction mixture comprising: (i) N-(2,3-dihydroxypropyl)-2-pynolidcaie and/or l-j2-(2,3- dihy4roxypropyloxy)ethy! 1-2-pyTTolidone, and (ii) a-amino adds under p-to!uene sulfonic add; wherein the product of (i) and (ii) is reacted with (in) bis(p-niirophe:nyI succinate) and (i), (ii) and (iii) arc independently present in the amounts of about 0.01 mole% to about 99.99 moles% and the polymer is a polyester amide

[00 1) Another objective of the present application relates to a polymer obtained from a reaction mixture comprising: (i) N-<2,3-dihydroxypropyl)-2-pyrrofidone and/or l-[2-(2,3- dihydroxypropyioxy)ethyi]-2~pym lidone, and (ii)p-l¾oromtrohenzene ; wherein the product of (i) and (ii) is further hydrogenated to make the diamine (iii) and is reacted with (iv) pyromelktic dianhydride and (i), (ii) and (iv) are independently present in amounts of about 0.01 moie% to about 99.99 moles% and the polymer is a polyimide.

(0022} One more objective of the present application relates to a polymer obtained from a reaction mixture comprising: (i) N-(2,3~dihydroxypropyl)-2-pyiTolidone and/or l-j2-(2,3~ d i h y dro xypropy i ox y )e th y 1 i - 2 - py rrol i do ne , and (ii) p-fhioronitrobenzene ; wherein the product of (i) and (ii) is further hydrogenated to make the diamine (iii) and is reacted with (iv) adipoyl chloride or adipic acid, and (i), (ii) and (iv) are independeatiy present in amounts of about 0 01 fflole% to about 99.99 moles% and the polymer is a poly amide

10023] Yet another objective of the present application relates to a polymer obtained fro a reaction mixture comprising: (i) N-<2,3-dihydroxypropyi)-2-pytToiidone and/or l-[2-(2,3- dihydroxypropyioxy)ethyi|-2-pyriOlidone, and (ii) methaeryloyl ch!oride; wherein the product of (i) and (ii) is reacted with (iii) methyl methacrylate and (i), (it) and (iii) are independently present in amounts of about 0 01 mole% to about 99.99 moles% and the polymer is a poly acrylate. f0024) Still another objective of the present application relates to a polymer obtained from a reaction mixture comprising: (i) N-(2,3-dikydrdxypropy1)~2~py dMone and/or 1 ~) 2-(2 ,3- dihydiOxypropy!oxy)ethy!)-2-pyrrolidone, and (ii) p-fiuoronitiipheayl; wherein the product of (i) and (ii) is further hydrogenated to make the diamine (iii) and is reacte with (iv) N-(4-ehloro carbonyl phenyl) irimeSMmkle acid chloride and (i), (ii) and (iv) are independently present in amounts of about 0.01 moie% to about 99 99 mo!es% and the polymer is a polyester imkle.

[ 25] Another objective of the present application relates to a polymer obtained from a reaction ixture comprising: (i) N-(2,3-dihydroxypropyl)-2-pynolidcaie and/or i-[2-{2,3- dihydroxypropyloxy)ethy1 j-2-;pyrrolidone, and (ii) a) isophorone diisocyanate, b) polyethylene glycol, and optionally c) oeianol; wherei each (i) and (si) is present in amounts of other than 50 mole% and the polymer is a polyurethane.

|0026| One more objective of the present application relates to a composi ion comprising: (I) a polymer obtained from a reaction mixture comprising: (i) at least one dihydroxy lactam moiety, and (ii) at least one functional moiety having a hydroxyl-reactive functional group, wherein (i) and (ii) are independently present in amounts of about 0.01 mole% to about 99.99 moles% and the polymer is selected from a group consisting of polyester, polycarbonate,polyeilier, poly (ester ether), poly (ester amide), poly hnide, polyamide, poly acrylates and poly (ester imide); or wherein each (i) and (ii) is present in amounts of other than 50 mole% and the polymer is a polyurethane, and (if) one or more additives.

|002?| Another objective of the present application relates to a personal care composition comprising: (1) a polymer obtained from a reaction mixture comprising; (i) at least one dihydroxy lactam moie y, and (ii) at least one functional moiety having a hydroxyl-reactive functional group; wherein (i) and (ii) are independently present in amount of about 0.01 mole% to about 99.99 moles% and the polymer is selected from a group consisting of polyester, polycarbonate, polyether, poiy (ester ether), pol (ester amide), poly imide, polyamide, poly acrylates and poly (ester imide); or wherein each (i) and (ii) is presen t in amoun ts of other than 50 moie% and the polymer is a polyurethane, and (ii) one or more cosmetically acceptable additives.

(0028] Another objective of the present application relates to a coating composition comprising: (I) a polymer obtained from a reaction mixture comprising: (i) at least one dihydroxy lactam moiety, and (ii) at least one functional moiety having a hydrox l-reactive functional group; wherein (i) and (ii) are independently present in amount of about 0.01 mole% to about 99.99 mo!es% and the polymer is selected from a group consisting of polyester, polycarbonate, polyether, poly (ester ether), poly (ester amide), poly imide, polyamide, poly acrylates and poly (ester imide); or wherein each (i) and (ii) is present in amounts of other than 50 moie% and the polymer is a polyurethane, and (11) one or more coating additives.

(0029] Another objective of the present application relates to a pharmaceutical composition comprising: (!) a polymer obtained from a reaction mixture comprising (i) N~(2,3- dihydroxypropyi)-2-pyrrolidone and/or l-f2-i2,3-dihydroxypropyloxy}ethy!]-2-pyrrolidone; and (ii) poly(D,L-lactide); wherein (i) and (ii) are independently present in amount of about 0.01 mole% to about 99.99 moles% and the polymer Is a polyester, and (II) one or more pharmaceutically acceptable additi ves.

(0630] One more objective of the present application relates to a process of preparin a polymer comprising; (A) (i) at least one chhydfoxy lactam moiety, and (ii) at least one functional moiety having a hydroxyl-reactive functional group; wherein (i) an (ii) are independentl present in amount of about 0.01 mole‘% to about 99.99 oles% and the polymer is selected from the gro up consis ting of polyester. polycarbonate, polyeiher, poly (ester ether), poly (ester amide), poly imide, polyamide, poly acrylates and poly (ester imide); or wherein each (i) and (ii) is present in amounts of other than 50 mole% and the polymer is a polyurethane; (8) charging (A) into a reaction container under inert gas atmosphere with solvent; (C) stirring the reaction mixture of (B) and maintaining temperature af S5-7CFC for about 30 minutes; (D) charging an additional reactive moiety to (C); (B) polymerizing (D) with catalyst for 3-5 hours; and (F) retrieving desired polymer from (E). 10031} Still another objective of the present application relates a process of preparing a polymer comprising; (A) ii) at least one dihydroxy lactam moiety, and (ii) at least one functional moiety having a hydroxyl -reactive functional group, wherein f t) and (ii) are independently present in amounts of about 0.01 mole% to about 99 99 moles% and the polymer is selected fro a group consisting of polyester, polycarbonate, polyether, poly (ester ether), poly (ester amide), poly imide, polyamide, poly acrylates and poly (ester imide); or wherein each (i) and (ii) is present in amounts of other than 50 raofo% and the polymer is a polyurethane; (B) charging (A) into a reaction container raider inert gas atmosphere; (C) stirring foe reaction mixture of (B) and maintaining temperature at 65 FC for about 30 minutes; (D) charging an additional reactive moiety to (C); (E) polymerizing (D) with catalyst; (F) increasing temperatu re of (E) to 90° - 3 50¹C and maintaining the temperature for about 2-3 hours; and (G) retrieving desired polymer from (F).

DETAILED DESCRIPTION OF THE INVENTIO

|Q032} Before explaining at least one embodiment of the present disclosure in detail, it is to be understood that the present disclosure is not limited in its application to the details of construction and the arrangement of foe components or steps or methodologies set forth in the following description or illustrated in the drawings. The present disclosure is capable of other embodiments or of being practiced or earned out in various ways. Also, it is to be understood that the phraseology and terminology employed herein is for the purpose of description and should not be regarded as limiting.

I&Q33] Unless otherwise defined herein, technical terms used in connection with the present disclosure shall have the meanings that are commonly understood by those of ordinary skill in the art. Further, unless otherwise required by context, singular terms shall include pluralities and plural terms shall include the singular.

S |QQ34} All patents, published patent applications, and non-patent publications mentioned in the specificationare indicative of the level of skill of those skilled in the art to whichthe present disclosure pertains. Ail patents, published patent applications, and non-patent publications referenced in any portion of this application are herein expressly incorporated by reference in their entirety to the same extent as if each Individual patent or publication was specifically and individually indicated to be incorporate by reference.

|0035| All of the articles and/or methods disclosed herein can be made and execute without undue experimentation in light of the present disclosure. While the articles and methods of the present disclosure have been described in terms of preferred embodiments, it will be apparent to those of ordinary' skill in the art that variations can be applied to the articles and/or methods and in the steps or in the sequence of steps of the methodf s) describe herein 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.

10036} As utilized in accordance with the present disclosure, the following ter s, unless otherwise indicated, shall be understood to have the following meanings. f0037| The use of the wor “a” or“an” when used in conjunction with the term“comprising” can mean“one,” but it is also consistent with the meaning of“one or more,”“at least one,” and “one or more than one.” The use of the term“or” is used to mean“and/or” unless explicitly indicate to refer to alternatives only if the alternatives are mutually exclusive, although the disclosure supports a definition that refers to only alternatives and“and/or.” Throughout thisapplication, the term“about” is used to indicate that a value includes the inherent variation of error for the quantifying device, the method(s) being employe to determine the value, or the variation that exists among the study subjects. For example, but not by way of limitation, when the term“about” is utilized, the designated value can vary by plus or minus twelve percent, or eleven percent, or ten percent, or nine percent, or eight percent, or seven percent, or six percent, or five percent, or four percent, or three percent or two percent, or one percent. The use of the term“at least one” will be understood to include one as well as any quantity 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 extend up to 100 or 1000 or more depending on the ter to which it. is atached. In addition, the quantities of 100/1000 are not to he considered limiting as lower or higher limits can also produce satisfactory results. In addition the use of the term“at least one of X, Y , and Z” will 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 number terminology (i.e.,“first”“second”,“third”,“fourth", etc.) is solely for the purposes of differentiating between two or mor items and, unless otherwise stated, is not meant to imply any sequence or order or importance to one item over another or any order of addition

|QQ38} References herein to "one embodiment," or "one aspect" or "one version" or“one objective" or "another embodiment," or " another aspect" or " another version" or“another objective" of the invention can include one or more of such embodiment, aspect, version or objecti ve, unless the context clearly dictates otherwise.

|0039j The term“at least one" refers to one as well as any quantity 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 extend u to 100 or 1000 or more depending on the term to which it is attached.

{0040} All percentages, parts, proportions, and ratios as used herei are b weight of the total composition, unless otherwise specified. All such weights as they pertain to listed ingredients are based on the active level and therefore do not include solvents or by-products that can be included in commercially available materials, unless otherwise specified, 0041} All references to singular characteristics or limitations of the presen t invention shall include the corresponding plural characteristics or limitations, and vice-verm, unless otherwise specified or clearly implied to the contrary by the context in which the reference is made. Q042| Numerical ranges as use herein are intended to include every number and subset of numbers contained within that range, whether specifically disclosed or not. Further, these numerical ranges should he construed as providing support for a claim directed to any number or subset of numbers in that range.

(0043J As use herein, the words“comprising" (and any form of comprising, such as “comprise" and“comprises"),“having" (and any form of having, such as“h ave" and“has"), “including" (and any form of including, such as“includes” and“include") or“containing” (and any form of con taining, such as“contains" and“contain”) are inclusive or open-ended and do not exclude additional, unrecited elements or method steps. The terms“or combinations thereof ⁵ and“and/or combinations thereof’ as used herein refer to ail permutations and combinations of the listed items preceding the term. For example,“A, B, C, or combinations thereof⁵ is intended to include at least one of: A, B, C, AB_> AG, BC, or ABC and, if order is important in a particular context, also BA,€A,€8, C8A, BCA, A.CB, BAG, or CAB. Continuing with this example, expressly included are combinations that contain repeats of one or more items or terms, such as BB, AAA, AAB, BBC, AAABCCCC, CBBAAA, CABABB, and so forth. The skilled artisan will understand that typically there is no limit on the number of items or terms in any combination, unless otherwise apparent from the context,

10044} For purposes of the following detailed description, other than in any operating examples, or where otherwise indicated, numbers that express, for example, quantities of ingredients used in the specification and claims are to be understood as being modified in all instances by the term“about⁵⁵. The numerical parameters set forth in the specification and attached claims are approximations that can vary depending upon the desired properties to be obtained in carrying ou the invention. &Q45] The term“or combinations thereof⁵,“and combinations thereof⁵, and“combinations thereof⁵ as used herein refers to all permutations and combinations of the listed items preceding the term.

{0046] The term’'about" refers to a range of values + 10% of a specified value. For example, the phrase’’about 200” includes ± 10% of 200, or from ,180 to 220.

{0047] The term“monomer” refers to a small molecule that chemically bonds during polymerization to one or more monomers of the same or different kind; to form a polymer.

{0048] The term’’polymerization” or“polymerizing” refers to methods for chemically reacting monomer compounds to form polymer chains. The polymer chain can be alternating, b locked, or random. The type of polymerization method canbe selected from a wide variety ofmethods and include the following non-limiting examples: poly condensation, step growth polymerization, and free radical polymerization.

{0049] The term“macromolecule” refers to any large molecule, which includes polymers,

{0050] The term“polymer” refers to a large molecule comprisin one or more types of monomer residues (repeating units) connected by covalent chemical bonds. Non- limiting examples of polymers include homopolymers, and non-homopolymers such as copolymers, terpolymers, ietrapolymers an the higher analogues. (QQ51) The term“heleroatom” refers to oxygen, nitrogen, sulfur, silicon, phosphorous, or halogen. The heie.roatom(s) can be present as a part of one or more heteroatom-eontaining functional groups. Non-limiting examples of heteroatom-containing functional groups include ether, hydroxyl, epoxy, carbonyl, carboxamide, carboxylic ester, carboxylic acid, imine, imide, amine, sulfonic, sulfonamide, phosphonic, and silane groups. The heteroatomfs) can also be present as a part of a ring such as in heteroaryl and heteroary!ene groups.

{0052} The term“moiety” refers to a part or a functional group of a molecule.

{0053} The term "lactam" refers to groups having the structure:

wherein A is a functionalized or uniunetionalized aikylene or a!kenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between the group and the group; and R is selected from the group consisting of hydrogen, functionalized and unfnnctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the groups can be with or without heteroatoms.

{0054} The lactam-containing moiety can comprise a general lactam structure including b- lactani, y-lactam, d-Iaetam and e-lactam. In one non-limiting embodiment, the lactam-containing moiety can comprise a lactam structure including b-propiolactam, y- butyrolactam, d -va I ero lactam arid s-capfolactam. |QQ55] The term“alkyl” refers to a functionalized or i&nctiaualixed monovalent straight- chain, brandred-chaiu or cyclic C1-C60 group optionally having one or more heteroatoms. Particularly, an alkyl is a€ 1 ~C45 group and more particularly, a C 1€30 group. Particular, yet non-limiting examples of alkyl groups include methyl, ethyl, n-propy!, isopropyl, n-hutyl, isobutyl, tert-butyl, cyclobutyl, n-pentyl, isopentyl, cyclopenlyi, n~hexyl, cyclohexyl, n-heptyl, cyclyheptyl, methylcyclohexyl, n-octyl, 2-ethylhexyl, tert-octyl, iso-norbomyl, n-dodecyl, tert- dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, and n-eicosyl.

10056] The term "branched and unbranched alkyl groups" refers to alkyl groups, which can be straight chained or branched. Fo example, the alkyl groups have from 1 to about 60 carbon atoms, more particularly, from 1 to about 30 carbon atoms, and yet more particularly from 1 to about 6 carbon atoms. Branched groups include isopropyl, /erf-butyl, and the like. fOOSTj The term“alkylene” refers to a functionalized or unfunctionalized divalent straight- chain, branched-chain or cyclic Ci-Cw group optionally having one or more heteroatoms. Particularly, an alkylene is a C1-C45 group and more particularly, a Ct-Cx> group. In particular, yet non-limiting examples of alky lene groups include -CH2-. -€½-€½-, -CH(CH; -CH2-, -€H -€Hίa¾)-~, “C{CHS>2~€H2~, -C«b-C(CHi) -, ---CHfCm)---CM(CM3>--, -C{Cl-h)2- C(CH3)2~, -CfMft-Cft , ~€H(€H3)-CH3~CH , -€H2-€H(CH3>~€H:3~, -Cft-CHj- CH(C¾ ~CH2- H^'2~€H^'2-CH>~, -CH2~C½~CH2-CH-i-CH2~ -CHs-CHz- Hz-CH^ CH2---CH2---, ·€HZ-·€HZ···€H2···€H2···€H2···€H2··€H2···, cyclopropylene, cyclobutyiene, cyclopentylene, cydohexylene, and the like.

|(H)58] The term’’aryl" refers to a functional group derived from an aromatic hydrocarbon. The aromatic hydrocarbon can be mononuclear or polynuclear. Examples of aryl group of the mononuclear type include phenyl, tqlyl, xytyl, mesityl, cunienyi, and the like Examples of and group of the polynuclear type include naphthyl, anthryl, phenanthryi, and the like. The aryl group can have at least one substituent selected from halogen, hydroxy, cyano, carboxy, carbamoyl, nitro, amino, anitnomelhy!, lower alkyl, lower a!koxy, mercapto, trichloroetbyl, or trifluoromethyl. Examples of such substituted aryl groups include 2-fluorophenyl, 3- nitrophenyl, 4-nitrophenyi, 4-metho. phenyi, 4-hydroxyphenyl, and fee like.

(0059] The term“cycloalkyl group” refers to a non-aromatic mono- or multicyclo ring system haying from about 3 to about 10 carbon atoms. The eyeloalkyl group can be partially unsaiurated. The eyeloalkyl group can also be substituted with m alkyl group substituent as defined herein. The cycloalkyl chain can contain an oxygen, sulfur, or substituted or ansiihstituted nitrogen atom, wherein the nitrogen substituent can be hydrogen, alkyl, substituted alkyl, aryl, or substituted aryl, thus providing a heterocyclo group. Representative monocydo cycloalky! rings include, but are not limited to, cyclopropyl, eyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and the like. Further, the cycloalkyl group can be substituted with a linking group, such as an alkyl group, alky!ene group, and the like, to form cydopropy tmethyl group, cyciobutyimethyl group, and the like. The cycloalkyl group can also be a ulticyclo cycloalkyl rings such as adamanty!, octahydroaaphthyl, decalin, camphor, camphane, and norad annuity!.

[0069] The term "functionalized” refers to the state of a moiety that has one or more functional groups introduced to it by way of one or more functionalization reactions known to a person having ordinary skill in the art. In particular, yet non-limiting examples of functionalization reactions include epoxidation, sulfonation, hydrolysis ami elation esterification, hydroxylation, dihymxylation, animation, ammonoiysis, acylation, nitration, oxidation, dehydration, elimination, hydration, dehydrogenation, hydrogenation, acetalizatlon, halogenatioo dehydrohaiogeuaiion, michael addition, aldol condensation, eanizzaro reaction, mannich reaction, ciasien condensation, suzuki coupling, and the like. Particularly, functionalization of a moiety replaces one or more hydrogens in the moiety with one or more non-hydrogen groups, for e.g , alkyl, alkoxyl, cycloalkyl, alkenyl, cycloalkeny!, alkynyl, and/or and groups. Particular, yet non-limiting examples of cycloalkyl groups include eyciopentane, cyclohexane, cycloheptane, an the like. Particular, yet non-limiting examples of alkoxy groups include methoxy, ethoxy, n-propoxy, isopropoxy, and the like. Particular, yet non- limiting examples of aryl groups include benzenes, naphthalenes (2 rings), anthracenes (3 rings), and the like.

[0061] The terms "pharmaceutically acceptable" and "cosmetically acceptable" refer to molecular entities and compositions that are generally regarded as safe. Particularly , as used herein, the term "pharmaceutically acceptable" and "cosmetically acceptable” refer to approved by a regulatory agency of the appropriate governmental agency or liste in the IIS. Pharmacopoeia or other generally recognized pharmacopoeia for use in animals, an more particularly in humans.

[0062] The term“pharmaceutically active ingredient" refers to any ingredient considered to have a therapeutic effect when delivered to a subject in need thereof and further being regulated by drug authorities Hke CDER, EMEA, AG etc. Pharmaceutically active ingredients can act systemicaliy upon oral consumption, or locally such as when present in the buccal cavity, on the skin, etc. They can also be delivered across the skin as in transdermal drug delivery systems.

|0063j All percentages, ratio, and proportions used herein are based on a weight basis unless other specified.

{0064] The present disclosure is directed to a polymer obtained from a reaction mixture comprising (i) at least one dihydroxy lactam moiety and (ii) at least one functional moiety having a hydroxyl-reactive functional group; wherein (i) and (ii) are independently present in amounts of about 0.01 mole% to about 99.99 moles% and the polymer is selected from the group consisting of polyester, polycarbonate, poly ether, pol (ester ether), poly (ester amide), poly imide, polyamide, pol acrylate and poly (ester imide); or wherein each (i) and (ii) is present in an amount of oilier than 50 moie% and the polymer is a polyurethane.

|QQ65] According to one of the embodiments, the dihydroxy lactam moiety has a structure:

wherein “R” is independently selected from the group consisting of hydrogen, and ft etionalirod and toinneiionalissd alkyl, cyeloalkyl, alkenyl, an aryl groups, wherein any of the aibfe mentioned groups can be with or without heteroatoms and linear Or branched;

“A” is an aikylene or alkenylene group comprising 2 to 50 carbon atoms; wherein 2 to 4 carbon atoms reside in the lactam ring betwee the

group and the group

“n” is an integer ranging from 1 to 55; and“m” is an integer ranging from 0 to 5.

jf>fJ66| More particularly, each A in the lactam ring between the

group and the

R

L ; group can be independently selected from the group consisting of

(propylene) _{^ an£}j (butylene)

|0qί>7] More particularly, each A in the lactam ring between the

group and the

R ; group can be independently

- - - - CH_jt—— CH₂ - _or ~ - CH_j - CH₂~ - -CH₂ - "CH₂ -

[QQ68] More particularly, each R can be independently selected from the group consisting of hydrogen, functionalize and unfuncrionalized slfcyi eyeloalky 1, alkenyl, and ar l groups containing 1-10 carbon atoms, wherein any of the groups can he with or without heieroatonis. More particularly, each R can contain 1-8 carbon atoms. Most particularly each R can contain I -6 carbon atoms. f0069] Non-limitin examples of the dihydroxy lactam moiety include

wherein u is a integer ranging from 3 to 6 and“m” is an integer ranging from 0 to 6.

|0070) According to one of the embodiments, the chhydroxy lactam moiety compound is selected from the group consisting of N-(2,3-dihydroxypropyl)-2-pynOlidone, I-[2-(2,3- dihydroxypropyloxy)etliyi]~2~pyrro!idone, and a combination thereof.

(0071 j According to yet another embodiment, the dihyciroxy lacta moiety compound is present in an amount from about 0.01% to about 99 99% by weight of the total reaction mixture, in another embodiment, other possible ranges of dihydroxy lactam moiety compound would include, but are not limited to, from about 0.1. «7. % to about 10 w?. Mwt. M; from about 10 wt. %wt. M to about 20 vi -7. Mwf. %; from about 20 wt f to about 30 wt 94; from about 30 wt: 94 to about 40 wt. %; from about 40 wt % to about 50 wi from about 50 wt. % to about 60 wt. %; from about 60 wL % to about 70 W % from about 70 w. % to about 80 wl. %; from about 80 wt. % to about 90 w % or from about 90 wi % to about 99.99 wl. %.

[0072] According to one of the embodiments the functional moiety having a hydroxyl- reactive functional group is selected from the group consisting of: (a) carbamates, (b) acyl halides, (c) suifonyl halides, (d) isothiocyanates, (e) cyanoacrylates, (t) isocyanates, (g) oxiranes (h) imines, (I) thiocarbonates, (J) thiols, (k) aldehydes, (!) aziridines, (m) acids and their anhydrides, (n) azides, (o) phosphorus halides with alcohols, (p) esters, (q) amines, (r) alky! halides, (s) dihalogenoraethanes and combinations thereof

[0073] According to another embodiment, the carbamate is selected from the group consisting of hydroxyethyl carbamate, hydroxypropyl carbamate, bydroxybutyl carbamate and combinations thereof.

[0074] According to one embodiment, the acyl halide compound is selected from the group consisting of aery!oyi chloride, succinyt chloride, methacryloyl chloride, crotonoyl chloride, benzoyl chloride, cinnamoyl chloride, hydrocin natnoyi chloride, acetyl chloride, 2- acetoxyacetyl chloride, diphenylacetyl chloride, 2 methoxybenzoyi chloride, 3,4,5 trimethoxy benzoyl chloride, 3,4 (methylenedioxy)benzoyl chloride, cyelopropanecarbonyl chloride, pentadecenoyl chloride, 2-cyclohexene- 1 -carbonyl chloride, 2-thiopheneacetyl chloride and combinations thereof.

[0075] According to another embodiment, the suifonyl halide compound is selected from the group consisting of methane suifonyl chloride, benzenesulfbnyl chloride and combinations thereof

[0Q76] According to another embodiment, the isothiocyanate compoun is selected from the group consisting of methyl isothiocyanate, ally! isoihiocyanate, aryl isothiocyanates and combinations thereof.

[0077] According to another embodiment, the cyanoacrylate compound is selected from the group consisting of ethyl cyanoacrylate, N-butyl-eyanoaerylate (NBCA), 2-oeyiyl- cyanoacrykte (2-OCA) and combinations thereof.

[0078] According to another embodiment, the isocyanate compound is selected from the group comprising of hexamethyiene diisocyanate, toluene di isocyanate (TDl), dipheoyhimilmoe diisocyanale (MDI), m~phenylene diisoeyanate, p-phenylene diisocyanate, biiolylene diisocyanale, cyclohexane diisocyanale (GHDI), bis (isocyanatomeihy1) cyclohexane (H6XDI), dicyclohexylraethane diisocyanate (H.12MDI), dimer acid diisocyanate (DDI), trimethyl hexameihy!ene diisocyanale, lysine diisocyanale and its methyl ester, isophorone diisocyanale, methyl cyclohexane diisocyanale, 1,5-napthalene diisocyanate, xyiylene and. xylene diisocyana e and methyl derivatives, polymethylene polyphenyl isocyanates, chlorophenylene-2,4-diisocyanate, polyphenylene diisocyanale, isophorone diisocyanale (1PDI), hydrogenated methylene diphenyl isocyanate (HMD!), tetramethy! xylene diisocyanate (TMXDI), hexamethylene diisocyanale (HD!), and their respective dimers, trimers and oligomers and combinations thereof.

|qq?9| According to another embodiment, the oxiratie compound is selected from the group consisting of ethylene oxide (EO), propylene oxide (PC), butylene oxide, 1-ociene oxide, cyclohexene oxide, styrene oxide, bisphenoi A diglycidy! ether, diglycidyl ether, epichlorohydrin, giycidic acid, allyl glycidyl ether ([(2-propenyioxy)methyl]-oxirane), giycidyl (meth)acrylate, vinylcyclohexene diepoxide, 3,4-epoxyeyclohexyhiiethyi 3,4- epoxycyclohexane carboxylate, 3,4-epoxy-6-methyIcyciohexyimethyl 3,4-epoxy-6- methylcyclohexane carboxylate, dipentene dioxide, 2-{3,4-epoxycyclohexyi-5,5-spiro-3,4- epoxy)cycldhexane meta-dioxane, and combinations thereof

|0089] According to another embodiment, the inline compound is selected from the group consisting of polyaldimines, hydroxyaldimmes, polyketimines, hydroxykeiimin.es, and combinations thereof.

|¾081| According to another embodiment, the thioearbon e compound is selected from the group consisting of bis-^J nylthiocarbonyloxymethyl) esters, bis- (isopropyltfaiocaibonyloxymethyl) esters, and combinations thereof

|QQ82] According to another embodiment, the thiol compound is selected from the group consisting of glutathione, 3-acetyl- thiol propionic acid, tliio anhydride, thio acid, andcombinations thereof

10083| According to another embodiment, the aldehyde compound is selected from the group consisting of acetaldehyde diethyl acetyl, propionaidehyde diethyl acetyl, di(acetaldehyde diethylacetal), cbloroacetaldehyde diethyl acetal, and combinations thereof [8884] According to another embodiment, toe aziridine compound is selected from the group consisting of 2 ,2-bishydroxymetfeylhntanol trisj i 3-( 1 -aziridmy f)propionate |, his-N~ aziridlnooiethane, and combinations thereof

[0085] According to another embodiment, the acid and their anhydride compound is selected from the group consisting of maleic acid, aleic anhydride, fnnmrie acid, citric acid, alkeny!succinic anhydrides, phthalic anhydride, terepMha!ic acid, succinic anhydride, tetrahydrophthalic anhydride, maleic anhydride copolymers, and combinations thereo

(8Q86] According to another embodiment, the azide compoun is selected from the group consisting of azide-functionalized DMA, azide-functionalized peptides, azide-iuneiionaiized proteins, azide- functionalized sugars, azide-functionalized metal azide-functionalized nanoparticles, azide-funetionalized antimicrobials, isodinm d^ -diazi ostiibene»·!,!- disulfonate, aromatic bisazide compound, calcium azide, 4,4-diphenyldisnlfonyi azide and p- toluenesulfonyl azide, and combinations thereof.

18887] According to another embodiment the phosphorus oxyhaMe compound is selected from the group consisting of phosphorus oxychloride, phosphorus oxybromide. and combinations thereof

(8888} According to another embodiment, the ester compound is selected from the group consisting of dimethyl itaconate, di-n-butyi itaeonate, vinyl hexanoate, glycohde, s~ eaproiactooe, v-caprolactone poiy{D,L-lactide), poly(B-lactide), poly (L~laciide) poly(f eaprolactone), poly (y-caprolaetone), polygiycolide, valerolactone, buiralactone, polyether- po lyes ter, poiy-anbydride-dioi -polyester, and combinations thereof.

[8889] According to another embodiment, the amine compound is selecte from the group consisting of amino alcohols, meihyiamine, ethylarnine, hexylamine, isopropykmine, isobutylamine, amylamiues cycio exylamme, octylamine, benzylanhne, dimethylamine, diethyia ine, dipropylannne, dibiitykmitie, diphenyiamine, dibenzylamine, ethy!methy!amine, N-methylaniiine, ethylenediamine, propylenediamine, butylenediamine, hexamethy ienediamine, cyctobexylenediamine, piperazine, toiuenediamine, isophoronediamine, N ,N-diniethykm!iiie_x N,N-dimethyl-l -naphthylamine, N, -dimethy1-p- toluidine, N,N-diefhylanilme, ,N-diaSlylaniline, i-phenyipiperidine, and 4- phenylmorpholine, amino-ethoxyktes, cocamine, soyamine and combinations thereof. [QQ90] According to another embodiment, the alkyl halide compound is selected from the group consisting of bromohe aiies bromododecane, bromohexadecane,. .1 bromooctadecane and combinations thereof.

[9991 j According to another embodiment, the dihalogenomethane compound is selected from the group consis ting of dib ro mome than e , dichloromethane and combinations thereof.

[9992] According to yet another embodiment, the functional moiety having a hydroxyl- reactive functional group is present in an amount from about 0.01 % to about 99.99% by weight of the total reaction mixture. In another embodiment, other possible ranges of functional moiety having a hydroxyl-reactive functional group would include, but are not limited to, from about 0.1 H7. ¾ to about 10 wt. % from about 10 wt % to about 20 wt. % from about 20 wt: to about 30 wt. M; from about 30 wr. H to about 40 wt. f&; from abou 40 wt. to about 50 wt: % from about 50 wt. % to about 60 wt. %; from about 60 wt. ¾ to about 70 wt %; from about 70 wt. % to about 80 wt. %; from about 80 wi. % to about 90 wf %; or from about 90 wt % to about 99.99 wt. '¾

[0993] The present disclosure is also directed to a polymer obtained from a reaction mixture comprising (i) 0,01 mole% to about 99,99 moIes% of at least one dihydroxy lactam moiety, and (ii) 0.01 raofe% to about 99.99 moles% of at least a .functional moiety having a hydroxy l- reactive functional group; wherein the polymer is selected from a group consisting of polyester, polycarbonate, polyether, poly (ester ether), poly (ester amide), poly imide, polyamide, poly acrylates and poly (ester imide); or wherein each (i) and (ii) is present in amounts of other than 50 nioie% and the polymer is a polyurethane. f 00941 Accordin to another embodiment, the reaction mixture further comprises one or more non-lactam moiety.

[0095] According to another embodiment, the non-lactam moiety is selected from selected from the group comprising of fr ctionalized/unfunctionalized compounds: aliphatic/ aromatic alcohols with a carbon chain length of Ci-Css , alkoxylated alcohols with a carbon chain length of Ci-Cis alcohol, ethylene glycols, alcohol meih(aerylate$}, polyvinyl alcohols, polycarbonatepolyols, polybutylene glycols, polyethylene glycol, polypropylene glycols, hydroxypolyesters, hydroxypolyethers, hydroxypolythloesters, hydroxypolyacetals, hydroxypolycarbonates, polyetherpolyols, polyeslerpolyo!s, polycarbonatepolyols, hydroxypolyesters, hydroxypolyethers, hydroxypolythioesters, hydroxypolyacetals. hydroxypolycarbonates, aliphatic and aromatic polyether polyols, capro!aetone-bssed polyols, polyCeihylene gtyeoD-soyamme, polyethylene glycol)- castor oil, polyfeihylene glycol)- hydrogenated castor oil, poly(ethylene gfyeol)~]anolm, poly(ethylene giycoJi-lanolin wax, poly(ethylene glycoO-poJyviny!idene fluoride, poiy(ethylene giycoli-poiyf vinyl acetate), polyethylene glycol)-polyoxymethylene, poly( ethylene glyco l)-e$ter, and combinations thereof

{0096} According to yet another embodiment, the non-lactam moiety compound is present in an amount from abou 0.01% to about 99.98% by weight of the total reaction mixture. In another embodiment, other possible ranges of non-lactam moiety would include, but are not limited to, from about 0.1 wt. % to about 10 wt. %; from about 10 wt. % to about 20 wt. %\ from about 20 wt. % to about 30 wt. %; from about 30 wt. % to about 40 w/. from about 40 wt to about 50 wt. %; fro about 50 vvf. % to about 60 wf. 94; from about 60 wt % to about 70 w7, %\ from about 70 wt. % to about 80 wt. %\ from about 80 wt. % to about 90 wt. %\ or from about 90 wL % to about 99.98 wt %.

{0097} Molecular weight of the dihydroxy lactam functional ed polymer is in the range of from about 3,000 g/mo! to about 1,000,000 g/mol. Other preferred molecular weight ranges would 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 about 400,000 g/mol to about 500,000 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 1000,000 g/mol.

{0098] The present disclosure is also directed to a polymer obtained from a reaction mixture comprising (i) N-(2,3_*dihydroxypropyl)-2-pyrrolidone and/or l-[2-(2,3- dihydroxypropyioxy)eihyi]~2-pynOlidone, and (Ii) poly(D, L-laetide); wherein (i) and (ii) are independently present in amounts of about 0.01 mole% to about 99.99 rao1e% and the polymer is a polyester.

|0Q99{ The present disclosure is further directed to a polymer obtained from a reaction mixture comprising (i) N-C2,3~dihydroxypropyl>2~pynrolidone and/or i-|2-(2,3- dihydroxypropylox )ethyl]-2-py >lidone, an (ii) a) isophorone diisoeyanaie, b) polyethylene glycol, and optionally c) ocianoi; wherein each (i) and (ii) is present in amounts of other than 50 mole% and the polymer is a polyurethane.

[00100] The type of polymerization method used to prepare the polymers of this invention include, but are not limited to, poly condensation, step growth polymerization and free radical polymerization. jOOlOi Non-limiting illustrative examples of structures of polymers of the invention, prepared as set out below, by reacting: (i) at least one dihydroxy lactam moiety, and (ii) at least one functional moiety having a hydroxyl-reactive functional group; wherein (i) and (ii) are independently present in amounts of about 0.01 mole% to about 99 99 mole$% and the polymer is selected from a group consisting of polyester, polycarbonate,, polyether, poly (ester ether), poly (ester amide), poly imide, polyamide, poly acrylates and poly (ester imide}; or wherein each (i) and (ii) is present in amounts of other than 50 mole% and the polymer is a polyurethane, include the following:

J00102 PDIOL- DIOL-Diisocyanale based polyurethanes:

pH

OCN-R-NCO

Di- isocyanate HO-ROH

VoH

Diols (Eg; PEG)

Ή _>

0^( j

-S 2 , 3 - D t by iiOx propy i >'2 '}¾ rr I ido»e

PDiOL- PEG- Diisocvisnate

wherein xd-y+x -100.

[00183] EPDIO - iOL-DiisGcyaiiaie based polyurethanes; HQ

(>CN~R~ NC(>

+ >~OH

Di -isocyanate + HO-R'OH— -

V Diois (Eg: PEG)

<

°V R

t '

i-[2-(2,3-dihydroxyprop k xy)ethyi]-2 pyrro!iii!>ne

EPDIOL- PEG- Diisaeyarmfc

wherein x+-y-tz^::::l 00.

100104] EPDIOL-DIOL-Diisocyante-Alcohol based polyurethanes;

wherein x÷y4 =l 00; and the alcohol can be hexanoi.

(00105] EPDIOL-DIOL-DMPA-Diisocyanate- Alcohol based polyurethanes :

, wherei x+y+x÷w=100 arid the alcohol can be ethanol

(00106) The present disclosure is also directed to a wide variety compositions comprising: (I) a polymer obtained from a reaction mixture comprising; (i) at least one dihydroxy lactam moiety, and (ii) at least one functional moiety having a hydroxyl-reactive functional group; wherein (1) and (ii) are independently present in amounts of about 0.01 mole% to about 99.99 moles% and the polymer is selected from a group consisting of polyester, polycarbonate, polyether, poly (ester ether), poly (ester amide), poly irnide, polyamide, poly acrylates and poly (ester imide); or wherein each (i) and (ii) is present in amounts of other than 50 mole% and the polymer is a polyurethane, and (II) one or more additive.

(00107) According to one embodiment, the additive is useful in an application selected from the group consisting of adhesives, aerosols, agricultural agents, anti-soil redeposition agents, batteries agents, beverages, biocides, biomaterial, cementing and construction agents, cleaning agents, paints & coating agents, rheology modifiers, conductive materials, cosmetic agents, denial agents, decorated pigments, detergents, dispersants, drugs, electronics, encapsulations, foods, hair care agents, household-industrial institutional agents, inks an coatings, interiaminate, lithographic solutions membrane additive agents, metal working fluids, oilfield agents, paper sizing agents, polish, personal care agents, pharmaceuticals, pigment additives, plasters, plastic, textile, lubricant, printing, refractive index modifiers, sequestrants, sod release agents, static control agents, and wood-care agents. |ddl08j The compounds, monomers, and polymers described herein can be used alone or in combination with other ingredieni(s) in various compositions and prodnci forms. Such compositions include, but are not limited to, adhesive, aerosol, agricultural compositions, antisoil redeposition compositions, batteries, beverage compositions, biocide compositions, biomaterial composition, cementing and construction composition, cleaning composition, paints & coating composition, rheology modifier composition, conductive material compositions, cosmetic compositions, dental compositions, decorative pigment compositions, detergent compositions, dispersant compositions, electronic application compositions, encapsulatio polymer composition, food composition, hair care composition, household- industrial institutional compositions, inks and coating compositions, interlaminate compositions, lithographic application compositions, membrane composition, metal working fluid composition, oilfield compositions, paper sizing agent compositions, polishing compositions, personal care compositions, pharmaceutical compositions, plaster compositions, plastic additive composition, textile composition, lubricant composition, printing compositions, refractive index modifier compositions, sequesirant compositions, soil release compositions, static control agents, and wood-care compositions.

[001 9{ The term“personal care composition” refers to composition intended for use on or in the human body. Non-limiting, but speci fic types of personal care compositions include hair care compositions (encompassing styling and non-styling compositions), sun care compositions (encompassing after-sun compositions), skin care compositions and oral care compositions.

(00110} The personal care compositions can be formulated in any of th product forms known to a person of ordinary skill in the art. Non-limiting product forms are described below.

[00111 } Product Forms:

[00112} Non-limiting hair care product forms include: shampoos, conditioners, aerosols, mousses, sprays, mists, gels, waxes, creams, lotions, glues, pomades, spri.tz.es, solutions, oils, liquids, solids, W/O emulsions, OZW emulsions, suspensions, multiple emulsions, mieroemulsions, microencapsulated products, sticks, balms, tonics, pastes, reeonstitutable products, nanoemulsions, solid lipid nanoparticles, liposomes, cubosomes, neosomes, putties, lacquers, serums, perms, volumizers, packs, flakes, 2-in~l shampoo/conditioner products, and 3-in- 1 shampoo/conditioner/styhiig products. [QQ113] The compositions according to the invention can also Cake the form of after-shampoo compositions, to he rinsed off or not, for permanents, straightening, waving, dyeing, or bleaching, or the form of rinse compositions to be applied before or after dyeing, bleaching, permanents, straightening, relaxing, waving or even between the two stages of a permanent or straightening process.

[QQ114] 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.

[QQ115} Non-limiting skin care product forms include: solutions, oils, lotions, creams, ointments, liquids, gels, solids, WfO emulsions, QtW emulsions, milks, suspensions, microemulsions, dispersions, microencapsulated products, sticks, balms, tonics, pastes, mists, reconstitntable products, peels, soaps, aerosols, mousses, waxes, glues, pomades, spriizes, putties, lacquers, serums, perms, powders, pencils, flakes, blush, highlighters, btonzers, concealers, and 2-way cake products.

|00116 The compositions of the invention can also take the form of skin-washing compositions, and particularl in the form of solutions or gels for the bath or shower, or of make-up remo val products

[00117] Non- limiting six skin care product categories that follow next can be considered a subset of the skin and sun care products:

[00118] (!) Eye Care;

[00119] Non-limiting eye care product forms include; mascaras, eye liners, eye shadows, curlers of eye lashes, eyebrow pencils, and eye pencils

[00120] (2) Lip Care:

[00121] Non-limiting lip care product forms include; lipsticks, tip bal s, lip pencils, lip glosses, lip sprays, transparent li bases, tinted lip moisturizers, and multi-functional color sticks that can also be used for cheeks and eyes.

[00122] (3) Nail Care;

2? [QQI 23] Non-limiting nail care product forms include; nail polishes, nasi varnishes, enamels, nail varnish removers, home-manicure products such as cuticle softeners and nail sirengtheners, and artificial nails.

1001241 (4) Face Care;

[00125] Non-limiting face care product forms include; creams, lotions, solutions_» oils, liquids, peels, scrubs, emulsions, suspensions, mkroemulsions, microencapsulated product, pastes, reconsiitntable product, aerosols, mousses, gels, waxes, glues, pomades, spritees, fecial wet-wipes, putties, lacquers, serums, perms, powders, blush, highlighters, bronzers, masks, and concealers,

100*26] (5) Body Care:

|00J27j 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, waxing products, aid sanitizers,

I QQ 128] (6) Foot Care;

[00129] Non-limiting foot care product forms include: mousses, creams, lotions, powders, liquids, sprays, aerosols, gels, flakes, and scrubs.

[QQ130] Non-limiting oral care product .forms include: toothpastes, adhesives, gums, gels, powders, creams, solutions, lotions, liquids, dispersions, suspensions, emulsions, tablets, capsules, rinses, flosses, aerosols, strips, films, pads, bandages, microencapsulated products, syrups, and lozenges,

[0013! { Also contemplated are personal care compositions comprising polymer(s) described herein complexed with iodine. These compositions can be used in treating skin conditions, non- limiting examples of which include dermatitis, wounds, bacterial infections, burns, rashes, and herpes. These complexed compositions can be staining, substantially non-staining, or essentially non-staining.

[00132] Examples of related personal care compositions are disclosed in U.S. Pat. Nos, 5,599,800; 5,650,166; 5,916,549; and 6,812, 192; US, patent application 2009/0317432; EP 556,660; 661,037; 661,038; 662,315; 676,194; 796,077; 970,682; 976383; 1 ,415,654; and 2,067,467; and WO 2005/032506; each of which is hereby incorporated in its entirely by reference. j00133j It is also contemplated that the personal care compositions can be used in products for male and/or female personal grooming and/or toiletry such as: sanitary napkins, baby diapers, adult diapers, feminine products, products for incontinence, and other related products.

{0fll34| The present disclosure also relates to a coating composition comprising the dihydroxy lactam based polymers as described hereinabove. The coating composition can further comprise at least one coating agent selected from the group consisting of soivents/eosol vents, secondary rheology modifiers, thixotropic agents, binders, cros linkers, pH adjustment agents, pigmems/frUers, flow-control agents, gloss-control agents, coalesced agents, flexibil ng resins, surfactants, waxes, wetting agents, dispersing agents, plasticizers, anti-oxidants, UV radiation absorbers, biocides, extenders, colorants, adhesion promoters, defoaming agents/defoamers, driers, matting agents, and combinations thereof.

{ l 35] Examples of the pigments/fillers can include, but are not limited to calcium carbonate, mica, barium sulphate, !ithopones, zinc oxide, zinc sulphide titanium dioxide (anatase, rutile), chalk, precipitated calcium carbonate, ealcite, dolomites, silicon dioxide, silicic acids, silica flour, pyrogenic silicic acids, precipitated silicic acids, silicates, talc, kaolin, barium sulfates, magnesium silicates, lead, lead oxides, barytes, blanc fixe, sand and glass beads. Special pigments/fillers can include graphene, graphite, carbon nanotubes, carbon, copper, silver, nanosiiver, titanium nanotubes, specially decorated inorganic particles and structures, and the like.

{00136] Mot-Kmiting examples of the solvents/cosolvents can include, but are- not limi ted to, aromatic hydrocarbon solvents such as benzene, toluene and xylene, ethyl benzene, isopropyl benzene, alcohols (ethylene glycol monobutyl ether, ethylene glycol rnonomeihyS ether, diethylene glycol mono butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethy! ether, hexano!, octanol, ethanol, isopropanoi, butanol, n-butano!, ethylene glycol, diethylene glycol, ketones (acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone), diacetone alcohol, dimethyl formanude, n-methyl-2-pyrroiidone, butyrolaetone, ethyl acetate, butyl propionate, water, and the like. [QQ137] No»- limiting examples of the binders can include, but ate not limited to latex emulsion polymers, which are the polymerization products of one or more ethyi.enical.1y ««saturated monomers. Examples of ethylenical!y unsaturated monomers can Include, but are not limited to acrylic acid, acrylonitrile, acetoacetoxy ethyl methacrylate, acetoacetoxy ethyl acrylate, butyl acrylate, butadiene, butyl methacrylate, butyl acrylamide, chloromethyl styrene, crotonic acid, ethyl acrylate, ethyl acrylamide, ethylene, ethyl methacrylate, ethylhexyl acrylate, 2-ethylhexyl acrylate, 2 -ethylhexyl methacrylate, glycidyS methacrylate, hydroxyeihy! ( eth)acrylate, hydroxypropyl (meih)acrylate, isobutyl acrylate, isobutyl methacrylate, isoprene, iso-octyl acrylate, iso-octyl methacrylate i laconic acid, methyl acrylate, octyl acrylate, octyl methacrylate, methyl methacrylate, methacrylic acid, a-methyl styrene, styrene, vinyl chloride vinyl naphthalene, vinyl toluene, vinylidene chloride, vinyl acetate, and the like.

(00138] Other binders used in the present disclosure can include, but are not limited to alkyd resins, polyurethane resins, epoxy resins, and the like, Alkyd resins are generally comprised of polybasic acids, polyhydric alcohols, and fatty acids which can be unsaturated. The poiybasic acids such as aromatic, aliphatic and alicyclic saturated and unsaturated compounds, such as adipic acid, chlorendtc acid, heptanedioic acid, isophthalic acid, maleic acid, napthalic acid, phthalic acid, sebacic acid, succinic acid, trimellitic acid, terephthaiic acid, and tetrahydrophthalic acid. Polyhydric alcohol components include 1,3-butylene glycol, diethylene glycol, dipenteerythritol, dipropylene glycol, ethylene glycol, glycerin, 1,6- hexanediol, neopentyl glycol, pentaerythritol, propylene glycol, sorbitol, trimethylol ethane, trimethylol propane and triethylene glycol. Fatty acids used in the manufacture of alkyds commonly include dehydrated castor oil, coconut oil, cottonseed oil, fish oil, linseed oil, oiticica oil, tuog oil, safflower oil, soya oil, tall oil acids, and the like.

[00139] The polyurethane resin are formed from polyisocyanate (aliphatic, aromatic, or combinations thereof) compounds. Examples of aliphatic isocyanates include butane diisocyanate, 4,4 -diisocyanatodicyclohexylmethane, hexamethyfene diisocyanate, hexahydroxyiylene diisocyanate, isophorone diisocyanate, 1 -methyl-2, 4(2, 6)-diisocyanaio cyclohexane, norboraane diisocyanate, and tetramethyixylylene diisocyanate. Examples of aliphatic and aromatic isocyanates include 4,4'-biphenylene diisocyanate, 4-chloro-L3- phenySene diisocyanate, 1 ,4-cyclohexylene diisocyanate, 1,10-deca-ethylene diisocyanate, methylene bis-(4-phenyl isocyanate), 4,4-methy!ene-bis(eyclohexyl isocyanate), 1 ,5- naphthalene diisocyanate, 1 ,3~phenylene diisocyanaie, 2,4-ioiyieae dusoeyanate, 2,6-loly!ene diixocyanate, 1 ,4-tetramethylene diisocyanate, 1 ,5-teirahydK>naphthalene diisocyanate, and the like.

[00140] In addition to isocyanates, alcohols and carboxylic acids, which form polyester compositions, can also be used in the preparation of polyurethane resins. The carboxylic acids can be of an aliphatic, cycloaliphatic, aromatic and/or heterocyclic nature and can comprise halogen atoms and/or unsaturated moieties. Suitable acids include adipic add, azeteic acid, bis- glycol terephthalate, diraeric fatty acids, dimethyl terephthalate, endontethyleneietrahydropluhalk anhydride, fumaric acid, glntaric anhydride, hexahydrophthalie anhydride, isophthalic acid, maleic acid, maleic anhydride, phthaHc anhydride, phtbalic acid, suberic acid, succinic acid, sebaeie acid, tetrahydrophthalic anhydride and tetracblorophlhalic anhydride. The alcohols examples include 1,4-, 1 ,3- and 2,3-butylene glycol, cyclohexanedunethanoi (1,4-bis-hydroxymeihylcyc!ohexane), diethylene glycol, dipropylene glycol, dibutylene glycol, ethylene glycol, 1 ,2- and 1 3-propylene glycol, 1,6- bexanediol, 2-mefhyl-l ,3-propanedibl, neopentylglycol, 1,8-octanedioI, polyethylene glycol, polypropylene glycol, polybutylene glycol, triethylene glycol and tetraethy!ene glycol Diols comprising carboxyl or carboxylate groups which are suitable to support ionic or potentially ionic groups are envisioned. Such moieties can be constructe by dihydroxysuccinic acid, dimeihylolacetic acid, 2,2-dimethylolpropionic acid, 2,2~dimeiliyIoibutyric acid and 2,2- dimeihylolpentanoic acid.

[00141] Polyester compositions can be made as part of this inventions as well. Polyesters comprising carboxyl groups and terminal carboxyl groups are envisioned. Also, polyesters constructed from lactones are also envisioned. Polyesters obtained from a reaction mixture comprising at least one dihydroxy lactam moiety and at least one functional moiety having a hydroxyl-reactive functional group, wherein the functional moiety having a hydroxyl-reactive functional group is selected from the group consisting of phthalic anhydride, isophthalic acid, maleic anhydride, chlorine/bromtne containing anhydrides and fumaric acid. The polyesters can further comprises one or more non-lactam moiety selected from the group consisting of aliphatic/aromatic alcohols with a carbon chain length of Cl. -Cl 8 , alkoxylated. alcohols with a carbon chain length of Cl-C18 alcohol ethylene glycols, alcohol meth(aeryiates), polyvinyl alcohols, polycarbonatepolyois, polybutylene glycols, polyethylene glycol, polypropylene glycols, hydroxypolyesters, hydroxypolyefhers, bydroxypolythioesters, hydroxypolyacetals, hydroxypolycarbonates, polyeiherpolyols, polyesterpoiyok, poiycarfeonatepolyois, hy roxypotyesiers, hydroxypo!yethers, hydroxypolythioesierx, hydroxypolyacetals, hydroxypolyearbonates, aliphatic and aromatic polyether polyols, caprolactone-based polyols, polyfethylene glycol)-soyamine, polyfeihylene glycol) castor oil, polyethylene glycol)- hydrogenated castor oil polyfethylene giycolHanolin, polyethylene glyco1)~lanolin wax, polyethylene glycoi>polyvmy!idene fluoride, polyethylene glycoi)-poly(vinyl acetate), poly thylene glyeol)~pol>Oxymethylene, polyethylene glycol)-ester, an combinations thereof.

1QQI 42 { Polycarbonates comprising hydroxyl groups are useful and are prepared by reacting diols with dicarbonates such as diphenyl carbonate or phosgene.

]00143j Polyethers comprising diols, formed from polymers derived from ethylene oxide, propylene oxide and/or tetrahydxofuran are also useful An amine functionality can be employed to introduce terminal hydroxyl functionality, with compounds such as diethanolamine, ethanolamine, N-meihylethanoLamine, propanolamine, N,N,N'~tri.s-2- hydroxyethyl-eihyiendiamine.

100144] The epoxy resins are comprised primarily of linear chain molecules. These molecules are formed from the reaction of bisphenols with haiohydrins to yield epoxy resins containing epoxy groups. Common bisphenols include bisphenoI-A, bisphenol-F, bisphenol-S, and 4,4^? dihydroxy bisphenol. Common haiohydrins include epicMorohydrin, dicMorohydrin, an 1 ,2-dichloro 3 hydroxypropane. Examples of commercially available epoxy resins include D.B.R™ 333 and D.E.R.™ 661 from Th Do Chemical Company; EPON™ 828, EPON™ 836, and EPON™ 1001 from. Momentive Specialty Chemicals Inc.; Gha-Geigy epoxy resins GT-7013, GT-7014 GT-7074, GT-250 f m Huntsman; an Ancare ⁵* AR 555 from Air Products.

100145] Non-limiting examples of the secondary -rheology modifiers can include celluloses and cellulose derivatives, guar and guar derivatives, modified ureas, polyurethane thickeners and associative thickeners, alkali swell able emulsions (ASEs), hydrophobicaliy modified alkali swellable emulsions (HASEs), hydrophobicaliy modified polyurethanes (HEURs), hydrophobicaliy modified polyethers (i-lMPEs), attapuigites, hydrophobicaliy modified polyacetal polyethers (HMPAPEs), acrylate thickeners, amides and organic deri vatives, fumed silicas, synthetic layered silicates, organoelays_* mixed minerals, thixotropy boosters, poiyalkylene ether derivatives, starches, polyacrylates, and the like,

106146] Noil-limiting examples of the pH adjustment agents can include, but not limited to monoethanol amine, triethanol amine, methyiam oethanoi, 2-amino-2-methyl-l -propanol, 2- (n-hulylamino) ethanol, ammonium hydroxide, ammonia, caustic, potassium hydroxide, formic acid, acetic acid, citric acid, organic acids, minerals acids, hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, and the like.

{00147] Non-limiting examples of biocidal agents can include, but not limited to 2-n-octyl- 3-isoihiazolone, chioroihalonil, earhendazim, diuron, isothiazoione, 2 -oc iy i -21-1 -i so th i a/o 1 -3 - one (0IT), iodopropynyl butyl carbamate (IPBC), sodium 2-pyridme hiol~l -oxide, zinc 2- pyridinethioi-i-oxide, l,2-dibromo-2,4-dicyauobuiane, 2-(4-thiazolyi}-benzimidazole, thiabendazole, tebuconazole, methylene bis(thiocyai te), 2-ithioeyano-methyithio)- benzothiazole, octhilmone, barium meiaborate, propiconazole, diiodomethyi p-toiyl sulfone, 3-iodo-2-propynyi butyl carbamate, n-(trichloromeihylthio) phthalimide, tributyltin benzoate, alkyl amine hydrocMorides, n~mchiaromethyitblo-4-cyclohexene-l ,2-dicatboximide, 2- methylthio-4-tert-butyl-amrao~6~cyciopropylaraino-s-triazine, teirachloroisophthaioratrile, zinc dimethyldithiocarbamate, zinc 2-mercaptobenzothiazole, trans-i ,2-bi:s{ii-propyl-sulfouy1 ethane, 4,5-dichloro-2-n-octyi-3-(2H)-isothiazoione, 4,5-dichioro-2-octyl-4-isothiax0lin-3~ one (DCOIT), carbendazira, Irgaroi, 10,10 -oxybisphenoxarsine, iriciosan, 2-metltyltbio-4- tert-buiyl-amino-d-cyciopropyiarnmo-s-iriazitje, n-cyclopropyl-N^?-(! ,l-dimeihyietbyi)-6- )methyItb.io)-i ,3,5-tr.iazme~2_s4-diamine, zinc dimeihyldithiocarbamate (Ziram), Irgaroi® 1051 (commercially available from BASF SE), tributyltin oxide (TBTO), S-cMoro-methyi- H- isotbiazol-3-one/2-metliyl'2H-isothiazol-3-one (C1T/MIT), benzisotfaiazolmone (BIT), meihyhsoihtaz.olmone (MIT), bexahydro-l,3,5-iris(2-bydroxyethyl)-S-iriazme, sodium pyrithione, zinc 2-pyridmethioM -oxide, l ,2-benzoisotbiazoIin~3~oue, glutaraldehyde, 2,2- dibromo-3-nitrilppropionamide (DBNPA), poly(hexametbylenebigiianide} hydrochloride (PHMB), 2-bromo-2-iiittOpropane-l ,3-dlol (Bronopoi), 1 ,2-dibromo~2-4-dicyanobutane, 1- bromo-l-(bromomeihyl)~i,3-piOpanedicarbonitrile, 2,2~dibromo~3-nitrio-propionarnide, benzyl bromoacetate, I -bro o- 1 -(broraoraethyl)- 1 ,3-propanedicarbonitrile, Dazomet, dodeey!gua dine hydrochloride, methylene dithiocyanate, 1 -methyl-3,5, 7-triaza-l- azoniaadamantane chloride, 2-hromo-4'-hydroxyacetophenone, dibromo-3- niiriloprepionamide, l,2-benzisothia¾>lin-3-one, hexahydrotriazine, bromo-beta-nUrostyrene, ethyIdihydro~lE3H 5H-oxa/Qlo(3,4-C)oxazQle, acetoxy-2_>4~dimefiiyI m-dioxafte_i nitrobuiyl morpholine, elhyl~2- troliimetbyiene disuorphohne, sodium o-phenylphei e, chloroallyl- 3,5,7-azoniaadamantane chloride, sodium salt of biplienyloL tributyMn benzoate, alkylamine hydrochloride, mixture of monocyclic oxaxoiidines, n-methyl 2- hydroxymethyieneoxypropyl-2'~hydroxypropyiamine, sodium hydroxymethyl glyeinate, mixture of bicyclic oxazoiidines, 13-bis{liydroxymethyi}-5,5-dimethyi h dantoin, hydroxymethyl 5,5-dimethylhydantoin, 5-chloro-2-meihyi-4-isotbia oii»-3-Qne, 2-methyl-4- isothiazoKn-3-one, 2-methyl-4-isothiazoI -3-one, and combinations thereof.

100148 Non-lhniiing examples of colorants can include pigments and/or dyes. Suitable pigment materials can be found in Hunger’s“Industrial Organic Pigments,” Itoh’s“Dictionary of Pigments,” and Leach and Pierce's“Printing Ink Manual.” Examples of inorganic pigments can include, but are not limited to, pigment blacks (lamp, furnace, channel blacks), iron oxides (red, yellow, brown, black, transparent, etc.), spinel black, chromium oxides green, chromate yellows, iron blues, zinc chromate, molybdate orange, molybdate reds, ultramarine, cadmium, mixed phase pigments (nickel titanium yellow, chromium titanium yellow, cobalt green, cobalt blue, zinc iron brown, iron manganese black), all types of metallic powder pigments such as aluminum powder, gold powder, silver powder, copper powder, bronze powder, and brass powder; or their metal flake pigments; mica flake pigment; mica flake pigments which have been coated with metallic oxides; mica shape oxide pigments, and the like.

1001491 Organic pigments can include, but are not limited to, onoazo pigments (aceioaeetarylide, benziniidazolone, naphthol AS, pigmented b-naphihol dyes), disazo pigments (axo condensation pigments, dipyrazolone), polycyclic pigments (quinacridone, dioxazine, pery!ene, dikeiopyrrolo-pyttole, isoindoime), and metal complex pigments (Cu- phthalocyanines). Examples of the dyes can include metal complex dyes, anionic dyes, azo dyes, and the like fOOISOj The cellulose derivatives can include, but are not limited to, ethyl cellulose (EC), hydroxyethyl cellulose (EEC), hydroxypropyl cellulose (HPC), ethy!hydroxyethyl cellulose(EBEC), carhOxymethyl cellulose (CMC), carboxymethylhydroxyethyl cellulose (CMflEC) hydroxypropyihydroxyethyl cellulose (HM.HEC), methyl cellulose (MC), methy!hydroxypropyl cellulose (MHPC), methy!liydroxyethyl cellulose (MHEC), carboxymethylmetliyl cellulose (CMMC), hydrophobically modifie catboxymethyl cellulose (HMCMC) hydrophobically modified hydroxyethyl cellulose (HMHEC), hydrophobically modified hydroxylpropyl cellulose (HMBPC), hydrophobically modified eihylhydtoxyeifavi cellulose (H EHEC), hydrophobically modified carhoxy¾eihyjhydroxyethyI cellulose (HMCMHEC), hydrophobically modified hydroxypropylhydroxyethyl cellulose (HMHPHEC), hydrophobically modified methyl cellulose (HMMC), hydrophobically modified meihylhydroxypropyi cellulose (HMMHPC), hydrophobically modified methyihydroxyethyt cellulose (HMMREC), hydrophobically modified carboxymethylmoihyl cellulose (HMCMMC), cationic hydroxyethyl cellulose (cationic MEC), cationic hydrophobically modified hydroxyethyl cellulose (cationic HMHEC), nano fibnllaied cellulosics (NFC), and microfibri Hated cellulosics (MFC). jOOISI j The guar and guar derivatives can include, hut are not limited to, carboxymethyl guar, earboxymethylhydroxy propyl guar, cationic hydroxypropyi guar, hydroxyalkyl guar such as hydroxyethyl guar, hydroxypropyi guar, and hydroxy-butyl guar, carboxylalkyl guars such as carboxymethyl guar, carboxylpropyl guar, caiboxybutyl guar, and the like.

100152] Examples of the defoaraing agents or defoamers can include, but are not limited to, silicone defoamers, silicone defoamers comprising po!ysiloxane and hydrophobic particles, silicone-free defoamers comprising hydrophobic particles and polymers, silicone-free defoamers comprising polymers, mineral oil defoamers comprised of paraffin base mineral oil, hydrophobic particles, and polysi!oxanes.

|00153| Surfactants can provide excellent surface tension reducing capabilities for substrate wetting. Surfactants used in the present disclosure can be nonionic and anionic surfactants.

(00154] Examples of the nonionic surfactants can include, but are not limited to, C 12-C18 fatty alcohol ethoxylates, CI2-C 14 fatty alcohol ethoxylates, Cl 6-08 fatty alcohol ethoxylates, C13-C15 oxo alcohol ethoxylates,€10-08 alcohol ethoxylates. C l 3 oxo alcohol ethoxylates, CIO Guerbet alcohol ethoxylates, CIO Guerbet alcohol alkoxylates, CIO oxo alcohol ethoxylates, alkyl polygiueosides (e.g._;€8-0.0 alkyl po!ygiueoside, C8-C14 alkyl polyglucoside, C12~C14 alkyl polyglucoside, blends of 2-00 alkyl polyglucoside on inorganic and organic carrier, amine ethoxylates (e.g., oleyl ai ne+12 EO, coco amine+12 EO), aminopolyo! (e.g., triethauol amioe+18 EO, ethylene diamine PO), alkyl pyrrolidones (e.g., N -octyl pyrrolidone, N-butyl pyrrolidone, N-dodecyl pyrrolidone), resin precursors and additives (e.g,, Bisphenol A ethoxylates, BIS A+-3 EO, BIS A44 EO, BIS A+6 EO), emulsifiers and solubilizers (e g., 4-Cl O- 13-see-alkyl derivatives of benz estilfouic acid calcium salts. castor «iH-20 BO, castor oίI+~·35 ED, castor eil-iOO BO, epoxidized vegetable oil, ethoxylated rape seed oil, sorbitanester ethoxylaied, deeyl aleoho!-E~3 BQ, C 8 fatty alcoho.H4 EO, fatty alcohol ethoxylate, C8-C10 fatty alcohoH~5 SO, C12-C14 fatty alcohol+~50 BO, ethoxylated sorbitan trioleate castor oil ethoxylate, phenol ethoxylate, alcohol ethoxylate, ethoxylated mono-Zdi glyceride), foam suppressors (e.g., polyalkoxyester and solvent, fatty alcohol alkoxylate, carboxylic acid ester, phosphoric acid ester, combination of paraffin and silicon on carrier, alkyl polyalkylene glycol ether. Guerbet alcohol C16+~2 EO, fatty alcohol alkoxylate), low-foaming nonionic surfactants (e.g., fatty alcohol alkoxylate, modified fatty alcohol polyglycol ether, amine alkoxylate, end-capped Guerbet alcohol alkoxylate, end- capped fatty alcohol alkoxylate, FO/EQ block copolymers), tauramine oxide, cocamidopropylamine oxide, aikylamido propyl betaine, polyglycol ether of an aliphatic diol, oleic acid amide 10 EO, emulsifiable methyl canolate, unsatnrated fatty alcohol ethoxylate,fatty alcohol poly glycol ethers, faty alcohol poly glycol ethers with fatty acid, unsaturated fatty alcohol ethoxylate), polyethylene glycols, polypropylene glycols, methyl polyethylene glycols, alkyl polyalkylene glycol copolymers, alkyl polypropylene glycols, polyfunctions! polyalkylene glycols, reactive polyalkylene glycols. 00155] Other noniomc surfactants can include, but are not limited to, alkylphenol ethoxy lates such as nonylphenol ethoxylates and octylpheno! ethoxy fates, secondly alcohol alkoxylates such as secondary alcohol ethoxylates (TERGITOL™! 5-S-9, commercially available from The Dow Chemical Company), and primary alcohol alkoxylates.

[00150] Examples of anionic surfactants can include, but are not limited to, sodium salt of lauryl ether sulfa te+2 EO, sodium sal t of iso-tridecy ! alcohol ether suHate+20 EO, sodium salt of faty alcohol ether $u!fate+2 EO, sodium salt of fatty alcohol ether sulfate+4 EO, sodium salt of faty alcohol ether sulfate+7 EO, sodium salt of fatty alcohol ether sulfatet l2 EO, sodium salt of fatty alcohol ether sulfaie- O EO, sodium salt of fatty alcohol ether sulfate+50 EO, sodium salt of C12-C14 fatty alcohol ether sulfate·*· 1 EO, sodium salt of 02-04 faty alcohol ether sulfate+2 EO, sodium salt of C12-C14 faty alcohol ether sulfate+3 EO, ammonium salt of C8-C14 fatty alcohol sulfate, sodium salt of 2-efhylhexyl sulfate, sodium salt of 06-08 fatty alcohol sulfate, sodium salt of 02 fatty alcohol sulfate, sodium salt of € 12-04 fatty alcohol sulfate, sodium salt of 02-06 fatty alcohol sulfate, sodium salt of 02-08 fatty alcohol sulfate, sodium salt of 06-08 fatty alcohol sulfate, sodium salt of C8 fatty alcohol sulfate, sodium salt of linear C10-C13 alkyl ben ene sulfonate, sodium salt of linear C 10-0.13 alkyl benzene sulfonic acid and potassium salt of oleic acid sulfonate.

|00iS7| Other surfactants used in the present disclosure can include, but are not limited to ester quats, sodium salt of alkyl ether phosphate, sothiim-N-lauryl-JS-imiuodipropiouate, acid phosphoric ester of a fatty alcohol eihoxy!ate-B EG, sodium salt of mono-alkenyl snifosuccinaniate, sodium salt of mono-alkenyl suifosuccimue÷5 EQ, sodium salt of di- isodecyS sulfbsuccioate, sodium dioctylsulphosuccinate, acid phosphoric ester, amine salt of dodecylbenzenesulphonate, alkyl ester phosphate, and the like.

|00158) Non-limiting examples of coaleseent agents can include ethylene glycol monobutyl ether acetates, diethylene glycol nionoethyi ether, lower monoalkyi ethers of ethylene or propylene glycol (propylene glycol methyl ether), dimethyl succinate, diethyl succinate, diisopropyl succinate, tohiates (e.g., 2-ethoxyethyi p-toluate, 2-propoxyethyl o-totoate, 2- ethoxyethyl o-toluate, 2-eihoxyethyS benzoate, 2-{2-ethoxyethoxy)ethyl p-ioluaie), benzoates (e.g., 2-(2~ethoxyet.hoxy}ethyl benzoate, 2-propoxyethyl benzoate, 2-methoxy- 1 -methylethyl benzoate, 2-(2 -raethoxy- 1 -methylethoxy)- 1 -raethy lethyl benzoate, 2-propoxy- 1 -methylethy! benzoate). Levulinic acid ester of 2-hexyl- 1 -decaaol, tevuiimc acid ester of l -ielradecanol/2- hexyldecanoi, di-octyl succinate, poiytrimetliylene ether glycol, hexylene glycol, butoxyethyoxypropano!, n~propoxypropanoi, n-butoxypropanol, diethylene glycol monobutyl ether acetate, phenyl glycol ether, 2,2,4-trimethyipentanediol- 1 ,3-monoisobu¾nate, n-dibutyl glutarate, n-dipentyl glutarate, n-dihexyl glutarate, n-dihepiyi glutarate, n-dioctyi glutarate, diisobutyl glutarate, di-2-methylbutyl glutarate, di~4~methyl-2~pentyl glutarate, di-2-ethyl.hexyl glutarate, pentylol glularate, tetrapropylene glycol monobutyl ether, an the like. Mixtures of these compounds are also suitable as coalescing agents.

(QQ159] Coaling compositions comprising the dihydrox lactam based polymers according to the present disclosure can be applied to a variety of surfaces and substrates. These surfaces and substrates can include, but. are not limited to, asphalt, cement, concrete, drywall, glass, masonry, metal, paper, plastic, textile, wall paper, and wood. The coating compositions according to the present disclosure can provide an enhanced hiding power to substrates coated with the compositions. fbblhO] The present disclosure is further directed to a pharmaceutical composition comprising; (I) a polymer obtained from a reaction mixture comprising (i) M-(2,3- dihyfrtoxypropyib^-pyrroIkioBe and/or l~|2-{2,3-djhydroxypropyIoxy)el J]-2~pynoiidone; and (it) polyiD.L-tactide), wherein (i) and (ii) independently present in amount of about 0.01 mole% to about 99.99 moles% and the polymer is a polyester, and (II) one or more pharmaceutically acceptable additt ve.

|00I61] According to one of the embodiments, the pharmaceutically acceptable additive is selected from a group consistin of plasticizers, disintegrants, surfactants, lubricants, glidanis, carriers, anti-adherents, fillers, wetting agents, pH modifiers, binders, solubility modifiers, reerystalUzation inhibitors, coating agents, diluents, coloring agents, preservatives, anfi oaming agent, antioxidants, buffering agents, acidifying agents, alkalizing agents, complexation~enhancing agent, cryoprotectant, electrolytes, gelling agents, emulsifying agents, solubility-enhancing agents, stabilizers, tonicity modifiers, flavors, sweeteners, complexing agents, fragrances, and viscosity modifiers.

100162] The present disclosure is also directed to a process of preparing a polymer comprising: (A) (i) at least one dihydroxy lactam moiety, an (ii) at least one functional moiety having a hydroxyl-reactive functional group; wherein (i) and (ii) are independently present in amounts of about 0.01 ole% to about 99.99 raoles% and the polymer is selected from the group consisting of polyester, polycarbonate, polyeiher, poly (ester ether), poly (ester amide), poly Imide, polyamide, poly acrylates an poly (ester imide); or wherei each (i) and (ii) is present in amounts of other than 50 moie% and the polymer is a polyurethane; (B) charging (A) into a reaction container under inert gas atmosphere with solvent; (C) stirring the reaction mixture of (B) and maintaining temperature at 55-70°C for about 30 minutes; (D) charging an additional reactive moiety to (C); (£) polymerizing (D) with catalyst for 3-5 hours; and (F) retrieving desired polymer from (E).

1QQ163} A solvent can be used for the synthesis of the polymers according to the present disclosure. Any solvent without active hydrogens can be used. Non-limiting examples of solvents can include acetone, dimethyl acetamide, toluene, xylene, aliphatic hydrocarbons, dialky! ethers of alkylene glycols and diethoxyraethane.

199164] According to another embodiment, the solvent system is present in an amount from about 60% to about 99,9% by weight of the thickener system. In another embodiment, other possible ranges of solvent system would include, but are not limited to, from about 60 wi ¾ to about 70 wt from about 70 wt. % to about 80 wt 94; front about 80 wt % to about 90 wt %; from about 90 wt % to about 99.9 wt % f0016S] A catalyst can be used for the synthesis of the polymers according to the present disclosure. Non-limiting examples of catalysts can include dibutyltin diiaurate, 1,4- diazabicyclo[2, 2, 2 joctane, trietliyi amine, pyridine, and paratoulenesulfonic acid.

{00166] The present disclosure relates to a method of thickening a composition comprising adding the dihydroxy lactam based polymer described hereinabove into the composition. Examples of the compositions can include, but are not limite to, coating compositions, construction compositions, personal care compositions, oilfield compositions, drilling fluids, drilling muds, cementing fluids, servicing fluids, gravel packing muds, fracturin fluids, completion fluids, workover fluids, spacer fluids, household, industrial and institutional compositions, pharmaceutical compositions, food compositions, biocides, adhesives, inks, papers, polishes, membranes, metal working fluids, plastics, textiles, printing compositions, lubricants, preservatives, agrochemicals, and wood-care compositions.

[Ml 7] The polymers and their applications according to the present disclosure can be prepared and used according to the examples set out below. These examples are presetted herein for purposes of illustration of tire present disclosure and are not intended to be limiting, Ibr example, the preparations of the polymers and their applications.

EXAMPLES:

[00168] In the examples, the following abbreviations are used:

EPDIOL: ^]-[2-(2,3-dihydroxypropyloxy)ethyl)-2-pym)lidone

PEG.1: Polyethylene glycol with approximate Mr. -7860, and Mw=8240

PEG2: Polyethylene glycol with approximate Mn—3640, and M«=^::3790

DBTD : Dibut ltin diiaurate

HMDI: 4,4’ -Methy lenebisf'cydohexyl isocyanate)

HD!: Hexamethylenediisocyanate

IPDI; Isophorone Diisocyanate

DMBA; Dimetliylol butyric acid

DMAc: Dimethyl acetamide

MBPl:4,4’^«Methylenebis (phenyl isocyanate)

DMPA: Dimetliylol propoionie acid MIJEA; Methyl diethaeol am me

EA: Triethyl amine

DM1: D »ne thy i i t aconaie

MA: Maleic anhydride

Act , Cl: Acryloyl chloride

GMA: Glycidyl Methacrylate

[QQ 69) Example 1: Reaction of EPDIOL with Glycidol

100170] A mixture of Giycido! (5.45g) and EPDIOL(l 5g) was mixed in mixture of acetone and TEA (40g) in a round bottom flask equipped with a stir bar and a heating mantle, the mixture was stirred at SS C for 6 hours. The resulting mixture was clear and the resulting product was verified by IR through the disappearance of the epoxide absorbance bands in the 800 region and the formation of the ether absorbance band (1 100~ 1,200 era ¹),

[00171] Example 2: Reaction of EPDIOL wi th Succinyl Chloride

[00172] A mixture of Succinyl Chloride (1 L44g) and EPDiOL(I5g) was raked in acetone (50g) in a round bottom flask equipped with a stir bar and a heatin mantle, the mixture was stirred for 2 hours at 55'³C The resulting mixture was dark brown in color and the resulting product was verified by IR through the formation of the 1735 cm’ester absorbance band.

[QQI73} Example 3: Reaction of EPDIOL with DM!

[00174) A mixture of DM1 C 11 ,65g) and EPDIOLi l 5g) was mixed in a mixture of acetone and TEA (50g) in a round bottom flask equipped with a stir bar and a heating mantle, the mixture was stirred for 4 hours at 55^CC. The resulting mixture was clear and the resulting product was verified by IR through the reduction of the methoxy CEL band at 2840 cm ⁵ and the formation of the ester absorbance band at 1730,

[00175] Example 4: Reaction of EPDIOL with MA

[ 0176] A. mixture of M A ( i Sg) and EPDIOL(3 i .1 Og) was mixed in acetone (65g) in a round bottom flask equipped with a stir bar and a heating mantle, the mixture was stirred at 55^'O for 6 hours. The resulting mixture was yellowish in color and the resulting product was verified by through the disappearance of the anhydride 1850 cm⁴, 1774 cm ¹ peaks and the appearance of the 1717 cm ¹ ester peak. {00177} Example 5: Reaction of EPDIOL and Acr .Cl:

{00178} A mixture of Acr.CI (6.68 g) and EPD!OL(43g) was mixed in acetone (43g) in a round bottom flask equipped with a stir bar and a heating mantle. The mixture was Amber added with triethyl amine as a catalyst and the mixture was stirred for 2 hours at 55°C, The resulti ng mixture was orange in color and the resulting product could he verified by IR through the ester peak of 1730 curb

{0 179} Example 6: Reaction of EPDIOL and GMA

{00180} A mixture of GMA (10.49g) and EPDIOL(I5g) was mixed in acetone (50g) in a round bottom flask equipped with a stir bar and a heating mantle. The mixture was further added with triethyl amine as a catalyst and the mixture was stirred at 55”C tor 2 hours. The resulting mixture was clear in color and the resulting product could be verified by IR through the disappearance of toe epoxide 844 absorbance band and formation of the ether absorbance baud at 1 ,100 cm ⁵.

{00181} Example 7: Reaction of EPDIOL and Phosphorus oxychloride

{00182} A mixture of Phosphorus oxychloride (I 1.30g) and EPDIOL (15g) was mixed in acetone (5 Og) in a round bottom flask equipped with a stir bar and a heating mantle. The mixture was further added with trieihyi amine as a catalyst and the mixture was stirred for 4 hours. The resulting mixture was dark brown in color.

100183} EPDIOL based Polyurethanes

{00184} Example 8: Reaction of EPDIOL with MBPl

{00185} EPDIOL (0,5 moles) and DMAc were charged to a process reactor. The reaction mixture was stirred and heated to a temperature of 6S-?0¾. Further, MBPl (L I moles) was charged to the reaction mixture and the reaction mixture was stirred lor 5-15 minutes. DBTD (2 0% by weight of isocyanates) was added to the reaction mix tore and stirred for 5 hours. The contents were discharged and allowed to cool to ambient temperature to give polymer,

{001 6} Example 9: Reaction of EPDIOL with PEG2, DMBA, HD1 and Hexanol

{00187} EPDIOL (0.73 moles), PEG2 (0,32 moles) and DMBA (0.95 moles) and Acetone were charge to a process reactor. The reaction mixture was stirred and heated to a temperature of 70-?5*(T^'€. Further, HDi (2 1 moles) was charged to the reaction mixture and the reaction mixture was stirred for 5-15 minutes. DBTD (2 0% by weight of isocyanates) was added to the reaction mixture and stirred for 4 hours. Hiexanol (0,2 mo s) was added and stirred for 1.0 hours. ethyl amine was added to neutralize DMBA and the contents were discharged and allowed to cool to ambient temperature to give polymer

100188] Example 10: Reaction of EPDIOL with MDEA, PEG2, HDI, and Hexanol fOOISO] EPDIOL (0.73 moles), PEG2 (0.32 moles) and methyl diethanol amine (0,95 moles) and Acetone were charged to reactor. The reaction mixture was stirred and heated to a temperature of70-75^uC. Further, HDI (2 1 moles) was charged to the reaction mixture and the .reaction mixture was stirred for 5 minutes, DBTD (2.0% by weight of isocyanates) was added to the reaction mixture and stirred for 5 hours. Hexanol (0,2 moles) was added and stirred for 1.0 hours. Acetic acid was added, the contents were discharged and allowed to cool to ambient temperature to give polymer.

(00190) Example 11: The reaction of Example 9 was repeated by replacing DMBA with DMPA and by replacing HDI with IPD!.

(00191 j H drophobical! modified urethane— ethoxylates (HEIJR) polymers

(00192) Hydrophobically modified nreihaue— ethoxylates (HBUR) polymers are prepared by incorporation of EPDIOL monomer onto the backbone of a urethane ethoxy!aie polymer

“Structure - 1”.

: socyanate

R^:: Alcohol

xyv+z-IOO

(00193) Structure -1

100194] Example 12(a); EPMOL-IPDRiEUR

{00195] Hydrophobically modified uretbane— ethoxy laies (HEIJR) polymers were prepared by reaction mixture c mprising EP.D10L monomer and IFDI are depicted in Structure -2 and described in below examples.

1001961

Structure -2

Table 1; EPD3 OL-PEG I -IPDl-HexaBol-HEUR

Table 2: EPDIOL-PEG2-IPDi-Hexanol-HEUR

Table 3: EPDIOL-PEGl -lPDI-Hexanol-flEUR

tiEPDiOL meansTarget number of EPDIOL per chain.

(00198) Example 13: Solvent process

(001 9) EPDIOL ( 12.71 g) was dissolved in I5g anhydro m acetone and charged to a process reactor along with S 82.53g of PEG2 and 175 g of anhydrous acetone. The reaction mixture is mixed and heated to 65-70°€. Further, IPDI (27.46g) in 15g anhydrous acetone was charged at the temperature, was mixed for 5-15 minutes. Then charged O.590g of DBTDL (Dibutyltin dilaurate) in lOg acetone. Mixed for 5 hours. Further, charged 2.53g hexanol and continued the reaction for 1.Ohour. At the end, the product was discharged, the product was either dried in a vacuum oven or subjected to solvent exchange into water

|00200) Example 14: EPDIOL-HMDl: liElIR polymers

Table 4: -BPDIOL-PEG 1 -HMDI-Hexano HEU

(00201) Example 14(c): Melt process

(00202) polyethylene glycol (PEG!) { 1,376.5%}, EPDIOL (I8,88g), were charged to a process reactor. The reaction mixture was heated to 100 1 I0*C and stirred under vacuum for 0.5-L0 hours. The reaction mixture was cooled to 75-80*0 and further charged HMD! (89.30g) and mixed for 5-15 minutes. Afterwards, dibuty ltin dilaurate (1.92g) was charged and mixed for 2.0-2.5- hours at 100- 1 10°C. Once mixing completed, hexanol (16.83g) was charged and continued the reaction for 1.0 hours. After the reaction completed, the contents were discharged and allowed to cool to ambient temperature to give polymer.

[00203] Example 14(d): Solvent process

J00204] EPDIOL { 1.89g) was dissolved in anhydrous acetone ( ! 5g) and charged to a process reactor along with polyethylene glycol I (PEG !) (13?.6Sg) and acetone (245g). Stirred and heated the mixture to 65-70*C. At temperature, a mixture of (8.93g) HMD! in (I5g) acetone was charged and mixed for 5-15 minutes. Then (0.20g) dibutyhin dilaurate was charged in (lOg) acetone and mixed for 5 hours, then hexano! (L68g) charged in (35g) acetone and continued the reaction for 1.0 hours. The product was discharged, and either dried in a vacuum oven or solvent exchange into water.

|0O2«5] Example 15: EPDIOL-HD1-HEUR Polymers

|0O205] EPDIOL-HDI-HEUR polymers of Struct» re-3 were prepared by following compositions of EODiOL.

100207]

{00208]

Structured?

Table 5: EPBIOL-PEG 1 -HDLHe anohHElJR

Table & EPGIOL-PEG2~PIDI-Hexanol-HEUR

Table 7; HPDIOL-PEG ! -HDI-Decanol-HEUR

Table 8: EPDIOL-PEGi -HDi-Deeanol- HEUR

|00209] Exampl 5 ( ): Solvent process

|0S2I0] EPDIOL ( 2 69g) of in 15g anhydrous acetone was charged to a process reactor along with I88,96g of FEG2 and 175, Og of anhydrous acetone. The reaction mixture is raked and healed to 65-?0^eC Further, a mixture of2i 05g HDi it 15g anhydrous acetone was raised for 5- 15 minutes at the temperature. Then 0453g DBTDL in lOg acetone was charged to the reaction mixture. The reaction mixture was mixed for 5 hours. Farther, 2.53g hexanol was added to the reaction mixture and the reaction is continued for 1 0 hours. At the end of the reaction the product was discharged and the product was either dried in a vacuum oven or solvent exchange into water.

f00211 ] Example I S (I): Mel t Process

|002I2] EPDIOL (18 88g) an polyethylene glycol (PEG) -were charged to a process reactor Heated the reaction mixture to ItHM ICPC and stirred under vacuum for 0.5-1 0 hours. Cooled to 75-80°C and charged HMD! (89.30g) and mixed for 5- 13 minutes. Afterwards, dibutyhin dik rate (1.92g) was charged said mixed for 2.5 hours at 100- 1 1 ifoC. Once mixing is complete, hexane! (I6.83g) was charged and continued reaction for 1.0 hours. After reaction is completed contents were discharged and allowed to cool to ambient temperature to obtain product m *3] Application of EEMOL-HEli R examples in coatings:

f00214] Example 16: Base paint preparation

100 151 A semi-gloss base paint formulation without low shear and high shear thickenerswas prepared by raking the grin formulation given in Table 9 A and letdown formulations given in Table 9B, During the let-down phase, low shear polymer, high-shear polymer examples and water were withheld.

Table 9A: Grind Formulation

Grind for 15 minutes to achieve ¾ Hegman scale 4-5

DrewplusTM T-4304: A d batner, eotonserdahy available from Ashland Inc,

Minex® 7: Micronized fun ksnai filler aving a median parhcte size oi .5 microns, commercially available from The Caty Company Table 9B: Letdown Formulation

Rhoplex VS 1050: acrylic enrutsioa from Dow Chemical company

Optifii TM Chancer 400: s coalesce»!, commercially available from Eastman Chemical Company.

Polyphase 678: a fungicide, commercially available from Troy Corporation. 002163 Exampl 17: EPDIOL HEUR polymer compositions

Table 10: BPD10L HEUR polymer compositions

00217] Example 18 ( a): Comparative control Example I - semi -gloss formulation

100218] I» comparative control Example 17(a) Aqaaflow XLS 530 was added as low-shear (LS) polymer and Acrysol RM202O (€6 HMD! ) was added as high-shear (HS) polymer along with water to the base paint formulation shown in table 9 A and 9B. The dosages of LS, HS polymers and water were adjusted to achieve a target Krebs stormier viscosity of 165*5 KU ««its and an ICI viscosity of 130x1.0 m.Pa.s.

100219] Example 19: Semi-gloss Formulation

|0O22O] In comparative Example 17(b), Aquaflow XLS 530 was added as low-shear (LS) polymer and polymer solution example 17 (h) was added as high-shear (HS) polymer along with water to the base paint formulation shown in table 9 A and 9B The dosages of LS, HS polymers and water were adjusted to achieve a target Krebs stormer viscosity of 105*5 KU units and an ICI viscosity of 13G±l(hn.Pa.s.

IQQ22I { Example 20: Serai-gloss Formulation

{00222] In comparative Example 17(c), Aquaflow XLS536 was added as low-shear (LS) polymer and polymer solution Example 17 (c) was added as high-shear (HS) polymer along with water to the base paint formulation shown in table 9 A and 9B. The dosages of LS, HS polymers and water were adjusted to achieve a target Krebs stormer viscosity of 105*5 KU units and an !CI viscosity of 130*10 m.Pa.s.

]00223] Example 21: Semi-gloss Formulation

{00224] In comparative Example! 7(d), Aquaflow XLS530 was adde as low-shear (LS) polymer sad Polymer solution Example 17 (d) was added as high-shear (HS) polymer along with water to the base paint formulation shown in Table 9A and 9B The dosages of LS, HS polymers and water were adjusted to achieve a target: Krebs stormer viscosity of 105*5 KU units and an id viscosity of 130*10 m Pa.$

{00225] Example 22: Semi -gloss Formulation

100220] In comparative Example 17(e) Aquaflow XLS530 was added as low-shear (LS) polymer and polymer solution Example 17 (e) was added along with water to the base paint formulation shown in fable 9A an 9B The dosages of LS, HS and water were adjusted to achieve a target Krebs stormer viscosity of 105*5 KU units and an ICI viscosit of 130*10 m.Pa.s. (QQ227] Example 23: Wet Paint properties

Table 11 : Wet Paint properties

{00228] Example 24: Dry film properties

Table 12: Dry film properties

Methods 00229] Storraer viscosity is measured by a Stormer viscometer as per the standard test method A STM D562 and expressed in Kreb Units (KU).

[00230] ICI viscosity is measured by an ICI cone and plate viscometer as per the standard test method ASTM D4287 expressed in Poise (P).

[00231] Brookfield viscosity is measured on a Brookfield viscometer using spindle 5 at 30RPM.

[00232] Sag resistance is measured on a Leneta chart base on the standard ASTM D4400 using a mid-range bar. Wet film thickness (WFT) in mils above winch sag occurs is measured

[00233] Leveling is measured based on a Leneta chart based on the standard ASTM D4062 method on a scale of 0-10; 0 is worst and 10 is best.

[00234] Gloss is measured using a spectrophotometer at 60° and 80° angles,

[00235] Table 1 1 and Fable 12 gives the wet paint properties and dry film properties of polymer examples of the present disclosure. The results indicate that the polymem from the present disclosure presents good sag/ level balance and gloss properties.

[00236] Table 12: shows the dry film properties of the examples presented in this disclosure. The polymers presente in the present disclosure show higher gloss and good sag/level balance.

[00237] While this invention has been described in detail with reference to certain preferred embodiments, it should be appreciated that the present invention is not limited to those precise embodiments. Rather, in view of the present disclosure, many modifications and variations would present themselves to those skilled in the art without departing from the scope and spirit of this invention.

Claims

What is claimed is:

1. A polymer obtained from a reaction mixture comprising:

(i) at least one dihydroxy lactam moiety; and

(is) at least one functional moiety having a hydroxy 1-reactive functional

P»np;

wherein (i) and (ii) are independently present in amounts of about Q H mole% to about 99.99 moles% and the polymer is selected from a group consisting of polyester, polycarbonate, polyether, poly (ester ether), poly (ester amide), poly imide, polyamide, poly acrylates and poly (ester imide); or wherein each (i) and (ii) is present i amounts of other than 50 mole% and wherein the polymer is a polyurethane.

2. The polymer according to claim .1 , wherein said dihydroxy lactam moiety has a structure:

wherein “R” is independently selected from the group consisting of hydrogen, and functionalised and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the afore mentioned groups can be with or without heteroatoms and linear or branched;

“A” is an alkytene or alkenylene group comprising 2 to 50 carbon atoms; and

wherein 2 to 4 carbon atoms reside in the lactam ring between the

group and the group:

is an integer ranging from I to 6; and“m” is an integer ranging from 0 to 6

3. The polymer according to claim 2, wherein said dihydroxy lactam moiety is selected from the group comprising of:

wherein“/t” is art integer ranging from 1 to 6; and“m” is an integer ranging Iron) 0 to 6,

4. The polymer according to claim 3, wherein said dihydroxy iaetani moiety is selected from the group consisting of -(2_J3-dihydiOxypropyl} 2-py:iTolidone, 1- 2 (2,3· dihydroxypropyk)xy)ethyl]-2-pyrroMone, and a combination thereof.

3, The polymer according to claim 1, wherein the functional moiety is selected from the group consisting of: (a) carbamates, (b) acyl halides, (e) sulfonyl halides, (d) isothiocyanates, (e) cyanoacrylates, (f) isocyanates, (g) oxirars.es, (h) imines, (i) thiocafbonates, (0 thiols, (k) aldehydes, (1) azirktines, (m) acids and their anhydrides, (n) azides, (o) phosphorus halides with alcohols, (p) esters, (q) amines, (r) alkyl halides, (s) dihalogenomethaues and combinations thereof.

6. The polymer according to claim 1 , wherein said ionelionai moiety is selected from the group consisting of:

(a) hydroxyethyl carbamate, hydroxypropyl carbamate, hydroxybotyl carbamate and combinations thereof:

(b) acryioyl chloride, sitcchiyi chloride, meihaetyloyl chloride, eroionoyl chloride, benzoyl chloride, cinna oyl chloride, hydroein mimoyl chloride, acetyl chloride, 2~ acetoxyacetyl chloride, diphenylacetyl chloride, 2-methoxybenxoy! chloride, 3,4,5 trimethoxyhenxoyl chloride, 3,4 (medtyienedtoxy)benzoyl chloride, cyclopropanecarbonyl chloride, pentadecenoyl chloride, 2-cyclohexene- 1 -carbonyl chloride, 2-ihi.opheneacetyl chloride and combinations thereof;

(c) methane sulfonyl chloride, benzenesuifonyi chloride and combinations thereof;

(d) methyl isotliiocyanate, ally! isothiocyanate, aryl isothiocyanates and combinations thereof;

(e) ethyl cyanoacrylate, N-b tyl-cyanoaciylate (NBCA), 2-ocytyl~cyanoacry'late (2- OCA) and combinations thereof;

(f) hexamethylene diisocyanate, toluene diisocyanate (TDI), diphenylriieihane diisocyanate (MDI), m-phenylene diisocyanate, p-phenylene diisocyanate, bitolylene diisocyanate, cyclohexane diisocyanate (CHDI), bis-(i$ocyanatomethyl) cyclohexane (H6XD1), dicyclohexylmethane diisocyanate (H12MDI), dimer acid diisocyanate (DD1), trimethyi hexamethylene diisocyanate, lysine diisocyanate and its methyl ester, isophorone diisocyanate, methyl cyclohexane diisocyanate, 1,5-napthalene diisocyanate, xylylene and xylene diisocyanate and methyl derivatives, polymethylene polypheny! isocyanates, chlorophenyiene-2,4~diisocyanaie, polyphenylene diisocyanate, isophorone diisocyanate (IPP1), hydrogenated methylene diphenyl isocyanate (HMD1), tetramethyl xylene diisocyanate (TMXDl), hexamethylene diisocyanate (HDI), and their respective dimers, trimers and oligomers;

(g) ethylene oxide (BO), propylene oxid (PO) butylene oxide, l-oetene oxide, cyclohexene oxide, styrene oxide, bisphenol A diglycidyl ether, diglycidyl ether, epiehlorohydrin, giycidic acid, ally! glycidyl ether (| 2-propenyloxy)ffiethylj-oxirane), glycidyl (methacrylate, vinylcyclohexene diepoxide, 3,4-epoxyeyclohexylmethyl 3,4- epoxycyclohexane carboxyiate, 3,4-epoxy-6-methylcyclbhexylmethyl 3,4-epoxy-6- meih leyclohexane carboxylate, dipentene dioxide, 2-(3,4-epoxycy£lohexyl-5,5~spiro~3,4~ epaxy)cyetohexane raeta-dioxane, and combinations thereof;

(h) polyaldi mes, hydroxyaldimmes, po!yketimines, hydroxyketi mines, and combination thereof;

(i) s-(pheByithiocarboayIoxymethyi) esters, bis-( isopropylihiocaihonyioxymethyl } esters, and combinations thereof;

(j) glutathione, 3-acetyl- thiol propionic acid, thio anhydride, thio acid, and combinations thereof;

(k) acetaldehyde diethyl acetyl propionaldehyde diethyl acetyl, diCacetaldehyde diethylacetal), c hi oro ace a Sdehyd e diethyl acetal, and combinations thereof;

(l) 2,2-Ms-hydroxymethylhutanol irhv-(3-( I -aziridinyflpropionaie], Ms-N- aziridinomethane, and combination thereof;

(m) maleic acid, maleic anhydride, iumaric acid, citric acid, alkenyl succinic anhydrides,

phihalie anhydride, terephthalic acid, succinic anhydride, tetrahydrophthalic anhydride, maleic anhydride copolymers, and combinations thereof;

(n) azide- functionalized DMA, azide-functionalized peptides, azide-functionalized proteins, azide- functionalized sugars, azide-functionalized metal, azide-ftmctionalized nanoparticles, azide-functionalized antimicrobials, isodiimi 4,4*-diazidostilhene-2,2 - disulfonate, aromatic bisazide compound, calcium azide, 4,4-diphenyidisulfonyl azide and p- toluenesulfonyl azide, an combinations thereof;

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

(p) dimethyl itaconaie, di-n-butyl itaconaie, vinyl hexanoate, glycoiide, s-caprolactone, y-caprolactone, poly(D,L-lactide). poly(D-iactide), poly (L-iactide), polyie-caprolactone), poly (y-caprolactone), polyglycolide, va!erolactone, butralactone, polyether-polyester, poly- anhydride-diol-polyester, and combinations thereof;

(q) amino alcohols, methylamine, efhy!amine, hexylamine, isopropylamine, isobutylaraine, amyla ines, cyclohexyl amine, octylamme, bertzylamme, dimethylamine, dieihylamine, dipropylamine, dibutylamme, diphenyiamine, dibenzyiamine, ethylmethylamine, N~methylamline, ethyleuedhunme, propyleuediamiue, butylenediamine, hexamethyienediamiiie, cyclohexylenediamine, piperazine, toluenediamine, isophoronediamrae, , -dimethylanilme, N,N-dimethyl-l -naphthylamine, N, -dimethyl-p- toluidine, N, -diethylaniliue, N,N-dlallylanilme, 1 -phenylpiperidine, and 4- pheny! morpholine, amino-ethoxylates, cocamine, soyamine and combinations thereof. (r) bromohexaaes, bromododeeane, bramohexadeeane, .1 -bromooctadecane and combinations thereof, and

(s) dibromomethane, dich!oromethane and combinations thereof.

7 The polymer according to claim 1 , wherein the reaction mixture further comprises one or more non-lactam moiety

8. The polymer according to clai 7, wherein said non-iacCam moiety is selected from the group comprising of fnnctionalized/hnfnnetionahzed compounds of aHphade/aromatic alcohols with a carbon chain length of G-Cis„ alkoxylated alcohols with a carbon chain length of CJ-CSS alcohol, ethylene glycols, alcohol meih(aciyiates), polyvinyl alcohols, polycarbonatepolyols, polybaiylene glycols, polyethylene glycol, polypropylene glycols, hydroxypolyestere, hydroxypolyethers, hydroxypolythioesters, hydroxypolyacetais, hydroxy-polycarbonates, polyetherpolyols, polyesterpolyols, polyearbonatepolyols, hydroxypo lyesters , hydroxypolyethers, hydroxypolythioesters, h droxypoly acetal s, hydroxypolycarbonates, aliphatic an aromatic polyether polyols, capro!actone-based polyols, polyethylene gtycol)-soyamine, polyethylene glycol)- castor oil, polyiethy!ene glycol)- hydrogenated castor oil polyethylene glycoll-lanolin, poly (ethylene giycol)-lanolm wax, polyethylene glycol)-polyvinyhdene fluoride, polyethylene giycoi)-poly(vinyl acetate), polyethylene glycoil-polyoxymethylene, po1y(ethylene glycol)-ester, and a combination thereof.

9. The composition according to claim 1 , wherein said polymer has an average molecular weight ranging fro about 3000 g/mol to about 5 ,000,000 g/mol.

10. A polymer obtained from a reaction mixture comprising:

(i) N-(2,3~dihydraxypropyi)-2-py dk1one and/or 1 -[2~(2,3- dihydroxypropy oxy)eihyl |-2-pyjTolidone_> and

(ii) po3y(D, L-tactide);

wherein (i) and (ii) are independently present in amount of about 0.0! mole% to about 99.99 nio!es% and the polymer is a polyester.

1 1. A polymer obtained from a reaction mixture comprising:

(i ) N-(2 ,3-dshydroxypropy l}-2 -pytrolidone and/or 1 ~[2-(2 ,3- dihy<frox propyloxy)ediyl]-2-pym>lidone, and

(ii) a) isophorone diisocyanate, b) polyethylene glycol, and optionally e) ocianol;

wherein each (i) and (ii) is present in amount of other than 50 mole% and the polymer is a polyurethane.

.13. A composition compnsi ngi

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

(i) at least one di ydroxy lactam moiety; and

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

wherein (i) and (ii) are independently present in an amount of about 0,01 moie% to abou t 99.9 moles% and the polymer is selected from a group consisting of polyesters, polyamides, polyCester amides), polyester imides, polycarbonates and polyethers; or

wherein each (i) and (ii) is present in amounts of other than 50 moie% and the polymer is a polyurethane; and

(11) one or more additives.

14 The composition according to claim 13, wherein the additive is useful in an application selected from the group consisting of adhesi ves, aerosols, agricultural agents, anti- soil redeposition agents, batteries agents, beverages, biocides, biomaterials, cementing and construction agents, cleaning agents, paints & coating agents, rheology modifiers, conductive materials, cosmetic agents, dental agents, decorated pigments, detergents, dispersants, drugs, electronics, encapsulations, foods, hair care agents, household-industrial institutional agents, inks and coatings, interlaminate, lithographic solutions, membrane additive agents, metal working fluids, oilfield agents, paper sizing agents, polish, personal care agents, pharmaceuticals, pigment additives, piasters, plastics, textiles, lubricants, printing, refractive index modifiers, sequestrants, soil release agents, static control agents, and wood-care agents.

15. A pharmaceutical composition comprising;

I. a polymer obtained from a reaction mixture comprising (i) N-(2,3- dihydroxypropyl)-2-pytTo!idoiie and/or l-|2-(2,3-dihydroxypropyloxy)ethyl)-2-pyrroiidone; and (ii) pbly(D,1 laclide) wherein (i) and (ii) are independently present in amounts of about 0,01 mok% to about 99 99 moies% and the polymer is a polyester, and

II. one or more pharmaceutically acceptable additives.

16. A pharmaceutical composition according to claim 15, wherei the pharmaceutically acceptable additive is selected from the group comprising of plasticizers, disintegranis, surfactants, lubricants, glidants, carriers, anti-adherents, fillers, wetting agents, pH modifiers, binders, solubility modifiers, recrystail ation. inhibitors, coaling agents, diluents, coloring agents, preservatives, anti foaming agent, antioxidants, buffering agents, acidifying agents, alkalizing agents, complexation-enhancing agent, cryoprotectant, electrolytes, gelling agents, emulsifying agents, solubility-enhancing agents, stabilizers, tonicity modifiers, flavors, sweeteners, completing agents, fragrances, and viscosity modifiers.

17, A coating composition eompri sing;

I. a polymer obtained from a reaction mixture comprising; (i) N~(2,3~ dihydroxypropyl)-2-pyrroIkione and/or l~p~(2,3~dihydroxy^rpropyiox>^>}ethylj-2-pyrrolidone, and. (ii) a) isophorone diisocyanate, b) polyethylene glycol, and optionally c) octanol; wherein each (i) and (ii) present in amount of oilier than 50 mole% and the polymer is a polyurethane, and

II. one or more coating agents. 18, A coating composition according to claim 17, wherein the coating agent is selected from the group comprising of solvenis/coso!vents, secondary rheology modifiers, thixotropic agents, binders, crosslmkers, pH adjustment agents, pigments/fillers, flow-control agents, gloss-control agents, coalesced agents, ilexibiiizlng resins, surfactants, waxes, wetting agents, dispersing agents, plasticizers, antioxidants, UV radiation absorbers, biocides, extenders, colorants, adhesion promoters, defoami g agents/defoaraers, driers, matting agents, and combinations thereof.

19. A process of preparing a polymer comprising;

(A) (i) at least one dihydroxy lacta moiety, and. (ii) at least one functional moiety having a hydroxyl-reactive functional group; wherein (i) and (ii) are independently present in amounts of about 0.01 mole% to about 99.99 rooles% and the polymer is selected from a group consisting of polyester, polycarbonate, poly ether, poly (ester ether), poly (ester amide), poly imide, polyamide, poly acrylates and poly (ester imide); or wherein each (i) and (it) is present in amounts of othe than 50 mole% and the polymer is a polyurethane;

(B) charging (A) into a reaction container under inert gas atmosphere with solvent;

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

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

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

(F) retrieving desired polymer from (E)

20 A process of preparing a polymer comprising:

(A) (i) at least one dihydroxy lactam moiety, and (ii) at least one functional moiety having a hydroxyl-reactive functional group, wherein (i) and (it) independently present in amount of about 0 01 mole% to about 99.99 moles% and the polymer is selected from a group consisting of polyester, polycarbonate, polyether, poly (ester ether), poly (ester amide), poly imide, polyamide, poly acrylates and poly (ester imide); or wherein each (i) and (ii) present in amount of other than 50 moie% and the polymer is a polyurethane;

(B) charging (A) into a reaction container under inert gas atmosphere;

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

(D) charging a additional reactive moiety to (C);

(E) polymerizing (D) with catalyst;

(F) increasing temperature of (E) to 90- P0¾ and maintaining the temperature for about 2-3 hours; and

(G) retrieving desired polymer from (F).