Compatibilizers and their uses

Abstract

A composition comprising a compatibilizer and a drug for use in a wide variety of filled and unfilled liquid matrices is described. The compatibilizer can reduce the viscosity of the matrix and / or improve the stability of the matrix. Exemplary compatibilizers include one or more arylsulfonyl derivatives, such as arylsulfonyl urethanes, arylsulfonylureas, and arylsulfonamides.

Description

[Technical field]

[0001] Claiming priority This application claims the benefit of U.S. Provisional Patent Application No. 63 / 328,476, filed April 7, 2022, the disclosure of which is incorporated by reference in its entirety herein. The presently disclosed subject matter relates to compatibilizers for use in a variety of applications to enhance the stability and / or reduce the viscosity of filled and unfilled resins or other liquid-based compositions, etc. Exemplary compatibilizers of the presently disclosed subject matter include compounds that include arylsulfonyl derivatives, e.g., urethane, urea, and amide derivatives of arylsulfonyl groups. [Background technology]

[0002] Filled polymer systems have many uses, such as in applications involving thermal or electrical conductivity. For example, electronic components generate heat during use, and removal of this heat can help prevent thermal decomposition of the components and improve or maintain their operating efficiency. Thus, microelectronic components (e.g., integrated circuits) often use thermally conductive fillers, such as greases, gels, or adhesives that contain micro- and nanoparticles of boron nitride, aluminum nitride, zinc oxide, silicon carbide, and alumina, to remove heat from the components.

[0003] The properties of filled polymer systems can be related not only to the type of polymer matrix and / or filler used, but also to the amount of filler in the material. In general, the more filler added, the higher the viscosity of the resulting material. Thus, the balance between maintaining a workable viscosity and achieving a particularly desirable property (e.g., electrical or thermal conductivity) with a high filler loading is often a trade-off. Many filled polymer systems are dispersed using a syringe, and therefore it may be desirable to maintain a viscosity low enough to allow flow through a needle. In addition, settling of particles (e.g., micron-sized particles), such as encapsulants, gap fillers, and those used to enhance the thermal conductivity of adhesives, can be an issue that can limit the commercial success of such materials. Settling can occur during storage and shipping of the material, and for certain adhesive chemistries, such as epoxies or urethanes, can be exacerbated by heat. The result is a material containing a non-uniform distribution of fillers that can be difficult to rehomogenize before use and / or can settle rapidly during use. Mixtures containing different immiscible or partially miscible liquid molecules or macromolecules (e.g., polymer blends, polymer resins, oil-in-water or water-in-oil compositions) may also have stability, homogeneity, and / or viscosity problems that can adversely affect the properties and / or ease of use of the mixture. Thus, there is a continuing need for agents that can improve the stability, homogeneity, and / or viscosity of liquid-based compositions, including liquid-based compositions that contain solid organic and / or inorganic fillers. Summary of the Invention

[0004] This Summary lists several embodiments of the subject matter of the present disclosure, and often lists variations and permutations of these embodiments. This Summary is merely one example of numerous and varied embodiments. Reference to one or more representative features of a given embodiment is also for illustrative purposes. Such embodiments can typically exist with or without the features mentioned, and similarly, those features can be applied to other embodiments of the subject matter of the present disclosure, whether or not they are listed in this Summary. This Summary does not list or suggest all possible combinations of such features, in order to avoid excessive repetition.

[0005] In some embodiments, the presently disclosed subject matter provides a composition that includes: (a) a liquid matrix; (b) a compatibilizer that includes (b1) one or more first groups, wherein the one or more first groups each include an arylsulfonyl moiety; and (b2) one or more second groups, wherein the one or more second groups each include an alkyl moiety, a polymeric or oligomeric moiety, or a combination thereof, wherein each of the one or more second groups is bonded to at least one of the one or more first groups; and (c) one or more optional additional components. In some embodiments, the presently disclosed subject matter provides a method of modifying the viscosity of a polymer resin composition comprising contacting a composition comprising a polymer resin with a compatibilizer, the compatibilizer comprising: (b1) one or more first groups, wherein the one or more first groups each comprise an arylsulfonyl moiety; and (b2) one or more second groups, wherein the one or more second groups each comprise an alkyl group, a polymeric or oligomeric group, or a combination thereof, wherein each of the one or more second groups is bonded to at least one of the one or more first groups.

[0006] In some embodiments, the presently disclosed subject matter provides a method of preparing a polyurethane comprising contacting a composition comprising a polyol and / or an isocyanate resin with a compatibilizer, the compatibilizer comprising: (b1) one or more first groups, wherein the one or more first groups each comprise an arylsulfonyl moiety; and (b2) one or more second groups, wherein the one or more second groups each comprise an alkyl moiety, a polymeric or oligomeric moiety, or a combination thereof, wherein each of the one or more second groups is bonded to at least one of the one or more first groups.

[0007] In some embodiments, the subject matter of the present disclosure is a compound represented by formula (I)-(V): A1-X1-Z1(I), A1-X1-Z2-X2-A1(II), Z1-X2-A2-X1-Z1(III), A1-(X1-Z2-X2-A2) n -X1-Z2-X2-A1(IV), and (A1-X1) p -Z3(V) [wherein n is an integer of 1 or greater, p is an integer of 3 or greater, each A1 is aryl or substituted aryl, each A2 is arylene or substituted arylene, each X1 is -S(=O)2-NH-C(=O)-Q- or -S(=O)2-NH-C(=O)-, each X2 is -Q-(C=O)-NH-S(=O)2- or -C(=O)-NH-S(=O)2-, each Q is O or NH, Z1 is alkyl and -(L2) s -(L3) t -R1, s is 0 or 1, t is 0 or 1, L2 is an alkylene, L3 is a polymeric or oligomeric moiety, R1 is an alkyl or silyl, Z2 is an alkylene, a polymeric or oligomeric moiety, or a combination thereof, and Z3 is a multivalent radical derived from a compound containing at least three hydroxy, amino, or carboxylic acid groups. It is therefore an object of the presently disclosed subject matter to provide compatibilizers comprising arylsulfonyl moieties, compositions comprising pharmaceutical agents, and related methods. These and other objects are achieved, in whole or in part, by the presently disclosed subject matter. Other objects and advantages of the presently disclosed subject matter will become apparent to those skilled in the art after studying the following description, figures, and examples.

[0008] The subject matter of the present disclosure can be better understood by reference to the following exemplary figures. The components of the figures are not necessarily to scale, with emphasis instead being placed on illustrating (often in a schematic manner) the principles of the subject matter of the present disclosure. A further understanding of the subject matter of the present disclosure can be obtained by reference to the embodiments described in the accompanying figure description. The illustrated embodiments are intended merely to illustrate a system for carrying out the subject matter of the present disclosure, but both the organization and the method of operation of the subject matter of the present disclosure, together with further objects and advantages thereof, in general, may be more readily understood by reference to the figures and the following description. The figures are not intended to limit the scope of the subject matter of the present disclosure, which is described with particularity in the appended or subsequently amended claims, but are intended merely to clarify and provide examples of the subject matter of the present disclosure. For a more complete understanding of the subject matter of this disclosure, reference is now made to the following figures. [Brief description of the drawings]

[0009] [Figure 1A-1D] FIG. 1A is a schematic diagram illustrating the synthesis of three exemplary arylsulfonyl derivative compatibilizers of the presently disclosed subject matter formed from the reaction of para-toluenesulfonyl isocyanate (PTSI) with different monofunctional alcohols: monobutyl polypropylene glycol (mPPG, FIG. 1A), isostearyl alcohol (ISA, FIG. 1B), polyethylene glycol oleyl ether (PEGOE, FIG. 1C), or monocarbinol-terminated polydimethylsiloxane (PDMS, FIG. 1D). [Diagram 2] FIG. 2 is a schematic diagram showing the chemical structure of an exemplary "first" or "head" group of a compatibilizer of the present disclosure. [Diagram 3]1 is a schematic diagram showing different exemplary configurations of compatibilizers of the present disclosure, where the "first" group of the agent is indicated by a circle or the letter "B" and the "second" group is indicated by a wavy line or the letter "A." [Figure 4] 1 is a graph showing the effect of the amount of compatibilizer (measured in mass percent (wt%) of the total organic content in the formulation) on the viscosity (measured in Pascal seconds (Pa-sec) at a shear rate of 0.5 seconds per second (s-1)) of a polypropylene glycol (PPG) resin highly filled (79 wt%) with aluminum trihydride particles (ATH). The compatibilizer is a subject of the present disclosure formed from the reaction of para-toluenesulfonyl isocyanate (PSTI) and monobutyl polypropylene glycol (mPPG). [Diagram 5] 1 is a graph showing the effect of shear rate (measured in Pascal seconds (Pa-sec)) on the viscosity (measured in s-1) of a polypropylene glycol (PPG) resin highly filled (79 weight percent (wt%)) with aluminum trihydroxide particles (ATH). Data is shown for formulations containing 0.41 wt. % of the compatibilizer of the presently disclosed subject matter as described in Example 1 (closed triangles), Example 3 (open squares), Example 4 (open circles), or Example 5 (closed squares). For comparison, data is also provided for formulations not containing the compatibilizer of the presently disclosed subject matter (closed circles). [Figure 6] 1 is a graph showing the effect of shear rate (measured in Pascal seconds (Pa-sec)) on the viscosity (measured in s-1) of a hydrogenated methylene bis(phenyl diisocyanate) (hydrogenated MDI) resin highly filled (79 weight percent (wt%)) with aluminum trihydroxide particles (ATH). Data is shown for a formulation containing 0.41 wt% of the compatibilizer of Example 6 (open circles) and the same formulation without the compatibilizer of the presently disclosed subject matter (closed circles). [Figure 7]1 is a graph showing the effect of shear rate (measured in Pascal seconds (Pa-sec)) on the viscosity (measured in s-1) of a polyalphaolefin (PAO) fluid highly loaded with iron particles (78.1 weight percent (wt%)). Data is shown for a formulation containing 0.6 wt% of the compatibilizer of Example 6 (open circles) and the same formulation without the compatibilizer of the presently disclosed subject matter (closed circles). [Figure 8] 1 is a graph showing the effect of shear rate (measured in Pascal seconds (Pa-sec)) on the viscosity (measured in s-1) of vinyl-terminated polydimethylsiloxane (PDMS) highly loaded (84.1 weight percent (wt%)) with aluminum trihydroxide (ATH) particles. Data is shown for a formulation containing 0.32 wt% of the compatibilizer of Example 7 (open circles) and the same formulation without the compatibilizer of the presently disclosed subject matter (closed circles). DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0010] The subject matter of the present disclosure is described more fully below, but below are descriptions of some, but not all, embodiments of the subject matter of the present disclosure. Indeed, the subject matter of the present disclosure may be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will satisfy applicable legal requirements.

[0011] I. Definition The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the subject matter of the present disclosure. Although the following terms are believed to be well understood by those of ordinary skill in the art, the following definitions are set forth in order to facilitate description of the subject matter of the present disclosure. All technical and scientific terms used herein are intended to have the same meaning as commonly understood by those skilled in the art, unless otherwise defined below. References to techniques used herein are intended to refer to techniques commonly understood in the art, including modifications of those techniques that would be obvious to those skilled in the art, or equivalent replacements. Although the following terms are believed to be well understood by those skilled in the art, the following definitions are provided to facilitate the description of the subject matter of the present disclosure.

[0012] In describing the subject matter of this disclosure, it will be understood that several techniques and steps are disclosed, each of which has individual benefits and each of which can also be used in conjunction with one or more, or in some cases all, of the other techniques disclosed. Thus, for the sake of clarity, this specification refrains from repeating every possible combination of the individual steps in an unnecessary manner, but the specification and claims should nevertheless be read with the understanding that such combinations are fully within the scope of the invention and claims.

[0013] Following long-standing patent law convention, the terms "a," "an," and "the" when used in this application, including the claims, refer to "one or more." Thus, for example, a reference to "a cell" includes a plurality of such cells, and so forth. Unless otherwise indicated, all numbers expressing quantities of ingredients, reaction conditions, and so forth used in the specification and claims are to be understood as being modified in all instances by the term "about." Accordingly, unless indicated to the contrary, the numerical parameters set forth in the specification and appended claims are approximations that may vary depending upon the desired properties sought to be obtained by the presently disclosed subject matter. As used herein, the term "about" when referring to a value or amount, such as composition, dosage, sequence homology (e.g., when comparing two or more nucleotide or amino acid sequences), mass, weight, temperature, time, volume, concentration, percentage, and the like, is meant to encompass variations of, in some embodiments, ±20%, in some embodiments, ±10%, in some embodiments, ±5%, in some embodiments, ±1%, in some embodiments, ±0.5%, and in some embodiments, ±0.1% from the specified amount, as such variations are appropriate for performing the disclosed methods or using the disclosed compositions.

[0014] The term "comprising" is synonymous with "including," "containing," or "characterized by" and is inclusive or open-ended and does not exclude additional, unrecited elements or method steps. "Comprising" is a term of the art used in claim language to mean that the named elements are essential, but that other elements can be added and still form a construct within the scope of the claim.

[0015] As used herein, the phrase "consisting of" excludes any element, step, or ingredient not specified in the claim. When the phrase "consisting of" appears in a clause in the body of a claim rather than immediately following a preamble, it limits only the elements recited in that clause and does not exclude other elements from the claim as a whole. As used herein, the phrase "consisting essentially of" limits the scope of a claim to those materials or steps specified in addition to those that do not materially affect the basic and novel characteristic(s) of the claimed subject matter. With respect to the terms "comprising," "consisting of," and "consisting essentially of," when one of these three terms is used herein, the subject matter disclosed and claimed herein may include the use of either of the other two terms. As used herein, the term "and / or," when used in the context of a listing of entities, refers to the entities present either singly or in combination. Thus, for example, the phrase "A, B, C, and / or D" includes A, B, C, and D individually, but also any and all combinations and subcombinations of A, B, C, and D.

[0016] As used herein, the term "alkyl" refers to any alkyl group having an alkyl group up to and including both ends, including, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, octyl, ethenyl, propenyl, butenyl, pentenyl, hexenyl, octenyl, butadienyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, and arenyl groups. 1-40 "Branched" can refer to an alkyl group having a lower alkyl group, such as methyl, ethyl, or propyl, attached to a linear alkyl chain. "Lower alkyl" refers to an alkyl group having from 1 to about 8 carbon atoms (i.e., C 1-8 "Alkyl" refers to an alkyl group having, for example, 1, 2, 3, 4, 5, 6, 7, or 8 carbon atoms, or up to about 5 carbon atoms. "Higher alkyl" refers to an alkyl group having from about 10 to about 40 carbon atoms, for example, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, or 40 carbon atoms. In certain embodiments, "alkyl" refers to an alkyl group having, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, or 40 carbon atoms. 1-8 In another embodiment, "alkyl" refers to a straight chain alkyl, particularly C 1-8 Refers to branched chain alkyl.

[0017] An alkyl group may be substituted with one or more alkyl group substituents, which may be the same or different ("substituted alkyl"). The term "alkyl group substituent" includes, but is not limited to, alkyl, substituted alkyl, halo, arylamino, acyl, hydroxyl, aryloxyl, alkoxyl, alkylthio, arylthio, aralkyloxyl, aralkylthio, carboxyl, alkoxycarbonyl, oxo, and cycloalkyl. In some embodiments, one or more oxygen, sulfur, or substituted or unsubstituted nitrogen atoms may be inserted along the alkyl chain, and the nitrogen substituent is hydrogen, lower alkyl (also referred to herein as "alkylaminoalkyl"), or aryl. Thus, as used herein, the term "substituted alkyl" includes alkyl groups, as defined herein, in which one or more atoms or functional groups of the alkyl group have been replaced with another atom or functional group, including, for example, alkyl, substituted alkyl, halogen, aryl, substituted aryl, alkoxyl, hydroxyl, nitro, amino, alkylamino, dialkylamino, sulfate, and mercapto.

[0018] The term "aryl" is used herein to refer to an aromatic substituent, which may be a single aromatic ring or may be multiple aromatic rings fused together, covalently linked, or linked to a common group, such as, but not limited to, a methylene or ethylene moiety. The common linking group may also be a carbonyl, such as in benzophenone, or an oxygen, such as in diphenyl ether, or a nitrogen, such as in diphenylamine. The term "aryl" specifically encompasses heteroaromatic compounds. The aromatic ring(s) may include phenyl, naphthyl, biphenyl, diphenyl ether, diphenylamine, and benzophenone, among others. In certain embodiments, the term "aryl" refers to a cyclic aromatic containing about 5 to about 10 carbon atoms, e.g., 5, 6, 7, 8, 9, or 10 carbon atoms, including 5- and 6-membered hydrocarbon and heteroaromatic rings.

[0019] Aryl groups can be optionally substituted with one or more aryl group substituents, which can be the same or different ("substituted aryl"); "aryl group substituents" include alkyl, substituted alkyl, aryl, substituted aryl, aralkyl, hydroxyl, alkoxyl, aryloxyl, aralkyloxyl, carboxyl, acyl, halo, nitro, alkoxycarbonyl, aryloxycarbonyl, aralkoxycarbonyl, acyloxyl, acylamino, aroylamino, carbamoyl, alkylcarbamoyl, dialkylcarbamoyl, arylthio, alkylthio, alkylene, and -NR'R", where R' and R" can each independently be hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, and aralkyl. Thus, as used herein, the term "substituted aryl" includes aryl groups, as defined herein, in which one or more atoms or functional groups of the aryl group have been replaced with another atom or functional group, including, for example, alkyl, substituted alkyl, halogen, aryl, substituted aryl, alkoxyl, hydroxyl, nitro, amino, alkylamino, dialkylamino, sulfate, and mercapto.

[0020] Specific examples of aryl groups include, but are not limited to, cyclopentadienyl, phenyl, furan, thiophene, pyrrole, pyran, pyridine, imidazole, benzimidazole, isothiazole, isoxazole, pyrazole, pyrazine, triazine, pyrimidine, quinoline, isoquinoline, indole, carbazole, and the like. "Heteroaryl," as used herein, refers to an aryl group that contains one or more non-carbon atoms (e.g., O, N, S, Se, etc.) in the backbone of the ring structure. Nitrogen-containing heteroaryl moieties include, but are not limited to, pyridine, imidazole, benzimidazole, pyrazole, pyrazine, triazine, pyrimidine, etc.

[0021] The term "monovalent," as used herein, refers to the radical of a named chemical group that has one site of attachment to another chemical group. The term "divalent," as used herein, refers to a diradical of a named chemical group that is bonded to two other chemical groups. Thus, for example, a "divalent" group can act as a linking group between two other chemical functional groups.

[0022] "Alkylene" refers to a linear or branched divalent aliphatic hydrocarbon group having 1 to about 20 carbon atoms, e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 carbon atoms. The alkylene group may be linear, branched, or cyclic. The alkylene group may also be unsaturated and / or substituted with one or more "alkyl group substituents." One or more oxygen, sulfur, or substituted or unsubstituted nitrogen atoms may be inserted along the alkylene group (also referred to herein as "alkylaminoalkyl"), where the nitrogen substituent is alkyl as previously described. Exemplary alkylene groups include methylene (-CH2-), ethylene (-CH2-CH2-), propylene (-(CH2)3-), cyclohexylene (-CH6 ... 10 -), -CH=CH-CH=CH-, -CH=CH-CH2-, -(CH2) q -N(R)-(CH2) r - (each of q and r is independently an integer from 0 to about 20, e.g., 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20, and R is hydrogen or lower alkyl, methylenedioxyl (-O-CH2-O-), and ethylenedioxyl (-O-(CH2)2-O-). The alkylene group can have from about 2 to about 3 carbon atoms, and can further have from 6 to 20 carbons.

[0023] "Arylene" refers to a divalent aromatic group. "Aralkyl" refers to an aryl-alkyl group in which the aryl and alkyl are as previously described, and may include substituted aryl and substituted alkyl. Exemplary aralkyl groups include benzyl, phenylethyl, and naphthylmethyl. "Aralkylene" refers to a divalent group containing both arylene and alkylene moieties. As used herein, the term "acyl" refers to a carboxylic acid group in which the -OH of the carboxylic acid group has been replaced with another substituent. Thus, an acyl group can be represented by RC(=O)-, where R is H, alkyl, substituted alkyl, aralkyl, substituted aralkyl, aryl, or substituted aryl as defined herein. Specific examples of acyl groups include formyl (i.e., -C(=O)H), acetyl, and benzoyl.

[0024] The terms "hydroxyl" and "hydroxyl" refer to the -OH group. The term "polyol" refers to a compound that contains two or more or three or more hydroxy groups. The term "phenol" as used herein can refer to a compound of the formula R-OH, where R is aryl or substituted aryl. Thus, the term "phenolic" refers to a hydroxy group that is directly attached to an aromatic group, such as a phenyl ring, naphthyl ring, and the like. The term "alkoxy" refers to the group --OR, where R is alkyl or substituted alkyl.

[0025] The term "aryloxy" refers to the group -OR, where R is aryl or substituted aryl. The term "mercapto" or "thiol" refers to a -SH group. The term "carboxyl" refers to a -C(=O)- group. The terms "carboxylate" and "carboxylic acid" refer to the radical -C(=O)O - and -C(=O)OH groups. In some embodiments, "carboxylate" can refer to -C(=O)O - or a -C(=O)OH group. The terms "amide" and "amido" can refer to the -C(=O)-NR1R2 group, where R1 and R2 are independently H, alkyl, substituted alkyl, aralkyl, substituted aralkyl, aryl, or substituted aryl. Polyamides can include -C(=O)-NR1- linkages in the polymer chain. The terms "carbamate" and "urethane" refer to the group -OC(=O)-NR-, where R is H, alkyl, substituted alkyl, aralkyl, substituted aralkyl, aryl, or substituted aryl.

[0026] The term "urea" refers to the group -NR1-C(=O)-NR1-, where each R1 is independently H, alkyl, substituted alkyl, aralkyl, substituted aralkyl, aryl, or substituted aryl.

[0027] The term "ester" refers to a compound containing a -C(=O)-OR group, where R is alkyl, aralkyl, or aryl. A polyester can contain -C(=O)-O- linkages in the polymer chain. Thus, the term "polyester" can refer to a polymer that contains ester bonds in the polymer backbone. The term "ether" refers to a compound that contains the group -ROR-, where each R is alkylene or arylene. The terms "epoxy," "epoxide," and "oxirane," as used herein, refer to a chemical functional group that includes a three-membered ring structure that contains one oxygen atom and two carbon atoms bonded together through a single bond. Thus, an epoxy group has the structure

[0028] [ka] may have the following structure: The term "arylsulfonyl" as used herein refers to an aryl-S(=O)2- group, where the aryl may be substituted with one or more aryl group substituents. The term "arylsulfonyl derivative" as used herein can refer to a compound or group in which another chemical functional group (e.g., amide, urea, urethane, oxo group, etc.) is bonded directly to the sulfur atom of the arylsulfonyl group. The term "silyl" refers to a group that contains a silicon atom (Si). For example, a silyl group can have the formula -Si(R)3, where each R is selected from H, alkyl, aralkyl, and aryl. An exemplary silyl group is a trialkylsilyl group, such as trimethylsilyl.

[0029] As used herein, the terms "siloxy" and "silyl ether" refer to a group or compound containing a silicon-oxygen (Si-OR) bond, where R is an organic group, such as a substituted or unsubstituted alkyl or aryl group (i.e., methyl, ethyl, phenyl, etc.). In some embodiments, the terms refer to a compound containing 1, 2, 3, or 4 alkoxy, aralkoxy, or aryloxy groups bonded to a silicon atom. Each alkyloxy, aralkoxy, or aryloxy group can be the same or different. The term "polysiloxane" refers to a polymer that includes a backbone with alternating silicon and oxygen atoms, where the silicon atoms are substituted with functional groups such as alkyl, aralkyl, or aryl groups.

[0030] As used herein, the terms "microparticle" and "nanoparticle" have the meanings that may be ascribed to them by those of skill in the art. In some embodiments, a "microparticle" can refer to a particle having a dimension (e.g., width or diameter) ranging from as low as about 1000 μm to about 0.1 μm. In some embodiments, a microparticle has a dimension ranging from about 100 μm to about 1 μm. In some embodiments, a "nanoparticle" refers to a particle having a dimension ranging from about 1 μm to about 0.1 nm. In some embodiments, a nanoparticle has a dimension ranging from about 500 nm to about 1 nm. In some embodiments, a nanoparticle has a dimension smaller than about 200 nm, such as, but not limited to, about 100 nm. Microparticles and nanoparticles can be of any shape, such as cubic, spherical, or irregularly shaped.

[0031] As used herein, "monomer" or "polymerizable monomer" refers to a molecule that can undergo polymerization, thereby contributing a building block, i.e., a repeating atom or group of atoms, to the requisite structure of a polymer or oligomer. As used herein, "polymer" refers to a molecule that includes multiple repeats of units derived from molecules of lower relative molecular weight, e.g., polymerizable monomers and / or oligomers. In some embodiments, a polymer has at least 10, at least 50, or at least 100 repeat units. "Oligomer" refers to a polymeric molecule of moderate relative molecular weight whose structure includes a small number (eg, 2-10) of units derived from molecules of lower relative molecular weight.

[0032] "Copolymer" refers to a polymer derived from two or more types of polymerizable monomers. Copolymers include block copolymers (containing oligomeric or polymeric chains, each chain being an oligomeric or polymeric chain based on a different monomeric unit), random copolymers (monomer units from different monomers are randomly ordered in the copolymer), and statistical copolymers (monomer units from different monomers are statistically distributed in the copolymer chain). A polymer blend refers to a mixture of two different polymers or copolymers. "Chain" refers to all or a portion of a polymer or oligomer that includes a linear or branched arrangement of constitutional units between two boundary constitutional units, which may include end groups, branch points, or combinations thereof. "Main chain" or "backbone" refers to the chain from which all other chains are considered pendant. "Side chain" refers to a smaller chain that is attached to the main chain. In some embodiments, the side chain may contain a single non-repeating constitutional unit.

[0033] The terms "resin" and "polymer resin" as used herein refer to both reactive and non-reactive resins. For example, the term resin can refer to a composition comprising a monomer, oligomer, polymer, or mixture thereof that can be transformed, for example, via a curing or curing process to form a harder polymer matrix. A resin can include a viscous material or a mixture of viscous materials. Additionally or alternatively, a resin can include one or more compounds that can be dissolved in another resin component or solvent that can be evaporated or otherwise removed during and / or after the curing or curing process. Thus, in some embodiments, the term resin refers to a composition that includes a polymerizable monomer that is liquid or can be dissolved in a suitable solvent at a suitable temperature and / or pressure (e.g., room temperature and atmospheric pressure) to develop the resin prior to curing or curing. The term resin can also refer to oligomers and / or polymers that can undergo crosslinking reactions and / or further polymerization to form higher molecular weight compounds. The term resin can also refer to non-reactive resins that cannot form covalent bonds by polymerization or crosslinking. Such non-reactive resins can include one or more oligomeric or polymeric species.

[0034] The term "organic solvent", as used herein, is typically used in the field of organic synthesis and can refer to both polar and non-polar aprotic solvents containing one or more carbon atoms. The term "aprotic solvent" refers to a solvent molecule that cannot accept or donate a proton. Examples of aprotic solvents include, but are not limited to, ethyl acetate; carbon disulfides; ethers, such as diethyl ether, tetrahydrofuran (THF), ethylene glycol dimethyl ether, dibutyl ether, diphenyl ether, MTBE, etc.; aliphatic hydrocarbons, such as hexane, pentane, cyclohexane, etc.; aromatic hydrocarbons, such as benzene, toluene, naphthalene, anisole, xylene, mesitylene, etc.; and symmetric halogenated hydrocarbons, such as carbon tetrachloride, tetrachloroethane, and dichloromethane. Additional aprotic solvents include, for example, acetone, acetonitrile, butanone, butyronitrile, chlorobenzene, chloroform, 1,2-dichloroethane, dimethylacetamide, N,N-dimethylformamide (DMF), dimethylsulfoxide (DMSO), and 1,4-dioxane.

[0035] II. Representative Embodiments In some embodiments, the subject matter of the present disclosure provides a family of compounds that can be used as compatibilizers in a wide variety of applications. For example, the compounds of the present disclosure can be used as surfactants, emulsifiers, foaming agents, adhesion promoters, wetting agents, and / or dispersants. In some embodiments, the compounds of the present disclosure can be used to modify the viscosity of liquid mixtures and / or suspensions, such as paints, coatings, inks, cleaning solutions, cosmetic fluids or emollients, lubricants (e.g., high temperature lubricants, compressor lubricants, refrigeration lubricants, machine lubricants, two-cycle lubricants, rubber lubricants, mill and calendar lubricants, grease and solid lubricants, textile fiber lubricants, textile machine lubricants, etc.), magneto rheological fluids, adhesives, or drilling fluids, among others. In some embodiments, the compounds can be used to modify the coefficient of friction (COF) of liquids and solids.

[0036] In the exemplary embodiments described herein, the compatibilizers of the presently disclosed subject matter can be used to improve the stability and / or reduce the viscosity of filled polyol and / or isocyanate resin systems, such as resin systems for the preparation of highly filled thermally conductive urethanes. In addition to improving viscosity reduction compared to surfactants typically used in such systems, the compatibilizers of the present disclosure can also improve the shelf life and curing stability of the urethane, and provide for the use of higher concentrations of fillers, including lower cost fillers and / or fillers with higher surface areas. However, the agents of the present disclosure are not limited to use in filled polymer matrices, but can also be used in unfilled polymer systems and non-polymer liquid matrices.

[0037] In some embodiments, the compatibilizer of the present disclosure can be the reaction product of (i) an amine, an alcohol, or a carboxylic acid, and (ii) an aryl isocyanate (e.g., para-toluenesulfonyl isocyanate (PTI)) or an arylsulfonyl isocyanate (e.g., para-toluenesulfonyl isocyanate (PTSI). Thus, for example, the compatibilizer can include one or more first groups, the one or more first groups being an arylsulfonyluethane (i.e., a group having the formula aryl-S(=O)2-NH-C(=O)-O-), Arylsulfonylureas (i.e., a group having the formula aryl-S(=O)2-NH-C(=O)-NH-), arylsulfonylamides (i.e., a group having the formula aryl-S(=O)2-NH-C(=O)-), arylsulfonamides (i.e., a group having the formula aryl-S(=O)2-NH-), arylsulfonates (i.e., a group having the formula aryl-S(=O)2-O-), and arylurethanes (i.e., a group having the formula aryl-NH-C(=O)-O-), and arylureas (i.e., a group having the formula aryl-NH-C(=O 1A-1D show synthetic schemes for the synthesis of exemplary compatibilizers of the presently disclosed subject matter prepared from the reaction of PTSI with different mono-alcohols (or "monols"). In some embodiments, PTSI and monools (or other alcohols) can be contacted together under conditions that result in a ratio of isocyanate (NCO) equivalents to hydroxyl equivalents (OH) of about 0.5:1 NCO:OH to about 1.5:1 NCO:OH to form the compatibilizer. For example, in some embodiments, more than OH equivalents are present. A higher NCO equivalent weight can be used to offset possible reactions of NCO groups with residual water that may be present in the monol. In some embodiments, the NCO:OH ratio can be about 1:1. If the aryl isocyanate is reacted with an amine or carboxylic acid instead of an alcohol, a ratio of about 0.5:1 NCO:reactive group to about 1.5:1 NCO:reactive group can be used. Figure 2 shows the general chemical structure of the compatibilizer of the presently disclosed subject matter, showing different types of first functional groups when the aryl group is a methyl-substituted phenyl.

[0038] More generally, the compounds of the present disclosure may include one or more "first" or "head" groups and one or more "second" or "tail" groups, with each of the one or more second groups being bound to at least one or one or more first groups. The one or more first groups may provide for interaction of the compatibilizer with a polar surface (e.g., a polar surface of an inorganic filler particle) or polar group in the liquid. For example, in some embodiments, the first group may interact with the inorganic filler particle through a π bond between a metal ion in the inorganic filler and an aryl portion of the first group, and / or through hydrogen bonding and / or dipole interactions between the inorganic filler and a heteroatom of the first group. The one or more second groups may be selected based on the intended use of the compatibilizer. For example, in some embodiments, the chemistry of the second group can be adjusted to have a similar chemistry to or be otherwise compatible with one or more components of the liquid matrix in which the compatibilizing group is to be used, for example, to enhance the interaction of the compatibilizing agent with the liquid matrix. In some embodiments, the one or more second groups can include an alkyl group (e.g., an alkyl group derived from a fatty acid or fatty alcohol), a polymeric or oligomeric group, or any combination thereof. In some embodiments, the polymer portion of the second group is selected from polyethers, polysiloxanes, polyacrylates, polyesters, and polyolefins.

[0039] The first and second groups of the compatibilizers of the present disclosure can be provided in a variety of different configurations. Exemplary configurations of the first group (B) and second group (A) are shown in FIG. 3. For example, the drug may be provided with one first group and one second group ("AB configuration" in FIG. 3), two second groups bonded to the same first group ("ABA configuration" in FIG. 3), two first groups bonded to the same second group ("BAB configuration" in FIG. 3), an alternating series of first and second groups (e.g., "(BA) nThe gemini-configured compatibilizers of the presently disclosed subject matter can include linkage chemistries and configurations similar to those of gemini surfactants known in the art. See, e.g., Sekhon, BS (Resonance, 42-49 (2004)).

[0040] In some embodiments, the compatibilizer comprises one or more first groups each comprising a moiety that comprises an arylsulfonyl derivative. Thus, in some embodiments, the one or more first groups each comprise an arylsulfonylurea, an arylsulfonylamide, an arylsulfonamide, or an arylsulfonate. In some embodiments, the compatibilizer comprises one or more first groups each comprising a moiety that comprises an arylsulfonyl derivative. Thus, in some embodiments, the one or more first groups each comprise an arylsulfonylurea, an arylsulfonylamide, an arylsulfonate, or an arylsulfonate. In some embodiments, the compatibilizer comprises one or more first groups each comprising a moiety that comprises an arylsulfonyl derivative. A1-X1-Z1(I), A1-X1-Z2-X2-A1(II), Z1-X2-A2-X1-Z1(III), A1-(X1-Z2-X2-A2) n -X1-Z2-X2-A1(IV), (A1-X1) p -Z3(V) It is a compound having one of the structures: [wherein n is an integer of 1 or greater, p is an integer of 3 or greater, each A1 is aryl or substituted aryl (e.g., phenyl or substituted phenyl), each A2 is arylene or substituted arylene (e.g., phenylene or substituted phenylene), each X1 is -S(=O)2-NH-C(=O)-Q- or -S(=O)2-NH-C(=O)-, each X2 is -Q-(C=O)-NH-S(=O)2- or -C(=O)-NH-S(=O)2-, each Q is O or NH, Z1 is alkyl (e.g., branched or straight chain C6-C40 alkyl) and -(L2) s -(L3) t-R1, s is 0 or 1, t is 0 or 1, L2 is an alkylene, L3 is a polymeric or oligomeric moiety, R1 is an alkyl or silyl, Z2 is an alkylene, a polymeric moiety, or a combination thereof, and Z3 is a polyvalent group derived from a compound containing at least three hydroxy, amino, or carboxylic acid groups (i.e., a polyvalent group formed when at least three hydroxy, amino, or carboxylic acid groups of a parent compound react with a sulfonyl isocyanate group to form an X1 linkage).

[0041] In some embodiments, the compatibilizer can be prepared by reacting an arylsulfonyl isocyanate or an aryl di-sulfonyl isocyanate with a monofunctional alcohol (i.e., a "monol"), an amine, or a polyol. For example, in some embodiments, the compatibilizer can be prepared by reacting an arylsulfonyl isocyanate (e.g., PTSI) with a polyol, such as polyoxyethylene (POE) sorbitan monooleate or another sugar derivative, and the compatibilizer can have the structure of formula (V): (A1-X1) p -Z3(V) wherein each A1 is aryl or substituted aryl, each X1 is -S(=O)2-NH-C(=O)-O-, p is an integer equal to or greater than 3, and Z3 is a polyvalent derivative of a polyol (i.e., a polyol derivative in which at least three hydroxy groups of the parent polyol have reacted with sulfonyl isocyanate groups to form X1 linkages and the oxygen atoms of the hydroxy groups of the parent polyol are oxygen atoms bonded to the carboxyl groups of the X1 linkages).

[0042] In some embodiments, the compatibilizer comprises one first group and one second group and is a compound of formula (I): A1-X1-Z1(I) [In the formula, A1 is aryl or substituted aryl, X1 is -S(=O)2-NH-C(=O)-O-, -S(=O)2-NH-C(=O)-NH-, or -S(=O)2-NH-C(=O)-, Z1 is alkyl and -(L2) s -(L3) t -R1, s is 0 or 1, t is 0 or 1, L2 is alkylene, L3 is a polymeric or oligomeric moiety, and R1 is alkyl or silyl. In some embodiments, A1 is phenyl or substituted phenyl (e.g., alkyl substituted phenyl). In some embodiments, A1 is methyl substituted phenyl. In some embodiments, the compatibilizer is the reaction product of para-toluenesulfonyl isocyanate (PTSI) and a monofunctional alcohol (i.e., mono-ol). Thus, in some embodiments, X1 is -S(=O)2-NH-C(=O)-O- and the compatibilizer has the formula

[0043] [ka] The first group is a compound containing a group referred to herein as toluenesulfonyluethane.

[0044] In some embodiments, Z1 is an alkyl. In some embodiments, Z1 is a C6-C40 alkyl group (e.g., C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, or C40 alkyl). For example, in some embodiments, Z1 is a monohydric derivative of a branched or straight chain fatty alcohol, such as 3-methylpentanol, heptanol, octanol, pelargonic alcohol, capric alcohol, undecyl alcohol, lauryl alcohol, tridecyl alcohol, myristyl alcohol, pentadecyl alcohol, cetyl alcohol, palmitolyl alcohol, heptadecyl alcohol, stearyl alcohol, oleyl alcohol, nonadecyl alcohol, arachidyl alcohol, etc. In some embodiments, Z1 is isostearyl.

[0045] In some embodiments, Z1 is -(L2) s -(L3) t -R1, s is 0 or 1, t is 1, L2 is an alkylene (e.g., C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, or C12 alkylene), L3 is a polymeric group, and R1 is an alkyl or silyl. In some embodiments, L3 is a polymeric or oligomeric group, such as, but not limited to, a polyether, a polysiloxane, a polyacrylate, a polyester, and a polyolefin. In some embodiments, L3 is a polyether or a polysiloxane group. In some embodiments, L3 is a combination of different polymeric or oligomeric groups, i.e., L3 can have blocks of two or more different polymeric or oligomeric groups. In some embodiments, the polyether is a polyether polyol moiety. In some embodiments, the polyether is a polyalkylene glycol moiety, such as a polyethylene glycol (PEG) or polypropylene glycol (PPG) moiety. In some embodiments, R1 is a C1-C6 alkyl group, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, n-pentyl, or n-hexyl. In some embodiments, R1 is a larger alkyl group, such as a C8-C40 alkyl group, which may be branched or linear and may contain one or more carbon-carbon double bonds. In some embodiments, R1 is a silyl group (e.g., trimethylsilyl). In some embodiments, Z1 is an alkyl-terminated polyether polyol or a silyl-terminated alkylene-polysiloxane moiety (e.g., an alkyl-substituted silyl group, such as trimethylsilyl, or an alkyl-terminated C1-C6 alkylene-PDMS moiety).

[0046] In some embodiments, the compatibilizer is [ka] where n is a variable greater than 1. In some embodiments, n is a variable between 2 and 5,000, between 2 and 1,000, between 2 and 500, between 2 and 100, or between 2 and 50. In some embodiments, n is 5 or greater. In some embodiments, n is 10 or greater.

[0047] In some embodiments, the subject matter of the present disclosure provides a composition comprising a compatibilizer and at least one liquid molecule. Thus, in some embodiments, the subject matter of the present disclosure provides a composition compatibilized with the compatibilizer of the subject matter of the present disclosure. In some embodiments, the composition comprises (a) a liquid matrix, (b) a compatibilizer of the subject matter of the present disclosure (i.e., a compatibilizer comprising (b1) one or more first groups, each of which comprises an arylsulfonyl moiety, and (b2) one or more second groups, each of which comprises an alkyl moiety, a polymeric or oligomeric moiety, or a combination thereof, each of which is bonded to at least one of the one or more first groups), and (c) one or more optional additional components. In some embodiments, the polymeric portion of (b2) is selected from the group comprising polyethers (e.g., polyether polyols), polysiloxanes, polyacrylates, polyesters, and polyolefins (e.g., polyalphaolefins (PAOs)).

[0048] In some embodiments, the compatibilizer (b) has the structure of one of formulas (I)-(V) described hereinabove. In some embodiments, the compatibilizer has the structure of formula (I): A1-X1-Z1(I) [In the formula, A1 is aryl or substituted aryl, X1 is -S(=O)2-NH-C(=O)-O-, -S(=O)2-NH-C(=O)-NH-, or -S(=O)2-NH-C(=O)-, Z1 is alkyl and -(L2) s -(L3) t-R1, s is 0 or 1, t is 0 or 1, L2 is alkylene, L3 is a polymeric or oligomeric moiety, and R1 is alkyl or silyl. In some embodiments, A1 is phenyl or methyl-substituted phenyl. In some embodiments, the compatibilizer is the reaction product of PTSI with a mono-ol, an amine, or a carboxylic acid.

[0049] The liquid matrix (a) can include any liquid, solution, or liquid mixture that can benefit from the presence of the compatibilizer of the present disclosure, alone or in combination with any additional component (c), which can be an additional liquid or solid component. In some embodiments, the liquid matrix comprises or consists of one or more oligomers or polymers. For example, in some embodiments, the liquid matrix comprises or consists of a polymer, such as a polyether, polyester, or PAO (e.g., a polyolefin prepared from the polymerization of 1-alkene, such as 1-hexene or 1-octene, or a polyethylene copolymer thereof). In some embodiments, the liquid matrix comprises one or more monomers, such as an amine, alcohol, isocyanate, polyol, or combinations thereof. In some embodiments, the liquid matrix comprises water. In some embodiments, the liquid matrix comprises an organic solvent (e.g., a polar or non-polar aprotic organic solvent), an oil, or combinations thereof. In some embodiments, the liquid matrix comprises a hydrocarbon fluid. In some embodiments, the liquid matrix can include any combination of these liquids and / or can include one or more solutes, such as dyes or other colorants, antioxidants, UV stabilizers, polymerization catalysts, and the like.

[0050] For example, in some embodiments, the liquid matrix comprises a reactive or non-reactive resin. In some embodiments, the resin comprises both monomeric and polymeric and / or oligomeric compounds, where the compounds are liquid at a temperature and / or pressure suitable for application or use of the resin, or the compounds are soluble in a suitable solvent such that the resin compound can be provided in solution. In some embodiments, the resin comprises a compound that is liquid at room temperature or soluble in a solvent at room temperature. In some embodiments, the liquid matrix comprises a urethane resin, a silicone resin, an acrylic resin, an epoxy resin, or a silyl-terminated resin.

[0051] Further, particularly suitable liquid epoxy resins can include epoxy materials containing at least one epoxy functional group. The epoxy resins can be monofunctional, difunctional, polyfunctional, and combinations thereof. The epoxy can be aliphatic, cycloaliphatic, aromatic, and the like. In some embodiments, the epoxy resins include liquid epoxy resins based on diglycidyl ether of bisphenol A (DGEBA) or diglycidyl ether of bisphenol F (DGEBF). Liquid epoxy resins typically include a molecular weight of less than about 500 Daltons, preferably between about 150 and 600 Daltons. The molecular weight can be determined by methods known in the art, such as gel permeation (or size exclusion) chromatography.

[0052] The acrylic resin may include an acrylic material containing at least one acrylate and / or methacrylate functional group. The acrylic resin may be monofunctional, difunctional, multifunctional, or a combination thereof, so long as the resulting material blend is liquid at room temperature. Representative monofunctional acrylic resins include esters of (meth)acrylic acid, such as methyl methacrylate, ethyl methacrylate, butyl methacrylate, methyl acrylate, butyl acrylate, cyclohexyl acrylate, hexyl acrylate, 2-ethylhexyl acrylate, lauryl acrylate, ethyl acrylate, dicyclopentadienyloxyethyl methacrylate, cyclohexyl methacrylate, lauryl methacrylate, glycidyl methacrylate, and tetrahydrofurfuryl methacrylate (THFMA). Other monofunctional resins include OH-functional monoethylenically unsaturated monomers such as 3-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 4-hydroxycyclohexyl (meth)acrylate, 1,6-hexanediol mono(meth)acrylate, neopentyl glycol mono(meth)acrylate.

[0053] In some embodiments, the composition comprises one or more optional additional components (c). In some embodiments, the one or more optional additional components comprise solid organic and / or inorganic particles (e.g., nanoparticles and / or microparticles) and / or fibers (e.g., nanofibers). In some embodiments, the composition comprises from about 1% by weight (wt) to about 95% by weight of the additional solid component(s) or from about 1% by volume (vol) to about 80% by volume of the optional additional solid component(s). For example, a "highly filled" resin may comprise from about 35% by weight to about 95% by weight of solid filler particles and / or fibers. Thus, in some embodiments, the composition comprises about 35% to about 95% by weight (e.g., about 35%, about 40%, about 45%, about 50%, about 55%, about 60%, about 65%, about 70%, about 75%, about 80%, about 85%, about 90%, or about 95%) of solid filler particles or fibers, or a combination of solid filler particles and / or fibers (e.g., a combination can include particles of different sizes but the same chemical composition, combinations of particles of different chemical compositions, or combinations of particles of different chemical compositions and different sizes). In some embodiments, the composition comprises about 65% to about 90% by weight of solid filler particles or fibers, or a combination of solid filler particles and / or fibers. In some embodiments, (c) comprises particles and / or fibers comprising one or more of the group including, but not limited to, silicon dioxide, fumed silica, fused quartz, talc, mica, wollastonite, calcium carbonate, carbon, polymers, aluminum, aluminum trihydroxide (ATH), iron, silver, metal oxides, boron nitride, and aluminum nitride.

[0054] In some embodiments, optional further component (c) comprises a further liquid component, for example, the further liquid component is a liquid that is incompatible (e.g., immiscible or only partially miscible) with the liquid matrix (a). For example, in some embodiments, (a) comprises water and (c) comprises an oil (e.g., any non-polar hydrocarbon-based liquid). In some embodiments, (a) comprises a non-polar liquid and (c) comprises water. In some embodiments, when (c) comprises a liquid component, (c) comprises at least about 1% by weight and less than about 50% by weight (or less than about 40% by weight, less than about 30% by weight, less than about 25% by weight, less than about 20% by weight, less than about 15% by weight, or less than about 10% by weight) of the total weight of the composition.

[0055] In some embodiments, the compatibilizer (b) has the structure of formula (I): A1-X1-Z1(I) [In the formula, A1 is aryl or substituted aryl, X1 is -S(=O)2-NH-C(=O)-O-, -S(=O)2-NH-C(=O)-NH-, or -S(=O)2-NH-C(=O)-, Z1 is alkyl and -(L2) s -(L3) t -R1, s is 0 or 1, t is 0 or 1, L2 is alkylene, L3 is a polymeric or oligomeric moiety, and R1 is alkyl or silyl. In some embodiments, A1 is phenyl or substituted phenyl. In some embodiments, A1 is alkyl-substituted phenyl (e.g., methyl-substituted phenyl).

[0056] In some embodiments, Z1 is an alkyl. In some embodiments, Z1 is a C6-C40 alkyl group (e.g., C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, or C40 alkyl). For example, in some embodiments, Z1 is a monohydric derivative of a branched or straight chain fatty alcohol, such as 3-methylpentanol, heptanol, octanol, pelargonic alcohol, capric alcohol, undecyl alcohol, lauryl alcohol, tridecyl alcohol, myristyl alcohol, pentadecyl alcohol, cetyl alcohol, palmitryl alcohol, heptadecyl alcohol, stearyl alcohol, oleyl alcohol, nonadecyl alcohol, arachidyl alcohol, etc. In some embodiments, Z1 is isostearyl.

[0057] In some embodiments, a compatibilizer is provided in the composition where Z1 is an alkyl, and (a) comprises a resin, such as an epoxy resin or a resin comprising an isocyanate. In some embodiments, a compatibilizer is provided in the composition where Z1 is an alkyl, and (a) comprises a PAO or water. In some embodiments, a compatibilizer is included in the composition where optional additional component (c) is present, such as organic and / or inorganic particles or fibers (e.g., ATH or iron particles). In some embodiments, a compatibilizer is present in the composition where optional additional component (c) is not present. In some embodiments, Z1 is -(L2) s -(L3) t -R1, s is 0, t is 1, L3 is a polyether polyol, and R1 is an alkyl (e.g., C1-C6 alkyl). Thus, for example, Z1 can comprise a polyether polyol moiety, e.g., a polypropylene moiety, terminated with a lower alkyl group (e.g., methyl, ethyl, propyl, or butyl). In some embodiments, a compatibilizer in which Z1 comprises a polyether polyol is present in a composition in which (a) comprises a polyol. In some embodiments, the composition further comprises organic and / or inorganic particles and / or fibers.

[0058] In some embodiments, Z1 is -(L2) s -(L3) t -R1, s is 1, t is 1, L2 is alkylene (e.g., C1-C6 alkylene that may include oxygen atoms inserted into the alkylene group), L3 is a polysiloxane moiety, and R1 is silyl (e.g., trialkylsilyl). In some embodiments, a compatibilizer in which L3 comprises a polysiloxane moiety can be used in a composition in which (a) comprises PDMS. In some embodiments, the composition further comprises solid particles and / or fibers, e.g., ATH particles.

[0059] In some embodiments, the compatibilizer has the structure of formula (Ia): [ka] [Wherein, Z1 is alkyl and -(L2) s -(L3) t -R1, s is 0 or 1, t is 0 or 1, L2 is alkylene, L3 is a polymeric or oligomeric moiety, and R1 is alkyl or silyl.

[0060] In some embodiments, the composition comprises one of the compositions selected from the group comprising: (i)-(vi). (i) A1 is a methyl-substituted phenyl, X1 is -S(=O)2-NH-C(=O)-O-, and Z1 is -(L2) s -(L3) t -R1, s is 0, t is 1, L3 is a polyether polyol moiety, R1 is methyl, the liquid matrix (a) comprises a polyether polyol, and the optional further component (c) comprises one or more organic and / or inorganic particles (e.g., ATH particles); (ii) A1 is a methyl-substituted phenyl, X1 is -S(=O)2-NH-C(=O)-NH-, and Z1 is -(L2) s -(L3) t-R1, s is 0, t is 1, L3 is a polyether polyol, R1 is methyl, the liquid matrix (a) comprises a polyether polyol, and the optional further component (c) comprises one or more organic and / or inorganic particles (e.g., ATH particles); (iii) A1 is methyl substituted phenyl, X1 is -S(=O)2-NH-C(=O)-O-, Z1 is isostearyl, the liquid matrix (a) comprises a PAO, and the optional further component (c) comprises one or more organic and / or inorganic particles (e.g., iron particles); (iv) A1 is a methyl-substituted phenyl, X1 is -S(=O)2-NH-C(=O)-O-, and Z1 is -(L2) s -(L3) t -R1, s is 1, t is 1, L2 is -CH2CH2-OCH2CH2CH2-, L3 is a PDMS moiety, R1 is silyl, the liquid matrix (a) comprises a silicone resin, and the optional further component (c) comprises one or more organic and / or inorganic particles (e.g., ATH particles); (v) A1 is a methyl-substituted phenyl, X1 is -S(=O)2-NH-C(=O)-O-, Z1 is isostearyl, the liquid matrix (a) comprises an isocyanate (e.g., HDMI), and the optional further component (c) comprises one or more organic and / or inorganic particles (e.g., ATH particles); (vi) A1 is methyl substituted phenyl, X1 is -S(=O)2-NH-C(=O)-O-, Z1 is polyoxyethylene (5) oleyl ether, the liquid matrix (a) comprises water, and the optional further component (c) comprises a PAO.

[0061] As described herein above, the compositions of the presently disclosed subject matter can be used in a variety of different applications, in some embodiments, the compositions are selected from the group including, but not limited to, paints, coatings, cleaning solutions, lubricants, magnetorheological fluids, adhesives, drilling fluids, cosmetic fluids, and inks. In some embodiments, the presently disclosed subject matter provides a method of modifying the viscosity of a polymeric resin (or other liquid) composition, comprising contacting a composition comprising a polymeric resin (or other liquid) with a compatibilizer of the presently disclosed subject matter (e.g., a compatibilizer comprising one or more first groups, each comprising an arylsulfonyl moiety, and one or more second groups, each comprising an alkyl group, a polymeric group, or a combination thereof, each bonded to at least one of the one or more first groups). In some embodiments, the compatibilizer has a structure according to one of formulas (I)-(V) described herein above. In some embodiments, the compatibilizer has a structure according to formula (I). In some embodiments, the compatibilizer has a structure according to formula (Ia).

[0062] In some embodiments, the polymer resin comprises a polyol, an isocyanate, an amine, a polysiloxane, a PAO, an epoxy resin, an acrylic resin, or a combination thereof. In some embodiments, the polymer resin is a filled polymer resin, i.e., a polymer resin comprising solid organic and / or inorganic particles and / or fibers as described herein above (e.g., silicon dioxide, fumed silica, fused quartz, talc, mica, wollastonite, calcium carbonate, carbon black, carbon fibers, polymer fibers, microparticles and / or nanoparticles comprising one or more of aluminum, aluminum trihydroxide (ATH), iron, silver, metal oxides, boron nitride, and aluminum nitride, and / or nanofibers). In some embodiments, the polymer resin composition comprises from about 35% to about 95% by weight of solid organic and / or inorganic particles and / or fibers.

[0063] In some embodiments, modifying the viscosity of a polymeric resin (or other liquid composition) includes, for example, reducing the viscosity of the polymeric resin (or other composition) as compared to the same composition but without the compatibilizer, in some embodiments the viscosity is reduced as compared to the viscosity of the same composition including a conventional surfactant or other type of compatibilizer instead of a compatibilizer of the presently disclosed subject matter. Compatibilizers of the presently disclosed subject matter can typically be selected to reduce viscosity, but in some embodiments, the compatibilizer can be selected to impart shear thinning or thixotropic rheological behavior to the resin or other composition. In some embodiments, the compatbilizing agent can be selected to increase viscosity, for example, by selecting a compatibilizing agent having one or more second groups that are dissimilar to the liquid matrix and / or have an immiscible or partially miscible structure.

[0064] In some embodiments, the presently disclosed subject matter provides a method for preparing a polyurethane. In some embodiments, the method includes contacting a composition including a polyol and / or an isocyanate resin with a compatibilizer of the presently disclosed subject matter (e.g., the compatibilizer includes one or more first groups, each including an arylsulfonyl moiety, and one or more second groups, each including an alkyl moiety, a polymeric moiety, or a combination thereof, each bonded to at least one of the one or more first groups). In some embodiments, the compatibilizer has a structure according to any one of formulas (I)-(V) described herein above. In some embodiments, the compatibilizer has a structure according to formula (I). In some embodiments, the compatibilizer has a structure according to formula (Ia).

[0065] Polyurethanes can be prepared, for example, by reacting an isocyanate, such as a diisocyanate, with a polyol, such as a difunctional polyol, to prepare an isocyanate-terminated prepolymer. In some embodiments, polyurethanes can be prepared by reacting an isocyanate directly with a polyol without forming a prepolymer. Suitable isocyanates for use in preparing polyurethanes in accordance with the subject matter of the present disclosure include aromatic, aliphatic, and cycloaliphatic polyisocyanates, such as isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), methylene bis(phenyl diisocyanate) (MDI), 4,4'-methylenedicyclohexyl diisocyanate (HMDI or HMDI), and the like. 12 MDI, monomeric cycloaliphatic isocyanates, m-phenylene diisocyanate, 2,4- and / or 2,6-toluene diisocyanate (TDI), hexamethylene 1,6-diisocyanate, tetramethylene-1,4-diisocyanate, cyclohexane-1,4-diisocyanate, hexahydrotoluene diisocyanate, naphthylene-1,5-diisocyanate, methoxyphenyl-2,4-diisocyanate, 4,4'-biphenylene diisocyanate, 3,3'-dimethoxyphenyl (dimethyoxyphenyl) diisocyanate, dimethyldiphenylmethane-4,4'-diisocyanate, 3,3'-dimethyldiphenylmethane-4,4'-diisocyanate, 4,4',4''-triphenylmethane diisocyanate, polymethylene polyphenylisocyanate, toluene-2,4,6-trilsocyanate, and 4,4'-dimethyldiphenylmethane-2,2',5,5'-tetraisocyanate and polymeric MDI, and mixtures and blends thereof.

[0066] Suitable polyols include, but are not limited to, compounds such as alkylene glycols (e.g., ethylene glycol, propylene glycol, 1,4-butanediol, 1,6 hexanediol, etc.), glycol ethers and polyethers, e.g., difunctional polyether polyols, e.g., diethylene glycol, triethylene glycol, dipropylene glycol, tripropylene glycol, etc., glycerin, trimethylolpropane, tertiary amine-containing polyols, e.g., triethanolamine, triisopropanolamine, and ethylene oxide and / or propylene oxide adducts of ethylenediamine, toluenediamine, etc., polyether polyols, carbonates, etc., and mixtures and blends thereof. Polyols, e.g., polyester polyols, including the reaction product of a diol with a polycarboxylic acid or an anhydride thereof, e.g., a dicarboxylic acid or a dicarboxylic acid anhydride, are also suitable. The polycarboxylic acid or anhydride may be aliphatic, cycloaliphatic, aromatic and / or heterocyclic, and may be substituted, e.g., with halogen atoms. The polycarboxylic acid may also be unsaturated. Examples of these polycarboxylic acids include, but are not limited to, succinic acid, adipic acid, terephthalic acid, isophthalic acid, trimellitic anhydride, phthalic anhydride, maleic acid, maleic anhydride, and fumaric acid.

[0067] In some embodiments, the composition includes both an isocyanate and a polyol. The ratio of the two components can be selected to provide a desired isocyanate index (the ratio of isocyanate to isocyanate reactive groups, e.g., hydroxyl groups of a polyol). In some embodiments, the isocyanate and polyol components are mixed to provide an isocyanate to hydroxyl (NCO:OH) equivalent index of about 0.3 to about 1.5 (e.g., 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1.0, 1.1, 1.2, 1.3, 1.4, or about 1.5). In some embodiments, the composition can further include a catalyst, e.g., an amine catalyst or an organometallic catalyst (e.g., a tin-containing organometallic catalyst).

[0068] In some embodiments, the method further comprises contacting the composition comprising the polyol and / or isocyanate resin with one or more organic and / or inorganic filler particles (e.g., microparticles and / or nanoparticles) and / or fibers (e.g., nanofibers). Suitable organic and / or inorganic filler particles and / or fibers include, but are not limited to, silicon dioxide, fumed silica, fused quartz, talc, mica, wollastonite, calcium carbonate, carbon black, carbon fibers, polymeric fibers, aluminum, aluminum trihydroxide (ATH), iron, silver, metal oxides, boron nitride, and aluminum nitride. In some embodiments, the method comprises contacting the composition comprising the polyol and / or isocyanate with two or more types of organic or inorganic filler particles or two or more sizes of organic or inorganic filler particles.

[0069] In some embodiments, the compatibilizer is contacted with the composition comprising the polyol and / or isocyanate resin in an amount of about 0.05% to about 49% by volume based on the total weight of the composition comprising the polyol and / or isocyanate resin and the liquid comprising the compatibilizer. In some embodiments, the compatibilizer is contacted with the polyol and / or isocyanate resin in an amount of about 0.5% to about 12% by weight (e.g., about 0.5, 1.0, 1.5, 2.0, 2.5, 3.0, 4.0, 5.0, 6.0, 7.0, 8.0, 9.0, 10.0, 11.0, or about 12.0% by weight) based on the total weight of the composition comprising the polyol and / or isocyanate resin and the liquid comprising the compatibilizer. In some embodiments, the compatibilizer is contacted with the polyol and / or isocyanate resin in an amount of about 0.5% to about 3.0% by weight based on the total weight of the liquid in the composition. In some embodiments, the compatibilizer is contacted with the composition in an amount of about 0.1% to about 2% by weight, based on the total weight of the composition.

[0070] The compatibilizers of the present disclosure can provide several advantages when used in place of conventional surfactants or other types of compatibilizers used in resins containing polyols and / or isocyanates. For example, the compatibilizers of the present disclosure can provide improved stability given their lack of reactivity. Acid esters, such as those conventionally used in these types of resins, can react undesirably with isocyanate groups, thus increasing the viscosity of the resin and reducing its shelf life. The compatibilizers of the present disclosure also do not interact easily with the catalysts used in these resins. In contrast, acid esters can complex with the catalyst, thereby inhibiting or delaying curing. The improved efficiency provided by the use of the compatibilizers of the present disclosure can also result in less plasticization of the resulting cured polyurethane matrix. Plasticization can be undesirable as it can impair the mechanical properties of the polyurethane. In addition, the compatibilizers of the present disclosure can provide for higher filler loadings and / or the use of fillers with higher surface areas. The compatibilizers of the present disclosure are also easier to synthesize. For example, the reaction of PTSI with mono-ols is rapid and without significant by-products.

[0071] Some of the improvements in the effect of the compatibilizers of the present disclosure are shown in Figures 4-8. For example, Figure 4 shows the effect of the amount of compatibilizer of the presently disclosed subject matter on the viscosity of a polyol resin (i.e., polypropylene glycol (PPG) resin) highly filled with 79 wt% ATH particles at the same shear rate, and Figure 5 shows the effect of various compatibilizers of the presently disclosed subject matter on the viscosity of the same filled resin system at different shear rates. The compatibilizers in Figure 5 have a variety of "second groups" based on, for example, alkyl-terminated PPG mono-ol (Example 1), amine derivatives of PPG (Example 3), polyoxyethylene (POE) (4) lauryl ether (Example 4), and POE (20) sorbitan monooleate (Example 5). Figures 6-8 show the effect of exemplary compatibilizers of the presently disclosed subject matter on the viscosity of different liquid matrices, i.e., highly filled hydrogenated MDI resin (Figure 6), filled PAO fluid (Figure 7), and vinyl-terminated PDMS resin (Figure 8). The flat Newtonian behavior of the formulations containing the compatibilizer reflects the agent's strong ability to wet and disperse the filler in the liquid matrix. EXAMPLES

[0072] The following examples are included to further illustrate various embodiments of the presently disclosed subject matter. However, it should be understood by those of skill in the art in light of this disclosure that many changes can be made to the specific embodiments disclosed and still obtain a like or similar result without departing from the spirit and scope of the presently disclosed subject matter.

[0073] (Examples 1 to 8) A series of example compatibilizers were prepared. The reactants used to prepare the agents and their corresponding mass percentages in different agents are summarized in Table 1 below. The example compatibilizers were synthesized according to the following general procedure. Reactant A was added to a 60 mL glass bottle equipped with a magnetic stir bar and inlet / outlet flow lines of dry nitrogen. Reactant A was then stirred under a steady flow of dry nitrogen while reactant B was added incrementally over approximately 30 minutes. The amount of reactant B was based on the stoichiometry of the reactants with a final target total mass of 20 g. Stirring was continued for at least an additional 60 minutes after which completion of the reaction was verified by Fourier transform infrared (FTIR) spectroscopy.

[0074] [Table 1]

[0075] (Examples 9 to 30) Table 2 provides an overview of the control and exemplary formulations used to demonstrate the viscosity reducing ability of the embodied compatibilizers. In selected formulations, molecular sieve powder (particle size=5 μm, sieve pore size=4 angstroms) was used to remove any water entrapped by the liquid resin and / or filler. The formulations were prepared by mixing the components under vacuum using a DAC 800 HAUSCHILD SPEEDMIXER™ Hauschild GmbH&Co., KG; Hamm, Germany) according to the mass percentages listed in Table 2. The steady shear viscosity of each formulation was measured at 25° C. as a function of shear rate using a TA Discovery rheometer (TA Instruments, New Castle, Delaware, USA) equipped with a 20 mm parallel plate geometry set at a 0.5 mm gap. The results are reported in Table 3 below.

[0076] [Table 2] JPEG2025511729000008.jpg205146 JPEG2025511729000009.jpg205102 [Table 3]

[0077] Examples 9 (control) and 10 were prepared using para-toluenesulfonyl isocyanate (PTSI) and polypropylene glycol monobutyl ether (M n The compatibilizer according to Example 1, derived from the reaction with aluminum trihydrate (ATH) particle-filled polypropylene glycol (PPGM) n =1000) to the liquid matrix. Viscosity across all shear rates is dramatically reduced across all shear rates with the incorporation of the compatibilizer. The level of viscosity reduction increases with increasing compatibilizer concentration (Examples 10A-10D), decreasing by approximately an order of magnitude at the highest concentration. Furthermore, the viscosity data for Example 10D shows Newtonian behavior, reflecting good wetting by the compatibilizer of Example 1 and dispersion of the filler throughout the liquid matrix.

[0078] Example 11 is a mixture of PTSI and a higher molecular weight polypropylene glycol monobutyl ether (M n The compatibilizer based on Example 2, derived from the reaction with 1,4-dichlorophenyl ether (M = 2490), was added to the ATH particle-filled PPG (M n = 1000) to the liquid matrix. As can be seen from Table 3, the data for Example 11 shows an order of magnitude decrease in viscosity relative to the PPG / ATH control (Example 9).

[0079] Examples 12 (control) and 13 are comparisons of PTSI and higher molecular weight polypropylene glycol monobutyl ether (M n The compatibilizer according to Example 2, derived from the reaction with 1,4-dichlorophenyl ether (M = 2490), was added to the aluminum oxide particle-filled PPG (M n = 1000) to the liquid matrix. The viscosity of Example 13 is reduced to about 13 to 8 times lower than that of the control.

[0080] Example 14, compared to its control, Example 9, uses a compatibilizer based on Example 3 derived from the reaction with PTSI and monoamine terminated polypropylene glycol (average Mn=600) in a polypropylene glycol liquid (PPG M) filled with ATH particles. n = 1000) to the matrix. The viscosity of Example 14 is in the range of approximately 140 to 10 times lower than the viscosity of the formulation of Example 9, which does not contain a compatibilizer. Example 15, compared to its control, Example 9, uses a compatibilizer based on Example 4 derived from the reaction with PTSI and polyoxyethylene (4) lauryl ether (average Mn=362) in a polypropylene glycol liquid (PPG M) filled with ATH particles. n = 1000) to the matrix. The viscosity of Example 15 is in the range of approximately 23-4 times lower than the viscosity of the formulation of Example 9, which does not contain a compatibilizer. Example 16 compares the effectiveness of a compatibilizer based on Example 5 derived from the reaction with PTSI and polyoxyethylene (20) sorbitan monooleate (average Mn=1310) in a polypropylene glycol liquid (PPG M) filled with ATH particles, as compared to its control, Example 9. n = 1000) to the matrix. The viscosity of Example 16 is in the range of approximately 18 to 7 times lower than the viscosity of the formulation of Example 9, which does not contain a compatibilizer.

[0081] Examples 17 (control) and 18 show the effect of adding a compatibilizer based on Example 6 derived from reaction with PTSI and isostearyl alcohol to an HMDI liquid matrix filled with ATH particles. The viscosity is dramatically reduced, i.e., by 2-3 orders of magnitude, across all shear rates upon incorporation of the compatibilizer. Furthermore, the viscosity data for Example 18 shows Newtonian behavior, reflecting good wetting by the compatibilizer of Example 6 and dispersion of the filler throughout the liquid matrix. Examples 19 (control) and 20 show the effect of adding a compatibilizer based on Example 6 derived from the reaction with PTSI and isostearyl alcohol to an HDMI liquid matrix filled with aluminum oxide particles. The viscosity across all shear rates is dramatically reduced across all shear rates when the compatibilizer is incorporated. Furthermore, the viscosity data shows Newtonian behavior, reflecting good wetting by the compatibilizer of Example 6 and dispersion of the filler throughout the liquid matrix. Examples 21 (control) and 22 show the effect of adding a compatibilizer based on Example 6 derived from reaction with PTSI and isostearyl alcohol to a 2.5 centistoke polyalphaolefin (PAO-2.5) liquid matrix loaded with iron particles. The viscosity across all shear rates is reduced by a factor of about 2 to 22 across all shear rates with the incorporation of the compatibilizer.

[0082] Examples 23 (control) and 24 show the effect of adding a compatibilizer based on Example 7 derived from reaction with PTSI and a monocarbinol terminated polydimethylsiloxane (average Mn=10,000) to a 100 centistoke vinyl terminated polymethylsiloxane liquid matrix filled with ATH. The viscosity over all shear rates is nominally reduced by a factor of 2-5 over all shear rates with the incorporation of the compatibilizer. Example 26 shows the effect of adding a compatibilizer based on Example 3 derived from reaction with PTSI and monoamine-terminated polypropylene glycol (average Mn=600) to a silyl-terminated polyether (viscosity=7.0 Pa·sec) matrix loaded with ATH particles, compared to its control, Example 25. The viscosity of Example 26 is approximately 1.9-1.4 times lower than the formulation of Example 25, which does not contain a compatibilizer.

[0083] Examples 27 (control) and 28 were prepared by adding the following to a 4 ounce glass bottle: deionized water (liquid matrix), PAO-2.5 fluid, and optionally a compatibilizer based on Example 8 derived from the reaction with PTSI and polyoxyethylene (5) oleyl ether (average Mn=489) according to the weight percentages listed in Table 2. The target total weight for Examples 27 and 28 with and without compatibilizer, respectively, was 60 grams. The formulations were then mixed at room temperature for 10 minutes at 1800 rpm using a Caframo mixer (Caframo, Wiarton, Ontario, Canada) equipped with a 25.4 mm diameter Cowles disperser blade. Immediately after the mixer was stopped, the mixtures were monitored for stability. Example 27 showed immediate phase separation of the PAO-2.5 fluid from the water with PAO, forming a distinct clear layer just above the adjacent clear water phase. In contrast, Example 28 showed a uniform opaque white appearance throughout the mixture, demonstrating the ability of the compatibilizer of Example 8 to produce an oil-in-water emulsion. The mixture showed some signs of phase separation after approximately 1 hour, but the top and bottom phases remained opaque white.

[0084] Examples 29 (control) and 30 were prepared according to Table 2 to compare the effect of adding 2 wt. % of the compatibilizer of Example 6 based on the reaction of PTSI with isostearyl alcohol on the coefficient of friction on stainless steel. In particular, Example 30 was prepared by adding 29.4 g and 0.6 g of PAO-2.5 liquid matrix and the compatibilizer of Example 6, respectively, to a 2 ounce glass bottle. The bottle was capped and placed on a roller overnight for 16 hours to ensure thorough mixing. Coefficient of friction (COF) measurements were performed on the pure PAO fluid (Example 29) and the PAO fluid containing the compatibilizer of Example 6 (Example 30) using a Discovery ARES rheometer (TA Instruments, New Castle, Delaware, USA) equipped with stainless steel in a ring-on-plate configuration. The blend of Example 30 showed a COF value of 0.16, which was approximately 29% lower than the value of 0.23 for the PAO fluid alone.

[0085] It will be understood that various details of the presently disclosed subject matter can be changed without departing from the scope of the presently disclosed subject matter. Further, the foregoing description is intended to be illustrative only and not limiting.

Claims

1. (a) a liquid matrix; (b)(b1) one or more first groups, each of which comprises an arylsulfonyl moiety; and (b2) one or more second groups, each of which comprises an alkyl moiety, a polymeric or oligomeric moiety, or a combination thereof, and each of the one or more second groups is bonded to at least one of the one or more first groups; A compatibilizer comprising (c) one or more optional further components A composition comprising:

2. The composition of claim 1 , wherein the polymeric portion of the one or more second groups is selected from the group consisting of polyethers, polysiloxanes, polyacrylates, polyesters, and polyolefins.

3. The compatibilizer (b) is represented by the formula (I) to (V) A 1 -X 1 -Z 1 (I)、 A 1 -X 1 -Z 2 -X 2 -A 1 (II)、 Z 1 -X 2 -A 2 -X 1 -Z 1 (III)、 A 1 -(X 1 -Z 2 -X 2 -A 2 ) n -X 1 -Z 2 -X 2 -A 1 (IV)、 (A) 1 -X 1 ) p -Z 3 (V) 3. The composition of claim 1 or claim 2 having one of the following structures: [In the formula, n is an integer equal to or greater than 1; p is an integer equal to or greater than 3; Each A 1 is aryl or substituted aryl; Each A 2 is arylene or substituted arylene; Each X 1 is -S(=O) 2 -NH-C(=O)-Q- or -S(=O) 2 -NH-C(=O)-, Each X 2 is -Q-(C=O)-NH-S(=O) 2 - or -C(=O)-NH-S(=O) 2 - and Each Q is O or NH; Z 1 is an alkyl group and -(L 2 ) s - (L 3 ) t -R 1 s is 0 or 1, t is 0 or 1, and L 2 is alkylene; L 3 is a polymeric or oligomeric moiety, R 1 is alkyl or silyl, Z 2 is an alkylene, polymeric or oligomeric moiety, or combinations thereof; Z 3 is a polyvalent radical derived from a compound containing at least three hydroxy, amino, or carboxylic acid groups.

4. The composition of any one of claims 1 to 3, wherein the liquid matrix comprises water, oil, a hydrocarbon fluid, an organic solvent, or a combination thereof.

5. 5. The composition of any one of claims 1 to 4, wherein the liquid matrix comprises a reactive or non-reactive resin, an oligomer, a polymer, an amine, an alcohol, an isocyanate, a polyol, or a combination thereof, and the liquid matrix may comprise a polyether, a polyester, a polyol, a polyalphaolefin (PAO), an isocyanate resin, a urethane resin, a silicone resin, an acrylic resin, an epoxy resin, and a silyl-terminated resin.

6. 6. The composition of any one of claims 1 to 5, wherein optional further component (c) comprises solid organic and / or inorganic particles and / or fibers, component (c) may comprise one or more particles and / or fibers selected from the group consisting of silicon dioxide, fumed silica, fused quartz, talc, mica, wollastonite, calcium carbonate, carbon, polymers, aluminum, aluminum trihydroxide (ATH), iron, silver, metal oxides, boron nitride and aluminum nitride.

7. 6. The composition of any one of claims 1 to 5, wherein the optional further component (c) comprises a further liquid component, said further liquid component being a liquid that is immiscible with the liquid matrix (a).

8. The composition of any one of claims 1 to 7, wherein the compatibilizer has the structure of formula (I): A 1 -X 1 -Z 1 (I) [In the formula, A 1 is aryl or substituted aryl; X 1 is -S(=O) 2 -NH-C(=O)-O-, -S(=O) 2 -NH-C(=O)-NH-, or -S(=O) 2 -NH-C(=O)-, Z 1 is an alkyl group and -(L 2 ) s - (L 3 ) t -R 1 s is 0 or 1, t is 0 or 1, and L 2 is alkylene; L 3 is a polymeric or oligomeric moiety, R 1 is alkyl or silyl.

9. A 1 The composition of claim 8, wherein is phenyl or methyl substituted phenyl.

10. Z 1 The composition of claim 8 or claim 9, wherein is alkyl and may be isostearyl.

11. Z 1 Ga-(L 2 ) s - (L 3 ) t -R 1 where s is 0, t is 1, and L 3 is a polyether polyol moiety, R 1 The composition of claim 8 or claim 9, wherein is C1-C6 alkyl.

12. Z 1 Ga-(L 2 ) s - (L 3 ) t -R 1 s is 1, t is 1, and L 2 is alkylene; L 3 is a polysiloxane moiety, R 1 The composition of claim 8 or claim 9, wherein is silyl.

13. 10. The composition of claim 8 or claim 9, wherein the compatibilizer has the structure of formula (Ia): 【Chemistry 1】 [In the formula, Z 1 is an alkyl group and -(L 2 ) s - (L 3 ) t -R 1 s is 0 or 1, t is 0 or 1, and L 2 is alkylene; L 3 is a polymeric or oligomeric moiety, R 1 is alkyl or silyl.

14. A 1 is a methyl-substituted phenyl; 1 -S (=O) 2 -NH-C(=O)-O-, and Z 1 Ga-(L 2 ) s - (L 3 ) t -R 1 where s is 0, t is 1, and L 3 is a polyether polyol moiety, R 1 10. The composition of claim 8 or claim 9, wherein: R is methyl; the liquid matrix (a) comprises a polyether polyol; and the optional further component (c) comprises one or more organic and / or inorganic particles, and may comprise ATH particles.

15. A 1 is a methyl-substituted phenyl; 1 -S (=O) 2 -NH-C(=O)-NH-, and Z 1 Ga-(L 2 ) s - (L 3 ) t -R 1 where s is 0, t is 1, and L 3 is a polyether polyol, R 1 10. The composition of claim 8 or claim 9, wherein: R is methyl; the liquid matrix (a) comprises a polyether polyol; and the optional further component (c) comprises one or more organic and / or inorganic particles, and may comprise ATH particles.

16. A 1 is a methyl-substituted phenyl; 1 -S (=O) 2 -NH-C(=O)-O-, and Z 1 10. The composition of claim 8 or claim 9, wherein is isostearyl, the liquid matrix (a) comprises PAO, and the optional further component (c) comprises one or more organic and / or inorganic particles, and may comprise iron particles.

17. A 1 is a methyl-substituted phenyl; 1 -S (=O) 2 -NH-C(=O)-O-, and Z 1 Ga-(L 2 ) s - (L 3 ) t -R 1 s is 1, t is 1, and L 2 Ha-CH 2 CH 2 -OCH 2 CH 2 CH 2 - and L 3 is the polydimethylsiloxane (PDMS) moiety, R 1 is silyl, the liquid matrix (a) comprises a silicone resin, and the optional further component (c) comprises one or more organic and / or inorganic particles, and may comprise ATH particles.

18. A 1 is a methyl-substituted phenyl; 1 -S (=O) 2 -NH-C(=O)-O-, and Z 1 is isostearyl, the liquid matrix (a) comprises an isocyanate and may comprise HDMI, and the optional further component (c) comprises one or more organic and / or inorganic particles and may comprise ATH particles.

19. A 1 is a methyl-substituted phenyl; 1 -S (=O) 2 -NH-C(=O)-O-, and Z 1 10. The composition of claim 8 or claim 9, wherein: is polyoxyethylene (5) oleyl ether; the liquid matrix (a) comprises water; and the optional further component (c) comprises a PAO.

20. The composition of any one of claims 1 to 19, selected from the group consisting of paints, coatings, cleaning solutions, lubricants, magnetorheological fluids, adhesives, drilling fluids, cosmetic fluids, and inks.

21. 1. A method of modifying the viscosity of a polymeric resin composition comprising contacting a composition comprising a polymeric resin with a compatibilizer, the compatibilizer comprising: (b1) one or more first groups, each of which comprises an arylsulfonyl moiety; and (b2) one or more second groups, each of which comprises an alkyl group, a polymeric or oligomeric group, or a combination thereof, and each of the one or more second groups is bonded to at least one of the one or more first groups; A method comprising:

22. 22. The method of claim 21 , wherein the compatibilizer has the structure of formula (I): A 1 -X 1 -Z 1 (I) [In the formula, A 1 is an aryl or substituted aryl group; X 1 is -S(=O) 2 -NH-C(=O)-Q- or -S(=O) 2 -NH-C(=O)-; Q is O or NH; Z 1 is an alkyl group and -(L 2 ) s - (L 3 ) t -R 1 s is 0 or 1, t is 0 or 1, and L 2 is alkylene; L 3 is a polymeric or oligomeric moiety, R 1 is alkyl or silyl.

23. 23. The method of claim 21 or claim 22, wherein the polymeric resin comprises solid organic and / or inorganic filler particles and / or fibers.

24. 24. The method of claim 23, wherein the solid organic and / or inorganic filler particles and / or fibers comprise one or more of silicon dioxide, fumed silica, fused quartz, talc, mica, wollastonite, calcium carbonate, carbon black, carbon fibers, polymeric fibers, aluminum, aluminum trihydroxide (ATH), iron, silver, metal oxides, boron nitride, and aluminum nitride.

25. The method of any one of claims 21 to 24, wherein the polymeric resin comprises a polyol, an isocyanate, an amine, a polysiloxane, a polyalphaolefin, an epoxy resin, or an acrylic resin.

26. 1. A method for preparing a polyurethane comprising contacting a composition comprising a polyol and / or an isocyanate resin with a compatibilizer, the compatibilizer comprising: (b1) one or more first groups, each of which comprises an arylsulfonyl moiety; and (b2) one or more second groups, each of which comprises an alkyl moiety, a polymeric or oligomeric moiety, or a combination thereof, and each of the one or more second groups is bonded to at least one of the one or more first groups; A method comprising:

27. 27. The method of claim 26, wherein the compatibilizer has the structure of formula (I): A 1 -X 1 -Z 1 (I) [In the formula, A 1 is an aryl or substituted aryl group; X 1 is -S(=O) 2 -NH-C(=O)-Q- or -S(=O) 2 -NH-C(=O)-; Q is O or NH; Z 1 is an alkyl group and -(L 2 ) s - (L 3 ) t -R 1 s is 0 or 1, t is 0 or 1, and L 2 is alkylene; L 3 is a polymeric or oligomeric group, which may be a polyether or polysiloxane group; R 1 is alkyl or silyl.

28. 28. The method of claim 26 or claim 27, further comprising contacting the composition with one or more organic and / or inorganic filler particles and / or fibers.

29. 30. The method of claim 28, wherein the one or more organic and / or inorganic filler particles and / or fibers comprise one or more of silicon dioxide, fumed silica, fused quartz, talc, mica, wollastonite, calcium carbonate, carbon black, carbon fibers, polymeric fibers, aluminum, aluminum trihydroxide (ATH), iron, silver, metal oxides, boron nitride, and aluminum nitride.

30. The method of any one of claims 26 to 29, further comprising contacting the composition with a catalyst.

31. 31. The method of any one of claims 26 to 30, wherein the compatibilizer is contacted with the composition comprising the polyol and / or isocyanate resin in an amount of about 0.05 vol.% to about 49 vol.%, based on the total volume of the composition comprising the polyol and / or isocyanate resin and the liquid comprising the compatibilizer.

32. Formulas (I) to (V) A 1 -X 1 -Z 1 (I)、 A 1 -X 1 -Z 2 -X 2 -A 1 (II)、 Z 1 -X 2 -A 2 -X 1 -Z 1 (III)、 A 1 -(X 1 -Z 2 -X 2 -A 2 ) n -X 1 -Z 2 -X 2 -A 1 (IV)、 (A) 1 -X 1 ) p -Z 3 (V) A compound having one of the structures: [In the formula, n is an integer equal to or greater than 1; p is an integer equal to or greater than 3; Each A 1 is aryl or substituted aryl; Each A 2 is arylene or substituted arylene; Each X 1 is -S(=O) 2 -NH-C(=O)-Q- or -S(=O) 2 -NH-C(=O)-, Each X 2 is -Q-(C=O)-NH-S(=O) 2 - or -C(=O)-NH-S(=O) 2 - and Each Q is O or NH; Z 1 is an alkyl group and -(L 2 ) s - (L 3 ) t -R 1 s is 0 or 1, t is 0 or 1, and L 2 is alkylene; L 3 is a polymeric or oligomeric moiety, R 1 is alkyl or silyl, Z 2 is an alkylene, polymeric or oligomeric moiety, or combinations thereof; Z 3 is a polyvalent radical derived from a compound containing at least three hydroxy, amino, or carboxylic acid groups.

33. 33. The compound of claim 32 having the structure of formula (I): A 1 -X 1 -Z 1 (I) [In the formula, A 1 is aryl or substituted aryl; X 1 is -S(=O) 2 -NH-C(=O)-O-, -S(=O) 2 -NH-C(=O)-NH-, or -S(=O) 2 -NH-C(=O)-, Z 1 is an alkyl group and -(L 2 ) s - (L 3 ) t -R 1 s is 0 or 1, t is 0 or 1, and L 2 is alkylene; L 3 is a polymeric or oligomeric moiety, R 1 is alkyl or silyl.

34. A 1 34. The compound of claim 33, wherein is phenyl or methyl substituted phenyl.

35. X 1 -S (=O) 2 The compound of claim 33, which is -NH-C(=O)-O-.

36. Z 1 The compound of claim 33, wherein is alkyl, optionally a C8-C40 alkyl.

37. Z 1 Ga-(L 2 ) s - (L 3 ) t -R 1 where s is 0 or 1, t is 1, and L 2 is alkylene; L 3 is a polymeric or oligomeric group, which may be a polyether or polysiloxane group; R 1 is alkyl or silyl.

38. Z 1 The compound of claim 33, wherein is selected from isostearyl, alkyl-terminated polyether polyol, and alkylene-polysiloxane moieties.

39. 【Chemical 2】 39. The compound of claim 38, selected from the group consisting of: wherein n is an integer greater than 1.

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