Compatilizer and application thereof

Abstract

The present disclosure describes compatibilizers and compositions comprising the compatibilizers for use in various filled and unfilled liquid substrates. The compatibilizer may reduce the viscosity of the matrix and / or improve the stability of the matrix. Exemplary compatibilizers include one or more aryl sulfonyl derivatives, such as aryl sulfonyl carbamates, aryl sulfonylureas, and aryl sulfonamides.

Description

[0001] Priority claim

[0002] This application claims the benefit of U.S. Provisional Patent Application Serial No. 63 / 328,476, filed on April 7, 2022, the disclosure of which is incorporated herein by reference in its entirety. Technical Field

[0003] The presently disclosed subject matter relates to compatibilizers for various applications, such as for enhancing the stability and / or reducing the viscosity of filled and unfilled resins or other liquid compositions. Exemplary compatibilizers of the presently disclosed subject matter include arylsulfonyl derivatives, such as compounds including carbamate, urea, and amide derivatives of arylsulfonyl groups. Background Art

[0004] Filled polymer systems have many uses, such as for applications involving thermal or electrical conductivity. For example, electronic components generate heat when in use, and removal of this heat can help prevent thermal degradation of the components and help improve or maintain operating efficiency. Thus, for microelectronic components (e.g., integrated circuits), heat is often removed from the components using greases, gels, or adhesives that contain thermally conductive fillers such as, but not limited to, microparticles and nanoparticles of boron nitride, aluminum nitride, zinc oxide, silicon carbide, and aluminum oxide.

[0005] The properties of the filled polymer system are not only related to the type of polymer matrix and / or filler used, but also related to the amount of filler in the material. Generally, the more fillers added, the higher the viscosity of the resulting material. Therefore, there is usually a compromise between achieving a particularly desired property (e.g., electrical conductivity or thermal conductivity) by a high filler loading while maintaining an operable viscosity. Many filled polymer systems are dispensed with syringes, so it may be desirable to keep the viscosity low enough to allow flow through the needle. In addition, the sedimentation of particles (e.g., micron-sized particles) such as for enhancing the thermal conductivity of encapsulants, gap fillers and adhesives may be a problem that limits the commercial success of such materials. Sedimentation may occur during the storage and transportation of the material, and may be aggravated by high temperature in some adhesive chemistries such as epoxy resins or urethanes. The result is that the material comprises a non-uniformly distributed filler, which may be difficult to homogenize again before use and / or may settle rapidly during use. Mixtures comprising immiscible or partially miscible different 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, which can adversely affect the properties and / or ease of use of the mixture.

[0006] Therefore, there is a continuing need for agents that can improve the stability, homogeneity, and / or viscosity of liquid-based compositions, including liquid-based compositions containing solid organic fillers and / or inorganic fillers. Summary of the invention

[0007] The present invention discloses several embodiments of the subject matter of the present disclosure, and in many cases, lists variations and substitutions of these embodiments. The present invention discloses only examples in numerous and various embodiments. Mentioning one or more representative features of a given embodiment is also for the purpose of example. Such an embodiment may generally have or not have one or more of the features mentioned; similarly, those features may be applied to other embodiments of the subject matter of the present disclosure, whether or not listed in the present invention discloses. In order to avoid excessive repetition, the present invention discloses not to list or suggest all possible combinations of these features.

[0008] In some embodiments, the presently disclosed subject matter provides a composition comprising: (a) a liquid matrix; (b) a compatibilizer, the compatibilizer comprising: (b1) one or more first groups, wherein each of the one or more first groups comprises an arylsulfonyl moiety; and (b2) one or more second groups, wherein each of the one or more second groups comprises a hydrocarbon moiety, a polymer moiety or an oligomer moiety, or a combination thereof, and wherein each of the one or more second groups is attached to at least one of the one or more first groups; and (c) one or more optional additional ingredients.

[0009] In some embodiments, the presently disclosed subject matter provides a method of changing the viscosity of a polymer resin composition, the method comprising contacting a composition comprising a polymer resin with a compatibilizer, wherein the compatibilizer comprises: (b1) one or more first groups, wherein each of the one or more first groups comprises an arylsulfonyl moiety; and (b2) one or more second groups, wherein each of the one or more second groups comprises a hydrocarbon group, a polymer group or an oligomer group, or a combination thereof, and wherein each of the one or more second groups is connected to at least one of the one or more first groups.

[0010] In some embodiments, the presently disclosed subject matter provides a method for preparing a polyurethane, wherein the method comprises contacting a composition comprising a polyol and / or an isocyanate resin with a compatibilizer, wherein the compatibilizer comprises: (b1) one or more first groups, wherein each of the one or more first groups comprises an arylsulfonyl moiety; and (b2) one or more second groups, wherein each of the one or more second groups comprises a hydrocarbon moiety, a polymer moiety or an oligomer moiety, or a combination thereof, and wherein each of the one or more second groups is connected to at least one of the one or more first groups.

[0011] In some embodiments, the subject matter of the present disclosure provides a compound having a structure of one of Formulas (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),

[0012] wherein: n is an integer of 1 or greater; p is an integer of 3 or greater; each A1 is an aryl group or a substituted aryl group; each A2 is an arylene group or a substituted arylene group; 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 selected from a hydrocarbon group and -(L2) s -(L3) t -R1, wherein s is 0 or 1; t is 0 or 1; L2 is an alkylene group, L3 is a polymer moiety or an oligomer moiety, and R1 is a hydrocarbon group or a silyl group; Z2 is an alkylene group, a polymer moiety or an oligomer moiety, or a combination thereof; and Z3 is a polyvalent group derived from a compound including at least three hydroxyl, amino or carboxylic acid groups.

[0013] Therefore, the object of the subject matter of the present disclosure is to provide a compatibilizer comprising an arylsulfonyl moiety, a composition comprising the compatibilizer, and related methods. These and other objects are achieved in whole or in part by the subject matter of the present disclosure. After studying the following description, drawings and examples, other objects and advantages of the subject matter of the present disclosure will become apparent to those skilled in the art. BRIEF DESCRIPTION OF THE DRAWINGS

[0014] The subject matter of the present disclosure may be better understood by reference to the following exemplary drawings. The components in the drawings are not necessarily drawn to scale, but rather the focus is placed on the principles (usually schematic) illustrating the subject matter of the present disclosure. A further understanding of the subject matter of the present disclosure may be obtained by reference to the embodiments described in the illustrations of the accompanying drawings. Although the embodiments shown are only for the purpose of implementing examples of the system of the subject matter of the present disclosure, the overall organization and method of operation of the subject matter of the present disclosure, as well as its further purposes and advantages, may be more easily understood by reference to the drawings and the following description. The drawings are not intended to limit the scope of the subject matter of the present disclosure, but are merely intended to illustrate and provide examples of the subject matter of the present disclosure, and the scope of the subject matter of the present disclosure is specifically described in the appended claims or subsequently amended claims.

[0015] For a more complete understanding of the subject matter of the present disclosure, reference is now made to the following drawings, in which:

[0016] Figures 1A-1D Schematic diagram showing the synthesis of three exemplary arylsulfonyl derivative compatibilizers of the presently disclosed subject matter, which are formed by reacting p-toluenesulfonyl isocyanate (PTSI) with different monofunctional alcohols: monobutyl polypropylene glycol (mPPG, Figure 1A ); Isostearyl alcohol (ISA, Figure 1B ); polyethylene glycol oleyl ether (PEGOE, Figure 1C ) or monomethanol terminated polydimethylsiloxane (PDMS, Figure 1D ).

[0017] Figure 2 is a schematic diagram showing an exemplary "first" or "head" group chemical structure of a compatibilizer of the present disclosure.

[0018] Figure 3 Schematic diagrams showing different exemplary configurations of the compatibilizers of the present disclosure. The "first" group of the compatibilizer is represented by a circle or the letter "B", and the "second" group is represented by a wavy line or the letter "A".

[0019] Figure 4 To show the effect of the amount of compatibilizer (measured as weight percent (wt%) of the total organic content in the formulation) on the viscosity (measured as 0.5 second reciprocal (s -1 ) at a shear rate of 1.5 %. The compatibilizer is the compatibilizer of the presently disclosed subject matter formed by the reaction of p-toluenesulfonyl isocyanate (PSTI) and monobutylpolypropylene glycol (mPPG).

[0020] Figure 5 To show the shear rate (measured in reciprocal seconds (s -1 )) on the viscosity (measured in Pascal seconds (Pa-s)) of a polypropylene glycol (PPG) resin highly filled (79 weight percent (wt%) with aluminum trihydrate particles (ATH). Data for formulations described in Example 1 (solid triangles), Example 3 (open squares), Example 4 (open circles), or Example 5 (solid squares) containing 0.41 wt% of a compatibilizer of the presently disclosed subject matter are shown. For comparison, data for formulations without a compatibilizer of the presently disclosed subject matter are also provided (solid circles).

[0021] Figure 6 To show the shear rate (measured in reciprocal seconds (s -1)) on the viscosity (measured in Pascal seconds (Pa-s)) of a hydrogenated methylene bis(phenyl diisocyanate) (hydrogenated MDI) resin highly filled (79 weight percent (wt%)) with aluminum trihydrate particles (ATH). Data are shown for a formulation of Example 6 containing 0.41 wt% of a compatibilizer (open circles) and the same formulation without the compatibilizer of the disclosed subject matter (filled circles).

[0022] Figure 7 To show the shear rate (measured in reciprocal seconds (s -1 )) on the viscosity (measured in Pascal seconds (Pa-s)) of a polyalphaolefin (PAO) fluid highly filled (78.1 weight percent (wt%)) with iron particles. Data are shown for a formulation of Example 6 containing 0.6 wt% of a compatibilizer (open circles) and the same formulation without the compatibilizer of the disclosed subject matter (filled circles).

[0023] Figure 8 To show the shear rate (measured in reciprocal seconds (s -1 )) on the viscosity (measured in Pascal seconds (Pa-s)) of vinyl terminated polydimethylsiloxane (PDMS) highly filled (84.1 weight percent (wt%)) with aluminum trihydrate (ATH) particles. Data are shown for the formulation of Example 7 containing 0.32 wt% of a compatibilizer (open circles) and a formulation without a compatibilizer of the disclosed subject matter (open circles). DETAILED DESCRIPTION

[0024] The subject matter of the present disclosure will now be described more fully hereinafter, in which some, but not all, embodiments of the subject matter of the present disclosure are described. 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.

[0025] I. Definitions

[0026] The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the disclosed subject matter.

[0027] While it is believed that those of ordinary skill in the art will fully understand the following terms, the following definitions are nonetheless set forth to facilitate illustration of the subject matter of the present disclosure.

[0028] Unless otherwise defined below, all technical and scientific terms used herein have the same meaning as commonly understood by those of ordinary skill in the art. Technical references used herein are intended to refer to techniques commonly understood in the art, including variations of those techniques that are apparent to those skilled in the art or substitutions of equivalent techniques. Although it is believed that those of ordinary skill in the art will fully understand the following terms, the following definitions are still set forth for ease of illustrating the subject matter of the present disclosure.

[0029] In describing the subject matter of the present disclosure, it will be understood that many techniques and steps are disclosed. Each of these techniques has its own benefits, and each can be used in combination with one or more of the other disclosed techniques, or in some cases with all of the other disclosed techniques.

[0030] Therefore, for the sake of clarity, this specification will avoid repeating every possible combination of the various steps in an unnecessary manner. However, the specification and claims should be read based on the following understanding: such combinations are fully within the scope of the present invention and claims.

[0031] Following long-standing patent law convention, when used in this application, including the claims, the terms "a," "an," and "the" mean "one or more." Thus, for example, reference to "a unit" includes a plurality of such units, and so forth.

[0032] 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 attached claims are approximations that may vary depending upon the desired properties sought to be obtained by the presently disclosed subject matter.

[0033] As used herein, the term "about," when referring to a value or amount of a composition, dose, sequence identity (e.g., when comparing two or more nucleotide or amino acid sequences), mass, weight, temperature, time, volume, concentration, percentage, and the like, is intended to include variations from the specified amount of ±20%, in some embodiments ±10%, in some embodiments ±5%, in some embodiments ±1%, in some embodiments ±0.5%, and in some embodiments ±0.1%, as such variations are suitable for performing the disclosed methods or employing the disclosed compositions.

[0034] The term "comprising" is synonymous with "including," "containing," or "characterized by," is inclusive or open-ended, and does not exclude additional, unrecited elements or method steps. "Comprising" is a term used in claim language to indicate that the named elements are required, but other elements may be added and still constitute part of the structure within the scope of the claim.

[0035] As used herein, the phrase "consist of" excludes any element, step, or ingredient not specified in the claim. When the phrase "consist of" appears in an item of the body of a claim rather than immediately following the preamble, it limits only the elements set forth in that item; it does not exclude other elements from the claim as a whole.

[0036] As used herein, the phrase "consisting essentially of" limits the scope of a claim to the specified materials or steps, as well as those materials or steps that do not materially affect the basic characteristics and novelty of the claimed subject matter.

[0037] With respect to the terms "comprising," "consisting of," and "consisting essentially of," where one of these three terms is used herein, the disclosed and claimed subject matter may include the use of either of the other two terms.

[0038] As used herein, when the term "and / or" is used in the context of a list of entities, it refers to the entities as being present individually or in combination. Thus, for example, the phrase "A, B, C, and / or D" includes A, B, C, and D individually, but also includes any and all combinations and subcombinations of A, B, C, and D.

[0039] As used herein, the term "alkyl" may refer to a C 1-40 The term "branched" refers to a hydrocarbon chain that is (inclusive of the end values), linear (i.e., "straight chain"), branched, or cyclic, saturated or at least partially saturated and in some cases fully unsaturated (i.e., alkenyl and alkynyl), including, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, octyl, vinyl, propenyl, butenyl, pentenyl, hexenyl, octenyl, butadienyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, and dienyl. "Branched" refers to a hydrocarbon chain in which a lower hydrocarbon group such as methyl, ethyl or propyl is attached to a linear hydrocarbon chain. "Lower hydrocarbon group" refers to a hydrocarbon group having 1 to about 8 carbon atoms, such as 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms or having up to about 5 carbon atoms (i.e., C 1-8alkyl). “Higher alkyl” refers to alkyl groups 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” specifically refers to C 1-8 In other embodiments, "alkyl" refers specifically to C 1-8 Branched chain hydrocarbon.

[0040] The hydrocarbyl group may be optionally substituted with one or more hydrocarbyl substituents ("substituted hydrocarbyl"), which may be the same or different. The term "hydrocarbyl substituent" includes, but is not limited to, hydrocarbyl, substituted hydrocarbyl, halogen, arylamino, acyl, hydroxy, aryloxy, hydrocarbyl, alkylthio, arylthio, aralkyloxy, aralkylthio, carboxyl, alkoxycarbonyl, oxohydrocarbyl, and cyclohydrocarbyl. In some embodiments, one or more oxygen, sulfur, or substituted or unsubstituted nitrogen atoms may be optionally inserted along the hydrocarbyl chain, wherein the nitrogen substituent is hydrogen, lower hydrocarbyl (also referred to herein as "alkylaminoalkyl"), or aryl.

[0041] Thus, as used herein, the term "substituted hydrocarbyl" includes hydrocarbyl groups as defined herein wherein one or more atoms or functional groups of the hydrocarbyl group are replaced with another atom or functional group including, for example, hydrocarbyl, substituted hydrocarbyl, halogen, aryl, substituted aryl, hydrocarbyloxy, hydroxy, nitro, amino, alkylamino, dialkylamino, sulfate, and mercapto.

[0042] As used herein, the term "aryl" refers to an aromatic substituent, which can be a single aromatic ring, or 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 can also be a carbonyl (such as in benzophenone) or oxygen (such as in diphenyl ether) or nitrogen (such as in diphenylamine). The term "aryl" specifically includes heterocyclic aromatic compounds. The aromatic ring can include phenyl, naphthyl, biphenyl, diphenyl ether, diphenylamine and benzophenone, etc. In a specific embodiment, the term "aryl" refers to a cyclic aromatic compound containing about 5 to about 10 carbon atoms, such as 5, 6, 7, 8, 9 or 10 carbon atoms, and includes 5- and 6-membered hydrocarbons and heterocyclic aromatic rings.

[0043] Aryl groups may be optionally substituted with one or more aryl substituents ("substituted aryl") which may be the same or different, wherein "aryl substituents" include hydrocarbyl, substituted hydrocarbyl, aryl, substituted aryl, aralkyl, hydroxy, hydrocarbyloxy, aryloxy, aralkyloxy, carboxyl, acyl, halogen, nitro, alkoxycarbonyl, aryloxycarbonyl, aralkyloxycarbonyl, acyloxy, acylamino, arylamido, carbamoyl, alkylcarbamoyl, dialkylcarbamoyl, arylthio, alkylthio, alkylene, and -NR'R", wherein R' and R" may each independently be hydrogen, hydrocarbyl, substituted hydrocarbyl, aryl, substituted aryl, and aralkyl.

[0044] Thus, as used herein, the term "substituted aryl" includes aryl groups as defined herein wherein one or more atoms or functional groups of the aryl group are replaced by another atom or functional group including, for example, hydrocarbyl, substituted hydrocarbyl, halogen, aryl, substituted aryl, hydrocarbyloxy, hydroxy, nitro, amino, alkylamino, dialkylamino, sulfate, and mercapto.

[0045] 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.

[0046] As used herein, "heteroaryl" refers to an aryl group containing 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, and the like.

[0047] As used herein, the term "monovalent" refers to a radical of a specified chemical group having one site for attachment to another chemical group.

[0048] As used herein, the term "divalent" refers to a diradical of a designated chemical group that is linked to two other chemical groups. Thus, for example, a "divalent" group can serve as a linking group between two other chemical functional groups.

[0049] "Alkylene" refers to a straight or branched divalent aliphatic hydrocarbon group having 1 to about 20 carbon atoms, such as 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 can be straight chain, branched or cyclic. The alkylene group can also be optionally unsaturated and / or substituted with one or more "hydrocarbyl substituents", along which one or more oxygen, sulfur, or substituted or unsubstituted nitrogen atoms (also referred to herein as "alkylaminoalkyl") can be optionally inserted, wherein the nitrogen substituent is a hydrocarbyl as described above. Exemplary alkylene groups include methylene (-CH2-); ethylene (-CH2-CH2-); propylene (-(CH2)3-); cyclohexyl (-CH6H 10 -);-CH=CH-CH=CH-;-CH=CH-CH2-;-(CH2) q -N(R)-(CH2) r -, wherein q and r are each independently an integer from 0 to about 20, such as 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 a lower hydrocarbon group; methylenedioxy (-O-CH2-O-); and ethylenedioxy (-O-(CH2)2-O-). The alkylene group can have from about 2 to about 3 carbon atoms, and can also have 6-20 carbons.

[0050] "Arylene" refers to a divalent aromatic group.

[0051] "Aralkyl" means 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, phenethyl, and naphthylmethyl.

[0052] "Aralkylene" refers to a divalent group comprising arylene and alkylene portions.

[0053] As used herein, the term "acyl" refers to a carboxylic acid group in which the -OH of the carboxylic acid group is replaced by another substituent. Thus, an acyl group can be represented by RC(=O)-, where R is H, a hydrocarbyl, a substituted hydrocarbyl, an aralkyl, a substituted aralkyl, an aryl, or a substituted aryl group, as defined herein. Specific examples of acyl groups include formyl (i.e., -C(=O)H), acetyl, and benzoyl.

[0054] The terms "hydroxy" and "hydroxyl" refer to the -OH group.

[0055] The term "polyol" refers to a compound containing more than one or more than two hydroxyl groups.

[0056] The term "phenol" as used herein may refer to a compound of the formula R-OH group, wherein R is an aryl or substituted aryl group. Thus, the term "phenolic" refers to a hydroxyl group directly attached to an aromatic group (e.g., a benzene ring, a naphthalene ring, etc.).

[0057] The term "hydrocarbyloxy" refers to a -OR group where R is a hydrocarbyl or substituted hydrocarbyl.

[0058] The term "aryloxy" refers to a -OR group where R is aryl or substituted aryl.

[0059] The term "mercapto" or "thiol" refers to a -SH group.

[0060] The term "carboxy" refers to a -C(=O)- group.

[0061] The terms "carboxylate" and "carboxylic acid" may refer to the groups -C(=O)O- and -C(=O)OH, respectively. In some embodiments, "carboxylate" may refer to a -C(=O)O- or -C(=O)OH group.

[0062] The terms "amide" and "amido" may refer to the group -C(=O)-NR1R2, where R1 and R2 are independently H, hydrocarbon, substituted hydrocarbon, aralkyl, substituted aralkyl, aryl or substituted aryl. The polyamide may include a -C(=O)-NR1- linker in the polymer chain.

[0063] The terms "carbamate" and "urethane" refer to the group -OC(=O)-NR-, where R is H, hydrocarbyl, substituted hydrocarbyl, aralkyl, substituted aralkyl, aryl, or substituted aryl.

[0064] The term "urea" refers to the group -NR1-C(=O)-NR1-, wherein each R1 is independently H, hydrocarbyl, substituted hydrocarbyl, aralkyl, substituted aralkyl, aryl or substituted aryl.

[0065] The term "ester" refers to a compound that includes the group -C(=O)-OR, where R is a hydrocarbon group, an aralkyl group, or an aryl group. A polyester may include a -C(=O)-O- linking group in the polymer chain. Thus, the term "polyester" may refer to a polymer that includes an ester linking group in the polymer backbone.

[0066] The term "ether" refers to a compound that includes the group -ROR-, where each R is an alkylene or arylene group.

[0067] As used herein, the terms "epoxy," "epoxide," and "oxirane" refer to a chemical functional group that includes a three-membered ring structure comprising an oxygen atom and two carbon atoms linked together by a single bond. Thus, an epoxy group may have the following structure:

[0068]

[0069] The term "arylsulfonyl" as used herein refers to an aryl-S(=O)2-group, wherein the aryl group may be optionally substituted with one or more aryl substituents. The term "arylsulfonyl derivative" as used herein may refer to a compound or group in which another chemical functional group (e.g., amide, urea, carbamate, oxo group, etc.) is directly attached to the sulfur atom of the arylsulfonyl group.

[0070] The term "silyl" refers to a group containing a silicon atom (Si). For example, a silyl group may have the formula -Si(R)3, wherein each R is selected from H, a hydrocarbyl group, an aralkyl group, and an aryl group. An exemplary silyl group is a trihydrocarbylsilyl group, such as trimethylsilyl.

[0071] As used herein, the terms "siloxy" and "silyl ether" refer to groups or compounds containing silicon-oxygen (Si-OR) bonds, and wherein R is an organic group such as a substituted or unsubstituted hydrocarbon or aryl group (i.e., methyl, ethyl, phenyl, etc.). In some embodiments, the term refers to a compound containing one, two, three, or four hydrocarbonoxy, aralkoxy, or aryloxy groups bonded to a silicon atom. Each hydrocarbonoxy, aralkoxy, or aryloxy group may be the same or different.

[0072] The term "polysiloxane" refers to a polymer comprising a backbone having alternating silicon and oxygen atoms, wherein the silicon atoms are substituted with functional groups such as hydrocarbyl, aralkyl or aryl groups.

[0073] As used herein, the terms "microparticles" and "nanoparticles" have the meanings that those of ordinary skill in the art will attribute to them. In some embodiments, "microparticles" can refer to particles with a dimension (e.g., width or diameter) ranging from about 1000 microns to about 0.1 microns. In some embodiments, microparticles have a dimension ranging from about 100 microns to about 1 micron. In some embodiments, "nanoparticles" refer to particles with a dimension ranging from about 1 micron to about 0.1 nm. In some embodiments, nanoparticles have a dimension of about 500 nm to about 1 nm. In some embodiments, nanoparticles have a dimension less than about 200 nm, such as, but not limited to, about 100 nm. Microparticles and nanoparticles can be in any shape, such as, cube, spherical or irregular shape.

[0074] As used herein, "monomer" or "polymerizable monomer" refers to a molecule that can undergo polymerization to contribute a structural unit (ie, a repeating atom or group of atoms) to the basic structure of a polymer or oligomer.

[0075] As used herein, "polymer" refers to a molecule comprising multiple repeating units, the repeating units being derived from molecules of low relative molecular mass, such as polymerizable monomers and / or oligomers. In some embodiments, the polymer has at least 10, at least 50, or at least 100 repeating units.

[0076] "Oligomer" refers to a polymer molecule of medium relative molecular mass whose structure includes a small number (eg, 2-10) of units derived from molecules of lower relative molecular mass.

[0077] "Copolymer" refers to a polymer derived from more than one polymerizable monomer. Copolymers include block copolymers (containing oligomer or polymer chains, wherein each chain is based on an oligomer or polymer chain of a different monomer unit), random copolymers (wherein the monomer units from the different monomers are randomly arranged in the copolymer), and statistical copolymers (wherein the monomer units from the different monomers have a statistical distribution in the copolymer chain).

[0078] A polymer blend is a mixture of two different types of polymers or copolymers.

[0079] A "chain" refers to all or part of a polymer or oligomer comprising a linear or branched sequence of structural units between two boundary structural units, wherein the two boundary structural units may contain end groups, branching points, or a combination thereof. A "main chain" or "backbone" refers to the chain from which all other chains are considered to be suspended. A "side chain" refers to a smaller chain connected to the main chain. In some embodiments, a side chain may comprise a single non-repeating structural unit.

[0080] As used herein, the terms "resin" and "polymer resin" refer to reactive and non-reactive resins. For example, the term resin may refer to a composition comprising a monomer, an oligomer, a polymer or a mixture thereof, which composition may be converted, for example, by a hardening or curing process to form a more rigid polymer matrix. The resin may include a viscous substance or a mixture of viscous substances. Additionally or alternatively, the resin may include one or more compounds, which may be dissolved in another resin component or in a solvent, which may be evaporated or otherwise removed during and / or after the hardening or curing process. Therefore, in some embodiments, the term resin refers to a composition comprising a polymerizable monomer, which is liquid or soluble in a suitable solvent at a temperature and / or pressure (e.g., room temperature and atmospheric pressure) configured before the resin is hardened or cured. The term resin may also refer to such oligomers and / or polymers, which may undergo cross-linking reactions and / or additional polymerization to form higher molecular weight compounds. The term resin may also refer to a non-reactive resin that cannot form covalent bonds by polymerization or cross-linking. This non-reactive resin may include one or more oligomers or polymer species.

[0081] As used herein, the term "organic solvent" may refer to polar and nonpolar aprotic solvents commonly used in the field of organic synthesis, and contains one or more carbon atoms. The term "aprotic solvent" refers to a solvent molecule that can neither accept nor provide a proton. Examples of aprotic solvents include, but are not limited to: ethyl acetate; carbon disulfide; 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 symmetrical halogenated hydrocarbons such as carbon tetrachloride, tetrachloroethane and dichloromethane. Other aprotic solvents include (for example) acetone, acetonitrile, butanone, butyronitrile, chlorobenzene, chloroform, 1,2-dichloroethane, dimethylacetamide, N,N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO) and 1,4-dioxane.

[0082] II. Representative Implementation Schemes

[0083] In some embodiments, the subject matter of the present disclosure provides a family of compounds, which can be used as compatibilizers in multiple applications. For example, compounds of the present disclosure can be used as surfactants, emulsifiers, foaming agents, adhesion promoters, wetting agents and / or dispersants. In some embodiments, compounds of the present disclosure can be used to change the viscosity of liquid mixtures and / or suspensions, and the mixtures and / or suspensions are, for example, paints, coatings, inks, cleaning solutions, cosmetics or emollients, lubricants (such as high temperature lubricants, compressor lubricants, refrigeration lubricants, mechanical lubricants, dual-cycle lubricants, rubber lubricants, mills and calender lubricants, grease and solid lubricants, textile fiber lubricants, textile machinery lubricants, etc.), magnetorheological fluids, adhesives or drilling fluids. In some embodiments, the compound can be used to change the coefficient of friction (COF) of liquids and solids.

[0084] In the exemplary embodiments described herein, the compatibilizers of the 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 used to prepare highly filled thermally conductive urethanes. In addition to having improved viscosity reduction compared to surfactants commonly used in such systems, the compatibilizers of the present disclosure can also improve the shelf life and cure stability of the urethane and provide for the use of high concentrations of fillers, including lower cost fillers and / or fillers with higher surface areas. However, the compatibilizers 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.

[0085] In some embodiments, the compatibilizer of the present disclosure may be the reaction product of (i) an amine, alcohol, or carboxylic acid and (ii) an aryl isocyanate such as p-toluene isocyanate (PTI) or an aryl sulfonyl isocyanate such as p-toluenesulfonyl isocyanate (PTSI). Thus, for example, the compatibilizer may include one or more first groups, wherein the one or more first groups are selected from aromatic sulfonylcarbamates (i.e., groups having the formula: aromatic-S(=O)2-NH-C(=O)-O-), aromatic sulfonylureas (i.e., groups having the formula: aromatic-S(=O)2-NH-C(=O)-NH-), aromatic sulfonylamides (i.e., groups having the formula: aromatic-S(=O)2-NH-C(=O)-), aromatic sulfonamides (i.e., groups having the formula: aromatic-S(=O)2-NH-), aromatic sulfonates (i.e., groups having the formula: aromatic-S(=O)2-O-) and aromatic carbamates (i.e., groups having the formula: aromatic-NH-C(=O)-O-) and aromatic ureas (i.e., groups having the formula: aromatic-NH-C(=O)-NH-). Figures 1A-1DSynthesis schemes for synthesizing exemplary compatibilizers of the disclosed subject matter are shown, which are prepared by reacting PTSI and various monols (or "monols"). In some embodiments, PTSI and monols (or other alcohols) may be contacted with one another under conditions to form a compatibilizer, wherein the ratio of isocyanate (NCO) equivalents to hydroxyl equivalents (OH) is from about 0.5:1 NCO:OH to about 1.5:1 NCO:OH. For example, in some embodiments, more NCO equivalents than OH equivalents may be used to offset possible reaction of NCO groups with residual water that may be present in the monol. In some embodiments, the NCO:OH ratio may be about 1:1. When an aromatic isocyanate is reacted with an amine or carboxylic acid rather than an alcohol, a ratio of about 0.5:1 NCO:reactive group to about 1.5:1 NCO:reactive group may be used. Figure 2 The general chemical structure of the compatibilizer of the presently disclosed subject matter is shown, illustrating different types of first group functional groups where the aryl group is a methyl-substituted phenyl group.

[0086] 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, wherein each of the one or more second groups is connected to at least one of the one or more first groups. One or more first groups may provide interactions between a compatibilizer and a polar surface (e.g., a polar surface of an inorganic filler particle) or a polar group in a liquid. For example, in some embodiments, the first group may interact with the inorganic filler particles via a π bond between a metal ion in the inorganic filler and an aromatic moiety of the first group and / or via a hydrogen bond and / or dipole interaction between an inorganic filler and a heteroatom in the first group. One or more second groups may be selected based on the intended use of the compatibilizer. For example, in some embodiments, in the case of using a compatibilizing group (e.g.) in a liquid matrix to enhance the interaction between the compatibilizer and the liquid matrix, the second group chemical composition may be customized to have a chemical composition similar to one or more components of the liquid matrix, or otherwise compatible with one or more components of the liquid matrix. In some embodiments, one or more second groups may include a hydrocarbon group (e.g., a hydrocarbon group from a fatty acid or a fatty alcohol), a polymer group or an oligomer group, or any combination thereof. In some embodiments, the polymer portion of the second group is selected from polyethers, polysiloxanes, polyacrylates, polyesters, and polyolefins.

[0087] The first group and the second group of the compatibilizer of the present disclosure can be provided in various configurations. Exemplary configurations of the first group (B) and the second group (A) are shown in Figure 3 For example, the compatibilizer may include a first group and a second group ( Figure 3AB configuration), two second groups connected to the same first group ( Figure 3 The "ABA configuration" of the first group is connected to the same second group ( Figure 3 A "BAB configuration"), a series of alternating first and second groups (e.g. Figure 3 of "(BA) n B configuration") or a dimeric configuration, wherein two AB configuration subunits are connected to each other by one or more linking groups (e.g., between two first groups or between two second groups) (i.e., Figure 3 The gemini-configuration compatibilizers of the presently disclosed subject matter may include linker chemistries and configurations similar to gemini surfactants known in the art. See, for example, Sekhon, BS (Resonance, 42-49 (2004)).

[0088] In some embodiments, the compatibilizer includes one or more first groups, each of which includes a portion containing an arylsulfonyl derivative. Therefore, in some embodiments, one or more first groups each include an arylsulfonylcarbamate, an arylsulfonylurea, an arylsulfonylamide, an arylsulfonamide, or an arylsulfonate. In some embodiments, the compatibilizer is a compound having a structure of one of formulas (I) to (V):

[0089] A1-X1-Z1(I);

[0090] A1-X1-Z2-X2-A1(II);

[0091] Z1-X2-A2-X1-Z1(III);

[0092] A1-(X1-Z2-X2-A2) n -X1-Z2-X2-A1(IV);

[0093] (A1-X1) p -Z3(V),

[0094] wherein: n is an integer of 1 or greater; p is an integer of 3 or greater; each A1 is an aryl group or a substituted aryl group (e.g., a phenyl group or a substituted phenyl group); each A2 is an arylene group or a substituted arylene group (e.g., a phenylene group or a substituted phenylene group); 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 selected from a hydrocarbon group (e.g., a branched or straight-chain C6-C40 hydrocarbon group) and -(L2) s -(L3) t-R1, wherein s is 0 or 1; t is 0 or 1; L2 is an alkylene group, L3 is a polymeric moiety or an oligomeric moiety, and R1 is a hydrocarbon group or a silyl group; Z2 is an alkylene group, a polymeric moiety, or a combination thereof; and Z3 is a multivalent group derived from a compound including at least three hydroxyl, amino, or carboxylic acid groups (i.e., a multivalent group formed when at least three hydroxyl, amino, or carboxylic acid groups of a parent compound react with a sulfonyl isocyanate group to form an X1 linking group).

[0095] In some embodiments, the compatibilizer can be prepared by reacting an arylsulfonyl isocyanate or an aryldisulfonyl isocyanate with a monofunctional alcohol (i.e., a "monohydric alcohol"), an amine, or a polyol. For example, in some embodiments, the compatibilizer can be prepared by reacting an arylsulfonyl isocyanate (e.g., PTSI) and a polyol (e.g., polyoxyethylene (POE) sorbitan monooleate or another sugar derivative), and the compatibilizer can have a structure of Formula (V):

[0096] (A1-X1) p -Z3(V),

[0097] wherein each A1 is an aryl or substituted aryl group; each X1 is -S(=O)2-NH-C(=O)-O-; p is an integer of 3 or greater, and Z3 is a multivalent derivative of a polyol (i.e., a polyol derivative in which at least three hydroxyl groups of a parent polyol are reacted with a sulfonyl isocyanate group to form an X1 linking group, wherein the oxygen atom of the hydroxyl group of the parent polyol is connected to the oxygen atom of the carboxyl group in the X1 linking group).

[0098] In some embodiments, the compatibilizer includes a first group and a second group and is a compound of formula (I):

[0099] A1-X1-Z1(I);

[0100] wherein: A1 is an aryl group or a substituted aryl group; X1 is -S(=O)2-NH-C(=O)-O-, -S(=O)2-NH-C(=O)-NH- or -S(=O)2-NH-C(=O)-; and Z1 is selected from a hydrocarbon group and -(L2) s -(L3) t -R1, wherein s is 0 or 1; t is 0 or 1; L2 is an alkylene group, L3 is a polymer moiety or an oligomer moiety, and R1 is a hydrocarbyl group or a silyl group. In some embodiments, A1 is phenyl or substituted phenyl (e.g., a hydrocarbyl-substituted phenyl). In some embodiments, A1 is methyl-substituted phenyl.

[0101] In some embodiments, the compatibilizer is a reaction product of p-toluenesulfonyl isocyanate (PTSI) and a monofunctional alcohol (i.e., a monohydric alcohol). Therefore, in some embodiments, X1 is -S(=O)2-NH-C(=O)-O-, and the compatibilizer is a compound including a first group of the formula:

[0102]

[0103] That is, it is referred to as tosyl carbamate herein.

[0104] In some embodiments, Z1 is a hydrocarbon group. In some embodiments, Z1 is a C6-C40 hydrocarbon group (e.g., C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38 or C40 hydrocarbon group). For example, in some embodiments, Z1 is a monovalent derivative of a branched or straight-chain fatty alcohol, such as 3-methylpentanol, heptanol, octanol, nonanol, decanol, undecyl alcohol, lauryl alcohol, tridecanol, myristyl alcohol, pentadecyl alcohol, cetyl alcohol, palmitoleyl alcohol, heptadecanol, stearyl alcohol, oleyl alcohol, nonadecanol, arachidyl alcohol, etc. In some embodiments, Z1 is isostearyl.

[0105] In some embodiments, Z1 is -(L2) s -(L3) t-R1, wherein s is 0 or 1; t is 1; L2 is an alkylene group (e.g., C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11 or C12 alkylene group), L3 is a polymer group, and R1 is a hydrocarbon group or a silyl group. In some embodiments, L3 is a polymer group or an oligomer 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 polysiloxane group. In some embodiments, L3 is a combination of different polymer groups or oligomer groups, that is, wherein L3 may have blocks of two or more different types of polymer groups or oligomer groups. In some embodiments, the polyether is a polyether polyol portion. In some embodiments, the polyether is a polyalkylene glycol portion, such as a polyethylene glycol (PEG) or a polypropylene glycol (PPG) portion. In some embodiments, R1 is a C1-C6 hydrocarbon 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 hydrocarbon group, such as a C8-C40 hydrocarbon group, which can be branched or straight chain, and optionally includes one or more carbon-carbon double bonds. In some embodiments, R1 is a silyl group (e.g., trimethylsilyl). In some embodiments, Z1 is a hydrocarbon-terminated polyether polyol or a silyl-terminated alkylene-polysiloxane moiety (e.g., a C1-C6 alkylene-PDMS moiety, terminated by a hydrocarbon-substituted silyl group such as a trimethylsilyl or hydrocarbon group).

[0106] In some embodiments, the compatibilizer is one of the group consisting of:

[0107]

[0108]

[0109] Wherein 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.

[0110] In some embodiments, the subject matter of the present disclosure provides a composition comprising a compatibilizer and at least one liquid molecule. Therefore, in some embodiments, the subject matter of the present disclosure provides a composition that is compatible 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, which includes (b1) one or more first groups, wherein each of the one or more first groups includes an arylsulfonyl moiety; and (b2) one or more second groups, wherein each of the one or more second groups includes a hydrocarbon moiety, a polymer moiety or an oligomer moiety, or a combination thereof, and each of the one or more second groups is connected to at least one of the one or more first groups); and (c) one or more optional additional ingredients. In some embodiments, the polymer moiety of (b2) is selected from polyethers (e.g., polyether polyols), polysiloxanes, polyacrylates, polyesters, and polyolefins (e.g., polyalphaolefins (PAOs)).

[0111] In some embodiments, the compatibilizer (b) has a structure of one of the above formulas (I) to (V). In some embodiments, the compatibilizer has a structure of formula (I):

[0112] A1-X1-Z1 (I);

[0113] Wherein: A1 is an aryl group or a substituted aryl group; 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 selected from a hydrocarbon group and -(L2) s -(L3) t -R1, wherein s is 0 or 1; t is 0 or 1; L2 is an alkylene group, L3 is a polymeric moiety or an oligomeric moiety, and R1 is a hydrocarbon group or a silyl group. In some embodiments, A1 is a phenyl group or a methyl-substituted phenyl group. In some embodiments, the compatibilizer is a reaction product of PTSI and a monohydric alcohol, an amine, or a carboxylic acid.

[0114] The liquid matrix (a) may include any liquid, solution or liquid mixture that may benefit from the presence of a compatibilizer of the present disclosure, whether the compatibilizer is present alone or in combination with an optional additional component (c), which may be an additional liquid or solid component. In some embodiments, the liquid matrix comprises one or more oligomers or polymers, or is composed of one or more oligomers or polymers. For example, in some embodiments, the liquid matrix comprises or is composed of the following polymers, such as polyethers, polyesters or PAOs (e.g., polyolefins prepared by polymerization of 1-olefins (e.g., 1-hexene or 1-octene), or polyethylene copolymers thereof). In some embodiments, the liquid matrix comprises one or more monomers, such as amines, alcohols, isocyanates, polyols 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 a combination thereof. In some embodiments, the liquid matrix comprises a hydrocarbon fluid. In some embodiments, the liquid matrix may comprise any combination of these liquids and / or include one or more solutes, such as, for example, dyes or other colorants, antioxidants, UV stabilizers, polymerization catalysts, and the like.

[0115] For example, in some embodiments, the liquid matrix includes a reactive or non-reactive resin. In some embodiments, the resin includes a monomeric compound and a polymeric compound and / or an oligomeric compound, wherein the compound is liquid at a temperature and / or pressure suitable for the application or use of the resin, or wherein the compound is soluble in a suitable solvent so that the resin compound can be provided in the form of a solution. In some embodiments, the resin includes a compound that is liquid at room temperature or soluble in a solvent at room temperature. In some embodiments, the liquid matrix includes a urethane resin, a silicone resin, an acrylic resin, an epoxy resin, or a silyl-terminated resin.

[0116] More particularly, suitable liquid epoxy resins can include epoxy materials containing at least one epoxy functional group. Epoxy resins can be monofunctional, difunctional, multifunctional and combinations thereof. Epoxy resins can be aliphatic, alicyclic, aromatic, etc. In some embodiments, epoxy resins include liquid epoxy resins based on diglycidyl ether of bisphenol A (DGEBA) or diglycidyl ether of bisphenol F (DGEBF). Liquid epoxy resins generally include less than about 500 daltons and preferably a molecular weight between about 150 daltons and 600 daltons. Molecular weight can be measured by methods known in the art, such as by gel permeation (or size exclusion) chromatography.

[0117] Acrylic resin can include acrylic materials containing at least one acrylate and / or methacrylate functional group.Acrylic resin can be monofunctional, difunctional, multifunctional or a combination thereof, as long as the resulting material blend is liquid at room temperature.Representative monofunctional acrylic resin includes (meth) acrylic acid esters, 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 (meth) 3-hydroxypropyl acrylate, (meth) 4-hydroxybutyl acrylate, (meth) 4-hydroxycyclohexyl acrylate, mono(meth) 1,6-hexanediol ester, mono(meth) neopentyl glycol ester.

[0118] In some embodiments, the composition comprises one or more optional additional ingredients (c). In some embodiments, the one or more optional additional ingredients include 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 weight (wt) % to about 95 wt % of one or more additional solid ingredients or from about 1 volume (vol) % to about 80 vol % of one or more optional additional solid ingredients. For example, a "highly filled" resin may comprise from about 35 wt % to about 95 wt % of solid filler particles and / or fibers. Thus, in some embodiments, the composition comprises about 35 wt% to about 95 wt% (e.g., about 35 wt%, about 40 wt%, about 45 wt%, about 50 wt%, about 55 wt%, about 60 wt%, about 65 wt%, about 70 wt%, about 75 wt%, about 80 wt%, about 85 wt%, about 90 wt%, or about 95 wt%) of solid filler particles or fibers, or a combination of solid filler particles and / or fibers (e.g., wherein the combination may include particles of different sizes of the same chemical composition, a combination of particles of different chemical compositions, or a combination of particles of different chemical compositions and different sizes). In some embodiments, the composition comprises about 65 wt% to about 90 wt% of solid filler particles or fibers, or a combination of solid filler particles and / or fibers. In some embodiments, (c) includes particles and / or fibers, including but not limited to one or more particles and / or fibers of the group consisting of silica, fumed silica, fused silica, talc, mica, wollastonite, calcium carbonate, carbon, polymers, aluminum, aluminum trihydrate (ATH), iron, silver, metal oxides, boron nitride, and aluminum nitride.

[0119] In some embodiments, the optional additional ingredient (c) comprises an additional liquid ingredient, for example, wherein the additional liquid ingredient 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 liquid). In some embodiments, (a) comprises a non-polar liquid and (c) comprises water. In some embodiments, when (c) comprises a liquid ingredient, (c) comprises at least about 1 wt % but less than about 50 wt % (or less than about 40 wt %, less than about 30 wt %, less than about 25 wt %, less than about 20 wt %, less than about 15 wt % or less than about 10 wt %) of the total weight of the composition.

[0120] In some embodiments, compatibilizer (b) has the structure of formula (I):

[0121] A1-X1-Z1 (I);

[0122] Wherein: A1 is an aryl group or a substituted aryl group; 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 selected from a hydrocarbon group and -(L2) s -(L3) t -R1, wherein s is 0 or 1; t is 0 or 1; L2 is an alkylene group, L3 is a polymeric or oligomeric moiety, and R1 is a hydrocarbyl group or a silyl group. In some embodiments, A1 is phenyl or substituted phenyl. In some embodiments, A1 is a hydrocarbyl-substituted phenyl group (e.g., a methyl-substituted phenyl group).

[0123] In some embodiments, Z1 is a hydrocarbon group. In some embodiments, Z1 is a C6-C40 hydrocarbon group (e.g., C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38 or C40 hydrocarbon group). For example, in some embodiments, Z1 is a monovalent derivative of a branched or straight-chain fatty alcohol, such as 3-methylpentanol, heptanol, octanol, nonanol, decanol, undecyl alcohol, lauryl alcohol, tridecanol, myristyl alcohol, pentadecyl alcohol, cetyl alcohol, palmitoleyl alcohol, heptadecanol, stearyl alcohol, oleyl alcohol, nonadecanol, arachidyl alcohol, etc. In some embodiments, Z1 is isostearyl.

[0124] In some embodiments, a compatibilizer having a hydrocarbon group is provided in the composition, wherein (a) includes a resin, such as an epoxy resin or a resin containing an isocyanate. In some embodiments, a compatibilizer having a hydrocarbon group is present in the composition, wherein (a) includes PAO or water. In some embodiments, when there is an optional additional component (c) such as organic and / or inorganic particles or fibers (such as ATH or iron particles), a compatibilizer having a hydrocarbon group is included in the composition. In some embodiments, when there is no optional additional component (c), a compatibilizer having a hydrocarbon group is present in the composition.

[0125] In some embodiments, Z1 is -(L2) s -(L3) t -R1, wherein s is 0, t is 1, L3 is a polyether polyol, and R1 is a hydrocarbon group (e.g., a C1-C6 hydrocarbon group). Thus, for example, Z1 may include a polyether polyol portion, such as a polypropylene portion terminated by a lower hydrocarbon group (e.g., a methyl, ethyl, propyl, or butyl group). In some embodiments, when (a) includes a polyol, there is a compatibilizer in which Z1 includes a polyether polyol in the composition. In some embodiments, the composition further includes organic and / or inorganic particles and / or fibers.

[0126] In some embodiments, Z1 is -(L2) s -(L3) t -R1, wherein s is 1, t is 1, L2 is an alkylene group (e.g., a C1-C6 alkylene group, optionally including an oxygen atom inserted into the alkylene group), L3 is a polysiloxane moiety, and R1 is a silyl group (e.g., a trialkylsilyl group). In some embodiments, when (a) includes PDMS, a compatibilizer in which L3 includes a polysiloxane moiety may be used in the composition. In some embodiments, the composition further includes solid particles and / or fibers, such as ATH particles.

[0127] In some embodiments, the compatibilizer has the structure of Formula (Ia):

[0128]

[0129] Wherein Z1 is selected from hydrocarbon groups and -(L2) s -(L3) t -R1, wherein s is 0 or 1; t is 0 or 1; L2 is an alkylene group, L3 is a polymeric moiety or an oligomeric moiety, and R1 is a hydrocarbon group or a silyl group.

[0130] In some embodiments, the composition comprises one of the compositions selected from the group consisting of (i) to (vi), wherein:

[0131] (i) A1 is a methyl-substituted phenyl group, X1 is -S(=O)2-NH-C(=O)-O-, and Z1 is -(L2) s -(L3) t -R1, wherein s is 0, t is 1, L3 is a polyether polyol moiety, and R1 is methyl; the liquid matrix (a) comprises a polyether polyol; and the optional additional component (c) comprises one or more organic and / or inorganic particles (e.g., ATH particles);

[0132] (ii) A1 is a methyl-substituted phenyl group, X1 is -S(=O)2-NH-C(=O)-NH-, and Z1 is -(L2) s -(L3) t -R1, wherein s is 0, t is 1, L3 is a polyether polyol, and R1 is a methyl group; the liquid matrix (a) comprises a polyether polyol; and the optional additional component (c) comprises one or more organic and / or inorganic particles (e.g., ATH particles);

[0133] (iii) A1 is a methyl-substituted phenyl group, X1 is -S(=O)2-NH-C(=O)-O-, and Z1 is isostearyl; the liquid matrix (a) comprises PAO; and the optional additional component (c) comprises one or more organic and / or inorganic particles (e.g., iron particles);

[0134] (iv) A1 is phenyl substituted with methyl, X1 is -S(=O)2-NH-C(=O)-O-, and Z1 is -(L2) s -(L3) t -R1, wherein s is 1, t is 1, L2 is -CH2CH2-OCH2CH2CH2-, L3 is a PDMS moiety, and R1 is a silyl group; the liquid matrix (a) comprises a silicone resin; and the optional additional component (c) comprises one or more organic and / or inorganic particles (e.g., ATH particles);

[0135] (v) A1 is a methyl-substituted phenyl group, X1 is -S(=O)2-NH-C(=O)-O-, and Z1 is isostearyl; the liquid matrix (a) comprises an isocyanate (e.g., HDMI); and the optional additional component (c) comprises one or more organic and / or inorganic particles (e.g., ATH particles); and

[0136] (vi) A1 is methyl-substituted phenyl, X1 is -S(=O)2-NH-C(=O)-O-, and Z1 is polyoxyethylene (5) oleyl ether; and wherein the liquid matrix (a) comprises water; and the optional additional component (c) comprises PAO.

[0137] As described above, the compositions of the disclosed subject matter can be used in a variety of different applications. In some embodiments, the composition is selected from the group consisting of, but not limited to, paints, coatings, cleaning solutions, lubricants, magnetorheological fluids, adhesives, drilling fluids, cosmetics, and inks.

[0138] In some embodiments, the subject matter of the present disclosure provides a method for changing the viscosity of a polymer resin (or other liquid) composition, wherein the method includes contacting a composition comprising a polymer resin (or other liquid) with a compatibilizer of the subject matter of the present disclosure (e.g., a compatibilizer comprising one or more first groups and one or more second groups, wherein each of the one or more first groups comprises an arylsulfonyl moiety, wherein each of the one or more second groups comprises a hydrocarbon group, a polymer group, or a combination thereof, and wherein each of the one or more second groups is connected to at least one of the one or more first groups). In some embodiments, the compatibilizer has a structure of one of formulas (I) to (V) as described above. In some embodiments, the compatibilizer has a structure of formula (I). In some embodiments, the compatibilizer has a structure of formula (Ia).

[0139] In some embodiments, the polymer resin includes a polyol, an isocyanate, an amine, a polysiloxane, a PAO, an epoxy resin, an acrylic resin, or a combination thereof.

[0140] In some embodiments, the polymer resin is a filled polymer resin, i.e., as described above, comprising solid organic and / or inorganic particles and / or fibers (e.g., microparticles and / or nanoparticles and / or nanofibers comprising one or more of silica, fumed silica, fused silica, talc, mica, wollastonite, calcium carbonate, carbon black, carbon fiber, polymer fiber, aluminum, aluminum trihydrate (ATH), iron, silver, metal oxides, boron nitride, and aluminum nitride). In some embodiments, the polymer resin composition comprises about 35 wt% to about 95 wt% of solid organic and / or inorganic particles and / or fibers.

[0141] In some embodiments, altering the viscosity of a polymeric resin (or other liquid composition) includes, for example, reducing the viscosity of a polymeric resin (or other composition) compared to the same composition in the absence of a compatibilizer. In some embodiments, the viscosity is reduced compared to the viscosity of the same composition containing a conventional surfactant or other type of compatibilizer instead of the compatibilizer of the presently disclosed subject matter.

[0142] Although the compatibilizers of the disclosed subject matter can generally be selected to reduce viscosity, in some embodiments, the compatibilizers can be selected to impart shear-thinning or thixotropic rheological behavior to the resin or other composition. In some embodiments, the compatibilizer can be selected to increase viscosity, for example by selecting a compatibilizer having one or more second groups having a structure that is different from and / or immiscible or partially miscible with the liquid matrix.

[0143] In some embodiments, the subject matter of the present disclosure provides a method for preparing polyurethane. In some embodiments, the method includes contacting a composition comprising a polyol and / or an isocyanate resin with a compatibilizer of the subject matter of the present disclosure (for example, wherein the compatibilizer includes: one or more first groups, wherein each of the one or more first groups includes an arylsulfonyl moiety; and one or more second groups, wherein each of the one or more second groups includes a hydrocarbon moiety, a polymer moiety, or a combination thereof, and wherein each of the one or more second groups is connected to at least one of the one or more first groups). In some embodiments, the compatibilizer has the structure of one of formulas (I) to (V) as described above. In some embodiments, the compatibilizer has the structure of formula (I). In some embodiments, the compatibilizer has the structure of formula (Ia).

[0144] Polyurethanes can be prepared, for example, by reacting an isocyanate (e.g., a diisocyanate) with a polyol (e.g., a difunctional polyol) to prepare an isocyanate-terminated prepolymer. In some embodiments, polyurethanes can be prepared by directly reacting an isocyanate with a polyol without forming a prepolymer. Suitable isocyanates for preparing polyurethanes according to the subject matter of the present disclosure include, but are not limited to, aromatic, aliphatic, and alicyclic polyisocyanates, for example, isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), methylene bis(phenyl diisocyanate) (MDI), 4,4'-methylene dicyclohexyl diisocyanate (HMDI or H 12 The invention also provides monomeric alicyclic isocyanates, meta-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'-dimethoxy-4,4'-biphenylene diisocyanate, 3,3'-dimethyldiphenylmethane-4,4'-diisocyanate, 4,4',4"-triphenylmethane diisocyanate, polymethylene polyphenyl isocyanate, toluene-2,4,6-triisocyanate and 4.4'-dimethyldiphenylmethane-2,2',5,5'-tetraisocyanate and polymeric MDI, and mixtures and blends thereof.

[0145] Suitable polyols include compounds such as, but not limited to, alkylene glycols (e.g., ethylene glycol, propylene glycol, 1,4-butanediol, 1,6-hexanediol, etc.), glycol ethers and polyethers, such as difunctional polyether polyols, such as diethylene glycol, triethylene glycol, dipropylene glycol, tripropylene glycol, etc., glycerol, trimethylolpropane, tertiary amine-containing polyols, such as triethanolamine, triisopropanolamine, and ethylene oxide and / or propylene oxide adducts of ethylenediamine, toluenediamine, etc., polyether polyols, carbonates, etc., and mixtures and blends thereof. Polyester polyols are also suitable, including reaction products of polyols (e.g., diols) with polycarboxylic acids or their anhydrides (e.g., dicarboxylic acids or dicarboxylic anhydrides). The polycarboxylic acids or anhydrides may be aliphatic, alicyclic, aromatic and / or heterocyclic, and may be optionally substituted, such as by halogen atoms. The polycarboxylic acids 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.

[0146] In some embodiments, the composition comprises isocyanate and polyol. The ratio of the two components can be selected to provide the desired isocyanate index (ratio of isocyanate to isocyanate reactive groups (e.g., hydroxyl groups of polyol)). In some embodiments, the isocyanate and polyol components are mixed so that the isocyanate to hydroxyl (NCO:OH) equivalent index is from 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 may further include a catalyst, such as an amine catalyst or an organometallic catalyst (e.g., a tin-containing organometallic catalyst).

[0147] In some embodiments, the method further comprises contacting the composition comprising polyol and / or isocyanate resin with one or more organic and / or inorganic filler particles (e.g., micronized particles 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, silica, fumed silica, fused silica, talc, mica, wollastonite, calcium carbonate, carbon black, carbon fiber, polymer fiber, aluminum, aluminum trihydrate (ATH), iron, silver, metal oxides, boron nitride, and aluminum nitride. In some embodiments, the method may comprise contacting the composition comprising polyol and / or isocyanate with more than one type of organic or inorganic filler particles or with more than one size of organic or inorganic filler particles.

[0148] In some embodiments, a compatibilizer is contacted with a composition comprising a polyol and / or an isocyanate resin, and the amount of the compatibilizer is about 0.05 wt% to 49 wt% based on the total weight of the liquid of the composition comprising the polyol and / or isocyanate resin and the compatibilizer. In some embodiments, a compatibilizer is contacted with a polyol and / or an isocyanate resin, and the amount of the compatibilizer is about 0.5 wt% to about 12 wt% (e.g., about 0.5 wt%, 1.0 wt%, 1.5 wt%, 2.0 wt%, 2.5 wt%, 3.0 wt%, 4.0 wt%, 5.0 wt%, 6.0 wt%, 7.0 wt%, 8.0 wt%, 9.0 wt%, 10.0 wt%, 11.0 wt%, or about 12.0 wt%) based on the total weight of the liquid of the composition comprising the polyol and / or isocyanate resin and the compatibilizer. In some embodiments, the compatibilizer is contacted with the polyol and / or isocyanate resin in an amount of about 0.5 wt % to about 3.0 wt % 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 wt % to about 2 wt % based on the total weight of the composition.

[0149] When used to replace conventional surfactants or other types of compatibilizers for resins containing polyols and / or isocyanates, the compatibilizers of the present disclosure can provide many advantages. For example, in view of the lack of reactivity of the compatibilizers of the present disclosure, improved stability can be provided. Acidic esters (such as acidic esters traditionally used for these types of resins) will react with isocyanate groups undesirably and will therefore cause increased viscosity and shortened resin shelf life. The compatibilizers of the present disclosure can also have less interaction with the catalysts used in these resins. On the contrary, the acidic esters will complex with the catalysts, thereby inhibiting or delaying curing. The improved efficiency obtained by using the compatibilizers of the present disclosure can also cause less plasticization of the resulting cured polyurethane matrix. Plasticization may be undesirable because it may impair the mechanical properties of the polyurethane. In addition, the compatibilizers of the present disclosure can provide higher filler loadings and / or use fillers with higher surface areas. The compatibilizers of the present disclosure are also easy to synthesize. For example, the reaction of PTSI and monohydric alcohols is fast and there are no obvious by-products.

[0150] Some of the improved effects of the compatibilizer disclosed in the present invention are shown in Figures 4 to 8 For example, Figure 4 The effect of the amount of compatibilizer of the disclosed subject matter on the viscosity of a polyol resin (i.e., a polypropylene glycol (PPG) resin) highly filled with 79 wt% ATH particles at the same shear rate is shown. Figure 5 Shown is the effect of different compatibilizers of the disclosed subject matter on the viscosity of the same filled resin system at different shear rates. Figure 5The compatibilizers have various "second groups" based on, for example, hydrocarbon-terminated PPG monools (Example 1), amine derivatives of PPG (Example 3), polyoxyethylene (POE) (4) lauryl ether (Example 4) and POE (20) sorbitan monooleate (Example 5). Figures 6 to 8 The effect of exemplary compatibilizers of the disclosed subject matter on viscosity in different liquid matrices, namely highly filled hydrogenated MDI resin ( Figure 6 ), filled with PAO fluid ( Figure 7 ) and vinyl terminated PDMS resin ( Figure 8 The flat-Newtonian behavior of the formulations containing compatibilizers reflects the strong ability of the compatibilizers to wet the fillers and disperse the fillers in the liquid matrix.

[0151] Example

[0152] The following examples are included to further illustrate various embodiments of the subject matter of the present disclosure. However, those of ordinary skill in the art will appreciate from this disclosure that many changes may be made to the specific embodiments disclosed without departing from the spirit and scope of the subject matter of the present disclosure and still obtain the same or similar results.

[0153] Example 1-Example 8

[0154] A series of compatibilizers of the examples were prepared. The reactants used to prepare the compatibilizers and their corresponding weight percentages in the different compatibilizers are summarized in Table 1 below. The example compatibilizers were synthesized according to the following general procedure:

[0155] Reactant A was added to a 60 mL glass bottle equipped with a magnetic stirring bar and a dry nitrogen inlet / outlet flow line. Reactant B was then gradually added over the course of approximately 30 minutes while reactant A was stirred under a steady stream of dry nitrogen. The amount of reactant B was based on the stoichiometric portion of the reactive group, with a total final target mass of 20 g. After the reaction was complete, stirring was continued for at least another 60 minutes, with the completion of the reaction verified by Fourier transform infrared (FTIR) spectroscopy.

[0156] Table 1. Exemplary compatibilizers.

[0157]

[0158] Example 9-Example 30

[0159] Table 2 provides a summary of control and exemplary formulations to illustrate the ability of specific compatibilizers to reduce viscosity. Molecular sieve powder (particle size = 5 microns, mesh diameter = 4 angstroms) was used in selected formulations to remove any water introduced by the liquid resin and / or filler. The compatibilizers were mixed using a DAC 800 Hauschild SpeedMixer according to the weight percentages listed in Table 2. TM The formulations were prepared by mixing the ingredients under vacuum (Hauschild GmbH & Co., KG; Hamm, Germany). The steady-state shear viscosity of each formulation as a function of shear rate was measured at 25°C using a TA Discovery rheometer (TA Instruments, New Castle, Delaware, USA), which was configured with a 20 mm parallel plate geometry set at a gap of 0.5 mm. The results are reported in Table 3 below.

[0160]

[0161]

[0162]

[0163] Table 3 Steady Shear Viscosity (Formulations of Examples 7 to 26 in Pascal-seconds (Pas))

[0164]

[0165] Examples 9 (control) and 10 show the addition of a compatibilizer based on Example 1 to polypropylene glycol filled with aluminum trihydrate (ATH) particles. The effect in liquid matrix, the compatibilizer based on Example 1 comes from the use of p-toluenesulfonyl isocyanate (PTSI) and polypropylene glycol monobutyl ether With the introduction of the compatibilizer, the viscosity at all shear rates dropped dramatically at all shear rates. The degree of viscosity reduction increased with increasing compatibilizer concentration (Examples 10A to 10D), with the viscosity at the highest concentration decreasing by about an order of magnitude. In addition, the viscosity data for Example 10D showed Newtonian behavior, which reflects the good wetting brought by the compatibilizer of Example 1 and the good dispersion of the filler throughout the liquid matrix.

[0166] Example 11 shows the addition of a compatibilizer based on Example 2 to a granular material filled with ATH particles. The effect in liquid matrix, the compatibilizer based on Example 2 comes from the use of PTSI and higher molecular weight polypropylene glycol monobutyl ether As shown in Table 3, the data for Example 11 shows an order of magnitude reduction in viscosity relative to the PPG / ATH control (Example 9).

[0167] Example 12 (control) and Example 13 show the addition of a compatibilizer based on Example 2 to a granular alumina filled granules. The effect in liquid matrix, the compatibilizer based on Example 2 comes from the use of PTSI and higher molecular weight polypropylene glycol monobutyl ether The viscosity of Example 13 is about 13 to 8 times lower than that of the control.

[0168] Example 14 shows the addition of a compatibilizer based on Example 3 to a polypropylene glycol liquid filled with ATH particles, as compared to its control Example 9. The effect in the matrix, the compatibilizer based on Example 3, comes from the reaction using PTSI and monoamine terminated polypropylene glycol (average Mn = 600). The viscosity of Example 14 is about 140 to 10 times lower than the Example 9 formulation without compatibilizer.

[0169] Example 15 shows the addition of a compatibilizer based on Example 4 to a polypropylene glycol liquid filled with ATH particles, as compared to its control Example 9. The effect in the matrix, the compatibilizer based on Example 4, comes from the reaction using PTSI and polyoxyethylene (4) lauryl ether (average Mn = 362). The viscosity of Example 15 is about 23 to 4 times lower than the Example 9 formulation without compatibilizer.

[0170] Example 16 shows the addition of a compatibilizer based on Example 5 to a polypropylene glycol liquid filled with ATH particles, as compared to its control Example 9. The effect in the matrix, the compatibilizer based on Example 5, comes from the reaction using PTSI and polyoxyethylene (20) sorbitan monooleate (average Mn = 1310). The viscosity of Example 16 is about 18 to 7 times lower than that of the Example 9 formulation without the compatibilizer.

[0171] Example 17 (control) and Example 18 show the effect of adding a compatibilizer based on Example 6, derived from a reaction using PTSI and isostearyl alcohol, to a HMDI liquid matrix filled with ATH particles. With the introduction of the compatibilizer, the viscosity at all shear rates dropped dramatically, i.e., 2-3 orders of magnitude. In addition, the viscosity data for Example 18 showed Newtonian behavior, which reflects the good wetting effect brought by the compatibilizer of Example 6 and the good dispersion of the filler throughout the liquid matrix.

[0172] Example 19 (control) and Example 20 show the effect of adding a compatibilizer based on Example 6, derived from a reaction using PTSI and isostearyl alcohol, to a HDMI liquid matrix filled with alumina particles. With the introduction of the compatibilizer, the viscosity at all shear rates drops dramatically at all shear rates. In addition, the viscosity data show Newtonian behavior, which reflects the good effect brought by the compatibilizer of Example 6 and the good dispersion of the filler in the liquid matrix.

[0173] Examples 21 (control) and 22 show the effect of adding a compatibilizer based on Example 6 derived from a reaction using PTSI and isostearyl alcohol to a 2.5 centistoke polyalphaolefin (PAO-2.5) liquid matrix filled with iron particles. With the introduction of the compatibilizer, the viscosity at all shear rates dropped by about 2 to 22 times at all shear rates.

[0174] Examples 23 (control) and 24 show the effect of adding a compatibilizer based on Example 7 derived from a reaction using PTSI and monocarbinol terminated polydimethylsiloxane (average Mn=10,000) to a 100 centistoke, vinyl terminated polymethylsiloxane liquid matrix filled with ATH. With the introduction of the compatibilizer, the viscosity at all shear rates dropped nominally by a factor of 2 to 5 at all shear rates.

[0175] Example 26 shows the effect of adding a compatibilizer based on Example 3 derived from a reaction using PTSI and monoamine terminated polypropylene glycol (average Mn = 600) to a silyl terminated polyether (viscosity = 7.0 Pa·s) matrix filled with ATH particles, compared to its control Example 25. The viscosity of Example 26 is approximately 1.9 to 1.4 times lower than the viscosity of the Example 25 formulation without compatibilizer.

[0176] Example 27 (control) and Example 28 were prepared by adding the following materials in the weight percentages listed in Table 2 to a 4 ounce glass bottle: deionized water (liquid matrix), PAO-2.5 fluid, and an optional compatibilizer based on Example 8, which was derived from a reaction using PTSI and polyoxyethylene (5) oleyl ether (average Mn=489). The target total mass of Example 27 and Example 28, respectively, with and without the compatibilizer was 60 grams. The formulations were then mixed at 1800 rpm for 10 minutes at room temperature using a Caframo mixer (Caframo, Wiarton, Ontario, Canada) equipped with a 25.4 mm diameter Cowles disperser blade. The stability of the mixture was monitored immediately after stopping the mixer. Example 27 showed that the PAO-2.5 fluid immediately phase separated from the water, with the PAO forming a distinct clear layer on top of the clear aqueous phase below. In contrast, Example 28 showed a uniform opaque white appearance throughout the mixture, demonstrating the ability of the Example 8 compatibilizer to produce an oil-in-water emulsion. After approximately one hour, the mixture showed some signs of phase separation; however, the top and bottom phases remained opaque white.

[0177] Example 29 (control) and Example 30 were prepared according to Table 2 to compare the effect of adding 2 wt% by mass of Example 6 compatibilizer, which is based on the reaction between PTSI and isostearyl alcohol, on the coefficient of friction of stainless steel. Specifically, 29.4 g of PAO-2.5 liquid base and 0.6 g of Example 6 compatibilizer were added to a 2 oz glass bottle to prepare Example 30. The bottle was capped and placed on a roller for 16 hours overnight to ensure complete mixing. The coefficient of friction (COF) was measured for pure PAO fluid (Example 29) and fluid containing Example 6 compatibilizer (Example 30) using a Discovery ARES rheometer (TA Instruments, New Castle, DE, USA) equipped with a stainless steel ring-on-plate configuration. The blend of Example 30 showed a COF value of 0.16, which is about 29% lower than the 0.23 value of the PAO fluid alone.

[0178] It should be understood that various details of the subject matter of the present disclosure may be changed without departing from the scope of the subject matter of the present disclosure.In addition, the foregoing description is for the purpose of illustration only, and not for the purpose of limitation.

Claims

1. A composition comprising: (a) liquid matrix; (b) a compatibilizer, the compatibilizer comprising: (b1) one or more first groups, wherein each of the one or more first groups comprises an arylsulfonyl moiety; as well as (b2) one or more second groups, wherein each of the one or more second groups comprises a hydrocarbyl moiety, a polymer moiety, or an oligomer moiety, or a combination thereof, and wherein each of the one or more second groups is attached to at least one of the one or more first groups; and (c) one or more optional additional ingredients.

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

3. The composition according to claim 1 or 2, wherein the compatibilizer (b) has a structure of one of formulas (I) to (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); (A1-X1) p -Z3 (V), in 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 an arylene group or a substituted arylene group; 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 selected from hydrocarbon groups and -(L2) s -(L3) t -R1, wherein s is 0 or 1; t is 0 or 1; L2 is an alkylene group, L3 is a polymeric or oligomeric moiety, and R1 is a hydrocarbon group or a silyl group; Z2 is an alkylene group, a polymer moiety or an oligomer moiety, or a combination thereof; and Z3 is a polyvalent group derived from a compound including at least three hydroxyl, 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. 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; optionally, wherein the liquid matrix comprises 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. The composition according to any one of claims 1 to 5, wherein the optional additional ingredient (c) comprises solid organic and / or inorganic particles and / or fibers, optionally wherein ingredient (c) comprises one or more particles and / or fibers selected from the group consisting of silica, fumed silica, fused silica, talc, mica, wollastonite, calcium carbonate, carbon, polymers, aluminum, aluminum trihydrate (ATH), iron, silver, metal oxides, boron nitride and aluminum nitride.

7. A composition according to any one of claims 1 to 5, wherein the optional additional ingredient (c) comprises an additional liquid ingredient, wherein the additional liquid ingredient is a liquid that is incompatible with the liquid matrix (a).

8. The composition according to any one of claims 1 to 7, wherein the compatibilizer has the structure of formula (I): A1-X1-Z1 (I); in 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 selected from hydrocarbon groups and -(L2) s -(L3) t -R1, wherein s is 0 or 1; t is 0 or 1; L2 is an alkylene group, L3 is a polymeric moiety or an oligomeric moiety, and R1 is a hydrocarbon group or a silyl group.

9. The composition according to claim 8, wherein A1 is phenyl or methyl-substituted phenyl.

10. A composition according to claim 8 or claim 9, wherein Z1 is a hydrocarbon group, optionally isostearyl.

11. The composition according to claim 8 or claim 9, wherein Z1 is -(L2) s -(L3) t -R1, wherein s is 0, t is 1, L3 is a polyether polyol moiety, and R1 is a C1-C6 hydrocarbon group.

12. The composition according to claim 8 or claim 9, wherein Z1 is -(L2) s -(L3) t-R1, wherein s is 1, t is 1, L2 is an alkylene group, L3 is a polysiloxane moiety, and R1 is a silyl group.

13. The composition of claim 8 or claim 9, wherein the compatibilizer has the structure of formula (Ia): Wherein Z1 is selected from hydrocarbon groups and -(L2) s -(L3) t -R1, wherein s is 0 or 1; t is 0 or 1; L2 is an alkylene group, L3 is a polymeric moiety or an oligomeric moiety, and R1 is a hydrocarbon group or a silyl group.

14. The composition of claim 8 or claim 9, wherein A1 is a methyl-substituted phenyl group, X1 is -S(=O)2-NH-C(=O)-O-, and Z1 is -(L2) s -(L3) t -R1, wherein s is 0, t is 1, L3 is a polyether polyol moiety, and R1 is methyl; and wherein the liquid matrix (a) comprises a polyether polyol, and the optional additional component (c) comprises one or more organic and / or inorganic particles, optionally comprising ATH particles.

15. The composition of claim 8 or claim 9, wherein A1 is a methyl-substituted phenyl group, X1 is -S(=O)2-NH-C(=O)-NH-, and Z1 is -(L2) s -(L3) t -R1, wherein s is 0, t is 1, L3 is a polyether polyol, and R1 is a methyl group; and wherein the liquid matrix (a) comprises a polyether polyol, and the optional additional component (c) comprises one or more organic and / or inorganic particles, optionally comprising ATH particles.

16. A composition according to claim 8 or claim 9, wherein A1 is methyl-substituted phenyl, X1 is -S(=O)2-NH-C(=O)-O-, and Z1 is isostearyl; and wherein the liquid matrix (a) comprises PAO, and the optional additional ingredients (c) comprise one or more organic and / or inorganic particles, optionally comprising iron particles.

17. A composition according to claim 8 or claim 9, wherein A1 is a methyl-substituted phenyl group, X1 is -S(=O)2-NH-C(=O)-O-, and Z1 is -(L2) s -(L3) t-R1, wherein s is 1, t is 1, L2 is -CH2CH2-OCH2CH2CH2-, L3 is a polydimethylsiloxane (PDMS) moiety, and R1 is a silyl group; and wherein the liquid matrix (a) comprises a silicone resin, and the optional additional component (c) comprises one or more organic and / or inorganic particles, optionally including ATH particles.

18. A composition according to claim 8 or claim 9, wherein A1 is a methyl-substituted phenyl group, X1 is -S(=O)2-NH-C(=O)-O-, and Z1 is isostearyl; and wherein the liquid matrix (a) comprises an isocyanate, optionally comprising HDMI; and the optional additional ingredient (c) comprises one or more organic and / or inorganic particles, optionally comprising ATH particles.

19. A composition according to claim 8 or claim 9, wherein A1 is a methyl-substituted phenyl group, X1 is -S(=O)2-NH-C(=O)-O-, and Z1 is polyoxyethylene (5) oleyl ether; and wherein the liquid matrix (a) comprises water; and the optional additional ingredient (c) comprises PAO.

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

21. A method of changing the viscosity of a polymer resin composition, the method comprising contacting a composition comprising a polymer resin with a compatibilizer, wherein the compatibilizer comprises: (b1) one or more first groups, wherein each of the one or more first groups comprises an arylsulfonyl moiety; and (b2) one or more second groups, wherein each of the one or more second groups comprises a hydrocarbon group, a polymer group or an oligomer group, or a combination thereof, and wherein each of the one or more second groups is connected to at least one of the one or more first groups.

22. The method of claim 21, wherein the compatibilizer has the structure of formula (I): A1-X1-Z1 (I); in A1 is an aryl or substituted aryl group; X1 is selected from the group consisting of -S(=O)2-NH-C(=O)-Q- or -S(=O)2-NH-C(=O)-; Q is O or NH; and Z1 is selected from hydrocarbon groups and -(L2) s -(L3) t -R1, wherein s is 0 or 1; t is 0 or 1; L2 is an alkylene group, L3 is a polymeric moiety or an oligomeric moiety, and R1 is a hydrocarbon group or a silyl group.

23. A method according to claim 21 or claim 22, wherein the polymer resin comprises solid organic and / or inorganic filler particles and / or fibres.

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

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

26. A method for preparing a polyurethane, wherein the method comprises contacting a composition comprising a polyol and / or an isocyanate resin with a compatibilizer, wherein the compatibilizer comprises: (b1) one or more first groups, wherein each of the one or more first groups comprises an arylsulfonyl moiety; as well as (b2) one or more second groups, wherein each of the one or more second groups comprises a hydrocarbyl portion, a polymer portion or an oligomer portion, or a combination thereof, and wherein each of the one or more second groups is attached to at least one of the one or more first groups.

27. The method of claim 26, wherein the compatibilizer has the structure of formula (I): A1-X1-Z1 (I); in A1 is an aryl or substituted aryl group; X1 is selected from the group consisting of -S(=O)2-NH-C(=O)-Q- or -S(=O)2-NH-C(=O)-; Q is O or NH; and Z1 is selected from hydrocarbon groups and -(L2) s -(L3) t -R1, wherein s is 0 or 1; t is 0 or 1; L2 is an alkylene group, L3 is a polymeric or oligomeric moiety, optionally a polyether or polysiloxane group, and R1 is a hydrocarbon group or a silyl group.

28. A method according to claim 26 or claim 27, wherein the method further comprises contacting the composition with one or more organic and / or inorganic filler particles and / or fibres.

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

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

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

32. A compound having a structure of one of formulas (I) to (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); (A1-X1) p -Z3 (V), in 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 an arylene group or a substituted arylene group; 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 selected from hydrocarbon groups and -(L2) s -(L3) t -R1, wherein s is 0 or 1; t is 0 or 1; L2 is an alkylene group, L3 is a polymeric or oligomeric moiety, and R1 is a hydrocarbon group or a silyl group; Z2 is an alkylene group, a polymer moiety or an oligomer moiety, or a combination thereof; as well as Z3 is a polyvalent group derived from a compound including at least three hydroxyl, amino or carboxylic acid groups.

33. The compound according to claim 32, wherein the compound has the structure of formula (I): A1-X1-Z1 (I); in 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 selected from hydrocarbon groups and -(L2) s -(L3) t -R1, wherein s is 0 or 1; t is 0 or 1; L2 is an alkylene group, L3 is a polymeric moiety or an oligomeric moiety, and R1 is a hydrocarbon group or a silyl group.

34. The compound according to claim 33, wherein A1 is phenyl or methyl-substituted phenyl.

35. The compound according to claim 33, wherein X1 is -S(=O)2-NH-C(=O)-O-.

36. The compound according to claim 33, wherein Z1 is a hydrocarbon group, optionally a C8-C40 hydrocarbon group.

37. The compound according to claim 33, wherein Z1 is -(L2) s -(L3) t -R1, wherein s is 0 or 1; t is 1; L2 is an alkylene group, L3 is a polymer group or an oligomer group, optionally a polyether or polysiloxane group, and R1 is a hydrocarbon group or a silyl group.

38. The compound of claim 33, wherein Z1 is selected from isostearyl, a hydrocarbyl-terminated polyether polyol, and an alkylene-polysiloxane moiety.

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

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