Synthesis of aminoalkyl-substituted disiloxanes

Abstract

A method for preparing an aminoalkyl-substituted disiloxane is described herein. The method includes forming a mixture containing a di- or polyamine containing at least one primary amine group and a silane; reacting the mixture in a first reaction; adding a hydrolysis agent to the mixture; and reacting the mixture in a second reaction to form an aminoalkyl-substituted disiloxane. The aminoalkyl-substituted disiloxane prepared according to this method is also described herein.

Description

[Technical Field]

[0001] The field of this disclosure relates generally to methods of preparing aminoalkyl-substituted disiloxanes and the aminoalkyl-substituted disiloxanes produced thereby. [Background technology]

[0002] Aminoalkyl-substituted disiloxanes are useful for a wide variety of purposes, for example, they are particularly useful in carbon dioxide capture systems or aminosilicone-based products.

[0003] Substituted disiloxanes are often produced by known reactions. However, known reactions may be limited in scope and may not be effective for producing aminoalkyl-substituted disiloxanes. For example, the process described in Chinese Patent No. 102675596 involves a reaction route that is not suitable for aminoalkyl-substituted disiloxanes due to a side reaction that preferentially forms cyclic products. Similarly, the process described in Chinese Patent No. 102351893 starts from a material that can only be hydrolyzed to one compound. Furthermore, some processes, such as the process described in Li, et al., Thermochimica Acta, 2012, 545, 75, may require a relatively large number of reaction steps and / or require multi-step reaction routes and intermediate purification steps, which can reduce the overall yield and increase the cost and complexity of the process.

[0004] Therefore, opportunities for preparing aminoalkyl-substituted disiloxanes are limited. Therefore, there is a need for a simplified method for preparing aminoalkyl-substituted disiloxanes. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Chinese Patent No. 102351893 Summary of the Invention

[0006] In one embodiment, a method for preparing an aminoalkyl-substituted disiloxane is provided, the method comprising: I) forming a mixture comprising a di- or polyamine containing at least one primary amine group and a silane; II) reacting the mixture in a first reaction; III) adding a hydrolysis agent to the mixture; and IV) reacting the mixture in a second reaction to form the aminoalkyl-substituted disiloxane.

[0007] In another embodiment, there is provided an aminoalkyl-substituted disiloxane of formula (I), which is as follows: [ka] [In the formula, R 12 , R 13 , R 14 , R 15 are each independently selected from the group consisting of hydrogen, substituted or unsubstituted linear alkyl, substituted or unsubstituted C1-C6 linear alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C3-C6 branched alkyl, substituted or unsubstituted linear heteroalkyl, substituted or unsubstituted branched heteroalkyl, aryl, phenyl, heteroaryl, methyl, ethyl, propyl, isopropyl, butyl, pentyl, and hexyl; R 16 and R 17 are each independently selected from the group consisting of a direct bond, substituted or unsubstituted C1-C6 straight chain alkyl, substituted or unsubstituted C3-C6 branched alkyl, C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, and C6 alkyl; and R 18 and R 19 are each independently selected from the group consisting of substituents of formula (IV), [ka] (In the formula, The wavy bond indicates the attachment point relative to formula (I); R 25 , R 26 , R 27 , R 28 , R 29 and R 30 are each independently selected from the group consisting of hydrogen, substituted or unsubstituted straight chain alkyl, substituted or unsubstituted C1-C6 straight chain alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C3-C6 branched alkyl, substituted or unsubstituted straight chain heteroalkyl, substituted or unsubstituted C1-C6 straight chain heteroalkyl, substituted or unsubstituted branched heteroalkyl, substituted or unsubstituted C3-C6 branched heteroalkyl, aryl, heteroaryl, methyl, ethyl, propyl, isopropyl, butyl, pentyl, and hexyl; R 31 and R 32 are each individually selected from the group consisting of hydrogen, substituted or unsubstituted straight chain alkyl, substituted or unsubstituted C1-C6 straight chain alkyl, substituted or unsubstituted C1-C3 straight chain alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C3-C6 branched alkyl, methyl, ethyl, propyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted C3-C6 cycloalkyl, and substituted or unsubstituted C4-C6 cycloalkyl, or together represent R 31 and R 32 forms a monocyclic ring selected from the group consisting of heterocycloalkyl or heteroaryl; R 33 , R 34 and R 35 are each independently selected from the group consisting of a direct bond, substituted or unsubstituted C1-C6 straight chain alkyl, substituted or unsubstituted C3-C6 branched alkyl, C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, ether, -OCH2CH2-, -OCH2CH2CH2-, -OCH2CH2CH2CH2-, -NHCH2CH2-, -NHCH2CH2CH2- and -NHCH2CH2CH2CH2-; R 36is selected from the group consisting of hydrogen, substituted or unsubstituted straight chain alkyl, substituted or unsubstituted C1-C6 straight chain alkyl, substituted or unsubstituted C1-C3 straight chain alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C3-C6 branched alkyl, methyl, ethyl, propyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted C3-C6 cycloalkyl, substituted or unsubstituted C4-C6 cycloalkyl, heterocycloalkyl, and heteroaryl; and m is an integer ranging from 0 to 20); However, the aminoalkyl-substituted disiloxane [ka] isn't it].

[0008] These and other features, aspects and advantages of the present disclosure will be better understood from the following detailed description when taken in conjunction with the accompanying drawings, in which like reference numerals represent like parts throughout. [Brief explanation of the drawings]

[0009] [Figure 1] FIG. 1 is an exemplary method flowchart according to the present disclosure. DETAILED DESCRIPTION OF THE INVENTION

[0010] Unless otherwise indicated, the drawings provided herein are intended to illustrate features of embodiments of the present disclosure. These features are believed to be applicable in a wide variety of systems incorporating one or more embodiments of the present disclosure. Thus, the drawings are not intended to include all conventional features known to those skilled in the art that are required for the practice of the embodiments disclosed herein.

[0011] The embodiments described herein overcome at least some of the drawbacks of known methods for preparing aminoalkyl-substituted disiloxanes and known aminoalkyl-substituted disiloxanes. Exemplary embodiments described herein include a method for preparing an aminoalkyl-substituted disiloxane, comprising: I) forming a mixture containing a di- or polyamine containing at least one primary amine group and a silane; II) reacting the mixture in a first reaction; III) adding a hydrolysis agent to the mixture; and IV) reacting the mixture in a second reaction to form an aminoalkyl-substituted disiloxane. The exemplary embodiments described herein avoid side reactions and / or produce the desired product in superior yield and purity with fewer steps compared to known methods for preparing aminoalkyl-substituted disiloxanes.

[0012] In many embodiments, this method is one-pot synthesis.As used herein, one-pot synthesis is synthesis that is carried out in a single reaction vessel.There is no need to remove intermediates from the reaction vessel for separation and / or purification.One-pot synthesis can include one reaction or two or more reactions.One-pot synthesis is particularly advantageous for reducing the complexity of reaction and avoiding lengthy and expensive separation and purification.

[0013] In many embodiments, the aminoalkyl-substituted disiloxane is an amino-C1-C6 alkyl-substituted disiloxane. Embodiments containing a C1-C6 alkyl group are thermodynamically favored to form compared to other compounds containing larger aminoalkyl substituents or alternative substituents. In some embodiments, the aminoalkyl-substituted disiloxane is an aminomethyl-substituted disiloxane.

[0014] 1 is an exemplary method flowchart 110. In this exemplary embodiment, method flowchart 110 illustrates the essential method steps of exemplary embodiments described herein and is not intended to limit the method embodiments. Initially, a mixture is formed 112 including a di- or polyamine containing at least one primary amine group and a silane. The mixture is reacted 114 in a first reaction, and a hydrolysis agent is added to the mixture 116. The mixture is then reacted 118 in a second reaction to form an aminoalkyl-substituted disiloxane.

[0015] In some embodiments, the aminoalkyl-substituted disiloxane according to the present disclosure is selected from the group consisting of aminoalkyl-substituted disiloxanes of formula (I): [ka] [In the formula, R 12 , R 13 , R 14 , R 15 are each independently selected from the group consisting of hydrogen, substituted or unsubstituted linear alkyl, substituted or unsubstituted C1-C6 linear alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C3-C6 branched alkyl, substituted or unsubstituted linear heteroalkyl, substituted or unsubstituted branched heteroalkyl, aryl, phenyl, heteroaryl, methyl, ethyl, propyl, isopropyl, butyl, pentyl, and hexyl; R 16 and R 17 are each independently selected from the group consisting of a direct bond, substituted or unsubstituted C1-C6 straight chain alkyl, substituted or unsubstituted C3-C6 branched alkyl, C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, and C6 alkyl, preferably C1-C6 straight chain alkyl, even more preferably C1 alkyl; and R 18 and R 19 are each independently selected from the group consisting of substituents of formula (IV), [ka] (In the formula, The wavy bond indicates the attachment point relative to formula (I); R 25 , R 26 , R 27 , R 28 , R 29 and R 30 are each independently selected from the group consisting of hydrogen, substituted or unsubstituted straight chain alkyl, substituted or unsubstituted C1-C6 straight chain alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C3-C6 branched alkyl, substituted or unsubstituted straight chain heteroalkyl, substituted or unsubstituted C1-C6 straight chain heteroalkyl, substituted or unsubstituted branched heteroalkyl, substituted or unsubstituted C3-C6 branched heteroalkyl, aryl, heteroaryl, methyl, ethyl, propyl, isopropyl, butyl, pentyl, and hexyl; R 31 and R 32 are each individually selected from the group consisting of hydrogen, substituted or unsubstituted straight chain alkyl, substituted or unsubstituted C1-C6 straight chain alkyl, substituted or unsubstituted C1-C3 straight chain alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C3-C6 branched alkyl, methyl, ethyl, propyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted C3-C6 cycloalkyl, and substituted or unsubstituted C4-C6 cycloalkyl, or together represent R 31 and R 32 forms a monocyclic ring selected from the group consisting of heterocycloalkyl or heteroaryl; R 33 , R 34 and R 35 are each independently selected from the group consisting of a direct bond, substituted or unsubstituted C1-C6 straight chain alkyl, substituted or unsubstituted C3-C6 branched alkyl, C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, ether, -OCH2CH2-, -OCH2CH2CH2-, -OCH2CH2CH2CH2-, -NHCH2CH2-, -NHCH2CH2CH2- and -NHCH2CH2CH2CH2-; R36 is selected from the group consisting of hydrogen, substituted or unsubstituted straight chain alkyl, substituted or unsubstituted C1-C6 straight chain alkyl, substituted or unsubstituted C1-C3 straight chain alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C3-C6 branched alkyl, methyl, ethyl, propyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted C3-C6 cycloalkyl, substituted or unsubstituted C4-C6 cycloalkyl, heterocycloalkyl, and heteroaryl; and m is an integer ranging from 0 to 20, preferably ranging from 0 to 10, and even more preferably ranging from 0 to 3; However, the aminoalkyl-substituted disiloxane [ka] isn't it].

[0016] In some embodiments, the aminoalkyl-substituted disiloxane is selected from the group consisting of: [ka] JPEG2025540645000009.jpg150155

[0017] In some embodiments, the di- or polyamine containing at least one primary amine group can be any suitable di- or polyamine containing at least one primary amine group known in the art that facilitates the methods described herein. In other embodiments, the di- or polyamine containing at least one primary amine group is a compound of formula (II): [ka] (In the formula, R1, R2, R3, R4, R5 and R6 are each independently selected from the group consisting of hydrogen, substituted or unsubstituted linear alkyl, substituted or unsubstituted C1-C6 linear alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C3-C6 branched alkyl, substituted or unsubstituted linear heteroalkyl, substituted or unsubstituted branched heteroalkyl, substituted or unsubstituted C3-C6 branched heteroalkyl, aryl, phenyl, heteroaryl, methyl, ethyl, propyl, isopropyl, butyl, pentyl and hexyl; R7 and R8 are each individually selected from the group consisting of hydrogen, substituted or unsubstituted linear alkyl, substituted or unsubstituted C1-C6 linear alkyl, substituted or unsubstituted C1-C3 linear alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C3-C6 branched alkyl, methyl, ethyl, propyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted C3-C6 cycloalkyl, and substituted or unsubstituted C4-C6 cycloalkyl, or together R7 and R8 form a monocycle selected from the group consisting of heterocycloalkyl or heteroaryl; R9, R 10 and R 11 are each independently selected from the group consisting of a direct bond, substituted or unsubstituted C1-C6 straight chain alkyl, substituted or unsubstituted C3-C6 branched alkyl, C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, ether, -OCH2CH2-, -OCH2CH2CH2-, -OCH2CH2CH2CH2-, -NHCH2CH2-, -NHCH2CH2CH2- and -NHCH2CH2CH2CH2-; and n is an integer ranging from 0 to 20, preferably ranging from 0 to 10, and even more preferably ranging from 0 to 3).

[0018] In some embodiments, the silane can be any suitable silane known in the art that facilitates the methods described herein. In some embodiments, the silane is an alkoxysilane. In at least some embodiments, the silane is a compound of formula (III): [ka] (In the formula, R 20 is selected from the group consisting of halides, fluorides, chlorides, bromides, and iodides; R 21 and R 22 are each independently selected from the group consisting of hydrogen, substituted or unsubstituted linear alkyl, substituted or unsubstituted C1-C6 linear alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C3-C6 branched alkyl, substituted or unsubstituted linear heteroalkyl, substituted or unsubstituted branched heteroalkyl, aryl, phenyl, heteroaryl, methyl, ethyl, propyl, isopropyl, butyl, pentyl, and hexyl; R 23 and R 24 are each independently selected from the group consisting of substituted or unsubstituted C1-C6 straight chain alkyl, substituted or unsubstituted C3-C6 branched alkyl, C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, aryl, and phenyl).

[0019] In some embodiments, R 23 and R 24 are each independently selected from the group consisting of substituted or unsubstituted C1-C6 straight chain alkyl, substituted or unsubstituted C3-C6 branched alkyl, C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl and C6 alkyl, preferably C1-C6 straight chain alkyl.

[0020] In some embodiments, R 23 is a C1 alkyl.

[0021] In some embodiments, R 24 is C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, aryl or phenyl.

[0022] In some embodiments, the silane is [ka] In some embodiments, the silane is [ka] is.

[0023] In many embodiments, reacting the mixture in a first reaction 114 can be carried out under any suitable reaction conditions known in the art that facilitate the methods described herein, hi some embodiments, reacting the mixture in a first reaction 114 includes stirring the mixture.

[0024] In many embodiments, reacting the mixture in the first reaction 114 can be carried out for any suitable amount of time known in the art that facilitates the methods described herein. In some embodiments, the mixture is reacted in the first reaction 114 for an elapsed time in the range of about 1 second to about 12 hours. In some embodiments, the mixture is reacted in the first reaction 114 for an elapsed time in the range of about 1 second to about 6 hours. In some embodiments, the mixture is reacted in the first reaction 114 for an elapsed time in the range of about 1 second to about 3 hours. In some embodiments, the mixture is reacted in the first reaction 114 for an elapsed time in the range of about 1 hour to about 3 hours. In some embodiments, the mixture is reacted in the first reaction 114 for an elapsed time in the range of about 2 hours to about 3 hours.

[0025] In some embodiments, reacting the mixture in a first reaction 114 involves adding a silane (e.g., chloromethyldimethylethoxysilane) dropwise over about 1 hour to a neat di- or polyamine containing at least one primary amine group. The reaction temperature is allowed to rise to about 90°C due to the reaction exotherm and is held at this temperature for the duration of the reaction (about 2-3 hours total). During this time, the HCl salt of the amine forms and may precipitate to varying degrees depending on the amine.

[0026] In some embodiments, the hydrolyzing agent is added dropwise to the mixture 116. In some embodiments, the hydrolyzing agent is added to the mixture over a period of time. In some embodiments, the hydrolyzing agent is added to the mixture over a period of time ranging from about 1 second to about 12 hours 116. In some embodiments, the hydrolyzing agent is added over 30 minutes and exothermic conditions 116, and the mixture is cooled to room temperature before reacting 118 in a second reaction.

[0027] In some embodiments, the hydrolyzing agent is added 116 over 30 minutes and exothermic conditions, after which the mixture is reacted in a second reaction 118. In these embodiments, the reacting 118 is completed before allowing the reaction mixture to cool to room temperature.

[0028] In many embodiments, the hydrolysis agent can be any suitable hydrolysis agent known in the art that facilitates the methods described herein. In some embodiments, the hydrolysis agent is an aqueous solution. In some embodiments, the hydrolysis agent is water.

[0029] In many embodiments, reacting 118 the mixture in a second reaction can be carried out under any suitable reaction conditions known in the art that facilitate the methods described herein. In some embodiments, reacting 118 the mixture in a second reaction includes adjusting the temperature of the mixture. In some embodiments, reacting 118 the mixture in a second reaction includes cooling the mixture.

[0030] In some embodiments, the aminoalkyl-substituted disiloxane is further extracted from the reaction mixture. In some embodiments, the aminoalkyl-substituted disiloxane is further extracted from the reaction mixture using an organic solvent.

[0031] In some embodiments, extracting the aminoalkyl-substituted disiloxane from the reaction mixture comprises adding an organic solvent (e.g., chloroform and / or toluene) dropwise to the reaction mixture over 30 minutes and vigorously stirring the reaction mixture for about 1 hour or until cooled to room temperature. Once cooled, the organic layer is isolated, the aqueous layer is back-extracted with a minimum of organic solvent, and the combined organic layers are concentrated under vacuum, triturated once with organic solvent, and then dried under vacuum.

[0032] In some embodiments, the aminoalkyl-substituted disiloxane is further purified. In some embodiments, the further purification includes the use of distillation, vacuum distillation, and / or heat. In some embodiments, the further purification includes the use of vacuum distillation to remove impurities and by-products. In these embodiments, the remaining material in the distillation pot is a higher purity product compared to the product prior to purification.

[0033] In many embodiments, reacting the mixture in the second reaction 118 can be carried out for any suitable amount of time known in the art that facilitates the methods described herein. In some embodiments, the mixture is reacted in the second reaction 118 for an elapsed time in the range of about 1 second to about 12 hours. In some embodiments, the mixture is reacted in the second reaction 118 for an elapsed time in the range of about 1 second to about 6 hours. In some embodiments, the mixture is reacted in the second reaction 118 for an elapsed time in the range of about 1 second to about 3 hours. In some embodiments, the mixture is reacted in the second reaction 118 for an elapsed time in the range of about 1 hour to about 3 hours. In some embodiments, the mixture is reacted in the second reaction 118 for an elapsed time in the range of about 2 hours to about 3 hours.

[0034] In many embodiments, the methods may also include any additional suitable processing steps known in the art that facilitate the success of the methods described herein. Such processing steps include, but are not limited to, washing, drying, filtering, purifying, separating, centrifuging, and any combination thereof. In some embodiments, the methods further include washing the aminoalkyl-substituted disiloxane compound. In some embodiments, the methods further include purifying the aminoalkyl-substituted disiloxane compound. In some embodiments, the purifying includes distillation, vacuum distillation, and / or the use of heat. In some embodiments, the methods further include removing volatile reaction by-products.

[0035] In some embodiments, the method includes: I) forming a mixture comprising a di- or polyamine containing at least one primary amine group and a chloromethyldimethylalkoxysilane; II) reacting the mixture in a first reaction with a controlled, essentially exothermic reaction; III) adding a hydrolysis agent to the mixture; IV) reacting the mixture in a second reaction to form an aminoalkyl-substituted disiloxane; V) extracting the aminoalkyl-substituted disiloxane; and (VI) purifying the aminoalkyl-substituted disiloxane.

[0036] In many embodiments, the aminoalkyl-substituted disiloxanes can be used according to any suitable purpose known in the art. In some embodiments, the aminoalkyl-substituted disiloxanes are used in carbon dioxide capture systems. In some embodiments, the aminoalkyl-substituted disiloxanes are used in aminosilicone-based products.

[0037] Further aspects of the present disclosure are provided by the subject matter of the following clauses.

[0038] 1. A method for preparing an aminoalkyl-substituted disiloxane, the method comprising: I) forming a mixture comprising a di- or polyamine containing at least one primary amine group and a silane; II) reacting the mixture in a first reaction; III) adding a hydrolysis agent to the mixture; and IV) reacting the mixture in a second reaction to form the aminoalkyl-substituted disiloxane.

[0039] 2. The method of clause 1, wherein the aminoalkyl-substituted disiloxane is a compound of formula (I): [ka] [In the formula, R 12 , R 13 , R 14 , R 15 are each independently selected from the group consisting of hydrogen, substituted or unsubstituted linear alkyl, substituted or unsubstituted C1-C6 linear alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C3-C6 branched alkyl, substituted or unsubstituted linear heteroalkyl, substituted or unsubstituted branched heteroalkyl, aryl, phenyl, heteroaryl, methyl, ethyl, propyl, isopropyl, butyl, pentyl, and hexyl; R 16 and R 17 are each independently selected from the group consisting of a direct bond, substituted or unsubstituted C1-C6 straight chain alkyl, substituted or unsubstituted C3-C6 branched alkyl, C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, and C6 alkyl; R 18 and R 19 are each independently selected from the group consisting of substituents of formula (IV) [ka] (In the formula, The wavy bond indicates the attachment point relative to formula (I); R 25 , R 26 , R 27 , R28 , R 29 and R 30 are each independently selected from the group consisting of hydrogen, substituted or unsubstituted straight chain alkyl, substituted or unsubstituted C1-C6 straight chain alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C3-C6 branched alkyl, substituted or unsubstituted straight chain heteroalkyl, substituted or unsubstituted C1-C6 straight chain heteroalkyl, substituted or unsubstituted branched heteroalkyl, substituted or unsubstituted C3-C6 branched heteroalkyl, aryl, heteroaryl, methyl, ethyl, propyl, isopropyl, butyl, pentyl, and hexyl; R 31 and R 32 are each individually selected from the group consisting of hydrogen, substituted or unsubstituted straight chain alkyl, substituted or unsubstituted C1-C6 straight chain alkyl, substituted or unsubstituted C1-C3 straight chain alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C3-C6 branched alkyl, methyl, ethyl, propyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted C3-C6 cycloalkyl, and substituted or unsubstituted C4-C6 cycloalkyl, or together represent R 31 and R 32 forms a monocyclic ring selected from the group consisting of heterocycloalkyl or heteroaryl; R 33 , R 34 and R 35 are each independently selected from the group consisting of a direct bond, substituted or unsubstituted C1-C6 straight chain alkyl, substituted or unsubstituted C3-C6 branched alkyl, C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, ether, -OCH2CH2-, -OCH2CH2CH2-, -OCH2CH2CH2CH2-, -NHCH2CH2-, -NHCH2CH2CH2- and -NHCH2CH2CH2CH2-; R 36is selected from the group consisting of hydrogen, substituted or unsubstituted straight chain alkyl, substituted or unsubstituted C1-C6 straight chain alkyl, substituted or unsubstituted C1-C3 straight chain alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C3-C6 branched alkyl, methyl, ethyl, propyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted C3-C6 cycloalkyl, substituted or unsubstituted C4-C6 cycloalkyl, heterocycloalkyl, and heteroaryl; and m is an integer ranging from 0 to 20).

[0040] 3. The method according to any one of clauses 1 to 2, wherein the aminoalkyl-substituted disiloxane is a compound selected from the group consisting of: [ka] JPEG2025540645000017.jpg150147

[0041] 4. The method according to any one of clauses 1 to 3, wherein the di- or polyamine containing at least one primary amine group is a compound of formula (II): [ka] (In the formula, R1, R2, R3, R4, R5 and R6 are each independently selected from the group consisting of hydrogen, substituted or unsubstituted linear alkyl, substituted or unsubstituted C1-C6 linear alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C3-C6 branched alkyl, substituted or unsubstituted linear heteroalkyl, substituted or unsubstituted branched heteroalkyl, substituted or unsubstituted C3-C6 branched heteroalkyl, aryl, phenyl, heteroaryl, methyl, ethyl, propyl, isopropyl, butyl, pentyl and hexyl; R7 and R8 are each individually selected from the group consisting of hydrogen, substituted or unsubstituted linear alkyl, substituted or unsubstituted C1-C6 linear alkyl, substituted or unsubstituted C1-C3 linear alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C3-C6 branched alkyl, methyl, ethyl, propyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted C3-C6 cycloalkyl, and substituted or unsubstituted C4-C6 cycloalkyl, or together R7 and R8 form a monocycle selected from the group consisting of heterocycloalkyl or heteroaryl; R9, R 10 and R 11 are each independently selected from the group consisting of a direct bond, substituted or unsubstituted C1-C6 straight chain alkyl, substituted or unsubstituted C3-C6 branched alkyl, C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, ether, -OCH2CH2-, -OCH2CH2CH2-, -OCH2CH2CH2CH2-, -NHCH2CH2-, -NHCH2CH2CH2- and -NHCH2CH2CH2CH2-; and where n is an integer ranging from 0 to 20.

[0042] 5. The method of any one of clauses 1 to 4, wherein the silane is a compound of formula (III): [ka] (In the formula, R 20 is selected from the group consisting of halides, fluorides, chlorides, bromides, and iodides; R 21 and R 22are each independently selected from the group consisting of hydrogen, substituted or unsubstituted linear alkyl, substituted or unsubstituted C1-C6 linear alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C3-C6 branched alkyl, substituted or unsubstituted linear heteroalkyl, substituted or unsubstituted branched heteroalkyl, aryl, phenyl, heteroaryl, methyl, ethyl, propyl, isopropyl, butyl, pentyl, and hexyl; R 23 and R 24 are each independently selected from the group consisting of substituted or unsubstituted C1-C6 straight chain alkyl, substituted or unsubstituted C3-C6 branched alkyl, C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, aryl, and phenyl).

[0043] 6. The silane [ka] 6. The method of any one of clauses 1 to 5, wherein

[0044] 7. The method of any one of clauses 1 to 6, wherein reacting the mixture in a first reaction comprises stirring the mixture.

[0045] 8. The method of any one of clauses 1 to 7, wherein reacting the mixture in a first reaction comprises reacting the mixture for a first period of time.

[0046] 9. The method of any one of clauses 1 to 8, wherein the first period of time is a time in the range of about 1 second to about 12 hours.

[0047] 10. The method of any one of clauses 1 to 9, wherein the hydrolyzing agent is an aqueous solution.

[0048] 11. The method of any one of clauses 1 to 10, wherein the hydrolyzing agent is water.

[0049] 12. The method of any one of clauses 1 to 11, wherein the hydrolyzing agent is added over a second period of time.

[0050] 13. The method of any one of clauses 1 to 12, wherein the second period of time is a time in the range of about 1 second to about 12 hours.

[0051] 14. The method of any one of clauses 1 to 13, wherein the hydrolyzing agent is added dropwise to the mixture.

[0052] 15. The method of any one of clauses 1 to 14, further comprising purifying the aminoalkyl-substituted disiloxane.

[0053] 16. The method of any one of clauses 1 to 15, wherein at least one method step comprises adjusting the temperature of the mixture.

[0054] 17. The method of any one of clauses 1 to 16, wherein reacting the mixture in a second reaction includes adjusting the temperature of the mixture.

[0055] 18. The method of any one of clauses 1 to 17, wherein reacting the mixture in a second reaction comprises cooling the mixture.

[0056] 19. The method of any one of clauses 1 to 18, which is a one-pot synthesis.

[0057] 20. An aminoalkyl-substituted disiloxane prepared by the method of any one of clauses 1 to 19.

[0058] 21. Aminoalkyl-substituted disiloxanes of formula (I) [ka] [In the formula, R 12 , R 13 , R 14 , R 15are each independently selected from the group consisting of hydrogen, substituted or unsubstituted linear alkyl, substituted or unsubstituted C1-C6 linear alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C3-C6 branched alkyl, substituted or unsubstituted linear heteroalkyl, substituted or unsubstituted branched heteroalkyl, aryl, phenyl, heteroaryl, methyl, ethyl, propyl, isopropyl, butyl, pentyl, and hexyl; R 16 and R 17 are each independently selected from the group consisting of a direct bond, substituted or unsubstituted C1-C6 straight chain alkyl, substituted or unsubstituted C3-C6 branched alkyl, C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, and C6 alkyl; R 18 and R 19 are each independently selected from the group consisting of substituents of formula (IV), [ka] (In the formula, The wavy bond indicates the attachment point relative to formula (I); R 25 , R 26 , R 27 , R 28 , R 29 and R 30 are each independently selected from the group consisting of hydrogen, substituted or unsubstituted straight chain alkyl, substituted or unsubstituted C1-C6 straight chain alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C3-C6 branched alkyl, substituted or unsubstituted straight chain heteroalkyl, substituted or unsubstituted C1-C6 straight chain heteroalkyl, substituted or unsubstituted branched heteroalkyl, substituted or unsubstituted C3-C6 branched heteroalkyl, aryl, heteroaryl, methyl, ethyl, propyl, isopropyl, butyl, pentyl, and hexyl; R 31 and R 32are each individually selected from the group consisting of hydrogen, substituted or unsubstituted straight chain alkyl, substituted or unsubstituted C1-C6 straight chain alkyl, substituted or unsubstituted C1-C3 straight chain alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C3-C6 branched alkyl, methyl, ethyl, propyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted C3-C6 cycloalkyl, and substituted or unsubstituted C4-C6 cycloalkyl, or together represent R 31 and R 32 forms a monocyclic ring selected from the group consisting of heterocycloalkyl or heteroaryl; R 33 , R 34 and R 35 are each independently selected from the group consisting of a direct bond, substituted or unsubstituted C1-C6 straight chain alkyl, substituted or unsubstituted C3-C6 branched alkyl, C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, ether, -OCH2CH2-, -OCH2CH2CH2-, -OCH2CH2CH2CH2-, -NHCH2CH2-, -NHCH2CH2CH2- and -NHCH2CH2CH2CH2-; R 36 is selected from the group consisting of hydrogen, substituted or unsubstituted straight chain alkyl, substituted or unsubstituted C1-C6 straight chain alkyl, substituted or unsubstituted C1-C3 straight chain alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C3-C6 branched alkyl, methyl, ethyl, propyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted C3-C6 cycloalkyl, substituted or unsubstituted C4-C6 cycloalkyl, heterocycloalkyl, and heteroaryl; and m is an integer ranging from 0 to 20); However, the aminoalkyl-substituted disiloxane [ka] isn't it].

[0059] 22. The aminoalkyl-substituted disiloxane according to any one of clauses 1 to 21, which is a compound selected from the group consisting of: [ka] JPEG2025540645000025.jpg150147

[0060] References to "some embodiments" in the above description are not intended to be interpreted as excluding the existence of additional embodiments that also incorporate the recited features. [Example]

[0061] Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. Therefore, the following examples should be construed as merely illustrative and in no way limiting of the present disclosure. The starting materials in the following examples may not necessarily have been prepared by the specific preparation procedures described in other examples. Furthermore, any numerical range recited herein is understood to include all values ​​from the lower limit to the upper limit. For example, if a range is stated as 10 to 50, it is intended that values ​​such as 12 to 30, 20 to 40, or 30 to 50 are explicitly recited herein. These are merely specifically intended examples, and all possible combinations of values ​​between the recited lowest and highest values, including the recited lowest and highest values, should be considered to be expressly stated in this application.

[0062] Example 1. Synthesis of the aminomethyl-substituted disiloxane, 1,3-bis(2-aminoethylaminomethyl)tetramethyldisiloxane, using 4 equivalents of ethylenediamine. Ethylenediamine (396 mL, 5.93 mol) was added to a 2 L, 3-neck, round-bottom flask equipped with an addition funnel and a reflux condenser. The flask was placed in an ice-water bath and the headspace was purged with N2. Chloromethyldimethylethoxysilane (240 mL, 1.48 mol) was added to the addition funnel and added dropwise to the ethylenediamine over 1 h, during which time the reaction exothermed to 90-100 °C. After an additional 1 h, 1 The reaction was judged complete by H NMR, at which point 300 mL of water was added dropwise to the reaction mixture over 30 minutes, resulting in an exotherm. The reaction mixture was cooled to room temperature with stirring, at which point 300 mL of chloroform was added dropwise. The resulting mixture was vigorously stirred for 1 hour, after which the organic layer was isolated and the aqueous layer was extracted with a minimum volume of chloroform. The combined organic layers were dried under reduced pressure at room temperature. The resulting material was then purified by vacuum distillation. The first fraction, containing primarily cyclic by-products and some product, was collected at 380 mTorr over a range of 40-80 °C. The remaining material (167 g, 81% yield) was 1 It was deemed >75% pure by 1 H NMR spectroscopy. 1 H NMR(CDCl3)δ: 2.80(t,4H,H2NCH2CH2), 2.65(t,4H,H2NCH2), 2.05(s,4H,SiCH2), 1.30(br s,6H,NH&NH2), 0.12(s,12H,SiCH3).

[0063] Example 2. Synthesis of the aminomethyl-substituted disiloxane, 1,3-bis(3-aminopropylaminomethyl)tetramethyldisiloxane The same procedure as in Example 1 was followed, except that 1,3-propanediamine (52 mL, 0.62 mol), chloromethyldimethylethoxysilane (25 mL, 0.15 mol), 40 mL of water, and 40 mL of chloroform were used in a 250 mL three-neck flask. The resulting material was then purified by vacuum distillation. The first fraction, containing mainly cyclic by-products and some product, was collected at 40-65 °C. The remaining material (17.6 g, 74% yield) was purified by vacuum distillation. 1 It was deemed >95% pure by 1 H NMR spectroscopy. 1H NMR(CDCl3)δ: 2.75(t,4H,H2NCH2CH2CH2), 2.65(t,4H,H2NCH2), 2.05(s,4H,SiCH2), 1.60(mult,4H,H2NCH2CH2), 1.30(br s,6H,NH&NH2), 0.12(s,12H,SiCH3).

[0064] Example 3. Synthesis of the aminomethyl-substituted disiloxane, 1,3-bis(2-methyl-3-aminopropylaminomethyl)tetramethyldisiloxane. The same procedure as in Example 1 was followed, except that 2-methyl-1,3-propanediamine (2.84 mL, 0.028 mol), chloromethyldimethylethoxysilane (1.14 mL, 0.0071 mol), 2 mL of water, and 2 mL of chloroform were used in a 15 mL flask. The resulting material was then purified by vacuum distillation. The first fraction, containing by-products and some product, was collected at 110°C. The remaining material (0.60 g, 51% yield) was purified by vacuum distillation. 1 It was deemed >95% pure by 1 H NMR spectroscopy. 1 H NMR(CDCl3)δ:2.8-2.5(overlapping mult,8H,H2NCH2CH(CH3)CH2), 2.05(mult,4H,SiCH2), 1.75(mult,2H,H2NCH2CH), 1.95(br s,6H,NH&NH2), 0.90(d,6H,H2NCH2CHCH3)0.12(s,12H,SiCH3).

[0065] Example 4. Synthesis of the aminomethyl-substituted disiloxane, 1,3 bis(2,2-dimethyl-3-aminopropylaminomethyl)tetramethyldisiloxane. The same procedure as in Example 1 was followed, except that in a 15 mL flask, 2,2-dimethyl-1,3-propanediamine (3.41 mL, 0.028 mol), chloromethyldimethylethoxysilane (1.12 mL, 0.0071 mol), 2 mL of water, and 2 mL of chloroform were used. The resulting material was then purified by vacuum distillation. The first fraction, containing by-products and some product, was collected at 80-90 °C. The remaining material (0.95 g, 74% yield) was purified by vacuum distillation.1 It was deemed >95% pure by 1 H NMR spectroscopy. 1 H NMR(CDCl3)δ:3.10(br s,6H,NH&NH2), 2.67(s,4H,H2NCH2), 2.60(s,4H,H2NCH2C(CH3)2CH2), 2.15(s,4H,SiCH2), 0.95(s,12H,H2NCH2C(CH3)2), 0.19(s,12H,SiCH3).

[0066] Example 5. Synthesis of the aminomethyl-substituted disiloxane, 1,3-bis(2-aminoethylaminomethyl)tetramethyldisiloxane, using 8 equivalents of ethylenediamine. Ethylenediamine (793 mL, 11.9 mol) was added to a 2 L, 3-neck, round-bottom flask equipped with an addition funnel and a reflux condenser. The flask was placed in an ice-water bath and the headspace was purged with N2. Chloromethyldimethylethoxysilane (240 mL, 1.48 mol) was added to the addition funnel and added dropwise to the ethylenediamine over 1 h, during which time the reaction exothermed to 90-100 °C. After an additional 1 h, 1 The reaction was judged complete by H NMR, at which point 300 mL of water was added dropwise to the reaction mixture over 30 minutes, resulting in an exotherm. The reaction mixture was cooled to room temperature with stirring, at which point 300 mL of chloroform was added dropwise. The resulting mixture was vigorously stirred for 1 hour, after which the organic layer was isolated and the aqueous layer was extracted with a minimum volume of chloroform. The combined organic layers were dried under reduced pressure at room temperature. The resulting material was then purified by vacuum distillation. The first fraction, containing primarily cyclic by-products and some product, was collected at 380 mTorr over a range of 40-80 °C. The remaining material (326 g, 79% yield) was 1 It was deemed >90% pure by 1 H NMR spectroscopy. 1 H NMR(CDCl3)δ: 2.80(t,4H,H2NCH2CH2), 2.65(t,4H,H2NCH2), 2.05(s,4H,SiCH2), 1.30(br s,6H,NH&NH2), 0.12(s,12H,SiCH3).

[0067] Example 6. Synthesis of the aminomethyl-substituted disiloxane, 1,3-bis(2-aminoethylaminomethyl)tetramethyldisiloxane, using 10 equivalents of ethylenediamine. Ethylenediamine (400 mL, 5.99 mol) was added to a 2 L, 3-neck, round-bottom flask equipped with an addition funnel and a reflux condenser. The flask was placed in an ice-water bath and the headspace was purged with N2. Chloromethyldimethylethoxysilane (97 mL, 0.59 mol) was added to the addition funnel and added dropwise to the ethylenediamine over 1 h, during which time the reaction exothermed to 90-100 °C. After an additional 1 h, 1 The reaction was judged complete by H NMR, at which point 300 mL of water was added dropwise to the reaction mixture over 30 minutes, resulting in an exotherm. The reaction mixture was cooled to room temperature with stirring, at which point 300 mL of chloroform was added dropwise. The resulting mixture was vigorously stirred for 1 hour, after which the organic layer was isolated and the aqueous layer was extracted with a minimum volume of chloroform. The combined organic layers were dried under reduced pressure at room temperature. The resulting material was then purified by vacuum distillation. The first fraction, containing primarily cyclic by-products and some product, was collected at 380 mTorr over a range of 40-80 °C. The remaining material (117 g, 70% yield) was 1 It was deemed >95% pure by 1 H NMR spectroscopy. 1 H NMR(CDCl3)δ: 2.80(t,4H,H2NCH2CH2), 2.65(t,4H,H2NCH2), 2.05(s,4H,SiCH2), 1.30(br s,6H,NH&NH2), 0.12(s,12H,SiCH3).

[0068] Comparative Example 1. Attempted synthesis of the aminomethyl-substituted disiloxane, 1,3-bis(2-aminoethylaminomethyl)tetramethyldisiloxane, from 1,3-bis(chloromethyl)tetramethyldisiloxane. Ethylenediamine (13 g, 0.216 mol, 10 eq) was added to a 50 ml three-necked round-bottom flask equipped with a nitrogen blanket, magnetic stir bar, condenser, and addition funnel. This was then heated in an oil bath with an oil setting of 110°C. Once the temperature in the oil bath had stabilized, 1,3-bis(chloromethyl)-1,1,3,3-tetramethyldisiloxane (5 g, 0.0216 mol) was added dropwise over a period of 2 hours. The reaction was stirred at that temperature overnight. The reaction was cooled and 1 H NMR analysis confirmed the reaction was complete. The reaction mixture was then poured into a 250 ml separatory funnel and partitioned between chloroform and 10% NaOH, washed three times with DI water and once with saturated sodium chloride, and then dried over anhydrous potassium chloride. After filtration, the chloroform was stripped on a rotary evaporator to yield a clear, colorless, viscous liquid. 1 H NMR analysis showed a mixture of products containing the cyclic product 2,2,6,6-tetramethyl-1-oxa-4-aza-2,6-disilacyclohexane-4-ethanamine. The desired 1,3-bis(2-aminoethylaminomethyl)tetramethyldisiloxane was not formed.

[0069] Comparative Example 2. Attempted synthesis of an aminomethyl-substituted disiloxane, 1,3-bis(2-aminoethylaminomethyl)tetramethyldisiloxane, from 1,3-bis(iodomethyl)tetramethyldisiloxane. Ethylenediamine (13 g, 0.216 mol, 10 equiv.) was added to a 50 mL, three-necked, round-bottom flask equipped with a nitrogen blanket, a magnetic stir bar, a condenser, and an addition funnel. 1,3-Bis(iodomethyl)-1,1,3,3-tetramethyldisiloxane (10.16 g, 0.0216 mol) was added dropwise over 2 hours. The reaction was stirred at room temperature overnight. 1 H NMR analysis confirmed the reaction was complete. The reaction mixture was then poured into a 250 ml separatory funnel and partitioned between chloroform and 10% NaOH, washed three times with DI water and once with saturated sodium chloride, and then dried over anhydrous potassium chloride. After filtration, the chloroform was stripped on a rotary evaporator to yield a clear, colorless, viscous liquid.1 H NMR analysis showed the clear formation of the cyclic by-product 2,2,6,6-tetramethyl-1-oxa-4-aza-2,6-disilacyclohexane-4-ethanamine. The desired 1,3-bis(2-aminoethylaminomethyl)tetramethyldisiloxane was not formed. 1 H NMR (CDCl3), δ:2.70(t,2H,CH2), 2.40(t,2H,CH2), 1.75(overlapping s,4H+2H,SiCH2NCH2Si+H2N), 0.10(s,12H,SiCH3).

[0070] Unless otherwise indicated, terms expressing approximation, such as "generally," "substantially," and "about," used herein indicate that the modified term may apply only to an approximate degree, as recognized by one of ordinary skill in the art, rather than to an absolute or complete degree. Thus, values ​​modified by one or more terms, such as "about," "approximately," and "substantially," are not limited to the exact value specified. In at least some instances, terms expressing approximation may correspond to the precision of an instrument for measuring a value. Furthermore, unless otherwise indicated, terms such as "first," "second," and the like are used herein merely as labels and do not impose any order, position, or hierarchy requirements on the items they refer to. Furthermore, for example, a reference to a "second" item does not require or exclude, for example, the presence of a "first" item or a lower-numbered item, or a "third" or a higher-numbered item.

[0071] Although specific features of various embodiments of the invention may be shown in some drawings and not in others, this is for convenience only. Moreover, references to "some embodiments" in the above description are not intended to be interpreted as excluding the existence of additional embodiments that also incorporate the recited features. In accordance with the principles of the invention, any feature of a drawing may be referenced and / or claimed in combination with any feature of any other drawing.

[0072] This written description uses examples to disclose the invention, including the best mode, and also to enable any person skilled in the art to practice the invention, including making and using any device or system, and performing any incorporated methods. The patentable scope of the invention is defined by the claims, and may include other examples that occur to those skilled in the art. Such other examples are intended to be within the scope of the claims if they have structural elements that do not differ from the literal language of the claims, or if they include equivalent structural elements that do not differ substantially from the literal language of the claims.

[0073] It will be readily understood by those skilled in the art that some substituents in the present disclosure are dependent on the presence of other substituents and are therefore optional. For example, in Formula II, when R is a direct bond, R and R are optional substituents that are not present in the compound. Similarly, in Formula II, when n is 0, R and R 10 There is a direct bond between R3, R4 and R 11 is an optional substituent that is not present in the compound. The selectivity of a substituent in one embodiment is non-restrictive with respect to the presence of a substituent in another embodiment.

[0074] As used herein, the term "alkyl," used alone or in compound words such as "haloalkyl," includes straight-chain or branched alkyls such as methyl, ethyl, n-propyl, and i-propyl, or the different butyl, pentyl, or hexyl isomers. An alkyl defined by a number of carbon atoms, e.g., C alkyl, is understood to have that many carbon atoms, but is not otherwise limited.

[0075] As used herein, the term "heteroalkyl" means an alkyl chain wherein at least one of the atoms forming the backbone of the chain is other than carbon.

[0076] As used herein, "aminoalkyl" includes an N radical substituted with a straight or branched alkyl.

[0077] As used herein, the terms "halogen" or "halide," alone or in compound words such as "haloalkyl," include fluorine, chlorine, bromine, or iodine. Furthermore, when used in compound words such as "haloalkyl," said alkyl can be partially or fully substituted with halogen atoms, which can be the same or different. Examples of "haloalkyl" include F3C, ClCH2, CF3CH2, and CF3CCl2. Terms such as "haloalkoxy" are defined analogously to the term "haloalkyl." Examples of "haloalkoxy" include CF3O, CCl3CHO, F2CHCH2CHO, and CF3CHO.

[0078] As used herein, the term "heterocycle" refers to a ring in which at least one atom forming the ring backbone is other than carbon. Unless otherwise specified, a heterocycle may be a saturated ring, a partially unsaturated ring, or a fully unsaturated ring. If a fully unsaturated heterocycle satisfies Hückel's rule, the ring is also called a "heteroaryl" or an aromatic heterocycle. A "saturated heterocycle" refers to a heterocycle that contains only single bonds between ring members.

Claims

1. 1. A method for preparing an aminoalkyl-substituted disiloxane, comprising: I) a di- or polyamine containing at least one primary amine group; Silane and forming a mixture comprising: II) reacting said mixture in a first reaction; III) adding a hydrolyzing agent to the mixture; and IV) reacting said mixture in a second reaction to form said aminoalkyl-substituted disiloxane.

2. 10. The method of claim 1, wherein the aminoalkyl-substituted disiloxane is a compound of formula (I): 【Chemistry 1】 [In the formula, R １２ , R １３ , R １４ , R １５ are each hydrogen, substituted or unsubstituted linear alkyl, substituted or unsubstituted C １ -C ６ Straight-chain alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C ３ -C ６ individually selected from the group consisting of branched alkyl, substituted or unsubstituted straight chain heteroalkyl, substituted or unsubstituted branched heteroalkyl, aryl, phenyl, heteroaryl, methyl, ethyl, propyl, isopropyl, butyl, pentyl, and hexyl; R １６ and R １７ each represents a direct bond, a substituted or unsubstituted C １ -C ６ Straight chain alkyl, substituted or unsubstituted C ３ -C ６ Branched alkyl, C １ Alkyl, C ２ Alkyl, C ３ Alkyl, C ４ Alkyl, C ５ Alkyl and C ６ individually selected from the group consisting of alkyl; R １８ and R １９ are each independently selected from the group consisting of substituents of formula (IV) 【Chemistry 2】 (In the formula, The wavy bond indicates the point of attachment relative to formula (I); R ２５ , R ２６ , R ２７ , R ２８ , R ２９ and R ３０ are each hydrogen, substituted or unsubstituted linear alkyl, substituted or unsubstituted C １ -C ６ Straight-chain alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C ３ -C ６ Branched alkyl, substituted or unsubstituted straight chain heteroalkyl, substituted or unsubstituted C １ -C ６ Straight-chain heteroalkyl, substituted or unsubstituted branched heteroalkyl, substituted or unsubstituted C ３ -C ６ individually selected from the group consisting of branched heteroalkyl, aryl, heteroaryl, methyl, ethyl, propyl, isopropyl, butyl, pentyl, and hexyl; R ３１ and R ３２ are each hydrogen, substituted or unsubstituted linear alkyl, substituted or unsubstituted C １ -C ６ Straight chain alkyl, substituted or unsubstituted C １ -C ３ Straight-chain alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C ３ -C ６ Branched alkyl, methyl, ethyl, propyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted C ３ -C ６ Cycloalkyl, and substituted or unsubstituted C ４ -C ６ cycloalkyl, R ３１ and R ３２ forms a monocyclic ring selected from the group consisting of heterocycloalkyl or heteroaryl; R ３３ , R ３４ and R ３５ each represents a direct bond, a substituted or unsubstituted C １ -C ６ Straight chain alkyl, substituted or unsubstituted C ３ -C ６ Branched alkyl, C １ Alkyl, C ２ Alkyl, C ３ Alkyl, C ４ Alkyl, C ５ Alkyl, C ６ Alkyl, ether, -OCH ２ CH ２ -, -OCH ２ CH ２ CH ２ -, -OCH ２ CH ２ CH ２ CH ２ --NHCH ２ CH ２ --NHCH ２ CH ２ CH ２ - and -NHCH ２ CH ２ CH ２ CH ２ - individually selected from the group consisting of; R ３６ is hydrogen, substituted or unsubstituted linear alkyl, substituted or unsubstituted C １ -C ６ Straight chain alkyl, substituted or unsubstituted C １ -C ３ Straight-chain alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C ３ -C ６ Branched alkyl, methyl, ethyl, propyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted C ３ -C ６ Cycloalkyl, substituted or unsubstituted C ４ -C ６ selected from the group consisting of cycloalkyl, heterocycloalkyl, and heteroaryl; and and m is an integer ranging from 0 to 20).

3. 2. The method of claim 1, wherein the aminoalkyl-substituted disiloxane is a compound selected from the group consisting of: 【Transformation 3】 【change】

4. 2. The method of claim 1, wherein the di- or polyamine containing at least one primary amine group is a compound of formula (II): 【Chemistry 4】 (In the formula, R １ , R ２ , R ３ , R ４ , R ５ and R ６ are each hydrogen, substituted or unsubstituted linear alkyl, substituted or unsubstituted C １ -C ６ Straight-chain alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C ３ -C ６ Branched alkyl, substituted or unsubstituted straight chain heteroalkyl, substituted or unsubstituted branched heteroalkyl, substituted or unsubstituted C ３ -C ６ individually selected from the group consisting of branched heteroalkyl, aryl, phenyl, heteroaryl, methyl, ethyl, propyl, isopropyl, butyl, pentyl, and hexyl; R ７ and R ８ are each hydrogen, substituted or unsubstituted linear alkyl, substituted or unsubstituted C １ -C ６ Straight chain alkyl, substituted or unsubstituted C １ -C ３ Straight-chain alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C ３ -C ６ Branched alkyl, methyl, ethyl, propyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted C ３ -C ６ Cycloalkyl, and substituted or unsubstituted C ４ -C ６ cycloalkyl, R ７ and R ８ forms a monocyclic ring selected from the group consisting of heterocycloalkyl or heteroaryl; R ９ , R １０ and R １１ each represents a direct bond, a substituted or unsubstituted C １ -C ６ Straight chain alkyl, substituted or unsubstituted C ３ -C ６ Branched alkyl, C １ Alkyl, C ２ Alkyl, C ３ Alkyl, C ４ Alkyl, C ５ Alkyl, C ６ Alkyl, ether, -OCH ２ CH ２ -, -OCH ２ CH ２ CH ２ -, -OCH ２ CH ２ CH ２ CH ２ --NHCH ２ CH ２ --NHCH ２ CH ２ CH ２ - and -NHCH ２ CH ２ CH ２ CH ２ - individually selected from the group consisting of: and n is an integer ranging from 0 to 20.

5. 10. The method of claim 1, wherein the silane is a compound of formula (III): 【Transformation 5】 (In the formula, R ２０ is selected from the group consisting of halides, fluorides, chlorides, bromides, and iodides; R ２１ and R ２２ are each hydrogen, substituted or unsubstituted linear alkyl, substituted or unsubstituted C １ -C ６ Straight-chain alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C ３ -C ６ individually selected from the group consisting of branched alkyl, substituted or unsubstituted straight chain heteroalkyl, substituted or unsubstituted branched heteroalkyl, aryl, phenyl, heteroaryl, methyl, ethyl, propyl, isopropyl, butyl, pentyl, and hexyl; R ２３ and R ２４ are each substituted or unsubstituted C １ -C ６ Straight chain alkyl, substituted or unsubstituted C ３ -C ６ Branched alkyl, C １ Alkyl, C ２ Alkyl, C ３ Alkyl, C ４ Alkyl, C ５ Alkyl, C ６ (Individually selected from the group consisting of alkyl, aryl and phenyl).

6. The silane 【Transformation 6】 The method of claim 1, wherein

7. 10. The method of claim 1, wherein reacting the mixture in a first reaction comprises stirring the mixture.

8. 10. The method of claim 1, wherein reacting the mixture in a first reaction comprises reacting the mixture for a first period of time.

9. The method of claim 8, wherein the first period of time is a time ranging from about 1 second to about 12 hours.

10. The method of claim 1 wherein the hydrolyzing agent is an aqueous solution.

11. The method of claim 1 wherein the hydrolysis agent is water.

12. 10. The method of claim 1, wherein the hydrolysis agent is added to the mixture over a second period of time.

13. The method of claim 12, wherein the second period of time is a time period ranging from about 1 second to about 12 hours.

14. The method of claim 1 , wherein the hydrolysis agent is added dropwise to the mixture.

15. 10. The method of claim 1 further comprising purifying the aminoalkyl-substituted disiloxane.

16. The method of claim 1 , wherein at least one method step comprises adjusting the temperature of the mixture.

17. 10. The method of claim 1, wherein reacting the mixture in a second reaction comprises adjusting a temperature of the mixture.

18. 10. The method of claim 1, wherein reacting the mixture in a second reaction comprises cooling the mixture.

19. The method of claim 1, which is a one-pot synthesis.

20. 10. An aminoalkyl-substituted disiloxane prepared by the method of claim 1.

21. Aminoalkyl-substituted disiloxanes of formula (I) 【Transformation 7】 [In the formula, R １２ , R １３ , R １４ , R １５ are each hydrogen, substituted or unsubstituted linear alkyl, substituted or unsubstituted C １ -C ６ Straight-chain alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C ３ -C ６ individually selected from the group consisting of branched alkyl, substituted or unsubstituted straight chain heteroalkyl, substituted or unsubstituted branched heteroalkyl, aryl, phenyl, heteroaryl, methyl, ethyl, propyl, isopropyl, butyl, pentyl, and hexyl; R １６ and R １７ each represents a direct bond, a substituted or unsubstituted C １ -C ６ Straight chain alkyl, substituted or unsubstituted C ３ -C ６ Branched alkyl, C １ Alkyl, C ２ Alkyl, C ３ Alkyl, C ４ Alkyl, C ５ Alkyl and C ６ individually selected from the group consisting of alkyl; R １８ and R １９ are each independently selected from the group consisting of substituents of formula (IV), 【Transformation 8】 (In the formula, The wavy bond indicates the point of attachment relative to formula (I); R ２５ , R ２６ , R ２７ , R ２８ , R ２９ and R ３０ are each hydrogen, substituted or unsubstituted linear alkyl, substituted or unsubstituted C １ -C ６ Straight-chain alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C ３ -C ６ Branched alkyl, substituted or unsubstituted straight chain heteroalkyl, substituted or unsubstituted C １ -C ６ Straight-chain heteroalkyl, substituted or unsubstituted branched heteroalkyl, substituted or unsubstituted C ３ -C ６ individually selected from the group consisting of branched heteroalkyl, aryl, heteroaryl, methyl, ethyl, propyl, isopropyl, butyl, pentyl, and hexyl; R ３１ and R ３２ are each hydrogen, substituted or unsubstituted linear alkyl, substituted or unsubstituted C １ -C ６ Straight chain alkyl, substituted or unsubstituted C １ -C ３ Straight-chain alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C ３ -C ６ Branched alkyl, methyl, ethyl, propyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted C ３ -C ６ Cycloalkyl, and substituted or unsubstituted C ４ -C ６ cycloalkyl, R ３１ and R ３２ forms a monocyclic ring selected from the group consisting of heterocycloalkyl or heteroaryl; R ３３ , R ３４ and R ３５ each represents a direct bond, a substituted or unsubstituted C １ -C ６ Straight chain alkyl, substituted or unsubstituted C ３ -C ６ Branched alkyl, C １ Alkyl, C ２ Alkyl, C ３ Alkyl, C ４ Alkyl, C ５ Alkyl, C ６ Alkyl, ether, -OCH ２ CH ２ -, -OCH ２ CH ２ CH ２ -, -OCH ２ CH ２ CH ２ CH ２ --NHCH ２ CH ２ --NHCH ２ CH ２ CH ２ - and -NHCH ２ CH ２ CH ２ CH ２ - individually selected from the group consisting of; R ３６ is hydrogen, substituted or unsubstituted linear alkyl, substituted or unsubstituted C １ -C ６ Straight chain alkyl, substituted or unsubstituted C １ -C ３ Straight-chain alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C ３ -C ６ Branched alkyl, methyl, ethyl, propyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted C ３ -C ６ Cycloalkyl, substituted or unsubstituted C ４ -C ６ selected from the group consisting of cycloalkyl, heterocycloalkyl, and heteroaryl; and m is an integer ranging from 0 to 20; However, the aminoalkyl-substituted disiloxane 【Chemistry 9】 isn't it].

22. 22. The aminoalkyl-substituted disiloxane of claim 21, which is a compound selected from the group consisting of: 【Chemistry 10】 【change】

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