Synthesis of aminoalkyl substituted disiloxanes

Abstract

Described herein are methods of making aminoalkyl substituted disiloxanes. The method comprises: forming a mixture comprising a diamine or polyamine comprising at least one primary amine group and comprising a silane; reacting the mixture in a first reaction; adding a hydrolytic agent into the mixture; and reacting the mixture in a second reaction to form an aminoalkyl substituted disiloxane. Also described herein is an aminoalkyl-substituted disiloxane prepared according to the method.

Description

[0001] Related Applications

[0002] This application claims priority to U.S. Provisional Application Serial No. 63 / 386,231, filed on December 6, 2022. Background of the Disclosure

[0003] The field of the present disclosure generally relates to methods for preparing aminoalkyl-substituted disiloxanes and aminoalkyl-substituted disiloxanes produced by such methods.

[0004] Aminoalkyl-substituted disiloxanes can be used for a variety of purposes. For example, they are particularly useful in carbon capture systems or amino-organosilicon-based products.

[0005] Substituted disiloxanes are generally produced by known reactions. However, the known reactions may be limited in scope and may be ineffective for producing aminoalkyl-substituted disiloxanes. For example, the method described in CN102675596 involves a reaction pathway that is not suitable for aminoalkyl-substituted disiloxanes due to side reactions that preferentially form cyclic products. Similarly, the method described in CN102351893 starts from materials that can only be hydrolyzed into one compound. In addition, some methods, such as the method described in Li et al., Thermochimica Acta, 2012, 545, 75, require multi-step reaction pathways and intermediate purification steps, which may require a relatively large number of reaction steps, and / or which may reduce the overall yield and increase the cost and complexity of the method.

[0006] Accordingly, opportunities for preparing aminoalkyl-substituted disiloxanes are limited. Thus, there is a need for a simplified method for preparing aminoalkyl-substituted disiloxanes. Summary of the Invention

[0007] In one aspect, a method for preparing an aminoalkyl-substituted disiloxane is provided. The method includes: I) forming a mixture that includes: a diamine or polyamine containing at least one primary amine group; and a silane; II) reacting the mixture in a first reaction; III) adding a hydrolyzing agent to the mixture; and IV) reacting the mixture in a second reaction to form the aminoalkyl-substituted disiloxane.

[0008] In another aspect, an aminoalkyl-substituted disiloxane of formula (I) is provided. The formula is:

[0009]

[0010] Wherein:

[0011] R 12 、R 13 、R 14 、R15 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-chain alkyl, substituted or unsubstituted C3-C6 branched-chain alkyl, substituted or unsubstituted straight-chain heteroalkyl, substituted or unsubstituted branched-chain heteroalkyl, aryl, phenyl, heteroaryl, methyl, ethyl, propyl, isopropyl, butyl, pentyl and hexyl;

[0012] R 16 and R 17 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-chain alkyl, C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl and C6 alkyl; and

[0013] R 18 and R 19 Each independently selected from the group consisting of substituents of formula (IV)

[0014]

[0015] wherein:

[0016] The wavy bond represents the bonding position to formula (I);

[0017] R 25 、R 26 、R 27 、R 28 、R 29 and R 30 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-chain alkyl, substituted or unsubstituted C3-C6 branched-chain alkyl, substituted or unsubstituted straight-chain heteroalkyl, substituted or unsubstituted C1-C6 straight-chain heteroalkyl, substituted or unsubstituted branched-chain heteroalkyl, substituted or unsubstituted C3-C6 branched-chain heteroalkyl, aryl, heteroaryl, methyl, ethyl, propyl, isopropyl, butyl, pentyl and hexyl;

[0018] R 31 and R 32 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 C1-C3 straight-chain alkyl, substituted or unsubstituted branched-chain alkyl, substituted or unsubstituted C3-C6 branched-chain alkyl, methyl, ethyl, propyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted C3-C6 cycloalkyl and substituted or unsubstituted C4-C6 cycloalkyl, or when taken together, R 31 and R 32Form a monocyclic ring selected from the group consisting of heterocycloalkyl or heteroaryl;

[0019] R 33 、R 34 and R 35 are each independently selected from the group consisting of: a direct bond, a substituted or unsubstituted C1-C6 straight-chain alkyl group, a substituted or unsubstituted C3-C6 branched-chain alkyl group, a C1 alkyl group, a C2 alkyl group, a C3 alkyl group, a C4 alkyl group, a C5 alkyl group, a C6 alkyl group, an ether, -OCH2CH2-, -OCH2CH2CH2-, -OCH2CH2CH2CH2-, -NHCH2CH2-, -NHCH2CH2CH2-, and -NHCH2CH2CH2CH2-;

[0020] R 36 is selected from the group consisting of: hydrogen, a substituted or unsubstituted straight-chain alkyl group, a substituted or unsubstituted C1-C6 straight-chain alkyl group, a substituted or unsubstituted C1-C3 straight-chain alkyl group, a substituted or unsubstituted branched-chain alkyl group, a substituted or unsubstituted C3-C6 branched-chain alkyl group, methyl, ethyl, propyl, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted C3-C6 cycloalkyl group, a substituted or unsubstituted C4-C6 cycloalkyl group, heterocycloalkyl, and heteroaryl; and

[0021] m is an integer in the range of 0 to 20;

[0022] provided that the aminoalkyl-substituted disiloxane is not BRIEF DESCRIPTION OF THE DRAWINGS

[0023] These and other features, aspects, and advantages of the present disclosure will be better understood when the following detailed description is read with reference to the accompanying drawings, in which like characters represent like parts throughout all the drawings, wherein:

[0024] Figure 1 is an exemplary method flowchart in accordance with the present disclosure.

[0025] Unless otherwise specified, the drawings provided herein are intended to illustrate the features of embodiments of the present disclosure. It is believed that these features are applicable to a wide variety of systems including one or more embodiments of the present disclosure. Accordingly, the drawings are not intended to include all conventional features known to those of ordinary skill in the art that are required to practice the embodiments disclosed herein. DETAILED DESCRIPTION

[0026] The embodiments described herein overcome at least some of the disadvantages 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, the method comprising: I) forming a mixture comprising: a diamine or polyamine containing at least one primary amine group; and a silane; II) reacting the mixture in a first reaction; III) adding a hydrolyzing agent to the mixture; and IV) reacting the mixture in a second reaction to form the aminoalkyl-substituted disiloxane. Compared with known methods for preparing aminoalkyl-substituted disiloxanes, the exemplary embodiments described herein avoid side reactions and / or produce the desired product with higher yield and purity in fewer steps.

[0027] In many embodiments, the method is a one-pot synthesis. As used herein, a one-pot synthesis is a 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. A one-pot synthesis may include one reaction or more than one reaction. A one-pot synthesis is particularly advantageous in reducing reaction complexity and avoiding lengthy and expensive separation and purification.

[0028] In many embodiments, the aminoalkyl-substituted disiloxane is an amino-C1-C6-alkyl-substituted disiloxane. Embodiments comprising C1-C6 alkyl groups are thermodynamically more favorable for formation compared to other compounds comprising larger aminoalkyl substituents or alternative substituents. In some embodiments, the aminoalkyl-substituted disiloxane is an aminomethyl-substituted disiloxane.

[0029] Figure 1 is Exemplary Method Flowchart 110. In this exemplary embodiment, Method Flowchart 110 depicts the basic method steps of the exemplary embodiments described herein and is not intended to limit the method embodiments. First, a mixture 112 is formed, which comprises: a diamine or polyamine containing at least one primary amine group; and a silane. The mixture is reacted 114 in a first reaction, and a hydrolyzing agent 116 is added to the mixture. Then the mixture is reacted 118 in a second reaction to form the aminoalkyl-substituted disiloxane.

[0030] 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)

[0031]

[0032] wherein:

[0033] R 12 、R 13 、R 14 、R15 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 branched heteroalkyl, aryl, phenyl, heteroaryl, methyl, ethyl, propyl, isopropyl, butyl, pentyl and hexyl;

[0034] R 16 and R 17 Each independently selected from 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;

[0035] R 18 and R 19 Each independently selected from the group consisting of substituents of formula (IV)

[0036]

[0037] wherein:

[0038] The wavy bond represents the bonding position to formula (I);

[0039] R 25 、R 26 、R 27 、R 28 、R 29 and R 30 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;

[0040] R 31 and R 32 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 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 when taken together, R 31 and R 32Form a monocyclic ring selected from the group consisting of heterocycloalkyl or heteroaryl;

[0041] 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-chain alkyl, C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, ether, -OCH2CH2-, -OCH2CH2CH2-, -OCH2CH2CH2CH2-, -NHCH2CH2-, -NHCH2CH2CH2-, and -NHCH2CH2CH2CH2-;

[0042] 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-chain alkyl, substituted or unsubstituted C3-C6 branched-chain alkyl, methyl, ethyl, propyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted C3-C6 cycloalkyl, substituted or unsubstituted C4-C6 cycloalkyl, heterocycloalkyl, and heteroaryl; and

[0043] m is an integer in the range of 0 to 20, preferably an integer in the range of 0 to 10, and even more preferably an integer in the range of 0 to 3;

[0044] provided that the aminoalkyl-substituted disiloxane is not

[0045] In some embodiments, the aminoalkyl-substituted disiloxane is selected from the group consisting of:

[0046]

[0047]

[0048] and

[0049]

[0050] In some embodiments, the diamine or polyamine containing at least one primary amine group can be any suitable diamine or polyamine known in the art that promotes the methods described herein. In other embodiments, the diamine or polyamine containing at least one primary amine group is a compound of formula (II)

[0051]

[0052] wherein:

[0053] R1, R2, R3, R4, R5, and R6 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-chain alkyl, substituted or unsubstituted C3-C6 branched-chain alkyl, substituted or unsubstituted straight-chain heteroalkyl, substituted or unsubstituted branched-chain heteroalkyl, substituted or unsubstituted C3-C6 branched-chain heteroalkyl, aryl, phenyl, heteroaryl, methyl, ethyl, propyl, isopropyl, butyl, pentyl, and hexyl;

[0054] R7 and R8 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 C1-C3 straight-chain alkyl, substituted or unsubstituted branched-chain alkyl, substituted or unsubstituted C3-C6 branched-chain alkyl, methyl, ethyl, propyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted C3-C6 cycloalkyl, and substituted or unsubstituted C4-C6 cycloalkyl, or when taken together, R7 and R8 form a monocyclic ring selected from the group consisting of heterocycloalkyl or heteroaryl;

[0055] 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-chain alkyl, C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, ether, -OCH2CH2-, -OCH2CH2CH2-, -OCH2CH2CH2CH2-, -NHCH2CH2-, -NHCH2CH2CH2-, and -NHCH2CH2CH2CH2-; and

[0056] n is an integer in the range of 0 to 20, preferably an integer in the range of 0 to 10, and even more preferably an integer in the range of 0 to 3.

[0057] In some embodiments, the silane can be any suitable silane known in the art that promotes 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)

[0058]

[0059] wherein:

[0060] R 20 is selected from the group consisting of halide ions, fluoride ions, chloride ions, bromide ions, and iodide ions;

[0061] R 21 and R 22Each independently is selected from the group consisting of: hydrogen, a substituted or unsubstituted straight-chain alkyl group, a substituted or unsubstituted C1-C6 straight-chain alkyl group, a substituted or unsubstituted branched-chain alkyl group, a substituted or unsubstituted C3-C6 branched-chain alkyl group, a substituted or unsubstituted straight-chain heteroalkyl group, a substituted or unsubstituted branched-chain heteroalkyl group, an aryl group, a phenyl group, a heteroaryl group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a pentyl group, and a hexyl group;

[0062] R 23 and R 24 Each independently is selected from the group consisting of: a substituted or unsubstituted C1-C6 straight-chain alkyl group, a substituted or unsubstituted C3-C6 branched-chain alkyl group, a C1 alkyl group, a C2 alkyl group, a C3 alkyl group, a C4 alkyl group, a C5 alkyl group, a C6 alkyl group, an aryl group, and a phenyl group.

[0063] In some embodiments, R 23 and R 24 Each independently is selected from the group consisting of: a substituted or unsubstituted C1-C6 straight-chain alkyl group, a substituted or unsubstituted C3-C6 branched-chain alkyl group, a C1 alkyl group, a C2 alkyl group, a C3 alkyl group, a C4 alkyl group, a C5 alkyl group, and a C6 alkyl group, preferably a C1-C6 straight-chain alkyl group.

[0064] In some embodiments, R 23 is a C1 alkyl group.

[0065] In some embodiments, R 24 is a C1 alkyl group, a C2 alkyl group, a C3 alkyl group, a C4 alkyl group, a C5 alkyl group, a C6 alkyl group, an aryl group, or a phenyl group.

[0066] In some embodiments, the silane is In some embodiments, the silane is

[0067] In many embodiments, reacting the mixture in the first reaction 114 can be carried out under any suitable reaction conditions known in the art that facilitate the methods described herein. In some embodiments, reacting the mixture in the first reaction 114 includes stirring the mixture.

[0068] 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 to facilitate the methods described herein. In some embodiments, the elapsed time for the mixture to react in the first reaction 114 ranges from about 1 second to about 12 hours. In some embodiments, the elapsed time for the mixture to react in the first reaction 114 ranges from about 1 second to about 6 hours. In some embodiments, the elapsed time for the mixture to react in the first reaction 114 ranges from about 1 second to about 3 hours. In some embodiments, the elapsed time for the mixture to react in the first reaction 114 ranges from about 1 hour to about 3 hours. In some embodiments, the elapsed time for the mixture to react in the first reaction 114 ranges from about 2 hours to about 3 hours.

[0069] In some embodiments, reacting the mixture in the first reaction 114 includes dropwise adding a silane (such as chloromethyldimethyl ethoxysilane) to a pure diamine or polyamine containing at least one primary amine group within about 1 hour. Allow the reaction temperature to rise to about 90 °C due to the exothermic reaction and maintain this temperature during the reaction duration (a total of about 2 - 3 hours). During this period, the HCl salt of the amine is formed and may precipitate to different extents depending on the amine.

[0070] In some embodiments, the hydrolyzing agent is added dropwise 116 to the mixture. 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 116 over a time period ranging from about 1 second to about 12 hours. In some embodiments, the hydrolyzing agent 116 is added within 30 minutes and under exothermic conditions and then cooled to room temperature, and then the mixture is reacted in the second reaction 118.

[0071] In some embodiments, the hydrolyzing agent 116 is added within 30 minutes and under exothermic conditions, and then the mixture is reacted in the second reaction 118. In these embodiments, the reaction 118 is completed before the reaction mixture is cooled to room temperature.

[0072] In many embodiments, the hydrolyzing agent can be any suitable hydrolyzing agent known in the art to facilitate the methods described herein. In some embodiments, the hydrolyzing agent is an aqueous solution. In some embodiments, the hydrolyzing agent is water.

[0073] In many embodiments, reacting the mixture in the second reaction 118 can be carried out under any suitable reaction conditions known in the art to facilitate the methods described herein. In some embodiments, reacting the mixture in the second reaction 118 includes adjusting the temperature of the mixture. In some embodiments, reacting the mixture in the second reaction 118 includes cooling the mixture.

[0074] 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 with an organic solvent.

[0075] In some embodiments, extracting the aminoalkyl-substituted disiloxane from the reaction mixture comprises adding dropwise an organic solvent (such as chloroform and / or toluene) 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 separated, the aqueous layer is back-extracted with a minimal amount of organic solvent, and the combined organic layers are concentrated under vacuum, triturated once with an organic solvent, and then dried under vacuum.

[0076] In some embodiments, the aminoalkyl-substituted disiloxane is further purified. In some embodiments, further purification comprises using distillation, vacuum distillation, and / or heating. In some embodiments, further purification comprises using vacuum distillation to remove impurities and by-products. In these embodiments, the remaining material in the distillation flask is a product of higher purity relative to the product before purification.

[0077] In many embodiments, the mixture is reacted in a second reaction 118 for any suitable amount of time known in the art to facilitate the methods described herein. In some embodiments, the elapsed time for which the mixture is reacted in the second reaction 118 ranges from about 1 second to about 12 hours. In some embodiments, the elapsed time for which the mixture is reacted in the second reaction 118 ranges from about 1 second to about 6 hours. In some embodiments, the elapsed time for which the mixture is reacted in the second reaction 118 ranges from about 1 second to about 3 hours. In some embodiments, the elapsed time for which the mixture is reacted in the second reaction 118 ranges from about 1 hour to about 3 hours. In some embodiments, the elapsed time for which the mixture is reacted in the second reaction 118 ranges from about 2 hours to about 3 hours.

[0078] In many embodiments, the method may further comprise any other suitable processing steps known in the art to facilitate the success of the methods described herein. Such processing steps may include, but are not limited to, only washing, drying, filtering, purifying, separating, centrifuging, and any combination thereof. In some embodiments, the method further comprises washing the aminoalkyl-substituted disiloxane compound. In some embodiments, the method further comprises purifying the aminoalkyl-substituted disiloxane compound. In some embodiments, purification comprises using distillation, vacuum distillation, and / or heating. In some embodiments, the method further comprises removing volatile reaction by-products.

[0079] In some embodiments, the method comprises: I) forming a mixture comprising: a diamine or polyamine containing at least one primary amine group; and a chloromethyldimethylalkoxysilane; II) reacting the mixture in a first reaction by a controlled exothermic nature; III) adding a hydrolyzing 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.

[0080] In many embodiments, the aminoalkyl-substituted disiloxane can be used for any suitable purpose known in the art. In some embodiments, the aminoalkyl-substituted disiloxane is used in a carbon capture system. In some embodiments, the aminoalkyl-substituted disiloxane is used in amino-organosilicon-based products.

[0081] Other aspects of the disclosure are provided by the subject matter of the following clauses:

[0082] 1. A method for preparing an aminoalkyl-substituted disiloxane, the method comprising: I) forming a mixture comprising: a diamine or polyamine containing at least one primary amine group; and a silane; II) reacting the mixture in a first reaction; III) adding a hydrolyzing agent to the mixture; and IV) reacting the mixture in a second reaction to form the aminoalkyl-substituted disiloxane.

[0083] 2. The method according to the previous clause, wherein the aminoalkyl-substituted disiloxane is a compound of formula (I)

[0084]

[0085] wherein:

[0086] R 12 、R 13 、R 14 、R 15 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-chain alkyl, substituted or unsubstituted C3-C6 branched-chain alkyl, substituted or unsubstituted straight-chain heteroalkyl, substituted or unsubstituted branched-chain heteroalkyl, aryl, phenyl, heteroaryl, methyl, ethyl, propyl, isopropyl, butyl, pentyl, and hexyl;

[0087] 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-chain alkyl, C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, and C6 alkyl;

[0088] R 18 and R 19 each independently selected from the group consisting of substituents of formula (IV)

[0089]

[0090] wherein:

[0091] The wavy bond represents the bonding position to formula (I);

[0092] R 25 、R 26 、R 27 、R 28 、R 29 and R 30 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-chain alkyl, substituted or unsubstituted C3-C6 branched-chain alkyl, substituted or unsubstituted straight-chain heteroalkyl, substituted or unsubstituted C1-C6 straight-chain heteroalkyl, substituted or unsubstituted branched-chain heteroalkyl, substituted or unsubstituted C3-C6 branched-chain heteroalkyl, aryl, heteroaryl, methyl, ethyl, propyl, isopropyl, butyl, pentyl and hexyl;

[0093] R 31 and R 32 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 C1-C3 straight-chain alkyl, substituted or unsubstituted branched-chain alkyl, substituted or unsubstituted C3-C6 branched-chain alkyl, methyl, ethyl, propyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted C3-C6 cycloalkyl and substituted or unsubstituted C4-C6 cycloalkyl, or when taken together, R 31 and R 32 form a monocyclic ring selected from the group consisting of heterocycloalkyl or heteroaryl;

[0094] R 33 、R 34 and R 35 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-chain alkyl, C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, ether, -OCH2CH2-, -OCH2CH2CH2-, -OCH2CH2CH2CH2-, -NHCH2CH2-, -NHCH2CH2CH2- and -NHCH2CH2CH2CH2-;

[0095] R 36selected from the group consisting of: hydrogen, a substituted or unsubstituted straight-chain alkyl group, a substituted or unsubstituted C1-C6 straight-chain alkyl group, a substituted or unsubstituted C1-C3 straight-chain alkyl group, a substituted or unsubstituted branched alkyl group, a substituted or unsubstituted C3-C6 branched alkyl group, methyl, ethyl, propyl, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted C3-C6 cycloalkyl group, a substituted or unsubstituted C4-C6 cycloalkyl group, a heterocycloalkyl group, and a heteroaryl group; and

[0096] m is an integer in the range of 0 to 20.

[0097] 3. The method according to any one of the preceding clauses, wherein the aminoalkyl-substituted disiloxane is a compound selected from the group consisting of:

[0098]

[0099]

[0100] and

[0101] 4. The method according to any one of the preceding clauses, wherein the diamine or polyamine containing at least one primary amine group is a compound of formula (II)

[0102]

[0103] wherein:

[0104] R1, R2, R3, R4, R5 and R6 are each independently selected from the group consisting of:

[0105] hydrogen, a substituted or unsubstituted straight-chain alkyl group, a substituted or unsubstituted C1-C6 straight-chain alkyl group, a substituted or unsubstituted branched alkyl group, a substituted or unsubstituted C3-C6 branched alkyl group, a substituted or unsubstituted straight-chain heteroalkyl group, a substituted or unsubstituted branched heteroalkyl group, a substituted or unsubstituted C3-C6 branched heteroalkyl group, an aryl group, a phenyl group, a heteroaryl group, methyl, ethyl, prop

[0106] yl, isopropyl, butyl, pentyl and hexyl;

[0107] R7 and R8 are each independently selected from the group consisting of: hydrogen, a substituted or unsubstituted straight-chain alkyl group, a substituted or unsubstituted C1-C6 straight-chain alkyl group, a substituted or unsubstituted C1-C3 straight-chain alkyl group, a substituted or unsubstituted branched alkyl group, a substituted or unsubstituted C3-C6 branched alkyl group, methyl, ethyl, propyl, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted C3-C6 cycloalkyl group and a substituted or unsubstituted C4-C6 cycloalkyl group, or when taken together, R7 and R8 form a monocyclic ring selected from the group consisting of a heterocycloalkyl group or a heteroaryl group;

[0108] R9, R 10 and R 11 each independently selected from the group consisting of: a direct bond, a substituted or unsubstituted C1-C6 straight-chain alkyl group, a substituted or unsubstituted C3-C6 branched-chain alkyl group, a C1 alkyl group, a C2 alkyl group, a C3 alkyl group, a C4 alkyl group, a C5 alkyl group, a C6 alkyl group, an ether, -OCH2CH2-, -OCH2CH2CH2-, -OCH2CH2CH2CH2-, -NHCH2CH2-, -NHCH2CH2CH2-, and -NHCH2CH2CH2CH2-; and

[0109] n is an integer in the range of 0 to 20.

[0110] The method according to any one of the preceding clauses, wherein the silane is a compound of formula (III)

[0111]

[0112] wherein:

[0113] R 20 is selected from the group consisting of a halide ion, a fluoride ion, a chloride ion, a bromide ion, and an iodide ion;

[0114] R 21 and R 22 each independently selected from the group consisting of hydrogen, a substituted or unsubstituted straight-chain alkyl group, a substituted or unsubstituted C1-C6 straight-chain alkyl group, a substituted or unsubstituted branched-chain alkyl group, a substituted or unsubstituted C3-C6 branched-chain alkyl group, a substituted or unsubstituted straight-chain heteroalkyl group, a substituted or unsubstituted branched-chain heteroalkyl group, an aryl group, a phenyl group, a heteroaryl group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a pentyl group, and a hexyl group;

[0115] R 23 and R 24 each independently selected from the group consisting of a substituted or unsubstituted C1-C6 straight-chain alkyl group, a substituted or unsubstituted C3-C6 branched-chain alkyl group, a C1 alkyl group, a C2 alkyl group, a C3 alkyl group, a C4 alkyl group, a C5 alkyl group, a C6 alkyl group, an aryl group, and a phenyl group.

[0116] 6. The method according to any one of the preceding clauses, wherein the silane is

[0117] 7. The method according to any one of the preceding clauses, wherein reacting the mixture in the first reaction comprises stirring the mixture.

[0118] 8. The method according to any one of the preceding clauses, wherein reacting the mixture in the first reaction comprises reacting the mixture for a first period of time.

[0119] 9. The method according to any one of the preceding clauses, wherein the first time period is a time in the range of from about 1 second to about 12 hours.

[0120] 10. The method according to any one of the preceding clauses, wherein the hydrolyzing agent is an aqueous solution.

[0121] 11. The method according to any one of the preceding clauses, wherein the hydrolyzing agent is water.

[0122] 12. The method according to any one of the preceding clauses, wherein the hydrolyzing agent is added to the mixture during a second time period.

[0123] 13. The method according to any one of the preceding clauses, wherein the second time period is a time in the range of from about 1 second to about 12 hours.

[0124] 14. The method according to any one of the preceding clauses, wherein the hydrolyzing agent is added dropwise to the mixture.

[0125] 15. The method according to any one of the preceding clauses, wherein the method further comprises purifying the aminoalkyl-substituted disiloxane.

[0126] 16. The method according to any one of the preceding clauses, wherein at least one method step comprises adjusting the temperature of the mixture.

[0127] 17. The method according to any one of the preceding clauses, wherein reacting the mixture in a second reaction comprises adjusting the temperature of the mixture.

[0128] 18. The method according to any one of the preceding clauses, wherein reacting the mixture in a second reaction comprises cooling the mixture.

[0129] 19. The method according to any one of the preceding clauses, wherein the method is a one-pot synthesis.

[0130] 20. An aminoalkyl-substituted disiloxane prepared by the method according to any one of the preceding clauses.

[0131] 21. An aminoalkyl-substituted disiloxane of formula (I)

[0132]

[0133] Wherein:

[0134] R 12 、R 13 、R 14 、R 15Each independently is selected from the group consisting of: hydrogen, a substituted or unsubstituted straight-chain alkyl group, a substituted or unsubstituted C1-C6 straight-chain alkyl group, a substituted or unsubstituted branched-chain alkyl group, a substituted or unsubstituted C3-C6 branched-chain alkyl group, a substituted or unsubstituted straight-chain heteroalkyl group, a substituted or unsubstituted branched-chain heteroalkyl group, an aryl group, a phenyl group, a heteroaryl group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a pentyl group, and a hexyl group;

[0135] R 16 and R 17 Each independently is selected from the group consisting of: a direct bond, a substituted or unsubstituted C1-C6 straight-chain alkyl group, a substituted or unsubstituted C3-C6 branched-chain alkyl group, a C1 alkyl group, a C2 alkyl group, a C3 alkyl group, a C4 alkyl group, a C5 alkyl group, and a C6 alkyl group;

[0136] R 18 and R 19 Each independently is selected from the group consisting of substituents of formula (IV)

[0137]

[0138] wherein:

[0139] The wavy bond represents the bonding position to formula (I);

[0140] R 25 、R 26 、R 27 、R 28 、R 29 and R 30 Each independently is selected from the group consisting of: hydrogen, a substituted or unsubstituted straight-chain alkyl group, a substituted or unsubstituted C1-C6 straight-chain alkyl group, a substituted or unsubstituted branched-chain alkyl group, a substituted or unsubstituted C3-C6 branched-chain alkyl group, a substituted or unsubstituted straight-chain heteroalkyl group, a substituted or unsubstituted C1-C6 straight-chain heteroalkyl group, a substituted or unsubstituted branched-chain heteroalkyl group, a substituted or unsubstituted C3-C6 branched-chain heteroalkyl group, an aryl group, a heteroaryl group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a pentyl group, and a hexyl group;

[0141] R 31 and R 32 Each independently is selected from the group consisting of: hydrogen, a substituted or unsubstituted straight-chain alkyl group, a substituted or unsubstituted C1-C6 straight-chain alkyl group, a substituted or unsubstituted C1-C3 straight-chain alkyl group, a substituted or unsubstituted branched-chain alkyl group, a substituted or unsubstituted C3-C6

[0142] branched-chain alkyl group, a methyl group, an ethyl group, a propyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted C3-C6 cycloalkyl group, and a substituted or unsubstituted C4-C6 cycloalkyl group, or when taken together, R 31 and R 32Form a monocyclic ring selected from the group consisting of heterocycloalkyl or heteroaryl;

[0143] 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-chain alkyl,

[0144] C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, ether, -

[0145] OCH2CH2-, -OCH2CH2CH2-, -OCH2CH2CH2CH2-, -NHCH2CH2-,

[0146] -NHCH2CH2CH2- and -NHCH2CH2CH2CH2-;

[0147] 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-chain alkyl, substituted or unsubstituted C3-C6 branched-chain alkyl, methyl, ethyl, propyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted C3-C6 cycloalkyl, substituted or unsubstituted C4-C6 cycloalkyl, heterocycloalkyl and heteroaryl; and

[0148] m is an integer in the range of 0 to 20;

[0149] provided that the aminoalkyl-substituted disiloxane is not

[0150] 22. The aminoalkyl-substituted disiloxane according to the previous clause, wherein the aminoalkyl-substituted disiloxane is a compound selected from the group consisting of:

[0151]

[0152]

[0153] and

[0154]

[0155] The mention of "some embodiments" in the above description is not intended to be construed as precluding the existence of additional embodiments that also include the described features.

[0156] Example

[0157] Without further elaboration, it is believed that those skilled in the art can make the most of the present invention using the foregoing description. Therefore, the following examples are to be construed as illustrative only and in no way limit the disclosure. The starting materials for the following examples need not be prepared by a specific preparation run, the procedure of which is described in other examples. It should also be understood that any numerical range recited herein includes all values from the lower value to the upper value. For example, if the range is stated as 10 to 50, values such as 12 to 30, 20 to 40, or 30 to 50 are intended to be expressly enumerated in this specification. These are merely examples of specific intentions, and all possible combinations of numerical values between and including the lowest and highest values recited are considered to be expressly stated in this application.

[0158] Example 1. Synthesis of aminomethyl-substituted disiloxane 1,3-bis(2-aminoethylamino methyl)tetramethyldisiloxane using 4 equivalents of ethylenediamine 。

[0159] Ethylenediamine (396 mL, 5.93 mol) was added to a 2 L three-necked round-bottom flask equipped with a addition funnel and a reflux condenser. The flask was placed in an ice-water bath and the headspace was purged with N2. Chloromethyldimethyl ethoxysilane (240 mL, 1.48 mol) was added to the addition funnel and added dropwise to the ethylenediamine over 1 hour, during which the reaction mixture exothermed to 90 °C to 100 °C. After an additional 1 hour, the reaction was judged complete by 1 1H NMR, at which time 300 mL of water was added dropwise to the reaction mixture over 30 minutes, resulting in exotherm. The reaction mixture was cooled to room temperature with stirring, at which time 300 mL of chloroform was added dropwise. The resulting mixture was stirred vigorously for 1 hour, after which the organic layer was separated 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 mainly cyclic by-products and some product was collected at 40 °C to 80 °C and 380 mTorr. By 1 1H NMR spectral analysis, the purity of the remaining material (167 g, 81% yield) was >75%. 1 1H 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).

[0160] Example 2. Synthesis of aminomethyl-substituted disiloxane 1,3-bis(3-aminopropylaminomethyl)tetramethyldisilox ane 。

[0161] Follow the same procedure as in Example 1, but in a 250 mL three-necked flask, use 1,3-propanediamine (52 mL, 0.62 mol), chloromethyldimethylethoxysilane (25 mL, 0.15 mol), 40 mL of water and 40 mL of chloroform. Then purify the resulting material by vacuum distillation. Collect the first fraction mainly containing cyclic by-products and some products at 40 °C to 65 °C. By 1 1H NMR spectrum analysis, the purity of the remaining material (17.6 g, 74% yield) was considered to be >95%. 1 1H NMR (CDCl3) δ: 2.75 (t, 4H, H2NCH2CH2CH2), 2.65 (t, 4H, H2NCH2), 2.05 (s, 4H, SiCH2), 1.60 (multiplet, 4H, H2NCH2CH2), 1.30 (br s, 6H, NH&NH2), 0.12 (s, 12H, SiCH3).

[0162] Example 3. Synthesis of aminomethyl-substituted disiloxane 1,3-bis(2-methyl-3-aminopropylaminomethyl)tetramethy ldisiloxane .

[0163] Follow the same procedure as in Example 1, but in a 15 mL flask, use 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. Then purify the resulting material by vacuum distillation. Collect the first fraction containing by-products and some products at 110 °C. By 1 1H NMR spectrum analysis, the purity of the remaining material (0.60 g, 51% yield) was considered to be >95%. 1 1H NMR (CDCl3) δ: 2.8 - 2.5 (overlapping multiplets, 8H, H2NCH2CH(CH3)CH2), 2.05 (multiplet, 4H, SiCH2), 1.75 (multiplet, 2H, H2NCH2CH), 1.95 (br s, 6H, NH&NH2), 0.90 (d, 6H, H2NCH2CHCH3) 0.12 (s, 12H, SiCH3).

[0164] Example 4. Synthesis of aminomethyl-substituted disiloxane 1,3-bis(2,2-dimethyl-3-aminopropylaminomethyl)tetra methyldisiloxane .

[0165] Follow the same procedure as in Example 1, but in a 15 mL flask, use 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. Then purify the resulting material by vacuum distillation. Collect the first fraction containing by-products and some products at 80 °C to 90 °C. By 11H NMR spectrum analysis showed that the purity of the remaining material (0.95 g, 74% yield) was >95%. 1 1H 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).

[0166] Example 5. Synthesis of aminomethyl-substituted disiloxane 1,3-bis(2-aminoethylamino methyl)tetramethyldisiloxane using 8 equivalents of ethylenediamine 。

[0167] Ethylenediamine (793 mL, 11.9 mol) was added to a 2 L three-necked round-bottom flask equipped with a dropping 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 dropping funnel and added dropwise to the ethylenediamine over 1 hour, during which the reaction mixture exothermed to 90 °C to 100 °C. After another 1 hour, the reaction was judged to be complete by 1 1H NMR. At this time, 300 mL of water was added dropwise to the reaction mixture within 30 minutes, resulting in exotherm. The reaction mixture was cooled to room temperature while stirring, and then 300 mL of chloroform was added dropwise. The resulting mixture was stirred vigorously for 1 hour, after which the organic layer was separated, and the aqueous layer was extracted with a minimum volume of chloroform. The combined organic layers were dried under reduced pressure at room temperature. Then the resulting material was purified by vacuum distillation. The first fraction mainly containing cyclic by-products and some products was collected at 40 °C to 80 °C and 380 mTorr. By 1 1H NMR spectrum analysis, the purity of the remaining material (326 g, 79% yield) was >90%. 1 1H 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).

[0168] Example 6. Synthesis of aminomethyl-substituted disiloxane 1,3-bis(2-aminoethylamino methyl)tetramethyldisiloxane using 10 equivalents of ethylenediamine 。

[0169] Ethylenediamine (400 mL, 5.99 mol) was added to a 2 L three-necked round-bottom flask equipped with a dropping 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 dropping funnel and added dropwise to the ethylenediamine over 1 hour, during which the reaction mixture exothermed to 90 °C to 100 °C. After another 1 hour, by1 The reaction completion was judged by \(^1H\) NMR. At this time, 300 mL of water was added dropwise to the reaction mixture within 30 minutes, resulting in heat release. The reaction mixture was cooled to room temperature while stirring, and then 300 mL of chloroform was added dropwise. The resulting mixture was vigorously stirred for 1 hour, after which the organic layer was separated, and the aqueous layer was extracted with a minimum volume of chloroform. The combined organic layers were dried under reduced pressure at room temperature. Then the resulting material was purified by vacuum distillation. The first fraction mainly containing cyclic by-products and some products was collected at 40 °C to 80 °C and 380 mTorr. By 1 \(^1H\) NMR spectrum analysis, the purity of the remaining material (117 g, 70% yield) was >95%. 1 \(^1H\) 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).

[0170] Comparative Example 1: Attempted synthesis of aminomethyl-substituted disiloxane 1, 3-bis(2-aminoethylaminomethyl)tetramethyldisiloxane from 1,3-bis(chloromethyl)tetramethyldisiloxane 。

[0171] Ethylenediamine (13 g, 0.216 mol, 10 equivalents) was added to a 50 ml three-necked round-bottom flask equipped with a nitrogen layer, a magnetic stir bar, a condenser, and an addition funnel. Then it was heated to 110 °C in an oil bath. Once the temperature in the oil bath was stable, 1,3-bis(chloromethyl)-1,1,3,3-tetramethyldisiloxane (5 g, 0.0216 mol) was added dropwise within 2 hours. The reactants were stirred overnight at this temperature. The reactants were cooled, and 1 \(^1H\) NMR analysis was performed to check if the reaction was complete. Then the reaction mixture was poured into a 250 ml separatory funnel, partitioned between chloroform and 10% NaOH, washed 3 times with deionized water, once with saturated sodium chloride, and then dried over anhydrous potassium chloride. After filtration, chloroform was stripped off on a rotary evaporator to obtain a clear, colorless, viscous liquid. 1 \(^1H\) NMR analysis showed a product mixture containing the cyclic by-product 2,2,6,6-tetramethyl-1-oxa-4-aza-2,6-disilacyclohexane-4-ethylamine. The desired 1,3-bis(2-aminoethylaminomethyl)tetramethyldisiloxane was not formed.

[0172] Comparative Example 2: Attempted synthesis of aminomethyl-substituted disiloxane 1, 3-bis(2-aminoethylaminomethyl)tetramethyldisiloxane from 1,3-bis(iodomethyl)tetramethyldisiloxane 。

[0173] Ethylenediamine (13 g, 0.216 mol, 10 equivalents) 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 h. The reactants were stirred overnight at room temperature. 1 1H NMR analysis was performed to check if 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 deionized water, once with saturated sodium chloride, and then dried over anhydrous potassium chloride. After filtration, the chloroform was stripped off on a rotary evaporator to give a clear colorless viscous liquid. 1 1H NMR analysis showed the clean formation of the cyclic byproduct 2,2,6,6-tetramethyl-1-oxa-4-aza-2,6-disilacyclohexane-4-ethylamine. The desired 1,3-bis(2-aminoethylaminomethyl)tetramethyldisiloxane was not formed. The 1H NMR of 2,2,6,6-tetramethyl-1-oxa-4-aza-2,6-disilacyclohexane-4-ethylamine 1 (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).

[0174] Unless otherwise indicated, as used herein, approximate language, such as “substantially,” “essentially,” and “about,” indicates that, as would be recognized by one of ordinary skill in the art, the so-modified term may apply only to an approximate degree, and not an absolute or perfect degree. Thus, values modified by one or more of these terms, such as “about,” “approximately,” and “substantially,” are not limited to the specified exact value. In at least some instances, the approximate language may correspond to the precision of the instrument used for measuring the value. In addition, unless otherwise indicated, the terms “first,” “second,” etc. are used herein only as labels and are not intended to impose an order, position, or ranking requirement on the items to which these terms refer. Further, for example, a reference to a “second” item does not require or preclude the existence of, for example, a “first” or lower-numbered item or a “third” or higher-numbered item.

[0175] Although specific features of various embodiments of the present invention may be shown in some figures and not in others, this is for convenience only. In addition, the above description referring to “some embodiments” is not to be construed as excluding the existence of additional embodiments that also incorporate the described features. Any feature of any figure may be cited and / or claimed in combination with any feature of any other figure in accordance with the principles of the present invention.

[0176] This written description uses examples to disclose the present invention, including the best mode, and also enables any person skilled in the art to practice the present invention, including making and using any device or system and performing any combined method. The patentable scope of the present invention is defined by the claims and may include other examples that occur to those skilled in the art. If such other examples have structural elements that are not different from the literal language of the claims, or if they include equivalent structural elements that have no substantial difference from the literal language of the claims, then such other examples are intended to be within the scope of the claims.

[0177] It will be readily understood by those skilled in the art that some substituents of the present disclosure are dependent on the presence of other substituents and are thus optional. For example, in Formula II, when R9 is a direct bond, R1 and R2 are optional substituents that do not exist in the compound. Similarly, in Formula II, when n is 0, there is a direct bond between R9 and R 10 and R3, R4, and R 11 are optional substituents that do not exist in the compound. The optionality of a substituent in one embodiment does not limit the presence of a substituent in another embodiment.

[0178] As used herein, the term "alkyl", whether used alone or in a compound word such as "haloalkyl", includes straight-chain or branched-chain alkyls such as methyl, ethyl, n-propyl, and isopropyl, or the different butyl, pentyl, or hexyl isomers. An alkyl defined by a plurality of carbon atoms, such as C6 alkyl, should be understood to have that many carbon atoms but is not otherwise limited.

[0179] As used herein, the term "heteroalkyl" denotes an alkyl chain in which at least one of the atoms forming the chain backbone is not carbon.

[0180] As used herein, "aminoalkyl" includes an N group substituted by a straight-chain or branched-chain alkyl.

[0181] As used herein, the term "halogen" or "halide", whether used alone or in a compound word such as "haloalkyl", includes fluorine, chlorine, bromine, or iodine. Further, when used in a compound word such as "haloalkyl", the alkyl may be partially or fully substituted by the same or different halogen atoms. Examples of "haloalkyl" include F3C, ClCH2, CF3CH2, and CF3CCl2. The definition of terms such as "haloalkoxy" is similar to the term "haloalkyl". Examples of "haloalkoxy" include CF3O, CCl3CH2O, F2CHCH2CH2O, and CF3CH2O.

[0182] As used herein, the term "heterocycle" means a ring in which at least one of the atoms forming the ring skeleton is not carbon. Unless otherwise specified, the heterocycle may be a saturated, partially unsaturated or fully unsaturated ring. When a fully unsaturated heterocycle satisfies the Hückel rule, the ring is also referred to as a "heteroaryl" or aromatic heterocycle. A "saturated heterocycle" means a heterocycle containing only single bonds between ring members.

Claims

1. A method for preparing an aminoalkyl-substituted disiloxane, the method comprising: I) Form a mixture comprising: a diamine or polyamine containing at least one primary amine group; and a silane; II) React the mixture in a first reaction; III) Add a hydrolyzing agent to the mixture; and IV) React the mixture in a second reaction to form the aminoalkyl-substituted disiloxane.

2. The method according to claim 1, wherein the aminoalkyl-substituted disiloxane is a compound of formula (I) Wherein: R 12 、R 13 、R 14 、R 15 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-chain alkyl, substituted or unsubstituted C3-C6 branched-chain alkyl, substituted or unsubstituted straight-chain heteroalkyl, substituted or unsubstituted branched-chain heteroalkyl, aryl, phenyl, heteroaryl, methyl, ethyl, propyl, isopropyl, butyl, pentyl, and hexyl; R 16 and R 17 each independently selected from the group consisting of: a direct bond, a substituted or unsubstituted C1-C6 straight-chain alkyl group, a substituted or unsubstituted C3-C6 branched-chain alkyl group, a C1 alkyl group, a C2 alkyl group, a C3 alkyl group, a C4 alkyl group, a C5 alkyl group, and a C6 alkyl group; R 18 and R 19 each independently selected from the group consisting of the substituents of formula (IV) Wherein: The wavy bond represents the bonding position to formula (I); R 25 、R 26 、R 27 、R 28 、R 29 and R 30 each independently is selected from the group consisting of: hydrogen, a substituted or unsubstituted straight-chain alkyl group, a substituted or unsubstituted C1-C6 straight-chain alkyl group, a substituted or unsubstituted branched-chain alkyl group, a substituted or unsubstituted C3-C6 branched-chain alkyl group, a substituted or unsubstituted straight-chain heteroalkyl group, a substituted or unsubstituted C1-C6 straight-chain heteroalkyl group, a substituted or unsubstituted branched-chain heteroalkyl group, a substituted or unsubstituted C3-C6 branched-chain heteroalkyl group, an aryl group, a heteroaryl group, methyl, ethyl, propyl, isopropyl, butyl, pentyl, and hexyl; R 31 and R 32 each independently is selected from the group consisting of hydrogen, a substituted or unsubstituted straight-chain alkyl group, a substituted or unsubstituted C1-C6 straight-chain alkyl group, a substituted or unsubstituted C1-C3 straight-chain alkyl group, a substituted or unsubstituted branched-chain alkyl group, a substituted or unsubstituted C3-C6 branched-chain alkyl group, methyl, ethyl, propyl, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted C3-C6 cycloalkyl group, and a substituted or unsubstituted C4-C6 cycloalkyl group, or when taken together, R 31 and R 32 form a monocyclic ring selected from the group consisting of a heterocycloalkyl group or a heteroaryl group; R 33 、R 34 and R 35 are each independently selected from the group consisting of: a direct bond, a substituted or unsubstituted C1-C6 straight-chain alkyl group, a substituted or unsubstituted C3-C6 branched-chain alkyl group, a C1 alkyl group, a C2 alkyl group, a C3 alkyl group, a C4 alkyl group, a C5 alkyl group, a C6 alkyl group, an ether, -OCH2CH2-, -OCH2CH2CH2-, -OCH2CH2CH2CH2-, -NHCH2CH2-, -NHCH2CH2CH2-, and -NHCH2CH2CH2CH2-; R 36 selected from the group consisting of hydrogen, a substituted or unsubstituted straight-chain alkyl group, a substituted or unsubstituted C1-C6 straight-chain alkyl group, a substituted or unsubstituted C1-C3 straight-chain alkyl group, a substituted or unsubstituted branched-chain alkyl group, a substituted or unsubstituted C3-C6 branched-chain alkyl group, methyl, ethyl, propyl, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted C3-C6 cycloalkyl group, a substituted or unsubstituted C4-C6 cycloalkyl group, a heterocycloalkyl group, and a heteroaryl group; and m is an integer in the range of 0 to 20.

3. The method according to claim 1, wherein the aminoalkyl-substituted disiloxane is a compound selected from the group consisting of:

4. The method according to claim 1, wherein the diamine or polyamine containing at least one primary amine group is a compound of formula (II) Wherein: R1, R2, R3, R4, R5, and R6 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-chain alkyl, substituted or unsubstituted C3-C6 branched-chain alkyl, substituted or unsubstituted straight-chain heteroalkyl, substituted or unsubstituted branched-chain heteroalkyl, substituted or unsubstituted C3-C6 branched-chain heteroalkyl, aryl, phenyl, heteroaryl, methyl, ethyl, propyl, isopropyl, butyl, pentyl, and hexyl; R7 and R8 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 C1-C3 straight-chain alkyl, substituted or unsubstituted branched-chain alkyl, substituted or unsubstituted C3-C6 branched-chain alkyl, methyl, ethyl, propyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted C3-C6 cycloalkyl, and substituted or unsubstituted C4-C6 cycloalkyl, or when taken together, R7 and R8 form a monocyclic ring selected from the group consisting of heterocycloalkyl or heteroaryl; R9, R 10 and R 11 each independently selected from the group consisting of: a direct bond, a substituted or unsubstituted C1-C6 straight-chain alkyl group, a substituted or unsubstituted C3-C6 branched-chain alkyl group, a C1 alkyl group, a C2 alkyl group, a C3 alkyl group, a C4 alkyl group, a C5 alkyl group, a C6 alkyl group, an ether, -OCH2CH2-, -OCH2CH2CH2-, -OCH2CH2CH2CH2-, -NHCH2CH2-, -NHCH2CH2CH2-, and -NHCH2CH2CH2CH2-; and n is an integer in the range of 0 to 20.

5. The method according to claim 1, wherein the silane is a compound of formula (III) Wherein: R 20 selected from the group consisting of a halogen ion, a fluoride ion, a chloride ion, a bromide ion, and an iodide ion; R 21 and R 22 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-chain alkyl, substituted or unsubstituted C3-C6 branched-chain alkyl, substituted or unsubstituted straight-chain heteroalkyl, substituted or unsubstituted branched-chain heteroalkyl, aryl, phenyl, heteroaryl, methyl, ethyl, propyl, isopropyl, butyl, pentyl, and hexyl; R 23 and R 24 each independently selected from the group consisting of: substituted or unsubstituted C1-C6 straight-chain alkyl, substituted or unsubstituted C3-C6 branched-chain alkyl, C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, aryl, and phenyl.

6. The method according to claim 1, wherein the silane is 7. The method according to claim 1, wherein reacting the mixture in the first reaction comprises stirring the mixture.

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

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

10. The method according to claim 1, wherein the hydrolyzing agent is an aqueous solution.

11. The method according to claim 1, wherein the hydrolyzing agent is water.

12. The method according to claim 1, wherein the hydrolyzing agent is added to the mixture within a second period of time.

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

14. The method according to claim 1, wherein the hydrolyzing agent is added dropwise to the mixture.

15. The method according to claim 1, wherein the method further comprises purifying the aminoalkyl-substituted disiloxane.

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

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

18. The method according to claim 1, wherein reacting the mixture in the second reaction comprises cooling the mixture.

19. The method according to claim 1, wherein the method is a one-pot synthesis.

20. An aminoalkyl-substituted disiloxane, wherein the aminoalkyl-substituted disiloxane is prepared by the method according to claim 1.

21. An aminoalkyl-substituted disiloxane of formula (I) Wherein: R 12 、R 13 、R 14 、R 15 Each independently selects from the group consisting of: hydrogen, a substituted or unsubstituted straight-chain alkyl group, a substituted or unsubstituted C1-C6 straight-chain alkyl group, a substituted or unsubstituted branched-chain alkyl group, a substituted or unsubstituted C3-C6 branched-chain alkyl group, a substituted or unsubstituted straight-chain heteroalkyl group, a substituted or unsubstituted branched-chain heteroalkyl group, an aryl group, a phenyl group, a heteroaryl group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a pentyl group, and a hexyl group; R 16 and R 17 each independently selected from the group consisting of: a direct bond, a substituted or unsubstituted C1-C6 straight-chain alkyl group, a substituted or unsubstituted C3-C6 branched-chain alkyl group, a C1 alkyl group, a C2 alkyl group, a C3 alkyl group, a C4 alkyl group, a C5 alkyl group, and a C6 alkyl group; R 18 and R 19 each independently selected from the group consisting of the substituents of formula (IV) Wherein: The wavy bond represents the bonding position 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, a substituted or unsubstituted straight-chain alkyl group, a substituted or unsubstituted C1-C6 straight-chain alkyl group, a substituted or unsubstituted branched-chain alkyl group, a substituted or unsubstituted C3-C6 branched-chain alkyl group, a substituted or unsubstituted straight-chain heteroalkyl group, a substituted or unsubstituted C1-C6 straight-chain heteroalkyl group, a substituted or unsubstituted branched-chain heteroalkyl group, a substituted or unsubstituted C3-C6 branched-chain heteroalkyl group, an aryl group, a heteroaryl group, methyl, ethyl, propyl, isopropyl, butyl, pentyl, and hexyl; R 31 and R 32 each independently is selected from the group consisting of: hydrogen, a substituted or unsubstituted straight-chain alkyl group, a substituted or unsubstituted C1-C6 straight-chain alkyl group, a substituted or unsubstituted C1-C3 straight-chain alkyl group, a substituted or unsubstituted branched-chain alkyl group, a substituted or unsubstituted C3-C6 branched-chain alkyl group, methyl, ethyl, propyl, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted C3-C6 cycloalkyl group, and a substituted or unsubstituted C4-C6 cycloalkyl group, or when taken together, R 31 and R 32 form a monocyclic ring selected from the group consisting of a heterocycloalkyl group or a heteroaryl group; R 33 、R 34 and R 35 are each independently selected from the group consisting of: a direct bond, a substituted or unsubstituted C1-C6 straight-chain alkyl group, a substituted or unsubstituted C3-C6 branched-chain alkyl group, a C1 alkyl group, a C2 alkyl group, a C3 alkyl group, a C4 alkyl group, a C5 alkyl group, a C6 alkyl group, an ether, -OCH2CH2-, -OCH2CH2CH2-, -OCH2CH2CH2CH2-, -NHCH2CH2-, -NHCH2CH2CH2- and -NHCH2CH2CH2CH2-; R 36 is selected from the group consisting of: hydrogen, a substituted or unsubstituted straight-chain alkyl group, a substituted or unsubstituted C1-C6 straight-chain alkyl group, a substituted or unsubstituted C1-C3 straight-chain alkyl group, a substituted or unsubstituted branched-chain alkyl group, a substituted or unsubstituted C3-C6 branched-chain alkyl group, methyl, ethyl, propyl, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted C3-C6 cycloalkyl group, a substituted or unsubstituted C4-C6 cycloalkyl group, a heterocycloalkyl group, and a heteroaryl group; and m is an integer in the range of 0 to 20; provided that the aminoalkyl-substituted disiloxane is not 22. The aminoalkyl-substituted disiloxane according to claim 21, wherein the aminoalkyl-substituted disiloxane is a compound selected from the group consisting of:

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