Aldehyde – amine curable polyorganosiloxane composition and methods for the preparation and use thereof

Abstract

A curable composition includes a monoamine-functional organosilicon compound and an aldehyde-functional organosilicon compound. The composition may cure at room temperature without the use of a tin catalyst. The composition may be used to prepare various cured products, such as a sealant or elastomer.

Description

ALDEHYDE – AMINE CURABLE POLYORGANOSILOXANE COMPOSITION AND METHODS FOR THE PREPARATION AND USE THEREOF CROSS REFERENCE TO RELATED APPLICATIONS

[0001] This application claims the benefit under 35 U.S.C. §119 (e) of U.S. Provisional Patent Application No.63 / 655,635; U.S. Provisional Patent Application No.63 / 655,636; and U.S. Provisional Patent Application No.63 / 655,638; all of which were filed June 4, 2024. U.S. Provisional Patent Application No.63 / 655,635; U.S. Provisional Patent Application No. 63 / 655,636; and U.S. Provisional Patent Application No.63 / 655,638 are hereby incorporated by reference. FIELD

[0002] An aldehyde – amine curable polyorganosiloxane composition and method for its preparation are provided. More particularly, the composition includes a monoamine-functional organosilicon compound and an aldehyde-functional organosilicon compound. INTRODUCTION

[0003] Room temperature vulcanizing (RTV) silicone compositions are useful in a myriad of applications, such as mold making, preparing adhesives, sealants, or elastomers, and forming gaskets (formed in place). RTV silicone compositions are known in the art and can be prepared from one-part compositions, or two-part (base and curing agent) compositions, where the two parts are mixed before use. Typically, RTV silicone compositions contain condensation reaction catalysts, such as dibutyl tin dilaurate, that catalyze condensation reaction cure of the RTV silicone composition. There is an ongoing need in the silicones industry to provide RTV silicone compositions that are free of organotin compounds.

[0004] Catalyst free silicone sealants that cure underwater have been disclosed. Aqueous solutions of glutaraldehyde, glyoxal or formaldehyde react without catalysts with a variety of aminopropyl modified silicone polymers to give silicone elastomers, even underwater. However, these sealants may suffer from the drawbacks of including toxic, volatile aldehydes, which are not compatible with the aminopropyl modified silicone polymers. SUMMARY

[0005] A curable polyorganosiloxane composition comprises: (A) a monoamine-functional organosilicon, and (B) an aldehyde-functional organosilicon compound. Methods for preparation and use of this composition are provided. DETAILED DESCRIPTION

[0006] The curable polyorganosiloxane composition (composition) introduced above comprises a cure package. The cure package comprises, alternatively consists essentially of,alternatively consists of (A) the monoamine-functional organosilicon compound and (B) the aldehyde-functional organosilicon compound. At least one of starting material (A) and starting material (B) may be a polyorganosiloxane. Without wishing to be bound by theory, it is thought that the composition can cure sufficiently even without the presence of a conventional bis- hydroxyl-terminated polydiorganosiloxane. Furthermore, it is thought that the reaction of the amino moiety from starting material (A) and the aldehyde moiety from starting material (B) will generate water as a side product, which can enhance cure, particularly deep section cure of the composition, particularly when starting material (A), or starting material (B), or an additional starting material (when present), includes a hydrolyzable moiety (such as an alkoxy group). (A) Monoamine-Functional Organosilicon Compound

[0007] Starting material (A) in the composition is the monoamine-functional organosilicon compound. The monoamine-functional organosilicon compound has, per molecule, at least one monoamino-functional group. Alternatively, the monoamine-functional organosilicon compound may have per molecule, more than one monoamino-functional group, alternatively at least two monoamino-functional groups per molecule. The monoamino-functional group may have formula: -G’-NH2, where G’ is a divalent hydrocarbon group free of aliphatic unsaturation that has 2 to 8 carbon atoms. The divalent hydrocarbyl groups may be free of aliphatic unsaturation. The divalent hydrocarbyl groups may have 1 to 8 carbon atoms. The divalent hydrocarbyl groups may be linear or branched. Examples of divalent hydrocarbyl groups for G’ include alkane-diyl groups of empirical formula -CrH2r-, where subscript r is 1 to 8. The alkane- diyl group may be a linear alkane-diyl, e.g., -CH2-CH2-, -CH2-CH2-CH2-, -CH2-CH2-CH2-CH2-,or -CH2-CH2-CH2-CH2-CH2-CH2-, or a branched alkane-. Alternatively, each G’ may be an alkane-diyl group of4 carbon atoms. Alternatively, suitable monoamine- functional groups bonded to silicon atoms in starting material (A) include aminoethyl, aminopropyl, aminobutyl (including linear and branched isomers, such as aminoisobutyl).

[0008] Starting material (A) may be one monoamino-functional organosilicon compound. Alternatively, two or more monoamino-functional organosilicon compounds that differ from oneanother may be used herein. For example, the monoamino-functional organosilicon compound may comprise one or both of (A-1) a monoamino-functional silane and (A-2) a monoamino- functional polyorganosiloxane.

[0009] The monoamino-functional organosilicon compound may comprise a monoamino- functional silane of formula as described above, subscript y is an integer selected monovalenthydrocarbyl group, and - y may be 0. R2may be an alkyl group with 1 to 18 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl (including n-propyl and isopropyl), butyl (including n-butyl, isobutyl, sec-butyl and tert- butyl), and branched and linear saturated hydrocarbyl groups of 5 to 18 carbon atoms. Alternatively R2may be selected from methyl, ethyl, propyl or butyl; alternatively methyl or ethyl. Examples of monoamino-functional trialkoxysilanes suitable for use as starting material (A1-1) include 3-aminopropyltriethoxysilane (CAS No.919-30-2); 3- aminopropyltrimethoxysilane (CAS No.13822-56-5); 2-aminoethyltriethoxysilane; 2- aminoethyltrimethoxysilane; 4-aminobutyltriethoxysilane (CAS No.3069-30-5); 4-aminoethyl- 3,3-dimethylbutyltrimethoxysilane (CAS No.157923-74-5); aminoisobutyltriethoxysilane; and aminoisobutyltrimethoxysilane. Examples of monoamino-functional dialkoxysilanes suitable for use as starting material (A1-1) include 3-aminopropyl, methyl, diethoxysilane (CAS No. 3179-76-8). Monoamino-functional alkoxysilanes are known in the art and are commercially available. For example, 3-aminopropyltriethoxysilane is available as DOWSIL™ Z-6011 Silane; 3-aminopropyl, methyl, diethoxysilane is available as DOWSIL™ Z-6015 Silane, and each is available from The Dow Chemical Company of Midland, Michigan, USA. In addition, 3-aminopropyltriethoxysilane; 3-aminopropyltrimethoxysilane; 4-aminobutyltriethoxysilane; and 4-aminoethyl)-3,3-dimethylbutyltrimethoxysilane are available from Gelest, Inc. of Morrisville, Pennsylvania, USA.

[0010] Alternatively, (A) the monoamine-functional organosilicon compound may comprise (A-2) a monoamino-functional polyorganosiloxane. The monoamino-functional polyorganosiloxane may be cyclic, linear, branched, resinous, or a combination of two or more thereof. Alternatively, the monoamino-functional polyorganosiloxane may be linear, branched, or resinous; alternatively linear or resinous. The monoamino-functional polyorganosiloxane may have at least 1, alternatively at least 2, and alternatively at least 3 monoamino-functional groups per molecule. Said monoamino-functional polyorganosiloxane may comprise unitformula (A2-1): (R23SiO1 / 2)a(R22RNHSiO1 / 2)b(R22SiO2 / 2)c(R2RNHSiO2 / 2)d(R2SiO3 / 2)e(RNHSiO3 / 2)f(SiO4 / 2)g(ZO1 / 2)h; wherein R2is as described above, each RNHis the monoamino-functional group of formula -G’- NH2, wherein G’ is the divalent hydrocarbon group free of aliphatic unsaturation that has 2 to 8 carbon atoms, as described above, and each Z is independently selected from the group consisting of a hydrogen atom and R5, wherein each R5is independently selected from the group consisting of alkyl groups of 1 to 18 carbon atoms and aryl groups of 6 to 18 carbon atoms. Subscripts a, b, c, d, e, f, and g represent average numbers, per molecule, of each siloxy unit in the unit formula. Subscript h represents an average number of hydrolyzable groups per molecule. Subscripts a, b, c, d, e, f, g, and h and have values such that subscript a ≥ 0, subscript b ≥ 0, subscript c ≥ 0, subscript d ≥ 0, subscript e ≥ 0, subscript f ≥ 0, subscript g ≥ 0, and subscript h ≥ 0; and subscript h has a value such that 0 ≤ h / (e + f + g) ≤ 1.5. Furthermore, the subscripts have values such that 10,000 ≥ (a + b + c + d + e + f + g) ≥ 2, and a quantity (b + d + f) ≥ 1, alternatively (b + d + f) ≥ 2, and alternatively (b + d + f) ≥ 3. Alternatively, each R2may be independently selected from the group consisting of an alkyl group of 1 to 18 carbon atoms and an aryl group of 6 to 18 carbon atoms. Alternatively, each Z is independently selected from the group consisting of a hydrogen atom and R5, where each R5is independently selected from the group consisting of alkyl groups of 1 to 18 carbon atoms and aryl groups of 6 to 18 carbon atoms. Alternatively, each Z may be hydrogen or an alkyl group of 1 to 6 carbon atoms. Alternatively, each Z may be hydrogen.

[0011] Alternatively, (A-2) the monoamino-functional polyorganosiloxane may comprise (A2- 2) a linear polydiorganosiloxane having, per molecule, at least one monoamino-functional group, alternatively at least two monoamino-functional groups (e.g., when in the formula (A2-1) above, subscripts e = f = g = 0). For example, said polydiorganosiloxane may comprise unit formula (A2-2): (R23SiO1 / 2)a(RNHR22SiO1 / 2)b(R22SiO2 / 2)c(RNHR2SiO2 / 2)d(ZO1 / 2)h, wherein RNHand R2are as described above, subscript a is 0, 1, or 2; subscript b is 0, 1, or 2; subscript h is 0, 1, or 2; subscript c ≥ 0, subscript d ≥ 0, with the provisos that a quantity (b + d) ≥ 1, a quantity (a + b + h) = 2, and a quantity (a + b + c + d) ≥ 2. Alternatively, in the unit formula (A2-2) for the linear monoamino-functional polydiorganosiloxane, above, the quantity (a + b + c + d) may be at least 3, alternatively at least 4, and alternatively > 50. At the same time said formula, the quantity (a + b + c + d) may be less than or equal to 10,000; alternatively less than or equal to 4,000; alternatively less than or equal to 2,000; alternatively less than or equal to 1,000; alternatively less than or equal to 500; alternatively less than or equal to 250. Alternatively, subscript c ≥ 0, subscript d ≥ 0, with the provisos that a quantity (b + d) ≥ 1, and a quantity 1 ≤ (c + d) ≤ 180. Alternatively, in the unit formula for the linear monoamino-functional polyorganosiloxane, eachR2may be independently selected from the group consisting of alkyl and aryl; alternatively methyl and phenyl. Alternatively, each R2in said formula may be an alkyl group; alternatively each R2may be methyl.

[0012] Starting material (A2-2), the linear monoamino-functional polydiorganosiloxane, may comprise a monoamino-functional polydiorganosiloxane such as: i) bis(trimethylsiloxy- terminated) poly(dimethyl / 3-aminopropyl,methyl)siloxane with CAS# 99363-37-8, which is commercially available as DOWSIL™ AP 3651 Fluid; ii) poly(dimethyl / aminopropyl,methyl)siloxane copolymer end capped with methoxy and silanol end groups; iii) bis(3-aminopropyl,dimethylsiloxy-terminated) polydimethylsiloxane; and iv) poly(dimethyl / aminopropyl,methyl)siloxane copolymer end capped with trimethylsiloxy units. These and other monoamine-functional organosilicon compounds are known in the art and may be made by known methods, such as those disclosed in US Patents 7238768, 11028229, and 11028233. Other monoamino-functional polydiorganosiloxanes are commercially available, for example, DMS-A21 (bis-aminopropyl-terminated polydimethylsiloxane with viscosity 100 – 120 cSt CAS No.106214-84-0), DMS-A31 (bis-aminopropyl-terminated polydimethylsiloxane with viscosity 900 – 1,100 cSt CAS No.106214-84-0), AMS-191 (poly(dimethyl / aminopropyl,methyl)siloxane copolymer end capped with dimethylsiloxy groups, and with viscosity 40-60 cSt, CAS No.99363-37-8), and AMS-163 (poly(dimethyl / aminopropyl,methyl)siloxane copolymer endcapped with dimethylsiloxy groups and with viscosity 1,800 to 2,200 cSt, CAS No.99363-37-8) are commercially available from Gelest.

[0013] Alternatively, (A2) the monoamino-functional polyorganosiloxane may be oligomeric, e.g., when in unit formula (A2-1) above the quantity (a + b + c + d + e + f + g) ≤ 50, alternatively ≤ 40, alternatively ≤ 30, alternatively ≤ 25, alternatively ≤ 20, alternatively ≤ 10, alternatively ≤ 5, alternatively ≤ 4, alternatively ≤ 3. Examples of linear monoamino-functional polyorganosiloxane oligomers may have formula (A2-3): , where R4is as described above, each R3’isof R4and RNH, with the proviso that at least one R3’, per molecule, is RNH, and subscript Z is 0 to 48. Examples of linear monoamino- functional polyorganosiloxane oligomers include 1,3-di(propyl-amino)-1,1,3,3- tetramethyldisiloxane; 1,1,1,3,3-pentamethyl-3-(propylamino)-disiloxane; and 1,1,1,3,5,5,5-heptamethyl-3-(propylamino)-trisiloxane.

[0014] Alternatively, starting material (A-2) may comprise (A2-4) a monoamino-functional polyorganosiloxane resin, such as a monoamino-functional polyorganosilicate resin and / or an monoamino-functional silsesquioxane resin. The monoamino-functional polyorganosilicate resin comprises monofunctional units (M” units) of formula RM”3SiO1 / 2 and tetrafunctional silicate units (Q units) of formula SiO4 / 2, where each RM”may be independently selected from the group consisting of R4and RNHas described above. Alternatively, each RM”may be selected from the group consisting of an alkyl group, a monoamino-functional group of the formula shown above, and an aryl group. Alternatively, each RM”may be selected from methyl, 3- aminopropyl, 2-aminoethyl, 4-aminobutyl, aminoisobutyl, and phenyl. Alternatively, at least one-third, alternatively at least two thirds of the RM”groups are methyl groups. Alternatively, the M” units may be exemplified by (Me3SiO1 / 2), (Me2PhSiO1 / 2), and (Me2RNHSiO1 / 2). The polyorganosilicate resin is soluble in solvents exemplified by liquid hydrocarbons, such as benzene, ethylbenzene, toluene, xylene, and heptane, or in liquid non-functional organosilicon compounds such as low viscosity linear and cyclic polydiorganosiloxanes.

[0015] When prepared, the polyorganosilicate resin comprises the M” and Q units described above, and the polyorganosiloxane further comprises units with silicon bonded hydroxyl groups, and / or hydrolyzable groups, described by moiety (ZO1 / 2), above, and may comprise neopentamer of formula Si(OSiRM”3)4, where RM”is as described above, e.g., the neopentamer may be tetrakis(trimethylsiloxy)silane.29Si NMR and13C NMR spectroscopies may be used to measure hydroxyl and alkoxy content and molar ratio of M” and Q units, where said ratio is expressed as {M”(resin)} / {Q(resin)}, excluding M” and Q units from the neopentamer. M” / Q ratio represents the molar ratio of the total number of triorganosiloxy groups (M” units) of the resinous portion of the monoamino-functional polyorganosilicate resin to the total number of silicate groups (Q units) in the resinous portion. M” / Q ratio may be 0.5 / 1 to 1.5 / 1, alternatively 0.6 / 1 to 0.9 / 1.

[0016] The Mn and Mw of the monoamino-functional polyorganosilicate resin depends on various factors including the types of groups represented by RM”that are present. The Mn of the polyorganosilicate resin refers to the number average molecular weight measured using GPC, when the peak representing the neopentamer is excluded from the measurement. The Mn of the polyorganosilicate resin may be 1,500 Da to 30,000 Da, alternatively 1,500 Da to 15,000 Da; alternatively 3,000 Da to 8,000 Da. Alternatively, Mn of the polyorganosilicate resin may be 3,000 Da to 4,000 Da. The Mw of the monoamino-functional polyorganosilicate resin may also be measured by GPC, and may be 3,000 Da to 30,000 Da, alternatively 4,000 Da to 12,000 Da, alternatively 5,000 Da to 10,000 Da, and alternatively 5,500 Da to 6,500 Da.

[0017] Alternatively, the polyorganosilicate resin may comprise unit formula (A2-5): (R43SiO1 / 2)mm(R42RNHSiO1 / 2)nn(SiO4 / 2)oo(ZO1 / 2)h, where Z, R4, and RNH, and subscript h are as described above and subscripts mm, nn and oo have average values such that mm ≥ 0, nn > 0, oo > 0, and 0.5 < (mm + nn) / oo < 4. Alternatively, 0.6 < (mm + nn) / oo < 4; alternatively 0.7 < (mm + nn) / oo < 4, and alternatively 0.8 < (mm + nn) / oo < 4.

[0018] Alternatively, (A-2) the monoamino-functional polyorganosiloxane may comprise (A2- 6) a monoamino-functional silsesquioxane resin, i.e., a resin containing trifunctional (T”) units of unit formula (A2-7): (R43SiO1 / 2)a(R42RNHSiO1 / 2)b(R42SiO2 / 2)c(R4RNHSiO2 / 2)d(R4SiO3 / 2)e(RNHSiO3 / 2)f(ZO1 / 2)h; where R4and RNHare as described above, subscript f > 1, 2 < (e + f) < 10,000; 0 < (a + b) / (e + f) < 3; 0 < (c + d) / (e + f) < 3; and 0 < h / (e + f) < 1.5. Alternatively, the monoamino-functional silsesquioxane resin may comprise unit formula (A2-8): (R4SiO3 / 2)e(RNHSiO3 / 2)f(ZO1 / 2)h, where R4, RNH, Z, and subscripts h, e and f are as described above. Alternatively, the monoamino- functional silsesquioxane resin may further comprise monofunctional (M”) units of formulae (R43SiO1 / 2)a(R42RNHSiO1 / 2)b, i.e., an M”D”T” resin, where subscripts a and b are as described above for unit formula (A2-1).

[0019] Alternatively, the monoamino-functional polyorganosiloxane resins described above may further comprise difunctional (D”) units of formulae (R42SiO2 / 2)c(R4RNHSiO2 / 2)d in addition to the units described above, e.g., said resin may be a M”D”Q” resin or D”T” resin, where subscripts c and d are as described above.

[0020] The monoamino-functional polyorganosiloxane resin may be prepared by known methods, such as those disclosed in US Patent 8722148, US Patent 7501473, and US Patent Application Publication 20060205861. Alternatively, the mono-amino-functional polyorganosiloxane may be commercially available. For example, DOWSIL™ 2-2078 Fluid contains an aminopropyl-, phenyl silsesquioxane, trimethylsiloxy-terminated resin with CAS No.717908-03-7. (B) Aldehyde-Functional Organosilicon Compound

[0021] Starting material (B) in the composition is an aldehyde-functional organosilicon compound. The aldehyde-functional organosilicon compound has, per molecule, at least one aldehyde-functional group covalently bonded to silicon. Alternatively, the aldehyde-functional organosilicon compound may have, per molecule, more than one aldehyde-functional group covalently bonded to silicon, alternatively at least two aldehyde-functional groups per molecule, and alternatively at least aldehyde-functional groups per molecule. The aldehyde-functionalgroup covalently bonded to silicon may have formula s a divalent hydrocarbon group free of aliphatic unsaturation that ay be linear or branched. Examples of divalent hydrocarbyl groups for G include alkane-diyl groups of empirical formula -CrH2r-, where subscript r is 2 to 8. The alkane-diyl group may be a linear alkane-diyl, e.g., -CH2-CH2-, -CH2-CH2-CH2-, -CH2-CH2-CH2-CH2-, or -CH2-CH2-CH2-CH2-CH2-CH2-, or a branched alkane- or. Alternatively, each G may be an alkane-diyl group of 2 to 6 carbon atoms;2, 3, or 6 carbon atoms. The aldehyde-functional organosilicon compound may be one aldehyde-functional organosilicon compound. Alternatively, two or more aldehyde- functional organosilicon compounds that differ from one another may be used in the process described herein. For example, the aldehyde-functional organosilicon compound may comprise one or both of an aldehyde-functional silane and an aldehyde-functional polyorganosiloxane.

[0022] The aldehyde-functional organosilicon compound may comprise (B1) an aldehyde- functional silane of formula (B1-1): RAldxSiR4(4-x), where each RAldis an independently selected group of the described above; and each R4is independently selected from thegroup of 1 to 18 carbon atoms, an aryl group of 6 to 18 carbon atoms, an acyloxy group of 2 to 18 carbon atoms, and a hydrocarbonoxy-functional group of 1 to 18 carbon atoms; and subscript x is 1 to 4. Alternatively, subscript x may be 1 or 2, alternatively 2, and alternatively 1. Alternatively, each R4may be independently selected from the group consisting of an alkyl group of 1 to 18 carbon atoms, an aryl group of 6 to 18 carbon atoms, and an alkoxy-functional group of 1 to 18 carbon atoms. Alternatively, in formula (B1-1) each R4may be an alkoxy-functional group of 1 to 18 carbon atoms or an acyloxy group of 2 to 18 carbon atoms; alternatively, methoxy, ethoxy, or acetoxy. Alternatively, in formula (B1-1), when subscript x = 1, at least one instance of R4may be a hydrocarbonoxy group or an acyloxygroup, alternatively at least two instances of R4, and alternatively 2 instances of R4.

[0023] Suitable aldehyde-functional silanes are exemplified by aldehyde-functional trialkoxysilanes such as (butyl-aldehyde)trimethoxysilane, (propyl-aldehyde)-trimethoxysilane, (propyl-aldehyde)-triethoxysilane, (propyl-aldehyde)-triisopropoxysilane, and (propyl- aldehyde)-tris(methoxyethoxy)silane; aldehyde-functional dialkoxysilanes such as (propyl- aldehyde)-phenyldiethoxysilane, (propyl-aldehyde)-methyldimethoxysilane, and (propyl- aldehyde)-methyldiethoxysilane; aldehyde-functional monoalkoxysilanes such as tri(propyl- aldehyde)-methoxysilane; aldehyde-functional triacyloxysilanes such as (propyl-aldehyde)- triacetoxysilane, and aldehyde-functional diacyloxysilanes such as (propyl-aldehyde)- methyldiacetoxysilane.

[0024] Alternatively, the aldehyde-functional organosilicon compound may comprise (B2) an aldehyde-functional polyorganosiloxane. Said aldehyde-functional polyorganosiloxane may be cyclic, linear, branched, resinous, or a combination of two or more thereof. Said aldehyde- functional polyorganosiloxane may have at least 1, alternatively at least 2, and alternatively at least 3 aldehyde groups per molecule. Said aldehyde-functional polyorganosiloxane may comprise unit formula (B2-1): (R43SiO1 / 2)a(R42RAldSiO1 / 2)b(R42SiO2 / 2)c(R4RAldSiO2 / 2)d(R4SiO3 / 2)e(RAldSiO3 / 2)f(SiO4 / 2)g(ZO1 / 2)h; where each RAldis an independently selected aldehyde group of the , where G is as described above, and R4, Z, and subscripts a, b, c, d, e, f, g,above. Alternatively, each R4may be independently selected from the group consisting of an alkyl group of 1 to 18 carbon atoms, an aryl group of 6 to 18 carbon atoms, and a hydrocarbonoxy group of 1 to 18 carbon atoms. Alternatively, in formula (B2-1) each R4may be independently selected from the group consisting of an alkyl group of 1 to 18 carbon atoms and an aryl group of 6 to 18 carbon atoms. Each Z is independently selected from the group consisting of a hydrogen atom and R5, where each R5is independently selected from the group consisting of alkyl groups of 1 to 18 carbon atoms and aryl groups of 6 to 18 carbon atoms. Subscripts a, b, c, d, e, f, and g represent average numbers, per molecule, of each siloxy unit in the unit formula. Subscript h represents an average number of hydrolyzable groups per molecule. Subscripts a, b, c, d, e, f, g, and h and have values such that subscript a ≥ 0, subscript b ≥ 0, subscript c ≥ 0, subscript d ≥ 0, subscript e ≥ 0, subscript f ≥ 0, subscript g ≥ 0, and subscript h ≥ 0; and subscript h has a value such that 0 ≤ h / (e + f + g) ≤ 1.5, 10,000 ≥ (a + b + c + d + e + f + g) ≥ 2, and a quantity (b + d + f) ≥ 1. At the same time, the quantity (a + b + c + d + e + f + g) may be ≤ 10,000. Alternatively, in the unit formula (B2-1) for the aldehyde-functional polyorganosiloxane, each R4may be independently selected from the group consisting of an alkyl group of 1 to 18 carbon atoms, an aryl group of 6 to 18 carbon atoms, and a hydrocarbonoxy-functional group of 1 to 18 carbon atoms. Alternatively, in the unit formula (B2-1) each R4may be independently selected from the group consisting of an alkyl group of 1 to 18 carbon atoms, an aryl group of 6 to 18 carbon atoms, and an alkoxy-functional group of 1 to 18 carbon atoms. Alternatively, in the unit formula (B2-1) each R4may be independently selected from the group consisting of an alkyl group of 1 to 18 carbon atoms and an aryl group of 6 to 18 carbon atoms. Alternatively, in the unit formula (B2-1) each Z may be hydrogen or an alkyl group of 1 to 6 carbon atoms. Alternatively, each Z may be hydrogen.

[0025] Alternatively, (B2) the aldehyde-functional polyorganosiloxane may comprise (B2-2) a linear polydiorganosiloxane having, per molecule, at least one aldehyde-functional group; alternatively at least two aldehyde-functional groups (e.g., when in the formula (B2-1) for the aldehyde-functional polyorganosiloxane above, subscripts e = f = g = 0). For example, said polydiorganosiloxane may comprise unit formula (B2-3): (R43SiO1 / 2)a(RAldR42SiO1 / 2)b(R42SiO2 / 2)c(RAldR4SiO2 / 2)d, where RAldand R4are as described above, subscript a is 0, 1, or 2; subscript b is 0, 1, or 2, subscript c ≥ 0, subscript d ≥ 0, with the provisos that a quantity (b + d) ≥ 1, a quantity (a + b) = 2, and a quantity (a + b + c + d) ≥ 2. Alternatively, in the unit formula (B2-3) for the linear aldehyde-functional polyorganosiloxane, above, the quantity (a + b + c + d) may be at least 3, alternatively at least 4, and alternatively > 50. At the same time said formula, the quantity (a + b + c + d) may be less than or equal to 10,000; alternatively less than or equal to 4,000; alternatively less than or equal to 2,000; alternatively less than or equal to 1,000; alternatively less than or equal to 500; alternatively less than or equal to 250. Alternatively, subscript c ≥ 0, subscript d ≥ 0, with the provisos that a quantity (b + d) ≥ 1, and a quantity 1 ≤ (c + d) ≤ 180. Alternatively, in the unit formula for the linear aldehyde-functional polyorganosiloxane, each R4may be independently selected from the group consisting of alkyl and aryl; alternatively methyl and phenyl. Alternatively, each R4in said formula may be an alkyl group; alternatively each R4may be methyl.

[0026] Starting material (B2) may comprise an aldehyde-functional polydiorganosiloxane such as i) bis-dimethyl(propyl-aldehyde)siloxy-terminated polydimethylsiloxane, ii) bis- dimethyl(propyl-aldehyde)siloxy-terminated poly(dimethylsiloxane / methyl(propyl- aldehyde)siloxane), iii) bis-dimethyl(propyl-aldehyde)siloxy-terminated polymethyl(propyl- aldehyde)siloxane, iv) bis-trimethylsiloxy-terminated poly(dimethylsiloxane / methyl(propyl- aldehyde)siloxane), v) bis-trimethylsiloxy-terminated polymethyl(propyl-aldehyde)siloxane, vi) bis-dimethyl(propyl-aldehyde)siloxy-terminated poly(dimethylsiloxane / methylphenylsiloxane / methyl(propyl-aldehyde)siloxane), vii) bis-dimethyl(propyl-aldehyde)siloxy-terminated poly(dimethylsiloxane / methylphenylsiloxane), viii) bis-dimethyl(propyl-aldehyde)siloxy-terminated poly(dimethylsiloxane / diphenylsiloxane), ix) bis-phenyl,methyl,(propyl-aldehyde)-siloxy-terminated polydimethylsiloxane, x) bis- dimethyl(heptyl-aldehyde)siloxy-terminated polydimethylsiloxane, xi) bis-dimethyl(heptyl- aldehyde)siloxy-terminated poly(dimethylsiloxane / methyl(heptyl-aldehyde)siloxane), xii) bis- dimethyl(heptyl-aldehyde)siloxy-terminated polymethyl(heptyl-aldehyde)siloxane, xiii) bis- trimethylsiloxy-terminated poly(dimethylsiloxane / methyl(heptyl-aldehyde)siloxane), xiv) bis- trimethylsiloxy-terminated polymethyl(heptyl-aldehyde)siloxane, xv) bis-dimethyl(heptyl- aldehyde)-siloxy terminated poly(dimethylsiloxane / methylphenylsiloxane / methyl(heptyl- aldehyde)siloxane), xvi) bis-dimethyl(propyl-aldehyde)siloxy-terminated poly(dimethylsiloxane / methyl(heptyl-aldehyde)siloxane), xvii) bis-dimethyl(heptyl-aldehyde)- siloxy-terminated poly(dimethylsiloxane / methylphenylsiloxane), xviii) dimethyl(heptyl- aldehyde)-siloxy-terminated poly(dimethylsiloxane / diphenylsiloxane), and xix) a combination of two or more of i) to xviii).

[0027] Alternatively, (B2) the aldehyde-functional polyorganosiloxane may be oligomeric, e.g., when in unit formula (B2-1) above the quantity (a + b + c + d + e + f + g) ≤ 50, alternatively ≤ 40, alternatively ≤ 30, alternatively ≤ 25, alternatively ≤ 20, alternatively ≤ 10, alternatively ≤ 5, alternatively ≤ 4, alternatively ≤ 3. Examples of linear aldehyde-functional polyorganosiloxane oligomers may have formula (B2-4): , where R4is as described above, each R3isconsisting of R4and RAld, with the proviso that at least one R3, per molecule, is RAld, and subscript z is 0 to 48. Examples of linear aldehyde-functional polyorganosiloxane oligomers include 1,3-di(propyl-aldehyde)-1,1,3,3-tetramethyldisiloxane; 1,1,1,3,3-pentamethyl-3-(propyl-aldehyde)-disiloxane; and 1,1,1,3,5,5,5-heptamethyl-3-(propyl- aldehyde)-trisiloxane.

[0028] Alternatively, (B2) the aldehyde-functional polyorganosiloxane may comprise an aldehyde-functional polyorganosiloxane resin, such as an aldehyde-functional polyorganosilicate resin and / or an aldehyde-functional silsesquioxane resin. Such resins may be prepared, for example, by hydroformylating an alkenyl-functional polyorganosiloxane resin. The aldehyde- functional polyorganosilicate resin comprises monofunctional units (M’ units) of formula RM’3SiO1 / 2and tetrafunctional silicate units (Q units) of formula SiO4 / 2, where each RM’may beindependently selected from the group consisting of R4and RAldas described above. Alternatively, each RM’may be selected from the group consisting of an alkyl group, an aldehyde-functional group of the formula shown above, and an aryl group. Alternatively, each RM’may be selected from methyl, (propyl-aldehyde) and phenyl. Alternatively, at least one- third, alternatively at least two thirds of the RM’groups are methyl groups. Alternatively, the M’ units may be exemplified by (Me3SiO1 / 2), (Me2PhSiO1 / 2), and (Me2RAldSiO1 / 2). The polyorganosilicate resin is soluble in solvents exemplified by liquid hydrocarbons, such as benzene, ethylbenzene, toluene, xylene, and heptane, or in liquid non-functional organosilicon compounds such as low viscosity linear and cyclic polydiorganosiloxanes.

[0029] When prepared, the polyorganosilicate resin comprises the M’ and Q units described above, and the polyorganosiloxane further comprises units with silicon bonded hydroxyl groups, and / or hydrolyzable groups, described by moiety (ZO1 / 2), above, and may comprise neopentamer of formula Si(OSiRM’3)4, where RM’is as described above, e.g., the neopentamer may be tetrakis(trimethylsiloxy)silane.29Si NMR and13C NMR spectroscopies may be used to measure hydroxyl and alkoxy content and molar ratio of M’ and Q units, where said ratio is expressed as {M’(resin)} / {Q(resin)}, excluding M’ and Q units from the neopentamer. M’ / Q ratio represents the molar ratio of the total number of triorganosiloxy groups (M’ units) of the resinous portion of the polyorganosilicate resin to the total number of silicate groups (Q units) in the resinous portion. M’ / Q ratio may be 0.5 / 1 to 1.5 / 1, alternatively 0.6 / 1 to 0.9 / 1.

[0030] The Mn of the polyorganosilicate resin depends on various factors including the types of hydrocarbon groups represented by RM’that are present. The Mn of the polyorganosilicate resin refers to the number average molecular weight measured using GPC, when the peak representing the neopentamer is excluded from the measurement. The Mn of the polyorganosilicate resin may be 1,500 Da to 30,000 Da, alternatively 1,500 Da to 15,000 Da; alternatively >3,000 Da to 8,000 Da. Alternatively, Mn of the polyorganosilicate resin may be 3,500 Da to 8,000 Da. The Mw of the aldehyde-functional polyorganosilicate resin may also be measured by GPC, and may be 3,000 Da to 30,000 Da, alternatively 4,000 Da to 12,000 Da, alternatively 5,000 Da to 10,000 Da, and alternatively 5,500 Da to 6,500 Da.

[0031] Alternatively, the aldehyde-functional polyorganosilicate resin may comprise unit formula (B2-5): (R43SiO1 / 2)mm(R42RAldSiO1 / 2)nn(SiO4 / 2)oo(ZO1 / 2)h, where Z, R4, and RAld, and subscript h are as described above and subscripts mm, nn and oo have average values such that mm ≥ 0, nn > 0, oo > 0, and 0.5 < (mm + nn) / oo < 4. Alternatively, 0.6 < (mm + nn) / oo < 4; alternatively 0.7 < (mm + nn) / oo < 4, and alternatively 0.8 < (mm + nn) / oo < 4.

[0032] Alternatively, (B2) the aldehyde-functional polyorganosiloxane may comprise (B2-6) an aldehyde-functional silsesquioxane resin, i.e., a resin containing trifunctional (T’) units ofunit formula (B2-7): (R43SiO1 / 2)a(R42RAldSiO1 / 2)b(R42SiO2 / 2)c(R4RAldSiO2 / 2)d(R4SiO3 / 2)e(RAldSiO3 / 2)f(ZO1 / 2)h; where R4and RAldare as described above, subscript f > 1, 2 < (e + f) < 10,000; 0 < (a + b) / (e + f) < 3; 0 < (c + d) / (e + f) < 3; and 0 < h / (e + f) < 1.5. Alternatively, the aldehyde-functional silsesquioxane resin may comprise unit formula (B2-8): (R4SiO3 / 2)e(RAldSiO3 / 2)f(ZO1 / 2)h, where R4, RAld, Z, and subscripts h, e and f are as described above. Alternatively, the aldehyde-functional silsesquioxane resin may further comprise difunctional (D’) units of formulae (R42SiO2 / 2)c(R4RAldSiO2 / 2)din addition to the T units described above, i.e., a D’T’ resin, where subscripts c and d are as described above. Alternatively, the aldehyde-functional silsesquioxane resin may further comprise monofunctional (M’) units of formulae (R43SiO1 / 2)a(R42RAldSiO1 / 2)b, i.e., an M’D’T’ resin, where subscripts a and b are as described above for unit formula (B2-1).

[0033] Suitable aldehyde-functional organosilicon compounds are known in the art and may be prepared by known methods, such as those described in US Patent 4424392 to Petty; US Patent 5021601 to Frances et al.; US Patent 5739246 to Graiver et al.; US Patent 7696294 to Asirvatham; and US Patent 7999053 to Sutton et al.; European Patent Application Publication EP 0392948 A1 to Frances, US Patent Application Publication 20230242711 to Fisk et al., and PCT Patent Application Publications WO2006027074 to Kühnle et al., WO2023200934 to Tulchinsky et al., and WO2023091868 to Han et al. PCT Publications WO2023200934 and WO2023091868 and US Patent Application Publication 20230242711 are hereby incorporated by reference.

[0034] The amounts of (A) the monoamino-functional organosilicon compound and (B) the aldehyde-functional organosilicon compound used in the composition depend on various factors including the types and amounts of starting materials (A) and (B), whether starting material (A) and / or starting material (B) has other curable groups (e.g., alkoxy groups), the type and amount of any additional starting materials (such as the drying agent and / or the catalyst described below) that may be added to the composition and the desired properties and end use of the cured product of the composition. However, the amounts of (A) the monoamino-functional organosilicon compound and (B) the aldehyde-functional organosilicon compound may be sufficient to provide a molar ratio of reactive amine moieties from starting material (A) to aldehyde moieties of starting material (B) (NH2 / CHO ratio) of 0.09 / 1 to 31 / 1. Without wishing to be bound by theory, it is thought that a composition comprising starting materials (A) and (B) will cure when the NH2 / CHO ratio is in this range, particularly when a condensation reaction catalyst is added. Alternatively, for an uncatalyzed composition (i.e., composition comprising starting materials (A) and (B) but free of the condensation reaction catalyst described below for starting material (R)), then the NH2 / CHO ratio may be 0.24 / 1 to 1.70 / 1 to obtain a compositionthat will cure in a desired time frame, e.g., 4 days or less. One skilled in the art would be able to select a NH2 / CHO ratio based on various factors including the desired time frame for cure and the selection of the various optional additional starting materials that may be added to the composition. Alternatively, NH2 / CHO ratio may be at least 0.24 / 1, alternatively at least 0.28 / 1, alternatively at least 0.3 / 1, alternatively at least 0.4 / 1, alternatively at least 0.5 / 1, and alternatively at least 0.6 / 1; while at the same time, NH2 / CHO ratio may be up to 1.7 / 1, alternatively up to 1.4 / 1, alternatively up to 1.2 / 1, alternatively up to 1 / 1, alternatively up to 0.9 / 1, alternatively up to 0.8 / 1, and alternatively up to 0.7 / 1, regardless of the presence of condensation reaction catalyst. Alternatively, when the composition contains a catalyst, the NH2 / CHO ratio may be at least 0.09 / 1, alternatively at least 0.1 / 1, alternatively at least 0.2 / 1, alternatively at least 0.3 / 1, alternatively at least 0.4 / 1, alternatively at least 0.5 / 1, alternatively at least 0.6 / 1, alternatively at least 0.7 / 1, alternatively at least 0.8 / 1, alternatively at least 0.9 / 1, and alternatively at least 1 / 1; while at the same time, NH2 / CHO ratio may be up to 31 / 1, alternatively up to 30 / 1, alternatively up to 25 / 1, alternatively up to 20 / 1, alternatively up to 15 / 1, alternatively up to 10 / 1, and alternatively up to 5 / 1, and alternatively up to 1 / 1. The composition of this invention provides the benefit of having a time frame for cure that is customizable based on the selection and amounts of the starting materials in the composition. (C) Crosslinker

[0035] Starting material (C) is a crosslinker that may be added to the composition, for example, when to increase crosslink density of the reaction product prepared by curing the composition. Generally, starting material (C) is selected with functionality that can vary depending on the degree of crosslinking, modulus, or other properties desired in the reaction product of the composition. Generally, the selection of (C) the crosslinker is made such that the composition remains sufficiently reactive to be useful during storage for several months in a moisture impermeable package. Generally, (C) the crosslinker is selected such that the hydrolyzable substituents on starting material (C) are reactive with the substituents on starting materials (A), (B), or a reaction product thereof. For example, when starting material (A) is a monoamino-functional alkoxysilane or (a polyorganosiloxane that has hydrolyzable groups in addition to monoamino-functional groups) and / or starting material (B) is an aldehyde-functional alkoxysilane, then (C) the crosslinker may include a hydrolyzable substituent reactive with alkoxy groups, such as an alkoxy group. The exact amount of (C) the crosslinker can vary depending on factors including the type of (A) the monoamino-functional organosilicon compound and (B) the aldehyde-functional organosilicon compound selected and the desired crosslink density of the reaction product. However, the amount of crosslinker may range from 0.5 part to 100 parts based on 100 parts by weight of starting materials (A) and (B) combined.

[0036] Starting material (C) may comprise an alkoxysilane (that differs from starting materials (A) and (B)) and may be exemplified by a dialkoxysilane, such as a dialkyldialkoxysilane; a trialkoxysilane, such as an alkyltrialkoxysilane; a tetraalkoxysilane; or partial or full hydrolysis products thereof, or another combination thereof. Examples of suitable trialkoxysilanes include methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, isobutyltrimethoxysilane, isobutyltriethoxysilane, and a combination thereof, and alternatively methyltrimethoxysilane. Examples of suitable tetraalkoxysilanes include tetraethoxysilane. The amount of the alkoxysilane that is used in the curable silicone composition may range from 0.5 part to 15 parts by weight, per 100 parts by weight of starting material (B). (D) Drying agent

[0037] Starting material (D) is a drying agent that may optionally be added to the composition. The drying agent binds water from various sources. For example, the drying agent may bind by- products of the reaction between the amino-functional groups from starting material (A) and the aldehyde functional groups from starting material (B), where such by-products include water.

[0038] Examples of suitable adsorbents for starting material (D) may be inorganic particulates. The adsorbent may have a particle size of 10 micrometers or less, alternatively 5 micrometers or less. The adsorbent may have average pore size sufficient to adsorb water and alcohols, for example 10 Å (Angstroms) or less, alternatively 5 Å or less, and alternatively 3 Å or less. Examples of adsorbents include zeolites such as chabasite, mordenite, and analcite; molecular sieves such as alkali metal alumino silicates, silica gel, silica-magnesia gel, activated carbon, activated alumina, calcium oxide, and combinations thereof.

[0039] Examples of commercially available drying agents include dry molecular sieves, such as 3 Å (Angstrom) molecular sieves, which are commercially available from Grace Davidson under the trademark SYLOSIV™ and from Zeochem of Louisville, Kentucky, U.S.A. under the trade name PURMOL, and 4 Å molecular sieves such as Doucil zeolite 4A available from Ineos Silicas of Warrington, England. Other useful molecular sieves include MOLSIV ADSORBENT TYPE 13X, 3A, 4A, and 5A, all of which are commercially available from UOP of Illinois, U.S.A.; SILIPORITE NK 30AP and 65xP from Atofina of Philadelphia, Pennsylvania, U.S.A.; and molecular sieves available from W.R. Grace of Maryland, U.S.A.

[0040] Alternatively, the drying agent may bind the water by chemical means. An amount of a silane crosslinker added to the composition (in addition to starting material (C)) may function as a chemical drying agent. Without wishing to be bound by theory, it is thought that the chemical drying agent may be added to a one part composition, or to one or more parts of a multiple part composition, to keep the composition free from atmospheric moisture after the parts of the composition are mixed together. For example, alkoxysilanes suitable as drying agents includealkyltrialkoxysilanes such as methyltrimethoxysilane, methyltriethoxysilane, and a combination thereof; alkenyltrialkoxysilanes such as vinyltrimethoxysilane, vinyltriethoxysilane, and a combination thereof; cyanoalkyltrialkoxysilanes such as cyanoethyltrimethoxysilane, cyanoethyltriethoxysilane, and a combination thereof. Alternatively, starting material (D) may comprise the cyanoalkyltrialkoxysilane such as cyanoethyltrimethoxysilane, cyanoethyltriethoxysilane, or a combination thereof, particularly when the composition is formulated as a one-part composition. The amount of starting material (D) depends on the specific drying agent selected. However, when (D) is a chemical drying agent, the amount may range from 0 parts to 5 parts, alternatively 0.1 parts to 0.5 parts, per 100 parts by weight of the composition. (E) Extender

[0041] Starting material (E) is an extender and / or a plasticizer. An extender comprising a non- functional polyorganosiloxane may be used in the composition. Non-functional polyorganosiloxanes are known in the art and are commercially available. Suitable non- functional polyorganosiloxanes are exemplified by, but not limited to, polydimethylsiloxanes. Such polydimethylsiloxanes include DOWSIL™ 200 Fluids, which are commercially available from Dow Silicones Corporation of Midland, Michigan, U.S.A. and may have viscosity ranging from 50 cSt to 100,000 cSt, alternatively 50 cSt to 50,000 cSt, alternatively 100 cSt to 50,000 cSt, and alternatively 12,500 to 60,000 cSt at 25 °C.

[0042] An organic plasticizer may be used in addition to, or instead of, the non-functional polyorganosiloxane extender described above. Organic plasticizers are known in the art and are commercially available. The organic plasticizer may comprise a phthalate, a carboxylate, a carboxylic acid ester, an adipate or a combination thereof. Alternatively, a polymer plasticizer can be used. Examples of the polymer plasticizer include alkenyl polymers obtained by polymerizing vinyl or allyl monomers by means of various methods; polyalkylene glycol esters such as diethylene glycol dibenzoate, diethylene glycol dibenzoate and pentaerythritol ester; polyester plasticizers obtained from dibasic acids such as sebacic acid, adipic acid, azelaic acid and phthalic acid and dihydric alcohols such as ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol and dipropylene glycol; polyethers including polyether polyols each having a molecular weight of not less than 500 such as polyethylene glycol, polypropylene glycol and polytetramethylene glycol, polystyrenes such as polystyrene and poly-alpha- methylstyrene; and polybutadiene, polybutene, polyisobutylene, butadiene acrylonitrile, and polychloroprene.

[0043] When the organic plasticizer is present, the amount of the organic plasticizer may range from 5 parts to 150 parts by weight based on the combined weights of all starting materials inthe composition. The exact amount of starting material (E) used in the composition can depend on various factors including the desired end use of the composition and the cured product thereof. However, the amount of starting material (E) may range from 0.1 % to 10 % based on the combined weights of all starting materials in the composition. (F) Filler

[0044] Starting material (F) is a filler. The filler may comprise a reinforcing filler, an extending filler, a conductive filler, or a combination thereof. For example, the composition may optionally further comprise starting material (f1), a reinforcing filler, which when present may be added in an amount ranging from 0.1% to 95%, alternatively 1% to 60%, based on the weight of the composition. The exact amount of starting material (f1) depends on various factors including the form of the reaction product of the composition and whether any other fillers are added. Examples of suitable reinforcing fillers include reinforcing silica fillers such as fume silica, silica aerogel, silica xerogel, and precipitated silica. Fumed silicas are known in the art and commercially available; e.g., fumed silica sold under the name CAB-O-SIL by Cabot Corporation of Massachusetts, U.S.A.

[0045] The composition may optionally further comprise starting material (f2) an extending filler in an amount ranging from 0.1 % to 95 %, alternatively 1 % to 60 %, and alternatively 1 % to 20 %, based on the weight of the composition. Examples of extending fillers include crushed quartz, aluminum oxide, magnesium oxide, calcium carbonate such as ground or precipitated calcium carbonate, zinc oxide, talc, diatomaceous earth, iron oxide, clays, mica, chalk, titanium dioxide, zirconia, sand, carbon black, graphite, hollow or plain glass beads, hollow plastics or a combination thereof. Extending fillers are known in the art and commercially available; such as a ground silica sold under the name MIN-U-SIL by U.S. Silica of Berkeley Springs, WV. Suitable precipitated calcium carbonates included Winnofil™ SPM from Solvay and Ultrapflex™ and Ultrapflex™ 100 from SMI.

[0046] The composition may optionally further comprise starting material (f3) a conductive filler. Conductive fillers may be thermally conductive, electrically conductive, or both. Conductive fillers are known in the art and are exemplified by metal particulates, metals coated on nonconductive substrates; metal oxides, meltable fillers (e.g., solder), aluminum nitride, aluminum trihydrate, barium titanate, boron nitride, carbon fibers, diamond, graphite, magnesium hydroxide, onyx, silicon carbide, tungsten carbide, and a combination thereof.

[0047] Alternatively, other fillers may be added to the composition, the type and amount depending on factors including the end use of the cured product of the composition. Examples of such other fillers include fibrous fillers such as glass fibers, carbon fibers and organic fibers, magnetic particles such as ferrite; and dielectric particles such as fused glass microspheres,titania, and calcium carbonate. (G) Treating Agent

[0048] The composition may optionally further comprise starting material (G) a treating agent. The amount of (G) the treating agent can vary depending on factors such as the type of treating agent selected and the type and amount of particulates to be treated, and whether the particulates are treated before being added to the composition, or whether the particulates are treated in situ. However, starting material (G) may be used in an amount ranging from 0.01 % to 20 %, alternatively 0.1 % to 15 %, and alternatively 0.5 % to 5 %, based on the weight of the composition. Particulates, such as the filler, the physical drying agent, certain flame retardants, certain pigments, and / or certain water release agents, when present, may optionally be surface treated with starting material (G). Particulates may be treated with starting material (G) before being added to the composition, or in situ. Starting material (G) may comprise an alkoxysilane, an alkoxy-functional oligosiloxane, a cyclic polyorganosiloxane, a hydroxyl-functional oligosiloxane such as a dimethyl siloxane or methyl phenyl siloxane, or a fatty acid. (H) Biocide

[0049] Starting material (H) is a biocide. The amount of starting material (H) can vary depending on factors including the type of biocide selected and the benefit desired. However, the amount of starting material (H) may range from greater than 0 % to 5 % based on the weight of all starting materials in the composition. Starting material (H) is exemplified by (h1) a fungicide, (h2) an herbicide, (h3) a pesticide, (h4) an antimicrobial, or a combination thereof. (J) Flame Retardant

[0050] Starting material (J) is a flame retardant. Suitable flame retardants may include, for example, carbon black, hydrated aluminum hydroxide, and silicates such as wollastonite, platinum and platinum compounds. Alternatively, the flame retardant may be a halogen based flame-retardant, a phosphorus based flame-retardant, or a tetraalkyl lead compound. The amount of flame retardant can vary depending on factors such as the flame retardant selected and whether solvent is present. However, the amount of flame retardant in the composition may range from greater than 0 % to 10 % based on the combined weight of all starting materials in the composition. (K) Surface Modifier

[0051] Starting material (K) is a surface modifier. Suitable surface modifiers are exemplified by (k1) an adhesion promoter or (k2) a release agent. Suitable adhesion promoters for starting material (k1) may comprise a transition metal chelate, a hydrocarbonoxysilane such as an alkoxysilane, a combination of an alkoxysilane and a hydroxy-functional polyorganosiloxane, or a combination thereof. Adhesion promoters are known in the art and may comprise silaneshaving the formula R24tR25sSi(OR26)4-(t + s) where each R24is independently a monovalent organic group having at least 3 carbon atoms; R25contains at least one SiC bonded substituent having an adhesion-promoting group, such as amino, epoxy, mercapto or acrylate groups; subscript t has a value ranging from 0 to 2; subscript s is either 1 or 2; and the sum of (t + s) is not greater than 3. Each R26is independently a saturated hydrocarbon group. Saturated hydrocarbon groups for R26may be, for example, an alkyl group of 1 to 4 carbon atoms, alternatively 1 to 2 carbon atoms. Alternatively, the adhesion promoter may comprise a partial condensate of the above silane. Alternatively, the adhesion promoter may comprise a combination of an alkoxysilane and a hydroxy-functional polyorganosiloxane.

[0052] Alternatively, the adhesion promoter may comprise an unsaturated or epoxy-functional compound. The adhesion promoter may comprise an unsaturated or epoxy-functional alkoxysilane. Examples of suitable epoxy-functional alkoxysilanes include 3- glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, (epoxycyclohexyl)ethyldimethoxysilane, (epoxycyclohexyl)ethyldiethoxysilane and combinations thereof. Examples of suitable unsaturated alkoxysilanes include vinyltrimethoxysilane, allyltrimethoxysilane, allyltriethoxysilane, hexenyltrimethoxysilane, undecylenyltrimethoxysilane, 3-methacryloyloxypropyl trimethoxysilane, 3- methacryloyloxypropyl triethoxysilane, 3-acryloyloxypropyl trimethoxysilane, 3- acryloyloxypropyl triethoxysilane, and combinations thereof.

[0053] Alternatively, the adhesion promoter may comprise an epoxy-functional siloxane such as a reaction product of a hydroxy-terminated polyorganosiloxane with an epoxy-functional alkoxysilane, as described above, or a physical blend of the hydroxy-terminated polyorganosiloxane with the epoxy-functional alkoxysilane. The adhesion promoter may comprise a combination of an epoxy-functional alkoxysilane and an epoxy-functional siloxane. For example, the adhesion promoter is exemplified by a mixture of 3- glycidoxypropyltrimethoxysilane and a reaction product of hydroxy-terminated methylvinylsiloxane with 3-glycidoxypropyltrimethoxysilane, or a mixture of 3- glycidoxypropyltrimethoxysilane and a hydroxy-terminated methylvinylsiloxane, or a mixture of 3-glycidoxypropyltrimethoxysilane and a hydroxy-terminated methylvinyl / dimethylsiloxane copolymer. Alternatively, the adhesion promoter may comprise a transition metal chelate. Suitable transition metal chelates include titanates, zirconates such as zirconium acetylacetonate, aluminum chelates such as aluminum acetylacetonate, and combinations thereof.

[0054] Starting material (k2) is a release agent. Suitable release agents are exemplified by fluorinated compounds, such as fluoro-functional silicones, or fluoro-functional organic compounds. Alternatively, the surface modifier for starting material (K) may be used to changethe appearance of the surface of a reaction product of the composition. For example, surface modifier may be used to increase gloss of the surface of a reaction product of the composition. Such a surface modifier may comprise a polydiorganosiloxane with alkyl and aryl groups. For example, DOWSIL™ 550 Fluid is a trimethylsiloxy-terminated poly(dimethyl / methylphenyl)siloxane with a viscosity of 125 cSt that is commercially available from Dow Silicones Corporation.

[0055] The exact amount of starting material (K) depends on various factors including the type of surface modifier selected as starting material (K) and the end use of the composition and its reaction product. However, starting material (K), when present, may be added to the composition in an amount ranging from 0.01 part to 50 weight parts based on the weight of the composition, alternatively 0.01 part to 10 weight parts, and alternatively 0.01 part to 5 weight parts. (L) Chain Lengthener / Co-crosslinker

[0056] Chain lengtheners may include difunctional silanes and difunctional siloxanes, which extend the length of polyorganosiloxane chains before crosslinking occurs. Chain lengtheners may be used to reduce the modulus of elongation of the cured product. Chain lengtheners and crosslinkers may compete in their reactions with the reactive moieties of starting materials (A) and (B). To achieve noticeable chain extension, the difunctional silane has substantially higher reactivity than the trifunctional crosslinker with which it is used. Suitable chain lengtheners include diamines, such as alkyl, aryl diamines; diamidosilanes such as dialkyldiacetamidosilanes or alkenylalkyldiacetamidosilanes, particularly methylvinyldi(N-methylacetamido)silane, or dimethyldi(N-methylacetamido)silane, diacetoxysilanes such as dialkyldiacetoxysilanes or alkylalkenyldiacetoxysilanes, diaminosilanes such as dialkyldiaminosilanes or alkylalkenyldiaminosilanes, dialkoxysilanes such as dimethyldimethoxysilane, dimethyldiethoxysilane and α-aminoalkyldialkoxyalkylsilanes, polydialkylsiloxanes having a degree of polymerization of from 2 to 25 and having an average per molecule of at least two hydrolyzable groups, such as acetamido or acetoxy or amino or alkoxy or amido or ketoximo substituents, and diketoximinosilanes such as dialkylkdiketoximinosilanes and alkylalkenyldiketoximinosilanes.

[0057] Alternatively, the chain lengthener may be a bis-hydroxyl terminated polydiorganosiloxane. The bis-hydroxyl terminated polydiorganosiloxane may compriseformula: re each R7is an independently selected monoval mplified above for R5. Alternatively, each R7may be an alkyl group, alternatively methyl. Subscript z ≥ 1, and subscript z has a value sufficient to give the bis-hydroxyl polydiorganosiloxane a viscosity of 250 mPa·s to 1,000 mPa·s at 25 ºC measured by a Modular Compact Rheometer (MCR) 302 from Anton Paar GmbH of Graz, Austria using the most suitable settings and plates for the viscosity concerned, for example using a 25 mm diameter rotational plate with a gap of 0.3 mm at a shear rate of 1 s-1. The bis- hydroxyl terminated polydiorganosiloxane may be used in an amount sufficient to provide a molar ratio of silicon bonded hydroxyl groups (SiOH) in the chain lengthener to alkoxy groups (SiOR) in the other starting materials used to make the composition (SiOH / SiOR) ratio of 1 to 4. (M) Endblocker

[0058] Starting material (M) is an endblocker comprising an M unit, i.e., a siloxane unit of formula R29SiO1 / 2, where each R29independently represents a monovalent organic group unreactive with starting material (B), such as a monovalent hydrocarbon group. Starting material (M) may comprise polyorganosiloxanes endblocked on one terminal end by a triorganosilyl group, e.g., (CH3)3SiO-, and on the other end by a hydroxyl group. Starting material (M) may be a polydiorganosiloxane such as a polydimethylsiloxane. The polydiorganosiloxanes having both hydroxyl end groups and triorganosilyl end groups, may have more than 50 %, alternatively more than 75 %, of the total end groups as hydroxyl groups. The amount of triorganosilyl group in the polydimethylsiloxane may be used to regulate the modulus of the reaction product prepared by condensation reaction of the composition. Without wishing to be bound by theory, it is thought that higher concentrations of triorganosilyl end groups may provide a lower modulus in certain cured products. (N) Non-reactive Binder

[0059] Starting material (N) is a non-reactive, elastomeric, organic polymer, i.e., an elastomeric organic polymer that does not react with starting materials (A) and (B). Starting material (N) is compatible, i.e., starting material (N) does not form a two-phase system with starting materials (A) and (B). Starting material (N) may have low gas and moisture permeability. Starting material (N) may comprise a polyisobutylene. Alternatively, starting material (N) may comprise butyl rubber. Alternatively, starting material (N) may comprise a styrene-ethylene / butylene-styrene (SEBS) block copolymer, a styrene-ethylene / propylene-styrene (SEPS) block copolymer, or a combination thereof. The amount of starting material (N) may range from 0 part to 50 parts, alternatively 10 parts to 40 parts, and alternatively 5 parts to 35 parts, based on the weight of the composition. (O) Anti-Aging Additive

[0060] Starting material (O) is an anti-aging additive. The anti-aging additive may comprise an antioxidant, a UV absorber, a UV stabilizer, a heat stabilizer, or a combination thereof. Suitable antioxidants are known in the art and are commercially available. Suitable antioxidants include phenolic antioxidants and combinations of phenolic antioxidants with stabilizers. Phenolic antioxidants include fully sterically hindered phenols and partially hindered phenols. Alternatively, the stabilizer may be a sterically hindered amine such as tetramethyl-piperidine derivatives. Suitable phenolic antioxidants include 1,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4- hydroxybenzyl)benzene; octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate; butylated hydroxytoluene (BHT); (±)-α-Tocopherol (vitamin E); and IRGANOX™ 1010 from Ciba Specialty Chemicals, U.S.A. IRGANOX™ 1010 comprises pentaerythritol tetrakis(3-(3,5-di-t- butyl-4-hydroxyphenyl)propionate). Examples of UV absorbers include phenol, 2-(2H- benzotriazol-2-yl)-6-dodecyl-4-methyl-, branched and linear (TINUVIN™ 571). Examples of UV stabilizers include bis(1,2,2,6,6-pentamethyl-4-piperidyl) sebacate; methyl 1,2,2,6,6- pentamethyl-4-piperidyl / sebacate; and a combination thereof (TINUVIN™ 272). These and TINUVIN™ additives are commercially available from Ciba Specialty Chemicals of Tarrytown, NY, U.S.A. Other UV and light stabilizers are commercially available, and are exemplified by LowLite from Chemtura, OnCap from PolyOne, and Light Stabilizer 210 from E. I. du Pont de Nemours and Company of Delaware, U.S.A. Oligomeric (higher molecular weight) stabilizers may alternatively be used, for example, to minimize potential for migration of the stabilizer out of the composition or the cured product thereof. An example of an oligomeric antioxidant stabilizer (specifically, hindered amine light stabilizer (HALS)) is Ciba TINUVIN™ 622, which is a dimethylester of butanedioic acid copolymerized with 4-hydroxy-2,2,6,6-tetramethyl-1- piperidine ethanol. Heat stabilizers may include iron oxides and carbon blacks, iron carboxylate salts, cerium hydrate, barium zirconate, cerium and zirconium octoates, and porphyrins.

[0061] The amount of starting material (O) depends on various factors including the specific anti-aging additive selected and the anti-aging benefit desired. However, the amount of starting material (O) may range from 0 to 5%, alternatively 0.1% to 4%, and alternatively 0.5% to 3%, based on the weight of the composition. (P) Water Release Agent

[0062] Starting material (P) is a water release agent that releases water over an application temperature range. Starting material (P) is selected such that starting material (P) contains anamount of water sufficient to partially or fully react the composition and such that starting material (P) releases the sufficient amount of water when exposed for a sufficient amount of time to a use temperature (i.e., a temperature at which the composition is used). However, starting material (P) binds the water sufficiently to prevent too much water from being released during the method for making the composition and during storage of the composition. For example, starting material (P) binds the water sufficiently during compounding of the composition such that sufficient water is available for condensation reaction of the composition during or after the application process in which the composition is used. This “controlled release” property also may provide the benefit of ensuring that not too much water is released too rapidly during the application process, since this may cause bubbling or voiding in the reaction product formed by condensation reaction of the composition. Precipitated calcium carbonate may be used as starting material (P) when the application temperature ranges from 80 °C to 120 °C, alternatively 90 °C to 110 °C, and alternatively 90 °C to 100 °C. However, when the composition is prepared on a continuous (e.g., twin-screw) compounder, the starting materials may be compounded at a temperature 20 °C to 30 °C above the application temperature range for a short amount of time. Therefore, starting material (P) is selected to ensure that not all of the water content is released during compounding; however starting material (P) releases a sufficient amount of water for condensation reaction of the composition when exposed to the application temperature range for a sufficient period of time.

[0063] Examples of suitable water release agents are exemplified by metal salt hydrates, hydrated molecular sieves, and precipitated calcium carbonate, which is available from Solvay under the trademark WINNOFIL™ SPM. The water release agent selected can depend on various factors including the other starting materials selected for the composition, including catalyst type and amount, if present; and the process conditions during compounding, packaging, and application. In a twin-screw compounder, residence time may be less than a few minutes, typically less than 1 to 2 minutes. The starting materials are heated rapidly because the surface area / volume ratio in the barrels and along the screw is high and heat is induced by shearing the starting materials. How much water is removed from starting material (P) depends on the water binding capabilities, the temperature, the exposure time (duration), and the level of vacuum used to strip the composition passing through the compounder. Without wishing to be bound by theory, it is thought that with a twin screw compounding temperature of 120 °C there would remain enough water on the precipitated CaCO3 to cause the composition to react by condensation reaction over a period of 1 to 2 weeks at room temperature when the composition has been applied at 90 °C.

[0064] The amount of starting material (P) in the composition depends on various factorsincluding the selection of starting materials (A) and (B) and whether any additional starting materials are present, however the amount of starting material (P) may range from 5 parts to 30 parts based on the weight of the composition.

[0065] Without wishing to be bound by theory, it is thought the composition can be heated to an application temperature to allow for the heat to liberate the water, and the water would react with hydrolyzable groups on starting materials (A) and / or (B), e.g., when one or both of starting materials (A) and / or (B) also has alkoxy groups, to further cure the composition. (Q) Colorant

[0066] Starting material (Q) is a colorant, e.g., an inorganic pigment or an organic dye. For purposes of this application, the term ‘colorant’ includes any starting material used to impart color to a reaction product of a composition described herein. The amount of colorant depends on various factors including the type of colorant selected and the desired degree of coloration of the reaction product. For example, the composition may comprise 0 to 20%, alternatively 0.001% to 5%, of a colorant based on the weight of all starting materials in the composition.

[0067] Examples of suitable colorants include indigo, titanium dioxide Stan-Tone 50SP01 Green (which is commercially available from PolyOne) and carbon black, which is available from various sources such as Calgon Carbon Corporation of Pittsburgh, Pennsylvania, USA. (R) Rheological Additive

[0068] The composition may optionally further comprise starting material (R) a rheological additive for modifying rheology of the composition. Rheological additives are known in the art and are commercially available. Examples include polyamides, e.g., Polyvest, which is commercially available from Evonik, Disparlon from King Industries, Kevlar Fibre Pulp from Du Pont, Rheospan from Nanocor, and Ircogel from Lubrizol. Other suitable rheological additives include microcrystalline waxes, polyamide waxes; hydrogenated castor oil derivatives; and metal soaps such as calcium stearate, aluminum stearate and barium stearate, and combinations thereof. Without wishing to be bound by theory, it is thought that starting material (R) acts as a process aid that improves flow properties while allowing rapid green strength development (i.e., a strong increase in viscosity, corresponding to increase in the load carrying capability of a seal prepared from the composition, with a temperature drop) upon cooling the composition a few degrees, for example, after the composition is applied to a substrate. The amount of starting material (R) depends on various factors including the specific rheological additive selected and the selections of the other starting materials of the composition. However, the amount of starting material (R) may range from 0 to 20 parts, alternatively 1 part to 15 parts, and alternatively 1 part to 5 parts based on the weight of the composition.(S) Vehicle

[0069] A vehicle (e.g., a solvent and / or diluent) may be used in the composition. The vehicle may facilitate flow of the composition and introduction of certain starting materials, such as silicone resin or catalyst, when used. Vehicles used herein are those that help fluidize the starting materials of the composition but essentially do not react with any of these starting materials. Vehicles may be selected based on solubility the starting materials in the composition and volatility. The solubility refers to the vehicle being sufficient to dissolve and / or disperse starting materials of the composition. Volatility refers to vapor pressure of the vehicle. If the vehicle is too volatile (having too high vapor pressure) bubbles may form in the composition at the application temperature, and the bubbles may cause cracks or otherwise weaken or detrimentally affect properties of the cured product of the composition. However, if the vehicle is not volatile enough (too low vapor pressure) the vehicle may remain as a plasticizer in the reaction product of the composition, or the amount of time for the reaction product to develop physical properties may be longer than desired.

[0070] Suitable vehicles include polyorganosiloxanes with suitable vapor pressures, such as hexamethyldisiloxane, octamethyltrisiloxane, hexamethylcyclotrisiloxane, and other low molecular weight polyorganosiloxanes, such as 0.5 to 1.5 cSt XIAMETER™ PMX 200 Fluids and DOWSIL™ OS FLUIDS, which are commercially available from Dow Silicones Corporation of Midland, Michigan, U.S.A.

[0071] Alternatively, the vehicle may be an organic solvent. The organic solvent can be an alcohol such as methanol, ethanol, isopropanol, butanol, or n-propanol; a ketone such as acetone, methylethyl ketone, or methyl isobutyl ketone; an aromatic hydrocarbon such as benzene, toluene, or xylene; an aliphatic hydrocarbon such as heptane, hexane, or octane; a glycol ether such as propylene glycol methyl ether, dipropylene glycol methyl ether, propylene glycol n-butyl ether, propylene glycol n-propyl ether, or ethylene glycol n-butyl ether, a halogenated hydrocarbon such as dichloromethane, 1,1,1-trichloroethane or methylene chloride; chloroform; dimethyl sulfoxide; dimethyl formamide, acetonitrile; tetrahydrofuran; white spirits; mineral spirits; naphtha; n-methyl pyrrolidone; or a combination thereof. The amount of vehicle depends on various factors including the type of vehicle selected and the amount and type of other starting materials selected for the composition. However, the amount of vehicle may range from 1% to 99%, alternatively 2% to 50%, based on the weight of the composition. (T) Tackifying Agent

[0072] The composition may optionally further comprise starting material (T) a tackifying agent. The tackifying agent may comprise an aliphatic hydrocarbon resin such as a hydrogenated polyolefin having 6 to 20 carbon atoms, a hydrogenated terpene resin, a rosinester, a hydrogenated rosin glycerol ester, or a combination thereof. Tackifying agents are commercially available. (U) Corrosion Inhibitor

[0073] The composition may optionally further comprise starting material (U), a corrosion inhibitor. Examples of suitable corrosion inhibitors include benzotriazole, mercaptobenzothiazole and commercially available corrosion inhibitors such as 2,5-dimercapto- 1,3,4-thiadiazole derivative (CUVAN™ 826) and alkylthiadiazole (CUVAN™ 484) from R. T. Vanderbilt of Norwalk, Connecticut, U.S.A. When present, the amount of starting material (U) may range from 0.05% to 0.5% based on the weight of the composition. (V) Encapsulating Agent

[0074] Starting material (V) is an optional encapsulating agent that may be used, for example, to encapsulate one or more of the other starting materials so as to prepare a one part composition. For example, one or both of starting materials (A) and (B) may be encapsulated in the encapsulating agent before incorporation into the composition. (W) Condensation Reaction Catalyst

[0075] The composition described herein may optionally further comprise (W) a condensation reaction catalyst. Condensation reaction catalysts include metal and non-metal catalysts. Metal catalysts may include tin, titanium, zirconium, lead, iron, cobalt, antimony, manganese, bismuth and / or zinc compounds. For example, the condensation reaction catalyst may comprise organotin compounds such as organic tin esters and organic tin chelate complexes, organic titanium catalysts such as organic titanate esters and organic titanium chelate complexes. Exemplary organotin compounds include dibutyltin dilaurate, dibutyltin diacetate, dibutyltin dimethoxide, tin octoate, dibutyltin oxide, dibutyltin bis-diisooctylphthalate, bistripropoxysilyl dioctyltin, dibutyltin bis-acetylacetone, silylated dibutyltin dioxide, dimethyltin dibutyrate, dimethyltin di-neodecanoate (DMTDN), dibutyltin dibenzoate, tin oleate, tin naphthenate, butyltintri-2-ethylhexylhexanoate, and tinbutyrate. Alternatively, non-metal catalysts may include tetramethylguanidylpropyltrimethoxysilane and tetramethylguanidylpropyl- tristrimethylsiloxysilane. Exemplary organotitanium compounds include tetraisopropoxy titanium. Non-metal catalysts are exemplified by phosphonates (e.g., octyl silyl phosphonate) and phosphonic acids. Suitable non-metal catalysts are known in the art and are commercially available. For example, DOWSIL™ 4-6025 INT and DOWSIL™ 4-6085 Octyl Silyl Phosphonate are available from The Dow Chemical Company. The exact amount of catalyst depends on various factors including the type of catalyst selected, and the hydrolyzable group content of the starting materials in the composition, however, the amount of (W) condensation reaction catalyst may be 0.05% to 3%, based on weight of all starting materials in thecomposition.

[0076] When selecting starting materials for the composition described above, there may be overlap between types of starting materials because certain starting materials described herein may have more than one function. For example, certain alkoxysilanes may be useful as filler treating agents, crosslinkers, drying agents, and / or as adhesion promoters, certain fatty acid esters may be useful as plasticizers and may also be useful as filler treating agents, carbon black may be useful as a pigment, a flame retardant, and / or a filler, and nonreactive polydiorganosiloxanes may be useful as extenders and as solvents.

[0077] One skilled in the art would recognize that the composition described above may be formulated to be cured in the absence of organotin compounds, e.g., as described above for starting material (W). The examples below show that the composition may cure at RT, even in the absence of (W) the condensation reaction catalyst. This is true even if (C) the crosslinker is not present. The starting materials in the composition may be selected by one skilled in the art to increase or decrease cure speed, as desired. Without wishing to be bound by theory, it is thought that the reaction of the amino moiety of (A) (the monoamino-functional organosilicon compound) and the aldehyde moiety of starting material (B) produces water as a by-product, which may enhance cure of the composition, such as when one or more of the starting materials, e.g., (A) the monoamino-functional organosilicon compound, (B) the aldehyde-functional organosilicon compound and / or an additional starting material with alkoxy groups is used in the composition. Method of Making the Composition

[0078] The composition described above may be prepared as a one-part composition, for example, by combining all starting materials by any convenient means, such as mixing. For example, a one-part composition may be made by optionally combining (e.g., premixing) one or both of starting materials (A) and (B) with (V) the encapsulating agent and / or (D) the drying agent before combining (A) and (B). One or more of the optional additional starting materials may be added to the composition at any desired stage. A final mixing step may be performed under substantially anhydrous conditions, and the resulting compositions are generally stored under substantially anhydrous conditions, for example in sealed containers, until ready for use.

[0079] Alternatively, the composition may be prepared as a multiple part (e.g., 2 part) composition. In this instance, starting materials (A) and (B) are stored in separate parts, and the parts are combined shortly before use of the composition. For example, a two-part curable composition may be prepared by combining starting materials comprising (A) and one or more of (C) to (W) to form a first part, and combining starting materials comprising (B) and one or more of (C) to (W) to form a second part, by any convenient means such as mixing. The startingmaterials may be combined at ambient temperature and under ambient or anhydrous conditions. The two parts may be combined by any convenient means, such as mixing, shortly before use. The two parts may be combined in equal amounts, or in an amount of first part to second part of 10:1 to 10:1. The composition will then cure under ambient conditions, e.g. at RT. Exposure to atmospheric moisture may facilitate cure, when one of the starting materials has hydrolyzable groups. The composition may be, for an example, a room temperature vulcanizable (RTV) sealant composition.

[0080] The equipment used for mixing the starting materials is not specifically restricted. Examples of suitable mixing equipment may be selected depending on the type and amount of each starting material selected. For example, agitated batch kettles may be used for relatively low viscosity compositions, such as compositions that would react to form gums or gels. Alternatively, continuous compounding equipment, e.g., extruders such as twin screw extruders, may be used for more viscous compositions and compositions containing relatively high amounts of particulates. Exemplary methods that can be used to prepare the compositions described herein include those disclosed in, for example, US Patent Publications US20090291238 to Scott et al., and US20080300358 to Cook et al. EXAMPLES

[0081] The following examples are provided to illustrate the invention to those skilled in the art and are not to be interpreted as to limit the scope of the invention set forth in the claims. The starting materials used in these examples are summarized below in Table 1. Table 1 – Starting Materials Starting Material Type Chemical Description, Chemical Source formula or StructureStarting Material Type Chemical Description, Chemical Source formula, or Structure R t B2 MPr-aldD Bi di thl l ldhd G td t ThStarting Material Type Chemical Description, Chemical Source formula, or Structure R t AM4 M’DM’ h M’ t DMSA31 f st - -Starting Material Type Chemical Description, Chemical Source formula, or Structure Ctl t 3 DMTDN UL28 tidi thldi d t Gl t

[0082] In Table 1 above, 3-(diethoxy(methyl)silyl)propan-1-amine has formula . Antioxidant 1, Octadecyl 3-(3,5-di-tert-butyl-4-. Antioxidant 4, 2,5,7,8-tetramethyl-2-(4,8,12- trimethyltridecyl)chroman-6-ol, had . Catalyst 2, dibutyl tin dilaurate, had.

[0083] In this Example 1, to a 30 mL vial was added a magnetic stir bar, MPr-ald2D180 (1.98 g, 0.15 mmol, 0.30 mmol CHO 1 eq.) and then 3-aminopropyltriethoxysilane (0.071 g, 0.32 mmol, 1.07 eq.). After the addition of the 3-aminopropyltriethoxysilane, the mixture became turbid. At this time, the sample was transferred to a pre-heated aluminum block at 100 ºC. The sample was heated (loosely capped) at 100 ºC. After 40 min, the sample became more viscous (difficult to be stirred by the stir bar). After 80 min, the sample was fully cured and had turned bright yellow.

[0084] In this Example 2, to a 30 mL vial was added a magnetic stir bar, MPr-ald2D180 (1.99 g, 0.15 mmol, 0.30 mmol CHO 1 eq.) and then 3-aminopropyltrimethoxysilane (0.055 g, 0.31 mmol, 1.02 eq.). After the addition of the 3-aminopropyltrimethoxysilane, the mixture became turbid. At this time, the sample was transferred to a pre-heated aluminum block at 100 ºC. The sample was heated (loosely capped) at 100 ºC. After 4 min, the sample became more viscous (difficult to be stirred by the stir bar). After 20 min, the sample was fully cured and had turned bright yellow.

[0085] In this Example 3, samples were prepared according to the following general experimental procedure: A 40 mL vial equipped with a PTFE magnetic stir bar was charged with MPr-ald2D180(~2.5 g, 0.19 mmol, 0.38 mmol CHO) followed by the addition of 1000 ppm of one of the antioxidants shown above in Table 1 (known volume of an ~100 mg / mL stock solution was added). Each sample was stirred at 1000 RPM for 30 s. At this time, 3- aminopropyltriethoxysilane (2 equiv., 1:1 NH2 / CHO) was added to the vial. The contents were mixed at 1000 RPM for 30 s. At this time, an aliquot was removed and analyzed by1H NMRspectroscopy. In all cases, the conversion of aldehyde groups from MPr-ald2D180 was >99% to the corresponding imine (i.e., bis(imine-terminated) polydimethylsiloxane). The results of this Example 3 demonstrate that use of different antioxidants did not inhibit the reaction of the amine and aldehyde groups under the conditions tested. In each sample, the imine groups were formed with high conversion.

[0086] In this Example 4, compositions were prepared and cured, as follows: A base was prepared as follows: 200g of dimethylsilanol terminated polydimethylsiloxane having an average viscosity of 750 mPa.s at 25°C was introduced into a plastic receptacle of a DAC 600 FVZ / VAC-P type SpeedMixer™ from Hauschild.0.8g of tetraisopropoxy titanium were then added into the dimethylsilanol terminated polydimethylsiloxane. A lid was placed on the receptacle and the initial weight of the starting materials, the receptacle and the lid were weighed together. The starting materials were then mixed in a DAC 600 FVZ / VAC-P type SpeedMixer™ from Hauschild for 6 minutes at 2350 rpm under vacuum and then this mixing step was undertaken a further four times. After completion of the above mixing regime the resulting reaction product, receptacle and lid were re-weighed to determine weight loss due to the extraction of volatile alcohols. The viscosity of the titanium-based reaction product generated via the above process was determined to be 23,000 mPa.s using a Modular Compact Rheometer (MCR) 302 from Anton Paar GmbH of Graz, Austria with a 25 mm diameter rotational plate with a gap of 0.3 mm at a shear rate of 1s-1.

[0087] Curing agents were prepared and combined with samples of the base described above, as follows: 15 g of base prepared as described above were used with 15g of the curing agent to prepare the compositions described in Table 2. In Table 2, amounts of each starting material in the curing agent are in weight % based on combined weights of all starting materials in the curing agent. Table 2 – Curable Compositions Starting Materials CE CE 4- WE 4- 41 2 WE42 CE43 WE43 WE44 1NH2 / CHO molar ratio 0 0 0.31 N / A 0.31 0.31 0.31 PMX-200 fluid 100CS 100 TPT t t i tit i 4 w 0ng. Initially, each composition was colorless, but after aging at 23 ºC and 50% relative humidity for 7 days, some compositions became yellow. This is attributed to the presence of the aminosilane together with the aldehyde functional polydimethylsiloxane.

[0089] Comparative Example CE 4-1 showed that a catalyst (supplied in the base) could be used to cure the comparative composition that did not contain the aldehyde-functional polydiorganosiloxane and the amino-functional silane. Comparative Examples CE 4-2 and CE 4-3 showed compositions that did not cure. Working Example WE4-1 showed that the combination of the aldehyde-functional polydiorganosiloxane with an amino-functional alkoxysilane led to a rapid cure without the presence of a condensation catalyst under the conditions tested. Working Examples WE4-2, WE4-3, and WE4-4 showed that curable compositions containing an aldehyde terminated polydimethylsiloxane and an amino-functional alkoxysilane were curable under the conditions tested. Table 3: Use of aldehyde functional siloxane and amino silane to generate water to speed up gel timeater to speed up gel time Starting Material WE4- WE4- WE4- WE4- WE4- 5WE4-678WE4-91 11 / 1 3 w 8

[0090] Table 3 shows that the use of a proper molar ratio of amino / aldehyde functional groups generated water that sped up gel time of condensation curing elastomers that contained reactants with alkoxy groups under the conditions tested. A molar ratio (NH2 / CHO) of 0.46 / 1 to 1.8 / 1 seemed to be the optimum molar ratio under the conditions tested. The sample with a molar ratio of 0.8 had the fastest gel time under the conditions tested in this Example. Working Examples WE4-5 to WE4-11 show that cure speed may be customized and selected to have a desired rate using this invention.

[0091] In this Example 5, Reagent B-3) was combined with Reagent A-6) to obtain NH2 / CHO ratios from 0 (i.e., pure Reagent B-3)) to 95.18. The samples were monitored at regular intervals to determine when the mixture gelled. From these results, it was surprisingly found that the fastest gel times were observed when the NH2 / CHO ratio was 0.60 to 0.70. These data further emphasize that the NH2 / CHO ratio can impact the gel time. Table 4 – Impact of NH2 / CHO ratio on gel time. Gel time NH2 / CHO d o o o o o es es es es es es es es es es es es es es o

[0092] In this Example 6, MPr-ald2D180and 3-Aminopropyltrimethoxysilane were mixed at r.t. in amounts sufficient to provide a NH2 / CHO mole ratio of 0.95 or 0.66. Samples of MPr-ald2D180 with varying amounts of linear and branched isomers (varying N / I ratios) were prepared and used. The Sample, N / I ratio measured by1H NMR and cure time are shown in Table 5, below. Table 5 – Effect of N / I ratio on cure time Sample NH2 / CHO ratio Reagent B-2, N / I Catalyst 2 Cure TimeSample NH2 / CHO ratio Reagent B-2, N / I Catalyst 2 Cure Time ratio loading (wt%under the conditions tested.

[0094] In this Example 7, curable compositions were prepared as follows, using the amounts shown below in Table 6: Reagent B-2a) was placed in a vial, a drying agent was added into the vial, and the contents of the vial were mixed by hand using a microspatula. Reagent A-7) 3- aminopropyltrimethoxysilane was added to the vial, and the contents of the vial were mixed by hand with a microspatula again. The vials were tipped at regular intervals and checked with a spatula for relative hardness. Results are reported in Table 6 below, where ‘No’ means no change was observed to the vial, ‘viscous’ means the mixture in the vial was more viscous than the starting material, and ‘gelled’ means that loss of flow of the material in the vial occurred. Table 6 – Starting Materials Sample / 7-1 7-2 7-3 7-4 7-5 7-6 7-7 Starting Material

[0095] The samples in Table 6 show that a one part composition including an amino-functional silane and an aldehyde-functional polyorganosiloxane can be prepared with gel times that are customizable by appropriate selection and amount of a drying agent. Sample 7-5 to 7-7 showed that if the amount of drying agent was high (e.g. > 4.37% based on weight of all starting materialsin the composition), the sample was stable and did not cure for at least 9 days. Without wishing to be bound by theory, it is thought that one skilled in the art would be able to optimize the selection and amount of drying agent to achieve a desired gel time for a one part composition.

[0096] In this Example 8, MQ Resin Solution 1, described above (100 g) and 11.06 g 3- (diethoxy(methyl)silyl)propan-1-amine were heated at 100 °C for 4 hours in xylene to make an amino-functional silicate resin (76.1 weight % of the amino-functional silicate resin in 23.9 weight % xylene). The amino-functional silicate resin was evaluated by Si NMR and found to have unit formula M0.4D0.044(NH2)Q0.5506, and the amino-functional silicate resin was evaluated by GPC and found to have Mn = 3,018 g / mol, Mw = 5,975 g / mol, and Mw / Mn = 1.98. The amino-functional silicate resin had (Total Amine Number) TAN =68.3 mg KOH / gm.

[0097] In this Example 9, The amino-functional silicate resin prepared in Example 8 and Reagent B-2a) (bis-dipropyaldehyde-terminated polydimethylsiloxane) were combined in the amounts shown below in Table 7. The starting materials were mixed in a Flak Tek cup at 3500 rpm for one minute. The resultant products were characterized visually as well as by NMR and GPC. Table 7: Compositions amino- TALN function TAN nt t al t in r t e- al eamino- TALN, function TAN, m l m nt t in rmaterials. These materials are gels and cannot be further analyzed by GPC or NMR / viscosity measurements. Samples 9-6A thru 9-9A were lightly cross-linked polymers with increasing viscosity and characterized by13C NMR, GPC and viscosity measurements. The viscosity of the resultant polymers were measured are provided in Table 8. Table 8: Viscosity and Mw of crosslinked polymers described in Table 7 that were not gels Batch Viscosity (cP) MW (Daltons) 9-1A 501 19725

[0099] The3C NMR confirmed the reaction of the aldehyde group with the amine group. New crosslinked polymers, particularly for samples 9-6A thru 9-9A had higher Mw and higher viscosities than the amino-functional silicate resin starting material.

[0100] In this Example 10, an amino-functional siloxane and an aldehyde-functional siloxane were dissolved in toluene at 70% solids (30% toluene). Typically, the aldehyde-functional siloxane was added to the amino-functional siloxane while vigorously mixing with a magnetic stir bar. Mixtures almost instantaneously formed a chemical of physical gel depending on the combinations used. The resulting solvent-borne products were each poured into an open Al dish and placed in a forced air oven set at 120 °C for 30 min followed by 150 °C for 30 min. The solids after solvent evaporation were further processed in a hot press at 150 °C set to 1 ton of pressure for 10 min. Table 9 shows the observations taken after this processing step. Table 9 – Reprocessable Elastomers Made from Amino-Functional Polyorganosiloxane and Aldehyde-Functional PolyorganosiloxaneSample Amino- Aldehyde- Amine Aldehyde Wt% Hot press functional functional reactant reactant MQ reprocessing test il x n il x n m nt m nt n n n ft n ftp , g y y ed by Reagent A-7 to afford NH2 / CHO ratios of 0.62. As can be seen from the data in Table 10, Catalyst 4 and Catalyst 5 are non-tin catalysts which enable cured materials to be generated much faster than when a catalyst is not used. Table 10 – Summary of results using Reagent B-2a and Reagent A-7 with Catalyst 4 and Catalyst 5. Sample NH2 / CHO ratio N / I ratio of Reagent Catalyst Cure Time B-2a Used

[0102] In this Example 12, to a 40 mL vial was added Reagent B-6 (1.11 g, 4.50 mmol, 9.01 mmol CHO) followed by Reagent A-8 (1.11 g, 4.47 mmol, 8.93 mmol NH2, NH2:CHO = 0.99:1. After the addition, the mixture appeared turbid. Upon mixing (with a plastic pipette), a solid material formed instantly. The solid was analyzed by FT-IR (ATR) spectroscopy which indicated formation of imine linkages.

[0103] Rheology was tested on Samples 10-3 and 10-4 in Table 9, as follows. A small strain oscillatory rheology experiment (ARES G2) run at 1Hz and 1% strain as a function of temperature. Both samples 10-3 and 10-4 exhibited rubber elastic behavior with no indication for a flow transition up to 150 °C at this time scale. This was a surprising result in that the hotpress consolidation experiment does indicate flow behavior albeit on a longer time-scale. To confirm the ability of sample 10-4 to exhibit stress relaxation, stress was measured after applying an instantaneous 10% strain at time zero. This experiment was repeated in steps starting at 30 °C up to 90 °C. At each temperature increment, the stress was found to relax in the time-scale of the experiment. This was consistent with the hot press consolidation observation. Resin reinforced elastomers prepared from aldehyde functional MQ and primary amine functional siloxanes formed vitrimers behaving like chemically cross-linked elastomers at small time-scales, but had properties enabling stress relaxation and eventual reflow at longer time- scales, a combination of characteristics previously unattainable with resin reinforced elastomers. Test Methods

[0104] Unless otherwise indicated, viscosity was measured a Modular Compact Rheometer (MCR) 302 from Anton Paar GmbH of Graz, Austria using the most suitable settings and plates for the viscosity concerned, for example using a 25 mm diameter rotational plate with a gap of 0.3 mm at a shear rate of 1s-1.

[0105] NMR spectra were recorded on a 400 MHz (1H: 399.8 MHz;13C: 100.5 MHz) or 500 MHz (1H: 500.1 MHz;13C: 125.8 MHz) Bruker Spectrometer at 25 °C.1H NMR spectra were referenced to residual protons in C6D6(δ = 7.16) or CDCl3(δ = 7.26).13C spectra were referenced to C6D6 (δ = 128.1) or CDCl3 (δ = 77.2). Gel time determination

[0106] Gel time is defined as the time at which the storage modulus G’ and the loss modulus G” coincide. The value of G” / G’ is sometimes referred to as tan δ, and the gel point is to be understood to be when tan δ = G” / G’ = 1. The measurements of G’ and G” were undertaken using the aforementioned Modular Compact Rheometer (MCR) 302 from Anton Paar GmbH of Graz, Austria using a 25 mm diameter rotational plate with a gap of 0.3 mm. As soon as tan δ = G” / G’ was equal to (or less than) 1 the curing composition was considered to have gelled. Unless otherwise indicated these tests were undertaken at a temperature of 25 ºC. The uncured composition was placed in the Modular Compact Rheometer between two plates separated by a gap of 0.3 mm. The upper plate was typically 25 mm in diameter, and the excess composition was removed with a tissue or a spatula. A rotary oscillation was carried out at an angular frequency of 10 rad / s and a shear strain of 1 %. A measurement was made every 30 seconds initially with a descending logarithmic ramp. For example, after 1500 points, the measurements were carried out every 17.5 min. The gel time was defined as the interval of time between when the product was mixed and when the storage modulus G’ and loss modulus G” coincide, i.e., when tan δ was equal to or first less than (≤) 1 on the rheometer. This time was roughly equivalent to the time the composition under test stopped flowing freely.

[0107] Hardness characterization was performed as follows: Hardness and tackiness measurements were typically done after 1, 7 and 28 days of cure on compositions that have been poured with no voids in aluminum or plastic cups. The height of compositions in the cups was 12 to 15 mm for testing of different samples to be comparable. The surface was flat and with no apparent voids or bumps. Measurements were generally made off center on the cups to allow multiple measurements on undisturbed locations of the cups. A TA XT plus texture analyzer from Stable Micro Systems was used to monitor the hardness of the cured elastomers. A return to start program was used. The probe used was finger-like. It was a polycarbonate cylindric probe with semi-spherical end purchased from Stable Micro Systems too (part n°: P / 0.5hs). The diameter of the probe and sphere was ½ inch. The sample was placed onto the Texture Analyzer’s tablet and immobilized to avoid any motion during the measurement. Typically, the operator maintained the cup on the table manually with precaution during measurement. The probe was cleaned with a wiping paper and DOWSIL™ R40 before each measurement. The pre- test speed was 5 mm / s and the trigger force was 0.1g. The test speed was 1 mm / s. The probe penetrated up to 5 mm in the cured elastomer and then the movement was inverted. The probe was removed from the cured elastomer until no significant force was measured. Typically, the maximum positive and negative force were reported. A higher positive force was representative of a harder gel / elastomer. A higher negative force was representative of a tackier gel / elastomer.

[0108] GPC Analysis: SEC instrumentation: SEC was performed on a Waters 2695 LC pump and autosampler. The flow rate was set at 1 mL / min, and the injection volume was set at 100 uL. SEC separation was carried out on 2 Agilent Plgel Mixed-D columns held at 35ºC. The detector was Shodex RI-201 differential refractive index detector held at 35ºC.

[0109] Sample preparation: The samples were prepared in THF eluent at concentration ~ 5 mg / mL polymer and the addition of a few drops of acetic anhydride. The solution was shaken on a flat-bed shaker at ambient temperature for about 2 hours. The solution was filter through a 0.45 um PTFE syringe filter prior to injection.

[0110] Processing of data: Agilent GPC software Cirrus version 3.3 was used for data collection and for data reduction. A total of 16 polystyrene (PS) linear narrow molecular weight standards from Agilent having Mp values from 3752 to 0.58 kg / mol were used for molecular weight calibration. A 3rdorder polynomial was used for calibration curve fitting. Thus, all molecular weight averages, distributions and references to molecular weight provided in this report are PS equivalent values.

[0111] Brookfield Viscosity Measurement: Brookfield instrumentation: A Brookfield DV3T cone / plate Rheometer was utilized with a spindle CPA-40Z. 0.50 mL material was used for measurement. The instrument was maintained at 25 °C by water recirculation. Samplepreparation and procedure: The method is based on ASTM D 4287. The viscometer is leveled. For each series of samples, required parameters to the digital viscometer were entered and position of sample cup adjusted in relation to spindle (cone) as specified by the manufacturer to maintain required clearance. The cup was removed, and 0.5 mL of sample was added to the center of the cup in such a manner that all air bubbles are excluded from the material using a 1 mL syringe. The sample was allowed to equilibrate at 25 + / - 0.1 °C. The motor was started at the specified speed. The digital readout of viscosity was noted. Prior to samples, the instrument was calibrated using a Standard 200 Fluid (viscosity close to samples, if possible) as a control.

[0112] NMR: 2.5 gms to 3 gm of polymer solution and about 5 gm of solvent (CDCl3+Cr(acac)3) were loaded into a 16 mm silicon free NMR tube and the spectra obtained as per conditions and instrumentation in Table 1 Table 10: NMR procedure and instrumentation 29Si Instrument Agilent 500 DD2 NMR Spectrometerp py p p eter using an attenuated total reflectance accessory. Definitions and Usage of Terms

[0114] All amounts, ratios, and percentages herein are by weight, unless otherwise indicated. The amounts of all starting materials in a composition total 100% by weight. The SUMMARY and ABSTRACT are hereby incorporated by reference. The articles ‘a’, ‘an’, and ‘the’ each refer to one or more, unless otherwise indicated by the context of specification. The singular includes the plural unless otherwise indicated. The transitional phrases “comprising”, “consisting essentially of”, and “consisting of” are used as described in the Manual of Patent Examining Procedure Ninth Edition, Revision 08.2017, Last Revised January 2018 at section §2111.03 I., II., and III. The abbreviations used herein have the definitions in Table 12.Table 12 - Abbreviations Abbreviation Definitions °C degrees Celsius - 2 a

Claims

Claims:

1. A curable polyorganosiloxane composition comprising: (A) a monoamine-functional organosilicon compound comprising a silicon bonded amino group of formula -G’-NH2, where G’ is a divalent hydrocarbon group free of aliphatic unsaturation that has 2 to 8 carbon atoms; and (B) an aldehyde-functional organosilicon compound having a silicon bonded aldehydegroup of , where G is a divalent hydrocarbon group free of aliphaticunsaturationatoms; and with the provisos that at least one of (A) and (B) is a polyorganosiloxane, and (A) and (B) are present in amounts sufficient to provide a molar ratio of amino groups to aldehyde groups (NH2 / CHO ratio) of 0.09 / 1 to 31 / 1.

2. The composition of claim 1, wherein (A) the monoamine-functional organosilicon compound is an amino-functional alkoxysilane, and (B) the aldehyde-functional organosilicon compound is an aldehyde-functional polyorganosiloxane.

3. The composition of claim 2, wherein the amino-functional alkoxysilane has general formula RNHmSi(OR6)4-m, wherein RNHis a monoamino-functional group of formula -G’-NH2, wherein G’ is a divalent hydrocarbon group free of aliphatic unsaturation that has 2 to 8 carbon atoms, R6is an alkyl group of 1 to 6 carbon atoms, and subscript m is 1 or 2.

4. The composition of claim 1, wherein (A) the monoamine-functional organosilicon compound is an amino-functional polyorganosiloxane, and (B) the aldehyde-functional organosilicon compound is an aldehyde-functional polyorganosiloxane.

5. The composition of any one of claims 1 to 4, where the aldehyde-functional organosilicon compound is an aldehyde-functional polyorganosiloxane of unit formula:^^ (R43SiO1 / 2)a(R42RAldSiO1 / 2)b(R42SiO2 / 2)c(R4RAldSiO2 / 2)d(R4SiO3 / 2)e(RAldSiO3 / 2)f(SiO4 / 2)g(ZO1 / 2)h; wherein each RAld is the aldehyde group of , where G is the divalenthydrocarbon group free of aliphatic unsaturationatoms;each R4is independently selected from the group consisting of an alkyl group of 1 to 18 carbon atoms, an aryl group of 6 to 18 carbon atoms, and an hydrocarbonoxy group of 1 to 18 carbon atoms; each Z is independently selected from the group consisting of a hydrogen atom and R5, where each R5is independently selected from the group consisting of alkyl groups of 1 to 18 carbon atoms and aryl groups of 6 to 18 carbon atoms; subscripts a, b, c, d, e, f, and g represent numbers of each unit in the unit formula and have values such that subscript a ≥ 0, subscript b ≥ 0, subscript c ≥ 0, subscript d ≥ 0, subscript e ≥ 0, subscript f ≥ 0, subscript g ≥ 0, with the provisos that a quantity (b + d + f) ≥ 1, and 10,000 ≥ (a + b + c + d + e + f + g) ≥ 2; and subscript h has a value such that 0 ≤ h / (e + f + g) ≤ 1.5.^^^ 6. The composition of claim 5, where the aldehyde-functional polyorganosiloxane comprises unit formula: (R43SiO1 / 2)a(R42RAldSiO1 / 2)b(R42SiO2 / 2)c(R4RAldSiO2 / 2)d, where each R4is alkyl or aryl; each RAld is the aldehyde group of , where G is the divalenthydrocarbon group free of aliphatic unsaturationatoms; subscript a is 0, 1, or 2; subscript b is 0, 1, or 2; a quantity (a + b) has an average value of 2; subscript c is 0 or greater, subscript d is 0 or greater; a quantity (b + d) is 1 or greater; and a quantity (c + d) is 1 to 180.

7. The composition of claim 5, wherein the aldehyde-functional polyorganosiloxane comprises an aldehyde-functional polyorganosiloxane resin comprising unit formula:(R43SiO1 / 2)mm(R42RAldSiO1 / 2)nn(SiO4 / 2)oo(ZO1 / 2)h, where Z, R4, and RAld, and subscript h are as described above and subscripts mm, nn and oo have average values such that mm ≥ 0, nn > 0, oo > 0, and 0.5 < (mm + nn) / oo < 4.

8. The composition of any one of claims 1 and 4 to 6, wherein the monoamine-functional organosilicon compound comprises a monoamino-functional polyorganosilicate resin, wherein the monoamino-functional polyorganosilicate resin comprises unit formula: (R43SiO1 / 2)mm(R42RNHSiO1 / 2)nn(SiO4 / 2)oo(ZO1 / 2)h, wherein each RNHis a monoamino-functional group of formula -G’-NH2, wherein G’ is a divalent hydrocarbon group free of aliphatic unsaturation that has 2 to 8 carbon atoms, each R4is independently selected from the group consisting of an alkyl group of 1 to 18 carbon atoms, an aryl group of 6 to 18 carbon atoms, and an hydrocarbonoxy group of 1 to 18 carbon atoms; each Z is independently selected from the group consisting of a hydrogen atom and R5, where each R5is independently selected from the group consisting of alkyl groups of 1 to 18 carbon atoms and aryl groups of 6 to 18 carbon atoms; subscript h has a value such that 0 ≤ h / (e + f + g) ≤ 1.5; subscripts mm, nn and oo have average values such that mm ≥ 0, nn > 0, oo > 0, and 0.5 < (mm + nn) / oo < 4; with the proviso that the monoamino-functional polyorganosilicate resin optionally further comprises one or both units of formulae (R42SiO2 / 2)c(R4RNHSiO2 / 2)d, wherein subscript c ≥ 0 and subscript d ≥ 0.

9. The composition of any one of claims 5 to 8, wherein each R4is alkyl, each RAldis propyl aldehyde, butyl aldehyde or heptyl aldehyde.

10. The composition of claim 1, where (A) the monoamine-functional organosilicon compound is an amino-functional polyorganosiloxane, and (B) the aldehyde-functional organosilicon compound is an aldehyde-functional alkoxysilane.

11. The composition of claim 10, where the amino-functional polyorganosiloxane is a polydiorganosiloxane having a terminal aminoalkyl group, a pendant aminoalkyl group, or both a terminal aminoalkyl group and a pendant aminoalkyl group.

12. The composition of any claim 10 or claim 11, where the aldehyde-functional alkoxysilane has formula: RAldxSi(OR5)(4-x), whereeach RAld is the aldehyde group of formu is the divalenthydrocarbon group free of aliphatic unsaturation ; each R5is an independently selected alkyl group of 1 to 18 carbon atoms; and subscript x is 1 to 4.

13. The composition of claim 12, where each R5is methyl or ethyl, each RAldis propyl aldehyde, butyl aldehyde or heptyl aldehyde.

14. The composition of any one of claims 1 to 13, where the starting materials further comprise an additional starting material selected from the group consisting of (C) a crosslinker; (D) a drying agent; (E) an extender, a plasticizer, or a combination thereof; (F) a filler; (G) a filler treating agent; (H) a biocide; (J) a flame retardant; (K) a surface modifier; (L) a chain lengthener; (M) an endblocker; (N) a nonreactive binder; (O) an anti-aging additive; (P) a water release agent; (Q) a colorant; (R) a rheological additive; (S) a vehicle; (T) a tackifying agent; (U) a corrosion inhibitor; (V) an encapsulating agent; (W) a catalyst; and a combination of two or more thereof.

15. The composition of any one of claims 1 to 14, wherein the aldehyde-amine curable polyorganosiloxane composition is free of organotin compounds, free of bis-hydroxyl- terminated polydiorganosiloxanes, free of solvents, or a combination of two or more thereof.

16. The composition of claim 14, wherein starting materials (A) and (B) are present in amounts sufficient to provide the molar ratio of amino groups to aldehyde groups (NH2 / CHO ratio) of 0.24 / 1 to 1.7 / 1; wherein the composition is free of condensation reaction catalyst.

17. A method for making the composition of any one of claims 1 to 16 comprising: mixing starting materials comprising (A) the monoamine-functional organosilicon compound, and (B) the aldehyde-functional organosilicon compound, so as to make the composition.

18. The method of claim 17, further comprising: adding at least one additional starting material distinct from starting materials (A) and (B), where the at one additional starting material is selected from the group consisting of: (C) a condensation reaction catalyst, (D) a crosslinker; (E) an extender, a plasticizer, or a combination thereof; (F) a filler; (G) a filler treating agent; (H) a biocide; (J) a flame retardant; (K) a surface modifier; (L) a chain lengthener; (M) an endblocker; (N) a nonreactive binder; (O) an anti-aging additive; (P) a water release agent; (Q) a colorant; (R) a rheological additive; (S) a vehicle; (T) a tackifying agent; (U) a corrosion inhibitor; (V) an encapsulating agent, (W) a catalyst; and a combination of two or more thereof.

19. The method of claim 17 or claim 18, wherein the composition is a multiple part composition, and starting material (A) and starting material (B) are stored in separate parts20. A method for preparing a cured polyorganosiloxane, wherein the method comprises: mixing the multiple part composition of claim 19 so as to contact starting material (A) and starting material (B) with one another.

21. The cured polyorganosiloxane prepared by the method of claim 20.

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