Alkoxysilane-functionalized hydrocarbon compounds, intermediates thereof and methods of preparation thereof
View Patent ↗A process for preparing moisture curable compounds and moisture curable compositions prepared from the product of that process is provided.
1. A process for preparing alkoxysilane-functionalized hydrocarbon compounds, comprising:
A. Providing (a) an hydroxyl-functionalized compound comprising
wherein L is alkyl or poly(alkyl), alkylene or poly(alkylene), alkenyl or poly(alkenyl), alkenylene or poly(alkenylene), aromatic or an aromatic ring system, R′ is alkyl, and m is 1-10 and n is 1-4, or
and (b) an isocyanatoalkylalkoxysilane, and optionally (c) organic solvent, and
B. Mixing (a), (b) and if present (c) for a time sufficient to form an alkoxysilane-functionalized hydrocarbon compound.
2. The process of claim 1 , wherein the alkoxysilane-functionalized hydrocarbon compound is within structure III or IV, respectively
wherein L is alkyl or poly(alkyl), alkylene or poly(alkylene), alkenyl or poly(alkenyl), alkenylene or poly(alkenylene), aromatic or an aromatic ring system, R′ is alkyl, R 1 and R 2 are each independently selected from alkyl groups having from 1 to 4 carbon atoms, and R 3 is selected from alkylene and arylene residues, and m is 1-10, n is 1-4, and x and y are each independently 0-3, such that when x is 3, y is 0 and when x is 2, y is 1, or
wherein L′ is alkyl or poly(alkyl), alkylene or poly(alkylene), alkenyl or poly(alkenyl), alkenylene or poly(alkenylene), aromatic or an aromatic ring system, R″ is alkyl, R 1 and R 2 are each independently selected from alkyl groups having from 1 to 4 carbon atoms, and R 3 is selected from alkylene and arylene residues, and m is 1-10, n is 1-4, and x and y are each independently 0-3, such that when x is 3, y is 0 and when x is 2, y is 1.
3. The process of claim 1 , wherein the organic solvent is ethyl acetate.
4. The process of claim 1 , wherein mixing occurs at elevated temperature.
5. The process of claim 1 , wherein mixing at elevated temperature occurs for a period of time of about 2 to about 24 hours.
6. The process of claim 1 , wherein mixing at elevated temperature occurs for a period of time of about 2 to about 24 hours to achieve a yield of greater than about 90% of the alkoxysilane-functionalized hydrocarbon compound.
7. The process of claim 1 , wherein the compound shown in structure I or II was made by a controlled radical polymerization technique.
8. A process for preparing alkoxysilane-functionalized hydrocarbon compounds, comprising:
A. Providing
wherein L is alkyl or poly(alkyl), alkylene or poly(alkylene), alkenyl or poly(alkenyl), alkenylene or poly(alkenylene), aromatic or an aromatic ring system, X is a leaving group, R′ is alkyl, and n is 1-4, or
wherein L′ is alkyl or poly(alkyl), alkylene or poly(alkylene), alkenyl or poly(alkenyl), alkenylene or poly(alkenylene), aromatic or an aromatic ring system, X is a leaving group, R″ is alkyl, and n is 1-4, an hydroxyl-containing carboxylic acid, base, and optionally organic solvent, and reacting for a time sufficient to form an hydroxyl functionalized hydrocarbon compound within structure I or II, respectively,
wherein L is alkyl or poly(alkyl), alkylene or poly(alkylene), alkenyl or poly(alkenyl), alkenylene or poly(alkenylene), aromatic or an aromatic ring system, R′ is alkyl, and m is 1-10 and n is 1-4, or
wherein L′ is alkyl or poly(alkyl), alkylene or poly(alkylene), alkenyl or poly(alkenyl), alkenylene or poly(alkenylene), aromatic or an aromatic ring system, R″ is alkyl, and m is 1-10 and n is 1-4, and
B. Providing a compound within structure I or II, an isocyanatoalkylalkoxysilane, and optionally organic solvent, and reacting for a time sufficient to form an alkoxysilane-functionalized hydrocarbon compound.
9. The process of claim 8 , wherein the alkoxysilane-functionalized hydrocarbon compound is within structure III or IV, respectively
wherein L is alkyl or poly(alkyl), alkylene or poly(alkylene), alkenyl or poly(alkenyl), alkenylene or poly(alkenylene), aromatic or an aromatic ring system, R′ is alkyl, R 1 and R 2 are each independently selected from alkyl groups having from 1 to 4 carbon atoms, and R 3 is selected from alkylene and arylene residues, and m is 1-10, n is 1-4, and x and y are each independently 0-3, such that when x is 3, y is 0 and when x is 2, y is 1, or
wherein L′ is alkyl or poly(alkyl), alkylene or poly(alkylene), alkenyl or poly(alkenyl), alkenylene or poly(alkenylene), aromatic or an aromatic ring system, R″ is alkyl, R 1 and R 2 are each independently selected from alkyl groups having from 1 to 4 carbon atoms, and R 3 is selected from alkylene and arylene residues, and m is 1-10, n is 1-4, and x and y are each independently 0-3, such that when x is 3, y is 0 and when x is 2, y is 1.
10. An alkoxysilane-functionalized hydrocarbon compound made in accordance with the process of claim 1 .
11. An alkoxysilane-functionalized hydrocarbon compound within structure HI or IV, respectively
wherein L is alkyl or poly(alkyl), alkylene or poly(alkylene), alkenyl or poly(alkenyl), alkenylene or poly(alkenylene), aromatic or an aromatic ring system, R′ is alkyl, R 1 and R 2 are each independently selected from alkyl groups having from 1 to 4 carbon atoms, and R 3 is selected from alkylene and arylene residues, and m is 1-10, n is 1-4, and x and y are each independently 0-3, such that when x is 3, y is 0 and when x is 2, y is 1, or
wherein L′ is alkyl or poly(alkyl), alkylene or poly(alkylene), alkenyl or poly(alkenyl), alkenylene or poly(alkenylene), aromatic or an aromatic ring system, R″ is alkyl, R 1 and R 2 are each independently selected from alkyl groups having from 1 to 4 carbon atoms, and R 3 is selected from alkylene and arylene residues, and m is 1-10, n is 1-4, and x and y are each independently 0-3, such that when x is 3, y is 0 and when x is 2, y is 1.
12. A moisture curable composition, comprising:
(a) an alkoxysilane-functionalized hydrocarbon compound of claim 11 ; and
(b) a moisture cure catalyst.
13. The composition of claim 12 , further comprising one or more of a filler component, a toughening component, a plasticizer component and a cross linker component.
14. The process of claim 8 , wherein X is a halogen, tosylate or mesylate.
15. The process of claim 14 , wherein the halogen is selected from chlorine, bromine or iodine.
16. The process of claim 8 , wherein the base is potassium carbonate or a trialkyl amine.