Polyoxyalkylene phosphonates and improved process for their synthesis
AssigneeRhodia Inc.
InventorsShiming Wo, John Marshall Baker
Life of this patent
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Abstract
A process for preparing polyoxyalkylene phosphonates in high yield and purity without extensive isolation procedures. The process also enables hydroxy terminated polyoxyalkylene phosphonates to be produced with their attendant high aqueous solubility and the availability of the reactive group to have the end functionality easily molecularly modified. Products produced by these processes have enhanced dispersion, coating, adhesion, and plasticizing characteristics as a result of the lack of any steric hinderance on these polyoxyalkylene phosphonates.
Claims10
A process for producing polyoxyalkylene phosphonates of the formula:
- wherein R1 and R2 are independently H, C1–C20 alkyl, C3–C20 cycloalkyl, or C6–C20 aralkyl;
- R3 is substituted or unsubstituted C2–C20 alkyl, C4–C20 cycloalkyl, or C8–C20 aralkyl;
- R4 and R5 are independently H or C1–C2 alkyl;
- R6 is H, C1–C20 alkyl, C3–C20 cycloalkyl, or C6–C20 aralkyl;
- m and n are independently 1–200, and the moieties to which m and n are subscripted and refer to are either blocked, or randomly spaced, along the chain between the OR3 and R6 groups;
- comprising the steps of
- reacting a polyalkylene glycol alkenyl ether of the formula:
- wherein R4, R5, R6, m and n are as identified in the phosphonate formula above and R7, R8, R9, and R10 are each independently H, C1–C20 alkyl, C3–C20 cycloalkyl, or C6–C20 aralkyl;
- with a phosphite of the formula:
- wherein R1, and R2 are as identified in the phosphonate formula above;
- in the presence of a radical initiator.
A process for producing hydroxy terminated polyoxyalkylene phosphonates of the formula:
- wherein R1 and R2 are independently H, C1–C20 alkyl, C3–C20 cycloalkyl, or C6–C20 aralkyl;
- R3 is substituted or unsubstituted C2–C20 alkyl, C4–C20 cycloalkyl, or C8–C20 aralkyl;
- R4 and R5 are independently H or C1–C2 alkyl;
- m and n are independently 1–200, and the moieties to which m and n are subscripted and refer to are either blocked, or randomly spaced, along the polyoxyalkylene chain;
- comprising the steps of
- reacting a polyalkylene glycol alkenyl ether of the formula:
- wherein R4, R5, R6, m and n are as identified in the phosphonate formula above and R7, R8, R9, and R10 are each independently H, C1–C20 alkyl, C3–C20 cycloalkyl, or C6–C20 aralkyl;
- with a protective compound which can effectively protect the hydroxyl moiety of the polyalkylene glycol alkenyl ether to form a protected polyalkylene glycol alkenyl ether;
- subsequently reacting the protected polyalkylene glycol alkenyl ether with a phosphite of the formula:
- wherein R1, and R2 are as identified in the phosphonate formula above;
- in the presence of a radical initiator;
- and
- hydrolyzing the product of the protected ether and phosphite reaction with water to form a composition containing the hydroxy terminated polyoxyalkylene phosphonate.
A process for producing hydroxy terminated polyoxyalkylene phosphonates of the formula:
- wherein R1 and R2 are independently H, C1–C20 alkyl, C3–C20 cycloalkyl, or C6–C20 aralkyl;
- R3 is substituted or unsubstituted C2–C20 alkyl, C4–C20 cycloalkyl, or C8–C20 aralkyl;
- R4 and R5 are independently H or C1–C2 alkyl;
- m and n are independently 1–200, and the moieties to which m and n are subscripted and refer to are either blocked, or randomly spaced, along the polyoxyalkylene chain;
- comprising the steps of
- reacting a polyalkylene glycol alkenyl ether of the formula:
- wherein R4, R5, R6, m and n are as identified in the phosphonate formula above and R7, R8, R9, and R10 are each independently H, C1–C20 alkyl, C3C20 cycloalkyl, or C6–C20 aralkyl;
- with acetic anhydride to form an acylated polyalkylene glycol alkenyl ether of the formula:
- subsequently reacting the protected polyalkylene glycol alkenyl ether with a phosphite of the formula:
- wherein R1, and R2 are as identified in the phosphonate formula above;
- in the presence of a radical initiator;
- and
- hydrolyzing the product of the acylated ether and phosphite reaction with water to form a composition containing the hydroxy terminated polyoxyalkylene phosphonate.
Dependencies are inferred from the claim text.