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US 12,612,422 B2Granted
Method for making a siloxane-(meth)acrylate macromonomer
AssigneesDow Silicones Corporation, Dow Global Technologies LLC
InventorsSouvagya Biswas, Jason Fisk, Michael Telgenhoff, Eric Joffre
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Abstract
A method for preparing a siloxane-(meth)acrylate macromonomer is provided. The method includes hydrosilylation, hydrolysis, and condensation. By-products of the method may be recycled to produce additional siloxane-(meth) acrylate macromonomer. An exemplary siloxane-(meth)acrylate macromonomer prepared by the method is 3-(1,1,1,3,5,5,5-heptamethyltrisiloxan-3-yl)propyl methacrylate.
Claims17
A method for preparing a siloxane-(meth)acrylate macromonomer, wherein the method comprises:
- (1) hydrosilylating starting materials comprising
- (A) a (meth)acrylate-functional alkenyl compound of formula
- where R1 is selected from the group consisting of H, alkyl, and aryl;
- R3 is selected from the group consisting of H, alkyl, and aryl;
- R4 is selected from the group consisting of H, alkyl, and aryl;
- and subscript a is an integer with a value of 1 to 6;
- and
- (B) a hydridosilane of formula
- where R5 is halogen or alkoxy, and each R6 is independently selected from the group consisting of halogen, alkyl, aryl, and alkoxy;
- in the presence of
- (C) a hydrosilylation reaction catalyst;
- optionally (D) a (meth)acrylate polymerization inhibitor;
- and
- optionally (E) a solvent;
- thereby forming a hydrosilylation reaction product comprising a (meth)acryloxyalkyl-functional silane of formula
- where R1, R3, R4, R5, R6, and subscript a are as defined above;
- (2) hydrolyzing compounds comprising
- (F) the (meth)acryloxyalkyl-functional silane prepared in step (1);
- (G) water;
- and
- (H) an organosilane of formula R23SiR5, where R5 is as described above, and each R2 is independently selected from the group consisting of alkyl and aryl;
- thereby forming a hydrolysis product;
- and
- (3) removing all or a portion of the water from the hydrolysis product which comprises (K) the siloxane-(meth)acrylate macromonomer and a by-product comprising (L) a high boiling oligomer of unit formula
- where R1, R3, R4, and subscript a are as described above, subscript b is 0, 1, or 2, subscript f is 0, 1, or 2, a quantity (b+f)=2, and subscript d is 2 to 10, subscript e is 0 to 9, and a quantity (d+e) is 2 to 10;
- and (M) a low boiling oligomer of formula R23Si—O—SiR23, where R2 is as described above;
- (4) neutralizing the hydrolysis product by a technique comprising adding (I) a neutralizing agent;
- thereby forming a neutralized mixture;
- and
- (5) condensing the neutralized mixture by a technique comprising adding (J) a condensation catalyst;
- thereby preparing a reaction mixture comprising an additional amount of (K) the siloxane-(meth)acrylate macromonomer and additional amount of the by-product comprising (L) the high boiling oligomer and (M) the low boiling oligomer;
- thereby forming a condensation reaction product.
29 more elements
A method for preparing a siloxane-(meth)acrylate macromonomer, wherein the method comprises:
- (1) hydrosilylating starting materials comprising
- (A) a (meth)acrylate-functional alkenyl compound of formula
- where R1 is selected from the group consisting of H, alkyl, and aryl;
- R3 is selected from the group consisting of H, alkyl, and aryl;
- R4 is selected from the group consisting of H, alkyl, and aryl;
- and subscript a is an integer with a value of 1 to 6;
- and
- (B) a hydridohalosilane of formula
- where R5 is halogen, and each R6 is independently selected from the group consisting of halogen and alkyl;
- in the presence of
- (C) a hydrosilylation reaction catalyst;
- optionally (D) a (meth)acrylate polymerization inhibitor;
- and
- optionally (E) a solvent;
- thereby forming a hydrosilylation reaction product comprising a (meth)acryloxyalkyl-functional halosilane of formula
- where R1, R3, R4, R5, R6, and subscript a are as defined above;
- (2) hydrolyzing compounds comprising
- (F) the (meth)acryloxyalkyl-functional halosilane prepared in step (1);
- (G) water;
- and
- (H) an organohalosilane of formula R23SiR5, where R5 is as described above, and R2 is alkyl;
- thereby forming a hydrolysis product;
- (3) removing all or a portion of the water from the hydrolysis product which comprises (K) the siloxane-(meth)acrylate macromonomer and a by-product comprising (L) a high boiling oligomer of unit formula
- where R1, R3, R4, and subscript a are as described above, subscript b is 0, 1, or 2,
- subscript f is 0, 1, or 2, a quantity (b+f)=2, and subscript d is 2 to 4,
- subscript e is 0 or 1, and a quantity (d+e) is 2 to 4;
- and (M) a low boiling oligomer of formula R23Si—O—SiR23, where R2 is as described above;
- optionally (4) neutralizing the hydrolysis product by a technique comprising adding (I) a neutralizing agent;
- thereby forming a neutralized mixture;
- optionally (5) condensing the neutralized mixture by a technique comprising adding (J) a condensation catalyst;
- thereby preparing a reaction mixture comprising an additional amount of (K) the siloxane-(meth)acrylate macromonomer and additional amount of the by-product comprising (L) the high boiling oligomer and (M) the low boiling oligomer;
- thereby forming a condensation reaction product;
- and
- optionally (6) quenching (J) the condensation catalyst by adding (N) a quenching agent to the condensation reaction product, thereby forming a quenched product comprising an inorganic salt of (J) the acid catalyst and (N) the quenching agent;
- optionally (7) equilibrating (L) the high boiling oligomer and (M) the low boiling oligomer in the presence of (O) an additional condensation catalyst (formed in any of the preceding steps);
- thereby forming a further additional amount of (K) the siloxane-(meth)acrylate macromonomer,
- where the method further comprises adding additional fresh (M) low boiling oligomer;
- and
- (8) recovering (K) the siloxane-(meth)acrylate macromonomer.
36 more elements
Dependencies are inferred from the claim text.