Back to results
US 10,597,413 B2Granted
Silicone-compatible compounds
AssigneesHenkel AG & Co. KGaA, Henkel IP & Holding GmbH
InventorsWenjuan Tan, Zhixiang Lu, Hao Wu, Yong Zhang, Zheng Lu, Xuelong Hou
Life of this patent
Estimating the term…
Abstract
Certain phosphonate compounds useful as photoinitiators are provided herein.
Claims28
A photoinitiator of the general Formula I:
- wherein:
- R1, R2, R3, R4, and R5 are the same or different and are selected from the group consisting of SIL1-X, hydrogen, C1-C20 alkyl, C2-C8 alkenyl, C5-C8 cycloalkyl, phenyl C1-C3 alkyl, and fluorine;
- X is optional, and if present is C1-C12 alkyl;
- SIL1 has the general formula:
- (R7SiO3/2)a(R72SiO2/2)b(R73SiO1/2)c
- wherein:
- R7 is selected from the group consisting of C1-C20 alkyl, C2-C8 alkenyl, C5-C8 cycloalkyl, alkoxyl, phenyl, and phenyl C1-C3 alkyl;
- a is a positive number,
- b is 0 or a positive number,
- c is 0 or a positive number,
- b/a is from 0 to 100, and
- c/a is from 0 to 10,
- wherein at least one of R1, R2, R3, R4, and R5 is SIL1-X;
- and
- R6 is selected from the group consisting of C1-C20 alkyl, C2-C8 alkenyl, C5-C8 cycloalkyl, phenyl, phenyl C1-C3 alkyl, trimethylphenol, and fluorine, wherein R3 is SIL1-X and the SIL1-X is selected from the group consisting of:
12 more elements
A photoinitiator of the general Formula I:
- wherein:
- R1, R2, R3, R4, and R5 are the same or different and are selected from the group consisting of SIL1-X, hydrogen, C1-C20 alkyl, C2-C8 alkenyl, C5-C8 cycloalkyl, phenyl C1-C3 alkyl, and fluorine;
- X is optional, and if present is C1-C12 alkyl;
- SIL1 has the general formula:
- (R7SiO3/2)a(R72SiO2/2)b(R73SiO1/2)c
- wherein:
- R7 is selected from the group consisting of C1-C20 alkyl, C2-C8 alkenyl, C5-C8 cycloalkyl, alkoxyl, phenyl, and phenyl C1-C3 alkyl;
- a is a positive number,
- b is 0 or a positive number,
- c is 0 or a positive number,
- b/a is from 0 to 100, and
- c/a is from 0 to 10,
- wherein at least one of R1, R2, R3, R4, and R5 is SIL1-X;
- and
- R6 is selected from the group consisting of a phenyl group, CH3CH2O—, and a trimethylphenol group.
12 more elements
A compound selected from the group consisting of:
- and combinations thereof.
A method of synthesizing a compound of the general Formula I:
- wherein:
- R1, R2, R3, R4, and R5 are the same or different and are selected from the group consisting of SIL1-X, hydrogen, C1-C20 alkyl, C2-C8 alkenyl, C5-C8 cycloalkyl, phenyl C1-C3 alkyl, and fluorine;
- X is optional, and if present is C1-C12 alkyl;
- SIL1 has the general formula:
- (R7SiO3/2)a(R72SiO2/2)b(R73SiO1/2)c
- wherein:
- R7 is selected from the group consisting of C1-C20 alkyl, C2-C8 alkenyl, C5-C8 cycloalkyl, alkoxyl, and phenyl C1-C3 alkyl;
- a is a positive number,
- b is 0 or a positive number,
- c is 0 or a positive number,
- b/a is from 0 to 100, and
- c/a is from 0 to 10,
- wherein at least one of R1, R2, R3, R4, and R5 is SIL1-X;
- and R6 is selected from the group consisting of C1-C20 alkyl, C2-C8 alkenyl, C5-C8 cycloalkyl, phenyl, phenyl C1-C3 alkyl, trimethylphenol, and fluorine, comprising the steps of:
- 1) Activating a compound of Formula A:
- wherein R1, R2, R3, R4, and R5 are as above, but none may be SIL1-X,
- to produce a compound of Formula B:
- 2) Subjecting the compound of Formula B to a nucleophilic acetate substitution reaction to produce a compound of Formula C:
- 3) Subjecting the compound of Formula C to a hydrolysis reaction to produce a compound of Formula D:
- and
- 4) Subjecting the compound of Formula D to a condensation reaction with a compound having the formula SIL1-X—Cl or SIL1-X—H to produce the compound of Formula 1.
18 more elements
A composition comprising:
- a) about 70 to about 99.9 weight percent of a photocurable silicone;
- and
- b) about 0.1 to about 10.0 weight percent of a compound of the general Formula I:
- wherein:
- R1, R2, R3, R4, and R5 are the same or different and are selected from the group consisting of SIL1-X, hydrogen, C1-C20 alkyl, C2-C8 alkenyl, C5-C8 cycloalkyl, phenyl C1-C3 alkyl, and fluorine;
- X is optional, and if present is C1-C12 alkyl;
- SIL1 has the general formula:
- (R7SiO3/2)a(R72SiO2/2)b(R73SiO1/2)c
- wherein:
- R7 is selected from the group consisting of C1-C20 alkyl, C2-C8 alkenyl, C5-C8 cycloalkyl, alkoxyl, phenyl, and phenyl C1-C3 alkyl;
- a is a positive number,
- b is 0 or a positive number,
- c is 0 or a positive number,
- b/a is from 0 to 100, and
- c/a is from 0 to 10,
- wherein at least one of R1, R2, R3, R4, and R5 is SIL1-X;
- and
- R6 is selected from the group consisting of C1-C20 alkyl, C2-C8 alkenyl, C5-C8 cycloalkyl, phenyl, phenyl C1-C3 alkyl, trimethylphenol, and fluorine.
15 more elements
A method of making a silicone polymer product, comprising the steps of:
- A) Providing a photocurable silicone composition comprising:
- i) about 70 to about 99.9 weight percent of a photocurable silicone;
- and
- ii) about 0.1 to about 10.0 weight percent of a compound of the general Formula I:
- wherein:
- R1, R2, R3, R4, and R5 are the same or different and are selected from the group consisting of SIL1-X, hydrogen, C1-C20 alkyl, C2-C8 alkenyl, C5-C8 cycloalkyl, phenyl C1-C3 alkyl, and fluorine;
- X is optional, and if present is C1-C12 alkyl;
- SIL1 has the general formula:
- (R7SiO3/2)a(R72SiO2/2)b(R73SiO1/2)c
- wherein:
- R7 is selected from the group consisting of C1-C20 alkyl, C2-C8 alkenyl, C5-C8 cycloalkyl, alkoxyl, phenyl, and phenyl C1-C3 alkyl;
- a is a positive number,
- b is 0 or a positive number,
- c is 0 or a positive number,
- b/a is from 0 to 100, and
- c/a is from 0 to 10,
- wherein at least one of R1, R2, R3, R4, and R5 is SIL1-X;
- and
- R6 is selected from the group consisting of C1-C20 alkyl, C2-C8 alkenyl, C5-C8 cycloalkyl, phenyl, phenyl C1-C3 alkyl, trimethylphenol, and fluorine;
- and
- B) Exposing the photocurable silicone composition to ultraviolet radiation or visible light to initiate photocuring of the photocurable silicone composition to produce the silicone polymer product.
18 more elements
Dependencies are inferred from the claim text.