US 10,590,242 B2 · Method for producing hydrosilyl group-containing organic silicon resin · patentgrep

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Abstract

A method for producing a hydrosilyl group-containing organic silicon resin of formula (6) in a solid form, wherein after formulae (1) to (3) are hydrolyzed in the presence of an acid catalyst, hydrolysis is carried out by adding hydrosilyl group-containing organic silicon compounds of formulae (4) and (5), followed by neutralization by a base catalyst with the amount thereof being more than a molar equivalent of the acid catalyst, and then by condensation. By so doing, deactivation amount of the hydrosilyl group can be reduced, so that the method for producing the hydrosilyl group-containing organic silicon resin, which is in a solid form without a solvent and to which a hydrosilyl group can be introduced quantitatively and in a large quantity, is provided, R13SiOSiR13 (1) R13SiX1 (2) SiX24 (3) HnR23-nSiOSiR23-nHn (4) HnR23-nSiX3 (5) (R13SiO1/2)a(HnR23-nSiO1/2)b(SiO2)c(R4SiO3/2)d (6).

Claims17

Dependent claims

A method for producing a hydrosilyl group-containing organic silicon resin, wherein

after a mixture of one, or two or more of organic silicon compounds represented by following general formulae (1) and (2) with any one or more of a hydrolysable silane represented by following general formula (3), a partial hydrolysis condensate of the hydrolysable silane, and a metal salt of the hydrolysable silane is hydrolyzed in a presence of an acid catalyst,
to a hydrolyzate thereby obtained, one, or two or more of hydrosilyl group-containing organic silicon compounds represented by following general formulae (4) and (5) is added, which is then followed by re-hydrolysis,
and thereafter, neutralization is done by adding a base catalyst with an amount of more than a molar equivalent of the acid catalyst,
which is followed by condensation to obtain a hydrosilyl group-containing organic silicon resin represented by following average composition formula (6), which contains a Q-unit (SiO2) and an M-unit ((R13SiO1/2) and (HnR23-nSiO1/2)) as essential components, and which is in a solid form without a solvent,
R13SiOSiR13 (1)
R13SiX1 (2)
wherein R1 may be the same or different with each other, representing an unsubstituted or substituted monovalent hydrocarbon group;
and X1 represents a hydrolysable functional group,
SiX24 (3)
wherein X2 represents a hydrolysable functional group,
HnR23-nSiOSiR23-nHn (4)
HnR23-nSiX3 (5)
wherein R2 may be the same or different with each other, representing an unsubstituted or substituted monovalent hydrocarbon group;
X3 represents a hydrolysable functional group;
and 1≤n≤3, and
(R13SiO1/2)a(HnR23-nSiO1/2)b(SiO2)c (6)
wherein R1, R2 and “n” represents the same as before;
and 0<a≤1.5, 0.2≤b≤1.5, 0<c≤1.0, and 0.5≤a+b/c≤1.0.

15 more elements

A method for producing a hydrosilyl group-containing organic silicon resin, wherein

after a mixture of one, or two or more of organic silicon compounds represented by following general formulae (1) and (2) with any one or more of a hydrolysable silane represented by following general formula (3), a partial hydrolysis condensate of the hydrolysable silane, and a metal salt of the hydrolysable silane is hydrolyzed in a presence of an acid catalyst,
to a hydrolyzate thereby obtained, one, or two or more of hydrosilyl group-containing organic silicon compounds represented by following general formulae (4) and (5) is added, which is then followed by re-hydrolysis,
and thereafter, neutralization is done by adding a base catalyst with an amount of more than a molar equivalent of the acid catalyst,
which is followed by condensation to obtain a hydrosilyl group-containing organic silicon resin represented by following average composition formula (6′), which contains a Q-unit (SiO2) and an M-unit ((R13SiO1/2) and (HnR23-nSiO12)) as essential components, and which is in a solid form without a solvent;
wherein one, or a mixture of two or more of organic silicon compounds represented by following general formula (7) is further added before hydrolysis of the mixture of one, or two or more of the organic silicon compounds represented by the general formulae (1) and (2) with any one or more of the hydrolysable silane represented by the general formula (3), the partial hydrolysis condensate of the hydrolysable silane, and the metal salt of the hydrolysable silane, or after this hydrolysis and before re-hydrolysis, the hydrosilyl group-containing organic silicon resin, which is a powder form without a solvent is obtained,
R13SiOSiR13 (1)
R13SiX1 (2)
wherein R1 may be the same or different with each other, representing an unsubstituted or substituted monovalent hydrocarbon group;
and X1 represents a hydrolysable functional group,
SiX24 (3)
wherein X2 represents a hydrolysable functional group,
HnR23-nSiOSiR23-nHn (4)
HnR23-nSiX3 (5)
wherein R2 may be the same or different with each other, representing an unsubstituted or substituted monovalent hydrocarbon group;
X3 represents a hydrolysable functional group;
and 1≤n≤3,
(R13SiO1/2)a(HnR23-nSiO1/2)b(SiO2)c(R4SiO3/2)d (6′)
wherein R1, R2 and “n” represents the same as before;
R4 represents an unsubstituted or substituted monovalent hydrocarbon group;
and 0<a≤1.5, 0.2≤b≤1.5, 0<c≤1.0, 0<d≤1.5, and 0.5≤a+b/c≤1.0, and
(R3O)3SiR4 (7)
wherein R4 represents the same as before;
and R3 may be the same or different with each other, representing an unsubstituted or substituted monovalent hydrocarbon group.

20 more elements

A method for producing a hydrosilyl group-containing organic silicon resin, wherein

after a mixture of one, or two or more of organic silicon compounds represented by following general formulae (1) and (2) with any one or more of a hydrolysable silane represented by following general formula (3), a partial hydrolysis condensate of the hydrolysable silane, and a metal salt of the hydrolysable silane is hydrolyzed in a presence of an acid catalyst,
to a hydrolyzate thereby obtained, one, or two or more of hydrosilyl group-containing organic silicon compounds represented by following general formulae (4) and (5) is added, which is then followed by re-hydrolysis,
and thereafter, neutralization is done by adding a base catalyst with an amount of more than a molar equivalent of the acid catalyst,
which is followed by condensation to obtain a hydrosilyl group-containing organic silicon resin represented by following average composition formula (6′), which contains a Q-unit (SiO2) and an M-unit ((R13SiO1/2) and (HnR23-nSiO1/2)) as essential components, and which is in a solid form without a solvent;
wherein one, or a mixture of two or more of organic silicon compounds represented by following general formula (7) is further added before hydrolysis of the mixture of one, or two or more of the organic silicon compounds represented by the general formulae (1) and (2) with any one or more of the hydrolysable silane represented by the general formula (3), the partial hydrolysis condensate of the hydrolysable silane, and the metal salt of the hydrolysable silane, or after this hydrolysis and before re-hydrolysis, the hydrosilyl group-containing organic silicon resin, which is a powder form without a solvent is obtained,
R13SiOSiR13 (1)
R13SiX1 (2)
wherein R1 may be the same or different with each other, representing an unsubstituted or substituted monovalent hydrocarbon group;
and X1 represents a hydrolysable functional group,
SiX24 (3)
wherein X2 represents a hydrolysable functional group,
HnR23-nSiOSiR23-nHn (4)
HnR23-nSiX3 (5)
wherein R2 may be the same or different with each other, representing an unsubstituted or substituted monovalent hydrocarbon group;
X3 represents a hydrolysable functional group;
and 1≤n≤3,
(R13SiO1/2)a(HnR23-nSiO1/2)b(SiO2)c(R4SiO3/2)d (6′)
wherein R1, R2 and “n” represents the same as before;
R4 represents an unsubstituted or substituted monovalent hydrocarbon group;
and 0<a≤1.5, 0.2≤b≤1.5, 0<c≤1.0, 0<d≤1.5, and 0.5≤a+b/c≤1.0, and
(R3O)3SiR4 (7)
wherein R4 represents the same as before;
and R3 may be the same or different with each other, representing an unsubstituted or substituted monovalent hydrocarbon group;
wherein
in a 29Si—NMR analysis of the produced hydrosilyl group-containing organic silicon resin, an integral value of the peak between −10 and −20 ppm is 1.0% or less relative to total integral value of the entire silicon.

22 more elements

A method for producing a hydrosilyl group-containing organic silicon resin, wherein

after a mixture of one, or two or more of organic silicon compounds represented by following general formulae (1) and (2) with any one or more of a hydrolysable silane represented by following general formula (3), a partial hydrolysis condensate of the hydrolysable silane, and a metal salt of the hydrolysable silane is hydrolyzed in a presence of an acid catalyst,
to a hydrolyzate thereby obtained, one, or two or more of hydrosilyl group-containing organic silicon compounds represented by following general formulae (4) and (5) is added, more than a molar equivalent of the acid catalyst,
which is followed by condensation to obtain a hydrosilyl group-containing organic silicon resin represented by following average composition formula (6′), which contains a Q-unit (SiO2) and an M-unit ((R13SiO1/2) and (HnR23-nSiO1/2)) as essential components, and which is in a solid form without a solvent;
wherein one, or a mixture of two or more of organic silicon compounds represented by following general formula (7) is further added before hydrolysis of the mixture of one, or two or more of the organic silicon compounds represented by the general formulae (1) and (2) with any one or more of the hydrolysable silane represented by the general formula (3), the partial hydrolysis condensate of the hydrolysable silane, and the metal salt of the hydrolysable silane, or after this hydrolysis and before re-hydrolysis, the hydrosilyl group-containing organic silicon resin, which is a powder form without a solvent is obtained,
R13SiOSiR13 (1)
R13SiX1 (2)
wherein R1 may be the same or different with each other, representing an unsubstituted or substituted monovalent hydrocarbon group;
and X1 represents a hydrolysable functional group,
SiX24 (3)
wherein X2 represents a hydrolysable functional group,
HnR23-nSiOSiR23-nHn (4)
HnR23-nSiX3 (5)
wherein R2 may be the same or different with each other, representing an unsubstituted or substituted monovalent hydrocarbon group;
X3 represents a hydrolysable functional group;
and 1≤n≤3,
(R13SiO1/2)a(HnR23-nSiO1/2)b(SiO2)c(R4SiO3/2)d (6′)
wherein R1, R2 and “n” represents the same as before;
R4 represents an unsubstituted or substituted monovalent hydrocarbon group;
and 0<a≤1.5, 0.2≤b≤1.5, 0<c≤1.0, 0<d≤1.5, and 0.5≤a+b/c≤1.0, and
(R3O)3SiR4 (7)
wherein R4 represents the same as before;
and R3 may be the same or different with each other, representing an unsubstituted or substituted monovalent hydrocarbon group;
wherein
after the mixture of one, or two or more of the organic silicon compounds represented by the general formulae (1) and (2) with any one or more of the hydrolysable silane represented by the general formula (3), the partial hydrolysis condensate of the hydrolysable silane, and the metal salt of the hydrolysable silane, is hydrolyzed in the presence of the acid catalyst, the hydrolyzate is cooled down to 25° C.;
and then, after the hydrosilyl group-containing organic silicon compound is added, re-hydrolysis is carried out at a temperature below a boiling point of the used hydrosilyl group-containing organic silicon compound.

22 more elements

A method for producing a hydrosilyl group-containing organic silicon resin, wherein

after a mixture of one, or two or more of organic silicon compounds represented by following general formulae (1) and (2) with any one or more of a hydrolysable silane represented by following general formula (3), a partial hydrolysis condensate of the hydrolysable silane, and a metal salt of the hydrolysable silane is hydrolyzed in a presence of an acid catalyst,
to a hydrolyzate thereby obtained, one, or two or more of hydrosilyl group-containing organic silicon compounds represented by following general formulae (4) and (5) is added, which is then followed by re-hydrolysis,
and thereafter, neutralization is done by adding a base catalyst with an amount of more than a molar equivalent of the acid catalyst,
which is followed by condensation to obtain a hydrosilyl group-containing organic silicon resin represented by following average composition formula (6′), which contains a Q-unit (SiO2) and an M-unit ((R13SiO1/2) and (HnR23-nSiO1/2)) as essential components, and which is in a solid form without a solvent;
wherein one, or a mixture of two or more of organic silicon compounds represented by following general formula (7) is further added before hydrolysis of the mixture of one, or two or more of the organic silicon compounds represented by the general formulae (1) and (2) with any one or more of the hydrolysable silane represented by the general formula (3), the partial hydrolysis condensate of the hydrolysable silane, and the metal salt of the hydrolysable silane, or after this hydrolysis and before re-hydrolysis, the hydrosilyl group-containing organic silicon resin, which is a powder form without a solvent is obtained,
R13SiOSiR13 (1)
R13SiX1 (2)
wherein R1 may be the same or different with each other, representing an unsubstituted or substituted monovalent hydrocarbon group;
and X1 represents a hydrolysable functional group,
SiX24 (3)
wherein X2 represents a hydrolysable functional group,
HnR23-nSiOSiR23-nHn (4)
HnR23-nSiX3 (5)
wherein R2 may be the same or different with each other, representing an unsubstituted or substituted monovalent hydrocarbon group;
X3 represents a hydrolysable functional group;
and 1≤n≤3,
(R13SiO1/2)a(HnR23-nSiO1/2)b(SiO2)c(R4SiO3/2)d (6′)
wherein R1, R2 and “n” represents the same as before;
R4 represents an unsubstituted or substituted monovalent hydrocarbon group;
and 0<a≤1.5, 0.2≤b≤1.5, 0<c≤1.0, 0<d≤1.5, and 0.5≤a+b/c≤1.0, and
(R3O)3SiR4 (7)
wherein R4 represents the same as before;
and R3 may be the same or different with each other, representing an unsubstituted or substituted monovalent hydrocarbon group;
wherein
in neutralization by using the base catalyst, sodium hydroxide as a strong base catalyst and calcium carbonate as a weak base catalyst are concurrently used.

22 more elements

Dependencies are inferred from the claim text.