US4908228A
Expired / Lapsed
US
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Dioxolane, diol and diacrylate silicon compounds and method for their preparation and use
Assignee: Dow Silicones Corp
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Filing: 1989-04-14
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Granted: 1990-03-13
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Expires: 2009-04-14
Abstract
Abstract Dioxolane-substituted silicon compounds are prepared by a hydrosilylation reaction between a silicon hydride and an aliphatically unsaturated dioxolane compound. The dioxolane-substituted silicon compounds are thereafter converted to diol-substituted silicon compounds and then to diacrylate-substituted silicon compounds. The latter are useful in a curable coating composition for providing a substrate with an adhesive-releasing coating.
Inventors
- 👤 Peter Y. K. Lo
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 14:39
CPC Classifications
C; C08; C08G; C08G77/00; C08G77/04; C08G77/38; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/0801; C07F7/12; C07F7/14
Claims Analysis
Total Claims: 35
Claim 1
Independent Claim
223 words
A method comprising mixing components comprising (i) an amount of a dioxolane compound having the formula ##STR30## (ii) an amount of a silicon hydride compound containing at least one silicon-bonded hydrogen atom, the relative amounts of (i) and (ii) being sufficient to provide one site of aliphatic unsaturation for every silicon-bonded hydrogen atom to be reacted and (iii) an amount of a hydrosilylation catalyst sufficient to accelerate a reaction between the silicon-bonded hydrogen atoms of the silicon hydride with the aliphatic unsaturation of the dioxolane compound; and causing, by heating the mixture, or allowing a hydrosilylation reaction to occur between the dioxolane compound and the silicon hydride compound, thereby forming a dioxolane-substituted organosilicon compound containing at least one silicon-bonded dioxolane radical having the formula ##STR31## where Q' is a monovalent, aliphatically unsaturated organic radical, M is a monovalent hydrocarbon radical free of aliphatic unsaturation containing from 1 to 6 carbon atoms, M' is H or M, and Q is a divalent organic radical which is bonded to a silicon atom by way of a silicon-carbon bond; all remaining silicon valences of the silicon hydride and of the dioxolane-substituted organosilicon compound being satisfied by radicals free of aliphatic unsaturation selected from the group consisting of monovalent hydrocarbon radicals, monovalent halohydrocarbon radicals, monovalent hydrolyzable radicals, hydrogen atoms, divalent radicals joining silicon atoms and mixtures thereof.
Claim 2
Independent Claim
223 words
A method comprising mixing components comprising (i) an amount of a dioxolane compound having the formula ##STR30## (ii) an amount of a silicon hydride compound containing at least one silicon-bonded hydrogen atom, the relative amounts of (i) and (ii) being sufficient to provide one site of aliphatic unsaturation for every silicon-bonded hydrogen atom to be reacted and (iii) an amount of a hydrosilylation catalyst sufficient to accelerate a reaction between the silicon-bonded hydrogen atoms of the silicon hydride with the aliphatic unsaturation of the dioxolane compound; and causing, by heating the mixture, or allowing a hydrosilylation reaction to occur between the dioxolane compound and the silicon hydride compound, thereby forming a dioxolane-substituted organosilicon compound containing at least one silicon-bonded dioxolane radical having the formula ##STR31## where Q' is a monovalent, aliphatically unsaturated organic radical, M is a monovalent hydrocarbon radical free of aliphatic unsaturation containing from 1 to 6 carbon atoms, M' is H or M, and Q is a divalent organic radical which is bonded to a silicon atom by way of a silicon-carbon bond; all remaining silicon valences of the silicon hydride and of the dioxolane-substituted organosilicon compound being satisfied by radicals free of aliphatic unsaturation selected from the group consisting of monovalent hydrocarbon radicals, monovalent halohydrocarbon radicals, monovalent hydrolyzable radicals, hydrogen atoms, divalent radicals joining silicon atoms and mixtures thereof.
Claim 3
Dependent Claim
48 words
A method according to claim 1 wherein the silicon hydride compound is a silane hydride having the formula R a SiHZ.sub.(3-a) ; where Z is said monovalent hydrolyzable radical, a has a value of 0, 1, 2 or 3 and R is said monovalent hydrocarbon or halohydrocarbon radical.
Claim 4
Dependent Claim
27 words
A method according to claim 2 wherein Z is chlorine, R is Me and the dioxolane compound has the formula ##STR32## where Me is a methyl radical.
Claim 5
Dependent Claim
118 words
A method according to claim 1 wherein the silicon hydride is a siloxane hydride having the formula (R'Me.sub.2 SiO).sub.w (Me.sub.2 SiO).sub.x (MeR'SiO).sub.y (MeHSiO).sub.z (SiMe.sub.2 R').sub.w where Me is the methyl radical, R' is selected from the group consisting of hydrogen atoms and said monovalent hydrocarbon and halohydrocarbon radicals, x, y and z have average values of 0 or more and, for linear siloxane hydrides each w has a value of 1 and x+y+z has an average value of 0 or more and for cyclic siloxane hydrides each w has a value of 0, x+y+z has an average value of at least 3, there being an average of at least one silicon-bonded hydrogen atom per molecule of siloxane hydride.
Claim 6
Dependent Claim
14 words
A method according to claim 4 wherein the dioxolane compound has the formula ##STR33##
Claim 7
Dependent Claim
125 words
A method according to claim 1 further comprising mixing with the dioxolane-substituted organosilicon compound (iv) an amount of an olysis agent comprising a compound selected from the group consisting of hydrolysis compounds and alcoholysis compounds, the conditions of said mixing and the amount of olysis agent being sufficient to convert all of said dioxolane radicals to diol radicals, thereby forming a diol-substituted organosilicon compound containing at least one silicon-bonded diol radical having the formula ##STR34## where Q has the stated meaning; all remaining silicon valences of the diol-substituted organosilicon compound being satisfied by radicals free of aliphatic unsaturation selected from the group consisting of monovalent hydrocarbon radicals, monovalent halohydrocarbon radicals, monovalent hydrolyzable radicals, hydroxyl radicals, hydrogen atoms, divalent radicals joining silicon atoms and mixtures thereof.
Claim 8
Dependent Claim
44 words
A method according to claim 6 wherein the dioxolane-substituted organosilicon compound is an organosilane having the formula ##STR35## where Z is said monovalent hydrolyzable radical, a has a value of 0, 1, 2 or 3 and R is said monovalent hydrocarbon or halohydrocarbon radical.
Claim 9
Dependent Claim
29 words
A method according to claim 7 wherein Z is chlorine, R is Me and each of said dioxolane radicals has the formula ##STR36## where Me is a methyl radical.
Claim 10
Dependent Claim
121 words
A method according to claim 6 wherein the dioxolane-substituted organosilicon compound is an organosiloxane having the formula (XMe.sub.2 SiO).sub.w (Me.sub.2 SiO).sub.x (MeXSiO).sub.y (MeHSiO).sub.z (SiMe.sub.2 X).sub.w where Me is a methyl radical, X is selected from the group consisting of hydrogen atoms and said monovalent hydrocarbon and halohydrocarbon radicals and dioxolane radicals, x, y and z have average values of 0 or more and, for linear organosiloxanes each w has a value of 1 and x+y+z has an average value of 0 or more and for cyclic organosiloxanes each w has a value of 0 and x+y+z has an average value of at least 3, there being an average of at least one of said silicon-bonded dioxolane radicals per molecule of organosiloxane.
Claim 11
Dependent Claim
16 words
A method according to claim 9 wherein each of said dioxolane radicals has the formula ##STR37##
Claim 12
Dependent Claim
141 words
A method according to claim 6 further comprising mixing with the diol-substituted organosilicon compound (v) an amount of an acryl compound having the formula CH.sub.2 ═CR"COG where R" is H or CH 3 and G is selected from the group consisting of halogen, hydroxy, alkoxy and CH 2 ═CR"CO 2 --, said amount of acryl compound and the conditions of said mixing being sufficient to convert all of said diol radicals to diacrylate radicals, thereby forming a diacrylate-substituted organosilicon compound containing at least one silicon-bonded diacrylate radical having the formula ##STR38## where Q and R" have the stated meanings, all remaining silicon valences of the diacrylate-substituted organosilicon compound being satisfied by radicals free of aliphatic unsaturation selected from the group consisting of monovalent hydrocarbon radicals, monovalent halohydrocarbon radicals, monovalent hydrolyzable radicals, hydrogen atoms, divalent radicals joining silicon atoms and mixtures thereof.
Claim 13
Dependent Claim
120 words
A method according to claim 11 wherein the diol-substituted organosilicon compound is an organosiloxane having the formula (LMe.sub.2 SiO).sub.w (Me.sub.2 SiO).sub.x (MeLSiO).sub.y (MeHSiO).sub.z (SiMe.sub.2 L).sub.w where Me is a methyl radical, L is selected from the group consisting of said monovalent hydrocarbon and halohydrocarbon radicals, hydrogen atoms and diol radicals, x, y and z have average values of 0 or more and, for linear organosiloxanes each w has a value of 1 and x+y+z has an average value of 0 or more and for cyclic organosiloxanes each w has a value of 0 and x+y+z has an average value of at least 3, there being an average of at least one of said silicon-bonded diol radicals per molecule of organosiloxane.
Claim 14
Dependent Claim
16 words
A method according to claim 12 wherein each of said diol radicals has the formula ##STR39##
Claim 15
Dependent Claim
19 words
An organosilicon compound containing at least one silicon-bonded dioxolane radical that is prepared by the method of claim 1.
Claim 16
Dependent Claim
19 words
An organosilicon compound containing at least one silicon-bonded diol radical that is prepared by the method of claim 6.
Claim 17
Dependent Claim
19 words
An organosilicon compound containing at least one silicon-bonded diacrylate radical that is prepared by the method of claim 11.
Claim 18
Dependent Claim
100 words
A dioxolane-substituted organosilicon compound containing at least one silicon-bonded dioxolane radical having the formula ##STR40## where Q is a divalent organic radical which is bonded to the silicon atom by way of a silicon-carbon bond, M is a monovalent hydrocarbon radical free of aliphatic unsaturation containing from 1 to 6 carbon atoms and M' is H or M; all remaining silicon valences of the dioxolane-substituted organosilicon compound being satisfied by radicals free of aliphatic unsaturation selected from the group consisting of monovalent hydrocarbon radicals, monovalent halohydrocarbon radicals, monovalent hydrolyzable radicals, hydrogen atoms, divalent radicals joining silicon atoms and mixtures thereof.
Claim 19
Dependent Claim
100 words
A dioxolane-substituted organosilicon compound containing at least one silicon-bonded dioxolane radical having the formula ##STR40## where Q is a divalent organic radical which is bonded to the silicon atom by way of a silicon-carbon bond, M is a monovalent hydrocarbon radical free of aliphatic unsaturation containing from 1 to 6 carbon atoms and M' is H or M; all remaining silicon valences of the dioxolane-substituted organosilicon compound being satisfied by radicals free of aliphatic unsaturation selected from the group consisting of monovalent hydrocarbon radicals, monovalent halohydrocarbon radicals, monovalent hydrolyzable radicals, hydrogen atoms, divalent radicals joining silicon atoms and mixtures thereof.
Claim 20
Dependent Claim
37 words
An organosilicon compound according to claim 17 having the formula ##STR41## where Z is said monovalent hydrolyzable radical, a has a value of 0, 1, 2 or 3 and R is said monovalent hydrocarbon or halohydrocarbon radical.
Claim 21
Dependent Claim
30 words
An organosilicon compound according to claim 18 wherein Z is chlorine, R is Me and each of said dioxolane radicals has the formula ##STR42## where Me is a methyl radical.
Claim 22
Dependent Claim
111 words
An organosilicon compound according to claim 17 having the formula (XMe.sub.2 SiO).sub.w (Me.sub.2 SiO).sub.x (MeXSiO).sub.y (MeHSiO).sub.z (SiMe.sub.2 X).sub.w where Me is methyl, X is selected from the group consisting of said monovalent hydrocarbon and halohydrocarbon radicals, hydrogen atoms, and dioxolane radicals, x, y and z have average values of 0 or more and, for linear organosiloxanes each w has a value of 1 and x+y+z has an average value of 0 or more and for cyclic organosiloxanes each w has a value of 0 and x+y+z has an average value of at least 3, there being an average of at least one of said silicon-bonded dioxolane radicals per molecule of organosiloxane.
Claim 23
Dependent Claim
17 words
An organosilicon compound according to claim 20 wherein each of said dioxolane radicals has the formula ##STR43##
Claim 24
Dependent Claim
79 words
An diol-substituted organosilicon compound containing at least one silicon-bonded diol radical having the formula ##STR44## where Q is a divalent organic radical which is bonded to the silicon atom by way of a silicon-carbon bond; all remaining silicon valences of the diol-substituted organosilicon compound being satisfied by radicals free of aliphatic unsaturation selected from the group consisting of monovalent hydrocarbon radicals, monovalent halohydrocarbon radicals, monovalent hydrolyzable radicals, hydroxyl radicals, hydrogen atoms, divalent radicals joining silicon atoms and mixtures thereof.
Claim 25
Dependent Claim
79 words
An diol-substituted organosilicon compound containing at least one silicon-bonded diol radical having the formula ##STR44## where Q is a divalent organic radical which is bonded to the silicon atom by way of a silicon-carbon bond; all remaining silicon valences of the diol-substituted organosilicon compound being satisfied by radicals free of aliphatic unsaturation selected from the group consisting of monovalent hydrocarbon radicals, monovalent halohydrocarbon radicals, monovalent hydrolyzable radicals, hydroxyl radicals, hydrogen atoms, divalent radicals joining silicon atoms and mixtures thereof.
Claim 26
Dependent Claim
111 words
An organosilicon compound according to claim 22 having the formula (LMe.sub.2 SiO).sub.w (Me.sub.2 SiO).sub.x (MeLSiO).sub.y (MeHSiO).sub.z (SiMe.sub.2 L).sub.w where Me is methyl, L is selected from the group consisting of said monovalent hydrocarbon and halohydrocarbon radicals, hydrogen atoms, and diol radicals, x, y and z have average values of 0 or more and for linear organosiloxanes each w has a value of 1 and x+y+z has an average value of 0 or more and for cyclic organosiloxanes each w has a value of 0 and x+y+z has an average value of at least 3, there being an average of at least one of said silicon-bonded diol radicals per molecule of organosiloxane.
Claim 27
Dependent Claim
17 words
An organosilicon compound according to claim 23 wherein each of said diol radicals has the formula ##STR45##
Claim 28
Dependent Claim
88 words
A composition comprising a diacrylate-substituted organosilicon compound containing at least one silicon-bonded diacrylate radical having the formula ##STR46## where Q is a divalent organic radical which is bonded to the silicon atom by way of a silicon-carbon bond and R" is H or CH 3 ; all remaining silicon valences of the diacrylate-substituted organosilicon compound being satisfied by radicals free of aliphatic unsaturation selected from the group consisting of monovalent hydrocarbon radicals, monovalent halohydrocarbon radicals, monovalent hydrolyzable radicals, hydrogen atoms, divalent radicals joining silicon atoms and mixtures thereof.
Claim 29
Dependent Claim
88 words
A composition comprising a diacrylate-substituted organosilicon compound containing at least one silicon-bonded diacrylate radical having the formula ##STR46## where Q is a divalent organic radical which is bonded to the silicon atom by way of a silicon-carbon bond and R" is H or CH 3 ; all remaining silicon valences of the diacrylate-substituted organosilicon compound being satisfied by radicals free of aliphatic unsaturation selected from the group consisting of monovalent hydrocarbon radicals, monovalent halohydrocarbon radicals, monovalent hydrolyzable radicals, hydrogen atoms, divalent radicals joining silicon atoms and mixtures thereof.
Claim 30
Dependent Claim
116 words
A composition according to claim 25 wherein the organosilicon compound has the formula (AMe.sub.2 SiO).sub.w (Me.sub.2 SiO).sub.x (MeASiO).sub.y (MeHSiO).sub.z (SiMe.sub.2 A).sub.w where Me is the methyl radical, A is selected from the group consisting of said monovalent hydrocarbon and halohydrocarbon radicals, hydrogen atoms, and diacrylate radicals, x, y and z have average values of 0 or more and for linear organosiloxanes each w has a value of 1 and x+y+z has an average value of 0 or more and for cyclic organosiloxanes each w has a value of 0 and x+y+z has an average value of at least 3, there being an average of at least one of said silicon-bonded diacrylate radicals per molecule of organosiloxane.
Claim 31
Dependent Claim
16 words
A composition according to claim 26 wherein each of said diacrylate radicals has the formula ##STR47##
Claim 32
Dependent Claim
118 words
A process comprising applying a composition comprising a diacrylate-substituted organosilicon compound to a substrate and thereafter exposing the applied coating to acrylate-polymerizing radiation until said organosilicon compound has been converted to the solid state, said organosilicon compound contains at least one silicon-bonded diacrylate radical having the formula ##STR48## where Q is a divalent organic radical which is bonded to the silicon atom by way of a silicon-carbon bond and R" is H or CH 3 ; all remaining silicon valences of the diacrylate-substituted organosilicon compound being satisfied by radicals free of aliphatic unsaturation selected from the group consisting of monovalent hydrocarbon radicals, monovalent halohydrocarbon radicals, monovalent hydrolyzable radicals, hydrogen atoms, divalent radicals joining silicon atoms and mixtures thereof.
Claim 33
Dependent Claim
118 words
A process comprising applying a composition comprising a diacrylate-substituted organosilicon compound to a substrate and thereafter exposing the applied coating to acrylate-polymerizing radiation until said organosilicon compound has been converted to the solid state, said organosilicon compound contains at least one silicon-bonded diacrylate radical having the formula ##STR48## where Q is a divalent organic radical which is bonded to the silicon atom by way of a silicon-carbon bond and R" is H or CH 3 ; all remaining silicon valences of the diacrylate-substituted organosilicon compound being satisfied by radicals free of aliphatic unsaturation selected from the group consisting of monovalent hydrocarbon radicals, monovalent halohydrocarbon radicals, monovalent hydrolyzable radicals, hydrogen atoms, divalent radicals joining silicon atoms and mixtures thereof.
Claim 34
Dependent Claim
116 words
A process according to claim 28 wherein the organosilicon compound has the formula (AMe.sub.2 SiO).sub.w (Me.sub.2 SiO).sub.x (MeASiO).sub.y (MeHSiO).sub.z (SiMe.sub.2 A).sub.w where Me is the methyl radical, A is selected from the group consisting of said monovalent hydrocarbon and halohydrocarbon radicals, hydrogen atoms, and diacrylate radicals, x, y and z have average values of 0 or more and for linear organosiloxanes each w has a value of 1 and x+y+z has an average value of 0 or more and for cyclic organosiloxanes each w has a value of 0 and x+y+z has an average value of at least 3, there being an average of at least one of said silicon-bonded diacrylate radicals per molecule of organosiloxane.
Claim 35
Dependent Claim
16 words
A process according to claim 29 wherein each of said diacrylate radicals has the formula ##STR49##
References Cited (Backward Citations)
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1993-03-12 | 1993-09-11 | 1994-03-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-03-12 | 1997-09-11 | 1998-03-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-03-12 | 2001-09-11 | 2002-03-13 | $7700.00 | Window Closed / Lapsed |