US4311629A
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US
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Method for making antifouling coating composition containing hydrolyzed organotin siloxane polymer
Assignee: Ameron Inc
•
Filing: 1980-11-12
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Granted: 1982-01-19
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Expires: 2000-11-12
Abstract
Abstract A solution containing hydrolyzed organotin siloxane polymeric material is formed by hydrolyzing an organotin R-oxy siloxane in a water miscible solvent; R being an alkyl or alkoxyalkyl group with less than six carbon atoms. A water immiscible solvent is added and the water miscible solvent and R-alcohol from hydrolysis are removed by distillation. A marine antifouling coating can be made when the water immiscible solvent evaporates from the solution. A preferred embodiment hydrolyzes tributyltin ethoxysiloxane in ethyl alcohol with xylene as the water immiscible solvent.
Inventors
- 👤 A. Peter Gysegem
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 07:44
CPC Classifications
C; C08; C08G; C08G77/00; C08G77/04; C08G77/14; C08G77/18; C09; C09D; C09D183/00; C09D183/02; C08G77/06; C09D5/00; C09D5/14; C09D5/16; C09D5/1606; C09D5/1637; C09D5/1643
Claims Analysis
Total Claims: 46
Claim 1
Independent Claim
90 words
A method for preparing a solution containing hydrolyzed organotin siloxane polymeric material comprising the steps of: combining an organotin R-oxy siloxane in which the ratio of tin atoms to silicon atoms is in the range of 1:50 to 1:1, where R represents a group consisting of alkyl and alkoxyalkyl radicals containing less than six carbon atoms, a water miscible solvent, water, a hydrolysis catalyst, and a water immiscible solvent; and after hydrolysis of the organotin R-oxy siloxane, removing by distillation the water miscible solvent and R-alcohol from the hydrolysis reaction.
Claim 2
Independent Claim
90 words
A method for preparing a solution containing hydrolyzed organotin siloxane polymeric material comprising the steps of: combining an organotin R-oxy siloxane in which the ratio of tin atoms to silicon atoms is in the range of 1:50 to 1:1, where R represents a group consisting of alkyl and alkoxyalkyl radicals containing less than six carbon atoms, a water miscible solvent, water, a hydrolysis catalyst, and a water immiscible solvent; and after hydrolysis of the organotin R-oxy siloxane, removing by distillation the water miscible solvent and R-alcohol from the hydrolysis reaction.
Claim 3
Dependent Claim
20 words
A method as recited in claim 1 wherein sufficient water is combined for substantially completely hydrolyzing the organotin R-oxy siloxane.
Claim 4
Dependent Claim
14 words
A method as recited in claim 1 wherein the water miscible solvent comprises R-alcohol.
Claim 5
Dependent Claim
13 words
A method as recited in claim 3 wherein R is the ethyl radical.
Claim 6
Dependent Claim
14 words
A method as recited in claim 4 wherein the water immiscible solvent comprises xylene.
Claim 7
Dependent Claim
14 words
A method as recited in claim 1 wherein the water immiscible solvent comprises xylene.
Claim 8
Dependent Claim
20 words
A method as recited in claim 6 wherein sufficient water is combined for substantially completely hydrolyzing the organotin R-oxy siloxane.
Claim 9
Dependent Claim
19 words
A method as recited in claim 1 wherein the water immiscible solvent is added after hydrolysis and before distillation.
Claim 10
Dependent Claim
26 words
A method as recited in claim 1 wherein the ratio of tin atoms to silicon atoms in the organotin R-oxy siloxane is less than about 2:5.
Claim 11
Independent Claim
192 words
A method for preparing a solution containing hydrolyzed organotin substituted siloxane polymeric material comprising the steps of: combining a precursor having the formula: ##STR7## wherein m is from about 1 to about 10, each X is independently selected from the group consisting of R and Y, R is selected from the group consisting of alkyl and alkoxyalkyl radicals containing less than about six carbon atoms, and each Y is independently a trisubstituted tin radical having the formula: ##STR8## where R 1 , R 2 , and R 3 are independently selected from the group consisting of alkyl, cycloalkyl, and aryl radicals, and contain in combination up to about eighteen carbon atoms and wherein the ratio of tin atoms to silicon atoms in the precursor is in the range of from about 1:50 to 1:1; a water miscible solvent; water; a source of ions selected from the group consisting of hydrogen ion and hydroxyl ion; and a water immiscible solvent having a boiling point higher than the boiling point of the water miscible solvent; and after hydrolysis of the precursor removing by distillation the water miscible solvent and R-alcohol from the hydrolysis reaction.
Claim 12
Independent Claim
192 words
A method for preparing a solution containing hydrolyzed organotin substituted siloxane polymeric material comprising the steps of: combining a precursor having the formula: ##STR7## wherein m is from about 1 to about 10, each X is independently selected from the group consisting of R and Y, R is selected from the group consisting of alkyl and alkoxyalkyl radicals containing less than about six carbon atoms, and each Y is independently a trisubstituted tin radical having the formula: ##STR8## where R 1 , R 2 , and R 3 are independently selected from the group consisting of alkyl, cycloalkyl, and aryl radicals, and contain in combination up to about eighteen carbon atoms and wherein the ratio of tin atoms to silicon atoms in the precursor is in the range of from about 1:50 to 1:1; a water miscible solvent; water; a source of ions selected from the group consisting of hydrogen ion and hydroxyl ion; and a water immiscible solvent having a boiling point higher than the boiling point of the water miscible solvent; and after hydrolysis of the precursor removing by distillation the water miscible solvent and R-alcohol from the hydrolysis reaction.
Claim 13
Dependent Claim
15 words
A method as recited in claim 10 wherein m is an average of about five.
Claim 14
Dependent Claim
19 words
A method as recited in claim 10 wherein the water immiscible solvent is added after hydrolysis and before distillation.
Claim 15
Dependent Claim
24 words
A method as recited in claim 10 wherein the ratio of tin atoms to silicon atoms in the precursor is less than about 2:5.
Claim 16
Dependent Claim
11 words
A method as recited in claim 10 wherein R is ethyl.
Claim 17
Dependent Claim
15 words
A method as recited in claim 14 wherein the water miscible solvent comprises ethyl alcohol.
Claim 18
Dependent Claim
14 words
A method as recited in claim 15 wherein the water immiscible solvent comprises xylene.
Claim 19
Dependent Claim
14 words
A method as recited in claim 10 wherein the water immiscible solvent comprises xylene.
Claim 20
Dependent Claim
18 words
A method as recited in claim 10 wherein sufficient water is included for substantially completely hydrolyzing the precursor.
Claim 21
Independent Claim
80 words
A method for preparing a solution containing hydrolyzed organotin siloxane polymeric material comprising the steps of: combining trisubstituted-organotin ethoxysiloxane in which the ratio of tin atoms to silicon atoms in the organotin ethoxysiloxane is in the range of from about 1:50 to 1:1, with a water miscible solvent, a source of hydroxyl ion, and a water immiscible solvent; gradually adding water for hydrolyzing the organotin ethoxysiloxane; and removing by distillation the water miscible solvent and ethyl alcohol from such hydrolysis.
Claim 22
Independent Claim
80 words
A method for preparing a solution containing hydrolyzed organotin siloxane polymeric material comprising the steps of: combining trisubstituted-organotin ethoxysiloxane in which the ratio of tin atoms to silicon atoms in the organotin ethoxysiloxane is in the range of from about 1:50 to 1:1, with a water miscible solvent, a source of hydroxyl ion, and a water immiscible solvent; gradually adding water for hydrolyzing the organotin ethoxysiloxane; and removing by distillation the water miscible solvent and ethyl alcohol from such hydrolysis.
Claim 23
Dependent Claim
19 words
A method as recited in claim 19 wherein sufficient water is added for substantially completely hydrolyzing the organotin ethoxysiloxane.
Claim 24
Dependent Claim
15 words
A method as recited in claim 19 wherein the water miscible solvent comprises ethyl alcohol.
Claim 25
Dependent Claim
14 words
A method as recited in claim 21 wherein the water immiscible solvent comprises xylene.
Claim 26
Dependent Claim
25 words
A method as recited in claim 19 wherein the ratio of tin atoms to silicon atoms in the organotin ethoxysiloxane is less than about 2:5.
Claim 27
Dependent Claim
13 words
A method as recited in claim 19 wherein the organotin radical comprises tributyltin.
Claim 28
Independent Claim
82 words
A method for preparing a solution containing hydrolyzed organotin siloxane polymeric material comprising the steps of: combining a trisubstituted-organotin ethoxysiloxane in which the ratio of tin atoms to silicon atoms in the organotin ethoxysiloxane is in the range of from about 1:50 to 1:1, and a water miscible solvent; gradually adding water and a source of hydrogen ion for hydrolyzing the organotin ethoxysiloxane; adding a water immiscible solvent; and removing by distillation the water miscible solvent and ethyl alcohol from such hydrolysis.
Claim 29
Independent Claim
82 words
A method for preparing a solution containing hydrolyzed organotin siloxane polymeric material comprising the steps of: combining a trisubstituted-organotin ethoxysiloxane in which the ratio of tin atoms to silicon atoms in the organotin ethoxysiloxane is in the range of from about 1:50 to 1:1, and a water miscible solvent; gradually adding water and a source of hydrogen ion for hydrolyzing the organotin ethoxysiloxane; adding a water immiscible solvent; and removing by distillation the water miscible solvent and ethyl alcohol from such hydrolysis.
Claim 30
Dependent Claim
19 words
A method as recited in claim 25 wherein sufficient water is added for substantially completely hydrolyzing the organotin ethoxysiloxane.
Claim 31
Dependent Claim
14 words
A method as recited in claim 25 wherein the water miscible solvent comprises xylene.
Claim 32
Dependent Claim
14 words
A method as recited in claim 25 wherein the water immiscible solvent comprises xylene.
Claim 33
Dependent Claim
25 words
A method as recited in claim 25 wherein the ratio of tin atoms to silicon atoms in the organotin ethoxysiloxane is less than about 2:5.
Claim 34
Dependent Claim
13 words
A method as recited in claim 25 wherein the organotin radical comprises tributyltin.
Claim 35
Independent Claim
118 words
A method for preparing a solution containing hydrolyzed organotin siloxane polymeric material comprising the steps of: reacting sufficient ethoxysiloxane and a trisubstituted tin compound selected from the group consisting of tributyltin acetate and bis-tributyltin oxide for forming a precursor in which the ratio of tin atoms to silicon atoms is in the range of from about 1:50 to 1:1; dissolving the precursor in ethyl alcohol; adding water and a source of hydrolysis catalyst selected from the group consisting of hydrogen ion and hydroxyl ion to the precursor solution for forming a hydrolyzed prepolymer in solution in ethyl alcohol; adding a water immiscible solvent to the solution of prepolymer in ethyl alcohol; and removing the ethyl alcohol by distillation.
Claim 36
Independent Claim
118 words
A method for preparing a solution containing hydrolyzed organotin siloxane polymeric material comprising the steps of: reacting sufficient ethoxysiloxane and a trisubstituted tin compound selected from the group consisting of tributyltin acetate and bis-tributyltin oxide for forming a precursor in which the ratio of tin atoms to silicon atoms is in the range of from about 1:50 to 1:1; dissolving the precursor in ethyl alcohol; adding water and a source of hydrolysis catalyst selected from the group consisting of hydrogen ion and hydroxyl ion to the precursor solution for forming a hydrolyzed prepolymer in solution in ethyl alcohol; adding a water immiscible solvent to the solution of prepolymer in ethyl alcohol; and removing the ethyl alcohol by distillation.
Claim 37
Dependent Claim
24 words
A method as recited in claim 31 wherein the water immiscible solvent is compatible with a chlorinated rubber binder for a marine antifouling coating.
Claim 38
Dependent Claim
14 words
A method as recited in claim 31 wherein the water immiscible solvent comprises xylene.
Claim 39
Dependent Claim
25 words
A method as recited in claim 34 wherein the ratio of tin atoms to silicon atoms in the organotin ethoxysiloxane is less than about 2:5.
Claim 40
Dependent Claim
17 words
A method as recited in claim 31 wherein the water immiscible solvent is added before the water.
Claim 41
Dependent Claim
47 words
A solution comprising a water immiscible solvent containing a polymeric material consisting essentially of substantially completely hydrolyzed organotin substituted siloxane dissolved in the solvent, where the ratio of tin atoms to silicon atoms in the polymeric material is in the range of from about 1:50 to 2:5.
Claim 42
Dependent Claim
47 words
A solution comprising a water immiscible solvent containing a polymeric material consisting essentially of substantially completely hydrolyzed organotin substituted siloxane dissolved in the solvent, where the ratio of tin atoms to silicon atoms in the polymeric material is in the range of from about 1:50 to 2:5.
Claim 43
Dependent Claim
14 words
A solution as recited in claim 36 wherein the organotin moiety comprises tributyltin radical.
Claim 44
Dependent Claim
14 words
A solution as recited in claim 36 wherein the water immiscible solvent comprises xylene.
Claim 45
Dependent Claim
39 words
A solution comprising xylene containing a substantially completely hydrolyzed polymeric tributyltin substituted siloxane dissolved in the xylene where the ratio of tin atoms to silicon atoms in the siloxane is in the range of from about 1:50 to 2:5.
Claim 46
Dependent Claim
39 words
A solution comprising xylene containing a substantially completely hydrolyzed polymeric tributyltin substituted siloxane dissolved in the xylene where the ratio of tin atoms to silicon atoms in the siloxane is in the range of from about 1:50 to 2:5.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-01-18 | 1985-07-20 | 1986-01-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-01-18 | 1989-07-20 | 1990-01-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-01-18 | 1993-07-20 | 1994-01-19 | $7700.00 | Window Closed / Lapsed |