US3676477A
Expired / Lapsed
US
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Esters of pentavalent and trivalent antimony with a polyhydroxy compound and the process for making the same
Assignee: EIDP Inc
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Filing: 1970-11-30
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Granted: 1972-07-11
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Expires: 1990-11-30
Abstract
Abstract Esters of pentavalent antimony (Sb 5) with polyhydroxy compounds having vicinal hydroxyl groups, and mixed esters composed of these pentavelent antimony esters in combination with trivalent antimony (Sb 5) esters of polyhydroxy compounds having vicinal hydroxyl groups, which can be made by a process involving reacting antimony trioxide (Sb2O3) with a polyhydroxy compound having vicinal hydroxyl groups and hydrogen peroxide to oxidize at least a portion of the antimony to the pentavalent state. By removing substantially all of the water of reaction there can be produced a pentavalent antimony ester in which four of the valences of the antimony are satisfied by ester linkages through the hydroxyl groups of two molecules of the polyhydroxy compound and the fifth valence of the antimony is satisfied by an ester linkage through a vicinal hydroxyl group of a third molecule of the polyhydroxy compound. The products of the invention are soluble in polar organic solvents customarily used in processing organic polymers and can therefore be conveniently incorporated into polymers to provide increased flame resistance.
Inventors
- 👤 Dong M Chay
- 👤 Charles Carmen Cumbo
- 👤 Michael J Randolph
- 👤 Paul C Yates
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 16:14
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/90; C07F9/902; C08; C08K; C08K5/00; C08K5/59
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
76 words
An ester of pentavalent antimony with a polyhydroxy compound containing two through six carbon atoms and having vicinal hydroxyl groups, four of the valences of the antimony being satisfied by ester linkages between the antimony and the vicinal hydroxyl groups of two molecules of the polyhydroxy compound, and the fifth valence of the antimony being satisfied by an ester linkage between the antimony and a vicinal hydroxyl group of a third molecule of the polyhydroxy compound.
Claim 2
Dependent Claim
56 words
heating the mixture to a temperature in the range of about 125* to 240* C. to cause reaction of the antimony trioxide with the polyhydroxy compound, with removal of the water of reaction by distillation, whereby there is formed a solution of an ester of trivalent antimony with the polyhydroxy compound, dissolved in excess polyhydroxy compound;
Claim 3
Dependent Claim
51 words
heating the mixture to a temperature in the range of about 135*-180* C. to cause reaction of the antimony trioxide with the diol, with removal of the water of reaction by distillation, whereby there is formed a solution of an ester of trivalent antimony with the diol, dissolved in excess diol;
Claim 4
Dependent Claim
72 words
adding hydrogen peroxide to the solution while maintaining a temperature in the range of about 90* to 170* C. to oxidize at least 60 mole percent of the antimony to the pentavalent state, with removal of water of reaction by distillation under reduced pressure, whereby there is formed a solution of an ester of pentavalent antimony or a mixed ester of trivalent and pentavalent antimony with the diol, dissolved in excess diol;
Claim 5
Dependent Claim
74 words
adding hydrogen peroxide to the solution while maintaining a tempeRature in the range of about 25* to 200* C. to oxidize at least 20 mole percent of the antimony to the pentavalent state, with removal of water of reaction by distillation under reduced pressure, whereby there is formed a solution of an ester of pentavalent antimony or a mixed ester of trivalent and pentavalent antimony with the polyhydroxy compound, dissolved in excess polyhydroxy compound.
Claim 6
Dependent Claim
17 words
An ester of claim 2 in which the mole ratio of polyhydroxy compound to antimony is 3:1.
Claim 7
Dependent Claim
13 words
An ester of claim 3 in which the polyhydroxy compound is ethylene glycol.
Claim 8
Dependent Claim
20 words
removing excess diol by distillation under reduced pressure, until the pentavalent antimony ester of the diol crystallizes from the solution.
Claim 9
Dependent Claim
5 words
A compound of the formula:
Claim 10
Dependent Claim
8 words
A solid compound of claim 5 which is:
Claim 11
Dependent Claim
44 words
A solution of at least one ester of claim 2 in a polar organic solvent having a dielectric constant measured at 25* C. and 104 to 105 cps. greater than 35 ESU and a ratio of carbon atoms to hetero atoms less than 1.7.
Claim 12
Dependent Claim
34 words
A solution of claim 7 in which the solvent is one or more members of the group consisting of formic acid, formamide, methylformamide, dimethylformamide, acetamide, ethylene glycol, glycerol, diethylene glycol, 1,3-propanediol, 1,2-propanediol and dimethylsulfoxide.
Claim 13
Dependent Claim
15 words
A solution of claim 7 in which the solvent is selected from dimethylformamide and dimethylsulfoxide.
Claim 14
Dependent Claim
49 words
A solution of a compound of claim 6 in dimethylformamide having an NMR spectrum with a singlet at 3.70 delta where delta , in parts per million, is defined by the equation where Delta is the distance of the absorption peak from that of tetramethylsilane in cycles per second.
Claim 15
Dependent Claim
177 words
A mixed ester composed of: a. an ester of pentavalent antimony with a polyhydroxy compound containing two through six carbon atoms and having vicinal hydroxyl groups, four of the valences of the antimony being satisfied by ester linkages between the antimony and the vicinal hydroxyl groups of two molecules of the polyhydroxy compound and the fifth valence of the antimony being satisfied by an ester linkage between the antimony and the vicinal hydroxyl group of a third molecule of the polyhydroxy compound and b. an ester of trivalent antimony with a polyhydroxy compound containing two through six carbon atoms and having vicinal hydroxyl groups, two of the valences of the antimony being satisfied by an ester linkage between the antimony and the vicinal hydroxyl groups of one molecule of the polyhydroxy compound and the third valence of the antimony being satisfied by an ester linkage between the antimony and a vicinal hydroxyl group of a second molecule of the polyhydroxy compound, the mole ratio of trivalent to pentavalent antimony in the mixed ester being less than 4:1.
Claim 16
Dependent Claim
22 words
A mixed ester of claim 11 wherein the ratio of trivalent to pentavalent antimony in the mixed ester is less than 2:1.
Claim 17
Dependent Claim
11 words
A mixed ester composed of: a. a compound of the formula:
Claim 18
Dependent Claim
44 words
A solution of at least one mixed ester of claim 11 in a polar organic solvent having a dielectric constant measured at 25* C. and 104 to 105 cps. greater than 35 ESU and the ratio of carbon atoms to heteroatoms less than 1.7.
Claim 19
Dependent Claim
34 words
A solution of claim 14 in which the solvent is one or more members of the group consisting of formic acid, formamide, methylformamide, dimethylformate, acetamide, ethylene glycol, glycerol, diethylene glycol, 1,3-propanediol, 1,2-propanediol and dimethylsulfoxide.
Claim 20
Dependent Claim
15 words
A solution of claim 14 in which the solvent is selected from dimethylformamide and dimethylsulfoxide.
Claim 21
Independent Claim
224 words
A method of making a composition of matter consisting essentially of: a. an ester of pentavalent antimony with a polyhydroxy compound containing two through six carbon atoms and having vicinal hydroxyl groups, four of the valences of the antimony being satisfied by ester linkages between the antimony and the vicinal hydroxyl groups of two molecules of the polyhydroxy compounds and the fifth valence of the antimony being satisfied by an ester linkage between the antimony and a vicinal hydroxyl group of a third molecule of the polyhydroxy compound, in combination with b. an ester of trivalent antimony with a polyhydroxy compound containing two through six carbon atoms and having vicinal hydroxyl groups, two of the valences of the antimony being satisfied by an ester linkage between the antimony and the vicinal hydroxyl groups of one molecule of the polyhydroxy compound, and the third valence of the antimony is satisfied by an ester linkage between the antimony and a second molecule of the polyhydroxy compound, the proportion of the pentavalent antimony ester in the composition being 20-100 mole percent, which comprises adding hydrogen peroxide to either (1) a slurry of antimony trioxide in the aliphatic polyhydroxy compound or (2) a solution of an ester of trivalent antimony with the polyhydroxy compound and oxidizing at least 20 mole percent of the antimony to the pentavalent state.
Claim 22
Dependent Claim
23 words
Method of claim 17 wherein the hydrogen peroxide is added to a solution of an ester of trivalent antimony with the polyhydroxy compound.
Claim 23
Dependent Claim
47 words
Method of claim 18 wherein the hydrogen peroxide is added to the solution maintained at a temperature in the range of 25* to 200* C., and water is removed by distillation, whereby there is formed a solution of the ester or mixed esters in excess polyhydroxy compound.
Claim 24
Dependent Claim
14 words
A method of making a solution of the composition of claim 1 which comprises:
Claim 25
Dependent Claim
35 words
Method of claim 20 wherein the temperature in step (2) is in the range of 135* to 180* C. and the temperature in step (3 ) is in the range of 90* to 170* C.
Claim 26
Dependent Claim
14 words
A method of making a solution of an ester of claim 2 which comprises:
Claim 27
Dependent Claim
19 words
Method of claim 21 wherein the polyhydroxy compound is selected from the group consisting of ethylene glycol and glycerol.
Claim 28
Dependent Claim
10 words
Method of claim 22 wherein the diol is ethylene glycol.
Claim 29
Dependent Claim
19 words
Method of claim 24 wherein in step (3) substantially all of the antimony is oxidized to the pentavalent state.
Claim 30
Dependent Claim
28 words
Method of claim 25 wherein in step (4) the crystallized slurry is diluted with tetrahydrofuran and the crystallized product is recovered by filtration, washed with tetrahydrofuran, and dried.
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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) | 1975-07-11 | 1976-01-10 | 1976-07-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1979-07-11 | 1980-01-10 | 1980-07-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1983-07-11 | 1984-01-10 | 1984-07-11 | $7700.00 | Window Closed / Lapsed |