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US4379894A Expired / Lapsed US ⏱️ 0.0 years remaining

Aqueous process for the quantitative conversion of polyepichlorohydrin to glycidyl azide polymer

Assignee: Boeing North American Inc
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Filing: 1981-12-14
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Granted: 1983-04-12
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Expires: 2001-12-14
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Abstract

Abstract An aqueous process for the quantitative conversion of polyepichlorodrin (PECH) to glycidyl azide polymer (GAP), using a phase transfer catalyst, is disclosed.

Inventors

  • 👤 Milton B. Frankel
  • 👤 Edward F. Witucki
  • 👤 II Dean O. Woolery

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-30 09:32
CPC Classifications
C; C08; C08G; C08G65/00; C08G65/02; C08G65/32; C08G65/321; C08G65/325

Claims Analysis

Total Claims: 22
Claim 1
Independent Claim 165 words
An aqueous process for the quantitative conversion of polyepichlorohydrin (PECH) to glycidyl azide polymer (GAP), comprises the steps of: combining said PECH and an ionic azide in a mixture of water and a phase transfer catalyst capable of the quantitative conversion of PECH to GAP; reacting said PECH and said ionic azide in said aqueous mixture while agitating said mixture at a temperature between about 25° C. and about 100° C., and wherein said aqueous mixture is maintained under a nitrogen purged environment; and recovering said GAP from said aqueous mixture by separating the aqueous layer from the product layer; water-washing said product layer to remove any inorganic salts remaining in the product layer; alcohol-washing said water-washed product layer so as to remove said phase transfer catalyst; dissolving said alcohol-washed product layer in a low-boiling, non-polar solvent; purifying said dissolved product layer by passing it through adsorbents capable of removing impurities; and concentrating said purified product layer so as to remove said low-boiling non-polar solvent.
Claim 2
Dependent Claim 165 words
An aqueous process for the quantitative conversion of polyepichlorohydrin (PECH) to glycidyl azide polymer (GAP), comprises the steps of: combining said PECH and an ionic azide in a mixture of water and a phase transfer catalyst capable of the quantitative conversion of PECH to GAP; reacting said PECH and said ionic azide in said aqueous mixture while agitating said mixture at a temperature between about 25° C. and about 100° C., and wherein said aqueous mixture is maintained under a nitrogen purged environment; and recovering said GAP from said aqueous mixture by separating the aqueous layer from the product layer; water-washing said product layer to remove any inorganic salts remaining in the product layer; alcohol-washing said water-washed product layer so as to remove said phase transfer catalyst; dissolving said alcohol-washed product layer in a low-boiling, non-polar solvent; purifying said dissolved product layer by passing it through adsorbents capable of removing impurities; and concentrating said purified product layer so as to remove said low-boiling non-polar solvent.
Claim 3
Dependent Claim 22 words
The process of claim 1 wherein there is about a 5 to about a 25 percent molar excess of said ionic azide.
Claim 4
Dependent Claim 18 words
The process of claim 2 wherein said molar excess range is from about 10 to about 15 percent.
Claim 5
Dependent Claim 23 words
The process of claim 1 wherein said ionic azide is selected from the group consisting of sodium azide, lithium azide, and potassium azide.
Claim 6
Dependent Claim 12 words
The process of claim 4 wherein said ionic azide is sodium azide.
Claim 7
Dependent Claim 19 words
The process of claim 1 wherein said phase transfer catalysts are selected from the group consisting of tertiary amines.
Claim 8
Dependent Claim 15 words
The process of claim 1 wherein said phase transfer catalyst is methyl tricapryl ammonium chloride.
Claim 9
Dependent Claim 20 words
The process of claim 1 wherein said phase transfer catalyst is selected from the group consisting of quaternary ammonium compounds.
Claim 10
Dependent Claim 27 words
The process of claim 1 wherein the excess of said phase transfer catalyst is from about 5 to about 25 weight percent as related to said polyepichlorohydrin.
Claim 11
Dependent Claim 22 words
The process of claim 8 wherein the excess of said phase transfer catalyst is from about 10 to about 20 weight percent.
Claim 12
Dependent Claim 18 words
The process of claim 1 wherein said temperature is maintained between about 80° C. and about 100° C.
Claim 13
Dependent Claim 19 words
The process of claim 11 wherein said temperature range is maintained between about 90° C. and about 95° C.
Claim 14
Dependent Claim 12 words
The process of claim 1 wherein said separating is accomplished by decanting.
Claim 15
Dependent Claim 11 words
The process of claim 1 wherein said water-washing is hot water-washing.
Claim 16
Dependent Claim 27 words
The process of claim 1 wherein said alcohol washing is effected with an alcohol selected from the group consisting of isopropyl alcohol, methyl alcohol, and ethyl alcohol.
Claim 17
Dependent Claim 11 words
The process of claim 15 wherein said alcohol is isopropyl alcohol.
Claim 18
Dependent Claim 22 words
The process of claim 1 wherein said low-boiling non-polar solvent is selected from the group consisting of chloroform, carbontetrachloride, and methylene chloride.
Claim 19
Dependent Claim 13 words
The process of claim 17 wherein said low-boiling non-polar solvent is methylene chloride.
Claim 20
Dependent Claim 20 words
The process of claim 1 wherein said adsorbents are selected from the group consisting of silica gel, alumina, and charcoal.
Claim 21
Dependent Claim 11 words
The process of claim 1 wherein said adsorbent is silica gel.
Claim 22
Dependent Claim 13 words
The process of claim 1 wherein said concentrating is effected by vacuum distillation.

References Cited (Backward Citations)

US3645917A Cited
US4268450A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1986-04-11 1986-10-11 1987-04-12 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1990-04-11 1990-10-11 1991-04-12 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1994-04-11 1994-10-11 1995-04-12 $7700.00 Window Closed / Lapsed

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