Patent US4140516A successfully refreshed from Google Patents.
US4140516A
Expired / Lapsed
US
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Encapsulation process employing phase transfer catalysts
Assignee: Zeneca Inc
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Filing: 1977-05-31
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Granted: 1979-02-20
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Expires: 1997-05-31
Abstract
Abstract An improved encapsulation process to prepare encapsulated water-immiscible material employing an organic polyisocyanate intermediate to form discrete polyurea capsule enclosures around a water-immiscible material dispersed in an aqueous continuous phase said improvement comprising the addition of a catalytic amount of a phase transfer catalyst.
Inventors
- 👤 Herbert B. Scher
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 21:29
CPC Classifications
A; A01; A01N; A01N25/00; A01N25/26; A01N25/28; B; B01; B01J; B01J13/00; B01J13/02; B01J13/06; B01J13/14; B01J13/16
Claims Analysis
Total Claims: 48
Claim 1
Independent Claim
213 words
A process for the preparation of encapsulated water-immiscible material within discrete shells of polyurea without external heating which comprises (a) providing in an aqueous phase a solution comprising water, a surfactant and a protective colloid; (b) adjusting the pH of said aqueous phase to about 2 to about 8; (c) adding to said pH adjusted aqueous phase a water-immiscible phase comprising the water-immiscible material to be encapsulated, an organic polyisocyanate and a catalytic amount of an organic quaternary salt phase transfer catalyst having the formula (R.sub.3 R.sub.4 R.sub.5 R.sub.6 M) .sup.+ X .sup.- wherein R 3 , R 4 , R 5 and R 6 are hydrocarbon radicals independently selected from the group consisting of alkyl, alkenyl, aryl, alkaryl aralkyl, and cycloalkyl radicals; M is a member selected from the group consisting of nitrogen, phosphorus, arsenic, antimony, and bismuth; and X is an anion selected from the group consisting of a halide ion and a hydroxyl ion which will dissolve from the cation in an aqueous environment; (d) dispersing said water-immiscible phase in said aqueous phase to establish droplets of the water-immiscible phase in said aqueous phase; (e) adjusting the pH of the dispersion to between about pH 8 and about pH 12; whereupon discrete polyurea capsular enclosure forms around the water-immiscible material.
Claim 2
Dependent Claim
213 words
A process for the preparation of encapsulated water-immiscible material within discrete shells of polyurea without external heating which comprises (a) providing in an aqueous phase a solution comprising water, a surfactant and a protective colloid; (b) adjusting the pH of said aqueous phase to about 2 to about 8; (c) adding to said pH adjusted aqueous phase a water-immiscible phase comprising the water-immiscible material to be encapsulated, an organic polyisocyanate and a catalytic amount of an organic quaternary salt phase transfer catalyst having the formula (R.sub.3 R.sub.4 R.sub.5 R.sub.6 M) .sup.+ X .sup.- wherein R 3 , R 4 , R 5 and R 6 are hydrocarbon radicals independently selected from the group consisting of alkyl, alkenyl, aryl, alkaryl aralkyl, and cycloalkyl radicals; M is a member selected from the group consisting of nitrogen, phosphorus, arsenic, antimony, and bismuth; and X is an anion selected from the group consisting of a halide ion and a hydroxyl ion which will dissolve from the cation in an aqueous environment; (d) dispersing said water-immiscible phase in said aqueous phase to establish droplets of the water-immiscible phase in said aqueous phase; (e) adjusting the pH of the dispersion to between about pH 8 and about pH 12; whereupon discrete polyurea capsular enclosure forms around the water-immiscible material.
Claim 3
Dependent Claim
10 words
The process of claim 1 in which M is nitrogen.
Claim 4
Dependent Claim
11 words
The process of claim 1 in which X is a halide.
Claim 5
Dependent Claim
12 words
The process of claim 2 in which X is chlorine or bromine.
Claim 6
Dependent Claim
10 words
The process of claim 1 in which M is phosphorus.
Claim 7
Dependent Claim
11 words
The process of claim 4 in which X is a halide.
Claim 8
Dependent Claim
12 words
The process of claim 5 in which X is chlorine or bromine.
Claim 9
Dependent Claim
48 words
The process as described in claim 1 in which the organic quaternary salt is selected from the group consisting of tetra-n-butyl phosphonium chloride, tri-n-butyl n-cetyl phosphonium bromide, hexadecyl tributyl phosphonium bromide, benzyl triethyl ammonium chloride, benzyl triethyl ammonium bromide, tricaprylyl methyl ammonium chloride, and dimethyl dicoco ammonium chloride.
Claim 10
Dependent Claim
15 words
The process of claim 1 in which said water-immiscible material is a water-immiscible organic material.
Claim 11
Dependent Claim
25 words
The process of claim 1 wherein the organic phase contains organic polyisocyanate within the range of about 20 percent to about 75.0 percent by weight.
Claim 12
Dependent Claim
13 words
The process of claim 10 wherein said organic polyisocyanate is an aromatic diisocyanate.
Claim 13
Dependent Claim
22 words
The process of claim 11 wherein said aromatic diisocyanate is about 80 percent 2,4- and about 20 percent 2,6-isomer of tolylene diisocyanate.
Claim 14
Dependent Claim
12 words
The process of claim 10 wherein said organic polyisocyanate is aromatic polyisocyanate.
Claim 15
Dependent Claim
12 words
The process of claim 13 wherein said aromatic polyisocyanate is polymethylene polyphenylisocyanate.
Claim 16
Dependent Claim
13 words
The process of claim 10 wherein said organic polyisocyanate is an aliphatic diisocyanate.
Claim 17
Dependent Claim
12 words
The process of claim 15 wherein said aliphatic diisocyanate is hexamethylene diisocyanate.
Claim 18
Dependent Claim
18 words
The process of claim 10 wherein said organic polyisocyanate is a combination of aromatic isocyanate and aliphatic polyisocyanates.
Claim 19
Dependent Claim
19 words
The process of claim 17 wherein said aromatic polyisocyanate is polymethylene polyphenylisocyanate and said aliphatic polyisocyanate is hexamethylene diisocyanate.
Claim 20
Dependent Claim
32 words
The process of claim 9 for encapsulating water-immiscible organic material wherein the organic phase added to the aqueous phase is a combination of organic polyisocyanates, percent to about 75 percent by weight.
Claim 21
Dependent Claim
26 words
The process of claim 19 wherein said combination of organic polyisocyanates consist of polymethylene polyphenylisocyanate and 80 percent 2,4- and 20 percent 2,6-isomers of tolylene diisocyanate.
Claim 22
Dependent Claim
25 words
The process of claim 1 wherein said water-immiscible organic material is a thiocarbamate herbicide whereupon said thiocarbamate herbicide is encapsulated within a polyurea capsular enclosure.
Claim 23
Dependent Claim
22 words
The process of claim 21 for encapsulating water-immiscible organic material within a polyurea capsule wherein said thiocarbamate herbicide is S-ethyl diisobutyl thiocarbamate.
Claim 24
Dependent Claim
22 words
The process of claim 21 for encapsulating a water-immiscible organic material within a polyurea capsule wherein said thiocarbamate herbicide is S-ethyl dipropylthiocarbamate.
Claim 25
Dependent Claim
22 words
The process of claim 21 for encapsulating a water-immiscible organic material within a polyurea capsule wherein said thiocarbamate herbicide is S-ethyl hexahydro-1-H-azepine-1-carbothioate.
Claim 26
Dependent Claim
22 words
The process of claim 21 for encapsulating a water-immiscible organic material within a polyurea capsule wherein said thiocarbamate herbicide is S-propyl dipropylthiocarbamate.
Claim 27
Dependent Claim
22 words
The process of claim 21 for encapsulating a water-immiscible organic material within a polyurea capsule wherein said thiocarbamate herbicide is S-ethyl ethylcyclohexylthiocarbamate.
Claim 28
Dependent Claim
22 words
The process of claim 21 for encapsulating a water-immiscible organic material within a polyurea capsule wherein said thiocarbamate herbicide is S-propyl butylethylthiocarbamate.
Claim 29
Dependent Claim
22 words
The process of claim 21 for encapsulating a water-immiscible organic material within a polyurea capsule wherein said thiocarbamate herbicide is S-propyl hexahydro-1-H-azepine-1-carbothioate.
Claim 30
Dependent Claim
26 words
The process of claim 1 wherein said water-immiscible organic material is an organophosphorus insecticide and whereupon said organophosphorus insecticide is encapsulated within a polyurea capsular enclosure.
Claim 31
Dependent Claim
23 words
The process of claim 29 for encapsulating a water-immiscible organic material within a polyurea capsule wherein said organophosphorus insecticide is O-ethyl S-phenyl ethylphosphonodithioate.
Claim 32
Dependent Claim
23 words
The process of claim 29 for encapsulating a water-immiscible organic material within a polyurea capsule wherein said organophosphorus insecticide is O,O-dimethyl O-p-nitrophenyl phosphorothioate.
Claim 33
Dependent Claim
23 words
The process of claim 29 for encapsulating a water-immiscible organic material within a polyurea capsule wherein said organophosphorus insecticide is O,O-diethyl O-p-nitrophenyl phosphorothioate.
Claim 34
Dependent Claim
23 words
The process of claim 29 for encapsulating a water-immiscible organic material within a polyurea capsule wherein said organophosphorus insecticide is S[(p-chlorophenylthio)methyl] O,O-dimethyl phosphorodithioate.
Claim 35
Dependent Claim
23 words
The process of claim 29 for encapsulating a water-immiscible organic material within a polyurea capsule wherein said organophosphorus insecticide is S[(p-chlorophenylthio)methyl] O,O-diethyl phosphorodithioate.
Claim 36
Dependent Claim
27 words
The process of claim 1 wherein said water-immiscible organic material is an insect hormone mimic whereupon said insect hormone mimic is encapsulated within a polyurea capsular enclosure.
Claim 37
Dependent Claim
22 words
The process of claim 35 for encapsulating a water-immiscible organic material within a polyurea capsule wherein said insect hormone mimic is 1-(4'-ethyl)phenoxy-3,7-dimethyl-6,7-epoxy-trans-2-octene.
Claim 38
Dependent Claim
20 words
The process as described in claim 1 used to encapsulate a mixture of an herbicide and a complimentary antidote therefore.
Claim 39
Dependent Claim
20 words
The process of claim 37 in which the herbicide is S-ethyl diisobutyl thiocarbamate and the complimentary antidote is N,N-diallyl dichloroacetamide.
Claim 40
Dependent Claim
19 words
The process of claim 37 in which the herbicide is S-ethyl dipropylthiocarbamate and the complimentary antidote is N,N-diallyl dichloroacetamide.
Claim 41
Dependent Claim
19 words
The process of claim 37 in which the herbicide is S-propyl dipropylthiocarbamate and the complimentary antidote is N,N-diallyl dichloroacetamide.
Claim 42
Dependent Claim
197 words
A process for the preparation of encapsulated water-immiscible material within discrete shells of polyurea without external heating which comprises (a) providing in an aqueous phase a solution comprising water, a surfactant and a protective colloid; (b) adjusting the pH of said aqueous phase to about 5 to about 10; (c) adding to said pH adjusted aqueous phase a water-immiscible phase comprising the water-immiscible material to be encapsulated, an organic polyisocyanate and a catalytic amount of an organic quaternary salt phase transfer catalyst having the formula (R.sub.3 R.sub.4 R.sub.5 R.sub.6 M) .sup.+ X .sup.- wherein R 3 , R 4 , R 5 and R 6 are hydrocarbon radicals independently selected from the group consisting of alkyl, alkenyl, aryl, alkaryl, aralkyl and cycloalkyl radicals; M is a member selected from the group consisting of nitrogen, phosphorus, arsenic, antimony and bismuth; and X is an anion selected from the group consisting of a halide ion and a hydroxyl ion which will dissolve from the cation in an aqueous environment; (d) dispersing said water-immiscible phase in said aqueous phase to establish droplets of the water-immiscible phase in said aqueous phase; whereupon discrete polyurea capsular enclosure forms around the water-immiscible material.
Claim 43
Dependent Claim
197 words
A process for the preparation of encapsulated water-immiscible material within discrete shells of polyurea without external heating which comprises (a) providing in an aqueous phase a solution comprising water, a surfactant and a protective colloid; (b) adjusting the pH of said aqueous phase to about 5 to about 10; (c) adding to said pH adjusted aqueous phase a water-immiscible phase comprising the water-immiscible material to be encapsulated, an organic polyisocyanate and a catalytic amount of an organic quaternary salt phase transfer catalyst having the formula (R.sub.3 R.sub.4 R.sub.5 R.sub.6 M) .sup.+ X .sup.- wherein R 3 , R 4 , R 5 and R 6 are hydrocarbon radicals independently selected from the group consisting of alkyl, alkenyl, aryl, alkaryl, aralkyl and cycloalkyl radicals; M is a member selected from the group consisting of nitrogen, phosphorus, arsenic, antimony and bismuth; and X is an anion selected from the group consisting of a halide ion and a hydroxyl ion which will dissolve from the cation in an aqueous environment; (d) dispersing said water-immiscible phase in said aqueous phase to establish droplets of the water-immiscible phase in said aqueous phase; whereupon discrete polyurea capsular enclosure forms around the water-immiscible material.
Claim 44
Dependent Claim
48 words
The process as described in claim 41 in which the organic quaternary salt is selected from the group consisting of tetra-n-butyl phosphonium chloride, tri-n-butyl n-cetyl phosphonium bromide, hexadecyl tributyl phosphonium bromide, benzyl triethyl ammonium chloride, benzyl triethyl ammonium bromide, tricaprylyl methyl ammonium chloride, and dimethyl dicoco ammonium chloride.
Claim 45
Dependent Claim
25 words
The process of claim 41 wherein the organic phase contains organic polyisocyanate within the range of about 20 percent to about 75.0 percent by weight.
Claim 46
Dependent Claim
25 words
The process of claim 41 wherein said water-immiscible organic material is a thiocarbamate herbicide whereupon said thiocarbamate herbicide is encapsulated within a polyurea capsular enclosure.
Claim 47
Dependent Claim
26 words
The process of claim 41 wherein said water-immiscible organic material is an organophosphorus insecticide and whereupon said organophosphorus insecticide is encapsulated within a polyurea capsular enclosure.
Claim 48
Dependent Claim
27 words
The process of claim 41 wherein said water-immiscible organic material is an insect hormone mimic whereupon said insect hormone mimic is encapsulated within a polyurea capsular enclosure.
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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) | 1982-02-19 | 1982-08-21 | 1983-02-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-02-19 | 1986-08-21 | 1987-02-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-02-19 | 1990-08-21 | 1991-02-20 | $7700.00 | Window Closed / Lapsed |