US3900518A
Expired / Lapsed
US
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Hydroxyl or thiol terminated telomeric ethers
Assignee: Aerojet Rocketdyne Holdings Inc
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Filing: 1973-12-10
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Granted: 1975-08-19
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Expires: 1993-12-10
Abstract
Abstract Hydroxyl or thiol terminated alkylene ether telomers varying from liquids to thermoplastic solids and composed of one or more telomer moieties from cyclic ether taxogen joined through a carbon atom to a telogen moiety are prepared by telomerization of cyclic ether monomer with a primary or secondary aromatic amine as a telogen in the presence of catalyst of the double metal cyanide complex class. As a specific example, a hydroxyl terminated telomer is prepared by telomerization of propylene oxide with aniline using zinc hexacyanoferrate-diglyme complex as the telomerization catalyst.
Inventors
- 👤 Jack Milgrom
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 10:14
CPC Classifications
C; C08; C08G; C08G65/00; C08G65/02; C08G65/26; C08G65/2618; C08G65/2621; C08G65/2627; C08G18/00; C08G18/06; C08G18/28; C08G18/40; C08G18/48; C08G18/4866; C08G65/04; C08G65/06; C08G65/16; C08G65/2642; C08G65/2645; C08G65/2663; C08G75/00; C08G75/02; C08G75/06; C08G75/26
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
240 words
A PROCESS FOR THE PRODUCTION OF HYDROXYL OR THIOL TERMINATED ALKYLENE ETHER TELOMERS HAVING AN AVERAGE MOLECULAR WEIGHT BETWEEN 300 AND 10,000 WHICH COMPRISES TELOMERIZING POLYMERIZABLE CYCLIC ETHER SELECTED FROM THE GROUP CONSISTING OF ETHYLENE OXIDE, 1,2-PROPYLENE OXIDE, 1,2-BUTENE OXIDE, 2,3-BUTENE OXIDE, 1,2-DODECANE MONOXIDE, ISOBUTYLENE MONOXIDE, 1,2-PENTENE OXIDE, ISOPENTENE OXIDE, 1,2-DIISOBUTYLENE OXIDE, 1,2-HEXENE OXIDE, 1,2-HEPTENE OXIDE, ALLY GLYCIDYL ETHER, CROTYL GLYCIDYL ETHER, ISOHEPTONE OXIDE, 1,2-OCETENE OXIDE, 1,2-NONENE OXIDE, STYRENE OXIDE, 1,2-DECENE OXIDE, 1,2-HENDECENE OXIDE, METHYL GLYCIDYL ETHER, ETHYL GLYCIDYL ETHER, PROPL, GLYDICYL ETHER, PHENYL GLYCIDYL ETHER 4-CHLORO PHENYL GLYCIDYL ETHER, BUTADIENE MONOXIDE, ISOPRENE MONOXIDE, OXETANE (C3H6O), TOLYL GLYCIDYL ETHER, 3,3-DIMETHYL OXETANE, 3-N-NONYL OXETANE, 3-ALLYL-3-METHYL OXETANE,3-VINYL3METHYL OXETANE, 1,2-PENTADECENE OXIDE, 3,3-DIETHYL OXETANE, 3-ETHYL-3-BUTYL OXETANE, 3-CHLOROMETHYLENE OXETANE, 3CHLOROMETHYL-3-METHYL OXETANE, 3-METHYL-3ETHYL OXETANE, 4,5-EPITHIO-1-PENTENE: 5,6-EPITHIO-1-HEXENE: 5,L -EPTHIO-2HEXANE: 9,10-EPTHIO-1-DECENE: 7,,-EPTHIO-2-METHYL-1OCTENE: 1,2-EPTHIO-1''-(2-CYCLOPENTEN-1-Y) ETHANE: 3-ALLOYLOXY1,2-EPTHIO PROPANE: 3-(2-BUTENYLOXY)-1,2-EPTHIO PROPANE: 1,2-EPTHIO-1-(3-CYCLOHEXEN-1-Y)ETHANE: 3-(1-METHYL ALLYLOXY)-1,2-EPTHIO PROPANE: 3-(1-MEHTYL-2-BUTENYLOXY)-1,2EPITHIO PROPANE: 3-(2-CYCLOHEXEN-1-YLOXY)-1,2-EPITHIO PROPANE: 3-(3-METHYL-4-HEXENYLOXY)-1,2-EPITHIO PRO-: ETHYLENE SULFIDE: 2,3-EPITHIO BUTANE: 1,2-PROPYLENE SULFIDE: CYCLOHEXENE SULFIDE: ISOBUTYLENE SULFIDE: STYRENE SULFIDE: VINYL THIIRONE: 1,2-OCTENE EPISULFIDE: CROTYL OXY-1,2-EPITHIO PROPANE: I-BUTENE SULFIDE: 2,3-DIMETHYL-2-BUTENE SULFIDE: 3,3-DIMETHYL THIOCYCLOBUTANE: 3-CHLOROPROPENE SULFIDE: THIOCYCLOBUTANE: ALLY THIO-1,2-EPOXY PROPANE: 3-(1-CHLORO-4-BUTENYLOXY)-1,2EPITHIO PROPANE: 3-(1-BROMO-4-BUTENYL)-1,2-EPITHIO PROPANE: 3-(1FLUORO-4-BUTENYL THIO)-1,2-EPITHIO PROPANE: AND 3-(1IODO-4-HEXENYL THIO)-1,2-EPOXY PROPANE, AND MIXTURES THEREOF, WITH A TELOGEN SELECTED FROM THE GROUP CONSISTING OF ANILINE, N-ALKYL ANILINES, P-PHENYLENE DIAMINE, P-ANIMOPHENOL, P-METHYL ANILINE, M-CHLORO ANILINE, O-HEXLY ANILINE, P-IODOANILINE, M-BROMOANILINE, 2-METHYL-4-CHLOROANILINE, 4-(P-AMINOPHENYL) BUTANOL, N-PHENYL HEXAMETHYLENE DIAMINE, N-(P-TOLYL) DIETHYLENE TRIAMINE, NAPHTHYLAMINE, NPHENYL-N'' -NAPHTHYL ETHYLENE DIAMINE AND N-NAPHTHYL-N''HYDROXY HEXAMETHYLENE DIAMINE, IN THE PRESENCE OF A CATALYTIC AMOUNT OF A DOUBLE METAL CYANIDE COMPLEX CATYLST.
Claim 2
Dependent Claim
240 words
A PROCESS FOR THE PRODUCTION OF HYDROXYL OR THIOL TERMINATED ALKYLENE ETHER TELOMERS HAVING AN AVERAGE MOLECULAR WEIGHT BETWEEN 300 AND 10,000 WHICH COMPRISES TELOMERIZING POLYMERIZABLE CYCLIC ETHER SELECTED FROM THE GROUP CONSISTING OF ETHYLENE OXIDE, 1,2-PROPYLENE OXIDE, 1,2-BUTENE OXIDE, 2,3-BUTENE OXIDE, 1,2-DODECANE MONOXIDE, ISOBUTYLENE MONOXIDE, 1,2-PENTENE OXIDE, ISOPENTENE OXIDE, 1,2-DIISOBUTYLENE OXIDE, 1,2-HEXENE OXIDE, 1,2-HEPTENE OXIDE, ALLY GLYCIDYL ETHER, CROTYL GLYCIDYL ETHER, ISOHEPTONE OXIDE, 1,2-OCETENE OXIDE, 1,2-NONENE OXIDE, STYRENE OXIDE, 1,2-DECENE OXIDE, 1,2-HENDECENE OXIDE, METHYL GLYCIDYL ETHER, ETHYL GLYCIDYL ETHER, PROPL, GLYDICYL ETHER, PHENYL GLYCIDYL ETHER 4-CHLORO PHENYL GLYCIDYL ETHER, BUTADIENE MONOXIDE, ISOPRENE MONOXIDE, OXETANE (C3H6O), TOLYL GLYCIDYL ETHER, 3,3-DIMETHYL OXETANE, 3-N-NONYL OXETANE, 3-ALLYL-3-METHYL OXETANE,3-VINYL3METHYL OXETANE, 1,2-PENTADECENE OXIDE, 3,3-DIETHYL OXETANE, 3-ETHYL-3-BUTYL OXETANE, 3-CHLOROMETHYLENE OXETANE, 3CHLOROMETHYL-3-METHYL OXETANE, 3-METHYL-3ETHYL OXETANE, 4,5-EPITHIO-1-PENTENE: 5,6-EPITHIO-1-HEXENE: 5,L -EPTHIO-2HEXANE: 9,10-EPTHIO-1-DECENE: 7,,-EPTHIO-2-METHYL-1OCTENE: 1,2-EPTHIO-1''-(2-CYCLOPENTEN-1-Y) ETHANE: 3-ALLOYLOXY1,2-EPTHIO PROPANE: 3-(2-BUTENYLOXY)-1,2-EPTHIO PROPANE: 1,2-EPTHIO-1-(3-CYCLOHEXEN-1-Y)ETHANE: 3-(1-METHYL ALLYLOXY)-1,2-EPTHIO PROPANE: 3-(1-MEHTYL-2-BUTENYLOXY)-1,2EPITHIO PROPANE: 3-(2-CYCLOHEXEN-1-YLOXY)-1,2-EPITHIO PROPANE: 3-(3-METHYL-4-HEXENYLOXY)-1,2-EPITHIO PRO-: ETHYLENE SULFIDE: 2,3-EPITHIO BUTANE: 1,2-PROPYLENE SULFIDE: CYCLOHEXENE SULFIDE: ISOBUTYLENE SULFIDE: STYRENE SULFIDE: VINYL THIIRONE: 1,2-OCTENE EPISULFIDE: CROTYL OXY-1,2-EPITHIO PROPANE: I-BUTENE SULFIDE: 2,3-DIMETHYL-2-BUTENE SULFIDE: 3,3-DIMETHYL THIOCYCLOBUTANE: 3-CHLOROPROPENE SULFIDE: THIOCYCLOBUTANE: ALLY THIO-1,2-EPOXY PROPANE: 3-(1-CHLORO-4-BUTENYLOXY)-1,2EPITHIO PROPANE: 3-(1-BROMO-4-BUTENYL)-1,2-EPITHIO PROPANE: 3-(1FLUORO-4-BUTENYL THIO)-1,2-EPITHIO PROPANE: AND 3-(1IODO-4-HEXENYL THIO)-1,2-EPOXY PROPANE, AND MIXTURES THEREOF, WITH A TELOGEN SELECTED FROM THE GROUP CONSISTING OF ANILINE, N-ALKYL ANILINES, P-PHENYLENE DIAMINE, P-ANIMOPHENOL, P-METHYL ANILINE, M-CHLORO ANILINE, O-HEXLY ANILINE, P-IODOANILINE, M-BROMOANILINE, 2-METHYL-4-CHLOROANILINE, 4-(P-AMINOPHENYL) BUTANOL, N-PHENYL HEXAMETHYLENE DIAMINE, N-(P-TOLYL) DIETHYLENE TRIAMINE, NAPHTHYLAMINE, NPHENYL-N'' -NAPHTHYL ETHYLENE DIAMINE AND N-NAPHTHYL-N''HYDROXY HEXAMETHYLENE DIAMINE, IN THE PRESENCE OF A CATALYTIC AMOUNT OF A DOUBLE METAL CYANIDE COMPLEX CATYLST.
Claim 3
Dependent Claim
98 words
The process of claim 1 wherein said catalyst is material having the general formula Ma(M''(CN)b)c where a, b and c are numbers whose values are functions of the valences and coordination numbers of M and M'', where M is metal selected from the group consisting of zinc (II), iron (II), cobalt (II) and iron (II), and M'' is metal selected from the group consisting of iron (II), iron (III), cobalt (III) and chronium (III) and complexes said material with a substantially water-soluble saturated acyclic aliphatic polyether free of active hydrogen having a molecular weight up to about 400.
Claim 4
Dependent Claim
55 words
The process of claim 1 wherein said catalyst is selected from the group consisting of zinc hexacyanoferrate (III), zinc hexacyanoferrate (II), nickel (II) hexacyanoferrate (II), nickel (II) hexacyanoferrate (III), zinc hexacyanoferrate (III) hydrate, cobalt (II) hexacyanoferrate (II), nickel (II) hexacyanoferrate (III) hydrate, ferrous hexacyanoferrate (III), cobalt (II) hexacyanocobaltate (III), zinc hexacyanochromate (III) and mixtures thereof.
Claim 5
Dependent Claim
17 words
The process of claim 3 wherein said oxide is propylene oxide and said amine is p-phenylene diamine.
Claim 6
Dependent Claim
39 words
The process of claim 3 wherein said oxide is selected from the group consisting of ethylene oxide, propylene oxide, allyl glycidyl ether, crotyl glycidyl ether, 1,2-butene oxide, phenyl glycidyl ether, styrene oxide, ethyl glycidyl ether and propyl glycidyl ether.
Claim 7
Dependent Claim
85 words
A process for the production of hydroxyl terminated alkylene ether telomers having an average molecular weight between about 300 and 10,000 by reacting polymerizable cyclic ether selected from the group consisting of ethylene oxide; propylene oxide; allyl glycidyl ether; crotyl glycidyl ether; 1,2-butene oxide; phenyl glycidyl ether; styrene oxide; ethyl glycidyl ether and propyl glycidyl ether with an amine selected from the group consisting of aniline, N-ethyl aniline and p-phenylene diamine in the presence of a catalytic amount of a double metal cyanide complex catalyst.
Claim 8
Dependent Claim
85 words
A process for the production of hydroxyl terminated alkylene ether telomers having an average molecular weight between about 300 and 10,000 by reacting polymerizable cyclic ether selected from the group consisting of ethylene oxide; propylene oxide; allyl glycidyl ether; crotyl glycidyl ether; 1,2-butene oxide; phenyl glycidyl ether; styrene oxide; ethyl glycidyl ether and propyl glycidyl ether with an amine selected from the group consisting of aniline, N-ethyl aniline and p-phenylene diamine in the presence of a catalytic amount of a double metal cyanide complex catalyst.
Claim 9
Dependent Claim
132 words
A process for the production of hydroxyl terminated alkylene ether telomers having an average molecular weight between about 300 and 10,000 by telomerizing a polymerizable cyclic ether selected from the group consisting of ethylene oxide; propylene oxide; allyl glycidyl ether; crotyl glycidyl ether; 1,2-butene oxide; phenyl glycidyl ether; styrene oxide; ethyl glycidyl ether and propyl glycidyl ether with an amine selected from the group consisting of aniline, N-ethyl aniline and p-phenylene diamine in the presence of a catalytic amount of a double metal cyanide complex catalyst selected from the group consisting of zinc hexacyanoferrate (III), zinc hexacyanoferrate (II), nickel (II) hexacyanoferrate (II), nickel (II) hexacyanoferrate (III), zinc hexacyanoferrate (III) hydrate, cobalt (II) hexacyanoferrate (II), nickel (II) hexacyanoferrate (III) hydrate, ferrous hexacyanoferrate (III), cobalt (II) hexacyanocobaltate (III), zinc hexacyanochromate (III), and mixtures thereof.
Claim 10
Dependent Claim
132 words
A process for the production of hydroxyl terminated alkylene ether telomers having an average molecular weight between about 300 and 10,000 by telomerizing a polymerizable cyclic ether selected from the group consisting of ethylene oxide; propylene oxide; allyl glycidyl ether; crotyl glycidyl ether; 1,2-butene oxide; phenyl glycidyl ether; styrene oxide; ethyl glycidyl ether and propyl glycidyl ether with an amine selected from the group consisting of aniline, N-ethyl aniline and p-phenylene diamine in the presence of a catalytic amount of a double metal cyanide complex catalyst selected from the group consisting of zinc hexacyanoferrate (III), zinc hexacyanoferrate (II), nickel (II) hexacyanoferrate (II), nickel (II) hexacyanoferrate (III), zinc hexacyanoferrate (III) hydrate, cobalt (II) hexacyanoferrate (II), nickel (II) hexacyanoferrate (III) hydrate, ferrous hexacyanoferrate (III), cobalt (II) hexacyanocobaltate (III), zinc hexacyanochromate (III), and mixtures thereof.
Claim 11
Dependent Claim
60 words
The process of claim 7 wherein the ratio of mols of said cyclic ether to the number of amine groups in said amine is between about 240:1 and 1:1 and the telomerization is conducted at a temperature between about 0* - 100*C under pressure sufficient to maintain the reactants in the liquid state between about 1 to 1000 grams/sq. cm..
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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) | 1978-08-18 | 1979-02-17 | 1979-08-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-08-18 | 1983-02-17 | 1983-08-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-08-18 | 1987-02-17 | 1987-08-19 | $7700.00 | Window Closed / Lapsed |