US3941849A
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Polyethers and method for making the same
Assignee: Aerojet Rocketdyne Holdings Inc
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Filing: 1974-05-10
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Granted: 1976-03-02
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Expires: 1994-05-10
Abstract
Abstract Hydroxy terminated polyethers are obtained by reacting (1) epoxide and oxetane monomers with (2) a telogen at least partially soluble with the monomers, reactive with said monomers and being selected from the group consisting of phenols (3) in admixture therewith as catalysts certain double metal cyanide complexes which preferably had been treated with organic materials like alcohols, ethers, esters and so forth. A feature of the process of the present invention is the preparation of high molecular weight diols, triols, etc. without appreciable end group unsaturation, and the use of certain solvents with particular monomers and catalysts to also achieve these results. The products of the present process are useful as nonionic surface active agents, as lubricants and coolants, as textile sizes, as films for packaging and in the preparation of solid or flexible polyurethanes by reaction with polyisocyanates.
Inventors
- 👤 Robert Johnston Herold
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 02:05
CPC Classifications
C; C08; C08G; C08G65/00; C08G65/02; C08G65/26; C08G65/2642; C08G65/2645; C08G65/2663
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
129 words
The method of making polyethers having at least one terminal hydroxyl group and an average molecular weight of between about 300 and 150,000 which comprises: 1. polymerizing in the liquid state at a temperature of from about 0° to 180°C at least one polymerizable organic cyclic oxide monomer selected from the group consisting of ethylene oxide; 1,2-propylene oxide; 1,2-butene oxide; 1,2-dodecane monoxide; isobutylene monoxide; styrene oxide; 1,2-pentene oxide; isopentene oxide, 1,2-diisobutylene oxide; 1,2-hexene oxide; 1,2-heptene oxide; allyl glycidyl ether; isoheptene oxide; 1,2-octene oxide; 1,2-nonene oxide; 1,2-decene oxide; 1,2-hendecene oxide; methyl glycidyl ether; ethyl glycidyl ether; phenyl glycidyl ether; butadiene monoxide; isoprene monoxide; oxetane, tolyl glycidyl ether; 3,3-dimethyl oxetane; 3-n-nonyl oxetane; 3-allyl-3-methyl oxetane; 3-vinyl-3-methyl oxetane; 1,2-pentadecene oxide; 3,3-diethyl oxetane; 3-ethyl-3-butyl oxetane; 3-chloromethylene oxetane; 3-chloromethyl-3-methyl oxetane and 3-methyl-3-ethyl oxetane with 2.
Claim 2
Independent Claim
129 words
The method of making polyethers having at least one terminal hydroxyl group and an average molecular weight of between about 300 and 150,000 which comprises: 1. polymerizing in the liquid state at a temperature of from about 0° to 180°C at least one polymerizable organic cyclic oxide monomer selected from the group consisting of ethylene oxide; 1,2-propylene oxide; 1,2-butene oxide; 1,2-dodecane monoxide; isobutylene monoxide; styrene oxide; 1,2-pentene oxide; isopentene oxide, 1,2-diisobutylene oxide; 1,2-hexene oxide; 1,2-heptene oxide; allyl glycidyl ether; isoheptene oxide; 1,2-octene oxide; 1,2-nonene oxide; 1,2-decene oxide; 1,2-hendecene oxide; methyl glycidyl ether; ethyl glycidyl ether; phenyl glycidyl ether; butadiene monoxide; isoprene monoxide; oxetane, tolyl glycidyl ether; 3,3-dimethyl oxetane; 3-n-nonyl oxetane; 3-allyl-3-methyl oxetane; 3-vinyl-3-methyl oxetane; 1,2-pentadecene oxide; 3,3-diethyl oxetane; 3-ethyl-3-butyl oxetane; 3-chloromethylene oxetane; 3-chloromethyl-3-methyl oxetane and 3-methyl-3-ethyl oxetane with 2.
Claim 3
Dependent Claim
336 words
at least one telogen selected from the group consisting of phenol; p-monochlorophenol; p-cresol; thymol; xylenol; hydroquinone; resorcinol; phloroglucinol; o-, m- or p-hydroxy styrene; saligenin; bisphenol A; bisphenol F; 4,4'-dihydroxy diphenyl; 4,4'-dihydroxy diphenyl sulfone; 4,6,4'-trihydroxy diphenyl dimethyl methane; and long chain bisphenols and novolac resins of molecular weight up to 4000 having a plurality of OH groups; in admixture with 3. a double metal cyanide complex catalyst in an amount of from 0.001 to 15% by weight of said monomer, said catalyst having the general formula: M a (K) c .(H 2 O) d .(R) e where K is selected from the group consisting of: M'(cn) b and M'[(CN) r (X) t ] b where M is at least one metal selected from the group consisting of Zn(II), Fe(II), Fe(III), Co(II), Ni(II), Mo(IV), Mo(VI), Al(III), V(IV), V(V), Sr(II), W(IV), W(VI), Mn(II) and Cr(III), where M' is at least one metal selected from the group consisting of Fe(II), Fe(III), Co(II), Co(III), Cr(II), Cr(III), Mn(II), Mn(III), V(IV), and V(V), where X is at least one material selected from the group consisting of F - , Cl - , Br - , I - , OH - , NO, O = , CO, H 2 O, NO 2 - , C 2 O 4 = , SO 4 = , CNO - , CNS - , NCO - , and NCS - , where R is an organic material containing 1 to 18 carbon atoms substantially water miscible selected from the group consisting of alcohols, aldehydes, ketones, esters, ethers, amides, nitriles and sulfides, where a, b, and c are numbers whose values are functions of the valences and coordination numbers of M and M' with the total net positive charge on M times a being essentially equal to the total negative charge on (K) times c, where r and t are numbers, r being greater than t. where d is zero or a number, and where e is zero or a number sufficient to increase the activity of M a
Claim 4
Dependent Claim
336 words
at least one telogen selected from the group consisting of phenol; p-monochlorophenol; p-cresol; thymol; xylenol; hydroquinone; resorcinol; phloroglucinol; o-, m- or p-hydroxy styrene; saligenin; bisphenol A; bisphenol F; 4,4'-dihydroxy diphenyl; 4,4'-dihydroxy diphenyl sulfone; 4,6,4'-trihydroxy diphenyl dimethyl methane; and long chain bisphenols and novolac resins of molecular weight up to 4000 having a plurality of OH groups; in admixture with 3. a double metal cyanide complex catalyst in an amount of from 0.001 to 15% by weight of said monomer, said catalyst having the general formula: M a (K) c .(H 2 O) d .(R) e where K is selected from the group consisting of: M'(cn) b and M'[(CN) r (X) t ] b where M is at least one metal selected from the group consisting of Zn(II), Fe(II), Fe(III), Co(II), Ni(II), Mo(IV), Mo(VI), Al(III), V(IV), V(V), Sr(II), W(IV), W(VI), Mn(II) and Cr(III), where M' is at least one metal selected from the group consisting of Fe(II), Fe(III), Co(II), Co(III), Cr(II), Cr(III), Mn(II), Mn(III), V(IV), and V(V), where X is at least one material selected from the group consisting of F - , Cl - , Br - , I - , OH - , NO, O = , CO, H 2 O, NO 2 - , C 2 O 4 = , SO 4 = , CNO - , CNS - , NCO - , and NCS - , where R is an organic material containing 1 to 18 carbon atoms substantially water miscible selected from the group consisting of alcohols, aldehydes, ketones, esters, ethers, amides, nitriles and sulfides, where a, b, and c are numbers whose values are functions of the valences and coordination numbers of M and M' with the total net positive charge on M times a being essentially equal to the total negative charge on (K) times c, where r and t are numbers, r being greater than t. where d is zero or a number, and where e is zero or a number sufficient to increase the activity of M a
Claim 5
Dependent Claim
26 words
(K) c .H 2 O for the polymerization of said monomer. 2. The method of claim 1 wherein said temperature is from about 15° to 80°C.
Claim 6
Dependent Claim
33 words
The method of claim 1 wherein said polymerization is conducted in the presence of a solvent for said monomer selected from the group consisting of tetrahydrofuran; 1,2-dimethoxyethane; methyl tetrahydrofuran; dioxane; benzene and hexane.
Claim 7
Dependent Claim
18 words
The method of claim 1 wherein said catalyst is a zinc hexacyanocobaltate complex with glyme, digylme or triglyme.
Claim 8
Dependent Claim
11 words
The method of claim 1 wherein the monomer is propylene oxide.
Claim 9
Dependent Claim
11 words
The method of claim 1 wherein the telogen is bisphenol A.
Claim 10
Dependent Claim
10 words
The method of claim 1 wherein the telogen is resorcinol.
Claim 11
Dependent Claim
27 words
The method of claim 1 wherein the polymerization is conducted in a closed vessel under pressure sufficient to maintain said monomer and telogen in the liquid state.
Claim 12
Dependent Claim
14 words
The method of claim 8 wherein the temperature is from about 15° to 80°C.
Claim 13
Dependent Claim
14 words
The method of claim 9 wherein the reaction mixture is agitated during the polymerization.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-03-02 | 1979-09-01 | 1980-03-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-03-02 | 1983-09-01 | 1984-03-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-03-02 | 1987-09-01 | 1988-03-02 | $7700.00 | Window Closed / Lapsed |