US4301083A
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Preparation of etherified polyoxyalkylene derivatives
Assignee: Kuraray Co Ltd
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Filing: 1980-01-02
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Granted: 1981-11-17
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Expires: 2000-01-02
Abstract
Abstract Polyoxyalkylene compounds having at least four oxyalkylene units and one or two terminal hydroxyl groups are etherified by reacting same with organic primary chlorides or bromides in the presence of an aqueous, at least 30% by weight solution of sodium or potassium hydroxide to produce the corresponding etherified polyoxyalkylene derivatives. The molar ratio of the organohalide to the hydroxyl group(s) of the polyoxyalkylene compound is at least 1.2, and the molar ratio of the alkali metal hydroxide to such hydroxyl group(s) is at least 1.
Inventors
- 👤 Noriaki Yoshimura
- 👤 Masuhiko Tamura
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 13:58
CPC Classifications
C; C07; C07C; C07C41/00; C07C41/01; C07C41/16; C07C213/00; C07C213/06; C07C231/00; C07C231/12; C07C43/00; C07C43/02; C07C43/03; C07C43/04; C07C43/10; C07C43/11; C08; C08G; C08G65/00; C08G65/02; C08G65/32; C08G65/329; C08G65/337
Claims Analysis
Total Claims: 36
Claim 1
Independent Claim
277 words
A process for preparing an etherified polyoxyalkylene derivative having the structural formula: ##STR17## wherein m and n are zero or numbers greater than zero, m and n not being both zero, such that m+n≧4; Q is a member selected from the group consisting of --OCH 2 R, --OR 1 , --N(CH 2 R)R 2 , --N(CH 2 R)COR 2 , --NR 2 R 3 , --N(R 3 )COR 2 , ##STR18## R is hydrogen or --CR 4 R 5 R 6 ; R 1 , R 2 and R 3 are the same or different and are each a hydrocarbon; R 4 , R 5 and R 6 are each hydrogen or a hydrocarbon; and p and q are each zero or numbers greater than zero such that p+q>0, which process consists essentially of reacting in a single step a polyoxyalkylene compound having the structural formula: ##STR19## wherein Q' is Q as defined above or a member selected from --OH, --NHR 2 , --NHCOR 2 , ##STR20## and m, n, R 2 , p and q are as previously defined, with an organic halide having the structural formula: R--CH.sub.2 --X [III] wherein X is chlorine or bromine atom and R is as previously defined, in the presence of an aqueous solution of sodium or potassium hydroxide having an initial alkali metal hydroxide concentration of from about 30% to about 75% by weight, and at a molar ratio of the said organic halide to hydroxyl content of the said polyoxyalkylene compound of at least 1.2 and at a molar ratio of the said alkali metal hydroxide to hydroxyl content of the said polyoxyalkylene compound of at least 1.
Claim 2
Dependent Claim
277 words
A process for preparing an etherified polyoxyalkylene derivative having the structural formula: ##STR17## wherein m and n are zero or numbers greater than zero, m and n not being both zero, such that m+n≧4; Q is a member selected from the group consisting of --OCH 2 R, --OR 1 , --N(CH 2 R)R 2 , --N(CH 2 R)COR 2 , --NR 2 R 3 , --N(R 3 )COR 2 , ##STR18## R is hydrogen or --CR 4 R 5 R 6 ; R 1 , R 2 and R 3 are the same or different and are each a hydrocarbon; R 4 , R 5 and R 6 are each hydrogen or a hydrocarbon; and p and q are each zero or numbers greater than zero such that p+q>0, which process consists essentially of reacting in a single step a polyoxyalkylene compound having the structural formula: ##STR19## wherein Q' is Q as defined above or a member selected from --OH, --NHR 2 , --NHCOR 2 , ##STR20## and m, n, R 2 , p and q are as previously defined, with an organic halide having the structural formula: R--CH.sub.2 --X [III] wherein X is chlorine or bromine atom and R is as previously defined, in the presence of an aqueous solution of sodium or potassium hydroxide having an initial alkali metal hydroxide concentration of from about 30% to about 75% by weight, and at a molar ratio of the said organic halide to hydroxyl content of the said polyoxyalkylene compound of at least 1.2 and at a molar ratio of the said alkali metal hydroxide to hydroxyl content of the said polyoxyalkylene compound of at least 1.
Claim 3
Dependent Claim
17 words
The process as defined by claim 1, wherein the polyoxyethylene compound [II] has the structural formula: ##STR21##
Claim 4
Dependent Claim
17 words
The process as defined by claim 1, wherein the polyoxyethylene compound [II] has the structural formula: ##STR22##
Claim 5
Dependent Claim
17 words
The process as defined by claim 1, wherein the polyoxyethylene compound [II] has the structural formula: ##STR23##
Claim 6
Dependent Claim
17 words
The process as defined by claim 1, wherein the polyoxyethylene compound [II] has the structural formula: ##STR24##
Claim 7
Dependent Claim
17 words
The process as defined by claim 1, wherein the polyoxyethylene compound [II] has the structural formula: ##STR25##
Claim 8
Dependent Claim
17 words
The process as defined by claim 1, wherein the polyoxyethylene compound [II] has the structural formula: ##STR26##
Claim 9
Dependent Claim
17 words
The process as defined by claim 1, wherein the polyoxyethylene compound [II] has the structural formula: ##STR27##
Claim 10
Dependent Claim
17 words
The process as defined by claim 1, wherein the polyoxyethylene compound [II] has the structural formula: ##STR28##
Claim 11
Dependent Claim
21 words
The process as defined by claim 1, wherein the values of m and n are within the range, 4≦m+n≦ about 40.
Claim 12
Dependent Claim
19 words
The process as defined by claim 1, wherein the values of m and n are with the range, 6≦m÷n≦25.
Claim 13
Dependent Claim
23 words
The process as defined by claim 1, wherein the values of m, n, p and q are within the range, m+n+p+q≦ about 40.
Claim 14
Dependent Claim
23 words
The process as defined by claim 1, wherein the values of m, n, p and q are within the range m+n+p+q≦ about 25.
Claim 15
Dependent Claim
35 words
The process as defined by claim 1, wherein the hydrocarbon groups R 1 , R 2 , R 3 , R 4 , R 5 and R 6 have from 1 to 20 carbon atoms.
Claim 16
Dependent Claim
71 words
The process as defined by claim 1, wherein each hydrocarbon R 1 , R 2 and R 3 is selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl, n-butyl, n-amyl, isoamyl, n-hexyl, 2-methylpentyl, 2-ethylbutyl, n-heptyl, 2-methylhexyl, 2-ethylpentyl, 2,4-dimethylpentyl, n-octyl, 2-ethylhexyl, nonyl, 3-methyl-5-ethylhexyl, 3,5,5-trimethylhexyl, 2-ethyl-4,4-dimethylpentyl, n-decyl, 2,6-dimethyloctyl, 2,4,6-trimethylheptyl, undecyl, n-dodecyl, 3,5,5-7,7-pentamethyloctyl, 4,6,8-trimethylnonyl, cetyl, stearyl, allyl, pentenyl, decenyl, oleyl, cyclohexyl, methylcyclohexyl, ethylcyclohexyl, phenyl, butylphenyl, nonylphenyl, decylphenyl, undecylphenyl, dodecylphenyl, benzyl, methylbenzyl, and nonylbenzyl.
Claim 17
Dependent Claim
50 words
The process as defined by claim 1, wherein the polyoxyalkylene compoound of the structural formula [II] is a polyoxyethylene compound having from 4 to 20 oxyethylene units and the organic halide of the structural formula [III] is a saturated aliphatic chloride or bromide having from 5 to 18 carbon atoms.
Claim 18
Dependent Claim
14 words
The process as defined by claim 16, wherein the polyoxyethylene compound is polyoxyethylene glycol.
Claim 19
Dependent Claim
20 words
The process as defined by claim 16, wherein the polyoxyethylene compound is a polyoxyethylene compound is a polyoxyethylene glycol monoether.
Claim 20
Dependent Claim
21 words
The process as defined by claim 1, wherein the reaction is carried out in the presence of an inorganic reducing agent.
Claim 21
Dependent Claim
26 words
The process as defined by claim 1, wherein the polyoxyalkylene compound of the general formula [II] is hydrogenated prior to reaction with the organic halide [III].
Claim 22
Dependent Claim
20 words
The process as defined by claim 1, wherein the reaction temperature ranges from about 20° C. to about 150° C.
Claim 23
Dependent Claim
18 words
The process as defined by claim 21, wherein the reaction temperature ranges from 50° C. to 120° C.
Claim 24
Dependent Claim
30 words
The process as defined by claim 1, wherein the initial concentration of alkali metal hydroxide in the aqueous solution is in the range of from 40% to 75% by weight.
Claim 25
Dependent Claim
33 words
The process as defined by claim 1, wherein the molar ratio of the organic halide to hydroxyl content of the polyoxyalkylene compound is in the range of from about 2 to about 5.
Claim 26
Dependent Claim
16 words
The process as defined by claim 1, further comprising hydrogenating the resultant etherified polyoxyalkylene derivative [I].
Claim 27
Dependent Claim
20 words
The process as defined by claim 1, wherein the reaction is conducted in the presence of an inert organic solvent.
Claim 28
Dependent Claim
19 words
The process as defined by claim 1, wherein the reaction is conducted under an atmosphere of an inert gas.
Claim 29
Dependent Claim
33 words
The process as defined by claim 19, wherein the reducing agent is employed in amounts of from about 0.05 to about 10% by weight, based on the weight of the polyoxyalkylene compound [II].
Claim 30
Dependent Claim
14 words
The process as defined by claim 1, wherein the reaction is carried out batchwise.
Claim 31
Dependent Claim
14 words
The process as defined by claim 1, wherein the reaction is carried out continuously.
Claim 32
Dependent Claim
27 words
The process as defined by claim 1, wherein the product etherified polyoxyalkylene derivative [I] is selected from the group consisting of those of the structural formulae: ##STR29##
Claim 33
Dependent Claim
23 words
The process as defined by claim 1, wherein the polyoxyalkylene compound of the structural formula [II] has at least 6 repeating oxyalkylene units.
Claim 34
Dependent Claim
25 words
The process as defined by claim 1, wherein the total number of carbon atoms in R 2 and R 3 is no greater than 25.
Claim 35
Dependent Claim
58 words
The process as defined by claim 1, wherein the organic halide [III] is X-CH 2 -CR 4 R 5 R 6 , in which each R 4 , R 5 and R 6 is either hydrogen or a hydrocarbon having up to 20 carbon atoms selected from the group consisting of alkyl, alkenyl, cycloalkyl, aryl, aralkyl and alkaryl.
Claim 36
Dependent Claim
88 words
The process as defined by claim 1, wherein the organic halide [III] is selected from the group consisting of methyl chloride, methyl bromide, ethyl bromide, n-propyl chloride, n-propyl bromide, butyl chloride, butyl bromide, isoamyl choride, isoamyl bromide, hexyl chloride, hexyl bromide, octyl chloride, octyl bromide, decyl chloride, decyl bromide, lauryl chloride, lauryl bromide, myristyl chloride, myristyl bromide, cetyl chloride, cetyl bromide, stearyl chloride, stearyl bromide, 9-decenyl bromide, 9-dodecenyl chloride, 9-dodecenyl bromide, oleyl chloride, oleyl bromide, 9,12-octadecadienyl chloride, 9,12-octadecadienyl bromide, 2-cyclohexylethyl chloride, 2-cyclohexylethyl bromide, 2-phenylethyl chloride and 2-phenylethyl bromide.
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) | 1984-11-16 | 1985-05-18 | 1985-11-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-11-16 | 1989-05-18 | 1989-11-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-11-16 | 1993-05-18 | 1993-11-17 | $7700.00 | Window Closed / Lapsed |