US4226800A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Synthesis of acetylene-terminated compounds
Assignee: United States Department of the Air Force
•
Filing: 1979-06-14
•
Granted: 1980-10-07
•
Expires: 1999-06-14
Abstract
Abstract Phenolic materials containing propargyl groups are prepared by reacting a polyhydric, phenolic material with propargyl bromide, the reaction being conducted in an aqueous sodium hydroxide solution. The products can be thermally polymerized to polymers which are useful as adhesives and as matrix resins in the fabrication of composites.
Inventors
- 👤 Lewellyn G. Picklesimer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 16:46
CPC Classifications
C; C07; C07C; C07C43/00; C07C43/02; C07C43/20; C07C43/215; C07C315/00; C07C315/04; C07C319/00; C07C319/14; C07C319/20; C08; C08G; C08G61/00; C08G61/12
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
31 words
A process for preparing a phenolic material containing propargyl groups which comprises reacting a polyhydric, phenolic material with propargyl bromide, the reaction being carried out in an aqueous sodium hydroxide solution.
Claim 2
Dependent Claim
31 words
A process for preparing a phenolic material containing propargyl groups which comprises reacting a polyhydric, phenolic material with propargyl bromide, the reaction being carried out in an aqueous sodium hydroxide solution.
Claim 3
Dependent Claim
36 words
The process according to claim 1 in which the reaction is conducted at a temperature ranging from about 70° C. to reflux temperature of the aqueous solution for a period of about 1 to 3 hours.
Claim 4
Dependent Claim
31 words
The process according to claim 2 in which the polyhydric, phenolic material is selected from the group consisting of a polyhydric, mononuclear phenol; a polyhydric, polynuclear phenol; and a phenolic resin.
Claim 5
Dependent Claim
17 words
The process according to claim 3 in which the polyhydric, mononuclear phenol is resorcinol, hydroquinol or 2,3-dicyanohydroquinone.
Claim 6
Dependent Claim
23 words
The process according to claim 3 in which the polynuclear, polyhydric phenol has the following formula: ##STR5## wherein Z is --O--, --S--, ##STR6##
Claim 7
Dependent Claim
21 words
The process according to claim 3 in which the phenolic resin is a phenol novolac resin or a resorcinol novolac resin.
Claim 8
Dependent Claim
37 words
The process according to claim 3 in which the amount of propargyl bromide is about equivalent to the hydroxyl content of the phenolic material and the mole ratio of sodium hydroxide to propargyl bromide is about 1:1.
Claim 9
Dependent Claim
65 words
A process for preparing a phenolic compound containing propargyl ether groups which comprises reacting propargyl bromide with a polyhydric phenol selected from the group consisting of 4,4'-dihydroxydiphenyl sulfone and 4,4'-isopropylidenediphenol, the reaction being conducted in an aqueous sodium hydroxide solution at a temperature ranging from about 70° C. to reflux temperature of the sodium hydroxide solution for a period of about 1 to 3 hours.
Claim 10
Dependent Claim
65 words
A process for preparing a phenolic compound containing propargyl ether groups which comprises reacting propargyl bromide with a polyhydric phenol selected from the group consisting of 4,4'-dihydroxydiphenyl sulfone and 4,4'-isopropylidenediphenol, the reaction being conducted in an aqueous sodium hydroxide solution at a temperature ranging from about 70° C. to reflux temperature of the sodium hydroxide solution for a period of about 1 to 3 hours.
Claim 11
Dependent Claim
34 words
The process according to claim 8 in which the mole ratio of propargyl bromide to polyhydric phenol ranges from 2:1 to 2.5:1 and the mole ratio of sodium hydroxide to propargyl bromide is 1:1.
Claim 12
Dependent Claim
93 words
A process for preparing a phenolic material containing propargyl groups which comprises reacting propargyl bromide with a polynuclear, polyhydric phenol having the following formula: ##STR7## wherein Z is --0--, --S--, ##STR8## the reaction being conducted in an aqueous sodium hydroxide solution at a temperature ranging from about 70° C. to reflux temperature of the sodium hydroxide solution for a period of about 1 to 3 hours, the mole ratio of propargyl bromide to polyhydric phenol ranging from 2:1 to 2.5:1, and the mole ratio of sodium hydroxide to propargyl bromide being about 1:1.
Claim 13
Dependent Claim
93 words
A process for preparing a phenolic material containing propargyl groups which comprises reacting propargyl bromide with a polynuclear, polyhydric phenol having the following formula: ##STR7## wherein Z is --0--, --S--, ##STR8## the reaction being conducted in an aqueous sodium hydroxide solution at a temperature ranging from about 70° C. to reflux temperature of the sodium hydroxide solution for a period of about 1 to 3 hours, the mole ratio of propargyl bromide to polyhydric phenol ranging from 2:1 to 2.5:1, and the mole ratio of sodium hydroxide to propargyl bromide being about 1:1.
Claim 14
Dependent Claim
15 words
The process according to claim 10 in which the polynuclear, polyhydric phenol is 4,4'-dihydroxydiphenyl sulfone.
Claim 15
Dependent Claim
14 words
The process according to claim 10 in which the polynuclear, polyhydric phenol is 4,4'-isopropylidenediphenol.
Claim 16
Dependent Claim
126 words
A process for preparing a phenolic material containing propargyl groups which comprises reacting propargyl bromide with a phenolic material selected from the group consisting of resorcinol, hydroquinol, 2,3-dicyanohydroquinone, 4,4'-dihydroxydiphenylsulfone, 4,4'-isopropylidenediphenol, a phenol novolac resin having the following formula: ##STR9## a resorcinol novolac resin having the following formula: ##STR10## wherein n in each formula is an integer ranging from about 2 to 100, the reaction being conducted in an aqueous sodium hydroxide solution at a temperature ranging from about 70° C. to reflux temperature of the sodium hydroxide solution for a period of about 1 to 3 hours, the amount of propargyl bromide being about equivalent to the hydroxyl content of the phenolic material, and the mole ratio of sodium hydroxide to propargyl bromide being about 1:1.
Claim 17
Dependent Claim
126 words
A process for preparing a phenolic material containing propargyl groups which comprises reacting propargyl bromide with a phenolic material selected from the group consisting of resorcinol, hydroquinol, 2,3-dicyanohydroquinone, 4,4'-dihydroxydiphenylsulfone, 4,4'-isopropylidenediphenol, a phenol novolac resin having the following formula: ##STR9## a resorcinol novolac resin having the following formula: ##STR10## wherein n in each formula is an integer ranging from about 2 to 100, the reaction being conducted in an aqueous sodium hydroxide solution at a temperature ranging from about 70° C. to reflux temperature of the sodium hydroxide solution for a period of about 1 to 3 hours, the amount of propargyl bromide being about equivalent to the hydroxyl content of the phenolic material, and the mole ratio of sodium hydroxide to propargyl bromide being about 1:1.
References Cited (Backward Citations)
US4141921A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-10-07 | 1984-04-07 | 1984-10-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-10-07 | 1988-04-07 | 1988-10-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-10-07 | 1992-04-07 | 1992-10-07 | $7700.00 | Window Closed / Lapsed |