US4656294A
Expired / Lapsed
US
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Polyglycidyl ethers and a process for producing the same
Assignee: Mitsubishi Chemical Corp
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Filing: 1984-07-13
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Granted: 1987-04-07
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Expires: 2004-07-13
Abstract
Abstract A process for producing a polyglycidyl ether which comprises reacting a mixture of 4-oxy-3-methoxybenzaldehyde and 4-oxybenzaldehyde in the molar ratio of 5/95 to 95/5 with pentaerythritol to give a bisphenol having a spiroacetal ring, and further reacting the bisphenol with epihalohydrin or beta -methylepihalohydrin is disclosed. The polyglycidyl ether obtained has excellent solubility in solvents, and the cured product obtained therefrom has excellent elongation, modulus of elasticity, impact resistance, and heat resistance.
Inventors
- 👤 Kaoru Kanayama
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 03:43
CPC Classifications
C; C07; C07D; C07D493/00; C07D493/02; C07D493/10; C08; C08G; C08G59/00; C08G59/02; C08G59/04; C08G59/06; C08G59/063; C08G59/18; C08G59/20; C08G59/22; C08G59/26
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
43 words
A polyglycidyl ether which is produced by reacting a mixture of 4-oxy-3-methoxybenzaldehyde and 4-oxybenzaldehyde in a molar ratio of 5/95 to 95/5 with pentaerythritol to give a bisphenol having a spiroacetal ring, and further reacting the bisphenol thus produced with epihalohydrin or β-methylepihalohydrin.
Claim 2
Dependent Claim
43 words
A polyglycidyl ether which is produced by reacting a mixture of 4-oxy-3-methoxybenzaldehyde and 4-oxybenzaldehyde in a molar ratio of 5/95 to 95/5 with pentaerythritol to give a bisphenol having a spiroacetal ring, and further reacting the bisphenol thus produced with epihalohydrin or β-methylepihalohydrin.
Claim 3
Dependent Claim
34 words
The polyglycidyl ether as claimed in claim 1, wherein the bisphenol is a mixture of bisphenols represented by the formulae (I) to (III) ##STR21## wherein R is hydrogen and R' is a methoxy group.
Claim 4
Dependent Claim
81 words
The polyglycidyl ether as claimed in claim 1, wherein the polyglycidyl ether is a diglycidyl ether represented by the formula ##STR22## wherein R 1 is H or CH 3 , R 2 and R 3 are independently hydrogen or a methoxy group, and m is 0 to 1, and the diglycidyl ether is further reacted with a bisphenol represented by the formula HO--Ar--OH wherein Ar is ##STR23## wherein R 2 and R 3 are independently hydrogen or a methoxy group, ##STR24##
Claim 5
Dependent Claim
21 words
The polyglycidyl ether as claimed in claim 3, wherein the equivalent ratio of bisphenol to diglycidyl ether is 0.01/1 to 1/1.
Claim 6
Dependent Claim
16 words
The polyglycidyl ether as claimed in claim 4, wherein the equivalent ratio is 0.05/1 to 0.8/1.
Claim 7
Dependent Claim
27 words
The polyglycidyl ether as claimed in claim 1, wherein said mixture has a molar ratio of 20-80 mole percent of 4-oxy-3-methoxybenzaldehyde and 80-20 mole percent of 4-oxybenzaldehyde.
Claim 8
Dependent Claim
52 words
The polyglycidyl ether as claimed in claim 1, wherein the reaction between the bisphenol and the epihalohydrin or said β-methylepihalohydrin is further effected first in the presence of a catalyst selected from the group consisting of a phosphonium salt or a quaternary ammonium salt, and then an alkali metal hydroxide is added.
Claim 9
Dependent Claim
17 words
The polyglycidyl ether as claimed in claim 7, wherein said catalyst is tetramethylammonium chloride or tetraethylammonium bromide.
Claim 10
Dependent Claim
31 words
The polyglycidyl ether as claimed in claim 1, wherein the reaction between said bisphenol and said epihalohydrin or said β-methylepihalohydrin is further effected in the presence of an alkali metal hydroxide.
Claim 11
Dependent Claim
108 words
A polyglycidyl ether having the formula: ##STR25## wherein R 1 is H or CH 3 , R 2 and R 3 are independently hydrogen or a methoxy group, but are not simultaneously hydrogen or a methoxy group, n is 0 or an integer of 1 to 20, which is produced by reacting a diglycidyl ether of the formula: ##STR26## wherein R 1 , R 2 and R 3 are as defined above, and m is 0 or 1, with a bisphenol having the formula: HO--Ar--OH wherein Ar is: ##STR27## wherein R 2 and R 3 are as defined above or are selected from the group consisting of: ##STR28##
Claim 12
Dependent Claim
108 words
A polyglycidyl ether having the formula: ##STR25## wherein R 1 is H or CH 3 , R 2 and R 3 are independently hydrogen or a methoxy group, but are not simultaneously hydrogen or a methoxy group, n is 0 or an integer of 1 to 20, which is produced by reacting a diglycidyl ether of the formula: ##STR26## wherein R 1 , R 2 and R 3 are as defined above, and m is 0 or 1, with a bisphenol having the formula: HO--Ar--OH wherein Ar is: ##STR27## wherein R 2 and R 3 are as defined above or are selected from the group consisting of: ##STR28##
Claim 13
Dependent Claim
15 words
The polyglycidyl ether as claimed in claim 10, wherein the methoxy group content is 5-95%.
References Cited (Backward Citations)
US3347871A
Cited
US3388098A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-04-06 | 1990-10-06 | 1991-04-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-04-06 | 1994-10-06 | 1995-04-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-04-06 | 1998-10-06 | 1999-04-07 | $7700.00 | Window Closed / Lapsed |