US4558116A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for preparing relatively high molecular weight epoxy resins
Assignee: Dow Chemical Co
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Filing: 1985-03-04
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Granted: 1985-12-10
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Expires: 2005-03-04
Abstract
Abstract Epoxy resins low in aliphatic halogen are prepared by reacting a polyhydric phenol with an excess of an epihalohydrin in the presence of a secondary alcohol and an aqueous solution of an alkali metal hydroxide until from 45 to <70 percent of the phenolic hydroxyl groups have reacted; removing unreacted polyhydric phenol therefrom until less than 4% total phenolic hydroxyl remains in the reaction product; dehydrohalogenating the resultant intermediate product and recovering the epoxy resin therefrom.
Inventors
- 👤 Walter L. Wernli
- 👤 Robert P. Shirtum
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 16:29
CPC Classifications
C; C07; C07D; C07D303/00; C07D303/02; C07D303/12; C07D303/18; C07D303/20; C07D303/24; C08; C08G; C08G59/00; C08G59/02; C08G59/04; C08G59/06; C08G59/063
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
166 words
In a process for preparing relatively low molecular weight epoxy resins by reacting at least one polyhydric phenol with an excess of at least one epihalohydrin in the presence of an alcohol and an alkali metal hydroxide followed by dehydrohalogenation of the resultant halohydrin intermediate; the improvement which comprises (1) employing a secondary alcohol as the alcohol; (2) terminating the reaction between the polyhydric phenol and the epihalohydrin when from about 45 to less than about 70 percent of the phenolic hydroxyl groups have reacted and removing the unreacted epihalohydrin therefrom thereby producing a halohydrin intermediate product; (3) removing unreacted polyhydric phenol from the resultant halohydrin intermediate product such that the concentration of phenolic hydroxyl-containing material therein is less than about 4, preferably less than about 1 percent by weight; (4) dehydrohalogenating the product from step (3) with a suitable dehydrohalogenating agent; and (5) recovering from step (4) a glycidyl ether of a polyhydric phenol containing less than about 1500 ppm total aliphatic halogen by weight.
Claim 2
Dependent Claim
166 words
In a process for preparing relatively low molecular weight epoxy resins by reacting at least one polyhydric phenol with an excess of at least one epihalohydrin in the presence of an alcohol and an alkali metal hydroxide followed by dehydrohalogenation of the resultant halohydrin intermediate; the improvement which comprises (1) employing a secondary alcohol as the alcohol; (2) terminating the reaction between the polyhydric phenol and the epihalohydrin when from about 45 to less than about 70 percent of the phenolic hydroxyl groups have reacted and removing the unreacted epihalohydrin therefrom thereby producing a halohydrin intermediate product; (3) removing unreacted polyhydric phenol from the resultant halohydrin intermediate product such that the concentration of phenolic hydroxyl-containing material therein is less than about 4, preferably less than about 1 percent by weight; (4) dehydrohalogenating the product from step (3) with a suitable dehydrohalogenating agent; and (5) recovering from step (4) a glycidyl ether of a polyhydric phenol containing less than about 1500 ppm total aliphatic halogen by weight.
Claim 3
Dependent Claim
99 words
A process of claim 1 wherein (i) the reaction between the polyhydric phenol and the epihalohydrin is conducted at a temperature of from about 10° C. to about 90° C.; (ii) the reaction between the polyhydric phenol and the epihalohydrin is terminated when from about 50 to about 60% of the phenolic hydroxyl groups have reacted; (iii) a sufficient quantity of material containing unreacted polyhydric phenol is removed such that the quantity of phenolic hydroxyl-containing material is less than about 1 percent by weight; (iv) dehydrohalogenation is conducted at a temperature of from about 5° to about 90° C.
Claim 4
Dependent Claim
77 words
A process of claim 2 wherein (i) the reaction between the polyhydric phenol and the epihalohydrin is conducted at a temperature of from about 40° C. to about 60° C.; (ii) a sufficient quantity of material containing unreacted polyhydric phenol is removed such that the quantity of phenolic hydroxyl-containing material is less than about 1 percent by weight; and (iii) the dehydrohalogenation reaction is conducted at a temperature of from about 30° C. to about 60° C.
Claim 5
Dependent Claim
36 words
A process of claim 1 wherein said polyhydric phenol is bisphenol A, said epihalohydrin is epichlorohydrin, said alkali metal hydroxide is sodium hydroxide and said dehydrohalogenation agent is a mixture of sodium hydroxide and sodium carbonate.
Claim 6
Dependent Claim
36 words
A process of claim 2 wherein said polyhydric phenol is bisphenol A, said epihalohydrin is epichlorohydrin, said alkali metal hydroxide is sodium hydroxide and said dehydrohalogenation agent is a mixture of sodium hydroxide and sodium carbonate.
Claim 7
Dependent Claim
36 words
A process of claim 3 wherein said polyhydric phenol is bisphenol A, said epihalohydrin is epichlorohydrin, said alkali metal hydroxide is sodium hydroxide and said dehydrohalogenation agent is a mixture of sodium hydroxide and sodium carbonate.
Claim 8
Dependent Claim
94 words
In a process for preparing a relatively high molecular weight epoxy resin by reacting at least one relatively low molecular weight epoxy resin and at least one material containing about two phenolic hydroxyl groups per molecule in the presence of an effective quantity of a suitable catalyst for effecting the reaction between the relatively low molecular weight epoxy resin and the material containing about two phenolic hydroxyl groups per molecule; the improvement which comprises employing as the relatively low molecular weight epoxy resin, one which has been prepared by the process of claim 1.
Claim 9
Dependent Claim
17 words
A process of claim 7 wherein said material containing about two phenolic hydroxyl groups is bisphenol A.
Claim 10
Dependent Claim
94 words
In a process for preparing a relatively high molecular weight epoxy resin by reacting at least one relatively low molecular weight epoxy resin and at least one material containing about two phenolic hydroxyl groups per molecule in the presence of an effective quantity of a suitable catalyst for effecting the reaction between the relatively low molecular weight epoxy resin and the material containing about two phenolic hydroxyl groups per molecule; the improvement which comprises employing as the relatively low molecular weight epoxy resin, one which has been prepared by the process of claim 2.
Claim 11
Dependent Claim
17 words
A process of claim 9 wherein said material containing about two phenolic hydroxyl groups is bisphenol A.
Claim 12
Dependent Claim
94 words
In a process for preparing a relatively high molecular weight epoxy resin by reacting at least one relatively low molecular weight epoxy resin and at least one material containing about two phenolic hydroxyl groups per molecule in the presence of an effective quantity of a suitable catalyst for effecting the reaction between the relatively low molecular weight epoxy resin and the material containing about two phenolic hydroxyl groups per molecule; the improvement which comprises employing as the relatively low molecular weight epoxy resin, one which has been prepared by the process of claim 3.
Claim 13
Dependent Claim
17 words
A process of claim 11 wherein said material containing about two phenolic hydroxyl groups is bisphenol A.
Claim 14
Dependent Claim
94 words
In a process for preparing a relatively high molecular weight epoxy resin by reacting at least one relatively low molecular weight epoxy resin and at least one material containing about two phenolic hydroxyl groups per molecule in the presence of an effective quantity of a suitable catalyst for effecting the reaction between the relatively low molecular weight epoxy resin and the material containing about two phenolic hydroxyl groups per molecule; the improvement which comprises employing as the relatively low molecular weight epoxy resin, one which has been prepared by the process of claim 4.
Claim 15
Dependent Claim
17 words
A process of claim 13 wherein said material containing about two phenolic hydroxyl groups is bisphenol A.
Claim 16
Dependent Claim
94 words
In a process for preparing a relatively high molecular weight epoxy resin by reacting at least one relatively low molecular weight epoxy resin and at least one material containing about two phenolic hydroxyl groups per molecule in the presence of an effective quantity of a suitable catalyst for effecting the reaction between the relatively low molecular weight epoxy resin and the material containing about two phenolic hydroxyl groups per molecule; the improvement which comprises employing as the relatively low molecular weight epoxy resin, one which has been prepared by the process of claim 5.
Claim 17
Dependent Claim
17 words
A process of claim 15 wherein said material containing about two phenolic hydroxyl groups is bisphenol A.
Claim 18
Dependent Claim
94 words
In a process for preparing a relatively high molecular weight epoxy resin by reacting at least one relatively low molecular weight epoxy resin and at least one material containing about two phenolic hydroxyl groups per molecule in the presence of an effective quantity of a suitable catalyst for effecting the reaction between the relatively low molecular weight epoxy resin and the material containing about two phenolic hydroxyl groups per molecule; the improvement which comprises employing as the relatively low molecular weight epoxy resin, one which has been prepared by the process of claim 6.
Claim 19
Dependent Claim
17 words
A process of claim 17 wherein said material containing about two phenolic hydroxyl groups is bisphenol A.
References Cited (Backward Citations)
US2848435A
Cited
US3121727A
Cited
GB1084332A
Cited
US3325452A
Cited
US4017523A
Cited
US4132718A
Cited
US4373073A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-12-09 | 1989-06-10 | 1989-12-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-12-09 | 1993-06-10 | 1993-12-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-12-09 | 1997-06-10 | 1997-12-10 | $7700.00 | Window Closed / Lapsed |