GB788397A - Improvements in the preparation of resinous condensation products of alkenylphenols and aldehydes - Google Patents
Improvements in the preparation of resinous condensation products of alkenylphenols and aldehydesInfo
- Publication number
- GB788397A GB788397A GB3045554A GB3045554A GB788397A GB 788397 A GB788397 A GB 788397A GB 3045554 A GB3045554 A GB 3045554A GB 3045554 A GB3045554 A GB 3045554A GB 788397 A GB788397 A GB 788397A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenols
- phenol
- formaldehyde
- mixture
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01H—ELECTRIC SWITCHES; RELAYS; SELECTORS; EMERGENCY PROTECTIVE DEVICES
- H01H71/00—Details of the protective switches or relays covered by groups H01H73/00 - H01H83/00
- H01H71/10—Operating or release mechanisms
- H01H71/50—Manual reset mechanisms which may be also used for manual release
- H01H71/62—Manual reset mechanisms which may be also used for manual release with means for preventing resetting while abnormal condition persists, e.g. loose handle arrangement
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Abstract
Alkenyl phenols are obtained by reaction of conjugated dienes with phenolic compounds. In an example, toluene, phenol and sulphuric acid are charged into a glass-lined reactor and butadiene added over a period of 15 minutes, the temperature being maintained at 55 DEG F. After agitation for 18 hours the acid layer which separates out is drawn off and the remaining reaction mixture is neutralized with sodium carbonate and then distilled to give a 59 per cent yield of monobutenylphenols and a mixture containing dibutenylphenols, higher boiling phenols and unreacted phenol and ethers.ALSO:A resinous condensation product, for use as coating compositions, lacquers and varnishes, and in making laminates and moulding powders, may be made by reacting a mixture of mono-and poly-alkenyl phenols containing at least 4 carbon atoms in each alkenyl radical with an aldehyde, preferably in the presence of an acidic or basic condensation catalyst. Phenol mixtures specified are butenyl-phenols, -cresols, -catechols, -2 : 3-dimethoxyphenols, -resorcinols, and -guaicols, 2-chlorobutenyl-cresol, and -phenol, 2-iodobutenylphenol, o- and p-cyclopentenyl-phenol, pentenyl-phenol, -cresol and -guaicol, halopentenyl-phenols and -guaicols. The preferred aldehyde is formaldehyde, e.g as formalin, paraldehyde or trioxymethylene. Catalysts specified are sodium, potassium and barium hydroxides, sodium and potassium carbonates, ammonia, and sulphuric, hydrochloric, phosphoric, acetic, propionic and oxalic acids. The catalysts are used in amount, e.g. of from 0.5 to 5 per cent by weight of the reactants, and the reactants are used in amounts, e.g. of from 0.5 to 5 mols. of aldehyde per mol. of phenol, and preferably from 1.5 to 2 : 1 when an alkaline catalyst is used and from 0.8 to 1 : 1 when an acid catalyst is used. The reaction is best effected by mixing the phenols and catalyst under an inert atmosphere such as nitrogen and or in the presence of sodium hydrosulphite, while maintaining the temperature at room temperature (25 DEG C.) until a solution is obtained; the aldehyde is then added with stirring while the temperature is kept below 35 DEG C., with subsequent acidification to a pH of 5 and separation into two layers. The resin layer, after removal of the water layer, is washed with water, mixed with a chelate or sequestrate, e.g. ethylenediaminetetracarboxylic acid (to form a complex with any iron present), and dehydrated. Many chelates or sequestrates are specified. The stability and compatibility with other synthetic resins of the products is enhanced by heating them with alcohols in an acidic or neutral medium, alcohols specified being methyl, ethyl, propyl, butyl, amyl, and 2-ethyl-hexyl alcohols, castor oil, butane diol-1 : 4, soya alcohols, allyl alcohol, ethylene glycol and alkyd resins containing OH groups. The alcohol and/or chelate &c. may however be added during the condensation reaction. In examples, a mixture of butenylphenols is reacted with (2) furfural, crotonaldehyde or acetaldehyde in the presence of caustic soda; (4) formaldehyde in the presence of caustic soda, and the product was further reacted with a sequestrate and with butanol; (5) formaldehyde in the presence of hydrochloric acid; a mixture of cyclopentenyl phenols was condensed with formaldehyde (3) in the presence of caustic soda; and (7) in the presence of hydrochloric acid; (6) a mixture of pentenyl-phenols was acid-condensed with formaldehyde; (8 to 14) butenylphenol-formaldehyde resins were heated with a number of different alcohols; (15) the resin of Example (4) was blended with an oleroresin varnish, with or without zinc oxide and titania; (16) the stability of the alcohol-reacted resins is compared with the unreacted resins.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US390089A US2843566A (en) | 1953-11-03 | 1953-11-03 | Alkenylphenol-aldehyde |
US390088A US2843565A (en) | 1953-11-03 | 1953-11-03 | Butenyl phenol-aldehyde resins |
US427386A US2907751A (en) | 1954-05-03 | 1954-05-03 | Alkenylphenol-aldehyde resins |
US427384A US2848436A (en) | 1954-05-03 | 1954-05-03 | Preparation of phenolic resins |
Publications (1)
Publication Number | Publication Date |
---|---|
GB788397A true GB788397A (en) | 1958-01-02 |
Family
ID=41680155
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3045554A Expired GB788397A (en) | 1953-11-03 | 1954-10-22 | Improvements in the preparation of resinous condensation products of alkenylphenols and aldehydes |
Country Status (3)
Country | Link |
---|---|
DE (1) | DE1019463B (en) |
FR (1) | FR1115963A (en) |
GB (1) | GB788397A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0497987A1 (en) * | 1990-08-27 | 1992-08-12 | Fujitsu Limited | Epoxy resin composition |
WO2001044369A1 (en) * | 1999-12-13 | 2001-06-21 | Resolution Research Nederland B.V. | Epoxy resin composition |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE807440C (en) * | 1948-11-24 | 1951-06-28 | British Resin Prod Ltd | Process for the production of plastics |
-
1954
- 1954-10-22 GB GB3045554A patent/GB788397A/en not_active Expired
- 1954-11-02 FR FR1115963D patent/FR1115963A/en not_active Expired
- 1954-11-02 DE DEP12974A patent/DE1019463B/en active Pending
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0497987A1 (en) * | 1990-08-27 | 1992-08-12 | Fujitsu Limited | Epoxy resin composition |
EP0497987A4 (en) * | 1990-08-27 | 1993-02-03 | Fujitsu Limited | Epoxy resin composition |
WO2001044369A1 (en) * | 1999-12-13 | 2001-06-21 | Resolution Research Nederland B.V. | Epoxy resin composition |
Also Published As
Publication number | Publication date |
---|---|
DE1019463B (en) | 1957-11-14 |
FR1115963A (en) | 1956-05-02 |
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