GB607635A - Improvements in or relating to heat-hardenable phenolic resins - Google Patents
Improvements in or relating to heat-hardenable phenolic resinsInfo
- Publication number
- GB607635A GB607635A GB3726/46A GB372646A GB607635A GB 607635 A GB607635 A GB 607635A GB 3726/46 A GB3726/46 A GB 3726/46A GB 372646 A GB372646 A GB 372646A GB 607635 A GB607635 A GB 607635A
- Authority
- GB
- United Kingdom
- Prior art keywords
- resin
- acid
- sulphate
- etherified
- formaldehyde
- 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
- C08G8/28—Chemically modified polycondensates
- C08G8/36—Chemically modified polycondensates by etherifying
-
- 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
- C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
- C08G8/10—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with phenol
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08L61/22—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
- C08L61/24—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds with urea or thiourea
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
- C08L1/08—Cellulose derivatives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
- C08L61/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Abstract
To prepare an alkali-resistant heat-hardenable phenol-formaldehyde resin, at least 50 per cent of the arylhydroxy groups of the resin are etherified and an acid or latent acid-hardening catalyst is added thereto. The products may be blended with urea-formaldehyde resins and are useful as plasticisers for non-etherified phenolic resins, polyvinyl resins, including copolymers and cellulose esters. They are also compatible with drying oils and may be reacted with furfural. A suitable starting material is phenol, m-cresol or m-xylenol or a mixture containing at least 40 per cent of one of these, resorcinol or mono-resorcinol ethers. Suitable catalysts for the initial condensation are oxides or hydroxides of light metals including alkali and alkaline earth metals, e.g. zinc, magnesium or aluminium oxide. The initial condensation may be acid provided the reaction mass is made alkaline, while some uncombined formaldehyde is still present. Suitable etherifying agents are diethyl sulphate, dimethyl sulphate, methyl hydrogen sulphate, benzyl chloride, o-chlorbenzoyl chloride, allyl chloride, methallyl chloride, p-nitrochlorbenzene, bromobenzene, chloracetic acid, chloracetone, benzene sulphonyl chloride, chloromethyl ether, ethylene chlorhydrin, p-dichlorbenzene, trimethylene bromide, dichloroethyl ether, triglycoldichloride or dichlorethylbenzene. Preferably the resin is employed as its sodium salts. Suitable acid-hardening catalysts or latent acid-hardening catalysts are sulphuric, phosphoric, benzene sulphonic, p-toluene sulphonic, ethyl sulphuric, oxalic or oxalic-boric acid, ethyl sulphate, ethyl-benzene sulphonate, sodium ethyl sulphate or ammonium ethyl sulphate. Usually sufficient is added to give a pH of 5 or less. It may be incorporated in the dried resin or in a solution. In the case of oxalic acid, for example, the catalyst may be carried in a stream of hot air or other fluid over the surface of a film or coating of the ether resin, e.g. on the inside of a tube. Solutions of the non-hardened resins may be stabilized by addition of water or alcohol. In the examples: (1) a resin prepared from phenol and formaldehyde in presence of magnesium oxide was dissolved in caustic soda and etherified with diethyl sulphate. Further diethyl sulphate was added as hardening catalyst and the mixture dissolved in toluene is then heated until it gelled. The gel was re-dissolved in butanol to yield a solution which formed films. In example (2), sodium hydroxide was used as the initial condensation catalyst, the resin was etherified with benzyl chloride and phosphoric acid was used as the hardening catalyst. In example (3), the resin was prepared as in example (1), but using excess phenol, etherified with diethyl sulphate and the hardening catalyst was a mixture of boric and oxalic acids. Example (4) was similar to example (1) with phosphoric acid as the hardening catalyst. In example (5), a resin prepared from urea, formaldehyde and ethylendiamine was dissolved in butyl alcohol, mixed with oxalic acid and blended with an alcoholic solution of the etherified resin of example (1). Specifications 409,397 and 511,511 are referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US607635XA | 1945-02-07 | 1945-02-07 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB607635A true GB607635A (en) | 1948-09-02 |
Family
ID=22031593
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3726/46A Expired GB607635A (en) | 1945-02-07 | 1946-02-06 | Improvements in or relating to heat-hardenable phenolic resins |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB607635A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102391449A (en) * | 2011-09-22 | 2012-03-28 | 华南理工大学 | Allyl para-tert-butyl phenyl ether formaldehyde tackifying resin and preparation method thereof |
-
1946
- 1946-02-06 GB GB3726/46A patent/GB607635A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102391449A (en) * | 2011-09-22 | 2012-03-28 | 华南理工大学 | Allyl para-tert-butyl phenyl ether formaldehyde tackifying resin and preparation method thereof |
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