GB1027056A - Thermoset resins and intermediates therefor - Google Patents
Thermoset resins and intermediates thereforInfo
- Publication number
- GB1027056A GB1027056A GB667364A GB667364A GB1027056A GB 1027056 A GB1027056 A GB 1027056A GB 667364 A GB667364 A GB 667364A GB 667364 A GB667364 A GB 667364A GB 1027056 A GB1027056 A GB 1027056A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formaldehyde
- resin
- stage
- resins
- glycol
- 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
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/10—Polythioethers from sulfur or sulfur-containing compounds and aldehydes or ketones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- 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
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
-
- 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
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/40—Chemically modified polycondensates
-
- 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
- C08G71/00—Macromolecular compounds obtained by reactions forming a ureide or urethane link, otherwise, than from isocyanate radicals in the main chain of the macromolecule
- C08G71/02—Polyureas
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/02—Polyureas
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Laminated Bodies (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Abstract
Glycol formthionals <FORM:1027056/C2/1> where X is O or S, n is an integer and the unit <FORM:1027056/C2/2> has an average molecular weight of 77-107 and a sulphur content of 43-65%, are prepared by saturating formalin with H2S at pH 3-9 below 15 DEG C. A preferred mixture contains largely HOCH2SCH2OCH2OH and HOCH2SCH2SCH2OH in approximately 3 : 1 mole ratio. Water-soluble resins may be obtained by heating together substantially equimolar amounts of urea and glycol-formthional at pH 4-6 below 60 DEG C. until traces of solid appear. These polymers contain units <FORM:1027056/C2/3> apparently fewer than 100, probably fewer than 10 per molecule, on average.ALSO:A thermosetting resin comprises 40-100 weight per cent of a glycol-formthional/urea resin having repeating units <FORM:1027056/C3/1> where X = O or S, n is an integer, and the unit <FORM:1027056/C3/2> has an average molecular weight of 77-107 and a sulphur content of 43-65%, and 0-60% complementally of a natural polyacetal of recurring unit <FORM:1027056/C3/3> and/or an aminoplast resin as filler, and/or an epoxy compound or epoxy resin as stabilizer and/or a polybasic acid anhydride as hardener. The glycol-formthionals are prepared by saturating formalin with H2S at pH 3-9, below 15 DEG C. Water-soluble, A-stage, glycol-formthional/urea resins are obtained by heating substantially equimolar amounts of urea and glycol-formthional at pH 4-6, below 60 DEG C., until traces of solids appear. The pH of the solution may be stabilized by addition of phenolic antioxidants, e.g. 2,6-di-t-butyl-4-methyl-(or -methoxy-) phenol. These polymers apparently contain less than 100, probably less than 10, units as above. Solutions of these resins may be used with or without modifiers to laminate coat or impregnate substrates, and may be thinned with organic solvents, e.g. alcohols, ketones, ethers. They may be mixed with reactive fillers, e.g. starch, cellulose, melamine/formaldehyde, guanidine/formaldehyde, benzoguanidine/formaldehyde, biguanide/formaldehyde, guanylurea/formaldehyde, biuret/formaldehyde or urea/formaldehyde. a -Cellulose is preferred, amounting to up to 55% by weight of the resin/filler mixture, and may be precoated with a melamine/formaldehyde or benzoguanidine/formaldehyde which is cured before the filler and the resin are mixed. Non-reacting fillers also may be added, e.g. carbon black, glass, asbestos, silica, cadmium red, cadmium yellow, TiO2, or phthalocyanine green, and lubricants, e.g. MoS2, polytetrafluorethylene or glycerol monostearate. A water-insoluble B-stage resin still capable of being shaped may be obtained by heating the A-stage resin mixture at pH 3-6, below 60 DEG C., losing volatiles until less than 3 weight per cent of water remains. This resin may then be milled and stabilized by treatment with epoxy compounds or resins, e.g. glycidyl ethers, or low molecular weight condensates thereof with phenols or polyols, which may be applied by spraying, followed by an acetone solution of a volatile organic acid. Hardeners, e.g. maleic, pyromellitic or phthalic anhydride, may similarly be added at this stage. Solid C-stage resins are obtained by heating the B-stage resins at 60-180 DEG C. under pressures up to 15,000 p.s.i. In examples A-stage resins are used to laminate paper and birch veneers. B-stage mixtures are made, using as filler a -cellulose impregnated with a melamine/formaldehyde precondensate, and incorporating minor amounts of glyceryl monostearate and TiO2; these are dried and ground and sprayed with nonylphenol glycidyl ether in hexane, formic acid in acetone, and phthalic anhydride is finally added. Cure is at 140 DEG C. and 3000 p.s.i. A cup and saucer are made from this powder.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US26006763A | 1963-02-20 | 1963-02-20 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1027056A true GB1027056A (en) | 1966-04-20 |
Family
ID=22987647
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB667364A Expired GB1027056A (en) | 1963-02-20 | 1964-02-18 | Thermoset resins and intermediates therefor |
Country Status (4)
Country | Link |
---|---|
BE (1) | BE644067A (en) |
CH (1) | CH437787A (en) |
GB (1) | GB1027056A (en) |
NL (1) | NL6401585A (en) |
-
1964
- 1964-02-18 GB GB667364A patent/GB1027056A/en not_active Expired
- 1964-02-19 BE BE644067D patent/BE644067A/xx unknown
- 1964-02-19 CH CH200764A patent/CH437787A/en unknown
- 1964-02-20 NL NL6401585A patent/NL6401585A/xx unknown
Also Published As
Publication number | Publication date |
---|---|
NL6401585A (en) | 1964-08-21 |
BE644067A (en) | 1964-08-19 |
CH437787A (en) | 1967-06-15 |
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