GB1363227A - Phenol-aldehyde resins - Google Patents
Phenol-aldehyde resinsInfo
- Publication number
- GB1363227A GB1363227A GB798071*[A GB798071A GB1363227A GB 1363227 A GB1363227 A GB 1363227A GB 798071 A GB798071 A GB 798071A GB 1363227 A GB1363227 A GB 1363227A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenol
- aldehyde
- resole
- urea
- 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
- 229920005989 resin Polymers 0.000 title abstract 2
- 239000011347 resin Substances 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 abstract 5
- 229920003987 resole Polymers 0.000 abstract 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 4
- 150000001299 aldehydes Chemical class 0.000 abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 3
- 239000004202 carbamide Substances 0.000 abstract 3
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 abstract 3
- 238000000465 moulding Methods 0.000 abstract 3
- 229920000877 Melamine resin Polymers 0.000 abstract 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000010425 asbestos Substances 0.000 abstract 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 abstract 2
- IXQGCWUGDFDQMF-UHFFFAOYSA-N o-Hydroxyethylbenzene Natural products CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 abstract 2
- 229910052895 riebeckite Inorganic materials 0.000 abstract 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 abstract 1
- YWYHGNUFMPSTTR-UHFFFAOYSA-N 1-methyl-4-(4-methylphenoxy)benzene Chemical compound C1=CC(C)=CC=C1OC1=CC=C(C)C=C1 YWYHGNUFMPSTTR-UHFFFAOYSA-N 0.000 abstract 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- 229930040373 Paraformaldehyde Natural products 0.000 abstract 1
- 239000004698 Polyethylene Substances 0.000 abstract 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 1
- 239000003377 acid catalyst Substances 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000005266 casting Methods 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 239000004927 clay Substances 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 239000007859 condensation product Substances 0.000 abstract 1
- 229930003836 cresol Natural products 0.000 abstract 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 239000002657 fibrous material Substances 0.000 abstract 1
- 239000000945 filler Substances 0.000 abstract 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000011521 glass Substances 0.000 abstract 1
- 150000002334 glycols Chemical class 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 229910021645 metal ion Inorganic materials 0.000 abstract 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract 1
- 239000010445 mica Substances 0.000 abstract 1
- 229910052618 mica group Inorganic materials 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- 235000006408 oxalic acid Nutrition 0.000 abstract 1
- 229920002866 paraformaldehyde Polymers 0.000 abstract 1
- 229920001568 phenolic resin Polymers 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- 229920001223 polyethylene glycol Polymers 0.000 abstract 1
- 229920001451 polypropylene glycol Polymers 0.000 abstract 1
- 235000013772 propylene glycol Nutrition 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000011342 resin composition Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 150000003739 xylenols Chemical class 0.000 abstract 1
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
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/04—Polymeric products of isocyanates or isothiocyanates with vinyl compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/05—Alcohols; Metal alcoholates
- C08K5/053—Polyhydroxylic alcohols
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2361/00—Characterised by the use of condensation polymers of aldehydes or ketones; Derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2361/00—Characterised by the use of condensation polymers of aldehydes or ketones; Derivatives of such polymers
- C08J2361/04—Condensation polymers of aldehydes or ketones with phenols only
- C08J2361/06—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)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
1363227 Phenol-aldehyde resins R FARKAS 11 Aug 1971 [11 Aug 1970 26 March 1971] 38713/70 and 7980/71 Heading C3R A moulding composition comprises an alkali metal-catalysed phenol-aldehyde resole condensation product, the mole ratio of aldehyde to phenol being 1À1 to 2À5 : 1, a glycol in an amount of 12-35% wt. based on the weight of the resole, and an acidic curing catalyst. In a modification the glycol is incorporated during the phenol-aldehyde condensation. Suitable aldehydes are formaldehyde, paraformaldehyde and other aldehydes having up to 7 carbon atoms. Suitable phenols are phenol, cresol, xylenol and ethyl-phenol. The total water content of the composition should not exceed 42% wt. Specific glycols mentioned are mono-, di- and tri-ethylene and propylene glycols, butylene glycol, polyethylene and polypropylene glycols and monoglyceryl cresyl ether. The acid catalyst is preferably one or more of oxalic, H 3 PO 4 , H 2 SO 4 , HCl, para-toluene sulphonic acid and benzene sulphonic acid. The compositions may also include one or more of urea, melamine, dicyandiamide and an amino-aldehyde resin. Up to 10% wt. of the composition of an alcohol, ketone or ester may be included to impart combustibility to the articles moulded therefrom. Fillers such as glass or asbestos fibres, mica and clay may be added. In an ebodiment a colourless moulding is prepared from the phenol-aldehyde resin composition in which the purity of the reactant is such that it contains less than 5 p.p.m. of colour-forming metal ions and in which the final curing is effected in the presence of at least 4% wt. of the resole of urea and/or melamine and/or dicyandiamide and/or a urea-, melamine- and/or dicyandiamide, aldehyde condensate, and at least 5% wt. of the resole of an organic reducing agent and/or H 3 PO 4 or one of its derivatives. In the examples compositions are prepared from an aqueous phenol-formaldehyde resole, dipropylene glycol, para-toluenesulphonic acid and either (i) urea, oxalic acid in alcohol, or (ii) asbestos fibres, or (iii) as for (i) but with no alcohol. Uses.-Moulding or casting; as surfacing materials; for impregnating sheet fibrous materials.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB798071*[A GB1363227A (en) | 1971-08-11 | 1971-08-11 | Phenol-aldehyde resins |
| FR7231752A FR2197929B3 (en) | 1971-08-11 | 1972-09-07 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB798071*[A GB1363227A (en) | 1971-08-11 | 1971-08-11 | Phenol-aldehyde resins |
| GB3871370 | 1971-08-11 | ||
| FR7231752A FR2197929B3 (en) | 1971-08-11 | 1972-09-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1363227A true GB1363227A (en) | 1974-08-14 |
Family
ID=27249945
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB798071*[A Expired GB1363227A (en) | 1971-08-11 | 1971-08-11 | Phenol-aldehyde resins |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR2197929B3 (en) |
| GB (1) | GB1363227A (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4079031A (en) * | 1976-07-14 | 1978-03-14 | Delta Oil Products Corporation | Improved foundry process and binder resin composition therefor |
| FR2370515A1 (en) * | 1976-10-08 | 1978-06-09 | Albright & Wilson | CURING CATALYSTS FOR PHENOLIC RESINS |
| US4634758A (en) * | 1984-10-12 | 1987-01-06 | Acme Resin Corporation | Process for preparing alkoxy-modified phenolic resole resins |
| US4723592A (en) * | 1984-10-12 | 1988-02-09 | Acme Resin Corporation | Process for preparing foundry cores and molds |
| US4785073A (en) * | 1983-08-16 | 1988-11-15 | Polymer Tectonics Limited | Melamine-phenol-formaldehyde resole modified by glycols moulding composition |
| US5015529A (en) * | 1986-12-24 | 1991-05-14 | Occidental Chemical Corporation | Phenolic molding compositions |
| US5066693A (en) * | 1988-09-14 | 1991-11-19 | Occidental Chemical Corporation | Molding compositions of resole phenolic resin and epoxy resin |
| EP0869980A4 (en) * | 1995-12-27 | 1999-03-24 | Borden Inc | Reactive diluents for acid curable phenolic compositions |
| US6133403A (en) * | 1996-12-23 | 2000-10-17 | Borden Chemical, Inc. | Reactive diluents for acid curable phenolic compositions |
| CN114752272A (en) * | 2022-05-25 | 2022-07-15 | 潍坊工程职业学院 | External waterproof and antirust coating composition for automobile exhaust system and application method thereof |
| CN116005490A (en) * | 2022-12-12 | 2023-04-25 | 太尔胶粘剂(广东)有限公司 | High-toughness impregnated film paper and preparation method and application thereof |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4202945A (en) * | 1979-04-03 | 1980-05-13 | Leinhardt Franklyn J | Phenolic foam materials and method of making same |
| DE4211802C2 (en) * | 1992-04-08 | 2002-11-14 | Gewerk Keramchemie | Molding compound and process for its manufacture |
-
1971
- 1971-08-11 GB GB798071*[A patent/GB1363227A/en not_active Expired
-
1972
- 1972-09-07 FR FR7231752A patent/FR2197929B3/fr not_active Expired
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4079031A (en) * | 1976-07-14 | 1978-03-14 | Delta Oil Products Corporation | Improved foundry process and binder resin composition therefor |
| FR2370515A1 (en) * | 1976-10-08 | 1978-06-09 | Albright & Wilson | CURING CATALYSTS FOR PHENOLIC RESINS |
| US4785073A (en) * | 1983-08-16 | 1988-11-15 | Polymer Tectonics Limited | Melamine-phenol-formaldehyde resole modified by glycols moulding composition |
| US4634758A (en) * | 1984-10-12 | 1987-01-06 | Acme Resin Corporation | Process for preparing alkoxy-modified phenolic resole resins |
| US4723592A (en) * | 1984-10-12 | 1988-02-09 | Acme Resin Corporation | Process for preparing foundry cores and molds |
| US5015529A (en) * | 1986-12-24 | 1991-05-14 | Occidental Chemical Corporation | Phenolic molding compositions |
| US5066693A (en) * | 1988-09-14 | 1991-11-19 | Occidental Chemical Corporation | Molding compositions of resole phenolic resin and epoxy resin |
| EP0869980A4 (en) * | 1995-12-27 | 1999-03-24 | Borden Inc | Reactive diluents for acid curable phenolic compositions |
| US6133403A (en) * | 1996-12-23 | 2000-10-17 | Borden Chemical, Inc. | Reactive diluents for acid curable phenolic compositions |
| CN114752272A (en) * | 2022-05-25 | 2022-07-15 | 潍坊工程职业学院 | External waterproof and antirust coating composition for automobile exhaust system and application method thereof |
| CN114752272B (en) * | 2022-05-25 | 2023-06-06 | 潍坊工程职业学院 | A kind of waterproof and antirust coating composition for external use of automobile exhaust system and application method thereof |
| CN116005490A (en) * | 2022-12-12 | 2023-04-25 | 太尔胶粘剂(广东)有限公司 | High-toughness impregnated film paper and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2197929B3 (en) | 1975-10-17 |
| FR2197929A1 (en) | 1974-03-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| 433D | Application made for revocation (sect. 33/1949) | ||
| 433G | Case decided by the comptroller ** application refused (sect. 33/1949) | ||
| 732 | Registration of transactions, instruments or events in the register (sect. 32/1977) | ||
| PE20 | Patent expired after termination of 20 years |