GB942057A - Process for the production of cross-linked synthetic resins of high molecular weight - Google Patents
Process for the production of cross-linked synthetic resins of high molecular weightInfo
- Publication number
- GB942057A GB942057A GB35332/60A GB3533260A GB942057A GB 942057 A GB942057 A GB 942057A GB 35332/60 A GB35332/60 A GB 35332/60A GB 3533260 A GB3533260 A GB 3533260A GB 942057 A GB942057 A GB 942057A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- ethers
- organic
- reaction
- aromatic
- 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
- C08G16/00—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00
- C08G16/02—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes
- C08G16/0212—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with acyclic or carbocyclic organic compounds
- C08G16/0218—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with acyclic or carbocyclic organic compounds containing atoms other than carbon and hydrogen
- C08G16/0225—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with acyclic or carbocyclic organic compounds containing atoms other than carbon and hydrogen containing oxygen
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/08—Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/16—Organic material
- B01J39/18—Macromolecular compounds
- B01J39/19—Macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds
-
- 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
- C08G10/00—Condensation polymers of aldehydes or ketones with aromatic hydrocarbons or halogenated aromatic hydrocarbons only
- C08G10/02—Condensation polymers of aldehydes or ketones with aromatic hydrocarbons or halogenated aromatic hydrocarbons 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
- C08G16/00—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00
- C08G16/02—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 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
- C08G16/00—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00
- C08G16/02—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes
- C08G16/0212—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with acyclic or carbocyclic organic compounds
- C08G16/0218—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with acyclic or carbocyclic organic compounds containing atoms other than carbon and hydrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Emergency Medicine (AREA)
- Analytical Chemistry (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Aldehydes are condensed with aromatic ethers or polynuclear aromatic hydrocarbons in an organic solvent inert with respect to aldehydes containing at least 3% by weight of the ether or hydrocarbon of a strong organic acid, the concentration of the acid being maintained throughout the reaction. The aromatic compounds are water-insoluble and polyfunctional with respect to aldehydes and may be substituted but should not contain any groups capable of ion-exchange nor any groups which are water-solubilizing. Suitable ethers are aromaticaliphatic, e.g. anisole; phenetole; phenyl butyl, phenyl isopropyl, naphthyl methyl and naphthyl ethyl ethers; the methyl ether of m-hydroxydiphenyl or of 1,3,5-xylenol; and ethylene or butylene glycol diphenyl ethers. Completely aromatic ethers such as diphenyl oxide or phenyl naphthyl ether including cyclic aromatic ethers, e.g. diphenylene dioxide also are usable. Suitable hydrocarbons are naphthalene, anthracene, phenanthrone, acenaphthene, and methyl naphthalene. The ethers and hydrocarbons may be substituted by halogen, halogenoalkyl, nitro or cyano groups. Lower aliphatic aldehydes, e.g. acetaldehyde or butyraldehyde may be used, but formaldehyde and substances yielding it, e.g. paraformaldehyde and trioxymethylene are preferred. The reaction may be starting using an aliphatic aldehyde such as acetaldehyde and completed using formaldehyde. The strong organic acids have pKa not more than 2.87, e.g. monodi-, and tri-chloroacetic and their bromine analogues; toluene, benzene, chlorobenzene, dichlorobenzene, isopropylbenzene and nitrobenzene sulphonic acids, and 2,6-dichlorophenyl-4 sulphonic acid; methyl, ethyl and propyl sulphonic acids are also suitable. The solvent may be halogenated hydrocarbon, e.g. ethylenedichloride, 1,2-dichloroethane, trichlorethylene, tetrachlorethane, 1,4-dichlorobutane, chlorobenzene, di- and tri-chlorobenzene, and their bromine analogues; phenols substituted by alkyl or halo groups in the 2,4,6 positions, e.g. 2,4,6,-trichloro or 2-chloro-4-nitro-6- methyl phenol; aliphatic hydrocarbons in combination with halogenated hydrocarbons, e.g. n-hexane, n-heptane, neopentane, or isooctane, the hydrocarbon preferably not exceeding 70% of the solvent by volume; or cyclic ethers, e.g. dioxan. The condensation is preferably effected at 70-130 DEG C., the reaction time being 4-24 hours, 1-3 mols. of formaldehyde are preferably used per mol. of aromatic reactant. The preferred reaction conditions are the use of halogenated hydrocarbons and 3-50% of acid based on the aromatic reactant. Water formed during the reaction tends to form a separate layer in which the catalyst dissolves and should therefore be removed, e.g. by distillation, by combination with anhydrous salts, e.g. Na2SO4, or by reaction with acid chlorides or anhydrides, e.g. acetyl chloride or acetic anhydride. The use of solvents such as dioxan or haloacetic acids which dissolve the water and swell the product makes removal of water unnecessary when phenoxyethyl chloride is condensed. The ratio of aromatic reactant to solvent is advantageously 1:0.5 to 1:2. The use of poor solvents such as alcohols, carboxylic acids or aliphatic hydrocarbons, in admixture with good solvents leads to spongy structures for the products. The products may be homogeneous gels, opaque, cloudy gels, permeated by fine pores, or of a sponge-like structure. They may be produced as diaphragms or foils by carrying out the reaction in a suitable cavity, e.g. between glass plates or if acid-resisting fabric e.g. of PVC., polyacrylonitrile, or polyvinylidene chloride is impregnated with the reaction solution and condensation carried out, plasticizers, e.g. dioctyl or dibutyl phthalate, dioctyl sebacate, or tricresyl phosphate improve the elasticity of the diaphragms. The products may be formed as beads by disposal of the organic solvent solution of reactants and acids in an aqueous phase; addition of a strong inorganic acid to the water causes most of the organic acid to remain in the organic phase. Suitable solvents for this procedure are tetrachlorethane, 1,4 dichlorobutane, mono-, di- or trichlorobenzenes, and mono or di bromobenzenes. Alternatively, the reactants may be condensed in organic medium with 3-20% of the organic acid present, then a 20-50% solution of strong inorganic acid in water added, or the reactants condensed in aqueous suspension without an organic solvent but with an organic acid, and an organic solvent added later to break up the organic phase into beads. The presence of the organic solvent causes the molecules of the product to have a loose, open structure although considerably cross-linked, and this allows ready substitution of the resins to form ion-exchangers. Chloromethyl, sulphonic acid and phosphoric acid groups may be readily introduced and further modification, e.g. of halo to amino and then further modification of the amino groups with chloroacetic acid is then possible.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF29604A DE1169666B (en) | 1959-10-14 | 1959-10-14 | Process for the production of high-molecular, infusible and insoluble condensation products which, however, swell in organic solvents |
Publications (1)
Publication Number | Publication Date |
---|---|
GB942057A true GB942057A (en) | 1963-11-20 |
Family
ID=7093385
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB35332/60A Expired GB942057A (en) | 1959-10-14 | 1960-10-14 | Process for the production of cross-linked synthetic resins of high molecular weight |
Country Status (4)
Country | Link |
---|---|
BE (1) | BE596033A (en) |
DE (1) | DE1169666B (en) |
GB (1) | GB942057A (en) |
NL (1) | NL256860A (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3453220A (en) * | 1967-08-14 | 1969-07-01 | Sun Oil Co | Poly (methylenenaphthylene) resin and method of making same |
US3940448A (en) * | 1974-02-25 | 1976-02-24 | The Dow Chemical Company | Formaldehyde-diaromatic ether reaction products |
EP0316140A2 (en) * | 1987-11-10 | 1989-05-17 | Sugio Otani | Thermosetting aromatic resin composition |
EP2810969A4 (en) * | 2012-01-31 | 2015-09-02 | Mitsubishi Gas Chemical Co | Naphthalene-formaldehyde resin, naphthalene-formaldehyde resin with bonds formed by deacetalization, and modified naphthalene-formaldehyde resin |
CN105413658A (en) * | 2015-12-09 | 2016-03-23 | 广东南海普锐斯科技有限公司 | Formaldehyde purification porous adsorption film and preparation method thereof |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE915036C (en) * | 1951-12-08 | 1954-07-15 | Bayer Ag | Process for the production of cation exchangers which contain a weakly acidic exchange-active atom group |
BE548446A (en) * | 1952-06-06 |
-
0
- NL NL256860D patent/NL256860A/xx unknown
-
1959
- 1959-10-14 DE DEF29604A patent/DE1169666B/en active Pending
-
1960
- 1960-10-14 BE BE596033A patent/BE596033A/en unknown
- 1960-10-14 GB GB35332/60A patent/GB942057A/en not_active Expired
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3453220A (en) * | 1967-08-14 | 1969-07-01 | Sun Oil Co | Poly (methylenenaphthylene) resin and method of making same |
US3940448A (en) * | 1974-02-25 | 1976-02-24 | The Dow Chemical Company | Formaldehyde-diaromatic ether reaction products |
EP0316140A2 (en) * | 1987-11-10 | 1989-05-17 | Sugio Otani | Thermosetting aromatic resin composition |
EP0316140A3 (en) * | 1987-11-10 | 1990-07-04 | Sugio Otani | Thermosetting aromatic resin composition |
EP2810969A4 (en) * | 2012-01-31 | 2015-09-02 | Mitsubishi Gas Chemical Co | Naphthalene-formaldehyde resin, naphthalene-formaldehyde resin with bonds formed by deacetalization, and modified naphthalene-formaldehyde resin |
US9200105B2 (en) | 2012-01-31 | 2015-12-01 | Mitsubishi Gas Chemical Company, Inc. | Naphthalene formaldehyde resin, deacetalized naphthalene formaldehyde resin, and modified naphthalene formaldehyde resin |
CN105413658A (en) * | 2015-12-09 | 2016-03-23 | 广东南海普锐斯科技有限公司 | Formaldehyde purification porous adsorption film and preparation method thereof |
CN105413658B (en) * | 2015-12-09 | 2018-09-21 | 广东南海普锐斯科技有限公司 | A kind of porous adsorbed film of purifying formaldehyde and preparation method thereof |
Also Published As
Publication number | Publication date |
---|---|
NL256860A (en) | |
BE596033A (en) | 1961-02-01 |
DE1169666B (en) | 1964-05-06 |
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