GB467571A - Improvements in the manufacture and production of condensation products - Google Patents
Improvements in the manufacture and production of condensation productsInfo
- Publication number
- GB467571A GB467571A GB3486435A GB3486435A GB467571A GB 467571 A GB467571 A GB 467571A GB 3486435 A GB3486435 A GB 3486435A GB 3486435 A GB3486435 A GB 3486435A GB 467571 A GB467571 A GB 467571A
- Authority
- GB
- United Kingdom
- Prior art keywords
- product
- ethylene oxide
- further reacted
- dihydroabietinol
- heated
- 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
- 239000007859 condensation product Substances 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 2
- 239000000047 product Substances 0.000 abstract 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 4
- 239000011347 resin Substances 0.000 abstract 4
- 229920005989 resin Polymers 0.000 abstract 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 2
- -1 abietinol Chemical class 0.000 abstract 2
- 230000001070 adhesive effect Effects 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 abstract 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 abstract 1
- JTAXUBKTCAOMTN-UHFFFAOYSA-N Abietinol Natural products CC(C)C1=CC2C=CC3C(C)(CO)CCCC3(C)C2CC1 JTAXUBKTCAOMTN-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 abstract 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 abstract 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract 1
- 239000004902 Softening Agent Substances 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 1
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 abstract 1
- GQRUHVMVWNKUFW-LWYYNNOASA-N abieta-7,13-dien-18-ol Chemical compound OC[C@]1(C)CCC[C@]2(C)[C@@H](CCC(C(C)C)=C3)C3=CC[C@H]21 GQRUHVMVWNKUFW-LWYYNNOASA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 239000000853 adhesive Substances 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 238000004061 bleaching Methods 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002270 dispersing agent Substances 0.000 abstract 1
- 238000004043 dyeing Methods 0.000 abstract 1
- 238000005187 foaming Methods 0.000 abstract 1
- OTGHWLKHGCENJV-UHFFFAOYSA-N glycidic acid Chemical compound OC(=O)C1CO1 OTGHWLKHGCENJV-UHFFFAOYSA-N 0.000 abstract 1
- 235000013905 glycine and its sodium salt Nutrition 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000004922 lacquer Substances 0.000 abstract 1
- 150000002689 maleic acids Chemical class 0.000 abstract 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical class O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract 1
- 239000000155 melt Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 210000002741 palatine tonsil Anatomy 0.000 abstract 1
- 239000002304 perfume Substances 0.000 abstract 1
- 239000001632 sodium acetate Substances 0.000 abstract 1
- 235000017281 sodium acetate Nutrition 0.000 abstract 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 229940014800 succinic anhydride Drugs 0.000 abstract 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical class OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
- C08G63/6854—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen derived from polycarboxylic acids and polyhydroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polyethers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Condensation products are obtained by reacting resin alcohols, e.g. abietinol, di- and tetrahydroabietinol, or resin amines, e.g. abietinylmethylamine or their acyl derivatives, e.g. acetyl-abietinylamine, containing the groups --NH-- or NH2, with alkylene oxides, e.g. ethylene-, propylene- or butylene oxides, epichlorhydrin, glycide or glycidic acid. The process is preferably carried out while heating and, if desired, with the addition of alkalinereacting or reactive substances having catalytic action, e.g. sodium hydroxide, potassium hydroxide, sodium acetate, sodium ethylate, bleaching earth, e.g. tonsil, or active carbon. The products may be used as alcohol-soluble resins, softening-agents for lacquers &c., carriers for perfumes and dispersing agents. Products with free terminal hydroxyl groups may be further reacted, e.g. with sulphonating agents, e.g. sulphuric or chlorsulphonic acids, or condensed with carboxylic acids, e.g. chloracetic acid, glycocoll or maleic acids. In examples: (1) dihydroabietinol is heated with potassium hydroxide to 120--160 DEG C. in a stirring autoclave and ethylene oxide is pressed into the melt in portions under a pressure of 2--10 atmospheres to produce a sticky resin soluble in alcohol, which may be further reacted with phthalic or maleic anhydrides; (2) dihydroabietinol is heated with potassium ethylate to 150--160 DEG C. and ethylene oxide is led in a little at a time in the gas phase to produce a wax-like product which may be further reacted with succinic anhydride to yield a product having good adhesive properties; (3) a resinous, adhesive product is obtained from dihydroabietinol and epichlorhydrin which product may be further reacted with trimethylamine; (4) a mixture of di- and tetra-hydroabietinol, heated with sodium hydroxide to 170 DEG C. is treated with ethylene oxide under pressure to produce a wax-like product or, with increased quantities of ethylene oxide, a water-soluble product useful as a non-foaming levelling agent for dyeing.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3486435A GB467571A (en) | 1935-12-16 | 1935-12-16 | Improvements in the manufacture and production of condensation products |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3486435A GB467571A (en) | 1935-12-16 | 1935-12-16 | Improvements in the manufacture and production of condensation products |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB467571A true GB467571A (en) | 1937-06-16 |
Family
ID=10370851
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3486435A Expired GB467571A (en) | 1935-12-16 | 1935-12-16 | Improvements in the manufacture and production of condensation products |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB467571A (en) |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2519780A (en) * | 1949-08-11 | 1950-08-22 | Monsanto Chemicals | Herbicidal formulations |
| US2555901A (en) * | 1949-12-01 | 1951-06-05 | Hercules Powder Co Ltd | Reaction products of petroleum hydrocarbon-insoluble pine-wood resin and ethylene oxide |
| US2610966A (en) * | 1949-10-17 | 1952-09-16 | Hollingshead Corp | Process for treating tall oil with alkylene oxides |
| US2623870A (en) * | 1950-01-10 | 1952-12-30 | Gen Aniline & Film Corp | Quaternary ammonium salts |
| US2666017A (en) * | 1950-07-14 | 1954-01-12 | Monsanto Chemicals | Nutrient media containing antifoaming agents |
| US2683089A (en) * | 1952-06-10 | 1954-07-06 | American Cyanamid Co | Bibulous sheet |
| US2683088A (en) * | 1952-06-10 | 1954-07-06 | American Cyanamid Co | Soft bibulous sheet |
| US2703797A (en) * | 1949-12-15 | 1955-03-08 | Gen Aniline & Film Corp | Surface-active compositions |
| US2724700A (en) * | 1951-07-03 | 1955-11-22 | Atlas Powder Co | Solid compositions containing urea and polyoxyethylene ethers of resin alcohols |
| US2742455A (en) * | 1951-09-24 | 1956-04-17 | Gen Aniline & Film Corp | Production of n, n-polyoxyethylated rosin amines |
| US2744888A (en) * | 1950-08-04 | 1956-05-08 | American Cyanamid Co | Ethenoxy n-monoethanolamides of tall oil |
| US2775528A (en) * | 1950-04-08 | 1956-12-25 | Int Paper Canada | Manufacture of cellulose |
| US2778814A (en) * | 1957-01-22 | Alkyl aryl sulfonic acid amine salt | ||
| GB2172005A (en) * | 1985-03-04 | 1986-09-10 | Union Camp Corp | Alkoxylated rosin amides |
-
1935
- 1935-12-16 GB GB3486435A patent/GB467571A/en not_active Expired
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2778814A (en) * | 1957-01-22 | Alkyl aryl sulfonic acid amine salt | ||
| US2519780A (en) * | 1949-08-11 | 1950-08-22 | Monsanto Chemicals | Herbicidal formulations |
| US2610966A (en) * | 1949-10-17 | 1952-09-16 | Hollingshead Corp | Process for treating tall oil with alkylene oxides |
| US2555901A (en) * | 1949-12-01 | 1951-06-05 | Hercules Powder Co Ltd | Reaction products of petroleum hydrocarbon-insoluble pine-wood resin and ethylene oxide |
| US2703797A (en) * | 1949-12-15 | 1955-03-08 | Gen Aniline & Film Corp | Surface-active compositions |
| US2623870A (en) * | 1950-01-10 | 1952-12-30 | Gen Aniline & Film Corp | Quaternary ammonium salts |
| US2775528A (en) * | 1950-04-08 | 1956-12-25 | Int Paper Canada | Manufacture of cellulose |
| US2666017A (en) * | 1950-07-14 | 1954-01-12 | Monsanto Chemicals | Nutrient media containing antifoaming agents |
| US2744888A (en) * | 1950-08-04 | 1956-05-08 | American Cyanamid Co | Ethenoxy n-monoethanolamides of tall oil |
| US2724700A (en) * | 1951-07-03 | 1955-11-22 | Atlas Powder Co | Solid compositions containing urea and polyoxyethylene ethers of resin alcohols |
| US2742455A (en) * | 1951-09-24 | 1956-04-17 | Gen Aniline & Film Corp | Production of n, n-polyoxyethylated rosin amines |
| US2683088A (en) * | 1952-06-10 | 1954-07-06 | American Cyanamid Co | Soft bibulous sheet |
| US2683089A (en) * | 1952-06-10 | 1954-07-06 | American Cyanamid Co | Bibulous sheet |
| GB2172005A (en) * | 1985-03-04 | 1986-09-10 | Union Camp Corp | Alkoxylated rosin amides |
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