GB804299A - 1, 3-di-(ªÏ-hydroxyalkyl) thioureas - Google Patents
1, 3-di-(ªÏ-hydroxyalkyl) thioureasInfo
- Publication number
- GB804299A GB804299A GB3149156A GB3149156A GB804299A GB 804299 A GB804299 A GB 804299A GB 3149156 A GB3149156 A GB 3149156A GB 3149156 A GB3149156 A GB 3149156A GB 804299 A GB804299 A GB 804299A
- Authority
- GB
- United Kingdom
- Prior art keywords
- bis
- acid
- thiourea
- polymerized
- formula
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
- C08G18/3857—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur having nitrogen in addition to sulfur
- C08G18/3859—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur having nitrogen in addition to sulfur containing -N-C=S groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/06—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms
- C07C335/08—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms of a saturated carbon skeleton
-
- 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
- C08G63/688—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur
- C08G63/6884—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/6886—Dicarboxylic acids and dihydroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Cosmetics (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
Compounds of formula HO(CH2)nNHCSNH(CH2)nOH (see Groups IV (b)) are condensed with a dicarboxylic acid of formula HOOC-R-COOH, where R is a divalent hydrocarbon radical, or with a 1,3-bis-(o -carboxyalkyl)-urea of formula HOOC(CH2)mNHCONH(CH2)mCOOH where m is 2-17 (see Specification 801,894, [Group IV (b)], in the presence of an acid esterification catalyst such as sulphuric acid, p-toluene sulphonic acid or, preferably, polyphosphoric acid. Preferred acids HOOC-R-COOH are adipic, azelaic, sebacic and tere phthalic acids. The polyesters are low melting wax-like solids. The 1,3-bis-(o -hydroxyalkyl) thioureas may also be reacted with diisocyanates such as hexamethylene or toluene diisocyanate to obtain polythiourea - polyurethanes. In examples: (4) adipic acid is polymerized with 1,3 - bis - (7 - hydroxyheptyl)-thiourea; (5) 1,3-bis-(5-carboxypentyl)-urea is polymerized with 1,3 - bis - (7 - hydroxyheptyl)-thiourea, and (6) adipic acid is polymerized with 1,3-bis-(6-hydroxyhexyl)-thiourea. Specification 804,300 also is referred to.ALSO:The invention comprises novel compounds of the general formula HO(CH2)nNHCSNH(CH2)nOH where n is 5 to 18. They are prepared by reacting carbon disulphide in an inert solvent with substantially two mols. of an o -amino alcohol of formula HO(CH2)nNH2 until evolution of hydrogen sulphide ceases. Preferably a solution of the carbon disulphide is added slowly to the amino alcohol solution, the temperature being maintained at or below room temperature, preferably at about 5 DEG C. After the addition the mixture is agitated at or near room temperature for a further period, preferably about 3 hours, and then heated to reflux for a further period, preferably about 15 hours. The solvent is removed under reduced pressure and the product re-crystallized. The compounds of the invention may be polymerized with dibasic acids (see Group IV (a)). Examples describe the preparation of compounds in which n is 6, 7 and 11. Some e -caprolactam is formed as a by-product when polymerizing 1,3-bis-(7 hydroxyheptyl) - thiourea with 1,3 - bis - (5 - carboxypentyl) - urea. Specifications 801,894 and 804,300 are referred to.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB3149156A GB804299A (en) | 1956-10-16 | 1956-10-16 | 1, 3-di-(ªÏ-hydroxyalkyl) thioureas |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB3149156A GB804299A (en) | 1956-10-16 | 1956-10-16 | 1, 3-di-(ªÏ-hydroxyalkyl) thioureas |
Publications (1)
Publication Number | Publication Date |
---|---|
GB804299A true GB804299A (en) | 1958-11-12 |
Family
ID=10323871
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3149156A Expired GB804299A (en) | 1956-10-16 | 1956-10-16 | 1, 3-di-(ªÏ-hydroxyalkyl) thioureas |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB804299A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3681456A (en) * | 1969-05-26 | 1972-08-01 | Jefferson Chem Co Inc | Thiourea compound |
CN114230606A (en) * | 2020-09-09 | 2022-03-25 | 中国石油天然气股份有限公司 | Compound, corrosion inhibitor composition containing compound, preparation method and application of corrosion inhibitor |
-
1956
- 1956-10-16 GB GB3149156A patent/GB804299A/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3681456A (en) * | 1969-05-26 | 1972-08-01 | Jefferson Chem Co Inc | Thiourea compound |
CN114230606A (en) * | 2020-09-09 | 2022-03-25 | 中国石油天然气股份有限公司 | Compound, corrosion inhibitor composition containing compound, preparation method and application of corrosion inhibitor |
CN114230606B (en) * | 2020-09-09 | 2024-01-30 | 中国石油天然气股份有限公司 | Compound, corrosion inhibitor composition containing compound, preparation method and application of corrosion inhibitor |
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