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GB804299A - 1, 3-di-(ªÏ-hydroxyalkyl) thioureas - Google Patents

1, 3-di-(ªÏ-hydroxyalkyl) thioureas

Info

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
Application number
GB3149156A
Inventor
Arthur Ferguson Mckay
Martha Skulski
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Monsanto Canada Inc
Original Assignee
Monsanto Canada Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Monsanto Canada Inc filed Critical Monsanto Canada Inc
Priority to GB3149156A priority Critical patent/GB804299A/en
Publication of GB804299A publication Critical patent/GB804299A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30Low-molecular-weight compounds
    • C08G18/38Low-molecular-weight compounds having heteroatoms other than oxygen
    • C08G18/3855Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
    • C08G18/3857Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur having nitrogen in addition to sulfur
    • C08G18/3859Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur having nitrogen in addition to sulfur containing -N-C=S groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C335/00Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C335/04Derivatives of thiourea
    • C07C335/06Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms
    • C07C335/08Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/68Polyesters containing atoms other than carbon, hydrogen and oxygen
    • C08G63/688Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur
    • C08G63/6884Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/6886Dicarboxylic 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.
GB3149156A 1956-10-16 1956-10-16 1, 3-di-(ªÏ-hydroxyalkyl) thioureas Expired GB804299A (en)

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)

* Cited by examiner, † Cited by third party
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

Cited By (3)

* Cited by examiner, † Cited by third party
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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