GB804300A - 1, 3-di-(ªÏ-hydroxyalkyl)-ureas - Google Patents

1, 3-di-(ªÏ-hydroxyalkyl)-ureas

Info

Publication number
GB804300A
GB804300A GB3149256A GB3149256A GB804300A GB 804300 A GB804300 A GB 804300A GB 3149256 A GB3149256 A GB 3149256A GB 3149256 A GB3149256 A GB 3149256A GB 804300 A GB804300 A GB 804300A
Authority
GB
United Kingdom
Prior art keywords
compounds
prepared
nnhconh
hydroxyalkyl
compound
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
GB3149256A
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 GB3149256A priority Critical patent/GB804300A/en
Publication of GB804300A publication Critical patent/GB804300A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
    • C07C275/06—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
    • C07C275/10—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton being further substituted by singly-bound oxygen atoms
    • 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
    • C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
    • C08G18/3823—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing -N-C=O groups
    • C08G18/3829—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing -N-C=O groups containing ureum groups
    • 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
    • C08G63/6856—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)
  • Polyurethanes Or Polyureas (AREA)

Abstract

Linear polyurea-polyesters of the general formula HO[(CH2)nNHCONH(CH2)nOCORCOO]xH where n is 5 to 18 and R is a divalent hydrocarbon radical are prepared by reacting substantially equimolecular proportions of a compound HO(CH2)nNHCONH(CH2)nOH and a compound HOOC-R-COOH in the presence of an esterification catalyst, preferably polyphosphoric acid. Preferred dicarboxylic acids are adipic, azelaic, sebacic and terephthalic acids. The dicarboxylic acid may also be a compound HOOC(CH2)mNHCONH(CH2)mCOOH in which m is 2 to 17. The hydroxyalkyl ureas may also be reacted with diisocyanates, e.g. hexamethylene- or toluene-diisocyanate to yield polyurea-polyurethanes. In examples, adipic acid is reacted with hydroxyalkyl ureas in which n is 6 and 7. Specifications 801,894, [Group IV (b)], and 804,299 are referred to.ALSO:The invention comprises compounds of the general formula HO HO(CH2)nNHCONH(CH2)nOH, where n is 5 to 18. The compounds with n 5 to 8 are prepared by reacting a 1,3-bis (o -hydroxyalkyl)-thiourea in an alcoholic alkaline solution with hydrogen peroxide, filtering off the precipitated salt, and recovering the product from the filtrate by evaporation to dryness or by the addition of water. The compounds of the invention in which n is 9 to 18 may be prepared by the method of Kjaer et al., Acta Chem. Scand., 7, 518 (1953). In examples, compounds are prepared in which n is 5, 6, 7 and 11. The compounds may be polymerized with dibasic acids (see Group IV (a)). Specifications 801,894 and 804,299 are referred to.
GB3149256A 1956-10-16 1956-10-16 1, 3-di-(ªÏ-hydroxyalkyl)-ureas Expired GB804300A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3149256A GB804300A (en) 1956-10-16 1956-10-16 1, 3-di-(ªÏ-hydroxyalkyl)-ureas

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3149256A GB804300A (en) 1956-10-16 1956-10-16 1, 3-di-(ªÏ-hydroxyalkyl)-ureas

Publications (1)

Publication Number Publication Date
GB804300A true GB804300A (en) 1958-11-12

Family

ID=10323883

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3149256A Expired GB804300A (en) 1956-10-16 1956-10-16 1, 3-di-(ªÏ-hydroxyalkyl)-ureas

Country Status (1)

Country Link
GB (1) GB804300A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3150179A (en) * 1962-05-23 1964-09-22 Hercules Powder Co Ltd Preparation of norbornyl urea by chlorinolysis of norbornyl thiourea
US3277027A (en) * 1962-09-19 1966-10-04 Bayer Ag Polyurethane plastics prepared from a nitrogen containing polyol
US3368985A (en) * 1965-03-19 1968-02-13 Pittsburgh Plate Glass Co Polyurethanes produced from hydroxyl-terminated carbamates
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 (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3150179A (en) * 1962-05-23 1964-09-22 Hercules Powder Co Ltd Preparation of norbornyl urea by chlorinolysis of norbornyl thiourea
US3277027A (en) * 1962-09-19 1966-10-04 Bayer Ag Polyurethane plastics prepared from a nitrogen containing polyol
US3368985A (en) * 1965-03-19 1968-02-13 Pittsburgh Plate Glass Co Polyurethanes produced from hydroxyl-terminated carbamates
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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