GB751841A - Derivative products of the urethanes of glycols and processes for the manufacture thereof - Google Patents

Derivative products of the urethanes of glycols and processes for the manufacture thereof

Info

Publication number
GB751841A
GB751841A GB17237/51A GB1723751A GB751841A GB 751841 A GB751841 A GB 751841A GB 17237/51 A GB17237/51 A GB 17237/51A GB 1723751 A GB1723751 A GB 1723751A GB 751841 A GB751841 A GB 751841A
Authority
GB
United Kingdom
Prior art keywords
type
ester
isocyanate
ethylene glycol
hexamethylene
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
GB17237/51A
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.)
Compagnie de Saint Gobain SA
Original Assignee
Compagnie de Saint Gobain SA
Manufactures des Glaces et Produits Chimiques de Saint Gobain SA
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 Compagnie de Saint Gobain SA, Manufactures des Glaces et Produits Chimiques de Saint Gobain SA filed Critical Compagnie de Saint Gobain SA
Publication of GB751841A publication Critical patent/GB751841A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

The invention comprises (1) reacting carbamate esters of glycols with organic isocyanates; (2) the products of (1) of the following-types: <FORM:0751841/IV(a)/1> <FORM:0751841/IV(a)/2> <FORM:0751841/IV(a)/3> <FORM:0751841/IV(a)/4> <FORM:0751841/IV(a)/5> <FORM:0751841/IV(a)/6> <FORM:0751841/IV(a)/7> <FORM:0751841/IV(a)/8> where R and R1 are aliphatic hydrocarbon radicals (same or different), R1 and R11 are hydrogen, alkyl, aryl, aralkyl or cycloalkyl, R2 is alkyl, aryl, aralkyl or cycloalkyl, and R3 is alkylene, arylene, aralkylene or cycloalkylene; and (3) products of (1) of the formula <FORM:0751841/IV(a)/9> where the radicals are in (2) with the proviso that if one of R1 and R11 is hydrogen the other of these is different from R2. The nature of the products depends on the proportions of the reactants, temperature, duration of heating and presence or absence of solvents. Reaction may occur at the nitrogen atom as well as the oxygen atom to give allophanates, the production of the latter being favoured by temperatures above 100 DEG C., while simple glycol esters are usually formed at lower temperatures. The mixed urethane-allophanates IV are obtained by carrying out the reaction first at a low then a high temperature. The cyclic compounds VII result from further heating of the products V and VI (e.g. to 100-120 DEG C.). In the examples: (1) ethylene glycol mono-N-ethylcarbamic ester and phenyl isocyanate give a product of type IX; (2) type IX from ethylene glycol mono-N:N-dibutylcarbamic ester; (3) type IX from ethylene glycol monocarbamic ester and phenyl isocyanate; (4) type IX from ethylene glycol mono - (piperidine - N - carboxylic) ester and phenyl isocyanate; (5) type IX from b -hydroxyisopropyl carbamate and phenyl isocyanate; (6) type IX from b -hydroxyisopropyl N-ethylcarbamate and phenyl isocyanate; (7) type I from ethylene glycol monocarbamic ester and hexamethylene di-isocyanate; (8) type I from ethylene glycol mono-N:N-diethylcarbamic ester and hexa-methylene di-isocyanate; (9) type I from ethylene glycol mono-N:N-dibutylcarbamic ester and hexamethylene di-isocyanate; (10) type I from ethylene glycol monocarbamic ester and toluylene di-isocyanate; (11) type I from b -hydroxyisopropyl carbamate and hexamethylene di-isocyanate; (12) type I from b - hydroxyisopropyl N - ethylcarbamate and hexamethylene di-isocyanate; (13) type I from b -hydroxyisopropyl carbamate and toluylene di-isocyanate; (14) type I from ethylene diamine N:N1-dicarboxylic di-(b -hydroxyethyl) ester and phenyl isocyanate; (15) type VIII from hydrazine N:N1 - dicarboxylic di - (b - hydroxyethyl) ester and phenyl isocyanate; (16) type I from hexa-methylenediamine N:N1-dicarboxylic di - (b - hydroxyethyl) ester and phenyl isocyanate; (17) type II from ethylene glycol di-(N-b -hydroxyethylcarbamic) ester and phenyl isocyanate; (18) type III from ethylene glycol mono-N-ethylcarbamic ester and toluylene di-isocyanate; (19) type IV (with some type I) from ethylene glycol monocarbamic ester and toluylene di-isocyanate; (20) type IV from ethylene glycol mono-N-methylcarbamic ester and toluylene di-isocyanate; (21) type III from ethylene glycol monocarbamic ester and hexamethylene di-isocyanate; (22) type III from ethylene glycol mono N-ethylcarbamic ester and hexamethylene di-isocyanate; (23) type V from ethylene glycol monocarbamic ester and toluylene di-isocyanate; further heating converts it to type VII; (24) type V from ethylene glycol mono-N-ethylcarbamic ester and toluylene diisocyanate; (25) type VII from ethylene glycol N-ethylcarbamic ester and hexamethylene diisocyanate; (26) type VI from ethylene glycol mono-N-ethylcarbamic ester and hexamethylene-di-isocyanate; further heating converts it to type VII; (27) type V from ethylene glycol mono-N:N-diethylcarbamic ester and hexamethylene di-isocyanate; (28) type V from b -hydroxyisopropyl carbamate and hexamethylene di-isocyanate; further heating converts it to type VII. Reference has been directed by the Comptroller to Specification 689,705.
GB17237/51A 1950-09-15 1951-07-20 Derivative products of the urethanes of glycols and processes for the manufacture thereof Expired GB751841A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR751841X 1950-09-15

Publications (1)

Publication Number Publication Date
GB751841A true GB751841A (en) 1956-07-04

Family

ID=9156438

Family Applications (1)

Application Number Title Priority Date Filing Date
GB17237/51A Expired GB751841A (en) 1950-09-15 1951-07-20 Derivative products of the urethanes of glycols and processes for the manufacture thereof

Country Status (1)

Country Link
GB (1) GB751841A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3669991A (en) * 1967-07-04 1972-06-13 Bayer Ag N-aryl-substituted dialkanolamino-polyurethanes
US5466789A (en) * 1992-01-21 1995-11-14 Du Pont (Uk) Limited Polyunsaturated diazonium compounds
US5534623A (en) * 1993-01-21 1996-07-09 Du Pont (Uk) Limited Process for preparing a polyunsaturated diazonium compounds

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3669991A (en) * 1967-07-04 1972-06-13 Bayer Ag N-aryl-substituted dialkanolamino-polyurethanes
US5466789A (en) * 1992-01-21 1995-11-14 Du Pont (Uk) Limited Polyunsaturated diazonium compounds
US5534623A (en) * 1993-01-21 1996-07-09 Du Pont (Uk) Limited Process for preparing a polyunsaturated diazonium compounds

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