GB981813A - Improvements in or relating to polyurea - Google Patents

Improvements in or relating to polyurea

Info

Publication number
GB981813A
GB981813A GB1157261A GB1157261A GB981813A GB 981813 A GB981813 A GB 981813A GB 1157261 A GB1157261 A GB 1157261A GB 1157261 A GB1157261 A GB 1157261A GB 981813 A GB981813 A GB 981813A
Authority
GB
United Kingdom
Prior art keywords
urea
diamine
amine
nonamethylene
water
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
GB1157261A
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.)
Toyo Koatsu Industries Inc
Original Assignee
Toyo Koatsu Industries 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 Toyo Koatsu Industries Inc filed Critical Toyo Koatsu Industries Inc
Publication of GB981813A publication Critical patent/GB981813A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/02Polyureas

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

A substituted urea is formed as an intermediate compound by reaction of a urea compound and a saturated aliphatic diprimary diamine with liberation of ammonia, in a continuous process for the preparation of polyureas (see Division C3). The term "urea compound" denotes urea, thiourea, substituted ureas, substituted thioureas, and diureas and dithioureas, e.g. alkylene diureas and alkylene dithioureas. The diamines include (a) polymethylene diamines having 4 to 12 carbon atoms; (b) hetero-membered diamines e.g. H2N-R1-O -R2-NH2, H2N-R1-S-R2-NH2 and others where R1 and R2 are polymethylene radicals; (c) saturated diamines of the formula <FORM:0981813/C2/1> where n is an integer from 2 to 19 and R stands for H or an alkyl radical, at least one R being alkyl. In example (1) urea, nonamethylene diamine, pelargonic acid amide (viscosity stabilizer) and water are continuously charged to a first reaction zone at 120 DEG C., to give omega-amino-nonamethylene urea as product. In other examples there are reacted (2) 1,8-diamino-2-ethyloctane, urea and palmitic acid; (3) 4,41-diamino-dibutyl ether, urea and pelargonic acid (viscosity stabilizer); (4) nonamethylene diamine carbonate, methylene bis-urea and palmitic acid; (5) urea, nonamethylene diamine, octamethylene diamine and palmitic acid amide; (6) 4,41-diamino-dibutyl sulphide, urea and pelargonic acid amide; (7) nonamethylene diamine, thiourea and water; (8) nonamethylene diamine, urea and palmitic acid amide; (9) nonamethylene diamine, methylene diurea, palmitic acid amide and water. Specification 619,275 is referred to. Reference has been directed by the Comptroller to Specification 864,889.ALSO:A process for manufacturing a spinnable polyurea polymer comprises in a first reaction zone forming a bimolecular condensation product with evolution of ammonia by condensing at least one starting diamine with at least one urea compound in substantially equimolecular proportions at a temperature not higher than 130 DEG C., reacting the said bimolecular condensation compound in the presence of a saturated aliphatic primary amine, the said amine being initially (a) a saturated aliphatic diprimary diamine or (b) an alkyl monoamine having at least three carbon atoms and a boiling-point less than that of the starting diamine or a mixture of the two amines (a) and (b), and thereafter being recycled amine as herein-after mentioned, in a second reaction zone having an inlet maintained at a temperature of about 110 DEG C. to about 130 DEG C. in a first heating area and an outlet maintained at a temperature of about 200 DEG to about 260 DEG C. in a second heating area to form a polyurea prepolymer while evolving gaseous material including vaporous amine, withdrawing polyurea prepolymer from the second reaction zone outlet and thereafter reacting the polyurea prepolymer in a third reaction zone maintained at a temperature from about 200 DEG to 260 DEG C. and at a pressure of 1 to 50 mm. Hg to form the spinnable polyurea polymer while evolving gaseous material including vaporous amine, removing the gaseous amine and recycling a controlled amount of the amine contained therein through the second reaction zone, amine (a) and/or amine (b) being added periodically as required. "Urea compound" means urea, thiourea, substituted ureas or thioureas, diureas and dithioureas and any compound which decomposes to provide such. "Saturated aliphatic diprimary diamine" is meant to include (a) polymethylene diamine; (b) diamines of the formulae H2N-R1-O-R2-NH2, H2N-R1-O-R3-O-R2-NH2, H2N-R1-S-R2NH2 H2N-R1-S-R3-S-R2-NH2 and H2N-R1-S-S-R2-NH2 wherein R1, R2 and R3 stand for a polymethylene radical having 2 to 8 carbon atoms; (c) compounds of the formula <FORM:0981813/C3/1> wherein n is an integer from 2 to 19, R stands for H or an alkyl radical having not more than 10 carbon atoms, at least one R being an alkyl radical. The diamines can be used in the form of their carbonates. Reaction in the first zone can be carried out in the presence of such solvents as water, phenol, cresol or an alcohol. The amount of amine used in the second zone is preferably 2 to 20% by weight of the amount of initial saturated aliphatic primary diamine. A viscosity stabilizer is preferably added in the first or second zone. Suitable are N-acyl-polymethylene diamine, an alkylmonoamide or a saturated aliphatic monocarboxylic acid with at least 3 and preferably 6 carbon atoms in the alkyl or acyl radicals. In Example (1) urea, nonamethylene diamine and pelargonic acid amide (viscosity stabilizer) are reacted in a first zone at 120 DEG C. to give omega-aminononamethylene urea. This is conducted to a second reaction zone comprising heated areas at 130 DEG to 150 DEG C. and 200 DEG to 230 DEG C., ammonia and water being formed in the first area and nonamethylene diamine and CO2 in the second heated area. Product of the second reaction zone is passed to a third reaction zone kept at 250 DEG C. Nonamethylene diamine evolved in the third zone is recycled to the second zone. In other examples the starting materials used are (2) 1,8-diamino-2-ethyloctane, urea, palmitic-acid (viscosity stabilizer), in water; (3) 4,41-diamino -dibutyl ether, urea and pelargonic acid; (4) nonamethylene carbonate, methylene bisurea and palmitic acid; (5) urea, nonamethylene diamine, octamethylene diamine and palmitic acid amide (reacted in m-cresol); (6) 4,41-diamino-dibutyl sulphide, urea and pelargonic acid amide (in water); (7) nonamethylene diamine and thiourea (in water); (8) nonamethylene diamine, urea, and palmitic acid amide (in water); (9) nonamethylene diamine, methylene diurea and palmitic acid amide in water. Specification 619,275 is referred to. Reference has been directed by the Comptroller to Specification 864,889.
GB1157261A 1960-03-30 1961-03-29 Improvements in or relating to polyurea Expired GB981813A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP1016560 1960-03-30
JP1016760 1960-03-30

Publications (1)

Publication Number Publication Date
GB981813A true GB981813A (en) 1965-01-27

Family

ID=26345378

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1157261A Expired GB981813A (en) 1960-03-30 1961-03-29 Improvements in or relating to polyurea

Country Status (1)

Country Link
GB (1) GB981813A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3965072A (en) * 1969-11-28 1976-06-22 Ici United States Inc. Polyurea-urethane polymers from urea, diamines and aminoalcohols
US4154724A (en) * 1976-06-28 1979-05-15 Texaco Development Corp. Polyether polyureides and resinous compositions therefrom
EP0307964A2 (en) * 1987-09-21 1989-03-22 The Dow Chemical Company Amino-functional polyethers containing urea, biuret, thiourea, dithiobiuret, thioamide, and/or amide moieties in their backbone and urethane/urea prepolymers and polymers made therefrom

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3965072A (en) * 1969-11-28 1976-06-22 Ici United States Inc. Polyurea-urethane polymers from urea, diamines and aminoalcohols
US4154724A (en) * 1976-06-28 1979-05-15 Texaco Development Corp. Polyether polyureides and resinous compositions therefrom
EP0307964A2 (en) * 1987-09-21 1989-03-22 The Dow Chemical Company Amino-functional polyethers containing urea, biuret, thiourea, dithiobiuret, thioamide, and/or amide moieties in their backbone and urethane/urea prepolymers and polymers made therefrom
EP0307964A3 (en) * 1987-09-21 1990-05-23 The Dow Chemical Company Amino-functional polyethers containing urea, biuret, thiourea, dithiobiuret, thioamide, and/or amide moieties in their backbone and urethane/urea prepolymers and polymers made therefrom

Similar Documents

Publication Publication Date Title
US3567763A (en) Ester polyisocyanates
US2697118A (en) Totally hydroxypropylated alkylene diamines
US2573673A (en) Method of producing n-mono substituted imidic compounds
GB816280A (en) A method for the preparation of aminoaceto nitriles
GB981813A (en) Improvements in or relating to polyurea
US2252721A (en) Cyclic amidine
US2258321A (en) Condensation products of amines and monoalkylol cyanamides
GB852988A (en) Alkylbenzene diisocyanates
US3641094A (en) Preparation of isocyanates
US2525855A (en) Hexahydro pyrimidine derivatives and process of making same
EP0245631A2 (en) Chemical process for the preparation of oxamide derivatives.
US2334517A (en) High molecular weight surface active amines
US3162673A (en) Bis (aminoaliphatic) carbonates and process for preparation
US3024282A (en) Process for the amidomethylatton of
US2966507A (en) 1, 3-bis (pentaalkyldisiloxanylalkylene) ureas
Beachell et al. Thermal degradation of ethylene bis (N‐phenylcarbamate)
GB1072196A (en) Silylureas
US3468924A (en) Alpha,alpha-difuloroalkylarylmethyl isocyanates
US2424664A (en) N-beta-cyanoethylalkane-sulfonamides
US3049559A (en) Ureas
US2323075A (en) Process of preparing thiuronium salts
GB619275A (en) Manufacture of polymeric ureas
US3714217A (en) Bicyclo(n.1.0)n-alkyl-n&#39;-alkoxy ureas as herbicides
US2868791A (en) Process for the production of substituted piperazines
US2312395A (en) Acylated p-aminobenzyl amines and their quaternary derivatives