GB620116A - Improvements in or relating to the manufacture of nitrogen-containing linear polymers - Google Patents

Improvements in or relating to the manufacture of nitrogen-containing linear polymers

Info

Publication number
GB620116A
GB620116A GB225739A GB225739A GB620116A GB 620116 A GB620116 A GB 620116A GB 225739 A GB225739 A GB 225739A GB 225739 A GB225739 A GB 225739A GB 620116 A GB620116 A GB 620116A
Authority
GB
United Kingdom
Prior art keywords
isocyanate
acid
hexamethylene
glycol
tetramethylene
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
GB225739A
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.)
Henry Dreyfuss Associates
Original Assignee
Henry Dreyfuss Associates
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 Henry Dreyfuss Associates filed Critical Henry Dreyfuss Associates
Priority to GB225739A priority Critical patent/GB620116A/en
Priority claimed from US782213A external-priority patent/US2568885A/en
Publication of GB620116A publication Critical patent/GB620116A/en
Priority claimed from US11576649 external-priority patent/US2623867A/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
    • C08G18/70Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/701Compounds forming isocyanates or isothiocyanates in situ
    • 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
    • C08G18/32Polyhydroxy compounds; Polyamines; Hydroxyamines
    • 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
    • C08G18/70Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72Polyisocyanates or polyisothiocyanates
    • C08G18/80Masked polyisocyanates
    • C08G18/8061Masked polyisocyanates masked with compounds having only one group containing active hydrogen
    • C08G18/8064Masked polyisocyanates masked with compounds having only one group containing active hydrogen with monohydroxy compounds
    • C08G18/8067Masked polyisocyanates masked with compounds having only one group containing active hydrogen with monohydroxy compounds phenolic compounds

Abstract

Nitrogen-containing linear polymers are produced by reacting a di-isocyanate or a di-urethane with a bifunctional reagent containing as one reactive function a hydroxy or carboxy group and as the other a hydroxy, carboxy or amino group. Suitable reactants mentioned are o -amino-caproic acid, o -amino-caprylic acid, o -amino-nonanoic acid, glutaric acid, adipic acid, suberic acid, azelaic acid, sebacic acid, brassylic acid, hexahydroterephthalic acid, trimethylene glycol, tetramethylene glycol, ethanolamine, the propanolamines and the butanolamines. The two urethane or isocyanate groups of the other component of the reaction mixture may be joined by a polymethylene chain which may be interrupted by an oxygen, sulphur or other atom. The complementary reactive radicals in the reaction mixture should be present in substantially equivalent proportions if filament- or film-forming polymers are required. Reaction is effected by heating above 100 DEG C. with reduced pressure if desired in the later stages. Removal of volatile by-products may be assisted by passing an inert gas through the mixture. The reaction may be performed in presence of a solvent for the reagents. The products may be formed into shaped articles. The di-urethanes may be produced from the corresponding diamines and a carbonate, e.g. phenyl carbonate; or from the corresponding di-isocyanate or di-carbonyl chloride with a hydroxy compound, e.g. a volatile phenol; or from the appropriate diazide and a hydroxy compound. Samples have been furnished under Sect. 2(5) of polymers prepared from (1) and (2) octamethylene di-urethane and ethanolamine; (3) hexamethylene diphenyl urethane and hexamethylene glycol; (4) m-toluylene diphenyl urethane and hexamethylene glycol; (5) tetramethylene di-isocyanate and hexamethylene glycol; (6) hexamethylene di-isocyanate and hexamethylene glycol; (7) hexamethylene di-isocyanate and 1.4-butylene glycol; (8) hexamethylene di-isocyanate and decamethylene glycol; (9) m-toluylene di-isocyanate and hexamethylene glycol; (10) tetramethylene di-isocyanate and p-hydroxybenzoic acid; (11) tetramethylene di-isocyanate and lactic acid; (12) tetramethylene di-isocyanate and sebacic acid; (13) hexamethylene di-isocyanate and -aminocaproic acid; (14) hexamethylene di-isocyanate and aminopivalic acid. The urethanes used for the samples were obtained from the corresponding di-isocyanate and phenol. Tetramethylene di-isocyanate was made by the Curtius process from adipic dihydrazide.ALSO:Nitrogen-containing linear polymers are produced by reacting a di-isocyanate or a diurethane with a bifunctional reagent containing as one reaction function a hydroxy or carboxy group and as the other a hydroxy, carboxy or amino group. Suitable reactants mentioned are o -amino-caproic acid, o -amino-caprylic acid, o -amino-nonanoic acid, glutaric acid, adipic acid, suberic acid, azelaic acid, sebacic acid, brassylic acid, hexahydroterephthalic acid, trimethylene glycol, tetramethylene glycol, ethanolamine, the propanolamines and the butanolamines. The two methane or isocyanate groups of the other component of the reaction mixture may be joined by a polymethylene chain which may be interrupted by an oxygen, sulphur or other atom. The complementary reaction radicals in the reaction mixture should be present in substantially equivalent proportions if filament- or film-forming polymers are required. Reaction is effected by heating above 100 DEG C. with reduced pressure if desired in the later stages. Removal of volatile by-products may be assisted by passing an inert gas through the mixture. The reaction may be performed in presence of a solvent for the reagents. The products may be formed into shaped articles. The diurethanes may be produced from the corresponding diamines and a carbonate, e.g. phenyl carbonate; or from the corresponding di-isocyanate or dicarbamyl chloride with a hydroxy compound, e.g. a volatile phenol; or from the appropriate diazide and a hydroxy compound. Samples have been furnished under Sect. 2(5) of polymers prepared from 1- and 2-octamethylene diurethane and ethanolamine; (3) hexamethylene diphenyl urethane and hexamethylene glycol; (4) m-toluylene diphenyl urethane and hexamethylene glycol; (5) tetramethylene di-isocyanate and hexamethylene glycol; (6) hexamethylene di-isocyanate and hexamethylene glycol; (7) hexamethylene di-isocyanate and 1.4-butylene glycol; (8) hexamethylene di-isocyanate and decamethylene glycol; (9) m-toluylene di-isocyanate and hexamethylene glycol; (10) tetramethylene di-isocyanate and p-hydroxybenzoic acid; (11) tetramethylene di-isocyanate and lactic acid; (12) tetramethylene di-isocyanate and sebacic acid; (13) hexamethylene di-isocyanate and b -aminocaproic acid; (14) hexamethylene di-isocyanate and aminopivalic acid. The urethanes used for the samples were obtained from the corresponding di-isocyanates and phenol. Tetramethylene di-isocyanate was made by the Curtius process from adipic dihydrazide.
GB225739A 1939-01-23 1939-01-23 Improvements in or relating to the manufacture of nitrogen-containing linear polymers Expired GB620116A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB225739A GB620116A (en) 1939-01-23 1939-01-23 Improvements in or relating to the manufacture of nitrogen-containing linear polymers

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB225739A GB620116A (en) 1939-01-23 1939-01-23 Improvements in or relating to the manufacture of nitrogen-containing linear polymers
US782213A US2568885A (en) 1939-01-23 1947-10-25 Manufacture of high polymeric compounds from n, n'-dicarbophenoxy-2, 4-diamino toluene and hexamethylene glycol
US11576649 US2623867A (en) 1939-01-23 1949-09-14 Manufacture of polyurea-urethanes

Publications (1)

Publication Number Publication Date
GB620116A true GB620116A (en) 1949-03-21

Family

ID=9736358

Family Applications (1)

Application Number Title Priority Date Filing Date
GB225739A Expired GB620116A (en) 1939-01-23 1939-01-23 Improvements in or relating to the manufacture of nitrogen-containing linear polymers

Country Status (1)

Country Link
GB (1) GB620116A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2733261A (en) * 1956-01-31 N-akylisocyanates of a-phenyl ethyl-
US2797232A (en) * 1953-04-02 1957-06-25 Bayer Ag Hidden polyisocyanates
WO2007066345A1 (en) * 2005-12-09 2007-06-14 Council Of Scientific & Industrial Research A melt transurethane process for the preparation of polyurethanes

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2733261A (en) * 1956-01-31 N-akylisocyanates of a-phenyl ethyl-
US2797232A (en) * 1953-04-02 1957-06-25 Bayer Ag Hidden polyisocyanates
WO2007066345A1 (en) * 2005-12-09 2007-06-14 Council Of Scientific & Industrial Research A melt transurethane process for the preparation of polyurethanes
GB2445531A (en) * 2005-12-09 2008-07-09 Council Scient Ind Res A melt transurethane process for the preparation of polyurethanes
GB2445531B (en) * 2005-12-09 2010-06-30 Council Scient Ind Res A melt transurethane process for the preparation of polyurethanes

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