GB844525A - Improvements in or relating to the manufacture of polymeric materials - Google Patents

Improvements in or relating to the manufacture of polymeric materials

Info

Publication number
GB844525A
GB844525A GB130857A GB130857A GB844525A GB 844525 A GB844525 A GB 844525A GB 130857 A GB130857 A GB 130857A GB 130857 A GB130857 A GB 130857A GB 844525 A GB844525 A GB 844525A
Authority
GB
United Kingdom
Prior art keywords
acid
salt
diisocyanates
sulphonic acid
groups
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
GB130857A
Inventor
John Francis Wood
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB130857A priority Critical patent/GB844525A/en
Publication of GB844525A publication Critical patent/GB844525A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/0014Use of organic additives
    • C08J9/0033Use of organic additives containing sulfur
    • 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
    • C08G18/08Processes
    • C08G18/16Catalysts
    • C08G18/18Catalysts containing secondary or tertiary amines or salts thereof
    • C08G18/1875Catalysts containing secondary or tertiary amines or salts thereof containing ammonium salts or mixtures of secondary of tertiary amines and acids
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2375/00Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
    • C08J2375/04Polyurethanes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)

Abstract

A process for the manufacture of blown, cellular polyurethanes by the reaction of a polyisocyanate with water and a hydroxyl-containing polymeric material, such as a polyester or polyether, is characterised in that there is incorporated therein a preformed tertiary amine salt of a compound containing one or more-SO3H or OSO3H groups and a hydrocarbon radical containing at least 12-carbon atoms. The salt can be prepared in the anhydrous state or in water either from stoichiometric proportions of its components or with an excess of one component. Specified compounds containing-SO3H or -OSO3 H groups are dodecylsulphuric acid, oleyl-p-anisidine sulphonic acid, dodecyl benzene sulphonic acid, sulphuric acid esters of long chain alcohols such as cetyl alcohol, dinaphthyl methane disulphonic acid, diisopropyl naphthalene sulphonic acid and the sulphated methyl ester of oleic acid. The tertiary amine may contain substituents, for example carboxyl, urethane, urea, keto, amide or hydroxyl groups or hetero atoms or heterocyclic rings. Specified are triethylamine, triethanolamine, b -diethylamino ethanol, bis-(b -diethylaminoethyladipate, b -diethylaminoethyl benzoate, b -diethylaminopropionitrile, dimethyl octadecylamine, N-dimethyl cyclohexylamine and N-dimethylbenzylamine. The salts may be added as such or as aqueous solutions, pastes or emulsions. Amine soaps, e.g. diethylamine oleate and diethylamino ethanol ricinoleate may also be present in the reaction mixture. Fillers, colouring matters, flame-proofing agents may be added to the reaction mixture as dry powders or as pastes with, for example, the hydroxyl containing material, the polyisocyanate, tricresylphosphate or water. Iron compounds and organopolysiloxanes can also be added. In examples foams are obtained from (1) a diethylene glycol/pentaerythritol/adipic acid polyester, toluene 2:4- and 2:6-diisocyanates and an aqueous mixture obtained by neutralising 1-dodecyl sulphuric acid with N-dimethyl cyclohexylamine; (2) a diethylene glycol/glycerol/adipic acid polyester, tolylene 2:4 and 2:6-diisocyanates and an aqueous mixture of the neutralisation product of N-oleyl p-anisidine sulphonic acid with 2diethylaminoethanol; (3) a polypropylene glycol/trimethylol propane/tolylene 2:4 + 2:6-diisocyanate prepolymer, further tolylene diisocyanates and an aqueous mixture of the salt of-b diethylaminoethanol and the sulphated methyl ester of oleic acid. Specifications 553,733, 770,632, 790,420 and 839,183 are referred to.ALSO:Catalysts for use in the production of polyurethanes (see Groups IV(a) and V) comprise a preformed tertiary amine salt of a compound containing one or more -SO3H or -OSO3H groups and a hydrocarbon radical containing at least 12 carbon atoms. For the latter are specified dodecyl-sulphuric acid, oleyl-p-anisidine sulphuric acid, dodecylbenzene sulphonic acid, sulphuric acid esters of long chain alcohols such as cetyl alcohol, dinaphthyl methane disulphonic acid, diisopropyl naphthalene sulphonic acid and the sulphated methyl ester of oleic acid. The tertiary amine may contain substituents, for example carboxyl, urethane, urea, keto, amide or hydroxyl groups or hetero atoms or hetero-cyclic rings. Specified are triethylamine, triethanolamine, b -diethylaminoethanol, bis-(b -diethyl-aminoethyl) adipate, b -diethylaminoethyl benzoate, b -diethyl aminopropionitrile, dimethyl octadecylamine, N-dimethylcyclohexylamine and N-dimethylbenzylamine. In examples the salts employed are prepared from (1) 1-dodecyl sulphuric acid and N-dimethyl cyclohexylamine, (2) N-oleyl p-anisidine sulphonic acid and 2-diethyl-aminoethanol; (3) the sulphated methyl ester of oleic acid and b -diethylaminoethanol. Specification 790,420 is referred to.ALSO:A process for the manufacture of blown, cellular polyurethanes by the reaction of a polyisocyanate with water and a hydroxy-containing polymeric material, such as a polyester or polyether is characterised in that there is incorporated therein a preformed tertiary amine salt of a compound containing one or more -SO3H or -OSO3H groups and a hydrocarbon radical containing at least 12 carbon atoms. The salt can be prepared in the anhydrous state or in water either from stoichiometric proportions or with an excess of one component. Specified compounds containing -SO3H or -OSO3H groups are dodecyl-sulphuric acid, oleyl-p-anisidine sulphonic acid, dodecyl benzene sulphonic acid, sulphuric acid esters of long chain alcohols such as cetyl alcohol, dinaphthyl methane disulphonic acid, diisopropyl naphthalene sulphonic acid and the sulphated methyl ester of oleic acid. The tertiary amine may contain substituents, for example carboxyl, urethane, urea, keto, amide or hydroxyl groups or hetero atoms or heterocyclic rings. Specified are triethylamine, triethanolamine, b -diethyl-aminoethanol, bis p (b -diethylaminoethyl) adipate, b -diethylaminoethyl benzoate, b -diethylaminopropionitrile, dimethyl octadecylamine, N-dimethylcyclohexyl-amine and N-dimethylbenzylamine. The salts may be added as such or as aqueous solutions, pastes or emulsions. Amine soaps e.g. diethylamine oleate and diethylamino-ethanol ricinoleate may also be present in the reaction mixture. Fillers, colouring matters, flame proofing agents may be added as dry powders or mixed with a reortant, tricresyl phosphate or water. Iron compounds and organopolysiloxones can also be added. In examples foams are obtained from (1) a diethylene glycol/pentoereythritol/adipic acid polyester, toluene 2 : 4- and 2 : 6- diisocyanates and the aqueous solution of the salt of 1-dodecyl sulphuric acid with N-dimethyl cyclohexyl-amine; (2) a diethylene glycol/glycerol/adipic acid polyester, tolylene 2 : 4- and 2 : 6 diisocyanates, water and the salt of N-oleryl-p-anisidine sulphonic acid with 2-diethyl-aminoethanol; (3) a polypropylene glycol/trimethylol propane/tolylene 2 : 4 and 2 : 6- diisocyanates prepolymer, further tolylene diisocyanates and an aqueous mixture of the salt of b -diethylaminoethanol and the sulphonated methyl ester of oleic acid. Specifications 553,733, 770,632, 790,420 and 839,183 are referred to.
GB130857A 1957-01-14 1957-01-14 Improvements in or relating to the manufacture of polymeric materials Expired GB844525A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB130857A GB844525A (en) 1957-01-14 1957-01-14 Improvements in or relating to the manufacture of polymeric materials

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB130857A GB844525A (en) 1957-01-14 1957-01-14 Improvements in or relating to the manufacture of polymeric materials

Publications (1)

Publication Number Publication Date
GB844525A true GB844525A (en) 1960-08-10

Family

ID=9719735

Family Applications (1)

Application Number Title Priority Date Filing Date
GB130857A Expired GB844525A (en) 1957-01-14 1957-01-14 Improvements in or relating to the manufacture of polymeric materials

Country Status (1)

Country Link
GB (1) GB844525A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2221479A1 (en) * 1973-03-14 1974-10-11 Bayer Ag

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2221479A1 (en) * 1973-03-14 1974-10-11 Bayer Ag

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