GB794051A - Process for the production of foamed products - Google Patents

Process for the production of foamed products

Info

Publication number
GB794051A
GB794051A GB23848/55A GB2384855A GB794051A GB 794051 A GB794051 A GB 794051A GB 23848/55 A GB23848/55 A GB 23848/55A GB 2384855 A GB2384855 A GB 2384855A GB 794051 A GB794051 A GB 794051A
Authority
GB
United Kingdom
Prior art keywords
acid
acids
acetic
amine
mixture
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
GB23848/55A
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.)
Bayer AG
Original Assignee
Bayer AG
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 Bayer AG filed Critical Bayer AG
Publication of GB794051A publication Critical patent/GB794051A/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
    • C08G18/08Processes
    • 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
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2110/00Foam properties
    • C08G2110/0008Foam properties flexible
    • 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
    • C08G2110/00Foam properties
    • C08G2110/0016Foam properties semi-rigid
    • 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
    • C08G2110/00Foam properties
    • C08G2110/0025Foam properties rigid
    • 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
    • C08G2110/00Foam properties
    • C08G2110/0041Foam properties having specified density
    • C08G2110/005< 50kg/m3
    • 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
    • C08G2110/00Foam properties
    • C08G2110/0041Foam properties having specified density
    • C08G2110/0058≥50 and <150kg/m3
    • 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
    • C08G2110/00Foam properties
    • C08G2110/0083Foam properties prepared using water as the sole blowing agent

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

Carbamates of the formul (C2H5)2NCH2CH2O.CONHC6H5 C18H37NHCOOCH2CH2N(C2H5)2\t and <FORM:0794051/IV (b)/1> respectively are prepared by reacting the corresponding isocyanates and amino-alcohol. The first is converted to salts with (a) acetic, (b) mixed acetic and lauric, (c) mixed acetic and stearic, (d) mixed stearic and benzoic, (e) phenylacetic and (f) mixed acetic and paraffin sulphonic acids, the second is converted to its acetic acid salt, and the third to its salts with (a) mixed oleic and acetic acids, (b) a condensation product of sarcosine and oleic acid, (c) a mixture of acetic acid and the condensation product of lauric acid and methyl glycine. The salts are used as catalysts in the preparation of polyurethanes (see Group IV (a)).ALSO:A process for the production of foamed polyurethane plastics comprises reacting a polyhydroxyl compound, a polyisocyanate and water in the presence of from 1 to 10 per cent by weight, based on the polyhydroxyl compound of one or more salts of an amine with at least one monocarboxylic acid or with a polycarboxylic acid containing more than two carboxylic acid groups or with a sulphonic acid or acid sulphuric acid ester. Neutral, acid or basic salts may be used. Polyesters having terminal carboxyl groups are not included in the term "polycarboxylic acid." The acid and base may be added separately to different components of the reaction mixture. The polyhydroxyl compounds are linear or branched polyesters and polyethers containing hydroxyl groups (which are, if desired, modified by diisocyanates and can also have hetero atoms in the chain), hydrogenated copolymerization products of carbon monoxide and ethylene and mixtures thereof. The salts employed also act as surface-active agents, by suitable choice of the acid or basic component. For the preparation of the salt there are specified secondary aliphatic, araliphatic or aromatic amines, e.g. diethylamine, dibutylamine, diethanolamine, N-monomethylaniline and diphenylamine. Specified tertiary amines are trialkylamines (which can contain hetero atoms such as oxygen or sulphur), amines of the formul R2N-R1-NR2 or R2N(-R1-NR)nR1NR2 in which R represents a methyl or ethyl group, R1 represents an alkylene radical and n is an integer from 1 to 3, tertiary amines containing hydroxyl group (and esters, ethers and isocyanate reaction products thereof), hexahydrodimethylaniline, N-alkylpiperidines, N,N1-dialkylpiperazines, N-alkylpyrrolidines, N-alkyl-carbazoles, N-alkylmorpholines, oleyl amido-diethylamine, the tertiary amine from the reduction and methylation of abietic acid nitrile, the Mannich base from dodecylphenol, formaldehyde and dimethylamine and the reaction product of cogasine sulphochloride and asym. diethylethylene diamine. Acids specified are acetic, ethoxyacetic, phenylacetic, propionic, crotonic, lactic, hydroxycaproic, citric, aconitic, tricarballic, benzoic, hydroxy- and alkoxy-benzoic and cinnamic acids, and monocarboxylic acids obtained by the diene synthesis. As acids with surface-active properties there are specified lauric, undecylenic, palmitic, stearic, oleic, linoleic, linolenic, ricinoleic and hydroxy stearic acids, naphthenic acids from petroleum, acid-sulphuric acid esters of e.g. castor oil. Reaction products of acid chlorides with amino-acids, alkyl - sulphonamido - acetic acids, mono-fatty acid esters of polyvalent alcohols sulphonated on free hydroxy groups, oleic acid esters of oxethane sulphonic acids, sulphuric acid esters of oleic acid ethylanilide, the condensation product of oleic acid and sulphanilic acid, reaction products of fatty acid chlorides with methyltaurine, the acid sulphuric acid esters of fatty acid ethanolamides, alkyl sulphuric acids from natural or synthetic alcohols, acids obtained from natural or synthetic paraffins by sulphochlorination and acid sulphuric acid esters of fatty alcohol oxethylation products are also suitable. In Example (1) portions of an hydroxy-polyester obtained by reacting adipic acid, diethylene glycol and trimethylol propane have added (a) an aqueous solution of the neutral salt of acetic acid and the amine (from the reaction of phenyl isocyanate and N-diethylaminoethanol) of the formula: (C2H5)2N.CH2CH2OCONHC6H5 (b) an aqueous solution of the salt of mixed lauric and acetic acids with the same amine; (c) an aqueous solution of mixed acetic and stearic acid salts of the same amine respectively. A foamed product is obtained on adding mixed tolylene 2,4- and 2,6-diisocyanates. In similar examples there are employed (2) the polyester of (1), a neutral salt of benzoic and stearic acids with the amine of (1), and mixed tolylene-2,4- and 2,6-diisocyanates in various proportions; (3) a basic salt of the tertiary amine of (1) with phenylacetic acid; (4) a neutral cation-active salt of acetic acid with a mixture of the amine used in (1) and an amine of the formula: C18H37NHCOOCH2CH2N (C2H2)2 (5)(a) a mixture of excess mixed oleic and acetic acids with a tertiary amine obtained by reacting tolylene 2,4-diisocyanate with N-diethylaminoethanol; (b) a mixture of the same amine with excess of a mixture of acetic acid and the acid product obtained by condensation of oleic acid chloride with sarcosine; (6) the amine referred to in Example (5) (a), mixed toluylene diisocyanates, a polyester from adipic and phthalic acids and trimethylol propane and a polyester from adipic acid, trimethylol propane and 1,3-butylene glycol; (7) a neutral salt of the amine of Example (1) with a mixture of acetic and paraffin sulphonic acids; (8) the polyester mixture of Example (6), toluylene diisocyanate and a salt of the amine of Example (5) with excess of a mixture of acetic acid and the condensation product of lauric acid and methyglycine; (9) the polyester mixture of Example (6), toluylene diisocyanate and the salt of N-diethylaminoethyl phenyl ether with excess of a mixture of acetic and the condensation product of lauric acid and methyl glycine; (10) a reaction product of an adipic acid/glycol polyester with excess toluylene diisocyanate and the amine salt of Example (9); (11) a polyester from adipic acid, diethylene glycol and trimethylol propane, bis-diethyl ethanolamine adipate, water, toluylene diisocyanate and diethylamine oleate; (12) the polyester of Example (11), bis-diethylethanolamine adipate, water, sulphonated castor oil, oleic acid and toluylene diisocyanate.
GB23848/55A 1954-08-19 1955-08-18 Process for the production of foamed products Expired GB794051A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE343635X 1954-08-19

Publications (1)

Publication Number Publication Date
GB794051A true GB794051A (en) 1958-04-30

Family

ID=6247044

Family Applications (1)

Application Number Title Priority Date Filing Date
GB23848/55A Expired GB794051A (en) 1954-08-19 1955-08-18 Process for the production of foamed products

Country Status (3)

Country Link
CH (1) CH343635A (en)
FR (1) FR1135863A (en)
GB (1) GB794051A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1953637A1 (en) * 1969-10-24 1971-04-29 Bayer Ag Process for the production of foams
US4098731A (en) * 1974-07-03 1978-07-04 Bayer Aktiengesellschaft Process for the production of foams
US4134994A (en) * 1976-12-01 1979-01-16 Air Products And Chemicals, Inc. Amine salts of tertiary amino acids
US4293658A (en) * 1980-05-12 1981-10-06 Abbott Laboratories Process for rigid foams of improved friability
JPS62220510A (en) * 1986-03-08 1987-09-28 バイエル・アクチエンゲゼルシヤフト Novel reactant useful as catalyst for manufacturing isocyanate base plastic
GB2232990A (en) * 1989-05-19 1991-01-02 Bp Chem Int Ltd Process for preparing low density polyurethane foam

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3001955A (en) * 1958-02-26 1961-09-26 Allied Chem Preparation of polyurethane foam using arylenedicarbamic acid ester catalyst
US3036020A (en) * 1958-06-30 1962-05-22 Mobay Chemical Corp Process of making cellular polyurethane using n, n-dialkyl-3-(dialkyl amino) propylamine catalyst
BE617874A (en) * 1962-05-22
DE1154269B (en) * 1962-06-19 1963-09-12 Bayer Ag Process for the production of foams containing urethane groups
GB1543458A (en) * 1976-06-01 1979-04-04 Bayer Ag Process for the production of polyurethanes
DE2915468A1 (en) 1979-04-17 1980-10-30 Basf Ag METHOD FOR PRODUCING URETHANE GROUP CONTAINING POLYISOCYANURATE FOAMS
EP3805285B1 (en) * 2019-10-08 2024-07-10 Evonik Operations GmbH Preparation of polyurethane rigid foam

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1953637A1 (en) * 1969-10-24 1971-04-29 Bayer Ag Process for the production of foams
US3726952A (en) * 1969-10-24 1973-04-10 Bayer Ag Method of molding intergral skin polyurethane foams having mold release properties
US4098731A (en) * 1974-07-03 1978-07-04 Bayer Aktiengesellschaft Process for the production of foams
US4134994A (en) * 1976-12-01 1979-01-16 Air Products And Chemicals, Inc. Amine salts of tertiary amino acids
US4293658A (en) * 1980-05-12 1981-10-06 Abbott Laboratories Process for rigid foams of improved friability
JPS62220510A (en) * 1986-03-08 1987-09-28 バイエル・アクチエンゲゼルシヤフト Novel reactant useful as catalyst for manufacturing isocyanate base plastic
US4857560A (en) * 1986-03-08 1989-08-15 Bayer Aktiengesellschaft Reaction products useful as catalysts in the production of isocyanate-based plastics
JPH0749456B2 (en) * 1986-03-08 1995-05-31 バイエル・アクチエンゲゼルシヤフト Novel reaction products useful as catalysts in the production of isocyanate-based plastics
GB2232990A (en) * 1989-05-19 1991-01-02 Bp Chem Int Ltd Process for preparing low density polyurethane foam

Also Published As

Publication number Publication date
CH343635A (en) 1959-12-31
FR1135863A (en) 1957-05-06

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