GB802189A - Process for the production of rubber-like polyurethane plastics of high molecular weight - Google Patents

Process for the production of rubber-like polyurethane plastics of high molecular weight

Info

Publication number
GB802189A
GB802189A GB2315356A GB2315356A GB802189A GB 802189 A GB802189 A GB 802189A GB 2315356 A GB2315356 A GB 2315356A GB 2315356 A GB2315356 A GB 2315356A GB 802189 A GB802189 A GB 802189A
Authority
GB
United Kingdom
Prior art keywords
diisocyanate
dimeric
cross
linking agent
condensation
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
GB2315356A
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 GB802189A publication Critical patent/GB802189A/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
    • C08G18/72Polyisocyanates or polyisothiocyanates
    • C08G18/77Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78Nitrogen
    • C08G18/79Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/798Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing urethdione groups

Abstract

A process for the production of rubber-like polyurethanes comprises reacting a linear condensation or polymerization product containing free terminal hydroxyl groups and having a molecular weight above 1000 with a dimeric diisocyanate and a cross-linking agent having a molecular weight below 1000 at a temperature lower than that required to split the dimeric dissocyanate into the corresponding monomeric diisocyanate. The process can be carried out in one embodiment by reacting the linear condensation or polymerization product with an amount of the dimeric diisocyanate sufficient to provide an excess of free NCO groups over the hydroxyl groups in the condensation or polymerization product, and the product obtained is reacted with the cross-linking agent in an amount of 1 to 10 per cent by weight based on the weight of the condensation or polymerization product. In another embodiment the linear condensation or polymerization product is reacted with an amount of the dimeric diisocyanate insufficient to react with all the hydroxyl groups and the product obtained is reacted with the cross-linking agent and with a further amount of the dimeric diisocyanate. Suitable compounds with terminal hydroxyl groups are hydroxypolyesters obtained by esterifying, for example, adipic and phthalic acids with, for example, glycol, diethylene glycol, propylene glycol and butylene glycol-1,3 or -1,4. Also suitable are polymerization products of alkylene oxides and condensation products of glycols with themselves or thiodiglycols. Specified cross-linking agents are diamines, such as o-dichloro-benzidine and 2,5-dichloro-p-phenylene diamine, diand trihydric alcohols such as butanediol-1,3 or -1,4, trimethylol propane, quimtol, tetra- and pentabutylene glycols, hydroxypolyesters and hydroxypolyethers. Suitable dimeric diisocyanates are dimerization products of 2,4-toluylene diisocyanate, chloro-p-phenylene diisocyanate and 1-ethylbenzene-2,4-diisocyanate. In examples: (1) a glycol/adipic acid hydroxypolyester is reacted at 130-140 DEG C. with excess dimeric 2,4-toluylene diisocyanate, butane-1,4-diol is mixed in and the melt poured into moulds. Reaction is completed by heating the mouldings at 100 DEG C.; (2) a similar process is employed, using a mixture of tetra- and pentabutylene glycols as cross-linking agent; (3) in a similar process water is used as the cross-linking agent. Specifications 700,608 and 700,609 are referred to.
GB2315356A 1955-08-01 1956-07-26 Process for the production of rubber-like polyurethane plastics of high molecular weight Expired GB802189A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF18083A DE1014740B (en) 1955-08-01 1955-08-01 Process for the production of high molecular weight crosslinked plastics

Publications (1)

Publication Number Publication Date
GB802189A true GB802189A (en) 1958-10-01

Family

ID=7088819

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2315356A Expired GB802189A (en) 1955-08-01 1956-07-26 Process for the production of rubber-like polyurethane plastics of high molecular weight

Country Status (3)

Country Link
DE (1) DE1014740B (en)
FR (1) FR1155214A (en)
GB (1) GB802189A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3248370A (en) * 1961-10-31 1966-04-26 Bayer Ag Polyurethane process utilizing a diisocyanate mixture
DE1218717B (en) * 1964-02-13 1966-06-08 Bayer Ag Process for the production of high molecular weight crosslinked plastics
US4442280A (en) * 1981-08-12 1984-04-10 Bayer Aktiengesellschaft Heterogeneous systems of polyol/diphenyl methane uret dione diisocyanates and a process for their production
US5814689A (en) * 1997-08-29 1998-09-29 Arco Chemical Technology, L.P. Low viscosity polyuretidione polyurethanes and their use as curatives for solvent and water borne coatings

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2221170A1 (en) * 1972-04-29 1973-11-08 Bayer Ag POLYURETHANE-POLYURETIC FABRICS CONTAINING URETDIONE GROUPS
DE3502683A1 (en) * 1985-01-26 1986-08-07 Hüls AG, 4370 Marl POLYURETHANE WITH URETHANE AND BIURET STRUCTURE
JP3459091B2 (en) * 1993-08-31 2003-10-20 株式会社イノアックコーポレーション One-component composition for polyurethane elastomer and molding method thereof

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE831772C (en) * 1952-11-18 1952-02-18 Bayer Ag Process for the production of high molecular weight crosslinked plastics
DE952940C (en) * 1953-11-30 1956-11-22 Bayer Ag Process for the production of high molecular weight, crosslinked plastics from linear or predominantly linear polyesters, diisocyanates and diamines

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3248370A (en) * 1961-10-31 1966-04-26 Bayer Ag Polyurethane process utilizing a diisocyanate mixture
DE1218717B (en) * 1964-02-13 1966-06-08 Bayer Ag Process for the production of high molecular weight crosslinked plastics
US4442280A (en) * 1981-08-12 1984-04-10 Bayer Aktiengesellschaft Heterogeneous systems of polyol/diphenyl methane uret dione diisocyanates and a process for their production
US5814689A (en) * 1997-08-29 1998-09-29 Arco Chemical Technology, L.P. Low viscosity polyuretidione polyurethanes and their use as curatives for solvent and water borne coatings
US5861193A (en) * 1997-08-29 1999-01-19 Arco Chemical Technology, L.P. Low viscosity polyuretidione polyurethanes and their use as curatives for solvent and water borne coatings

Also Published As

Publication number Publication date
FR1155214A (en) 1958-04-24
DE1014740B (en) 1957-08-29

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