EP0039331A1 - Ameliorations aux catalyseurs de polyurethane - Google Patents

Ameliorations aux catalyseurs de polyurethane

Info

Publication number
EP0039331A1
EP0039331A1 EP19800901412 EP80901412A EP0039331A1 EP 0039331 A1 EP0039331 A1 EP 0039331A1 EP 19800901412 EP19800901412 EP 19800901412 EP 80901412 A EP80901412 A EP 80901412A EP 0039331 A1 EP0039331 A1 EP 0039331A1
Authority
EP
European Patent Office
Prior art keywords
catalyst system
polyurethane
represent
alkyl group
different
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.)
Withdrawn
Application number
EP19800901412
Other languages
German (de)
English (en)
Inventor
Bryan Godfrey Willoughby
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.)
National Research Development Corp UK
Original Assignee
National Research Development Corp UK
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 National Research Development Corp UK filed Critical National Research Development Corp UK
Publication of EP0039331A1 publication Critical patent/EP0039331A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/78—Preparation processes
    • C08G63/82—Preparation processes characterised by the catalyst used
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/161—Catalysts containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22
    • C08G18/163—Catalysts containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22 covered by C08G18/18 and C08G18/22
    • C08G18/165—Catalysts containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22 covered by C08G18/18 and C08G18/22 covered by C08G18/18 and C08G18/24

Definitions

  • This invention relates to improved catalysts for the production of polyesters and polyurethanes.
  • Q and Q' which ma be the same or different, each represent a group of the formula or an arylene group
  • R 1 , R 2 , R 3 and R 4 which may be the same or different, each represent a substituted or unsubstituted alkyl group; n represents zero or an integer from 1 to 10, and x represents zero or an integer less than 6.
  • Such compounds are delayed action catalysts for polyester and polyurethane production.
  • delayed action catalyst systems of improved shelf life with greater potential for process control comprise:
  • Q and Q' which may be the same or different, each represent a C 1 to C 10 alkylene, C 2 to C 10 alkenylene or an arylene group;
  • R 1 , R 2 , R 3 and R 4 which may be the same or different , each represent a substituted or unsubstituted alkyl group; and x represents zero or an integer less than 6 ; and (ii ) an amine .
  • Component (ii) of the catalyst system is suitably a tertiary amine, preferably one of the formula: R 5 R 6 R 7 N wherein:
  • R 5 , R 6 , R 7 which may be the same or different, each represent a C 1 to C 5 alkyl group, for example an ethyl group.
  • Triethylamine is found to be a convenient tertiary amine for use as component ( ii) .
  • R 1 , R 2 , R 3 or R 4 suitably represents an unsubstituted alkyl group, for example a C 1 to C 6 alkyl group, preferably a C 1 to C 4 alkyl group.
  • R 1 and R 2 will be identical and it is particularly preferred that they both represent butyl groups.
  • R 3 and R 4 will be identical. It is preferred that R 3 and R 4 both represent a methyl or an ethyl group.
  • Q and Q' are preferably identical, most preferably a C 1 to C 4 linear alkylene group.
  • x represents an integer less than 4, especially 1.
  • Preferred delayed action catalyst systems of the invention are those in which one or, most preferably, both of R 3 and of Q (R 3 and R 4 being identical and Q and Q' being identical) are C 1 to C 4 moieties.
  • R 3 and of Q R 3 and R 4 being identical and Q and Q' being identical
  • examples include the derivatives of ethyl adipate half ester, methyl glutarate half ester and methyl succinate half ester, especially methyl glutarate half ester and methyl succinate half ester.
  • weight ratio (i):(ii) is from 0.80:1 to 1.20:1.
  • compositions of the invention are delayed action catalyst systems for the production of polyurethane.
  • Component (i) of the catalyst systems of the invention may be prepared in accordance with the disclosure of our OLS 2821306. It is particularly preferred that the reagents are anhydrous; for example the organic solvent is preferably sodium-dried.
  • This invention also provides a delayed action process for the preparation of a polyurethane, which process comprises introducing a polyol and a polyisocyanate into a reaction vessel in the presence of a delayed action catalyst system as herein described; forming a homogeneous mixture of the reactants and catalyst system prior to polymerisation; and allowing the homogeneous mixture to polymerise to a polyurethane.
  • a delayed action process for the preparation of a polyurethane, which process comprises introducing a polyol and a polyisocyanate into a reaction vessel in the presence of a delayed action catalyst system as herein described; forming a homogeneous mixture of the reactants and catalyst system prior to polymerisation; and allowing the homogeneous mixture to polymerise to a polyurethane.
  • the initial temperature of the homogeneous mixture is not greater than 30oC, preferably from 20oC to 25oC; if the initial temperature is higher, there is a possibility that the catalyst system will immediately be activated and no delay period observed.
  • excellent results may be attained by using an initial temperature of 40oC to 50oC for the homogeneous mixture.
  • the selection of catalyst component (i) will depend on the desired initial temperature of the homogeneous mixture, the reactant bulk, and, to a lesser extent, reactor geometry and composition. This may readily be determined by routine experiment by one skilled in the art.
  • the catalyst systems of this invention may also be used at higher temperatures at which no delay period is observed.
  • catalyst component (i) Once catalyst component (i) has been selected, it is possible to optimise the system (a) by the amount of (i) present and (b) by the weight ratio (i):(ii) present, thereby giving great control over the process of this invention.
  • both delay time and reaction time are reduced by increasing the quantity of component (i) .
  • the effect of an increased amount of component (i) can be tempered by reducing the weight ratio (i):(ii).
  • This invention provides a polyurethane prepared using a catalyst system of the present invention.
  • stannoxane used as component (i) prepared by reacting equimolar quantities of the half ester with dibutyl tin dioxide in anhydrous toluene, and the viscometry apparatus, were as disclosed in our OLS 2821306.
  • Comparative plot 27 was effected with the conventional catalyst dibutyl tin dilaurate under the conditions shown in Table 2.

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

Des systemes catalyseurs a action retardee, principalement pour la production de polyurethane, ayant une duree de conservation amelioree et un plus grand potentiel de commande du procede comprennent: (i) un compose de formule: (FORMULE) ou: Q et Q', qui peuvent etre identiques ou differents, representent chacun d'eux un alkylene en C1 a C10, un alkenylene en C2 a C10 ou un groupe arylene; R1, R2, R3 et R4, qui peuvent etre identiques ou differents, representent chacun d'eux un groupe alkyle substitue ou non substitue; et x vaut 0 ou un nombre entier inferieur a 6; et (ii) une amine.
EP19800901412 1979-08-07 1980-08-06 Ameliorations aux catalyseurs de polyurethane Withdrawn EP0039331A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB7927505 1979-08-07
GB7927505 1979-08-07

Publications (1)

Publication Number Publication Date
EP0039331A1 true EP0039331A1 (fr) 1981-11-11

Family

ID=10507047

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19800901412 Withdrawn EP0039331A1 (fr) 1979-08-07 1980-08-06 Ameliorations aux catalyseurs de polyurethane

Country Status (3)

Country Link
EP (1) EP0039331A1 (fr)
JP (1) JPS56500966A (fr)
WO (1) WO1981000411A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5177117A (en) * 1989-05-01 1993-01-05 Air Products And Chemicals, Inc. Controlled release catalysts and curing agents for making polyurethane and/or polyisocyanurate product
CA2207146A1 (fr) * 1996-05-28 1997-11-28 Atofina Chemicals, Inc. Catalyseur pour durcissement a faible temperature d'isocyanates bloques
DK1773902T3 (en) 2004-08-04 2018-02-05 Foam Supplies Inc REACTIVITY DIFFERENCE AND CATALYSTS DEGREE IN POLYURETHAN

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL245621A (fr) * 1957-09-25
BE584911A (fr) * 1958-11-24
DE1195049B (de) * 1962-03-23 1965-06-16 Hans J Zimmer Verfahrenstechni Verfahren zur Herstellung von Poly-(aethylenglykolterephthalat)
GB1533308A (en) * 1975-12-22 1978-11-22 M & T Chemicals Inc High resiliency polyurethane foam with breathability and reduced shrinkage by use of certain tin catalysts
GB1604224A (en) * 1977-05-16 1981-12-02 Rubber & Plastic Res Ass Polyurethane catalysts

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO8100411A1 *

Also Published As

Publication number Publication date
WO1981000411A1 (fr) 1981-02-19
JPS56500966A (fr) 1981-07-16

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Legal Events

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PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

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17P Request for examination filed

Effective date: 19810821

AK Designated contracting states

Designated state(s): DE FR GB

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 19831118

RIN1 Information on inventor provided before grant (corrected)

Inventor name: WILLOUGHBY, BRYAN GODFREY