WO1981000411A1 - Ameliorations aux catalyseurs de polyurethane - Google Patents

Ameliorations aux catalyseurs de polyurethane Download PDF

Info

Publication number
WO1981000411A1
WO1981000411A1 PCT/GB1980/000124 GB8000124W WO8100411A1 WO 1981000411 A1 WO1981000411 A1 WO 1981000411A1 GB 8000124 W GB8000124 W GB 8000124W WO 8100411 A1 WO8100411 A1 WO 8100411A1
Authority
WO
WIPO (PCT)
Prior art keywords
catalyst system
represent
polyurethane
alkyl group
different
Prior art date
Application number
PCT/GB1980/000124
Other languages
English (en)
Inventor
B Willoughby
Original Assignee
Nat Res Dev
B Willoughby
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 Nat Res Dev, B Willoughby filed Critical Nat Res Dev
Publication of WO1981000411A1 publication Critical patent/WO1981000411A1/fr

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.
PCT/GB1980/000124 1979-08-07 1980-08-06 Ameliorations aux catalyseurs de polyurethane WO1981000411A1 (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
WO1981000411A1 true WO1981000411A1 (fr) 1981-02-19

Family

ID=10507047

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1980/000124 WO1981000411A1 (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)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU619975B2 (en) * 1989-05-01 1992-02-06 Air Products And Chemicals Inc. Controlled release catalysts and curing agents for making polyurethane and/or polyisocyanurate product
EP0810245A1 (fr) * 1996-05-28 1997-12-03 Elf Atochem North America, Inc. Catalyseur pour le durcissement à basse température d'un isocyanate bloqué
US10385177B2 (en) 2004-08-04 2019-08-20 Foam Supplies, Inc. Reactivity drift and catalyst degradation in polyurethane foam

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1242464A (fr) * 1957-09-25 1960-09-30 Union Carbide Corp Procédé pour accélérer la réaction d'un isocyanate ou d'un isothiocyanate avec un composé à hydrogène actif
FR1245085A (fr) * 1958-11-24 1960-11-04 Union Carbide Corp Mousses de polyuréthane et leur procédé de fabrication
DE1195049B (de) * 1962-03-23 1965-06-16 Hans J Zimmer Verfahrenstechni Verfahren zur Herstellung von Poly-(aethylenglykolterephthalat)
FR2336428A1 (fr) * 1975-12-22 1977-07-22 M & T Chemicals Inc Mousse hautement elastique possedant des proprietes ameliorees d'aeration et de retrait reduit du fait de l'utilisation de certains catalyseurs a base d'etain et son procede de preparation
DE2821306A1 (de) * 1977-05-16 1978-12-21 Nat Res Dev Organozinnoxy-diester und verfahren zu deren herstellung

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1242464A (fr) * 1957-09-25 1960-09-30 Union Carbide Corp Procédé pour accélérer la réaction d'un isocyanate ou d'un isothiocyanate avec un composé à hydrogène actif
FR1245085A (fr) * 1958-11-24 1960-11-04 Union Carbide Corp Mousses de polyuréthane et leur procédé de fabrication
DE1195049B (de) * 1962-03-23 1965-06-16 Hans J Zimmer Verfahrenstechni Verfahren zur Herstellung von Poly-(aethylenglykolterephthalat)
FR2336428A1 (fr) * 1975-12-22 1977-07-22 M & T Chemicals Inc Mousse hautement elastique possedant des proprietes ameliorees d'aeration et de retrait reduit du fait de l'utilisation de certains catalyseurs a base d'etain et son procede de preparation
DE2821306A1 (de) * 1977-05-16 1978-12-21 Nat Res Dev Organozinnoxy-diester und verfahren zu deren herstellung

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU619975B2 (en) * 1989-05-01 1992-02-06 Air Products And Chemicals Inc. Controlled release catalysts and curing agents for making polyurethane and/or polyisocyanurate product
EP0810245A1 (fr) * 1996-05-28 1997-12-03 Elf Atochem North America, Inc. Catalyseur pour le durcissement à basse température d'un isocyanate bloqué
CN1105157C (zh) * 1996-05-28 2003-04-09 北美埃尔夫爱托化学股份有限公司 用于封端异氰酸酯类低温固化的催化剂
US10385177B2 (en) 2004-08-04 2019-08-20 Foam Supplies, Inc. Reactivity drift and catalyst degradation in polyurethane foam

Also Published As

Publication number Publication date
JPS56500966A (fr) 1981-07-16
EP0039331A1 (fr) 1981-11-11

Similar Documents

Publication Publication Date Title
DE2616416C2 (de) 1,3,5-Tris-(N,N-dialkylaminoalkyl)-s- hexahydrotriazin-Anlagerungsverbindungen und ihre Verwendung als Trimerisierungskatalysatoren für Polyisocyanate
KR910014423A (ko) 폴리이소시아네이트혼합물, 이의 제조방법 및 피복 조성물용 결합제로서 또는 이소시아네이트 그룹 또는 카복실 그룹에 대해 반응성인 화합물용 반응물로서의 이의 용도
ES2000397A6 (es) Un procedimiento para producir un tejido forrado de poliuretano
ES8500294A1 (es) Procedimiento para preparar un oligomero de un diisocianato
US4264745A (en) Fire-retardant polyurethane foam based on a bromine-containing polyester
KR940014497A (ko) 열가소성 생분해성 수지 및 그 제조방법
KR880001739A (ko) 열가소성 성형 조성물
EP0169707A2 (fr) Procédé pour la production de polymères contenant des liaisons isocyanurate et/ou oxazolidone
GB1453840A (en) Moulding composition
EP0113172A1 (fr) Amino-polyols aromatiques et mousses rigides de polyuréthane et de polyisocyanurate obtenues à partir de ces polyols
US4670068A (en) Polyfunctional isocyanate crosslinking agents for propellant binders
US3061557A (en) Method of reacting an active hydrogen containing compound with an isocyanate or isothiocyanate in contact with a polystannate catalyst
EP0277023A2 (fr) Procédé pour la préparation d'un catalyseur d'hydrosilylation
US3133113A (en) Method for preparing polycarbonate esters
IE41255B1 (en) A process for the production of cross-linked plastics
US3231597A (en) Polyurethane preparation
WO1983000328A1 (fr) Agents solides bloques de reticulation a base de 1,4-cyclohexane bis(methylisocyanate)
WO1981000411A1 (fr) Ameliorations aux catalyseurs de polyurethane
RU2003105466A (ru) Композиции дифенилметандиизоцианата
US4962213A (en) Energetic azido curing agents
US4758606A (en) Polyester polyols prepared by reacting a polyhydric alkoxylated derivative with a polycarboxylic acid
US3139449A (en) Process for preparing organic isothiocyanate using phosphorus-containing catalysts
EP0113507B2 (fr) Procédé de préparation de polyols aromatiques et mousses rigides de polyuréthane et de polyisocyanurate obtenues à partir de ces polyols
US4950722A (en) Unsaturated epoxy moiety, unsaturated monomer and liquid epoxy compound solution
ES489210A1 (es) Procedimiento para la obtencion de lacas de un solo compo- nente

Legal Events

Date Code Title Description
AK Designated states

Designated state(s): JP US

AL Designated countries for regional patents

Designated state(s): DE FR GB

WWE Wipo information: entry into national phase

Ref document number: 1980901412

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 1980901412

Country of ref document: EP

WWW Wipo information: withdrawn in national office

Ref document number: 1980901412

Country of ref document: EP