WO1999048863A1 - Stabilisation de polyisocyanates organiques - Google Patents

Stabilisation de polyisocyanates organiques Download PDF

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Publication number
WO1999048863A1
WO1999048863A1 PCT/EP1999/001689 EP9901689W WO9948863A1 WO 1999048863 A1 WO1999048863 A1 WO 1999048863A1 EP 9901689 W EP9901689 W EP 9901689W WO 9948863 A1 WO9948863 A1 WO 9948863A1
Authority
WO
WIPO (PCT)
Prior art keywords
polyisocyanates
organic polyisocyanates
tert
butyl
stabilisation
Prior art date
Application number
PCT/EP1999/001689
Other languages
German (de)
English (en)
Inventor
Hansjürgen Rabe
Pramod Gupta
Original Assignee
Bayer Aktiengesellschaft
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 Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to CA002325034A priority Critical patent/CA2325034A1/fr
Priority to JP2000537847A priority patent/JP2002507594A/ja
Priority to AU31451/99A priority patent/AU3145199A/en
Priority to BR9909029-5A priority patent/BR9909029A/pt
Priority to EP99913256A priority patent/EP1082296A1/fr
Priority to KR1020007010539A priority patent/KR20010042135A/ko
Publication of WO1999048863A1 publication Critical patent/WO1999048863A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C263/00—Preparation of derivatives of isocyanic acid
    • C07C263/18—Separation; Purification; Stabilisation; Use of additives

Definitions

  • the present invention relates to the use of 3,5-di-tert-butyl-4-hydroxyphenylpropionic acid esters for the stabilization of polyisocyanates.
  • Organic isocyanates have become very important for the production of polyurethane plastics.
  • the organic polyisocyanates with polyols are used for foam, fiber, film, elastomer and paint production.
  • the organic polyisocyanates tend to discolor when stored, even at low temperatures. This property is particularly pronounced if storage must take place at higher temperatures, e.g. if the solid polyisocyanates are to be converted to urethanes for a homogeneous reaction with reactants such as polyether polyols, polyester polyols or glycols. Also in the prepolymer production, the NCO-OH reaction must be carried out at higher temperatures. It is observed that the isocyanates change color very quickly if no stabilization has been carried out.
  • stabilizers are e.g. sterically hindered phenols, dialkyldiphenylamines, phenothiazines, phosphites or mixtures of representatives from these classes of substances (see, for example, US Pat. No. 3,715,301, US Pat. No. 4,064,157, DT-OS 1,668,275,
  • BHT 2,6-di-tert-butyl-4-methylphenol
  • the present invention relates to the use of 3,5-di-tert-butyl-4-hydroxy-phenylpropionic acid esters as stabilizers for organic polyisocyanates, especially for aromatic polyisocyanates.
  • esters of the phenylpropionic acid mentioned: the methyl, ethyl, propyl and tert-butyl ester, in particular the methyl ester (BHPME).
  • Reactions with polyisocyanates require a balanced reactivity, which is also indicated by traces of other compounds, e.g. Antioxidants, should not be affected.
  • BHPME of e.g. is produced by base-catalyzed addition of acrylic acid methyl ester to 2,6-di-tert-butylphenol and is commercially available, is suitable for all common polyisocyanates, including aliphatic, aromatic and cycloaliphatic polyisocyanates.
  • Examples include: ethylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate, 4,4'-methylene bis (cyclohexyl diisocyanate), m-phenylene diisocyanate, p-phenylene diisocyanate, toluene-2,4-diisocyanate, toluene-2,6 -diisocyanate, 4,4'-methylene-bis- (phenyl isocyanate), 2,3'-methylene-bis- (phenyl isocyanate), 2,3-methylene-bis- (phenyl isocyanate), toluene-
  • phenylpropionic acid esters according to the invention can also be used in combination with known isocyanate stabilizers.
  • the polyurethanes are used for foam, film, paint or elastomer production.
  • Isocyanate stabilizer (FZ) color number (ALPHA) * after 6, 15 and 21 days at 50 ° C
  • the isocyanate was heated 5 times to 60 ° C. and cooled again.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention concerne l'utilisation d'esters d'acides 3,5-Di-tert.-butyl-4-hydroxy-phénylpropioniques pour stabilier des polyisocyanates organiques.
PCT/EP1999/001689 1998-03-25 1999-03-15 Stabilisation de polyisocyanates organiques WO1999048863A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
CA002325034A CA2325034A1 (fr) 1998-03-25 1999-03-15 Stabilisation de polyisocyanates organiques
JP2000537847A JP2002507594A (ja) 1998-03-25 1999-03-15 有機ポリイソシアネート用の安定化剤
AU31451/99A AU3145199A (en) 1998-03-25 1999-03-15 Stabilisation of organic polyisocyanates
BR9909029-5A BR9909029A (pt) 1998-03-25 1999-03-15 Estabilização de poliisocianatos orgânicos
EP99913256A EP1082296A1 (fr) 1998-03-25 1999-03-15 Stabilisation de polyisocyanates organiques
KR1020007010539A KR20010042135A (ko) 1998-03-25 1999-03-15 유기 폴리이소시아네이트의 안정화

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19813136A DE19813136C1 (de) 1998-03-25 1998-03-25 Verwendung von 3,5-Di-tert.-butyl-4-hydroxyphenylpropionsäureestern zur Stabilisierung von organischen Polyisocyanaten
DE19813136.4 1998-03-25

Publications (1)

Publication Number Publication Date
WO1999048863A1 true WO1999048863A1 (fr) 1999-09-30

Family

ID=7862279

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1999/001689 WO1999048863A1 (fr) 1998-03-25 1999-03-15 Stabilisation de polyisocyanates organiques

Country Status (10)

Country Link
EP (1) EP1082296A1 (fr)
JP (1) JP2002507594A (fr)
KR (1) KR20010042135A (fr)
CN (1) CN1294575A (fr)
AU (1) AU3145199A (fr)
BR (1) BR9909029A (fr)
CA (1) CA2325034A1 (fr)
DE (1) DE19813136C1 (fr)
TW (1) TW461898B (fr)
WO (1) WO1999048863A1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BR112019007400A2 (pt) 2016-10-14 2019-07-02 Asahi Chemical Ind composição de isocianato, e, método para a produção de um polímero de isocianato
CN112979917B (zh) * 2016-10-14 2023-04-25 旭化成株式会社 异氰酸酯组合物、异氰酸酯组合物的制造方法以及异氰酸酯聚合物的制造方法
CN108003072B (zh) * 2017-12-04 2020-08-28 万华化学（宁波）有限公司 一种异氰酸酯稳定剂及其制备方法
CN110872238B (zh) * 2018-08-31 2022-07-12 万华化学集团股份有限公司 一种异氰酸酯稳定剂及其制备方法
CN111228245A (zh) * 2020-02-27 2020-06-05 华侨大学 酚类化合物及其在药学上可接受的盐在制备抗乙型肝炎病毒的药物中的应用
TWI754527B (zh) * 2021-01-27 2022-02-01 宏正自動科技股份有限公司 固定端子

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4064157A (en) * 1976-03-29 1977-12-20 The Dow Chemical Company Stabilization of polyisocyanates against discoloration
EP0445608A2 (fr) * 1990-03-07 1991-09-11 Bayer Ag Stabilisation de polyisocyanates organiques
WO1999016821A1 (fr) * 1997-09-30 1999-04-08 Uniroyal Chemical Company, Inc. Polyol de polyether stabilise et mousse de polyurethanne obtenue a partir de ce polyol

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1197437A (en) * 1966-09-23 1970-07-01 Ici Ltd Stabilisation of Isocyanates
US3715301A (en) * 1971-06-30 1973-02-06 Texaco Inc Multi-hydrotorting of coal

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4064157A (en) * 1976-03-29 1977-12-20 The Dow Chemical Company Stabilization of polyisocyanates against discoloration
EP0445608A2 (fr) * 1990-03-07 1991-09-11 Bayer Ag Stabilisation de polyisocyanates organiques
WO1999016821A1 (fr) * 1997-09-30 1999-04-08 Uniroyal Chemical Company, Inc. Polyol de polyether stabilise et mousse de polyurethanne obtenue a partir de ce polyol

Also Published As

Publication number Publication date
AU3145199A (en) 1999-10-18
TW461898B (en) 2001-11-01
BR9909029A (pt) 2000-12-05
JP2002507594A (ja) 2002-03-12
DE19813136C1 (de) 1999-07-15
KR20010042135A (ko) 2001-05-25
CA2325034A1 (fr) 1999-09-30
EP1082296A1 (fr) 2001-03-14
CN1294575A (zh) 2001-05-09

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