EP1171499A1 - Systemes de mousses de polyurethane faciles a demouler - Google Patents

Systemes de mousses de polyurethane faciles a demouler

Info

Publication number
EP1171499A1
EP1171499A1 EP00914085A EP00914085A EP1171499A1 EP 1171499 A1 EP1171499 A1 EP 1171499A1 EP 00914085 A EP00914085 A EP 00914085A EP 00914085 A EP00914085 A EP 00914085A EP 1171499 A1 EP1171499 A1 EP 1171499A1
Authority
EP
European Patent Office
Prior art keywords
molded
fatty acids
polyurethane
polyhydric alcohols
production
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Withdrawn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
EP00914085A
Other languages
German (de)
English (en)
Inventor
Hans-Detlef Arntz
Klaus Brecht
Bernhard John
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 EP1171499A1 publication Critical patent/EP1171499A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/0014—Use of organic additives
    • C08J9/0023—Use of organic additives containing oxygen
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C33/00—Moulds or cores; Details thereof or accessories therefor
    • B29C33/56—Coatings, e.g. enameled or galvanised; Releasing, lubricating or separating agents
    • B29C33/60—Releasing, lubricating or separating agents
    • 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
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/36—Hydroxylated esters of higher fatty acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/10—Esters; Ether-esters
    • C08K5/101—Esters; Ether-esters of monocarboxylic acids
    • C08K5/103—Esters; Ether-esters of monocarboxylic acids with polyalcohols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
    • C08J2375/04—Polyurethanes

Definitions

  • the invention relates to molded polyurethane foams which contain esters of mono- to pentasaturated unsaturated fatty acids and polyhydric alcohols as internal release agents.
  • EP-A 153 639 describes the manufacture of moldings using the RIM technique
  • DE-A 36 31 842 describes ketimines, aldimines, enamines and / or Schiff see bases in the presence of a metal salt of organic acids with 8 to 24 carbon atoms as internal release agents, which preferably prove to be effective in the production of compact and hard integral foams , but significantly slow the polyaddition reaction.
  • DE-A 39 04 810 the manufacture of elastic, essentially compact PUR moldings is used as the inside Release agent a mixture of at least one organic amine, a metal salt of stearic acid and at least one ketimine used in conjunction with at least one organic carboxylic acid.
  • the disadvantage here is the occurrence of shortened flow times, which make it difficult to fill complicated shapes with narrow passages.
  • EP-A 666 880 and DE-A 195 46 097 are alkali or alkaline earth metal salts of alkyl and alkylene succinic acid and their mono- and / or polyamides and imides and their mixtures as internal release agents for the production of cellular to solid PUR moldings known.
  • the object of the invention was therefore to provide a suitable internal release agent for this
  • esters of mono- to pentasaturated unsaturated fatty acids with polyhydric alcohols which are added to the polyol and / or the isocyanate as individual components or as a mixture.
  • the invention thus relates to molded polyurethane foams, which as the inner
  • Release agent ester from mono- to pentasaturated fatty acids and polyvalent Contain alcohols are self-separating, foam-molded, cellular to solid, optionally containing reinforcing polyurea polyurethanes, which are formed by reacting a reaction mixture of: a) an organic polyisocyanate, b) an active hydrogen atom-containing, at least bifunctional compound with a number-average Molecular weight of 300 to 8000, preferably 1000 to 6000, particularly preferably 2000 to 4000, c) a chain extender, d) an internal mold release agent, e) optionally blowing agents, reinforcing agents and auxiliaries, f) optionally catalysts, the starting materials being adhered to Isocyanate index of 70 to 130 are brought to reaction.
  • a reaction mixture of: a) an organic polyisocyanate, b) an active hydrogen atom-containing, at least bifunctional compound with a number-average Molecular weight of 300 to 8000, preferably 1000 to 6000, particularly preferably 2000 to
  • the polyol component b) has a hydroxyl functionality of at least 2.0. It preferably consists of one or more compounds with a hydroxyl functionality of 2.0 or a mixture with an average hydroxyl functionality of 2.02 to 2.95, consisting of: either ba) at least one polyether diol with an OH number of 10 to 115, which by
  • Propylene oxide to ethylene oxide has been produced from 60:40 to 85:15.
  • polyester polyol with an OH number of 28 to 1 12 and an OH functionality of 2 to 3, which consists of adipic, succinic, glutaric, phthalic, isophthalic and / or terphthalic acid by reaction with 1, 4-butanediol, isobutyl glycol, propanediol, methyl propanediol, diethylene glycol, ethylene glycol, hexanediol, nepentyl glycol, glycerol and / or trimethylol propane is obtained;
  • esters, amides or imides which are accessible from mono- to pentasaturated fatty acids by reaction with polyhydric alcohols or amines.
  • Unsaturated carboxylic acids with 8 to 30 carbon atoms such as linoleic, linolenic, palmitoleic, oleic, arachidonic, elaeostearic, clupanodonic or erucic acid are used as fatty acids, which are combined with polyhydric alcohols such as ethanediol, trimethylolpropane, triethanolamine, glycerol, or Pentaerithritol are esterified or amidated with polyvalent amines such as ethylenediamine, diethylene triamine, pentaethylene triamine, polyoxyethylene diamine or triamine.
  • water and / or a physical blowing agent for example R134a, a hydrofluoroalkane mixture
  • a physical blowing agent for example R134a, a hydrofluoroalkane mixture
  • the catalysts known from the literature for example tertiary amines, tin and titanium compounds, can be used as catalysts and, if appropriate, auxiliaries and additives.
  • auxiliaries and additives Depending on the requirement profile, surface-active substances, foam stabilizers, cell regulators, dyes, pigments, hydrolysis protection agents, fungistatic and bacteriostatic substances, oxidizing agents, light stabilizers and antistatic agents can also be added.
  • the polyurethanes are produced in a manner known to the person skilled in the art in principle.
  • the internal release agents according to the invention have a positive effect on the abrasion resistance of the polyurethane material.
  • a reduction in abrasion by 50 to 70% was determined for the polyurethanes according to the invention.
  • molded polyurethane foams according to the invention are particularly suitable for the production of shoe soles, but also for diverse applications in the interior of motor vehicles or in furniture, for example armrests, headrests or
  • polyester diol linear polyadipate, OH number 56
  • Example 2 Glycerol Trilinolate
  • Example 3 Glycerol trioleate
  • Examples 4 and 6 pentaerythritol tetraoleate isocyanate
  • D Dl: 4,4'-methylenediphenyl diisocyanate partially extended with a polyadipate (Al), NCO content approx. 19.5% by weight
  • D2 4,4'-methylenediphenyl diisocyanate partially pre-extended with an EO-PO polyether (OH number 28), NCO content approx. 20.0% by weight
  • the components AI to C were mixed and reacted with the isocyanates Dl and D2 on a conventional two-component mixing and metering system using the low-pressure process and entered into an aluminum mold, the surface of which was not additionally treated or with external ones Release agents was provided. After a reaction time of 2.5 to 4 minutes, the molded part was removed.
  • the physical properties were determined at the earliest 48 hours after the production of the test panels (200 x 200 x 10 mm 3 ), from which the usual test specimens described in the standards (DIN 53504 Sl rod, DIN 53507 tear resistance, abrasion DIN 53516) were produced .
  • the abrasion resistance of the PUR test specimens was tested in accordance with DIN 53516.
  • the measurement of the static slip coefficient ⁇ was determined in accordance with DIN EN 344 using a tractor as the quotient of the force acting horizontally and vertically (lOkN). The results of the measurements are summarized in Tab. 1

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Emergency Medicine (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

L'invention concerne des mousses moulables de polyuréthane qui contiennent, comme agents de séparation intérieurs, des esters d'acides gras insaturés de une fois à cinq fois et des alcools polyvalents.
EP00914085A 1999-03-08 2000-02-24 Systemes de mousses de polyurethane faciles a demouler Withdrawn EP1171499A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE1999110246 DE19910246A1 (de) 1999-03-08 1999-03-08 Trennfreundliche Polyurethan-Formschaum-Systeme
DE19910246 1999-03-08
PCT/EP2000/001499 WO2000053652A1 (fr) 1999-03-08 2000-02-24 Systemes de mousses de polyurethane faciles a demouler

Publications (1)

Publication Number Publication Date
EP1171499A1 true EP1171499A1 (fr) 2002-01-16

Family

ID=7900184

Family Applications (1)

Application Number Title Priority Date Filing Date
EP00914085A Withdrawn EP1171499A1 (fr) 1999-03-08 2000-02-24 Systemes de mousses de polyurethane faciles a demouler

Country Status (7)

Country Link
EP (1) EP1171499A1 (fr)
AU (1) AU3552600A (fr)
DE (1) DE19910246A1 (fr)
PL (1) PL350617A1 (fr)
SK (1) SK12772001A3 (fr)
WO (1) WO2000053652A1 (fr)
ZA (1) ZA200106290B (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6313168B1 (en) * 1999-12-15 2001-11-06 Allergan Sales, Inc. Use of retinoid receptor antagonists in the treatment of cartilage and bone pathologies
US20030114482A1 (en) * 1999-12-15 2003-06-19 Maurizio Pacifici Use of retinoid receptor antagonists or agonists in the treatment of cartilage and bone pathologies
DE102004005223A1 (de) 2004-02-03 2005-08-18 Bayer Materialscience Ag Verbundelemente aus PUR-Werkstoffen mit Oberflächen aus Thermoplast- oder Metallschichten und ein Verfahren zu ihrer Herstellung

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3356621A (en) * 1963-12-26 1967-12-05 Gen Latex And Chemical Corp Rigid polyurethane foams prepared by using as the active hydrogen component a mixture of (a) the transesterification product of pentaerythritol with castor oil and (b) polyester polytols
DE2121670C3 (de) * 1971-05-03 1979-11-15 Bayer Ag, 5090 Leverkusen Verfahren zur Herstellung von Schaumstoffen
GB1575205A (en) * 1976-03-29 1980-09-17 Ici Ltd Process for the production of polyurethane foam mouldings
DE3436163A1 (de) * 1984-10-03 1986-04-10 Bayer Ag, 5090 Leverkusen Verfahren zur herstellung von formkoerpern

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0053652A1 *

Also Published As

Publication number Publication date
DE19910246A1 (de) 2000-09-28
ZA200106290B (en) 2002-07-31
WO2000053652A1 (fr) 2000-09-14
SK12772001A3 (sk) 2002-03-05
PL350617A1 (en) 2003-01-27
AU3552600A (en) 2000-09-28

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