EP0980421B1 - Nettoyant pour adhesifs fusibles en polyurethane a post-reticulation - Google Patents

Nettoyant pour adhesifs fusibles en polyurethane a post-reticulation Download PDF

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Publication number
EP0980421B1
EP0980421B1 EP98922746A EP98922746A EP0980421B1 EP 0980421 B1 EP0980421 B1 EP 0980421B1 EP 98922746 A EP98922746 A EP 98922746A EP 98922746 A EP98922746 A EP 98922746A EP 0980421 B1 EP0980421 B1 EP 0980421B1
Authority
EP
European Patent Office
Prior art keywords
cleaning compositions
compounds
cleaning
reactive
catalysts
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 - Lifetime
Application number
EP98922746A
Other languages
German (de)
English (en)
Other versions
EP0980421A1 (fr
Inventor
Christoph Lohr
Michael Krebs
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.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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 Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP0980421A1 publication Critical patent/EP0980421A1/fr
Application granted granted Critical
Publication of EP0980421B1 publication Critical patent/EP0980421B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/50—Solvents
    • C11D7/5004—Organic solvents
    • C11D7/5022—Organic solvents containing oxygen
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
    • C11D2111/10—Objects to be cleaned
    • C11D2111/14—Hard surfaces
    • C11D2111/20—Industrial or commercial equipment, e.g. reactors, tubes or engines

Definitions

  • the present invention relates to a cleaning agent for removing reactive Polyurethane hotmelts and their reaction products from manufacturing and Processing equipment.
  • Post-crosslinking polyurethane hotmelts have recently found particularly widespread in industrial application because they take advantage of the rapid setting of conventional non-post-curing Hot melt adhesives with the better thermal resistance of reactive Combine adhesives.
  • This moisture-reactive functional groups are usually isocyanate groups, it can, however, also be alkoxysilane groups.
  • the manufacturing and Encapsulated processing devices against the ingress of moisture additionally or alternatively this is covered with dried inert gases to prevent access of moisture.
  • moisture has diffused into the manufacturing and processing systems, so that by the reaction of the reactive hot melt adhesives with this moisture crosslinking, no longer meltable masses arise.
  • at the hotmelt stays in the processing plant for a longer time which often not only lead to a reduction in molecular weight, but (e.g. through the Trimerization of isocyanate groups) also to build up molecular weight, i.e. lead to the formation of non-meltable products.
  • Known cleaning compounds are with the Hot melt adhesive chemically non-reacting masses in the to be cleaned Mix the equipment with the adhesive residue to be removed, only dilute it and displace.
  • cleaning compounds can e.g. non-reactive hot melt adhesives for example based on mixtures of an EVA polymer and one Resin component.
  • EVA polymers are made with common polyurethane hot melt adhesives not miscible.
  • the hot melt adhesive can result to further crosslink its still reactive isocyanate functionality in the mixture React products that are very difficult to remove because they are infusible and are essentially insoluble in the cleaning compound and therefore adhere inaccessible places in the manufacturing or processing equipment.
  • cleaning compounds are based on non-reactive Hotmelts with the addition of monofunctional chain terminators such as alcohols used.
  • cleaning hotmelts are e.g. under the label "Cleaning hotmelt Q 1950" from Henkel has been on the market for a long time.
  • EP-A-0 544 058 proposes cleaning compounds for the removal of reactive polyurethane hot melt adhesives from manufacturing and processing equipment, machines and Plants that are at least one reactive with the isocyanates of the hot melt adhesive convertible monofunctional hydroxy compounds and, if necessary, additional components such as Contains resins, waxes, plasticizers and the like.
  • this object has been achieved by cleaning agents which are non-volatile or non-volatile monohydroxy with a boiling point at normal pressure above 140 ° C and / or secondary Monoamines and depolymerization catalysts selected from the group alkali, alkaline earth or aluminum alcoholates, tertiary Contain amines and catalysts for the construction of polyurethanes.
  • the monohydroxy compound prevents crosslinking of the reactive ones Isocyanate groups and thus the formation of an infusible reaction product.
  • the use of non-volatile monohydroxy compounds allows the use of these Cleaning compounds also in systems that have no explosion protection.
  • the contained in the cleaning compound according to the invention Depolymerization catalyst causes chemical degradation of the already reacted cross-linked or cracked, infusible components of the hot melt, so that also such buildup can be easily and quickly removed from the system.
  • the Cleaning agents according to the invention carry out the chemical degradation by re-urethanization in the case of polyether urethanes and polyisocyanurates.
  • polyether urethanes and polyisocyanurates In the case of hot melt adhesives based on polyester urethanes, there is also an additional one Transesterification of the polyester instead. Due to the large number of ester bonds in the molecule here the chemical degradation is too low molecular compounds and thus low viscous compounds particularly advantageous.
  • the cleaning agent according to the invention contains two essential components, namely a non-volatile or non-volatile monohydroxy compound.
  • non-volatile or non-volatile is understood to mean those monohydroxy compounds which have a boiling point at normal pressure of above 140 ° C., preferably above 160 ° C. and particularly preferably above 200 ° C. As a rule, these monohydroxy compounds continue to have a flash point above 100 ° C. Examples of such monohydroxy compounds are C 6 -C 24 monoalcohols, as are commercially available, for example, under the trade name "Lorol" from Henkel.
  • the saturated fatty alcohol mixture Lorol C12 / C14 is very particularly preferred here.
  • monohydroxy compounds to be used according to the invention are benzyl alcohol, alkylbenzyl alcohols, abietyl alcohol, nonylphenol, polyethylene glycol monoalkyl ether, polypropylene glycol monoalkyl ether and mixtures thereof.
  • Secondary monoamines, optionally in combination with the aforementioned hydroxy compounds, can also be used.
  • all can be used as depolymerization catalysts in the sense of this invention those catalysts that build up from polyurethane chemistry as catalysts the known polymers are used, as well as those known in principle Esterification.
  • catalysts are alcoholates. especially alkali alcoholates such as e.g. Sodium methylate, sodium ethylate. Sodium isopropylate and their alcoholic solutions. In place of sodium alcoholates can of course also the corresponding potassium compounds or alkaline earth or aluminum compounds.
  • the organotin compounds known per se divalent and / or tetravalent tin e.g.
  • Tin (II) carboxylates or dialkyl tin (IV) dicarboxylates such as e.g. Tin (II) octoate or dibutyltin diacetate.
  • Dibutyltin dilaurate (DBTL) or dibutyltin maleate can be used.
  • Farther other organometallic compounds such as e.g. 1,3-dicarbonyl compounds of Iron such as Iron (III) acetylacetonate and especially organometallic Compounds of titanium such as titanium tetraalkylates, especially the easily accessible Titanium tetraisopropylate can be used.
  • they can be used as polyurethane catalysts known tertiary amines can be used for depolymerization.
  • DBTL Dibutyltin dilaurate
  • the detergents according to the invention can also be non-reactive components such as. non-reactive hot melt adhesive components such as thermoplastics, resins, waxes and in particular contain plasticizers.
  • non-reactive hot melt adhesive components such as thermoplastics, resins, waxes and in particular contain plasticizers.
  • plasticizers such as, for example, Mesamoll (trade name of Bayer) or Lipinol T (trade name of Hüls) can be added.
  • cured polyurethane hot-melt strips were produced, in which the in Trade under the name Macroplast QR 2530-21 (polyester urethane) or Macroplast QR 6265-21 (polyether urethane) from Henkel applied in a 3 mm thick layer and air-cured for 4 weeks. Then they became cured polyurethane hot melt layers cut into strips.
  • the saturated fatty alcohol mixture was placed in an Erlenmeyer flask with a magnetic stirrer Lorol C12 / C14 from Henkel. Then 1 wt .-% based on the Alcohol mixture, dibutyltin dilaurate added and the mixture heated to 120 ° C. Thereafter, strips of cured polyurethane hot melt adhesive (10% by weight based on the detergent mixture) entered in the mixture.
  • Example 2 The procedure was as in Example 1, but was used as a depolymerization catalyst Titanium tetraisopropylate used.
  • the cleaning mixtures react according to the prior art, which do not contain a depolymerization catalyst considerably slower. It is particularly disadvantageous that the chemical degradation is not complete takes place and that residues of hardened material remain in the mixture.
  • the depolymerization catalyst contain, the cured residues of polyester and polyether urethanes low temperatures (120 to 140 ° C) through the cleaning mixture completely be resolved.
  • the cross-linked polyurethanes are made up of the liquid components partially dissolved. The result is a mixture with porridge-like, well pumpable and pumpable Consistency.
  • the temperatures used correspond to the usual application temperatures reactive hot melt adhesives so that they can also be Processing plants are readily available.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Claims (5)

  1. Produits de nettoyage pour éliminer les colles à chaud (hot-melt) en polyuréthane réactives et leurs produits de réaction,
    caractérisés en ce que
    ceux-ci renferment des composés monohydroxylés non volatiles ou difficilement volatils ayant un point d'ébullition à pression normale, au dessus de 140 °C et/ou des amines secondaires et des catalyseurs de dépolymérisation choisis dans le groupe des alcoolates de métal alcalin, de métal alcalino-terreux ou d'aluminium, des amines tertiaires ainsi que des catalyseurs pour la décomposition des polyuréthanes.
  2. Produits de nettoyage conformément à la revendication 1,
    caractérisés en ce que
    les composés monohydroxylés non volatils sont choisis dans le groupe des mono-alcools en C6 à C24 de l'alcool benzylique, des alcools alkyl-benzyliques, de l'alcool abiétique, du nonylphénol, des éthers monoalkyliques de polyéthylène glycol, des éthers mono alkyliques de polypropylène glycol, ainsi que des mélanges de ceux-ci.
  3. Produits de nettoyage conformément à l'une des revendications précédentes,
    caractérisés en ce que
    le catalyseur de depolymérisation est choisi parmi les composés organiques de l'étain, de l'étain divalent et/ou tétravalent, les alcoolates de métal alcalin, les tétra alkylates de titane et les amines tertiaires ou leurs mélanges.
  4. Produits de nettoyage conformément à l'une des revendications précédentes,
    caractérisés par
    une teneur supplémentaire en agents plastifiant(s), résines et/ou cires difficilement volatiles, stables à la saponification.
  5. Utilisation des agents de nettoyage conformément à l'une des revendications précédentes pour l'élimination des colles à chaud en polyuréthane réactives, et/ou de leurs produits de réaction durcis complètement, sur des appareils et des installations de production et/ou de façonnage.
EP98922746A 1997-04-29 1998-04-20 Nettoyant pour adhesifs fusibles en polyurethane a post-reticulation Expired - Lifetime EP0980421B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19718065 1997-04-29
DE19718065A DE19718065A1 (de) 1997-04-29 1997-04-29 Reinigungsmittel für nachvernetzende Polyurethan-Hotmelts
PCT/EP1998/002323 WO1998049262A1 (fr) 1997-04-29 1998-04-20 Nettoyant pour adhesifs fusibles en polyurethane a post-reticulation

Publications (2)

Publication Number Publication Date
EP0980421A1 EP0980421A1 (fr) 2000-02-23
EP0980421B1 true EP0980421B1 (fr) 2002-10-30

Family

ID=7828096

Family Applications (1)

Application Number Title Priority Date Filing Date
EP98922746A Expired - Lifetime EP0980421B1 (fr) 1997-04-29 1998-04-20 Nettoyant pour adhesifs fusibles en polyurethane a post-reticulation

Country Status (5)

Country Link
US (2) US6610153B1 (fr)
EP (1) EP0980421B1 (fr)
AU (1) AU7527598A (fr)
DE (2) DE19718065A1 (fr)
WO (1) WO1998049262A1 (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
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DE19718065A1 (de) * 1997-04-29 1998-11-05 Henkel Kgaa Reinigungsmittel für nachvernetzende Polyurethan-Hotmelts
DE20020588U1 (de) * 2000-11-08 2001-05-03 Henkel Dorus Gmbh & Co Kg Reinigungsmittel zur Reinigung von Verarbeitungsaggregaten für reaktive Verbindungen
FR2865211A1 (fr) * 2004-01-21 2005-07-22 Joint Francais Procede de decomposition d'un polymere comportant des groupes urethanne et/ou uree, et solution de depolymerisation pour la mise en oeuvre de ce procede
WO2009143198A2 (fr) * 2008-05-23 2009-11-26 Lubrizol Advanced Materials, Inc. Composites tpu renforcés par des fibres
EP2460860A1 (fr) * 2010-12-02 2012-06-06 Basf Se Utilisation de mélanges pour supprimer des polyuréthanes de surfaces métalliques
KR20130139317A (ko) * 2010-12-02 2013-12-20 바스프 에스이 금속 표면으로부터 폴리우레탄을 제거하기 위한 혼합물의 용도
JP2015000911A (ja) * 2013-06-14 2015-01-05 Dic株式会社 反応性ホットメルト樹脂用剥離剤、剥離方法及び基材
CN114164063B (zh) * 2021-12-16 2023-08-11 万华化学集团股份有限公司 异氰酸酯换热器结垢物的化学清洗剂及制备方法和应用

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Also Published As

Publication number Publication date
DE19718065A1 (de) 1998-11-05
EP0980421A1 (fr) 2000-02-23
WO1998049262A1 (fr) 1998-11-05
US20030211957A1 (en) 2003-11-13
US6610153B1 (en) 2003-08-26
AU7527598A (en) 1998-11-24
DE59806121D1 (de) 2002-12-05

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