CA2072839A1 - Fusion adhesive - Google Patents

Fusion adhesive

Info

Publication number
CA2072839A1
CA2072839A1 CA002072839A CA2072839A CA2072839A1 CA 2072839 A1 CA2072839 A1 CA 2072839A1 CA 002072839 A CA002072839 A CA 002072839A CA 2072839 A CA2072839 A CA 2072839A CA 2072839 A1 CA2072839 A1 CA 2072839A1
Authority
CA
Canada
Prior art keywords
component
fusion adhesive
procedure
hydroxypolyester
hydroxypolyether
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.)
Abandoned
Application number
CA002072839A
Other languages
French (fr)
Inventor
Harald Werenicz
Franz Maitz
Walter Nussbaumer
Ludwig Stingl
Franz Peter Schmitz
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.)
HB Fuller Licensing and Financing Inc
Original Assignee
Harald Werenicz
Franz Maitz
Walter Nussbaumer
Ludwig Stingl
Franz Peter Schmitz
H.B. Fuller Licensing & Financing, Inc.
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
Priority claimed from DE4121716A external-priority patent/DE4121716C2/en
Application filed by Harald Werenicz, Franz Maitz, Walter Nussbaumer, Ludwig Stingl, Franz Peter Schmitz, H.B. Fuller Licensing & Financing, Inc. filed Critical Harald Werenicz
Publication of CA2072839A1 publication Critical patent/CA2072839A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/12—Layered products comprising a layer of synthetic resin next to a fibrous or filamentary layer
    • A—HUMAN NECESSITIES
    • A41—WEARING APPAREL
    • A41D—OUTERWEAR; PROTECTIVE GARMENTS; ACCESSORIES
    • A41D31/00—Materials specially adapted for outerwear
    • A41D31/02—Layered materials
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/40—Layered products comprising a layer of synthetic resin comprising polyurethanes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B5/00—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts
    • B32B5/02—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by structural features of a fibrous or filamentary layer
    • B32B5/022—Non-woven fabric
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B5/00—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts
    • B32B5/02—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by structural features of a fibrous or filamentary layer
    • B32B5/026—Knitted fabric
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
    • B32B7/04—Interconnection of layers
    • B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
    • 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
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    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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    • C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
    • C—CHEMISTRY; METALLURGY
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    • C08G18/40—High-molecular-weight compounds
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    • C08G18/4018—Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08G18/40—High-molecular-weight compounds
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08G18/4244—Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether groups
    • C08G18/4247—Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether groups derived from polyols containing at least one ether group and polycarboxylic acids
    • C08G18/4252—Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether groups derived from polyols containing at least one ether group and polycarboxylic acids derived from polyols containing polyether groups and polycarboxylic acids
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    • 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
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    • C08G18/48—Polyethers
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    • 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
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    • 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
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C09J175/06—Polyurethanes from polyesters
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06B—TREATING TEXTILE MATERIALS USING LIQUIDS, GASES OR VAPOURS
    • D06B1/00—Applying liquids, gases or vapours onto textile materials to effect treatment, e.g. washing, dyeing, bleaching, sizing or impregnating
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
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    • D06M17/10—Polyurethanes polyurea
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M23/00—Treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, characterised by the process
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06N—WALL, FLOOR, OR LIKE COVERING MATERIALS, e.g. LINOLEUM, OILCLOTH, ARTIFICIAL LEATHER, ROOFING FELT, CONSISTING OF A FIBROUS WEB COATED WITH A LAYER OF MACROMOLECULAR MATERIAL; FLEXIBLE SHEET MATERIAL NOT OTHERWISE PROVIDED FOR
    • D06N3/00—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof
    • D06N3/12—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof with macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. gelatine proteins
    • D06N3/14—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof with macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. gelatine proteins with polyurethanes
    • B—PERFORMING OPERATIONS; TRANSPORTING
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    • B32B2307/724—Permeability to gases, adsorption
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08G2170/20—Compositions for hot melt adhesives
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    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2250/00—Compositions for preparing crystalline polymers
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
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    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
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    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
    • Y10T428/31562—Next to polyamide [nylon, etc.]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
    • Y10T428/31565—Next to polyester [polyethylene terephthalate, etc.]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2221—Coating or impregnation is specified as water proof
    • Y10T442/2246—Nitrogen containing

Abstract

ABSTRACT

The present invention relates to polyurethane fusion adhesives that are hardened by the action of moisture and which contain at least one reaction product from a component that contains NCO
groups and an essentially linear hydroxypolyester, hydroxypolyether, and/or hydroxypolyetherester component. In addition, the present invention relates to a procedure for manufacturing a material that is permeable to water only in vapour form, this being in the form of a fibre material, in particular in the form of a web, which is joined to a polyurethane film, in which the fibre material is coated with a polyurethane material and subsequently the polyurethane material is hardened to form a water-vapour permeable film. The present invention also relates to a material that is permeable to water only in vapour form and which is in the form of a fibre material, in particular in the form of a web, that is bonded to a polyurethane film.

According to the present invention, a fusion adhesive with a segmented hydroxypolyester or an hydroxypolyether or an hydroxypolyetherester component is used for this purpose as polyurethane material. The fusion adhesive according to the present invention can be applied directly or by a transfer technique to the fibre material and is hardened in only one step, by the action of moisture, to form a water vapour permeable, but otherwise high quality water-proof membrane film.

Description

FRO~l: Wordsmith Trans!ation Inc. PHONE NO.: P02 2072~3~

Fu~on Adhe-ivo 5h~ pr---nt inv~ntlo~ relatos to ~usion adhAs~vQ6 eontaining ~t lon3t on- roaot~on product of a co~pon~nt that contain~ NCO
~rou~s, and at lca~t ono ~untially llnoar hy~roxypolyester co~ponent. ~n Additlon, t~- pr~Qnt invcntlon r-lnte~ to n prooq~- f or prGdu~ing a ~atorlal that ~ Y per~eablo only to ~at~r ~n vapour form, ~hi~ ~ntorlal baing, ln ~rticular ln th~ ror~ o~
~ ~eb~ th~ ~lbr~ ~torlal belng bond~ on lt ~ur~ac~ wlt~
polyur~thano ~oll, in whl~h tho ~1br- materlal 1- coated ~th th~
polrurot~n~ ~ator~al, ~ho ~olyur-thano aat-rial sub~-qu-ntly b-ing h~rdon~d to ~or~ a foil thAt ~r watQr-VapoUr pQrme~bla~
Tho pr~ont ~nvention al~o ro1ate~ to a ~aterl~l that ~B
poro-D~l~ only to wat~r ln vapour ~orP and ie ln tha form of a llk~ f~br~ ~tarial th~t 1- bond~d on lt- ~urrac~ to a ~olyurethAn- foil.

2072~33 Materials that permit the passage of water ~n vapour form but not in liquid form have been produced for a considerable time and are extremely important for the manufacture of weather-proof clothing, as well as for tarpaulins, in the construction industry, and for many other applications in which the water-vapour permeability is desirable.

Such materials can be produced on the basis of fibre materials, which can be either knitted or random-laid materials such as fleeces. Such fibre materials are not only water-vapour permeable per se: they are also water permeable. Up to the present, the desired degree of hygro-stability has been achieved mainly in that a foil that is only water-vapour permeable and which is of ~ynthetic material has been joined to the fibre material. The examples of these known materials are, for example, the GORETEX laminates.

U.S. patent 39 53 566 describes a textile material to which a porous water-vapour permeable polytetrafluorethylene film has been laminated by using an adhesive.

From DE-OS 38 36 434, it is known that a web of water-vapour permeable foil can be laminated thermally onto textiles by using a spray-on fusion adhesive. According to DE-OS 38 15 720, in place of this, it is possible to laminate a polyurethane film that is preformed from solution or disper6ion onto textiles thermally (by welding) from a reversal paper.

However, in many respects it is disadvantageous to join pre-manufactured foils to fibre materials. It requires a number of costly proce~sing steps to ~oin foil and fibre materials. The use of an adhesive to ~oin foil and fibre material entails the disadvantaqe that this frequently makes the product stiffer. ln addition, the adhesive that is used can clog and thus block, the film ~tructure that is essential to achieve water-vapour 2072g3~
permeability. Welding a polyurethane film directly onto the fibre material, as described in DE-OS 38 15 720, requires the costly pre-formation of the foil from either solution or dispersion, and, for this reason, it i5 extremely difficult to do from the technical standpoint.

A first step towards overcoming these problems is described in EP-A2-0 2~7 736, according to which a water-vapour permeable and water absorbing coating of a special polyurethane oligomer that has been derivatized with acrylate is produced. This oligomer, together with a pre-formed PTFE matrix film, is rolled onto the fibre material and then hardened in two subsequent hardening 6tages (irradiation hardening and subsequent moisture hardening) and ~oined to the fibre material.

However, this procedure is still very costly and does not constitute a solution to the problems of the prior art. As was formerly the case, a pre-formed PTFE film has to be used: the simultaneous application of liquid polyurethane material and pre-formed teflon-matrix film, as well as the two subsequent hardening ztages, make the procedure very costly.

DE-OS 39 22 028 proposes that material of this type be manufactured in that a layer of adhesive material is applied to a web-like fibre material and joined to the surface of the fibre material by gluing. The adhesive material should be water-vapour permeable but not water-proof, and should, for example, be formed from a fusion adhesive. The application contains no details as to the type of fusion adhesive that is to be used in this process.

A very large number of various types of fusion adhesives are known from the prior art. Usually, these contain a polymer material that essentially determines the cohesion propert~es of the adhesive, in a mixture with resins or the like that render it 2072~39 adhesive and which are essentially decisive for the adhesion properties. Conventional plastifying components are added to this. All three of these principle components can be of the most variecl kinds.

According to the applicant's knowledge, however, it is not possible to form a membrane-like film that is water-vapour permeable and equal to the demands placed on the finished material by a particular application on a fibre layer by using any of the fusion adhesives described in the prior art, let alone those that are commercially available.

For this reason, it is an important task of the present invention to describe fusion adhesives that are suitable for producing a water-vapour per~eable, membrane-like film on a fibre material in situ, 80 that the foil component of the material does not have to be pre-formed, the properties of the finished material with respect to water-vapour permeability, water-proof properties, 6ervice life, stiffness, etc., being approximately equal to the ~aterials known ~rom the prior art.

It is a further task of the present invention to describe a procedure for the inexpensive and problem-free manufacture of water-vapour per~eable materials of this kind and to describe ~aterials that can be manufactured accordingly. The features ~et out $n the independent claims provide a solution to this problem;
advantageous developments are defined in the sub-claims.

The fusion adhesives according to the present invention are, in principle, polyurethane fusion adhe6ives.

DE-OS 38 27 224 discloses similar fusion adhesives for bonding metal, glass, wood, ceramic, leather, plastics, and the like.
2~72~3~

These known fusion adhesiv2s consist either wholly or in part of conversion products of components that contain NCo groups, namely, polyfunctional isocyanates (polyisocyanates) and partially crystalline hydroxypolyesters with contents of exclusively aliphatic dicarboxylic acids, of the general formula _ _ HO ~ (CH2)X - - 11 - (CH2)y 11 (CH2)X - ~H
. Z

wherein x + y e 12 to 26 and, optionally y ~ 8 to 12 or x ~ 6 to 18 and z ~ 3 to 50. The ratio of the reaction of OH:NCO is 1:1.2 to 1:3.0, and preferably 1:1.5 to 1:2.5.

These known fusion adhesives are intended to achieve a particularly short bonding time in that the partially crystalline polyester6 contain decanic diacid, dodecanic diacid, or tetradecanic diacid, with dodecanic diacid being greatly preferred.

It is preferred that the diol component of the polyesters consist of aliphatic C6 - C12 diols, and, in the case of long-chain dicarboxylic acids, of C2 or C~ diols as well. In addition to these diols, etherdiols can also be contained, preferably those based on ethyleneglycol or butanediol-1,4, which however is not preferred. In no case should the proportion of such ether diols be greater than 50 mol-% of the diol component. According to the embodiments, this does not involve segmenting chain components of the polyester, but components of the monomer mixture that regulate the bonding behaviour.

DE-OS 38 27 224 contains no details about the properties of a film-like formed and hardened fusion adhesive according to their teachings, and in particular nothing of their porosity, to say 207~39 nothing of the water-vapour permeability of such n film.
Similarly, DE-OS 38 27 224 contains no indication of the use of the fusion adhesive that they describe to produce water-vapour perme~ble materials that are, however, water-proof.

The fusion adhesives found in the prior art are not suitable as such for the purposes of the present invention.

An important advantage of the present invention is the fact that the fusion adhesive according to the present invention can be applied directly (as well as by a transfer procedure) to a fibre material and processed in situ, in only one hardening stage (namely by the effects of moisture), to form a membrane-like film that i6 water-vapour permeable but which, at the same time, displays a considerable degree of hygro-stability. This makes the manufacture of materials according to the present invention extremely ~imple. For example, the fusion adhesive according to the present invention can be applied by means of a sheet die to a textile or fleece web when in the molten state, or to a transfer medium (and from this, preferably immediately thereafter, onto the fibre material); after this has been done, the desired membrane film is produced by the simple effect of moisture.
Penetration of the fusion adhesive into the fibre material, and the weight per unit area of the foil that is formed (usually approximately 20 g/m2) can be controlled by a 6uitable choice of the processing conditions. This very thin membrane-type film does not detract from the properties of the fibre material even though it is bonded to it very strongly. The thinness of the foil, as well as its very low inherent stiffness, contributes to this. Nevertheless, the foil displays hygro-stability, measured according to DIN 53886, up to test pressures of ~ore than 0.7 bar or 7 m static water column.

Fusion adhesives according to the present invention, in which the component(s) that contain(s) the NCO groups can be caused to 2072~39 react with at least two different component~ that contain OH
groups, namely on the one hand, with an hydroxypolyester and, on the other hand, with an hydroxypolyether, have, according to the applicant's knowledge, no parallel in the prior art. In these reaction products, two NCO functions are each connected either by a polyester chain or by a polyether chain, when the sequence of the polymer components in the molecular chain of the reaction product can be statistical. In one variation, the polyester chain can be segmented by inserted polyether groups.

In the other fusion adhesives according to the present invention in each instance two NCO groups are connected by polyester unit~
which, in their turn, are segmented by inserted polyether groups.
In the extreme case, the polyester groups can be replaced completely by polyether groups, i.e., the fusion adhesive then contains a reaction product of a component that contains NCO
groups with an essentially linear hydroxypolyether component.

The essential modification of this fusion adhesive according to the present invention compared to the prior art according to DE-OS 38 27 224 lies in the segmentation of the diol component by the incorporation of polyether groups. It is particularly preferred that the polyester components be modified to form diol molecules by condensing in polyethyleneglycol with gram molecular weights in the range of a few thousand (in the usual manner by fusion condensation in a vacuum).

The particularly preferred polyester components are derived from copolyesters that are characterized as follows: they are built up from aliphatic and from aromatic dicarboxylic acids and diols having a chain length of C2 to C20. The OH-number of the polyester group lies between 10 and 50, preferably between 10 nnd 40; it~ glass transition temperature i8 between 0 and -50-C.
According to the present invention, these polyesters are modified in that a polyether, preferably polyethyleneglycol with a gram 2072g3~

moleclllar weight of > 1,000, preferably > 3,000, i8 condensed in at a quantity of > 10, and preferably > 20S-mass.

It is preferred that a polyester obtained on the basis of the product Dynacoll ~ 7210 obtainable from Huls AG, which has been modified with 30%-mass PEG 3000 is used.

The copolyester that has been so modified - segmented - can then be caused to react with polyisocyanates, preferably diisocyanates ~uch as, for example, MDI, to form a reactive fusion adhesive.
This isocyanate is, for example, obtainable from Bayer AG under the name ~Desmodur 44 M" R. The reaction is effected at a ratio of OH:NCO = 1.0:1.6 to 1.0:2.6, and preferably 1.0:1.8 to 1.0:2.4.

In order to adjust the mechanical properties of the hardened product, in particular its tensile ~trength as well as its impermeability to water, up to 30 parts (relative to 100 parts of the 6egmented copolyester according to the present invention) of a non-segmented copolyester with a higher glass transition temperature, for example O to 50-C, and preferably To +20 to +40-C can be added during the reaction with the isocyanate. A
preferred example for this is the product Dynacolll 7140 that can be obtained from Hùls AG.

According to the present invention, fusion adhesive6 are manufactured according to the customary process, when the reaction of the hydroxypolyester components according to the present invention and any additional commerc~ally available hydroxypolyester components with the polyisocyanate can be effected simultaneously. In contrast to this, it may be advantageous to react the particular hydroxypolyester separately with the polyisocyanate and then mix the fusion adhesive from the PU components ~o obtained.

2~72~33 Even though the above-described hydroxycopolyesters are Q~pecially preferred according to the present invention, the fusion adhesives according to the present invention can also contain other hydroxypolyesters, hydroxypolyether esters, or hydroxypolyethers, e.g., polycaprolacton, polycarbonates, or polytetrahydrofurane.

It is advantageous that aliphatic polyisocyanates such as, for example, isophorondiisocyanate, tetramethylxylyldiisocyanate, hydrated MDI and hexanediisocyanate can be used instead of diphenylmethane-4,4'-diisocyanate (MDI).

It is preferred that the fusion adhesives according to the present invention contain the derivatized hydroxypolyester component according to the present invention (or hydroxypolyetherester or hydroxypolyether component) as well as a commercially available non-derivatized hydroxypolyester component at a ratio of approximately 2:1. Usual additives of anti-oxidants, fillers (for example, flame retardants), pigments, and the like can also be incorporated. There are no restrictions with regard to the fibre ~aterials that can be combined with the fusion adhesives according to the present invention, neither are there any restrictions with regard to the number of layers or coatings that can be joined to each other and foil that can be formed from fusion adhesive.

Application of the molten fusion adhesive to the fibre material or the transfer medium is preferably effected by using a sheet die, for example, the MA 25 sheet die application valve from Macon Xlebetechnik, Erkrath. This permits absolutely even coating across the whole of the application width at a constant application rate, even with fusion adhesive of varied viscosity, and, simultaneously, minimal application weights. No counter-pressure roller is required during application and this makes the manufacture of the materials according to the present invention 2072~3~

significantly simpler. At the same time, profiled applications are also possible by using different dosing rates across the application width.

The present invention will be described in greater detail below on the basis of the embodiments described. It is understood that these embodiments only illustrate the work that is done according to the present invention and are not to be understood as being restrictive.

~xam~le I

The hydroxycopolyester component of a fusion adhesive according to the present invention was manufactured in that a mixture of 70~-mass ethyleneglycol and 30%-mass polyethyleneglycol with a gram molecular weight of 3,000 was subjected to fusion condensation in a vacuum with adipinic acid, terephthalic acid, and ortho-phthalic acid (in a weight proportion of approximately 2:1:1).

~xample 2 In order to manufacture a fusion adhesive according to the present invention, 280 g (63.3%-wt) of the modified copolyester described in Example 1 was heated to 120-C with 120 g (27.1%-wt) of commercially available amorphous copolyester with T9 c +40-C
(Dynacoll ~ 7140), and then evacuated for 30 minutes at thi6 temperature. The vacuum was below 1 Torr. Subsequently, 42 g (9.5%-wt) diphenylmethane-4,4'-diisocyanate ~Desmodur ~ 44 MS) was added to it. Subsequently, 0.2 g Irganox ~ 1010 (an anti-oxidant) wa~ added.

The mixture was heated for 60 minutes at 120 to 130-C and homogen~zed. The fusion adhesive 60 obtained was then allowed to cool.

2072~3~
ExamPle 2a In order to produce a fusion adhesive according to the present invention, 75 g (37.5%-wt) of Dynacoll 7130, a commercially available copolyester, 25 g (12.5%-wt) of Dynacoll 7210, a commercially available copolyester, and 23 g (11.5~-wt) of Dynacoll 7381, a commercially available copolyester, were heated to 120-C and together with 51 g (25.5%-wt) of a polyethyleneglycol with a molecular weight of 3,000 were evacuated for 45 minutes at this temperature. The vacuum was below 1 Torr. Then, 25 g (12.5%-wt) of diphenylmethane-4,4'-dii60cyanate (Desmodur 44 MS) were added. Subsequently, 1 g (0.5~-wt) of Irganox 1010 (an ~nti-oxidant) was added.

~Xample 3 The fusion adhesive as described in Example 2 was applied at a weight per unit volume of 38 g/m2 to 6ilicon paper using a sheet die application valve MA 25 (Macon Klebetechnik), and then immediately applied to a fleece fibre web, when it was ~ubsequently hardened by the action of moisture.

Ex~mPle 4 The water-vapour permeability as measured by DIN 53333 wa6 determined using a sample of the material described in Example 3, when, in a deviation from the standard, work was carried out with static air.

The water-~apour permeability was determined to be 99 g/m2.d.

Example 5 The water-proof qualities were determined according to DIN 53886 in ~ water pressure test, using a further sample of the matsrial 2072~39 as described in Example 3. To this end, a seam checker ~PFAFF) was used.

According to this standard, the material according to the present invention was water-proof up to a pressure of 0.7 bar (7 m stat~c water column).

The foregoing shows that the present invention permits particularly simple and economical manufacture of water-vapour permeable but otherwise water-proof materials using a 6imple application stage and a 6imilarly 6imple hardening stage, and result6 in ~aterials with out6tanding permeability And water-proof qualities.

Claims (46)

1. Fusion adhesive containing at least one reaction product of a component that contains NCO groups and at least one essentially linear hydroxypolyester component and, optionally, a content of polyethyleneglycol, characterized in that the hydroxypolyester component contains a segmenting hydroxypolyether component that has a mean gram molecular weight of at least 100.
2. Fusion adhesive as defined in claim 1, characterized in that the hydroxypolyether content is 10%-wt or more, preferably 20 to 95%-wt, and in particular approximately 30%-wt, relative to the total diol constituent of the hydroxypolyester component.
3. Fusion adhesive as defined in claim 1 or claim 2, characterized in that the segmenting hydroxypolyether groups have a mean gram molecular weight between 100 and 10,000, preferably between 200 and 6000, and in particular of approximately 3000.
4. Fusion adhesive containing at least one reaction product of at least one component that contains NCO groups with at least one component that contains OH groups, characterised in that the fusion adhesive includes a reaction product of one or a plurality of a component or components that contain NCO groups with at least one hydroxypolyether component or with at least two different components that contain of groups, of which one is a hydroxypolyester and in which the other is a hydroxypolyether.
5. Fusion adhesive as defined in claim 4, characterized in that the hydroxypolyester is segmented by polyether units.
6. Fusion adhesive as defined in claim 5, characterized in that the segmenting polyether units have in each instance a mean gram molecular weight between 100 and 10,000, preferably between 2,000 and 6,000.
7. Fusion adhesive as defined in one of the claims 4 to 6, characterized in that the, optionally other, hydroxypolyether component has a mean gram molecular weight between 100 and 10,000, preferably between 2,000 and 6,000.
8. Fusion adhesive as defined in one of the claims 1 to 7, characterized in that the polyether component or polyether components is or are formed from polyalkyleneglycol, in particular polyethyleneglycol.
9. Fusion adhesive as defined in one of the claims 1 to 8, characterized in that the polyester component has a content of linear aliphatic dicarboxylic acid, preferably a C2 to C14 dicarboxylic acid and in particular of adipinic acid.
10. Fusion adhesive as defined in one of the claims 1 to 9, characterized in that the polyester component includes a copolyester that is built up from aliphatic and aromatic dicarboxylic acids and diols having a chain length of C2 to C20 and preferably an OH number between 10 and 50, in particular between 20 and 40, and a glass transition temperature between 0 and -50°C.
11. Fusion adhesive as defined in one of the claims 1 to 10, characterized in that the polyester component has a content of an aromatic dicarboxylic acid, preferably of terephthalic said and/or phthalic acid or isophthalic acid.
12. Fusion adhesive as defined in claim 11, characterized in that the polyester component contains approximately equal parts by weight of aliphatic and aromatic dicarboxylic acid.
13. Fusion adhesive as defined in claim 12, characterized in that the aromatic dicarboxylic acid constituent of the polyester component consists of approximately equal parts by weight of terephthalic acid and phthalic acid.
14. Fusion adhesive as defined in one of the claims 1 to 13, characterized in that the fusion adhesive contains, in addition, a further, in particular amorphous, hydroxypolyester component which is formed in the manner known per se from isophthalic acid and at least one lower aliphatic diol or polyol, in particular ethyleneglycol, hexanediol, and/or neopentylglycol.
15. Fusion adhesive as defined in one of the claims 1 to 14, characterized in that the component that contains the NCO
groups is a polyisocyanate component, preferably a diisocyanate and in particular at least predominantly diphenylmethane-4,4'-diisocyanate or, however, an aliphatic diisocyanate, in particular isophorondiisocyanate, tetramethylxylyldiisocyanate, hydrated diphenylmethane-4,4'-diisocyanate and/or hexanediisocyanate.
16. Fusion adhesive as defined in at least one of the preceding claims, containing, relative to the total weight, a) between 50 and 70%-wt of the hydroxypolyester component that has approximately 30%-wt relative to the total diol, of a segmenting hydroxypolyether with a mean gram molecular weight of approximately 3,000;
b) a linear hydroxypolyeester that contains no hydroxypolyether: and c) approximately 10%-wt diisocyanate.
17. Fusion adhesive as defined in claim 16, containing, relative to the total weight, a) between 60 and 65%-wt of a polyester that contains a polyethyleneglycol;
b) between 25 and 30%-wt of a polyester that contains no polyethyleneglycol;
c) between 5 and 15%-wt of diphenylmethane-4,4'-diisocyanate;
d) optionally anti-oxidants and other usual additives.
18. Fusion adhesive as defined in one of the preceding claims, containing, relative to the total weight, a) between 20 and 90%-wt of a hydroxypolyether:
b) between 0 and 70%-wt of a linear hydroxypolyester that contains no polyether;
c) between 0 and 70%-wt of a hydroxypolyester that contains polyether;
d) approximately 10%-wt diisocyanate.
19. Fusion adhesive as defined in one of the preceding claims, characterized in that the fusion adhesive can be hardened by the action of moisture, without being irradiated.
20. A procedure for manufacturing a material that is permeable to water only in vapour form, in the form of a fibre material in particular a web-like material that is provided on its surface with a polyurethane film, in which the fibre material is coated with a polyurethane material and subsequently the polyurethane material is hardened to form a water-vapour permeable film, characterized in that the film is formed from a fusion adhesive that is hardened by the effects of moisture, which is applied to the fibre material as a layer, directly or through a transfer process, and which has a content of a reaction product of a component that contains an NCO group with a hydroxypolyester, hydroxypolyetherester, and/or hydroxypolyether component.
21. A procedure as defined in claim 20, characterized in that the hydroxypolyester component of the reaction product contains a segmenting hydroxypolyether component that has a mean gram molecular weight of at least 100.
22. A procedure as defined in claim 21, characterized in that the hydroxypolyether content is 10%-wt or more, preferably 20 to 95%-wt, and in particular approximately 30%-wt, relative to the total diol constituent of the hydroxypolyester component.
23. A procedure as defined in claim 21 or claim 22, characterized in that the segmenting hydroxypolyether groups have a mean gram molecular weight between 100 and 10,000, preferably between 200 and 6,000, and in particular of approximately 3,000.
24. A procedure as defined in claim 20, characterized in that the fusion adhesive includes a reaction product of one or a plurality of components that contain NCO groups or components with at least a hydroxypolyether component or with at least two different components that include OH
groups, of which one is a hydroxypolyester and the other a hydroxypolyether.
25. A procedure as defined in claim 24, characterized in that the hydroxypolyester is segmented by polyether units.
26. A procedure as defined in claim 25, characterized in that the segmenting polyether units have in each instance a mean gram molecular weight between 100 and 10,000, preferably between 2,000 and 6,000.
27. A procedure as defined in one of the claims 24 to 26, characterized in that the optionally other hydroxypolyether component has mean gram molecular weight between 100 and 10,000, preferably between 2,000 and 6,000.
28. A procedure as defined in one of the claims 20 to 27, characterized in that the polyether component or polyether components is/are formed from polyalkyleneglycol, in particular polyethyleneglycol.
29. A procedure as defined in one of the claims 20 to 28, characterized in that the polyester component includes a copolyester that is built up from aliphatic and aromatic dicarboxylic acids and diols with a chain length of C2 to C20, and preferably an OH number between 10 and 50, in particular between 20 and 40, and a glass transition temperature between 0 and -50°C.
30. A procedure as defined in one of the claims 20 to 29, characterized in that the polyester component has a content of a linear aliphatic dicarboxylic acid, preferably a C2 to C14 dicarboxylic acid, and in particular of adipinic acid.
31. A procedure as defined in one of the claims 20 to 30, characterized in that the polyester component has a content of aromatic dicarboxylic acid, preferably of terephthalic acid and/or phthalic or isophthalic acid.
32. A procedure as defined in claim 31, characterized in that the polyester component contains approximately equal parts by weight of aliphatic and aromatic dicarboxylic acid.
33. A procedure as defined in claim 32, characterized in that the aromatic dicarboxylic acid constituent of the polyester component consists of approximately equal parts by weight of terephthalic acid and phthalic acid.
34. A procedure as defined in one of the claims 20 to 33, characterized in that the fusion adhesive also contains an additional, in particular, amorphous, hydroxypolyester component, which is formed in the manner known in and of itself from isophthalic acid and at least one lower aliphatic diol or polyol, in particular ethyleneglycol, hexanediol, and/or neopentylglycol.
35. A procedure as defined in one of the claims 20 to 34, characterized in that the components that contain the NCO
groups is a polyisocyanate component, preferably a diisocyanate, and in particular at least predominantly diphenylmethane-4,4'-diisocyanate or an aliphatic diisocyanate, in particular isophorondiisocyanate, tetramethylxylyldiisocyanate, hydrated diphenylmethane-4,4'-diisocyanate, and/or hexadiisocyanate.
36. A procedure as defined in one of the preceding claims, in which the fusion adhesive, relative to the total weight, contains:
a) between 50 and 70%-wt of the hydroxypolyester component, which, relative to the total diol, has approximately 30%-wt of a segmenting hydroxypolyether with a mean gram molecular weight of approximately 3,000:
b) a linear hydroxypolyester that contains no polyethyleneglycol:
c) approximately 10%-wt diisocyanate.
37. A procedure as defined in claim 36, in which the fusion adhesive, relative to the total weight, contains:

a) between 60 and 65%-wt of the polyester that contains polyethyleneglycol;
b) between 25 and 30%-wt of the polyester that contains no polyethyleneglycol;
c) between 5 and 15%-wt diphenylmethane-4,4'-diisocyanate;
d) optionally anti-oxidants and other usual additives.
38. A procedure as defined in one of the preceding claims, in which the fusion adhesive, relative to the total weight, contains:
a) between 20 and 90%-wt of a hydroxypolyether;
b) between 0 and 70%-wt of a linear hydroxypolyester that contains no polyether;
c) between 0 and 70%-wt of a hydroxypolyester that contains polyether;
d) approximately 10%-wt diisocyanate.
39. A procedure as defined in one of the preceding claims, in which the fusion adhesive is hardened without radiation treatment, by the effects of moisture.
40. A procedure as defined in one of the claims 20 to 39, characterized in that the polyurethane material is applied to the fibre material by a transfer process.
41. Material that permits the passage of water only in vapour form in the form of a fibre material, in particular in the form of a web, that is joined to a polyurethane film, in particular for the manufacture of weather-proof clothing and the like, which can be produced by the procedure as outlined in at least one of the claims 18 to 36.
42. Material as defined in claim 41, characterized in that the polyurethane film is water-proof as measured by DIN 53886 up to and including a test pressure of at least 0.7 bar (7 m water column).
43. Material as defined in claim 41 or 42, characterized in that the fibre material is either knitted or in the form of a fleece.
44. Material as defined in one of the claims 41 to 43, characterized in that the material is built up in two layers, one layer consisting of fibre material and the other of the polyurethane film.
45. Material as defined in one of the claims 41 to 44, characterized in that the material is built up in three or more layers, at least one polyurethane film layer is covered on both sides by layers of fibre material.
46. A film, produced from the fusion adhesive as defined in one of the claims 1 to 19.
CA002072839A 1991-07-01 1992-06-30 Fusion adhesive Abandoned CA2072839A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4121716A DE4121716C2 (en) 1991-07-01 1991-07-01 Hot melt adhesive and its use
DEP4121716.0-43 1991-07-01

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CA2072839A1 true CA2072839A1 (en) 1993-01-02

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CA002072839A Abandoned CA2072839A1 (en) 1991-07-01 1992-06-30 Fusion adhesive

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EP (1) EP0522321B1 (en)
JP (1) JPH05209162A (en)
AT (1) ATE179450T1 (en)
CA (1) CA2072839A1 (en)
DE (2) DE4143454C2 (en)
MX (1) MX9203828A (en)

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US5851661A (en) 1998-12-22
DE59209682D1 (en) 1999-06-02
JPH05209162A (en) 1993-08-20
EP0522321B1 (en) 1999-04-28
US5660887A (en) 1997-08-26
ATE179450T1 (en) 1999-05-15
DE4143454C2 (en) 1995-01-05
US5508371A (en) 1996-04-16
US5883217A (en) 1999-03-16
EP0522321A1 (en) 1993-01-13
MX9203828A (en) 1993-03-01

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