CA2258585A1 - Reactive melt adhesive composition for double glazing - Google Patents
Reactive melt adhesive composition for double glazing Download PDFInfo
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- CA2258585A1 CA2258585A1 CA002258585A CA2258585A CA2258585A1 CA 2258585 A1 CA2258585 A1 CA 2258585A1 CA 002258585 A CA002258585 A CA 002258585A CA 2258585 A CA2258585 A CA 2258585A CA 2258585 A1 CA2258585 A1 CA 2258585A1
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- glass
- layers
- silane
- reactive binder
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- 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
- C09J115/00—Adhesives based on rubber derivatives
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- 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
- C09J119/00—Adhesives based on rubbers, not provided for in groups C09J107/00 - C09J117/00
- C09J119/006—Rubber characterised by functional groups, e.g. telechelic diene polymers
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- 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
- C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
- C09J123/26—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers modified by chemical after-treatment
-
- 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
- C09J143/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing boron, silicon, phosphorus, selenium, tellurium, or a metal; Adhesives based on derivatives of such polymers
- C09J143/04—Homopolymers or copolymers of monomers containing silicon
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
- C08L2666/04—Macromolecular compounds according to groups C08L7/00 - C08L49/00, or C08L55/00 - C08L57/00; Derivatives thereof
Abstract
Melt adhesive compositions containing a mixture of at least one reactive binder based on silane-functional polyisobutylene, hydrated polybutadiene and/or poly-.alpha.-olefines and a non-reactive binder from the group of butyl rubbers, poly-.alpha.-olefines and a non-reactive binder from the group of butyl rubbers, poly-.alpha.-olefines, polybutenes, styrene block copolymers or diene polymers may be used as one or two-part adhesives/sealants for the production of double glazing. Here, no separate spacer of metal or plastic sections are needed. As the entire edge bond consists of a uniform material, on the one hand the production process for the double-glazing units can be greatly simplifed and on the other the uniform material can be subjected particularly easily to a recycling process after a double-glazing unit has been dismantled, as it not a composite material.
Description
CA 022~8~8~ 1998-12-17 '''~i''' A Reactive Hotmelt Adhesive Composition for Insulating Glass This invention relates to hotmelt adhesive compositions and to their use, more particularly for the manufacture of double glazing or multiple glazing.
Insulating glass is now widely used in the building industry and, to a 5 large extent, in vehicle manufacture by virtue of its many advantages, including in particular imp~oved thermal and acoustic insulation in relation to single glazing. It is known that multiple glazing systems consist of two or more layers of glass arranged parallel to one another and joined at their edges in such a way that the space between the layers is sealed off from the 10 ambient air so that no moisture is able to penetrate into that space. In addition, the edge bond/seal is designed to withstand all the various mechanical and chemical stresses which arise out of varying climatic condi~iol1s. In many cases, the space in question is even filled with dry gases which increase thermal insulation and acoustic insulation in relation to air 1 5 fillings.
In co""nercially available multiple glazing units, rigid spacers keep the layers of glass at the required distance apart from one another. In the most common embodiment, the spacer consists of an aluminium or steel hollow section. It is arranged near the edges of the glass layers in such a way that, 20 together with the edges of the glass layer, the spacer forms an outwardly facing channel for accommodating sealants and adhesives. Normally, that side of the spacer which faces the space between the layers of glass has small openings and the hollow interior of the spacer is used to accommodate a drying agent to adsorb moisture and any solvent residues present in the air 25 or gas space between the layers of glass. This prevents moisture from condensing on the inside of the glass layers at low ambient temperatures. In high-quality multiple glazing systems, a sealant with a good barrier effect CA 022~8~8~ 1998-12-17 ' . , against water vapor is provided between those surfaces of the spacer which face the glass layers and the glass surface. Formulations based on polyisobutylene and/or butyl rubber are generally used as the sealant. The ~1annel formed by the outwardly directed face of the spacer and the margins 5 of the glass layers is generally filled with a two-component adhesive/ sealantwhich bonds/seals the multiple glazing unit with sufficient strength. The adhesive/sealant used must show good adhesion to the glass and, in addition, must be sufficiently elastic to withstand the expansion and conl~ion move",enls of the glass layers under varying climatic conditions.
Accordingly, the manufacture of high-quality multiple glazing units of the type in question naturally involves a number of complex process steps and is extremely expensive despite a high degree of automation on large assembly lines. As a result, there has been no shortage of attempts in the past to simplify the complex process steps involved in the production of multiple glazing and, in particular, to eliminate the need for pre-profiled spacers.
The so-called USystem Biver" consists, for example, of a thermoplastic inner strand of which the polymer component is preferably composed of polyisobutylene or butyl rubber and which contains a molecular sieve for adsorbing moisture. This strand faces the space between the glass layers and is initially extruded onto one layer of glass, after which the second layer of glass is positioned over the first and the two glass layers are then pressed together until they are at the required distance apart. Thereafter the outer margin is sealed by a generally two-component adhesive/sealant. In this arrangement, the inner strand of the thermoplastic polymer performs the function of the spacer and carries the drying agent and, in addition, acts as the main barrier against water vapor. The outer generally two-component adhesive/sealant provides for the mechanical strength of the double glazing system. This system is described in numerous patents/applications, cf. for example DE-C-25 55 381, DE-A-25 55 383, DE-A-25 55 384 and EP-A-176 CA 022~8~8~ 1998-12-17 388.
DE-A-44 07 892 describes a process for the production of double or multiple glazing systems in which the two or more layers of glass arranged parallel to one another are kept at a distance and, at their margins, are 5 surrounded by an extrusion-coated frame which holds the layers of glass apart from one another. According to the document in question, the material used for extrusion coating is a thermoset, thermoplastic or ceramic material.
The composition of the injection molding material is not disu ~ssed, nor are any details provided as to ~vhether and how the gas or the air in the space(s) 10 between the glass layers can be kept dry.
EP-A- 517 067 describes a deformable strip-like extrudate for sealing and maintaining the distance between two layers of insulating glass. The deformable strip consists of a flow-resistant polymer matrix which, at its center, contains a flat wave-shaped material which extends perpendicularly 15 of the layers of glass and which is in i"li"~ale contact with the polymer matrix.
This flat wave-shaped m~le, ial performs the function of the spacer and, at the same time, acts as a water vapor barrier. The volume of the polymer matrix which faces the space between the layers of glass preferably contains a drying agent. A semi-interpenetrating network consisting of a butyl rubber 20 and a lightly crosslinked polyisobutylene is proposed as the polymer matrix.
The prefor",ed deformable sealing strip is produced by co-extrusion of the polymer matrices and the flat wave-shaped material. This preformed sealing tape is then placed on one of the layers of glass, the second glass layer is positioned over the first and the two layers of glass are then pressed 25 together. Since no further curing process takes place after application, the marginal zone between the sealing strip and the glass layer has a tendency towards cold flow.
DE-A-38 34 400 describes a double glazing unit which consists of two layers of glasss joined at their edges by a plastic spacer. The spacer 30 consists of two or more different layers of which the inner layer defines the , .. . .. .
CA 022~8~8~ 1998-12-17 : .
Insulating glass is now widely used in the building industry and, to a 5 large extent, in vehicle manufacture by virtue of its many advantages, including in particular imp~oved thermal and acoustic insulation in relation to single glazing. It is known that multiple glazing systems consist of two or more layers of glass arranged parallel to one another and joined at their edges in such a way that the space between the layers is sealed off from the 10 ambient air so that no moisture is able to penetrate into that space. In addition, the edge bond/seal is designed to withstand all the various mechanical and chemical stresses which arise out of varying climatic condi~iol1s. In many cases, the space in question is even filled with dry gases which increase thermal insulation and acoustic insulation in relation to air 1 5 fillings.
In co""nercially available multiple glazing units, rigid spacers keep the layers of glass at the required distance apart from one another. In the most common embodiment, the spacer consists of an aluminium or steel hollow section. It is arranged near the edges of the glass layers in such a way that, 20 together with the edges of the glass layer, the spacer forms an outwardly facing channel for accommodating sealants and adhesives. Normally, that side of the spacer which faces the space between the layers of glass has small openings and the hollow interior of the spacer is used to accommodate a drying agent to adsorb moisture and any solvent residues present in the air 25 or gas space between the layers of glass. This prevents moisture from condensing on the inside of the glass layers at low ambient temperatures. In high-quality multiple glazing systems, a sealant with a good barrier effect CA 022~8~8~ 1998-12-17 ' . , against water vapor is provided between those surfaces of the spacer which face the glass layers and the glass surface. Formulations based on polyisobutylene and/or butyl rubber are generally used as the sealant. The ~1annel formed by the outwardly directed face of the spacer and the margins 5 of the glass layers is generally filled with a two-component adhesive/ sealantwhich bonds/seals the multiple glazing unit with sufficient strength. The adhesive/sealant used must show good adhesion to the glass and, in addition, must be sufficiently elastic to withstand the expansion and conl~ion move",enls of the glass layers under varying climatic conditions.
Accordingly, the manufacture of high-quality multiple glazing units of the type in question naturally involves a number of complex process steps and is extremely expensive despite a high degree of automation on large assembly lines. As a result, there has been no shortage of attempts in the past to simplify the complex process steps involved in the production of multiple glazing and, in particular, to eliminate the need for pre-profiled spacers.
The so-called USystem Biver" consists, for example, of a thermoplastic inner strand of which the polymer component is preferably composed of polyisobutylene or butyl rubber and which contains a molecular sieve for adsorbing moisture. This strand faces the space between the glass layers and is initially extruded onto one layer of glass, after which the second layer of glass is positioned over the first and the two glass layers are then pressed together until they are at the required distance apart. Thereafter the outer margin is sealed by a generally two-component adhesive/sealant. In this arrangement, the inner strand of the thermoplastic polymer performs the function of the spacer and carries the drying agent and, in addition, acts as the main barrier against water vapor. The outer generally two-component adhesive/sealant provides for the mechanical strength of the double glazing system. This system is described in numerous patents/applications, cf. for example DE-C-25 55 381, DE-A-25 55 383, DE-A-25 55 384 and EP-A-176 CA 022~8~8~ 1998-12-17 388.
DE-A-44 07 892 describes a process for the production of double or multiple glazing systems in which the two or more layers of glass arranged parallel to one another are kept at a distance and, at their margins, are 5 surrounded by an extrusion-coated frame which holds the layers of glass apart from one another. According to the document in question, the material used for extrusion coating is a thermoset, thermoplastic or ceramic material.
The composition of the injection molding material is not disu ~ssed, nor are any details provided as to ~vhether and how the gas or the air in the space(s) 10 between the glass layers can be kept dry.
EP-A- 517 067 describes a deformable strip-like extrudate for sealing and maintaining the distance between two layers of insulating glass. The deformable strip consists of a flow-resistant polymer matrix which, at its center, contains a flat wave-shaped material which extends perpendicularly 15 of the layers of glass and which is in i"li"~ale contact with the polymer matrix.
This flat wave-shaped m~le, ial performs the function of the spacer and, at the same time, acts as a water vapor barrier. The volume of the polymer matrix which faces the space between the layers of glass preferably contains a drying agent. A semi-interpenetrating network consisting of a butyl rubber 20 and a lightly crosslinked polyisobutylene is proposed as the polymer matrix.
The prefor",ed deformable sealing strip is produced by co-extrusion of the polymer matrices and the flat wave-shaped material. This preformed sealing tape is then placed on one of the layers of glass, the second glass layer is positioned over the first and the two layers of glass are then pressed 25 together. Since no further curing process takes place after application, the marginal zone between the sealing strip and the glass layer has a tendency towards cold flow.
DE-A-38 34 400 describes a double glazing unit which consists of two layers of glasss joined at their edges by a plastic spacer. The spacer 30 consists of two or more different layers of which the inner layer defines the , .. . .. .
CA 022~8~8~ 1998-12-17 : .
interior space and consists of a cured adhesive which conl&ins a moisture-absorbing sub~lance while the outer layer consisls of a cured adhesive which is di~ere, lt from the adhesive forming the inner layer. The inner layer of the adhesive consists of polymers with a relatively high permeability to water 5 vapor and may additionally contain a powder-form drying agent, for example a molecular sieve, while the outer adhesive layer is said to have a lower specific permeability to water vapor than the inner layer. Polyurethanes or silicone rubbers are proposed for the inner layer while a polysulfide-based adhesive is proposed foF the outer layer. This system has the advantage 10 over the above-mentioned double glazing systems that both layers of adhesive consist of reactive materials which crosslink after application so thatthe mechanical cohesion of the layers of glass is better, even under weathering influences. The disadvantage of this process is that two different materials have to be applied in two process steps.
WO 95/13449 describes sealing profiles preformed for this purpose.
The sealing profiles consist of a completely or partly crosslinked polyiso-butylene copolymer as the polymer matrix and contain an aluminium foil as a water vapor diffusion barrier. The disadvantage of this system is that the spacer system is made up of several different layers which complicates the 20 production process and which is also unfavorable from the point of view of disposal and/or recycling.
EP-A-232 873 describes sealants for the production of spacer-free double glazing systems based on 20 to 80% by weight of epoxidized natural rubber, 5 to 30% by weight of at least one other epoxy compound and an 25 amine or mercaptan containing trialkoxysilyl groups as crosslinking agent andtypical additives, such as coupling agents, tackifiers, plasticizers, fillers, drying agents, antiagers and UV filters. Although double glazing systems such as these show excellent resistance to ageing, their main disadvantage is that they can only be produced as two-component systems where the two 30 reactive components can only be mixed immediately before application.
.... . .
- CA 022~8~8~ 1998-12-17 It has now been found that multiple glazing systems can be produced particularly inex~ensively by using hotmelt adhesive compositions which contain a mixture of at least one reactive binder and at least one non-reactive binder, at least one reactive binder consisting of silane-functional 5 polyisobutylene and/or silane-functional hydrogenated polybutadiene and/or silane-fi nc~ional poly-a-olefin and the non-reactive binder(s) being selected from the group consisting of butyl rubbers, poly-a-olefins, polybutenes, rubbers based on styrene block copolymers, rubbers based on statistical diene hol"opolymers and/or copolymers.
The p, efe" ecJ silane-functional groups of the reactive binder(s) can be represented by formula (1):
R2 R' ¦ 2-b 3-a -A--Si--O--''i X, (1) Xb -n where -A- can represent -(CH2)m - (2) -S~(CH2)m ~
H O H
and R' and R2 may be the same or different and represent an alkyl group containing 1 to 20 carbon atoms, an aryl group containing 6 to 20 carbon 35 atoms or an arylalkyl group containing 7 to 20 carbon atoms, X can be a ~ .
CA 022~8~8~ 1998-12-17 ,':
WO 95/13449 describes sealing profiles preformed for this purpose.
The sealing profiles consist of a completely or partly crosslinked polyiso-butylene copolymer as the polymer matrix and contain an aluminium foil as a water vapor diffusion barrier. The disadvantage of this system is that the spacer system is made up of several different layers which complicates the 20 production process and which is also unfavorable from the point of view of disposal and/or recycling.
EP-A-232 873 describes sealants for the production of spacer-free double glazing systems based on 20 to 80% by weight of epoxidized natural rubber, 5 to 30% by weight of at least one other epoxy compound and an 25 amine or mercaptan containing trialkoxysilyl groups as crosslinking agent andtypical additives, such as coupling agents, tackifiers, plasticizers, fillers, drying agents, antiagers and UV filters. Although double glazing systems such as these show excellent resistance to ageing, their main disadvantage is that they can only be produced as two-component systems where the two 30 reactive components can only be mixed immediately before application.
.... . .
- CA 022~8~8~ 1998-12-17 It has now been found that multiple glazing systems can be produced particularly inex~ensively by using hotmelt adhesive compositions which contain a mixture of at least one reactive binder and at least one non-reactive binder, at least one reactive binder consisting of silane-functional 5 polyisobutylene and/or silane-functional hydrogenated polybutadiene and/or silane-fi nc~ional poly-a-olefin and the non-reactive binder(s) being selected from the group consisting of butyl rubbers, poly-a-olefins, polybutenes, rubbers based on styrene block copolymers, rubbers based on statistical diene hol"opolymers and/or copolymers.
The p, efe" ecJ silane-functional groups of the reactive binder(s) can be represented by formula (1):
R2 R' ¦ 2-b 3-a -A--Si--O--''i X, (1) Xb -n where -A- can represent -(CH2)m - (2) -S~(CH2)m ~
H O H
and R' and R2 may be the same or different and represent an alkyl group containing 1 to 20 carbon atoms, an aryl group containing 6 to 20 carbon 35 atoms or an arylalkyl group containing 7 to 20 carbon atoms, X can be a ~ .
CA 022~8~8~ 1998-12-17 ,':
hydroxyl group or a hydrolyzable group, a can be an integer between 0 and ' 3 and b can have a value of 0, 1 or 2, the sum of a and b being 1 or greater than 1, and n is a number of 0 to 18, m is an integer of 0 to 4 and R3 represents - (CH2)m or - (CH2)m -N- (CH2)m -;
The reactive binder(s) contain(s) at least one silane-functional group co"esponding to formula (1). In a preferred embodiment, they contain on a statistical average between 1 and 3 silane-functional groups per molecuie.
The silane-functional groups are situated either at the ends of the macro-15 "~c'e~ ~'e (telechelic polymers) or are sl;llislic~lly distributed over the polymerchain. The hydrolyzable group X may be any hydrolyzable group known per se, for example an alkoxy group, acetoxy group, amino group, oxime group or amide group. The hydrolyzable group is preferably an alkoxy group, more preferably a methoxy or ethoxy group.
The silane-functional polyisobutylenes, silane-functional polybuta-dienes or silane-functional poly-a-olefins are produced in known manner. A
telechelic polymer containing olefinically unsaturated terminal groups is normally formed in the first stage and is reacted with organosilicon com-pounds in a second stage to form silane-functional polyisobutylene, hydrogenated polybutadiene or poly-a-olefin. The various versions of this production process for silane-functional polyisobutylenes or polybutadienes are described, for example, in the following patent applications: EP-A-287 025, EP-A- 452 875, EP-A- 434 840, EP-A-252 372, EP-A-79 456, EP-A- 537 660.
Other possible methods for the production of silane-functional polyisobutylenes or hydrogenated polybutadienes are described in EP-A-312 .... , .. ~ ~ .. ..
CA 022~8~8~ 1998-12-17 967. In addition, a hydroxyfunctional polyisobutylene, hydroxyfunctional polybutadiene or hydroxyfunctional poly-a-olefin can be prepared in a first process step and reacted with an isocyanate-functional silane in a second step.
Another possible method for producing the silane-functional binders comprises reacting the nonfunctional polyisobutylenes, hydrogenated polybutadienes or poly-a-olefins with corresponding organofunctional silanes in known manner in a grafting reaction. The silane groups are of course st~tistic~lly distributed in the polymer chain.
In principle, any rubber-like polymer with no functional groups may be used for the non-reactive binder. However, since the composition as a whole is pr~rer~bly intended for the production of spacer-free double glazing edge seals/bonds, the non-reactive binder should also be selected from polymers which guarantee low permeability to gases and, in particular, low permeability to water vapor of the glazing unit as a whole. The non-reactive binders may be selected from the group consisting of poly-a-olefins, rubbers based on styrene block copolymers, rubbers based on statistical diene homopolymers and/or copolymers and, in particular, polybutenes or butyl rubbers.
Suitable poly-a-olefins are, for example, ethylene/propylene elasto-mers, such as ethylene/propylene copolymers and terpolymers of ethylene and propylene with an unconjugated diene (EPDM). Propene/butene copolymers and ethylene/vinyl acetate are also suitable.
The rubbers based on styrene block copolymers are the diblock and triblock copolymers of styrene with a diene, for example butadiene or isoprene, which are commercially available, for example, under the name of Kraton from Shell. Hydrogenated or partly hydrogenated block copolymers may also be used.
Examples of the statistical diene homopolymers and copolymers are polybutadiene, polyisoprene, copolymers thereof and styrene/butadiene copolymers, acrylonitrile/butadiene copolymers and the partly hydrogenated CA 022~8~8~ 1998-12-17 .
or completely hydrogenated diene polymers of the last-mentioned group.
Natural rubber, more particularly epoxidized natural rubber, may also be used as a non-reactive binder.
By virtue of their particularly favorable barrier effect against water 5 vapor and gases, polybutenes and/or polyisobutene, polyolefins produced by slereospe~fic polymerization of 1-butene or isobutene and butyl rubbers, i.e.
copolymers or isobutylene with isoprene, are most particularly preferred.
The hotmelt adhesive compositions according to the invention may also contain plasticizers, although the plasticizers should be chosen with 10 particular care according to the following criteria:
- An extremely low percentage content of volatile components in order to avoid so-called fogging over the life of the double glazing unit.
Fogging is a well-known phenomenon whereby small quantities of volatile cor"ponents of the binder system first enter the space between the layers of glass and condense on the colder parts thereof.
- The barrier effect of the polymer matrix against water vapor and gases should not be adversely affected by the plasticizer.
Examples of suitable plasticizers are the phthalate plasticizers known per se based on phthalic acid alkyl or aryl esters, providing their volatile components are so small in number that the plasticizers do not cause any fogging and, in addition, the phthalate plasticizers are compatible with the binder system, i.e. have no tendency towards exudation.
Liquid polybutenes and polyisobutenes are most particularly preferred plasticizers.
The hotmelt adhesive compositions according to the invention may additionally contain components known per se, including in particular water-binding fillers, preferably the zeolites of the 3 A type known as molecular sieves in powder form. In addition, fine-particle inert fillers, for example ground or precipitated chalks, kaolins, clays and carbon blacks may be used.
The chalks, kaolins or clays may be used both in their surface-hydrophobi-CA 022~8~8~ 1998-12-17 '' cized form or even without any surface pretreatment.
In addition, the compositions contain organofunctional silanes as coupling agents and/or crosslinking agents, including for example 3-glycidyloxypropyl trialkoxysilane, 3-acryloxypropyl trialkoxysilane, 3-amino-propyl trialkoxysilane, vinyl trialkoxysilane, N-aminoethyl-3-aminopropyl methyl dialkoxysilane, phenylaminopropyl trialkoxysilane, aminoalkyl trialkoxydisilane or i-butyl methoxysilane. A particularly preferred alkoxy group is the methoxy or ethoxy group.
Suitable catalysts iare any known compounds which are capable of catalyzing the hydrolysis of the hydrolyzable groups of the silane groups and the subsequent condensation of the Si-OH group to siloxane groups (crossli"king reaction or coupling function). Organic compounds of divalent and tetravalent tin are most particularly preferred.
The choice of the antiager used, if any, is govemed by the composition of the binder. Antioxidanls of the sterically hindered phenol, thioether or highmo'ec~ weight mercapto compound type and UV stabilizers of the known ber~o~ 'P, benzophenone or HALS (hindered amine light stabilizer) type may be used. It can be of advantage to add known anti-ozonants. In exceptional cases, hydrolysis stabilizers may also have to be added.
Where the hotmelt adhesive compositions according to the invention are used for the production of multiple glazing units, the multiple glazing unitthus produced is distinguished by the following features in relation to the prior art:
- the adhesive mixture acts both as a spacer and as a matrix for the moisture-absorbing substance, - it also forms an elastic bond/seal at the edges of the glass layers, - the water harmful to the useful life of the double glazing unit is not only bound in the matrix by the molecular sieve, it is also at least partly consumed by a chemical reaction in the curing process.
A particular advantage is that all the process steps hitherto involved ~ .
CA 022~8~8~ 1998-12-17 ' in the formation of a conventional edge seal/bond are now combined into a single step. Another advantage is that, because it consists of only one material, a system of the type in question can be recycled after dismantling of the double glazing unit at the end of its useful life because, in conl, asl to 5 the prior art, it is not a composite material of polymer matrices differing in their composition.
The compositions according to the invention preferably consist of (a) silane-functional polyisobutylene, silane-functional hydrogenated polybutadiene or silane-functional poly-a-olefin 20 -70% by weight (b) butyl rubber 5 -30% by weight (c) poly-a-olefin 5 -30% by weight (d) molecular sieve of the zeolite 3A type20 -30% by weight (e) carbon black 5 -30% by weight (f) catalyst 0.1- 2%byweight (g) organosilane 0.1- 2%byweight The compositions may be produced in known manner by high-shear mixing of the components to homogeneity, optionally in vacuo or in an inert gas atmosphere. The components being mixed may have to be heated or 20 cooled. Since the hotmelt adhesive compositions react with moisture by crosslinking, the compositions have to be protected against moisture pending their final application by the user in order to guarantee adequate stability in storage.
In the embodiment as a one-component adhesive/sealant, all the 25 above-mentioned components are mixed together in the production process.
In the two-component embodiment, the catalyst(s) (f) are separately prepared in a paste of the non-reactive binder (b) and/or (c) and part of the filler (e) and optionally plasticizer as component B. The other constituents are prepared as component A, both components being mixed immediately before 30 application. In another embodiment, component A consists of constituents CA 022~8~8~ 1998-12-17 (a) to (g) while component B consists of a water-containing paste, the water optionally being present in this paste in the form of water-releasing com-pounds, for example salts containing water of crystallization. One advantage of this procedure is that it enables the compositions to be formulated in such 5 a way that a particularly rapid crosslinking reaction takes place, so that a double glazing seal/bond thus formed is capable of withstanding severe mechanical stressing after a particularly short time.
To produce the double glazing units, the layers of glass to be joined are either kept at the precl~tel ",ined distance apart in known manner and the 10 c~"~posilions are injected into the space between the layers at their marginsby means of an extruder-like applicator, optionally with heating and profiling.
By virtue of the hotmelt-like consistency of the composition, the edge seal/bond develops an early strength after cooling of the adhesive composi-tion sufficient to enable the double glazing units to be immediately further 15 p~ucesserl~ transported or stored. Ultimate strength is developed through the~osslinking of the silane groups of the reactive binder in combination with the organosilane added by reaction with the moisture in the space between the glass layers and/or the ambient air.
In another embodiment, the hotmelt adhesive is applied to the 20 peripheral edge of one layer of glass, optionally with heating and profiling, the second layer of glass or additional layers of glass are then positioned over the first in such a way that the layers of glass are exactly aligned one above the other. They are then pressed together in such a way that the adhesive completely wets the edges of both or all the layers of glass and the predeter-25 mined inter-layer spacing is reached. In this embodiment, too, the early strength of the edge seal/bond is developed during the cooling process whereas ultimate strength is achieved by crosslinking with moisture.
As mentioned above, the two components of the two-component hotmelt adhesives are mixed immediately before the application steps just 30 described. The edge seal/bond develops its ultimate strength more quickly in this embodiment than in the one-component version.
The reactive binder(s) contain(s) at least one silane-functional group co"esponding to formula (1). In a preferred embodiment, they contain on a statistical average between 1 and 3 silane-functional groups per molecuie.
The silane-functional groups are situated either at the ends of the macro-15 "~c'e~ ~'e (telechelic polymers) or are sl;llislic~lly distributed over the polymerchain. The hydrolyzable group X may be any hydrolyzable group known per se, for example an alkoxy group, acetoxy group, amino group, oxime group or amide group. The hydrolyzable group is preferably an alkoxy group, more preferably a methoxy or ethoxy group.
The silane-functional polyisobutylenes, silane-functional polybuta-dienes or silane-functional poly-a-olefins are produced in known manner. A
telechelic polymer containing olefinically unsaturated terminal groups is normally formed in the first stage and is reacted with organosilicon com-pounds in a second stage to form silane-functional polyisobutylene, hydrogenated polybutadiene or poly-a-olefin. The various versions of this production process for silane-functional polyisobutylenes or polybutadienes are described, for example, in the following patent applications: EP-A-287 025, EP-A- 452 875, EP-A- 434 840, EP-A-252 372, EP-A-79 456, EP-A- 537 660.
Other possible methods for the production of silane-functional polyisobutylenes or hydrogenated polybutadienes are described in EP-A-312 .... , .. ~ ~ .. ..
CA 022~8~8~ 1998-12-17 967. In addition, a hydroxyfunctional polyisobutylene, hydroxyfunctional polybutadiene or hydroxyfunctional poly-a-olefin can be prepared in a first process step and reacted with an isocyanate-functional silane in a second step.
Another possible method for producing the silane-functional binders comprises reacting the nonfunctional polyisobutylenes, hydrogenated polybutadienes or poly-a-olefins with corresponding organofunctional silanes in known manner in a grafting reaction. The silane groups are of course st~tistic~lly distributed in the polymer chain.
In principle, any rubber-like polymer with no functional groups may be used for the non-reactive binder. However, since the composition as a whole is pr~rer~bly intended for the production of spacer-free double glazing edge seals/bonds, the non-reactive binder should also be selected from polymers which guarantee low permeability to gases and, in particular, low permeability to water vapor of the glazing unit as a whole. The non-reactive binders may be selected from the group consisting of poly-a-olefins, rubbers based on styrene block copolymers, rubbers based on statistical diene homopolymers and/or copolymers and, in particular, polybutenes or butyl rubbers.
Suitable poly-a-olefins are, for example, ethylene/propylene elasto-mers, such as ethylene/propylene copolymers and terpolymers of ethylene and propylene with an unconjugated diene (EPDM). Propene/butene copolymers and ethylene/vinyl acetate are also suitable.
The rubbers based on styrene block copolymers are the diblock and triblock copolymers of styrene with a diene, for example butadiene or isoprene, which are commercially available, for example, under the name of Kraton from Shell. Hydrogenated or partly hydrogenated block copolymers may also be used.
Examples of the statistical diene homopolymers and copolymers are polybutadiene, polyisoprene, copolymers thereof and styrene/butadiene copolymers, acrylonitrile/butadiene copolymers and the partly hydrogenated CA 022~8~8~ 1998-12-17 .
or completely hydrogenated diene polymers of the last-mentioned group.
Natural rubber, more particularly epoxidized natural rubber, may also be used as a non-reactive binder.
By virtue of their particularly favorable barrier effect against water 5 vapor and gases, polybutenes and/or polyisobutene, polyolefins produced by slereospe~fic polymerization of 1-butene or isobutene and butyl rubbers, i.e.
copolymers or isobutylene with isoprene, are most particularly preferred.
The hotmelt adhesive compositions according to the invention may also contain plasticizers, although the plasticizers should be chosen with 10 particular care according to the following criteria:
- An extremely low percentage content of volatile components in order to avoid so-called fogging over the life of the double glazing unit.
Fogging is a well-known phenomenon whereby small quantities of volatile cor"ponents of the binder system first enter the space between the layers of glass and condense on the colder parts thereof.
- The barrier effect of the polymer matrix against water vapor and gases should not be adversely affected by the plasticizer.
Examples of suitable plasticizers are the phthalate plasticizers known per se based on phthalic acid alkyl or aryl esters, providing their volatile components are so small in number that the plasticizers do not cause any fogging and, in addition, the phthalate plasticizers are compatible with the binder system, i.e. have no tendency towards exudation.
Liquid polybutenes and polyisobutenes are most particularly preferred plasticizers.
The hotmelt adhesive compositions according to the invention may additionally contain components known per se, including in particular water-binding fillers, preferably the zeolites of the 3 A type known as molecular sieves in powder form. In addition, fine-particle inert fillers, for example ground or precipitated chalks, kaolins, clays and carbon blacks may be used.
The chalks, kaolins or clays may be used both in their surface-hydrophobi-CA 022~8~8~ 1998-12-17 '' cized form or even without any surface pretreatment.
In addition, the compositions contain organofunctional silanes as coupling agents and/or crosslinking agents, including for example 3-glycidyloxypropyl trialkoxysilane, 3-acryloxypropyl trialkoxysilane, 3-amino-propyl trialkoxysilane, vinyl trialkoxysilane, N-aminoethyl-3-aminopropyl methyl dialkoxysilane, phenylaminopropyl trialkoxysilane, aminoalkyl trialkoxydisilane or i-butyl methoxysilane. A particularly preferred alkoxy group is the methoxy or ethoxy group.
Suitable catalysts iare any known compounds which are capable of catalyzing the hydrolysis of the hydrolyzable groups of the silane groups and the subsequent condensation of the Si-OH group to siloxane groups (crossli"king reaction or coupling function). Organic compounds of divalent and tetravalent tin are most particularly preferred.
The choice of the antiager used, if any, is govemed by the composition of the binder. Antioxidanls of the sterically hindered phenol, thioether or highmo'ec~ weight mercapto compound type and UV stabilizers of the known ber~o~ 'P, benzophenone or HALS (hindered amine light stabilizer) type may be used. It can be of advantage to add known anti-ozonants. In exceptional cases, hydrolysis stabilizers may also have to be added.
Where the hotmelt adhesive compositions according to the invention are used for the production of multiple glazing units, the multiple glazing unitthus produced is distinguished by the following features in relation to the prior art:
- the adhesive mixture acts both as a spacer and as a matrix for the moisture-absorbing substance, - it also forms an elastic bond/seal at the edges of the glass layers, - the water harmful to the useful life of the double glazing unit is not only bound in the matrix by the molecular sieve, it is also at least partly consumed by a chemical reaction in the curing process.
A particular advantage is that all the process steps hitherto involved ~ .
CA 022~8~8~ 1998-12-17 ' in the formation of a conventional edge seal/bond are now combined into a single step. Another advantage is that, because it consists of only one material, a system of the type in question can be recycled after dismantling of the double glazing unit at the end of its useful life because, in conl, asl to 5 the prior art, it is not a composite material of polymer matrices differing in their composition.
The compositions according to the invention preferably consist of (a) silane-functional polyisobutylene, silane-functional hydrogenated polybutadiene or silane-functional poly-a-olefin 20 -70% by weight (b) butyl rubber 5 -30% by weight (c) poly-a-olefin 5 -30% by weight (d) molecular sieve of the zeolite 3A type20 -30% by weight (e) carbon black 5 -30% by weight (f) catalyst 0.1- 2%byweight (g) organosilane 0.1- 2%byweight The compositions may be produced in known manner by high-shear mixing of the components to homogeneity, optionally in vacuo or in an inert gas atmosphere. The components being mixed may have to be heated or 20 cooled. Since the hotmelt adhesive compositions react with moisture by crosslinking, the compositions have to be protected against moisture pending their final application by the user in order to guarantee adequate stability in storage.
In the embodiment as a one-component adhesive/sealant, all the 25 above-mentioned components are mixed together in the production process.
In the two-component embodiment, the catalyst(s) (f) are separately prepared in a paste of the non-reactive binder (b) and/or (c) and part of the filler (e) and optionally plasticizer as component B. The other constituents are prepared as component A, both components being mixed immediately before 30 application. In another embodiment, component A consists of constituents CA 022~8~8~ 1998-12-17 (a) to (g) while component B consists of a water-containing paste, the water optionally being present in this paste in the form of water-releasing com-pounds, for example salts containing water of crystallization. One advantage of this procedure is that it enables the compositions to be formulated in such 5 a way that a particularly rapid crosslinking reaction takes place, so that a double glazing seal/bond thus formed is capable of withstanding severe mechanical stressing after a particularly short time.
To produce the double glazing units, the layers of glass to be joined are either kept at the precl~tel ",ined distance apart in known manner and the 10 c~"~posilions are injected into the space between the layers at their marginsby means of an extruder-like applicator, optionally with heating and profiling.
By virtue of the hotmelt-like consistency of the composition, the edge seal/bond develops an early strength after cooling of the adhesive composi-tion sufficient to enable the double glazing units to be immediately further 15 p~ucesserl~ transported or stored. Ultimate strength is developed through the~osslinking of the silane groups of the reactive binder in combination with the organosilane added by reaction with the moisture in the space between the glass layers and/or the ambient air.
In another embodiment, the hotmelt adhesive is applied to the 20 peripheral edge of one layer of glass, optionally with heating and profiling, the second layer of glass or additional layers of glass are then positioned over the first in such a way that the layers of glass are exactly aligned one above the other. They are then pressed together in such a way that the adhesive completely wets the edges of both or all the layers of glass and the predeter-25 mined inter-layer spacing is reached. In this embodiment, too, the early strength of the edge seal/bond is developed during the cooling process whereas ultimate strength is achieved by crosslinking with moisture.
As mentioned above, the two components of the two-component hotmelt adhesives are mixed immediately before the application steps just 30 described. The edge seal/bond develops its ultimate strength more quickly in this embodiment than in the one-component version.
Claims (13)
1. A hotmelt adhesive composition containing a mixture of at least one reactive binder and at least one non-reactive binder, characterized in that at least one reactive binder consists of silane-functional polyisobutylenes and/or silane-functional hydrogenated polybutadienes and/or silane-functional poly-.alpha.-olefins and the non-reactive binder(s) is selected from the group consisting of butyl rubbers, poly-.alpha.-olefins, polybutenes, rubbers based on styrene block copolymers, rubbers based on statistical diene homopolymers and/or copolymers.
2. A composition as claimed in claim 1, characterized in that the silane-functional groups of the reactive binder(s) are represented by formula (1):
where -A- can represent - (CH2)m - (2) -S-(CH2)m - (3) or (4) and R1 and R2 may be the same or different and represent an alkyl group containing 1 to 20 carbon atoms, an aryl group containing 6 to 20 carbon atoms or an arylalkyl group containing 7 to 20 carbon atoms, X can be a hydroxyl group or a hydrolyzable group, a = 0, 1, 2 or 3 and b = 0, 1 or 2, the sum of a and b being 1 or greater than 1, and n is an integer of 0 to 18, m is an integer of 0 to 4 and R3 represents - (CH2)m or
where -A- can represent - (CH2)m - (2) -S-(CH2)m - (3) or (4) and R1 and R2 may be the same or different and represent an alkyl group containing 1 to 20 carbon atoms, an aryl group containing 6 to 20 carbon atoms or an arylalkyl group containing 7 to 20 carbon atoms, X can be a hydroxyl group or a hydrolyzable group, a = 0, 1, 2 or 3 and b = 0, 1 or 2, the sum of a and b being 1 or greater than 1, and n is an integer of 0 to 18, m is an integer of 0 to 4 and R3 represents - (CH2)m or
3. A composition as claimed in at least one of the preceding claims, characterized in that it contains (a) 20 to 70% by weight of silane-functional binder, (b) 5 to 30% by weight of non-reactive binder, (c) 20 to 30% by weight of water-binding fillers, preferably molecular sieves of the 3A type, (d) 5 to 30% by weight of fine-particle inert fillers selected from the group consisting of ground or precipitated chalks, kaolins, clays, carbon blacks, (e) 0.1 to 2% by weight of organofunctional silanes, (f) 0.1 to 2% by weight of catalysts, (g) 0 to 3% by weight of antiagers selected from the group consisting of antioxidants, UV stabilizers, anti-ozonants, hydrolysis stabilizers.
4. A composition as claimed in claim 3, characterized in that it contains 2 to 40% by weight of plasticizer.
5. A two-component composition as claimed in claim 3 or 4, characterized in that one component contains constituents (a) to (e) and (g) and the second component consists of constituents (b), (c), (d), (f) and optionally plasticizer.
6. A two-component composition as claimed in claim 3 or 4, characterized in that one component contains constituents (a) to (g) and the second component consists of a water-containing paste which contains water in dissolved, adsorbed or emulsified form or in the form of solid water-releasing substances and optionally a non-reactive binder (b) and/or plasticizer.
7. A process for producing the compositions claimed in at least one of the preceding claims, characterized in that the constituents are subjected to high-shear mixing to homogeneity, optionally in vacuo or in a dry inert gas atmosphere.
8. The use of the compositions claimed in at least one of the preceding claims as a one-component or two-component adhesive for the production of double glazing or multiple glazing.
9. Double or multiple glazing, characterized in that the compositions claimed in at least one of the preceding claims serve simultaneously as - spacers between the individual layers of glass, - a matrix for the moisture-absorbing substances, - a water vapor barrier and - an elastic edge seal/bond for the glazing.
10. A process for the production of double glazing as claimed in claim 9, characterized by the following process steps:
(a) the layers of glass to be joined are held at the predetermined distance apart, (b) the compositions claimed in at least one of claims 1 to 4 are injected between the glass layers at their edges, optionally with heating and profiling, (c) the composition cures to form an elastic seal/bond by absorbing moisture from the space between the layers of glass and/or the ambient air.
(a) the layers of glass to be joined are held at the predetermined distance apart, (b) the compositions claimed in at least one of claims 1 to 4 are injected between the glass layers at their edges, optionally with heating and profiling, (c) the composition cures to form an elastic seal/bond by absorbing moisture from the space between the layers of glass and/or the ambient air.
11. A process as claimed in claim 9, characterized in that the components of the compositions claimed in claim 5 or 6 are mixed immediately before step (b) is carried out.
12. A process for the production of double glazing as claimed in claim 9, characterized by the following process steps:
(a) the compositions claimed in at least one of claims 1 to 4 are applied to the edge of one layer of glass, optionally with heating and profiling, (b) the second layer of glass or additional layers of glass is/are positioned over the first in such a way that the layers of are in exact alignment one above the other, (c) the layers of glass are pressed together in such a way that the adhesive completely wets the edges of both or all layers of glass and the predetermined distance between the layers is reached, (d) the adhesive composition occurs to form an elastic seal/bond by absorbing moisture from the space between the layers of glass and/or the ambient air.
(a) the compositions claimed in at least one of claims 1 to 4 are applied to the edge of one layer of glass, optionally with heating and profiling, (b) the second layer of glass or additional layers of glass is/are positioned over the first in such a way that the layers of are in exact alignment one above the other, (c) the layers of glass are pressed together in such a way that the adhesive completely wets the edges of both or all layers of glass and the predetermined distance between the layers is reached, (d) the adhesive composition occurs to form an elastic seal/bond by absorbing moisture from the space between the layers of glass and/or the ambient air.
13. A process as claimed in claim 12, characterized in that the components of the compositions claimed in claim 5 or 6 are mixed immediately before step (a) is carried out.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19624236A DE19624236A1 (en) | 1996-06-18 | 1996-06-18 | Reactive hot melt adhesive composition for insulating glass |
DE19624236.3 | 1996-06-18 |
Publications (1)
Publication Number | Publication Date |
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CA2258585A1 true CA2258585A1 (en) | 1997-12-24 |
Family
ID=7797239
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002258585A Abandoned CA2258585A1 (en) | 1996-06-18 | 1997-06-09 | Reactive melt adhesive composition for double glazing |
Country Status (8)
Country | Link |
---|---|
EP (1) | EP0906378B2 (en) |
JP (1) | JP2000512333A (en) |
AT (1) | ATE226618T1 (en) |
CA (1) | CA2258585A1 (en) |
DE (2) | DE19624236A1 (en) |
NO (1) | NO985925L (en) |
PL (1) | PL330317A1 (en) |
WO (1) | WO1997048778A1 (en) |
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US6649695B1 (en) | 1999-08-09 | 2003-11-18 | Basf Aktiengesellschaft | Elastic sealing material on the basis of block copolymers made of isobutene and vinyl aromatic monomers |
US6803412B2 (en) | 2003-03-13 | 2004-10-12 | H.B. Fuller Licensing & Financing Inc. | Moisture curable hot melt sealants for glass constructions |
US7204902B2 (en) | 2003-03-11 | 2007-04-17 | H.B. Fuller Licensing & Finance Inc | Low-temperature press process for making insulating glass assemblies |
US7259209B2 (en) | 2000-03-28 | 2007-08-21 | H.B.Fuller Licensing & Financing, Inc. | Reactive hot-melt-type adhesive granules for fabricating insulating glass |
US7270859B2 (en) | 2003-05-28 | 2007-09-18 | H.B. Fuller Licensing & Financing Inc. | Insulating glass assembly including a polymeric spacing structure |
US8080308B2 (en) | 2003-03-11 | 2011-12-20 | H.B. Fuller Company | One-part moisture curable hot melt silane functional poly-alpha-olefin sealant composition |
CN101878263B (en) * | 2007-09-20 | 2013-08-14 | 柯梅林化工厂公司 | Composite edge for producing double or multiple pane insulation glass or solar modules |
US10099464B2 (en) | 2012-05-03 | 2018-10-16 | Henkel Ag & Co. Kgaa | Two-component hot-melt adhesive |
US10627306B2 (en) | 2014-09-30 | 2020-04-21 | Panasonic Intellectual Property Management Co., Ltd. | Glass panel unit and inspection method thereof |
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EP0827994B1 (en) * | 1996-09-04 | 2002-12-18 | Degussa AG | Use of grafted amorphous poly-alfa-olefins as moisture-curable raw material for adhesives and as adhesives |
DE19821355B4 (en) * | 1998-05-13 | 2005-02-24 | Chemetall Gmbh | Use of a sealant for the production of multi-pane insulating glass |
US6121354A (en) * | 1998-11-19 | 2000-09-19 | Bostik, Inc. | High performance single-component sealant |
DE10080292D2 (en) | 1999-02-11 | 2002-01-31 | Jowat Lobers U Frank Gmbh & Co | Multi-component coating and adhesive material |
WO2000075226A1 (en) | 1999-06-04 | 2000-12-14 | Kaneka Corporation | Curable composition and method of use thereof |
DE10163844C1 (en) * | 2001-12-22 | 2003-10-09 | Henkel Teroson Gmbh | Twin-pane double glazing structure is assembled automatically, with extruded spacers applied to the assembled spoke frame with end pieces at the glass pane, for the second pane to be pressed over them into the required pane gap |
EP1462500A1 (en) * | 2003-03-28 | 2004-09-29 | Le Joint Francais | Single component, chemically curing warm applied sealant for durable insulating glazing units |
JP2005281404A (en) * | 2004-03-29 | 2005-10-13 | Aica Kogyo Co Ltd | Moisture curable resin composition and its curing acceleration method |
CN101484502B (en) | 2006-07-03 | 2012-05-30 | 陶氏康宁公司 | Chemically curing all-in-one warm edge spacer and seal |
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JP5375357B2 (en) * | 2009-06-18 | 2013-12-25 | 横浜ゴム株式会社 | Reactive hot melt adhesive composition |
CN102695769A (en) * | 2009-10-14 | 2012-09-26 | 阿德科产品公司 | Use of carbon black for oxidative and heat stability in solar module applications |
CN102742143A (en) * | 2009-10-14 | 2012-10-17 | 阿德科产品公司 | Edge sealant composition with reactive or unsaturated polyolefins |
DE102009044892A1 (en) | 2009-12-14 | 2011-06-16 | Kömmerling Chemische Fabrik GmbH | Window or door comprises attached insulation glass disk which is connected with wing profile or frame profile by adhesive, where frame profile is, particularly made of plastic material or wood or metal |
US9573347B2 (en) | 2009-12-15 | 2017-02-21 | Teknor Apex Company | Thermoplastic elastomer with desirable grip especially during wet conditions |
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-
1996
- 1996-06-18 DE DE19624236A patent/DE19624236A1/en not_active Ceased
-
1997
- 1997-06-09 EP EP97928165A patent/EP0906378B2/en not_active Expired - Lifetime
- 1997-06-09 CA CA002258585A patent/CA2258585A1/en not_active Abandoned
- 1997-06-09 AT AT97928165T patent/ATE226618T1/en not_active IP Right Cessation
- 1997-06-09 DE DE59708569T patent/DE59708569D1/en not_active Expired - Lifetime
- 1997-06-09 JP JP10502197A patent/JP2000512333A/en not_active Withdrawn
- 1997-06-09 WO PCT/EP1997/002995 patent/WO1997048778A1/en active IP Right Grant
- 1997-06-09 PL PL97330317A patent/PL330317A1/en unknown
-
1998
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US6649695B1 (en) | 1999-08-09 | 2003-11-18 | Basf Aktiengesellschaft | Elastic sealing material on the basis of block copolymers made of isobutene and vinyl aromatic monomers |
US7259209B2 (en) | 2000-03-28 | 2007-08-21 | H.B.Fuller Licensing & Financing, Inc. | Reactive hot-melt-type adhesive granules for fabricating insulating glass |
US7204902B2 (en) | 2003-03-11 | 2007-04-17 | H.B. Fuller Licensing & Finance Inc | Low-temperature press process for making insulating glass assemblies |
US7414090B2 (en) | 2003-03-11 | 2008-08-19 | H.B. Fuller Licensing & Financing, Inc | Low-temperature press process for making insulating glass assemblies |
US8080308B2 (en) | 2003-03-11 | 2011-12-20 | H.B. Fuller Company | One-part moisture curable hot melt silane functional poly-alpha-olefin sealant composition |
US6803412B2 (en) | 2003-03-13 | 2004-10-12 | H.B. Fuller Licensing & Financing Inc. | Moisture curable hot melt sealants for glass constructions |
US7270859B2 (en) | 2003-05-28 | 2007-09-18 | H.B. Fuller Licensing & Financing Inc. | Insulating glass assembly including a polymeric spacing structure |
CN101878263B (en) * | 2007-09-20 | 2013-08-14 | 柯梅林化工厂公司 | Composite edge for producing double or multiple pane insulation glass or solar modules |
US10099464B2 (en) | 2012-05-03 | 2018-10-16 | Henkel Ag & Co. Kgaa | Two-component hot-melt adhesive |
US10627306B2 (en) | 2014-09-30 | 2020-04-21 | Panasonic Intellectual Property Management Co., Ltd. | Glass panel unit and inspection method thereof |
Also Published As
Publication number | Publication date |
---|---|
WO1997048778A1 (en) | 1997-12-24 |
ATE226618T1 (en) | 2002-11-15 |
DE19624236A1 (en) | 1998-01-08 |
NO985925D0 (en) | 1998-12-17 |
PL330317A1 (en) | 1999-05-10 |
EP0906378B2 (en) | 2008-03-12 |
EP0906378A1 (en) | 1999-04-07 |
DE59708569D1 (en) | 2002-11-28 |
JP2000512333A (en) | 2000-09-19 |
NO985925L (en) | 1998-12-17 |
EP0906378B1 (en) | 2002-10-23 |
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Legal Events
Date | Code | Title | Description |
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EEER | Examination request | ||
FZDE | Discontinued |