WO2005058598A1 - Use of pet film primed with polyallylamine coatings in laminated glass glazing constructions - Google Patents

Use of pet film primed with polyallylamine coatings in laminated glass glazing constructions Download PDF

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Publication number
WO2005058598A1
WO2005058598A1 PCT/US2004/042266 US2004042266W WO2005058598A1 WO 2005058598 A1 WO2005058598 A1 WO 2005058598A1 US 2004042266 W US2004042266 W US 2004042266W WO 2005058598 A1 WO2005058598 A1 WO 2005058598A1
Authority
WO
WIPO (PCT)
Prior art keywords
laminate
polymer
primer
pet
pvb
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.)
Ceased
Application number
PCT/US2004/042266
Other languages
English (en)
French (fr)
Inventor
Jerrel C. Anderson
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Priority to JP2006544132A priority Critical patent/JP2007513813A/ja
Priority to EP20040814448 priority patent/EP1697128A1/en
Publication of WO2005058598A1 publication Critical patent/WO2005058598A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C55/00—Shaping by stretching, e.g. drawing through a die; Apparatus therefor
    • B29C55/02—Shaping by stretching, e.g. drawing through a die; Apparatus therefor of plates or sheets
    • B29C55/023—Shaping by stretching, e.g. drawing through a die; Apparatus therefor of plates or sheets using multilayered plates or sheets
    • B29C55/026—Shaping by stretching, e.g. drawing through a die; Apparatus therefor of plates or sheets using multilayered plates or sheets of preformed plates or sheets coated with a solution, a dispersion or a melt of thermoplastic material
    • 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
    • B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
    • B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
    • B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
    • B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
    • B32B17/1055—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer
    • 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
    • B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
    • B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
    • B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
    • B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
    • B32B17/1055—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer
    • B32B17/10743—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer containing acrylate (co)polymers or salts thereof
    • 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
    • B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
    • B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
    • B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
    • B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
    • B32B17/1055—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer
    • B32B17/10761—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer containing vinyl acetal
    • 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
    • B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
    • B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
    • B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
    • B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
    • B32B17/10807—Making laminated safety glass or glazing; Apparatus therefor
    • B32B17/10816—Making laminated safety glass or glazing; Apparatus therefor by pressing
    • B32B17/10825—Isostatic pressing, i.e. using non rigid pressure-exerting members against rigid parts
    • B32B17/10834—Isostatic pressing, i.e. using non rigid pressure-exerting members against rigid parts using a fluid
    • B32B17/10844—Isostatic pressing, i.e. using non rigid pressure-exerting members against rigid parts using a fluid using a membrane between the layered product and the fluid
    • B32B17/10853—Isostatic pressing, i.e. using non rigid pressure-exerting members against rigid parts using a fluid using a membrane between the layered product and the fluid the membrane being bag-shaped
    • 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
    • B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B27/08—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/12—Bonding of a preformed macromolecular material to the same or other solid material such as metal, glass, leather, e.g. using adhesives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/0427—Coating with only one layer of a composition containing a polymer binder
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/043—Improving the adhesiveness of the coatings per se, e.g. forming primers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/046—Forming abrasion-resistant coatings; Forming surface-hardening coatings
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2067/00—Use of polyesters or derivatives thereof, as moulding material
    • 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
    • B32B2605/00—Vehicles
    • B32B2605/006—Transparent parts other than made from inorganic glass, e.g. polycarbonate glazings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
    • C08J2367/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2439/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Derivatives of such polymers
    • 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
    • Y10T156/00—Adhesive bonding and miscellaneous chemical manufacture
    • Y10T156/10—Methods of surface bonding and/or assembly therefor
    • Y10T156/1089—Methods of surface bonding and/or assembly therefor of discrete laminae to single face of additional lamina
    • 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
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    • Y10T156/1092—All laminae planar and face to face
    • 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
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    • Y10T428/31507—Of polycarbonate
    • 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
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    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, 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
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    • Y10T428/31565—Next to polyester [polyethylene terephthalate, etc.]
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    • Y10T428/31598—Next to silicon-containing [silicone, cement, etc.] layer
    • Y10T428/31601—Quartz or glass
    • 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
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    • Y10T428/31616—Next to polyester [e.g., alkyd]
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    • Y10T428/31942—Of aldehyde or ketone condensation product

Definitions

  • This invention relates to laminates used in glazing applications. This invention particularly relates to a process for improving adhesion between layers in glazing laminates.
  • PET film can be used as a laminate layer in laminated glazing products.
  • the PET layer can be in contact with other polymeric layers of the laminate.
  • Imbedded film applications for example, MET is PET imbedded between layers of PVB
  • Glass/plastic laminates that is, laminates having glass on one outer side and a hard plastic or hardcoated plastic on the other outer side
  • made using PVB interlayer with a PET film outer layer can be quite compressible because of the soft underlying PVB interlayer.
  • Such laminates are vulnerable to gouges and impressions when hard objects impact them or are pressed against them for some time. If the impressions are deep, they can become permanent and this mars the appearance of glazing using such glass plastic laminates .
  • Harder interlayers would make the plastic side of glass/plastic laminates harder and less prone to gouging and pressure-induced impressions.
  • use of such harder interlayers has been prevented by the lack of a sufficiently adherable PET film.
  • PET film treated by electrical discharge, various plasma treatments, or flame treatment does not adhere well to harder interlayers such as ionoplast sheeting, for example DuPont' s SENTRYGLASTM-PLUS (SGP) interlayer.
  • PET laminates such as those described hereinabove
  • PARC polysiloxane abrasion resistant coating
  • the adhesion strength as measured by the 90-degree angle peel test, averages about 10 lb/inch.
  • the flame treatment is done in a separate operation from the PET film casting.
  • U.S. Pat. No. 5,415,942 describes a hydroxy-acrylic hydrosol primer coating that, when applied to one side of a PET film, greatly improves adhesion of the PARC. However it does not improve adhesion of the PET to the PVB interlayer.
  • the primed film still needs to be flame treated on the non-primed side.
  • the adhesion between PVB and ionoplast resins is poor, and so laminates having these two polymer interlayers in contact are not viable for many of the applications in which these interlayer materials find use.
  • the present invention is a laminate comprising at least one layer of an polyallylamine- based coating that is adjacent to and in direct contact with at least one other polymeric layer comprising a polymer selected from the group consisting of: PET; PVB; ionoplast resin; polyurethanes; polyvinyl chlorides; polycarbonates; polyacetals; ethylene acid copolymers (which are inclusive of ethylene acid terpolymers) ; polyolefins, including polyethylenes and polypropylenes .
  • a polymer selected from the group consisting of: PET; PVB; ionoplast resin; polyurethanes; polyvinyl chlorides; polycarbonates; polyacetals; ethylene acid copolymers (which are inclusive of ethylene acid terpolymers) ; polyolefins, including polyethylenes and polypropylenes .
  • the present invention is a laminate comprising: a three-layer laminate structure comprising (1) a PET layer that is in contact with (2) a polyester film comprising a polyallylamine-based coating on each of its two surfaces, wherein the second surface is in direct contact with (3) a polyvinyl butyral (PVB) layer.
  • a three-layer laminate structure comprising (1) a PET layer that is in contact with (2) a polyester film comprising a polyallylamine-based coating on each of its two surfaces, wherein the second surface is in direct contact with (3) a polyvinyl butyral (PVB) layer.
  • PVB polyvinyl butyral
  • the present invention is a laminate comprising: a laminate structure comprising (1) an ionoplast resin layer that is in contact with (2) a polyvinyl butyral (PVB) layer, wherein the peel strength is at least 10 lb/inch between the ionoplast and the PVB layers and wherein at least one of the polymer layers comprises a polyester film comprising a polyallylamine-based coating on each of its two surfaces .
  • PVB polyvinyl butyral
  • the present invention is a glass laminate comprising a three-layer laminate structure comprising: (1) a polymer selected from the group consisting of polyethylene terphthalate (PET) ; polyvinylbutyral (PVB) ; and ethylene acid copolymer ionomer (ionoplast resin) , said polymer being in contact with (2) an polyallylamine-based coating that is in contact with (3) a polymer selected from the group consisting of PET; PVB; ionoplast resin; polyurethanes; polyvinyl chlorides; polycarbonates; polyacetals; ethylene acid copolymers (which are inclusive of ethylene acid terpolymers) ; polyolefins, including polyethylenes and polypropylenes.
  • PET polyethylene terphthalate
  • PVB polyvinylbutyral
  • ionoplast resin ethylene acid copolymer ionomer
  • the present invention is a process for preparing a laminate comprising the steps of: (1) applying a polyester film having a coating of polyallylamine-based polymer (PRIMER) to at least one surface of a polymer selected from the group consisting of: polyethylene terphthalate (PET) ; polyvinylbutyral (PVB) ; and ethylene acid copolymer ionomer (ionoplast resin); and (2) contacting the coated polyallylamine coated surface with at least one polymeric layer selected from a polymer in the group consisting of: PET; PVB; ionoplast resin; polyurethanes; polyvinyl chlorides; polycarbonates; polyacetals; ethylene acid copolymers (which are inclusive of ethylene acid terpolymers) ; polyolefins, including polyethylenes and polypropylenes wherein the PRIMER is applied in-line with the polymer sheet, and wherein the PRIMER has been heated to a temperature above about 170 °C and stretched
  • the present invention is a polymer which has adhered to at least one of its surfaces a polyester (PET) layer wherein the PET has a coating of a polyallylamine-based primer applied to at least one of its surfaces, preferably to both surfaces of the PET.
  • PET polyester
  • the primer and its application to the PET polymeric layer are described in U.S. Pat. Nos. 5,411,845; 5,770,312; 5,690,994; and 5,698,329.
  • the PET film is extruded and cast as a film by conventional methods, and the polyallylamine coating is applied to the PET film either before stretching or between the machine direction stretching and transverse direction stretching operations, and/or after the two stretching operations and heat setting in the stenter oven. It is preferable that the coating be applied before the transverse stretching operation so that the coated PET web is heated under restraint to a temperature of about 220 °C in the stenter oven in order to cure the polyallylamine to the PET surface. In addition to this cured coating, an additional polyallylamine coating can be applied on it after the stretching and stenter oven heat setting in order to obtain a thicker overall coating.
  • the coated PET treated in this general manner is the primer (PRIMER) used herein to enhance the adhesion between dissimilar polymeric layers in a laminate construction.
  • Adhesive strength in a laminate of the present invention is determined by the 90° peel test.
  • the adhesive strength between dissimilar polymer layers in the present invention can be about zero (0) to about less than 10 lb/inch without any treatment to enhance adhesion, and with flame treatment the adhesive strength can be improved to about 10 lb/inch.
  • Using a PRIMER as described herein can improve the peel strength to at least about 10 lb/in, and preferably to at least 15 lb/inch.
  • Suitable polymers useful in a laminate of the present invention include, for example: PET; PVB; ionoplast resins, which are ethylene acid copolymer ionomers; polyurethanes; polyvinyl chlorides; polycarbonates; polyacetals; ethylene acid copolymers (which, are inclusive of ethylene acid terpolymers) ; polyolefins, including polyethylenes and polypropylenes.
  • PET PET
  • PVB and ionoplast resins
  • PVB is a commercially available product that can be obtained from E.I.
  • Ionoplast resins suitable for use herein are copolymers (inclusive of terpolymers) of ethylene and unsaturated carboxylic acids wherein at least a portion of the acid groups in the copolymer have been neutralized to the salt form of the acid. Extruded sheets of ionoplast resin suitable for use in the present invention can be obtained from DuPont under the trade name of SentryGlass® Plus (SGP) . Polyester films (PET) are well-known polymer films that can also be obtained commercially from DuPont.
  • PET suitable for use herein can additionally comprise a hardcoat such as an abrasion resistant polysiloxane material or an oligomeric coating as described in U.S. Application Serial No. 60/499949 on one of its surfaces.
  • the polysiloxane coated PET can be obtained commercially from DuPont.
  • laminates of PET and other polymers such as PVB and SGP, it can be conventional to enhance the adhesion of the PET to the other polymers by some treatment step such as a flame treatment.
  • adhesion of PET to any of the other polymers can be improved by applying the PRIMER to either surface of the dissimilar polymers prior to laminating the layers using conventional laminating methods.
  • the adhesion between PVB and ionoplast resin can be greatly improved by applying the PRIMER to the surface of either polymer layer prior to lamination.
  • a laminate can be constructed wherein ionoplast resin and PVB are adhered using the PRIMER and thus provide a [Glass/PVB/PRIMER/ionoplast/PRIMER/PVB/Glass] laminate, for example, having enhanced penetration resistance relative to conventional Glass/PVB/Glass laminates, without losing the desirable properties of the conventional PVB glass laminates.
  • Laminated polymer layers comprising the PRIMER can be used in the construction of other multilayer laminates.
  • the laminate constructions obtained from PET/PRIMER/PVB can be laminated to glass, or between other polymeric layers, or a combination thereof.
  • a PET layer can comprise a hardcoat on its surface, and thus be used in glass/plastic product applications such as where Spallshield® or SentryGlass® laminated products find use.
  • the laminate can be imbedded between other polymeric laminate layers without the hardcoat on the surface of the PET.
  • the PRIMER adheres very well to both PVB resins and ionoplast resins, and this makes possible its use with either interlayer in glass plastic glazing.
  • Example 1 Four PET films primed in-line with three different primer coatings along with a flame treated PET film as control, were laminated to glass with the primed sides against high adhesion grade BUTACITETM BE-1028 PVB sheeting. The PET films were then tested for peel adhesion strength against the PVB sheeting. These samples were laminated to glass using an air autoclave at a temperature of 135 °C held for 30 minutes at a pressure of 17 atmospheres. The samples were vacuum bagged to remove air from between the PET and PVB and glass layers. A glass cover plate was used to maintain optical flatness and to insure complete contact between all layers. This cover plate was removed from the PET side of each laminate after the autoclaving step. The primed films were various grades of polyester films .
  • the PET film used for the PRIMER was primed in- line on both sides with a crosslinked polyallylamine coating
  • the second PET film used as a comparative (PETC1) was primed on one side in-line with a crosslinked acrylic hydrosol coating containing acrylamide functionality
  • two other comparative PET films (PETC2 and PETC3) primed in-line on one side with a crosslinked 2-hydroxyethylacrylate functionalized acrylic hydrosol coating, available from DuPont, both single coating and stretched and double coated.
  • the flame treated control film was PETC4, and is the same PET film base as used in the PETC2 and PETC3 primed examples, except that instead of priming it was flame treated in a separate operation from the film making process, i.e. not flame treated in-line.
  • the finished laminates were clear and suitable for 90 degree angle peel testing.
  • the laminate structure was: PET/PVB/GLASS.
  • the laminates were peeled at a 90-degree angle using an INSTRUMENTORS, Inc., Model SP-102B-3M90 SLIP/PEEL Tester.
  • the laminates were peeled at rates of 1 inch and 2 inches per minute.
  • the only primer that enhanced adhesion between the PET film and PVB sheeting was the polyallylamine. The adhesion was too high to measure.
  • Example 2 This example is the same as Example 1, but with these changes: (1) 95 mil thick SENTRYGLASTM-PLUS ionoplast sheeting was used as the interlayer instead of PVB, and (2) PRIMER and PETC4 were the only PET films tested. The 90-degree peel results are tabulated below: Table 2
  • Example 3 Laminated glass panels imbedding PET films were made and tested for compressive shear strength. The structures tested were these: Structure A:
  • GLASS/PVB/PET/PVB/PET/PVB/GLASS PVB layers each 15 mils thick
  • Two PET films were tested for compressive shear strength (CSS) : (1) PETC4 (7 mil thick), and (2) 6.50 mil thick PRIMER film.
  • the compressive shear strengths of the laminates described herein were determined using the method described in W09961243 (Al) and detailed here.
  • l"xl" (25 mm x 25 mm) chips are sawed from the laminate and conditioned in a room controlled at 23°C+2°C and 50%+l% relative humidity for one hour prior to testing. The chip to be tested was placed in the apparatus.
  • a cross-head is lowered at the rate of 0.1 inch per minute (2.5 mm per minute) until it contacts the upper piece of the device. As the cross-head continues to travel downward, it causes adhesive failure in the chip.
  • the compressive shear strength of the chip is the shear stress required to cause adhesive failure.
  • the precision of this test is such that one standard deviation is typically 6% of the average result of six chips . Controls were also tested, and these used the same thicknesses of PVB but with no imbedded PET films. These laminates were also measured for haze and transmission in the visible region. The test results are tabulated below: Table 3
  • PRIMER x No PET present in laminate. 2 PETC4 The use of the polyallylamine primer on both sides of the PET films greatly improved the laminate shear strength over that seen with flame treated PET film and even over that seen in laminates made without any imbedded film.
  • Example 4 Imbedded film laminates with the structure given below were made using an autoclave cycle of 135C at 200 psi for 30 minutes with the use of vacuum bags:
  • PVB/SGP/film hybrid laminates The data show the poor adhesion between PVB and SGP where the CSS was only 372 psi and the shearing took place at the interface between the PVB and the SGP. Both the PETC4 and PRIMER films improved the CSS about equally. The shearing took place at the glass/SGP interface for the PRIMER laminates and at the PET/SGP for the PETC4 laminates.
  • PVB/fil laminates Using the imbedded PRIMER film apparently increases the CSS and using the flame treated PET film reduces the CSS relative to using no intermediate layer between the PVB.
  • the shearing took place at the SGP-to-glass interfaces.
  • Example 5 SENTRYGLASTM/SPALLSHIELDTM laminates were made using flame treated PET film and PRIMER films by coating each film on one side with polysiloxane abrasion resistant hardcoat followed by lamination to glass in an autoclave at 135°C for 30 minutes at a pressure of 17 atmospheres using vacuum bags.
  • a polysiloxane abrasion resistant coating (PARC) solution was made by the technique described in U.S.
  • the laminates were then immersed in boiling water for 6 hours followed by testing again for optical properties (ASTM D 1003-61), PARC adhesion (D 3359 - 87), micro- blistering, and PET-to-interlayer adhesion (peel testing). The results are tabulated below in Table 5.
  • G 90 mil annealed glass
  • PET flame treated PET film, 7.0 mils thick (PETC4)
  • PR* PET film primed on both sides with polyallylamine coating (PRIMER) .
  • Example 6 Two laminates were made with 6.5 mil PRIMER film: (A) structure ⁇ A" used 30 mil BUTACITETM PVB sheeting and the 6.5 mil primed PET, and (B) structure B" was made using 60 mil SENTRYGLASTM-PLUS ionoplast interlayer and the 6.5 mil primed PET. Both laminates were made with the GLASS /INTERLAYER/PET construction and a removable cover plate of 90 mil glass was used against the plastic side of the laminates to give it an optically flat surface. The laminates were vacuum bagged followed by heating in an autoclave at 135°C for 30 minutes at temperature and 200 psi pressure.
  • Example 7 The use of polyallylamine primed PET film in SP/SG laminates allows the use of SGP as the interlayer instead of PVB, and, as described above, it gives a harder plastic side to the laminates that is more resistant to dents and dings from rough handling. But it also gives a stiffer laminate post breakage, and so should perform well in the hurricane test from both the impact and pressure cycling aspects.
  • Two SGP based SP/SG laminates were tested for impact performance using a bull-nosed pendulum impactor that weighed 70.12 lbs. The nose is of steel and is hemispheric with a 3" diameter rounded head. The 12" X 12" laminates were securely fastened in a vertical steel frame with rubber gasketing.
  • Impact energy is determined by the height of the impactor above the center of the laminate at the release point. The impactor height was increased until it fully penetrated the laminate and this was the Height reported in the Table below, and the penetration energy (reported in the Table below) was calculated using this height and the weight of the impactor.
  • the two SGP—based laminates used 60 mil SENTRYGLASTM-PLUS interlayer. One used 7.0 mil thick CRONARTM 732C film that was flame treated, and the other one used 6.5 mil PRIMER film that was primed in-line with polyallylamine coating. The results are shown in Table 7.
  • Example 8 Polyallylamine primed PET film also makes possible hybrid SP/SG laminate structures wherein SGP and PVB can be used in the same laminate with the primed film acting as the adhesive layer attaching them strongly together.
  • the PET also adds its high strength and stiffness to the total structure as well.
  • Such a structure is included in the table used in Example 7 as Sample "GG" . This structure could not be penetrated below 400 ft-lbs, and was not penetrated in this test.

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KR20060131779A (ko) 2006-12-20
JP2007513813A (ja) 2007-05-31
CN1890092A (zh) 2007-01-03
US7189457B2 (en) 2007-03-13
EP1697128A1 (en) 2006-09-06

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