EP3589710A1 - High performance photocurable optically clear adhesive - Google Patents

High performance photocurable optically clear adhesive

Info

Publication number
EP3589710A1
EP3589710A1 EP18712743.6A EP18712743A EP3589710A1 EP 3589710 A1 EP3589710 A1 EP 3589710A1 EP 18712743 A EP18712743 A EP 18712743A EP 3589710 A1 EP3589710 A1 EP 3589710A1
Authority
EP
European Patent Office
Prior art keywords
optically clear
curable adhesive
meth
acrylate
polyurethane
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP18712743.6A
Other languages
German (de)
English (en)
French (fr)
Inventor
Lan Hong Liu
Jianhui Xia
Thomas P. Klun
David A. Kowitz
Audrey A. Sherman
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.)
3M Innovative Properties Co
Original Assignee
3M Innovative Properties 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 3M Innovative Properties Co filed Critical 3M Innovative Properties Co
Publication of EP3589710A1 publication Critical patent/EP3589710A1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
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    • 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
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    • 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
    • B32B17/10706—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 being photo-polymerized
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    • C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
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    • C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
    • C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
    • C08G18/757—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing at least two isocyanate or isothiocyanate groups linked to the cycloaliphatic ring by means of an aliphatic group
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    • C08G18/758—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing two or more cycloaliphatic rings
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    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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    • C08G18/81—Unsaturated isocyanates or isothiocyanates
    • C08G18/8108—Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group
    • C08G18/8116—Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group esters of acrylic or alkylacrylic acid having only one isocyanate or isothiocyanate group
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J129/00—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 at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal, or ketal radical; Adhesives based on hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Adhesives based on derivatives of such polymers
    • C09J129/14—Homopolymers or copolymers of acetals or ketals obtained by polymerisation of unsaturated acetals or ketals or by after-treatment of polymers of unsaturated alcohols
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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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
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
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Definitions

  • the present invention is generally related to optically clear adhesives.
  • the present invention is a photocurable optically clear adhesive.
  • PCOCAs photocurable optically clear adhesives
  • LOCAs liquid optically clear adhesives
  • liquid crystal module (LCM) bonding in which it is believed that a low shrinkage, low modulus material is necessary for optical performance and LCM bonding. Furthermore, it is also critical to ensure that the OCA does not have a deleterious effect on the LCM's appearance (e.g. mura effect, optical defects, etc.), has high adhesion, and is optically reliable under environmental conditions, such as exposure to a temperature of 85 °C or conditions of 65°C/ 90% RH for an extended period of time.
  • LCM liquid crystal module
  • the present invention is an optically clear, curable adhesive including a polyvinylbutyral, a polyurethane (meth)acrylate, and a photoinitiator.
  • the polyvinylbutyral has a dynamic viscosity of between about 9 and about 13 raPA s and a polyvinyl alcohol weight percent of less than about 18%.
  • the polyurethane (meth)acrylate includes the reaction product of a diol, at least one diisocyanate, and a hydroxyfunctional (meth)acrylate or an isocyanatofunctional (meth)acrylate.
  • the laminate When the optically clear, curable adhesive is placed between two transparent substrates and made into a laminate, the laminate has a haze of less than about 6%, a transmission of greater than about 88%, and an optical clarity of greater than about 98% when cured.
  • the optically clear, curable adhesive also has a peel adhesion of at least about 100 g/cm based on ASTM 3330 when cured.
  • the present invention is an optically clear laminate including a first substrate, a second substrate, and an optically clear, curable adhesive positioned between the first substrate and the second substrate.
  • the optically clear, curable adhesive includes a polyvinylbutyral, a polyurethane (meth)acrylate, and a photoinitiator.
  • the polyvinylbutyral has a dynamic viscosity of between about 9 and about 13 mPA s and a polyvinyl alcohol weight percent of less than about 18%.
  • the polyurethane (meth)acrylate includes the reaction product of a diol, at least one
  • optically clear, curable adhesive When the optically clear, curable adhesive is placed between two transparent substrates and made into a laminate, the laminate has a haze of less than about 6%), a transmission of greater than about 88% and an optical clarity of greater than about 98%) when cured.
  • the optically clear, curable adhesive also has a peel adhesion of at least about 100 g/cm based on ASTM 3330.
  • the present invention is a high performance, photocurable optically clear adhesive (PCOCA) construction.
  • the PCOCA is a curable, optically clear adhesive with superior optical clarity as well as superior adhesion and may be used, for example, in a display assembly for bonding a substrate to glass.
  • the PCOCA materials are prepared from blends of curable (meth)acrylic and polyurethane (or polyurea) based reactive oligomers.
  • the PCOCA of the present invention includes a polyvinylbutyral, a polyurethane (meth)acrylate and a photoinitiator.
  • the PCOCA includes between about 20% and about 80%, particularly between about 30% and about 60%, more particularly between about 32% and about 60%, and most particularly between about 40% and about 60% by weight polyvinylbutyral (excluding photoinitiator) and between about 20%) and about 80%, particularly between about 40% and about 70%, more particularly between about 40% and about 68%, and most particularly between about 40% and about 60%) by weight polyurethane (meth)acrylate (excluding photoinitiator).
  • the PCOCA includes between about 20% and about 80%, particularly between about 30% and about 60%, more particularly between about 32% and about 60%, and most particularly between about 40% and about 60% by weight polyvinylbutyral (excluding photoinitiator) and between about 20%) and about 80%, particularly between about 40% and about 70%, more particularly between about 40% and about 68%, and most particularly between about 40% and about 60%)
  • the weight percentages of the polyvinylbutyral and polyurethane are the weight percentages of the polyvinylbutyral and polyurethane
  • the polyvinylbutyral has a dynamic viscosity of between about 9 and about 13 mPA s (as measured according to DIN 53015, 10% solids in solution, in ethanol containing 5% water) with a polyvinyl alcohol weight percent of less than about 18%).
  • the polyvinylbutyral has a polyvinyl alcohol weight percent of between about 14% and about 18% and a polyvinyl acetate weight percent of between about 5%) and about 8%.
  • the polyvinylbutyral has a weight average molecular weight of between about 10,000 g/mol and about 15,000 g/mol.
  • An example of a suitable commercially available polyvinylbutyral includes, but is not limited to, Mowital B 14S, available from Kuraray America, Inc. located in Houston, TX.
  • Polyurethane (meth)acrylates are polyurethane polymers having one or more (meth)acrylate groups attached to the polyurethane polymer.
  • Polyurethanes are polymers that are useful in many applications, such as adhesives.
  • Polyurethanes may be prepared from starting materials that include isocyanato functional group-containing compounds, such as polyisocyanates (preferably diisocyanates) and compounds having a functional group reactive with the isocyanate groups, such as polyols and/or polyamines (preferably diols and/or diamines).
  • polyurethanes are alternating, block, star block, or segmented copolymers (or combinations thereof).
  • Polyurethanes may also contain other chemical moieties, such as alkyl, aryl, acrylate, ether, ester, and carbonate groups, and mixtures thereof.
  • the polyurethane (meth)acrylate has a weight average molecular weight of between about 2,700 g/mol and about 63,000 g/mol.
  • Polyurethane (meth)acrylates may have (meth)acrylate functionality at one or more chain ends and at other sites in the polymer chain.
  • (meth)acrylate functionality at one or more chain ends and at other sites in the polymer chain.
  • (meth)acrylate diol e.g., 2-glyceryl (meth)acrylate
  • polyurethane (meth)acrylate may be used to make a polyurethane (meth)acylate having acrylate groups that are at sites not near the polymer chain ends.
  • the polyurethane (meth)acrylate has (meth)acrylate functionality at the chain ends.
  • Polyurethane (meth)acrylates may contain other functionality (e.g., ether, ester, and/or carbonate functional groups) by selection of the starting materials used to make them.
  • poly(tetramethylene oxide) may be used to make a polyurethane (meth)acrylate that also comprises ether functional groups.
  • a particularly suitable polyurethane (meth)acrylate comprises urethane, (meth)acrylate, and ether functional groups.
  • Another particularly suitable polyurethane (meth)acrylate comprises urethane, (meth)acrylate, and ester functional groups.
  • polyurethane (meth)acrylates examples include, but are not limited to: CN978, CN981, and CN991 available from Sartomer Americas located in Exton, PA.
  • the polyurethane (meth)acrylate has a polydispersity of between about 1.3 and about 3.0.
  • the polydispersity index is used as a measure of the broadness of a molecular weight distribution of a polymer, and is defined by the ratio of the number average molecular weigh weight average molecular weight. The larger the polydispersity index, the broader the molecular weight distribution of the polymer.
  • the polyurethane (meth)acrylate of the present invention includes a polyurethane (meth)acrylate comprising the reaction product of a diol, at least one diisocyanate, and a hydroxyfunctional (meth)acrylate or an isocyanatofunctional (meth)acrylate.
  • (meth)acrylate is defined to be an ester of acrylic or methacrylic acid.
  • the diol(s) and diisocyanate(s) may be present in different ratios, depending at least in part on the molecular weights of the diol(s) and diisocyanate(s) and the desired molecular weight of the resulting polyurethane (meth)acrylate.
  • diols may be selected to provide flexibility and conformability to
  • polyurethane (meth)acrylates and to adhesives comprising polyurethane (meth)acrylates Diols may also be selected to provide compatibility of polyurethane (meth)acrylates with polyvinylbutyral or other components of an adhesive formulation. Without being bound by theory, compatibility between the polyvinylbutyral and the polyurethane (meth)acrylate materials is thought to be necessary to obtain the desired optical properties in the resulting adhesives.
  • Diols may also be selected for their ability to contribute properties desired in the resulting adhesive, such as adhesive properties and optical properties.
  • diols based on poly(tetramethylene oxide) and on polycaprolactone are suitable in the polyurethane (meth)acrylates used in the adhesive formulations of the invention, and diols based on poly(tetramethylene oxide) are particularly suitable in polyurethane
  • the diol may include lower molecular weight diols such as ethylene glycol, or butanediol.
  • the diol is selected from one of a poly(tetramethylene oxide) diol having a number average molecular weight (M n ) of about 1000 g/mol or less and a polycaprolactone diol having a number average of about 1000 g/mol or less.
  • M n number average molecular weight
  • An example of a suitable commercially available poly(tetramethylene oxide) diol having a molecular weight of about 1000 g/mol includes, but is not limited to, PolyTHF 1000 Poly ether, available from BASF Corp. located in Florham Park, NJ.
  • Diisocyanates may also be selected for their ability to provide properties desired in the polyurethane (meth)acrylate and in the resulting adhesives, such as adhesive properties and optical properties.
  • the isocyanates include aliphatic isocyanates.
  • Particularly suitable isocyanates include aliphatic diisocyanates.
  • an aliphatic isocyanate is one in which each of the one or more isocyanato group(s) is attached by a chemical bond to an aliphatic carbon atom.
  • an aliphatic isocyanate molecule may also contain an aromatic moiety that is not attached to any of the one or more isocyanato groups.
  • methylene diphenyl diisocyanate (MDI) and toluene diisocyanate (TDI) are not aliphatic isocyanates, but are considered to be aromatic isocyanates.
  • meta-tetramethylxylylene diisocyanate and para-tetramethylxylylene diisocyanate (m-TMXDI and p-TMXDI, respectively) are considered aliphatic isocyanates even though they contain an aromatic ring (see structures below).
  • isocyanates containing no aromatic moiety in their molecular structure such as isophorone diisocyanate (IPDI), are aliphatic isocyanates.
  • diisocyanates examples include, but are not limited to: 2,6-toluene diisocyanate (TDI), methylenedicyclohexylene-4,4'-diisocyanate (H12MDI), 3- isocyanatomethyl- 3,5,5-trimethylcyclohexyl isocyanate (IPDI), 1,6-diisocyanatohexane (HDI), tetramethyl- m-xylylene diisocyanate, a mixture of 2,2,4- and 2,4,4-Trimethyl-l,6-diisocyanatohexane (TMXDI), trans- 1,4-hydrogenated xylylene diisocyanates (H6XDI) and combinations thereof.
  • the diisocyanate is an aliphatic diisocyanate.
  • the polyurethane (meth)acrylate of the present invention may also include a hydroxyfunctional (meth)acrylate or an isocyanatofunctional (meth)acrylate.
  • Monofunctional molecules may also be used in the preparation of polyurethanes.
  • monofunctional molecules such as monofunctional alcohol- and isocyanate- containing molecules can be used to introduce functional groups at or near the
  • Suitable monofunctional alcohols include 2 -hydroxy ethyl acrylate (HEA) and 2-hydroxy ethyl methacrylate (HEMA).
  • HAA 2 -hydroxy ethyl acrylate
  • HEMA 2-hydroxy ethyl methacrylate
  • Another monofunctional alcohol providing more than one acrylate per alcohol group is exemplified by glycerol dimethacrylate, also known as bis(methacryloyloxy)propanol (mixture of 1 ,2- and 1,3-form).
  • Suitable monofunctional isocyanates include 2- isocyanatoethyl acrylate and 2-isocyanatoethyl methacrylate.
  • Another monofunctional isocyanate providing more than one acrylate per isocyanate group is exemplified by 1, 1- bis(acryloyloxymethyl)ethyl isocyanate, available from CBC America, Commack,NY. All of these compounds may be used to synthesize polyurethanes with (meth)acrylate end groups.
  • Suitable polyurethane (meth)acrylates are prepared by combining a
  • the monofunctional alcohol is selected from HEA, HEMA, and combinations thereof.
  • Other suitable polyurethanes are prepared by combining a monofunctional isocyanate and a difunctional isocyanate with a diol.
  • the monofunctional alcohol is selected from HEA, HEMA, and combinations thereof.
  • monofunctional isocyanate is selected from 2-isocyanatoethyl acrylate, 2-isocyanatoethyl methacrylate.
  • polyurethane (meth)acrylates are prepared by combining a monofunctional alcohol, as discussed above, with a diisocyanate.
  • a monofunctional alcohol suitable for reaction with a diisocyanate is caprolactone extended hydroxyethyl (meth)acrylate.
  • An example of a commercially suitable caprolactone extended hydroxyethyl (meth)acrylate includes, but is not limited to, SR495, available from Sartomer Americas located in Exton, PA.
  • a variety of methods may be used to synthesize polyurethane (meth)acrylates.
  • the starting materials may be combined by methods known in the art and in selected ratios to produce polyurethane (meth)acrylates with desired properties, such as a selected molecular weight.
  • One method known in the art is to combine a polyfunctional alcohol (preferably a diol) with a polyisocyanate (preferably a diisocyanate) to produce a polyurethane prepolymer.
  • a polyurethane prepolymer may have either alcohol or isocyanate functional groups on the molecular chain ends, depending on the selected ratio of polyalcohol to polyisocyanate.
  • the ratio of diisocyanate to diol is chosen to both provide the desired molecular weight and to produce either isocyanate or hydroxyl end groups at the ends of the polyurethane prepolymer.
  • a polyurethane prepolymer with isocyanate functional groups on the molecular chain ends can be reacted with a monoalcohol to produce a polyurethane in which the end groups are provided by the monoalcohol.
  • a polyurethane prepolymer with alcohol functional groups on the molecular chain ends can be reacted with a monoisocyanate to produce a polyurethane in which the end groups are provided by the monoisocyanate.
  • a polyurethane prepolymer is reacted with another molecule that introduces (meth)acrylate functionality.
  • the meth(acrylate) molecule is chosen to have functionality that is complementary to that of the polyurethane prepolymer that it is reacted with.
  • a (meth)acrylate molecule is chosen that also contains hydroxyl functionality (for example, HEA or HEMA).
  • a (meth)acrylate molecule is chosen that also contains an isocyanate group (for example, 2- isocyanatoethyl acrylate or 2-isocyanatoethyl methacrylate).
  • an isocyanate group for example, 2- isocyanatoethyl acrylate or 2-isocyanatoethyl methacrylate.
  • the polyisocyanate and the polyfunctional alcohol may be chosen to provide properties desired in the resulting urethane (meth)acrylate, such as thermal properties (e.g., glass transition temperature), optical properties (e.g., transmission, haze, and clarity), solubility in selected solvents, and compatibility with other selected polymers (e.g., poly (vinyl butyral) (PVB)).
  • thermal properties e.g., glass transition temperature
  • optical properties e.g., transmission, haze, and clarity
  • solubility in selected solvents e.g., poly (vinyl butyral) (PVB)
  • Polyurethane (meth)acrylates may have (meth)acrylate functionality at one or more chain ends and at other sites in the polymer chain.
  • (meth)acrylate functionality at one or more chain ends and at other sites in the polymer chain.
  • (meth)acrylate diol e.g., 2-glyceryl (meth)acrylate
  • a polyurethane (meth)acrylate having (meth)acrylate groups that are at sites not near the polymer chain ends.
  • a polyurethane (meth)acrylate has (meth)acrylate functionality at the chain ends.
  • Polyurethane (meth)acrylates may contain other functionality (e.g., ether, ester, and/or carbonate functional groups) by selection of the starting materials used to make them.
  • poly(tetramethylene oxide) may be used to make a polyurethane (meth)acrylate that also comprises ether functional groups.
  • a particularly suitable polyurethane (meth)acrylate comprises urethane, (meth)acrylate, and ether functional groups.
  • Another particularly suitable polyurethane (meth)acrylate comprises urethane, (meth)acrylate, and ester functional groups.
  • a photoinitiator is used to cure the PCOCA.
  • the initiator or initiators are activated by exposure to light of the appropriate wavelength and intensity. Often UV light is used.
  • suitable commercially available photoinitators include, but are not limited to: Darocur 4265 and Irgacure 184, both available from BASF Corp. located in Florham Park, NJ.
  • Other materials can be added to the precursor mixture for special purposes, including, for example: heat stabilizers, adhesion promoters, crosslinking agents, surface modifying agents, ultraviolet light stabilizers, antioxidants, antistatic agents, thickeners, fillers, pigments, colorants, dyes, thixotropic agents, processing aids, nanoparticles, fibers and combinations thereof.
  • the high performance, photocurable optically clear adhesive can be positioned between a first substrate and a second substrate to form a laminate.
  • the laminate includes the first substrate having at least one major surface, the second substrate having at least one major surface and the PCOCA positioned adjacent the major surfaces of the first and second substrates.
  • at least one of the first and second substrates is optically clear and may include, for example, an optical film or optically clear substrate.
  • the laminate including the PCOCA can be used in a display assembly.
  • the display assembly can further include another substrate (e.g., permanently or temporarily attached to the PCOCA), another adhesive layer, or a combination thereof.
  • adjacent can be used to refer to two layers that are in direct contact or that are separated by one or more thin layers, such as primer or hard coating. Often, adjacent layers are in direct contact.
  • laminates are provided that include the PCOCA positioned between two substrates, wherein at least one of the substrates is an optical film. Optical films intentionally enhance, manipulate, control, maintain, transmit, reflect, refract, absorb, retard, or otherwise alter light that impinges upon a surface of the film.
  • Films included in the laminates include classes of material that have optical functions, such as polarizers, interference polarizers, reflective polarizers, diffusers, colored optical films, mirrors, louvered optical film, light control films, transparent sheets, brightness enhancement film, anti-glare, and anti -reflective films, and the like. Films for the provided laminates can also include retarder plates such as quarter-wave and half-wave phase retardation optical elements. Other optically clear films include anti-splinter films and electromagnetic interference filters.
  • the resulting laminates can be optical elements or can be used to prepare optical elements.
  • optical element refers to an article that has an optical effect or optical application.
  • the optical elements can be used, for example, in electronic displays, architectural applications, transportation applications, projection applications, photonics applications, and graphics applications. Suitable optical elements include, but are not limited to, glazing (e.g., windows and windshields), screens or displays, cathode ray tubes, and reflectors.
  • Exemplary optically clear substrates include, but are not limited to: a display panel, such as liquid crystal display, an OLED display, a touch panel, electrowetting display or a cathode ray tube, a window or glazing, an optical component such as a reflector, polarizer, diffraction grating, mirror, or cover lens, another film such as a decorative film or another optical film.
  • a display panel such as liquid crystal display, an OLED display, a touch panel, electrowetting display or a cathode ray tube, a window or glazing
  • an optical component such as a reflector, polarizer, diffraction grating, mirror, or cover lens
  • another film such as a decorative film or another optical film.
  • optically clear substrates include glass and polymeric substrates including those that contain polycarbonates, polyesters (e.g., polyethylene terephthalates and polyethylene naphthalates), polyurethanes, poly(meth)acrylates (e.g., polymethyl methacrylates), polyvinyl alcohols, polyolefins such as polyethylenes, polypropylenes, and cellulose triacetates.
  • cover lenses can be made of glass, polymethyl methacrylates, or polycarbonate.
  • either substrate can be a release liner.
  • Any suitable release liner can be used.
  • Exemplary release liners include those prepared from paper (e.g., Kraft paper) or polymeric material (e.g., polyolefins such as polyethylene or polypropylene, ethylene vinyl acetate, polyurethanes, polyesters such as polyethylene terephthalate, and the like). At least some release liners are coated with a layer of a release agent such as a silicone-containing material or a fluorocarbon-containing material.
  • Exemplary release liners include, but are not limited to, liners commercially available from CP Film
  • the release liner can be removed to adhere the PCOCA to another substrate (i.e., removal of the release liner exposes a surface of an adhesive layer that subsequently can be bonded to another substrate surface).
  • removal of the release liner exposes a surface of an adhesive layer that subsequently can be bonded to another substrate surface.
  • the PCOCA is permanently bonded to this other substrate, although in some cases the adhesion may be limited to allow for reworking of the display.
  • the high performance, photocurable optically clear adhesive of the present invention maintains optical clarity, bond strength, and resistance to delamination over the lifetime of the article in which it is used.
  • optically clear refers to a material that has a haze of less than about 6%, particularly less than about 4% and more particularly less than about 2%; a luminous transmission of greater than about 88%, particularly greater than about 89%, and more particularly greater than about 90%; and an optical clarity of greater than about 98%, particularly greater than about 99%, and more particularly greater than about 99.5% when cured.
  • the clarity, haze, and transmission are measured on a construction in which the adhesive is held between two optical films, such as poly(ethylene terephthalate) (PET).
  • Both the haze and the luminous transmission can be determined using, for example, ASTM-D 1003-92.
  • the optical measurements of transmission, haze, and optical clarity can be made using, for example, a BYK Gardner haze-gard plus 4725 instrument (Geretsried, Germany).
  • the BYK instrument uses an illuminant "C" source and measures all the light over that spectral range to calculate a transmission value.
  • Haze is the percentage of transmitted light that deviates from the incident beam by more than 2.5°.
  • Optical clarity is evaluated at angles of less than 2.5°.
  • the PCOCA is visually free of bubbles.
  • the high performance, photocurable optically clear adhesive of the present invention also has a peel adhesion of at least about 100 g/cm, particularly at least about 150 g/cm and more particularly at least about 200 g/cm based on ASTM 3330 when cured. If the peel adhesion of the PCOCA is too low, the adhesive will fail and may cause an article including it to come apart (delaminate). An adhesive may fail in a number of ways. The adhesive fails if adhesive residue remains on either one or both substrates positioned adjacent either side of the adhesive.
  • the PCOCAs of the present invention offer several advantages over polyvinylbutyrals when used to make devices.
  • the PCOCAs are curable, so they can have markedly different properties before and after cure.
  • Polyvinylbutyrals do not change properties in this manner, and therefore behave more like hot melt adhesives.
  • the PCOCAs resist flow.
  • Polyvinylbutyrals are known to flow at elevated temperatures, such as those an adhesive could be exposed to during the manufacture of a device.
  • the properties of PCOCAs can be tuned to meet product needs by the choice of components and by varying the ratio of components. This provides advantages in the sourcing, development, and application of PCOCAs for new products over both the polyvinylbutyrals by themselves and over many existing optically clear adhesives.
  • the laminates of the present invention have at least one of the following properties: the PCOCA has optical transmissivity over a useful lifetime of the article, the PCOCA can maintain a sufficient bond strength between layers of the article, the PCOCA can resist or avoid delamination, and the PCOCA can resist bubbling of the adhesive layer over a useful lifetime.
  • the laminate is optically clear, having a haze of less than about 6%, particularly less than about 4% and more particularly less than about 2%; a luminous transmission of greater than about 88%, particularly greater than about 89%, and more particularly greater than about 90%; and an optical clarity of greater than about 98%, particularly greater than about 99%, and more particularly greater than about 99.5% when cured.
  • the molecular weight distribution of each polyurethane (meth)acrylate was characterized using conventional gel permeation chromatography (GPC).
  • GPC gel permeation chromatography
  • the GPC instrumentation which was obtained from Waters Corporation (Milford, MA, USA), included a high pressure liquid chromatography pump (Model 1515HPLC), an auto-sampler (Model 717), a UV detector (Model 2487), and a refractive index detector (Model 2410).
  • the chromatograph was equipped with two 5 micron PLgel MIXED-D columns, available from Varian Inc. (Palo Alto, CA, USA).
  • Samples of polymeric solutions were prepared by diluting polymer solution or dissolving dried polymer materials in tetrahydrofuran (THF) at a concentration of 0.5 percent (weight/volume) and filtering the THF solution through a 0.2 micron polytetrafluoroethylene filter that is available from VWR International (West Chester, PA, USA).
  • THF tetrahydrofuran
  • the resulting samples were injected into the GPC and eluted at a rate of 1 milliliter per minute through the columns maintained at 35°C.
  • the system was calibrated with polystyrene standards using a linear least squares fit analysis to establish a calibration curve.
  • the weight average molecular weight (M w ) and the polydispersity index weight average molecular weight divided by number average molecular weight) were calculated for each sample against this standard calibration curve.
  • the molecular weight distributions are listed in Table 2.
  • the optical measurements of transmission, haze, and optical clarity were made using a BYK Gardner Haze-Gard Plus 4725 instrument (Geretsried, Germany).
  • the BYK instrument uses an illuminant "C" source and measures all the light over that spectral range to calculate a transmission value.
  • Haze is the percentage of transmitted light that deviates from the incident beam by more than 2.5°.
  • Optical clarity is evaluated at angles of less than 2.5°. Values are reported as percent transmission (%T), percent haze (%H), and percent clarity (%C) in Table 4.
  • a sample was considered acceptable if it had a percent transmission of at least 88%, a percent haze of no more than 6%, and a percent clarity at least 98% after rounding.
  • the peel adhesion test was based on ASTM D 3330. Room temperature peels were done using an IMASS peel tester, available from EVIASS, Inc. (Accord, Massachusetts) using a 5 kg load cell, a 4 second delay, a 20 second test time and a 30.48 cm/min peel rate. Three replicates were tested and the averages are reported in grams per centimeter (g/cm). Peel adhesion results are listed in Table 3. A sample was considered acceptable if it had a peel adhesion of at least about 100 g/cm.
  • a roll of 125 micron thick polyethylene phthalate (PET) film was mounted on the unwind-roll of a roll-to-roll vacuum processing chamber, the film wrapped around a drum electrode, and then secured to the take-up roll on the opposite side of the drum electrode.
  • the un-wind and take-up tensions were maintained at 3 pounds (13.3 N).
  • the chamber door was closed and the chamber pumped down to a base pressure of about 5xl0 "4 Torr.
  • Hexamethyldisiloxane (HMDSO) was introduced at a flow rate of 20 standard cubic centimeters per minute (seem), and oxygen was provided at a flow rate of 500 seem.
  • Plasma was turned on at a power of 6000 watts by applying radio frequency power to the drum and the drum rotation initiated so that the film was transported at a speed of 10 feet per minute. The pressure during the exposure was around 8-10 mTorr.
  • Adhesive solutions as provided in Table 3 were coated on the primed surface of plasma primed PET using a knife coater with a 20 mil gap. The coated samples were dried at 70°C for ten minutes. The samples were removed from the oven and an SKC T50 tight release liner was applied by hand. The samples were then cut to 1.3 cm width by 13 cm length. Float glass panes of dimensions 6.35 cm by 17.78 cm were heated to 90°C in an oven before lamination. The release liner was then removed from the samples and they were laminated to the air side (non-tin) of float glass using a hand roller.
  • the laminated glass slides were then placed in an oven at 90°C for 5 minutes before laminating again, using release liner film as an interface between the roller and the samples, to prevent contaminating the roller in case the adhesive oozed.
  • the coating was then cured using a Light-Hammer 6 UV curing system (Fusion UV-Sy stems Inc., Gaithersburg, MD) equipped with a D bulb operating under nitrogen atmosphere at 100% lamp power at a line speed of 20 feet/min using 4 passes.
  • a three liter three-necked round-bottomed reaction flask equipped with an overhead stirrer was charged with 99.31 g (0.8935 equivalents (eq.), 1 1 1.15 eq Wt) IPDI, 480 g MEK, 386.42 g (0.7818eq, 492.27 eq Wt) PolyTHF 1000 (dried overnight at 80°C at a pressure of less than 20 mmHg) and 0.25 g (500 ppm with respect to total solids) DBTDL.
  • the flask was placed in an oil bath, fitted with a condenser and a temperature probe, placed under dry air, and allowed to stir.
  • the reaction temperature was 28°C, at 5 min it was 29.9°C, at 13 min it was 31.7°C, at 23 min it was 47.9°C, and at 31 min it was 53°C.
  • the oil bath was heated to bring the internal temperature to 60°C.
  • an FTIR of a reaction aliquot showed a small isocyanate peak at 2265 cm -1 .
  • 14.23 g (0.1229 eq, 10% stoichiometric excess) HEA was added and rinsed in with 20 g MEK to bring the reaction to 50% solids.
  • FTIR of a reaction aliquot showed no isocyanate peak at 2265cm "1 .
  • the reaction was then adjusted to 35% solids with 428.57 g MEK.
  • the structures of these polyurethane acrylates are believed to be linear polymers formed by reaction of the diols and diisocyanates to form urethanes, and these linear polymers are capped on each end with hydroxy ethyl acrylate (two equivalents required, but 10%) stoichiometric excess was used to ensure complete conversion).
  • the stoichiometric amount of HEA would be 0.1229/1.1 or 0.1 1 17 eq.
  • the number of equivalents of IPDI was (0.8935/0.1117)*2, or 16 equivalents, and the number of equivalents of the PTMO diol was (0.7818/0.1117)*2, or 14 equivalents.
  • polyurethane acrylate C was used to synthesize the remaining polyurethane acrylates (PUA), using the starting material weights in grams as indicated in Table 2.
  • the reactions were run in either a flask or ajar (with magnetic stirring) at 50% solids with 500 ppm DBTDL. All polyols were dried under vacuum ( ⁇ 10 torr) at 80°C for at least two hours before use. In some cases, some reactions were diluted to 35% or 33%) solids, and in some cases the reaction was left at 50% solids (indicated in Table 2) and used in further formulations.
  • a 500 mL three-necked round-bottomed reaction flask equipped with an overhead stirrer is charged with 27.25 g (0.245 equivalents (eq.)) isophorone diisocyanate (IPDI) and 20 g methyl ethyl ketone (MEK), placed in an oil bath, fitted with a condenser, placed under dry air, and heated to 60°C.
  • a pressure equalizing addition funnel is charged with 140.1 g (0.280 eq.) of 1,000 g/mol poly(tetramethylene oxide) (PTMO, dried under vacuum ( ⁇ 10 torr) at 80°C for at least two hours before use) and 80 g MEK and attached to the reaction flask.
  • PTMO poly(tetramethylene oxide)
  • reaction flask To the reaction flask is added 800 microliters of a 10% solution of DBTDL in MEK. The contents of the addition funnel are then added over 30 minutes to the reaction flask, and at the end of that time, the addition funnel is rinsed with 5 g MEK, and 30 g more MEK is added directly to the reaction mixture. At 2 hours into the reaction, the reaction mixture shows a small isocyanate peak at 2265 cm-1 by FTIR. In one portion, 4.94 g (0.0350 eq.) 2- isocyanatoethyl acrylate (HEA) in 8.02 g MEK is added to the reaction from a jar. The jar is rinsed with 5 g and then 0.5 g MEK and the rinses are added to the reaction.
  • HOA 2- isocyanatoethyl acrylate
  • Table 3 provides the composition of the solutions coated for each example.
  • the abbreviations in the column labelled PVB are provided in Table 1.
  • the polyurethane acrylate (PUA) is either described in Table 2 and added at the wt% solids indicated in Table 2, or, for the commercially available polyurethane acrylates (CN964, CN978, CN981, CN991, CN9002, and CN9004), added at 50% solids solutions in MEK, unless otherwise noted.
  • the photoinitiator solution is Irgacure 819 at 10% solids in MEK.
  • Example 1 contains 11.88 g of 25 wt% solution of Mowital B 14 S, corresponding to 2.97 g solids. It also contains 5.94 g of 50 wt% solution of PUA B, corresponding to 2.97 g solids. The total amount of solids (excluding Irgacure 819) was thus 2.97 g + 2.97 g, or 5.94 g. All solutions were adjusted to 30 wt% solids in MEK, unless otherwise noted, and the g of MEK added or removed (positive or negative value, respectively) to reach 30 wt% solids is given.
  • the total solids for Example 1 was 5.94 g + 0.059 g, or 6.00 g.
  • Test specimens were prepared using the adhesive solutions provided in Table 3 by coating each adhesive solution on the primed side of 2 mil plasma primed PET film using a knife coater with a 25 mil gap.
  • the coated PET film was air dried for about 10 minutes before being placed in a 65°C oven for 10 minutes.
  • the sample was then taped onto a stainless steel plate pre-heated to 90°C for about 90 sec and a second piece of 2 mil SSP PET film was then laminated on its primed side to the coating.
  • the PET-coating-PET laminate was then cured using a Light-Hammer 6 UV curing system (Fusion UV Systems Inc., Gaithersburg, MD) equipped with a D bulb operating under nitrogen atmosphere at 100% lamp power at a line speed of 20 feet/min using 1 pass.
  • a Light-Hammer 6 UV curing system Fusion UV Systems Inc., Gaithersburg, MD
  • Example 14 B 14 S 30 7.92 0 7.13 0.59 40:60

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  • Chemical Kinetics & Catalysis (AREA)
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  • Polymers & Plastics (AREA)
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  • Polyurethanes Or Polyureas (AREA)
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