WO2003078536A2 - Pressure sensitive adhesive for use in vibration/sound-damping - Google Patents

Pressure sensitive adhesive for use in vibration/sound-damping Download PDF

Info

Publication number
WO2003078536A2
WO2003078536A2 PCT/US2003/006709 US0306709W WO03078536A2 WO 2003078536 A2 WO2003078536 A2 WO 2003078536A2 US 0306709 W US0306709 W US 0306709W WO 03078536 A2 WO03078536 A2 WO 03078536A2
Authority
WO
WIPO (PCT)
Prior art keywords
composition
meth
acrylate
copolymer
vinyl
Prior art date
Application number
PCT/US2003/006709
Other languages
French (fr)
Other versions
WO2003078536A3 (en
Inventor
Wilson Z. Xia
Deepak Hariharan
David A. Krupa
Original Assignee
Adhesives Research, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Adhesives Research, Inc. filed Critical Adhesives Research, Inc.
Priority to AU2003216522A priority Critical patent/AU2003216522A1/en
Publication of WO2003078536A2 publication Critical patent/WO2003078536A2/en
Publication of WO2003078536A3 publication Critical patent/WO2003078536A3/en

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00Adhesives 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04Homopolymers or copolymers of esters
    • C09J133/06Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/062Copolymers with monomers not covered by C09J133/06
    • C09J133/066Copolymers with monomers not covered by C09J133/06 containing -OH groups
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00Adhesives 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04Homopolymers or copolymers of esters
    • C09J133/06Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/062Copolymers with monomers not covered by C09J133/06
    • C09J133/068Copolymers with monomers not covered by C09J133/06 containing glycidyl groups
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2666/00Composition 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
    • C08L2666/02Organic macromolecular compounds, natural resins, waxes or and bituminous materials
    • C08L2666/04Macromolecular compounds according to groups C08L7/00 - C08L49/00, or C08L55/00 - C08L57/00; Derivatives thereof
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04Homopolymers or copolymers of esters
    • C08L33/06Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
    • C08L33/062Copolymers with monomers not covered by C08L33/06
    • C08L33/066Copolymers with monomers not covered by C08L33/06 containing -OH groups
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04Homopolymers or copolymers of esters
    • C08L33/06Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
    • C08L33/062Copolymers with monomers not covered by C08L33/06
    • C08L33/068Copolymers with monomers not covered by C08L33/06 containing glycidyl groups

Definitions

  • the present invention is directed to an ultra-clean pressure sensitive
  • Computer systems generally include
  • Such disk drives for storage of information.
  • Such disk drives for storage of information.
  • drives are generally in the form of a sealed head-disk assembly chamber which
  • composition that exhibits pressure sensitive adhesive properties.
  • alkyl (meth)acrylate monomer having a Tg > 20 °C, optionally a C 1-3 o
  • Tg of said copolymer (B) is less than about -20 °C
  • copolymers (A) and (B) are present in said composition in
  • a weight ratio ranging from about 0: 100 to about 40:60.
  • the adhesive composition of the present invention is comprised of low
  • Tg copolymer (B) either alone or together high Tg polymer (A) and which may
  • composition of the present invention enables a number of benefits
  • the composition enables highly desirable
  • composition of the invention enables values above 0.6 (at 1Hz), 1.2 (at 100
  • DMA Dynamic Mechanical Analysis
  • composition in the electronics industry as the composition may be tailored to be ultra-clean
  • composition by avoiding the presence of acid or polar components; i.e., the composition will
  • VOC's volatile organic compounds
  • the adhesive operate as miniature "speed bumps" when they condense on the
  • composition of the present invention also, due to its crosslinkable
  • composition of the present invention can be fine tuned to exhibit a
  • composition of the present invention may be used to damp
  • vibrations or sound in an article by providing a film or layer of a vibration or
  • the film or layer is capable of attenuating vibration or sound in at least one
  • the composition may be coated on a surface
  • the high Tg copolymer (A) used in the composition of the present invention is the high Tg copolymer (A) used in the composition of the present invention.
  • invention is comprised of the polymerization reaction product of an alkyl
  • epoxy-containing monomer each as defined below.
  • the monomers are
  • the alkyl (meth)acrylate monomer having a Tg > 20 °C. may be
  • exemplary (meth)acrylic acid ester of a non-tertiary alcohol wherein the alcohol portion has from 4 to 18 carbon atoms.
  • (meth)acrylate monomers include but are not limited to esters of (meth)acrylic
  • non-tertiary alcohols such as 1-butanol, 1-pentanol, 2-pentanol, 3-
  • At least 12 carbon atoms include but are not limited to lauryl acrylate (C 12 ),
  • the at least one nitrogen-containing polar monomer may be selected
  • Such monomers include, for
  • N-mono-substituted acrylamides such as a
  • N,N-disubstituted acrylamides such as N,N-dimethylacrylamide, N,N-
  • diethylacrylamide N-ethyl-N-aminoethylacrylamide, N-ethyl-N-
  • Exemplary nitrogen-containing monomers may also include but are not
  • N- vinyl lactam monomers such as N-vinyl-2-pyrrolidone, 5-methyl- N-vinyl-2-pyrrolidone, 5-ethyl-N-vinyl-2- ⁇ yrrolidone, 3 ,3-dimethyl-N-vinyl-2-
  • valerolactam N-vinyl-2-caprolactam; N-vinyl-2-piperidone; and N,N-
  • allyl derivatives thereof are also suitable for use in the present invention.
  • lactams may also be substituted in the lactam ring by one or more lower
  • alkyl groups having from 1 to 4 carbon atoms, with methyl; ethyl, or propyl
  • the polymerizable epoxy-containing monomer may be selected from a
  • polymerizable monomers include but are not limited to glycidyl esters of an
  • ⁇ , ⁇ -ethylenically unsaturated carboxylic acid such as (meth)acrylic or
  • the alkyl (meth)acrylate monomer is present in the copolymerizable
  • the polymerizable C 1-3 o (meth)acrylate monomer is present in the mixture in an
  • the nitrogen-containing polar monomer is present in the mixture in an amount ranging from about 0 to 50 percent by weight, the nitrogen-containing polar monomer is present in the mixture in an amount ranging from about 0 to
  • the epoxy-containing monomer is preferably present in an amount
  • vinyl acetate may be incorporated into the copolymer with advantage.
  • copolymer will still have a Tg greater than 50 °C.
  • the alkyl (meth)methacrylate monomer is present together with the
  • Copolymer (A) does not
  • Copolymer (B) a copolymer comprised of the polymerization reaction
  • hydroxy(C 1-5 )alkyl(meth)acrylate monomers include but are
  • the preferred monomer is 2-ethylhexylacrylate.
  • the vinyl acetate or. vinyl ether component is present in copolymer (B)
  • (C 1 . 5 )alkyl(meth)acrylate component is present in an amount ranging from
  • containing monomer is present in an amount ranging from about 0 to about 5
  • Copolymers (A) and (B) are present in said composition in a weight
  • ratio ranging from about 0:100 to about 60:40, and preferably in a weight ratio
  • copolymers (A) and (B) may be
  • the final blend may have two separate Tg i values, or a single Tg value.
  • Copolymers (A) and (B) of the present invention can be prepared by any one of the following copolymers (A) and (B) of the present invention.
  • reaction technique such as free radical initiation techniques in the
  • solvents include but are not limited to ethyl
  • polymerization may typically range from about 40% to 60%.
  • radical initiators include but are not limited to peresters, acyl peroxides and
  • the free radical initiator is generally
  • reaction mixture present in an amount ranging from 0.01 to 10 % by wt.
  • Typical polymerization temperatures range from 20 °C. to 150 °C. for
  • the resulting polymer will preferably exhibit a molecular weight in the
  • U.S. Patent No. 5,723,191 discloses a tackified dual cure pressure
  • heterocyclic monomers and unsaturated ester monomer and a glycidyl
  • adhesive copolymer comprised of a N- vinyl lactam monomer, a glycidyl
  • thermosetting powder comprised
  • composition comprised of a glycidyl monomer, a lower alkyl acrylate and a
  • U.S. Patent No. 5,827,609 discloses a multilayer pressure sensitive adhesive construction where each layer exhibits a different glass transition
  • Any conventional solvent/diluent may be admixed with the copolymer
  • copolymers (A) and (B) at a sufficiently low viscosity.
  • solvents/diluents include but are not limited to xylene, toluene, butylacetate,
  • the resulting blend may be coated onto a backing material by any method.
  • the blend may be any suitable extrusion coating, etc. by use of conventional extrusion devices.
  • the blend may be any suitable extrusion devices.
  • the blend may be any suitable extrusion devices.
  • a solvent typically having a solids content of about 30
  • evaporation will occur at a temperature in the range of from about
  • the coated composition will have a thickness within the range of about 0.5 mil to about 50
  • Exemplary backing materials include but are not limited to flexible and
  • Such materials include creped paper, kraft paper,
  • polyamide polyimide, poly(ethylene terephthalate), polycarbonate, and
  • the adhesive may be applied to one or both of the aforementioned
  • adhesives may be combined in discrete layers with or without benefit of a
  • the adhesive may be applied between two
  • composition to modify the properties or characteristics thereof A variety of ingredients to modify the properties or characteristics thereof.
  • fillers may be incorporated into the polymer blend to provide desired physical
  • metallic flake filler such as stainless steel flake
  • having a particle size of 25-75 microns and aspect ratios of 31-94 may be incorporated into the composition in an amount of up to about 60 percent by
  • a high Tg such as polymethylmethacrylate may be added to produce a
  • crosslinking compounds (such as blocked polyamines) may also be used.
  • a high Tg acrylic polymer (comprised of 40%» by wt. t-butyl
  • transition temperature (Tg) of about 60°C (measured by DSC) and a second
  • Tg glass transition temperature
  • Such films were colaminated to yield a thickness greater than 0.6 mm for
  • DMA Dynamic Mechanical Analysis
  • An adhesive blend comprised of 55.45 parts of a high Tg acrylic
  • polymer (synthesized from 40% by wt. t-butyl methacrylate, 10% by wt. butyl
  • glycidyl methacrylate was prepared in the mixed solvent of ethyl acetate and
  • a 5-mil pressure sensitive adhesive film was generated by coating the blend on polyester film and subsequently removing the solvent using the
  • leachable ions are within the general acceptance criteria for Hard Disk Drive
  • a high Tg acrylic polymer was synthesized in ethyl acetate solvent

Abstract

A pressure sensitive adhesive addressing the problem of low volatility and non-corrosivity (i.e. ultra-clean) employed in vibration or sound damping of an article comprises from 0-60 % by weight of (A) a copolymer with a Tg of greater than about -2 degrees C polymerized from (1) an alkyl (meth)acrylate having a Tg of less than 20 degrees C and, optionally, an alkyl (meth)acrylate, N-containing monomer and/or epoxy-containing monomer; and from 40-100 % by weight of (B) a copolymer with a Tg of less than about -20 degrees C polymerized from a C2-C12 alkyl (meth)acrylate, a hydroxy(C1-C5)alkyl (meth)acrylate and, optionally, vinyl acetate or vinyl ether and/or epoxy-containing monomer.

Description

"Pressure Sensitive Adhesive For Use in Nibration/Sound-Damping"
BACKGROUND OF THE PRESENT INVENTION
The present invention is directed to an ultra-clean pressure sensitive
adhesive composition for use in vibration/sound-damping.
A quiet operating environment is often highly desirable in the high
performance computer and PC gaming systems. Computer systems generally
include at least one or more disk drives for storage of information. Such disk
drives are generally in the form of a sealed head-disk assembly chamber which
includes one or more disks stacked on a spindle motor hub. The acoustic noise
of a disk drive arises from the spindle motor and disks ("Idle Acoustics") and
from the moving actuator that supports the read/write heads ("Seek
Acoustics"). On the other hand, during operation of the disk drives, vibration
at various frequencies also occurs as a result of the mechanical resonance of the
various components of the sealed head-disk assembly. It is thus desirable to.
provide means to damp vibration/sound resulting from operation of such
devices.
The problem of vibration/sound-damping is not, however, restricted to
computer systems. Such problems also exist in the automobile industry as
well as conventional appliances, as well as any other application requiring the
use of motors or related vibration or sound-inducing mechanisms.
Many attempts have been made to address this problem. See, for
example, U.S. Patent Nos. 4,942,187 (vibration-damping rubber composition of
hexene-1 type polymer and Si-containing graft copolymer and inorganic reinforcing agent); 5,279,896 (mechanical design for disk drive vibration and
noise damping); 5,464,659 (vibration damping material comprised of acrylic
monomers, silicone adhesive, and optional crosslinker); 5,781,373 (soft metal
substrate for disk drive noise reduction); 5,858,521 (vibration damping material
of a laminate of a viscoelastic layer and a hardenable pressure sensitive
adhesive layer); 5,939,179 (vibration damping material comprised of one
surface of a rigid body and a polymer layer of synthetic rubber); and 6,216,817
(preparation of damping coating by photopolymerization); U.S. published
patent application No. 20010044023 (vibration attenuating article having a
non-tacky film covering substantially all of the article); and EP 390207
(vibration damping material comprised of blend of fluorine-containing polymer
and acrylic polymer). Such attempts have not always been successful. For
example, in the computer industry, any material used in connection with the
computer hardware must be low-volatile and non-corrosive in nature (i.e.,
ultra-clean). Conventional adhesives have not generally satisfied this
requirement. The adhesive material which is employed must also provide
vibration/sound-damping over a wide frequency range, possess both cold flow
and heat resistance, and provide high adhesion and good strippability.
OBJECTS AND SUMMARY OF THE PRESENT INVENTION
It is accordingly an object of the present invention to provide a pressure
sensitive adhesive composition that may be used in vibration/sound damping
applications. It is also an object of the present invention to provide an ultra-clean
composition that exhibits pressure sensitive adhesive properties.
In accordance with the present invention , there is provided a pressure
sensitive adhesive comprised of the following:
(A) a copolymer comprised of the polymerization reaction product of an
alkyl (meth)acrylate monomer having a Tg > 20 °C, optionally a C1-3o
(meth)acrylate monomer, optionally a nitrogen-containing polar monomer, and
optionally a polymerizable epoxy-containing monomer, said monomers being
present in an amount such that the Tg of said copolymer (A) is greater than
about -2 °C; and
(B) a copolymer comprised of the polymerization reaction product of an
optional vinyl acetate or vinyl ether component, (C2-12) alkyl (meth)acrylate,
hydroxy(C1-5)alkyl(meth)acrylate, and optionally a polymerizable epoxy-
containing monomer, said monomers being present in an amount such that the
Tg of said copolymer (B) is less than about -20 °C, and
wherein said copolymers (A) and (B) are present in said composition in
a weight ratio ranging from about 0: 100 to about 40:60.
There is also provided a method of damping vibrations or sound in an
article comprising providing a film or layer of a vibration or sound damping
material to the article such that said film or layer is capable of attenuating said
vibration or sound in at least one vibrational or sound mode, the film or layer
being comprised of the above composition. DETAILED DESCRIPTION OF THE PRESENT INVENTION
The adhesive composition of the present invention is comprised of low
Tg copolymer (B) either alone or together high Tg polymer (A) and which may
be used with particular advantage in vibration/sound-damping.
The composition of the present invention enables a number of benefits
to be achieved. For instance, the composition enables highly desirable
damping and absorption characteristics to be achieved over a wide freguency
range (1Hz to 10 kHz). The tan delta of the composition (measured by
Dynamic Mechanical Analysis) is an indication of energy loss and the
composition of the invention enables values above 0.6 (at 1Hz), 1.2 (at 100
Hz), 2.1 (at 1kHz) and 3.0 (at 10kHz) to be achieved (thus confirming the
ability of the composition to provide vibration/sound-damping).
Dynamic Mechanical Analysis (DMA) provides a useful tool to study
the dynamic properties of a material and is often used to characterize the sound
or vibration damping performance of polymers, particularly viscoelastic
polymers. The tan delta of the material, as defined by the ratio of Loss
Modulus (G) to Storage Modulus (G'), is a valuable indicator of the material's
relative damping ability. Any peak in tan delta (particularly apparent in
temperature profile studies) corresponds to a region where the material
properties are changing rapidly; i.e., the material is undergoing a transition. In
frequency dependent studies, a peak in tan delta indicates that the material
dissipates the incident sound or vibration energy and converts to heat very well at that frequency. High values of tan delta over a wide range of frequency is
generally regarded as the platform for good broadband damping properties.
The composition of the present invention may be used with advantage
in the electronics industry as the composition may be tailored to be ultra-clean
by avoiding the presence of acid or polar components; i.e., the composition will
preferably exhibit a leachable ion concentration below 22 ng/cm2 , with
outgassing as measured by Dynamic Headspace Analysis using GC-MS below
910 ng/cm2. Such values are within the parameters of the hard disk drive
industry standards.
The demands on the electronics industry to increase memory capacity
are driving the improvements in cleanliness levels. The development of MR
(magnetoresistive) and GMR (giant magnetoresistivity) head technologies, with
recording heads floating over the memory surface on a molecular layer of air,
make trace amounts of VOC's (volatile organic compounds originating from
the adhesive) operate as miniature "speed bumps" when they condense on the
memory surface. This disrupts the reading and writing process, which is the
essence of the electronic data storage and retrieval process.
The composition of the present invention also, due to its crosslinkable
nature, may be crosslinked to exhibit inherent hardness, cold flow resistance,
heat resistance, and broad band vibration attenuation. By way of example, a
typical shear modulus (G') range measured by Dynamic Mechanical Analysis
is 5xl05 dyne/cm2 (at 1Hz), 2.1xl06 dyne/cm2 (at 100 Hz), 6.2 x 106 dyne/cm2
(at 1 kHz) and 2.6xl07 dyne/cm2 (at 10 kHz). The composition of the present invention can be fine tuned to exhibit a
range of adhesion, as desired.
The composition of the present invention may be used to damp
vibrations or sound in an article by providing a film or layer of a vibration or
sound damping material to the article comprised of the composition such that
the film or layer is capable of attenuating vibration or sound in at least one
vibrational or sound mode. For example, the composition may be coated on a
surface of the article which surface is particulary related to the formation of
vibrations or sound.
The high Tg copolymer (A) used in the composition of the present
invention is comprised of the polymerization reaction product of an alkyl
(meth)acrylate monomer having a Tg >20 °C, optionally a C 1-30 (meth)acrylate
monomer, an optional nitrogen-containing polar monomer, and an optional
epoxy-containing monomer, each as defined below. The monomers are
present in an amount such that the Tg of the resulting polymer is greater than -2
°C.
The alkyl (meth)acrylate monomer having a Tg > 20 °C. may be
selected from but not limited to the group consisting of t-butyl (meth)acrylate,
hexadecyl acrylate, isobornyl (meth)acrylate, cyclododecyl acrylate, methyl
methacrylate, secondary butyl methacrylate, ethyl methacrylate, cyclohexyl
methacrylate and mixtures thereof.
The optional C1-30 (meth)acrylate monomer used in the present invention
may comprise a monomeric (meth)acrylic acid ester of a non-tertiary alcohol wherein the alcohol portion has from 4 to 18 carbon atoms. Exemplary
(meth)acrylate monomers include but are not limited to esters of (meth)acrylic
acid with non-tertiary alcohols such as 1-butanol, 1-pentanol, 2-pentanol, 3-
pentanol, 2-methyl- 1-butanol, 1-methyl-pentanol, 2 -methyl- 1-pentanol, 3-
methyl- 1-pentanol, 2-ethyl-l-butanol, 3,5,5-trimethyl-l-hexanol, 3-heptanol, 2-
octanol, 1-decanol, 1-dodecanol, etc.
Exemplary monomeric (meth)acrylate monomers having a carbon chain
of at least 12 carbon atoms include but are not limited to lauryl acrylate (C12),
tridecylacrylate (C13), myristyl acrylate (C14), palmityl acrylate (C16) and
stearyl acrylate (C18). Such monomers are well-known to those skilled in the
art.
The at least one nitrogen-containing polar monomer may be selected
from a wide range of suitable monomers. Such monomers include, for
example, vinyl monomers having at least one nitrogen atom. Such monomers
include but are not limited to N-mono-substituted acrylamides, such as a
(meth)acrylamide, N-methylacrylamide, N-ethylacrylamide, N-
methylolacrylamide, N-hydroxyethylacrylamide and diacetone acrylamide;
N,N-disubstituted acrylamides such as N,N-dimethylacrylamide, N,N-
diethylacrylamide, N-ethyl-N-aminoethylacrylamide, N-ethyl-N-
hydroethylacrylamide, N,N-dimethylolacrylamide, and N,N-
dihydroxyethylacrylamide, etc.
Exemplary nitrogen-containing monomers may also include but are not
limited to N- vinyl lactam monomers such as N-vinyl-2-pyrrolidone, 5-methyl- N-vinyl-2-pyrrolidone, 5-ethyl-N-vinyl-2-ρyrrolidone, 3 ,3-dimethyl-N-vinyl-2-
pyrrolidone, 3-methyl-N-vinyl-2-pyrrolidone, 3-ethyl-N-vinyl-2-pyrrolidone;
4-methol-N-vinyl-2-pyrrolidone; 4-ethyl-N-vinyl-2-pyrrolidone; N-vinyl-2-
valerolactam; N-vinyl-2-caprolactam; N-vinyl-2-piperidone; and N,N-
dimethylacrylamide and mixtures of any of the foregoing. The corresponding
allyl derivatives thereof are also suitable for use in the present invention. The
noted lactams may also be substituted in the lactam ring by one or more lower
alkyl groups having from 1 to 4 carbon atoms, with methyl; ethyl, or propyl
groups being particularly preferred. The N- vinyl lactam monomer employed
preferably comprises N-vinyl-2-pyrrolidone.
The polymerizable epoxy-containing monomer may be selected from a
variety of vinyl-terminated epoxy-containing monomers. Exemplary
polymerizable monomers include but are not limited to glycidyl esters of an
α,β-ethylenically unsaturated carboxylic acid, such as (meth)acrylic or
crotonoic acid.
Exemplary glycidyl monomers for use in the present invention
accordingly include but are not limited to glycidyl (meth)acrylate, glycidyl
ethacrylate and glycidyl itaconate, acryl glycidyl ether, (meth)allyl glycidyl
ether and 3,4-epoxy-l-vinylcyclohexane.
The alkyl (meth)acrylate monomer is present in the copolymerizable
reactant mixture in an amount ranging from about 20 to 80 percent by weight,
the polymerizable C1-3o (meth)acrylate monomer is present in the mixture in an
amount ranging from about 0 to 50 percent by weight, the nitrogen-containing polar monomer is present in the mixture in an amount ranging from about 0 to
50 percent by weight, and the polymerizable epoxy-containing monomer is
present in the mixture in an amount ranging from about 0 to 50 percent by
weight. The epoxy-containing monomer is preferably present in an amount
greater than 15 percent by weight.
Other monomers in addition to the above monomers may be optionally
included for reasons such as cost reduction, etc. For example, styrene and
vinyl acetate may be incorporated into the copolymer with advantage. Such
monomers, if present, will be employed in amounts such that the resulting
copolymer will still have a Tg greater than 50 °C.
The alkyl (meth)methacrylate monomer is present together with the
nitrogen-containing monomer in an amount such that the resulting copolymer
exhibits a Tg > 50 °C, and preferably at least 60 °C. Copolymer (A) does not
inherently exhibit pressure sensitive adhesive properties. However, the
polymer finds particular utility when blended with low Tg copolymer (B) to
form a crosslinkable pressure sensitive adhesive composition.
Copolymer (B) a copolymer comprised of the polymerization reaction
product of an optional vinyl acetate or vinyl ether component, C(2-
12)alkyl(meth)acrylate, hydroxy(C1-s)alkyl(meth)acrylate, and an optional
polymerizable epoxy-containing monomer (defined in the same manner as
defined in connection with copolymer A). The monomers are present in an
amount such that the Tg of said copolymer (B) is less than about -20 °C. Exemplary hydroxy(C1-5)alkyl(meth)acrylate monomers include but are
not limited to hydroxyethyl(meth)acrylate, hydroxypropyl(meth)acrylate,
hydroxybutyl(meth)acrylate, and corresponding dihydroxy compounds.
While a number of (C2-12)alkyl(meth)acrylate monomers may be
employed, the preferred monomer is 2-ethylhexylacrylate.
The vinyl acetate or. vinyl ether component is present in copolymer (B)
in an amount ranging from about 0 to about 30 percent by weight, the
(C2-12)alkyl(meth)acrylate component is present in said copolymer (B) in an
amount ranging from about 70 to about 98 percent by weight, the hydroxy
(C1.5)alkyl(meth)acrylate component is present in an amount ranging from
about 2 to about 20 percent by weight, and said polymerizable epoxy-
containing monomer is present in an amount ranging from about 0 to about 5
percent by weight.
It may be particularly desirable to avoid the use of vinyl acetate in a
composition which must meet ultra-clean standards to avoid the potential for
the production of an acid component upon hydrolysis of the vinyl acetate upon
contact with moisture in the ambient atmosphere.
Copolymers (A) and (B) are present in said composition in a weight
ratio ranging from about 0:100 to about 60:40, and preferably in a weight ratio
ranging from about 5:95 to about 40:60. The copolymers (A) and (B) may be
blended together by any suitable means such as mechanical mixing using a
propeller-type mixing blade. Depending on the relative weight percentages of polymers (A) and (B),
and the compatibility of the blend, the final blend may have two separate Tg i values, or a single Tg value.
Copolymers (A) and (B) of the present invention can be prepared by any
suitable reaction technique such as free radical initiation techniques in the
presence of a solvent. Exemplary solvents include but are not limited to ethyl
acetate, cyclohexane, ketones or mixtures thereof. Solids content during
polymerization may typically range from about 40% to 60%. Exemplary free
radical initiators include but are not limited to peresters, acyl peroxides and
those of the azo type, such as 2,2'-azobis(isobutyronitrile)', benzoyl peroxide,
lauroyl peroxide, t-butyiperbenzoate, t-butyl peroxypivalate, dibenzyl
peroxydicarbonate, and diisopropyl peroxydicarbonate. Ultraviolet light and
ionizing radiation may also be employed. The free radical initiator is generally
present in the reaction mixture in an amount ranging from 0.01 to 10 % by wt.
based on the total weight of the monomers in the reaction mixture.
Typical polymerization temperatures range from 20 °C. to 150 °C. for
periods of time of from 2 to 24 hours until the desired degree of conversion
occurs. The resulting polymer will preferably exhibit a molecular weight in the
range of 50,000 to 2,000,000.
Various polymer compositions are known in the art which comprise a
glycidyl monomer and one or more of an acrylate and a nitrogen-containing
monomer. U.S. Patent No. 6,200,639 discloses at column 8, lines 25-36 a
copolymer of glycidyl methacrylate and t-butyl methacrylate, optionally in
association with an aromatic vinyl-functional monomer, one or more hydroxyl-
fϊmctional (meth)acrylic monomers and one or more additional monomers.
U.S. Patent No. 5,723,191 discloses a tackified dual cure pressure
sensitive adhesive comprised of a copolymer having an acrylic backbone, a
glycidyl monomer, an unsaturated carboxylic acid monomer, and a vinyl
lactam monomer, together with a tackifier.
U.S. Patent No. 3,787,380 discloses a copolymer of N- vinyl orN-allyl
heterocyclic monomers, and unsaturated ester monomer and a glycidyl
monomer.
U.S. Patent Nos. 4,812,541 and 5,639,811 disclose a pressure sensitive
adhesive copolymer comprised of a N- vinyl lactam monomer, a glycidyl
monomer and an alkyl (meth) acrylate monomer.
U.S. Patent No. 5,270,416 discloses a thermosetting powder comprised
of a glycidyl monomer, a methyl (meth)acrylate, butyl acrylate and styrene.
U.S. Patent No. 3,857,905 discloses a thermosetting coating
composition comprised of a glycidyl monomer, a lower alkyl acrylate and a
methyl acrylate.
Various polymer compositions are also known in the art which are
comprised of both high and low Tg polymer components. See, for example,
U.S. Patent Nos. 3,846,368; 3,998,768; 4,107,235; 5,098,952; 5,098,956; and
5,827,609. U.S. Patent No. 5,827,609 discloses a multilayer pressure sensitive adhesive construction where each layer exhibits a different glass transition
temperature.
Any conventional solvent/diluent may be admixed with the copolymer
blend to permit coating of the composition comprised of the blend of
copolymers (A) and (B) at a sufficiently low viscosity. Exemplary
solvents/diluents include but are not limited to xylene, toluene, butylacetate,
acetone, methyl ethyl ketone, methyl isobutyl ketone, alcohols such as
methanol, ethanol, propanol, butanol; ethylene glycol monomethyl ether,
ethylene glycol monobutyl ether acetate, ethylene glycol monoethyl ether
acetate, ethylene glycol monomethyl ether, ethylene glycol dibutyl ether;
hexane, mineral spirits, and other aliphatic, cycloaliphatic or aromatic
hydrocarbon solvents and other esters, ethers, ketones and alcohols, or mixtures
thereof.
The resulting blend may be coated onto a backing material by any
conventional manner, such as by roll coating, spray coating, or extrusion
coating, etc. by use of conventional extrusion devices. The blend may be
applied together with a solvent (typically having a solids content of about 30
percent by weight) and the solvent subsequently removed (such as by
evaporation) to leave the tacky adhesive layer on the backing material
(preferably having a solvent content of less than about 1 percent by weight).
Typically, evaporation will occur at a temperature in the range of from about
150 °F to about 250 °F to ensure removal of any solvent as well as to permit
crosslinking of the composition by thermocuring. Desirably, the coated composition will have a thickness within the range of about 0.5 mil to about 50
mils.
Exemplary backing materials include but are not limited to flexible and
inflexible backing materials conventionally employed in connection with
pressure sensitive adhesives. Such materials include creped paper, kraft paper,
fabrics (knits, non-wovens, wovens), foil and synthetic polymer films or sheets
such as polyethylene, polypropylene, peel PMMA, polyvinyl chloride,
polyamide, polyimide, poly(ethylene terephthalate), polycarbonate, and
cellulose acetate, as well as glass, ceramics, metallized polymer films and other
composite sheet materials.
The adhesive may be applied to one or both of the aforementioned
backing materials, or sandwiched in alternating fashion between multiple layers
of the aforementioned backing materials, to yield two sided tapes. Also,
adhesives may be combined in discrete layers with or without benefit of a
backing material.
In another embodiment, the adhesive may be applied between two
release substrates or on a 2 side coated differential release substrate to form a
transfer adhesive.
Various additional components may also be incorporated into the
composition to modify the properties or characteristics thereof. A variety of
fillers may be incorporated into the polymer blend to provide desired physical
characteristics. For example, metallic flake filler such as stainless steel flake
having a particle size of 25-75 microns and aspect ratios of 31-94 may be incorporated into the composition in an amount of up to about 60 percent by
weight to enhance vibration/sound-damping properties. Rigid polymers having
a high Tg such as polymethylmethacrylate may be added to produce a
controlled phase separation within the composition to further enhance
vibration/sound-damping of the composition. A variety of conventional
crosslinking compounds (such as blocked polyamines) may also be
incorporated into the composition to enhance crosslinking of the composition.
The present invention is illustrated by the following Examples which are
intended to be merely illustrative in nature and not limiting in scope.
EXAMPLE 1
A high Tg acrylic polymer (comprised of 40%» by wt. t-butyl
methacrylate, 10%> by wt. butyl acrylate, 20%> by wt. N-vinyl-2-pyrrolidone and
30% by wt. glycidyl methacrylate) was prepared in ethyl acetate solvent using
a free radical initiator l,l-di(t-amylperoxy)cyclohexane to a molecular weight
of approximately 200,000 GPC relative to polystyrene and having a first glass
transition temperature (Tg) of about 60°C (measured by DSC) and a second
glass transition temperature (Tg) of above 90°C.
5.76 parts of a low Tg acrylic polymer synthesized (25% by wt. solids in
ethyl acetate solvent) was mixed with 65.06 parts of a second copolymer
(comprised of about 70%> by wt. 2-ethylhexyl acrylate, about 20% by wt. vinyl
acetate, 10% by wt. hydroxyethylacrylate and 0.2% by wt. glycidyl
methacrylate, about 41% by wt. solids). 0.75 parts of Ancamine 2441 solution
in the mixture of isopropanol and methylethylketone solvents was used in the formulation. The resulting adhesive was coated on polyester film and dried for
3 minutes at 90°C and 3 minutes at 140°C to yield films of various thicknesses.
Such films were colaminated to yield a thickness greater than 0.6 mm for
Dynamic Mechanical Analysis (DMA). The DMA Master Curve for frequency
ranging from 1 Hz to above 10 kHz was generated using a Rheometric
Scientific RAA Dynamic Mechanical Analyzer with a parallel plate fixture.
The Storage Modulus (G'), Loss Modulus (G") and the tan delta at different
frequency are summarized in Table 1 below:
Table 1
Dynamic mechanical analysis results
Figure imgf000017_0001
EXAMPLE 2
An adhesive blend comprised of 55.45 parts of a high Tg acrylic
polymer (synthesized from 40% by wt. t-butyl methacrylate, 10% by wt. butyl
acrylate, 20% by wt. N-vinyl-2-pyrrolidone and 30% by wt. glycidyl
methacrylate) and 137.08 parts of a low Tg acrylic polymer (41% by wt. solids
in ethyl acetate solvent of about 70% by wt. 2-ethylhexyl acrylate, about 20%
by wt. vinyl acetate, 10% by wt. hydroxyethylacrylate and 0.2% by wt.
glycidyl methacrylate) was prepared in the mixed solvent of ethyl acetate and
toluene. A 5-mil pressure sensitive adhesive film was generated by coating the blend on polyester film and subsequently removing the solvent using the
following heating conditions: 5 minutes at 65.5°C, 5 minutes at 90°C and 5
minutes at 140°C. The DMA test results of Storage Modulus (G'), Loss
Modulus (G") and tan delta at 1 Hz, 100 Hz, 1 kHz and 10 kHz are summarized
in Table 2 below:
Table 2 Dynamic mechanical analysis results
Figure imgf000018_0001
The cleanliness of the pressure sensitive film was tested for leachable
ions using the ion chromatography analysis. An adhesive sample of 50 cm
placed on aluminum foil was rinsed with 18 Meg-Ohm water and submerged in
20 mis of 18 Meg-Ohm water for extraction at 85°C for one hour. Following
the extraction, the water was removed, filtered and tested for ionic cleanliness
using a Waters 636 Ion Chromatograph. As shown in Table 3 below, the
leachable ions are within the general acceptance criteria for Hard Disk Drive
industry, indicating the ultra high cleanliness of the adhesive composition. Table 3
Summary of ionic chromatography test results
Figure imgf000019_0001
The same pressure sensitive adhesive sample was tested for outgassing
using Dynamic Headspace GC/MS and the test results are shown in Table 4
below:
Table 4
Summary of Outgassing test results
Figure imgf000019_0002
Example 3
A high Tg acrylic polymer was synthesized in ethyl acetate solvent
based on the monomers of 2-ethyl hexyl acrylate (54% by wt.), hydroxy ethyl
acrylate (10% by wt.) and isobornyl methacrylate (36% by wt.), using free
radical initiators 2,2'-azobis-(2-methylbutyronitrile) (Vazo 67) and l,l'-azobis-
1-cyclohexanecarbonitrile (Vazo 88). 115.8 parts of the synthesized acrylic
polymer (about 53% solids in ethyl acetate) was blended with 223.1 parts of a
second acrylic polymer of low Tg (about 41% by wt. solids in ethyl acetate
solvent of about 70% by wt. 2-ethylhexyl acrylate, about 20% by wt. vinyl
acetate, 10% by. wt. hydroxyethylacrylate and 0.2% by wt. glycidyl
methacrylate). The resulting adhesive was coated on polyester film and dried
for 3 minutes at 90°C and 3 minutes at 140°C to generate films of various
thicknesses. Such films were colaminated to give thickness greater than 0.6
mm for Dynamic Mechanical Analysis (DMA). The DMA Master Curve for
frequency ranging from 1 Hz to above 10 kHz was generated using a
Rheometric Scientific RAA Dynamic Mechanical Analyzer with a parallel
plate fixture. The Storage Modulus (GO, Loss Modulus (G") and tan delta at
different frequency were shown in Table 5 below:
Table 5
Dynamic mechanical analysis results
Figure imgf000020_0001

Claims

WHAT IS CLAIMED IS:
1. A pressure sensitive adhesive comprised of the following
composition:
(A) a copolymer comprised of the polymerization reaction product of:
(1) an alkyl (meth)acrylate monomer having a Tg > 20 °C;
(2) optionally a C1-30 (meth)acrylate monomer;
(3) optionally a nitrogen-containing polar monomer; and
(4) optionally a polymerizable epoxy-containing monomer,
said monomers being present in an. amount such that the Tg of said
copolymer (A) is greater than about -2 °C; and
(B) a copolymer comprised of the polymerization reaction product of:
(1) optionally vinyl acetate or vinyl ether;
(2) (C2-12)alkyl(meth)acrylate;
(3) hydroxy(C1-5)alkyl(meth)acrylate; and
(4) optionally a polymerizable epoxy-containing monomer,
said monomers being present in an amount such that the Tg of said
copolymer (B) is less than about -20 °C, and
wherein said copolymers (A) and (B) are present in said composition in
a weight ratio ranging from about 0:100 to about 60:40, preferably about 5:95
to about 60:40.
2. The composition of claim 1 wherein said nitrogen-containing
monomer comprises an N- vinyl lactam monomers.
3. The composition of claim 2 wherein said an N- vinyl lactam monomer
is selected from the group consisting of N-vinyl-2-pyrrolidone, 5-methyl-N-
vinyl-2-pyrrolidone, 5-ethyl-N-vinyl-2-pyrrolidone, 3,3-dimethyl-N-vinyl-2-
pyrrolidone, 3 -methyl-N-vinyl-2-pyrrolidone, 3 -ethyl-N-vinyl-2-pyrrolidone;
4-methol-N-vinyl-2-pyrrolidone; 4-ethyl-N-vinyl-2-pyrrolidone; N-vinyl-2-
valerolactam; N-vinyl-2-caρrolactam; N-vinyl-2-piperidone; N,N-
dimethylacrylamide and mixtures thereof.
4. The composition of claim 1 wherein said C1-30 (meth)acrylate
monomer is an ester of (meth)acrylic acid with a non-tertiary alcohol selected
from the group consisting of 1-butanol, 1-pentanol, 2-pentanol, 3 -pentanol, 2-
methyl- 1 -butanol, 1 -methyl-pentanol, 2-methyl- 1 -pentanol, 3 -methyl- 1 -
pentanol, 2-ethyl-l-butanol, 3,5,5-trimethyl-l-hexanol, 3-heptanol, 2-octanol,
1-decanol, 1-dodecanol and octadecanol.
5. The composition of claim 1 wherein said alkyl (meth)acrylate
monomer having a Tg > 20 °C is selected from the group consisting of t-butyl
(meth)acrylate, hexadecyl acrylate, isobornyl (meth)acrylate, cyclododecyl
acrylate, methyl methacrylate, secondary butyl methacrylate, ethyl
methacrylate, cyclohexyl methacrylate and mixtures thereof.
6. The composition of claim 1 wherein said epoxy resin comprises a
glycidyl monomer.
7. The composition of claim 1 wherein the Tg of said copolymer (A) is
at least -2 °C.
8. The composition of claim 1 wherein said alkyl (meth) acrylate is
present in said copolymer (A) in an amount ranging from about 20 to 80 about
percent by weight.
9. The composition of claim 1 wherein said C1-30 (meth)acrylate
monomer is present in said polymer in an amount ranging from 0 to about 50
percent by weight.
10. The composition of claim 1 wherein said epoxy-containing
monomer is present in said copolymer (A) in an amount ranging from about 0
to about 50 percent by weight, based on the weight of copolymer (B).
11. The composition of claim 1 wherein said epoxy-containing
monomer is present in said copolymer (B) in an amount ranging from about 0
to about 5 percent by weight, based on the weight of copolymer (B).
12. The composition of claim 1 wherein said nitrogen-containing
monomer is present in said copolymer (A) in an amount ranging from about 0
to about 50 percent by weight.
13. The composition of claim 1, wherein said Tg of said copolymer (B)
is below about -20 °C.
14. The composition of claim 1, wherein said vinyl acetate or vinyl ether
is present in said copolymer (B) in an amount ranging from about 0 to about 30
percent by weight.
15. The composition of claim 1, wherein said hydroxy
(C1-5)alkyl(meth)acrylate is present in said copolymer (B) in an amount
ranging from about 2 to about 20 percent by weight.
16. The composition of claim 1, wherein said (C2-12)alkyl(meth)acrylate
is present in said copolymer (B) in an amount ranging from about 70 to about
98 percent by weight.
17. The composition of claim 1, together with a backing material.
18. The composition of claim 1, in the form of a film.
19. A method of damping vibrations or sound in an article comprising
providing a film or layer of a vibration or sound damping material to said
article such that said film or layer is capable of attenuating said vibration or sound in at least one vibrational or sound mode, said film or layer being
comprised of a composition comprised of the following:
(A) a copolymer comprised of the polymerization reaction product of:
(1) an alkyl (meth)acrylate monomer having a Tg > 20 °C;
(2) optionally a C1-30 (meth)acrylate monomer;
(3) optionally a nitrogen-containing polar monomer; and
(4) optionally a polymerizable epoxy-containing monomer,
said monomers being present in an amount such that the Tg of said
copolymer (A) is greater than about -2 °C; and
(B) a copolymer comprised of the polymerization reaction product of:
(1) optionally vinyl acetate or vinyl ether;
(2) (C2-12)alkyl(meth)acrylate;
(3) hydroxy(C1-5)alkyl(meth)acrylate; and
(4) optionally a polymerizable epoxy-containing monomer,
said monomers being present in an amount such that the Tg of said
copolymer (B) is less than about -20 °C, and
wherein said copolymers (A) and (B) are present in said composition in
a weight ratio ranging from about 0: 100 to about 60:40, preferably about 5:95
to about 60:40.
20. The method of claim 19, wherein said article comprises a disk drive
in a computer system. .
21. The method of claim 19 wherein said composition is free of any acid or polar monomers.
22. The method of claim 19 wherein said article comprises a part of an
automobile.
23. The method of claim 19 wherein said article comprises a part of a
home appliance.
24. The method of claim 19 wherein said film or layer is crosslinked.
PCT/US2003/006709 2002-03-15 2003-03-17 Pressure sensitive adhesive for use in vibration/sound-damping WO2003078536A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003216522A AU2003216522A1 (en) 2002-03-15 2003-03-17 Pressure sensitive adhesive for use in vibration/sound-damping

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US36413302P 2002-03-15 2002-03-15
US60/364,133 2002-03-15

Publications (2)

Publication Number Publication Date
WO2003078536A2 true WO2003078536A2 (en) 2003-09-25
WO2003078536A3 WO2003078536A3 (en) 2004-03-25

Family

ID=28041875

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2003/006709 WO2003078536A2 (en) 2002-03-15 2003-03-17 Pressure sensitive adhesive for use in vibration/sound-damping

Country Status (2)

Country Link
AU (1) AU2003216522A1 (en)
WO (1) WO2003078536A2 (en)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012112856A1 (en) * 2011-02-18 2012-08-23 3M Innovative Properties Company Optically clear adhesive, method of use and articles therefrom
US9315689B2 (en) 2010-06-21 2016-04-19 Basf Se Sound damping compositions and methods for application and use
US9920225B2 (en) 2012-09-27 2018-03-20 Avery Dennison Corporation Vibration damping adhesives
US10279567B2 (en) 2013-08-30 2019-05-07 Corning Incorporated Light-weight, high stiffness glass laminate structure
US10350861B2 (en) 2015-07-31 2019-07-16 Corning Incorporated Laminate structures with enhanced damping properties
US10596783B2 (en) 2012-05-31 2020-03-24 Corning Incorporated Stiff interlayers for laminated glass structures
CN113583169A (en) * 2021-08-17 2021-11-02 上海应用技术大学 Difunctional waterborne resin
CN113651923A (en) * 2021-08-20 2021-11-16 上海应用技术大学 Damping water-based resin
CN113683721A (en) * 2021-08-25 2021-11-23 上海应用技术大学 Functional resin emulsion

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4812541A (en) * 1987-12-23 1989-03-14 Avery International Corporation High performance pressure-sensitive adhesive polymers
US5326644A (en) * 1993-02-05 1994-07-05 Avery Dennison Corporation Repulpable pressure-sensitive adhesive compositions
US5464659A (en) * 1991-05-23 1995-11-07 Minnesota Mining And Manufacturing Company Silicone/acrylate vibration dampers
US5723191A (en) * 1989-09-14 1998-03-03 Avery Dennison Corporation Tackified dual cure pressure-sensitive adhesive
US5756584A (en) * 1993-11-10 1998-05-26 Minnesota Mining And Manufacturing Company Tackified pressure sensitive adhesives
US5858521A (en) * 1994-07-25 1999-01-12 Lintec Corporation Vibration damper material comprising a vicso elastic layer of unvulcanized rubber
US6524700B2 (en) * 2000-02-18 2003-02-25 Nec Corporation Pressure sensitive adhesive sheet for wafer sticking

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS538326B2 (en) * 1974-04-10 1978-03-28
JPS5783571A (en) * 1980-11-12 1982-05-25 Toagosei Chem Ind Co Ltd Pressure-sensitive adhesive
JPH01271408A (en) * 1988-04-21 1989-10-30 Shinnakamura Kagaku Kogyo Kk Composition for pressure-sensitive adhesive
JPH04110376A (en) * 1990-08-30 1992-04-10 Sekisui Chem Co Ltd Solvent type pressure-sensitive adhesive composition
JPH07102228A (en) * 1993-10-06 1995-04-18 Mitsui Toatsu Chem Inc Pressure-sensitive adhesive composition and self-adhesive article produced therefrom
JP3921017B2 (en) * 1999-10-08 2007-05-30 リンテック株式会社 Pressure sensitive adhesive sheet
JP2002285106A (en) * 2001-03-27 2002-10-03 The Inctec Inc Active energy ray-curable pressure-sensitive adhesive

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4812541A (en) * 1987-12-23 1989-03-14 Avery International Corporation High performance pressure-sensitive adhesive polymers
US5723191A (en) * 1989-09-14 1998-03-03 Avery Dennison Corporation Tackified dual cure pressure-sensitive adhesive
US5464659A (en) * 1991-05-23 1995-11-07 Minnesota Mining And Manufacturing Company Silicone/acrylate vibration dampers
US5326644A (en) * 1993-02-05 1994-07-05 Avery Dennison Corporation Repulpable pressure-sensitive adhesive compositions
US5756584A (en) * 1993-11-10 1998-05-26 Minnesota Mining And Manufacturing Company Tackified pressure sensitive adhesives
US5858521A (en) * 1994-07-25 1999-01-12 Lintec Corporation Vibration damper material comprising a vicso elastic layer of unvulcanized rubber
US6524700B2 (en) * 2000-02-18 2003-02-25 Nec Corporation Pressure sensitive adhesive sheet for wafer sticking

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
DATABASE CAPLUS [Online] XP002972409 Database accession no. 1995:677527 & JP 7 102 228 A 18 April 1995 *
DATABASE CAPLUS [Online] XP002972410 Database accession no. 2002:748001 & JP 2002 285106 A 03 October 2002 *
DATABASE CAPLUS [Online] XP002972411 Database accession no. 2001:269421 & JP 2001 107005 A 17 April 2001 *
DATABASE CAPLUS [Online] XP002972412 Database accession no. 1982:583628 & JP 57 083 571 A 25 May 1982 *
DATABASE WPI Derwent Publications Ltd., London, GB; AN 1977-88684Y, XP002972413 & JP 50 133 239 A (TOYO INK MFG CO.) 22 October 1975 *
DATABASE WPI Derwent Publications Ltd., London, GB; AN 1992-172529, XP002972414 & JP 4 110 376 A (SEKISUI CHEM. IND. CO. LTD.) 10 April 1992 *

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9315689B2 (en) 2010-06-21 2016-04-19 Basf Se Sound damping compositions and methods for application and use
CN103370387A (en) * 2011-02-18 2013-10-23 3M创新有限公司 Optically clear adhesive, method of use and articles therefrom
KR101789898B1 (en) * 2011-02-18 2017-10-25 쓰리엠 이노베이티브 프로퍼티즈 컴파니 Optically clear adhesive, method of use and articles therefrom
CN103370387B (en) * 2011-02-18 2018-01-19 3M创新有限公司 Optically transparent adhesive, application method and by its obtained product
US9879161B2 (en) 2011-02-18 2018-01-30 3M Innovative Properties Company Optically clear adhesive, method of use and articles therefrom
WO2012112856A1 (en) * 2011-02-18 2012-08-23 3M Innovative Properties Company Optically clear adhesive, method of use and articles therefrom
CN108314979A (en) * 2011-02-18 2018-07-24 3M创新有限公司 Optically transparent adhesive, application method and by its product obtained
US10596783B2 (en) 2012-05-31 2020-03-24 Corning Incorporated Stiff interlayers for laminated glass structures
US11305517B2 (en) 2012-05-31 2022-04-19 Corning Incorporated Stiff interlayers for laminated glass structures
US9920225B2 (en) 2012-09-27 2018-03-20 Avery Dennison Corporation Vibration damping adhesives
US10279567B2 (en) 2013-08-30 2019-05-07 Corning Incorporated Light-weight, high stiffness glass laminate structure
US10350861B2 (en) 2015-07-31 2019-07-16 Corning Incorporated Laminate structures with enhanced damping properties
CN113583169A (en) * 2021-08-17 2021-11-02 上海应用技术大学 Difunctional waterborne resin
CN113651923A (en) * 2021-08-20 2021-11-16 上海应用技术大学 Damping water-based resin
CN113683721A (en) * 2021-08-25 2021-11-23 上海应用技术大学 Functional resin emulsion

Also Published As

Publication number Publication date
AU2003216522A1 (en) 2003-09-29
AU2003216522A8 (en) 2003-09-29
WO2003078536A3 (en) 2004-03-25

Similar Documents

Publication Publication Date Title
JP6710822B2 (en) Adhesive composition, adhesive film formed therefrom, and display member including the same
JP7449138B2 (en) Pressure sensitive adhesive composition and adhesive tape
JP5048994B2 (en) Adhesive composition and optical functional film
US8067475B2 (en) Adhesive sheet comprising hollow parts and method for preparing the same
KR101800470B1 (en) Pressure-sensitive adhesive tape, laminate, and image display device
US20030168166A1 (en) High Tg acrylic polymer and epoxy-containing blend thereof as pressure sensitive adhesive
JP2014152198A (en) Adhesive sheet
JP5212688B2 (en) Optical pressure-sensitive adhesive composition and optical functional film
JP2022065001A (en) Multilayer tapes
JP2006522856A (en) Adhesive blends, articles and methods
JP2017066295A (en) Adhesive composition and adhesive sheet
JP2008260824A (en) Optical self-adhesive composition and optical functional film
JP7287432B2 (en) Resin composition, prepreg, resin-coated metal foil, laminate, printed wiring board, and method for producing resin composition
JP7029456B2 (en) Laminates and touch panels
KR102181673B1 (en) Vibration damping adhesives
CN101772808A (en) Gasket forming material for hard disk unit and gasket for hard disk unit using the same
KR20160131045A (en) Multilayer composite having high internal damping
WO2003078536A2 (en) Pressure sensitive adhesive for use in vibration/sound-damping
WO2003054103A2 (en) Resin with high damping properties
JP4667195B2 (en) Adhesive composition and adhesive member
JP2018016734A (en) Optical film adhesive sheet
JP5544853B2 (en) Optical pressure-sensitive adhesive composition
CN109135632A (en) Adhesive composition, adhesive and preparation method thereof, optical cement and display device
JP4104200B2 (en) Vinyl acetate resin emulsion adhesive composition
CN113966352A (en) Polymers derived from (meth) acrylate macromers, adhesive compositions and articles

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NI NO NZ OM PH PL PT RO RU SC SD SE SG SK SL TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LU MC NL PT SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
122 Ep: pct application non-entry in european phase
NENP Non-entry into the national phase in:

Ref country code: JP

WWW Wipo information: withdrawn in national office

Country of ref document: JP