WO1997027262A1 - Non-corrosive, low volatiles-containing pressure sensitive adhesive - Google Patents
Non-corrosive, low volatiles-containing pressure sensitive adhesive Download PDFInfo
- Publication number
- WO1997027262A1 WO1997027262A1 PCT/US1997/000206 US9700206W WO9727262A1 WO 1997027262 A1 WO1997027262 A1 WO 1997027262A1 US 9700206 W US9700206 W US 9700206W WO 9727262 A1 WO9727262 A1 WO 9727262A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- copolymer
- graft
- present
- monomer
- acrylic
- Prior art date
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
- C09J151/00—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
- C09J151/06—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers grafted on to homopolymers or copolymers of aliphatic hydrocarbons containing only one carbon-to-carbon double bond
-
- 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
- C09J155/00—Adhesives based on homopolymers or copolymers, obtained by polymerisation reactions only involving carbon-to-carbon unsaturated bonds, not provided for in groups C09J123/00 - C09J153/00
- C09J155/005—Homopolymers or copolymers obtained by polymerisation of macromolecular compounds terminated by a carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/04—Polymers provided for in subclasses C08C or C08F
- C08F290/044—Polymers of aromatic monomers as defined in group C08F12/00
-
- 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
- C09J125/00—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 aromatic carbocyclic ring; Adhesives based on derivatives of such polymers
- C09J125/02—Homopolymers or copolymers of hydrocarbons
- C09J125/04—Homopolymers or copolymers of styrene
- C09J125/08—Copolymers of styrene
- C09J125/14—Copolymers of styrene with unsaturated esters
-
- 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
- C09J133/00—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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/08—Homopolymers or copolymers of acrylic acid esters
-
- 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
- C09J133/00—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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/10—Homopolymers or copolymers of methacrylic acid esters
Definitions
- the present invention is directed to a pressure sensitive adhesive composition comprised of a polymerized acrylic or methacrylic acid ester backbone having grafted thereto pendant polymeric moieties.
- Polymeric compositions are known which are comprised of backbone polymers having grafted thereto pendant polymeric moieties.
- the type of backbone polymer and graft polymeric moiety employed varies depending upon the desired characteristics of the end product. See, for example, U.S. Patent Nos. 3,786,116; 3,832,423; 3,842,146; 3,862,077; 3,879,494; 3,928,255; 3,989,768; 4,085,168; 4,551,388; 4,554,324; 4,656,213; 4,693,776; 4,732,808; and 4,871,812 which disclose various types of such polymers which may or may not exhibit pressure sensitive adhesive properties.
- compositions comprised of a backbone polymer such as an acrylic or methacrylic backbone polymer having attached thereto a graft polymer comprised of a polymerizable macromolecular monomer such as styrene or alpha-methylstyrene. See, for example, U.S. Patent No. 4,554,324, among others, in this regard.
- the acrylic pressure sensitive adhesives such as described in U.S. Patent No. 4,554,324 may be made from an acrylic ester and a polar acrylic monomer.
- the polar acrylic monomer can be one or a mixture of acrylic acid, acrylamide, acrylonitrile, itaconic acid, etc.
- the acrylic ester can be any aliphatic ester of acrylic acid.
- Such monomers are typically polymerized free radically by solution, suspension or emulsion polymerization.
- the acrylate portion of the copolymer is generally present in a generally high concentration and renders the polymer tacky.
- the polar monomer increases the ability of the adhesive to bond to a surface.
- a pressure sensitive adhesive composition that is non-corrosive.
- a normally tacky non-polar monomer-containing phase-separated graft copolymer exhibiting pressure sensitive adhesive properties comprised of a backbone polymer having a polymeric moiety grafted thereto, comprising the reaction product of
- At least one A monomer consisting of a monomeric acrylic or methacrylic acid ester of a non-tertiary alcohol, said alcohol having from 1 to 3 carbon atoms,
- B monomer consisting of a monomeric acrylic or methacrylic acid ester of a non-tertiary alcohol, said alcohol having from 4 to 12 carbon atoms,
- a graft polymeric moiety C having a Tg greater than 20°C. wherein the weight ratio of said at least one A monomer to said at least one B monomer ranges from about 1:2 to 2:1, and the average number of carbon atoms present in the alcohol portion of the total acrylic or (meth) acrylic acid esters of monomers A and B present ranges from about 2.5 to 3.5, with the proviso that when the molecular weight of the graft polymeric moiety C ranges from 2,000 to 13,000 the graft polymeric moiety C is present in an amount of up to about 20% by wt. , and when the molecular weight of the graft polymeric moiety C is greater than 13,000, then the graft polymeric moiety C is present in an amount of up to about 30% by wt.
- the pressure sensitive adhesive graft copolymer of the present invention is comprised of a "hard” reinforcing graft polymeric moiety attached to or copolymerized with a "soft" backbone polymer to obtain a phase-separated adhesive graft copolymer.
- graft copolymers are known which are comprised of a "soft" backbone polymer having an attached "hard” reinforcing graft polymer, such prior art graft copolymers fail to exhibit the desired high performance adhesive properties such as high strength in elevated temperature environments, with the graft copolymer also being non-corrosive and having a low volatiles content.
- the adhesive of the present invention comprises a phase-separated non-polar monomer-containing graft copolymer comprised of the reaction product of copolymerized monomers A and B to form a backbone polymer having a polymeric moiety C grafted thereto, wherein monomer(s) A is a monomeric acrylic or methacrylic acid ester of a non-tertiary alcohol having from 1 to 3 carbon atoms, and monomer(s) B is a monomeric acrylic or methacrylic acid ester of a non-tertiary alcohol having from 4 to 12 carbon atoms.
- the average number of carbon atoms present in the alcohol portion of the total acrylic or (meth)acrylic acid esters of monomers A and B present in the copolymer will be less than 4, and preferably about 2.5 to 3.5 (calculated on mole percent basis) . Most preferably, the average number of carbon atoms is about 3.0.
- a polar monomer(s) such as acrylic acid
- the graft copolymer of the present invention thus contains no polar monomers. Any disadvantage which would normally result from the absence of the polar monomer is addressed by providing for a particular composition of A monomers based on the carbon atom content of the ester.
- Exemplary A monomers include but are not limited to one or more of methyl(meth)acrylate, ethyl(meth)acrylate, n-propyl(meth)acrylate and iso-propyl(meth)acrylate. Such monomers are known to those skilled in the art.
- Exemplary B monomers include but are not limited to esters of acrylic acid or methacrylic acid with non-tertiary alcohols such as 1-butanol, 1-pentanol, 2-pentanol, 3-pentanol, 2-methyl-l-butanol, 1-methyl-l-pentanol, 2-methyl-l-pentanol, 3-methyl-l-pentanol, 2-ethyl-l-butanol, 3,5,5- trimethyl-1-hexanol, 3-heptanol, 2-octanol, 1- decanol, 1-dodecanol, etc.
- Such monomers are known to those skilled in the art.
- the weight ratio of said A monomer(s) to said B monomer(s) in said copolymer ranges from about 1:2 to 2:1, and preferably is about 1:1.
- the A monomer will preferably be present in the graft copolymer in an amount within the range of from about 20 to 65 percent by weight, based on the total weight of the copolymer, with any additional monomers employed (such as the B monomer) and the polymeric graft moiety comprising the remaining portion of the copolymer.
- the graft copolymer consists solely of monomers A and B and graft polymeric moiety C.
- Polymeric graft moiety C has a Tg greater than 20°C.
- the graft moiety is preferably present in an amount of from 1.5 to 2.5 polymeric moieties per polymer backbone on average, and most preferably in an amount of 2 polymeric moieties per chain on average.
- the presence of the graft polymeric moiety within the noted range assists in enabling the copolymer to exhibit sufficient cohesive strength even in view of the presence in the copolymer of significant amounts of the A monomer which might otherwise reduce the cohesive strength of the copolymer.
- the amount of the A monomer employed may accordingly be optimized without otherwise diminishing the adhesive properties of the copolymer.
- the molecular weight of the graft polymeric moiety must be sufficient to result in the formation of a "phase-separated" graft copolymer.
- the molecular weight (number average) of the graft polymeric moiety will range from 2,000 to 60,000.
- the molecular weight of the graft polymeric moiety will preferably range from greater than 30,000 to 60,000.
- the graft polymeric moiety C ranges from 2,000 to 13,000, the graft polymeric moiety is present in an amount of from about 2 to about 20% by wt. When the molecular weight of the graft polymeric moiety C is greater than 13,000, then the graft polymeric moiety is present in an amount of from about 2 to about 30% by weight, based on the total weight of components A, B and C.
- the graft copolymer of the present invention is characterized as being "phase-separated". That is, the backbone of the copolymer and the attached graft are incompatible and thus do not mix together to form a homogeneous phase. Instead, the copolymer backbone forms a continuous phase within which is dispersed the attached graft phase. The dispersed graft discontinuous phase thus acts to mechanically reinforce the continuous phase, thus inhibiting the flow of the continuous phase at an elevated temperature.
- the polymer graft may be attached to the polymer backbone by conventional techniques such as (1) copolymerization with the respective monomers of the backbone polymer or (2) attachment to a preformed backbone polymer via a suitable functional group subsequent to formation of same by copolymerization of monomers A and B.
- the graft copolymer of the present invention may be formed from copolymerized monomers A, B and C, wherein monomers A and B are as defined above and monomer C has the general formula X-Z wherein X is a group copolymerizable with said monomers A and B (preferably a vinyl group) , and
- Z is a polymeric graft moiety having a Tg greater than 20°C, said moiety Z being essentially unreactive under copolymerization conditions, wherein said group X of said monomer C and said monomers A and B are copolymerized to form a polymeric backbone chain having pendant therefrom polymeric moiety Z.
- the graft polymeric moiety may be prepared as a macromer and copolymerized with one or more A and B monomers which form the backbone polymer. See, for instance, the disclosure of U.S. Patent No. 3,786,116, incorporated by reference in its entirety, in this regard.
- Typical copolymerization techniques include but are not limited to conventional free radical initiated copolymerization techniques in the presence of a solvent. Suitable copolymerization temperatures range from about 20°C to 150°C for periods of time of from 2 to 24 hours until the desired degree of conversion occurs. Upon completion of the polymerization process, the solvent is removed and a tacky acrylate copolymer results having an acceptable balance of tack and shear adhesive properties at high temperatures. Depending upon the properties imparted to the backbone polymer as a result of the molecular weight of the particular graft employed, the resulting adhesive may need to be used in solution or emulsion form rather than as a melt adhesive. That is, if the molecular weight of the graft is sufficiently high, the resultant adhesive may be applied to a backing material or substrate in emulsion or solution form, with the water or solvent being removed upon application to the substrate.
- the polymeric moiety Z may be formed from a vinyl aromatic monomer such as styrene, alpha- methylstyrene, indene and p-tert-butylstyrene.
- the polymeric moiety Z may also be formed from vinyl toluene, acenaphthalene, acrylonitrile and methacrylonitrile, organic isocyanates including lower alkyl, phenyl, lower alkyl phenyl and halophenyl isocyanates, organic diisocyanates including lower alkylene, phenylene, and tolylene diisocyanates, lower alkyl and allyl acrylates and methacrylates, including methyl, t-butyl acrylates, and methacrylates; lower olefins, such as ethylene, propylene, butylene, isobutylene, pentene, hexene, etc.; vinyl esters of aliphatic carboxylic acids such as vinyl acetate
- polymer graft The selection of the specific polymerizable monomer for the polymer graft is not critical, since as the above listing suggests, a wide variety of monomers (and the resulting polymeric moieties) can be used with success as a polymeric graft in the copolymer.
- a variety of functional groups may be employed to attach the graft Z to the polymer backbone.
- Exemplary functional groups include but are not limited to
- EXAMPLE 1 A polyacrylate polymer having a polystyrene graft (having a molecular weight of 13,000) is prepared by the following method. In a glass 1 liter reaction vessel the following charge stock was incrementally polymerized under a nitrogen atmosphere at 160-165°F over 8 hour ⁇ with agitation:
- the average number of carbons in the alcohol portion of the acrylic or (meth)acrylic acid esters of the A and B monomers is calculated to be 3.4.
- a polyacrylate polymer having a polystyrene graft (having a molecular weight of 13,000) is prepared by the method of Example 1 from the following charge stock:
- the average number of carbons in the alcohol portion of the acrylic or (meth)acrylic acid esters of the A and B monomers is calculated to be 3.1.
- Composition 1 (Invention) :
- compositions 1, 2 and 3 The average number of carbon atoms in the alcohol portion of the total (meth)acrylic acid esters in compositions 1, 2 and 3 is 3.0855, 4.0 and 2.0, respectively.
- Each of the above compositions was used to produce corresponding graft copolymers 1, 2 and 3 according to the procedure described in Example 1.
- copolymer 1 of the present invention exhibits acceptable pressure sensitive adhesive properties.
- copolymers 2 and 3 exhibit unacceptable pressure sensitive adhesive properties, thus confirming that use of an average number of carbon atoms outside the claimed range of 2.5 to 3.5 yields an unacceptable adhesive.
- the graft copolymer of the present invention has particular utility as a pressure sensitive adhesive.
- the composition may be employed alone or in combination with a suitable backing material in a manner known to those skilled in the art.
- exemplary backing materials include but are not limmited to flexible or inflexible backing materials conventionally employed in the area of pressure sensitive adhesives such as creped paper, kraft paper, fabrics (knits, non-wovens, wovens) , foil and synthetic polymer films such as polyethylene, polypropylene, polyvinyl chloride, poly(ethylene terephthalate) and cellulose acetate, as well as glass, ceramics, metallized polymeric films and other compatible sheet materials.
- Such materials may be coated in any conventional manner with the adhesive composition of the present invention, such as by roll coating, spray coating, extrusion coating, co-extrusion coating, hot melt coating by use of conventional coating devices.
- the composition of the present invention may be applied as a solution and the solvent subsequently removed to leave a tacky adhesive residue on the backing material.
- the coated backing material may take many forms, such as tapes, patches, strips, etc., with the choice and form of backing material being ultimately determined by the end use contemplated.
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP97901932A EP0815180B1 (en) | 1996-01-24 | 1997-01-17 | Non-corrosive, low volatiles-containing pressure sensitive adhesive |
JP9526865A JPH11502563A (en) | 1996-01-24 | 1997-01-17 | Non-corrosive pressure-sensitive adhesive with low volatile content |
AT97901932T ATE193046T1 (en) | 1996-01-24 | 1997-01-17 | NON-CORROSIVE, PRESSURE-SENSITIVE ADHESIVES WITH LOW VOLATILE CONTENT |
DE69702022T DE69702022T2 (en) | 1996-01-24 | 1997-01-17 | NON-CORROSIVE, PRESSURE-SENSITIVE ADHESIVES WITH LOW CONTENT OF VOLATILE SUBSTANCES |
DK97901932T DK0815180T3 (en) | 1996-01-24 | 1997-01-17 | Non-corrosive pressure sensitive adhesive with low volatiles content |
AU15723/97A AU1572397A (en) | 1996-01-24 | 1997-01-17 | Non-corrosive, low volatiles-containing pressure sensitive adhesive |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/590,603 US5703169A (en) | 1996-01-24 | 1996-01-24 | Non-corrosive, low volatiles-containing pressure sensitive adhesive |
US08/590,603 | 1996-01-24 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1997027262A1 true WO1997027262A1 (en) | 1997-07-31 |
Family
ID=24362898
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1997/000206 WO1997027262A1 (en) | 1996-01-24 | 1997-01-17 | Non-corrosive, low volatiles-containing pressure sensitive adhesive |
Country Status (10)
Country | Link |
---|---|
US (2) | US5703169A (en) |
EP (1) | EP0815180B1 (en) |
JP (1) | JPH11502563A (en) |
KR (1) | KR19980703241A (en) |
CN (1) | CN1276000A (en) |
AT (1) | ATE193046T1 (en) |
AU (1) | AU1572397A (en) |
DE (1) | DE69702022T2 (en) |
DK (1) | DK0815180T3 (en) |
WO (1) | WO1997027262A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8152944B2 (en) | 2008-05-09 | 2012-04-10 | Tesa Se | Pressure-sensitive adhesive tapes for bonding printing plates |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6815791B1 (en) * | 1997-02-10 | 2004-11-09 | Fillfactory | Buried, fully depletable, high fill factor photodiodes |
US7199410B2 (en) * | 1999-12-14 | 2007-04-03 | Cypress Semiconductor Corporation (Belgium) Bvba | Pixel structure with improved charge transfer |
TWI225087B (en) * | 2000-09-14 | 2004-12-11 | Rohm & Haas | Adhesive compositions containing graft copolymers |
TWI239339B (en) * | 2000-09-14 | 2005-09-11 | Rohm & Haas | A method of toughening thermoplastic polymers and thermoplastic compositions produced thereby |
KR100885931B1 (en) * | 2002-03-25 | 2009-02-26 | 내쇼날 스타치 앤드 케미칼 인베스트멘트 홀딩 코포레이션 | Rubber-acrylic adhesive formulation |
US8790689B2 (en) | 2003-04-30 | 2014-07-29 | Purdue Pharma L.P. | Tamper resistant transdermal dosage form |
US8778382B2 (en) | 2003-04-30 | 2014-07-15 | Purdue Pharma L.P. | Tamper resistant transdermal dosage form |
US20060013984A1 (en) * | 2003-09-19 | 2006-01-19 | Donald Sandell | Film preparation for seal applicator |
US20050232818A1 (en) * | 2003-09-19 | 2005-10-20 | Donald Sandell | Single sheet seal applicator and cartridge |
US20060011305A1 (en) * | 2003-09-19 | 2006-01-19 | Donald Sandell | Automated seal applicator |
US20050226780A1 (en) * | 2003-09-19 | 2005-10-13 | Donald Sandell | Manual seal applicator |
EP2040983A4 (en) * | 2006-06-26 | 2011-08-03 | Life Technologies Corp | Compressible transparent sealing for open microplates |
EP1894951B1 (en) * | 2006-08-31 | 2018-11-28 | Rohm and Haas Company | Aqueous dispersion of polymeric particles |
EP1894950A1 (en) * | 2006-08-31 | 2008-03-05 | Rohm and Haas France SAS | Aqueous dispersion of polymeric particles |
TWI548709B (en) * | 2013-09-24 | 2016-09-11 | Lg化學股份有限公司 | Pressure-sensitive adhesive composition |
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WO1996008229A2 (en) * | 1994-09-14 | 1996-03-21 | Minnesota Mining And Manufacturing Company | Matrix for transdermal drug delivery |
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-
1996
- 1996-01-24 US US08/590,603 patent/US5703169A/en not_active Expired - Fee Related
-
1997
- 1997-01-17 US US08/785,253 patent/US5703170A/en not_active Expired - Fee Related
- 1997-01-17 WO PCT/US1997/000206 patent/WO1997027262A1/en not_active Application Discontinuation
- 1997-01-17 KR KR1019970706645A patent/KR19980703241A/en not_active Application Discontinuation
- 1997-01-17 EP EP97901932A patent/EP0815180B1/en not_active Expired - Lifetime
- 1997-01-17 DE DE69702022T patent/DE69702022T2/en not_active Expired - Fee Related
- 1997-01-17 JP JP9526865A patent/JPH11502563A/en active Pending
- 1997-01-17 DK DK97901932T patent/DK0815180T3/en active
- 1997-01-17 AU AU15723/97A patent/AU1572397A/en not_active Abandoned
- 1997-01-17 CN CN97190032A patent/CN1276000A/en active Pending
- 1997-01-17 AT AT97901932T patent/ATE193046T1/en not_active IP Right Cessation
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US3879494A (en) * | 1971-02-22 | 1975-04-22 | Cpc International Inc | Polyblends of chemically joined, phase separated thermoplastic graft copolymers |
EP0104046A2 (en) * | 1982-09-16 | 1984-03-28 | Minnesota Mining And Manufacturing Company | Acrylate copolymer pressure-sensitive adhesive composition and sheet materials coated therewith |
US4551388A (en) * | 1983-06-27 | 1985-11-05 | Atlantic Richfield Company | Acrylic hot melt pressure sensitive adhesive coated sheet material |
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---|---|---|---|---|
US8152944B2 (en) | 2008-05-09 | 2012-04-10 | Tesa Se | Pressure-sensitive adhesive tapes for bonding printing plates |
Also Published As
Publication number | Publication date |
---|---|
DE69702022T2 (en) | 2000-12-21 |
DK0815180T3 (en) | 2000-08-14 |
JPH11502563A (en) | 1999-03-02 |
CN1276000A (en) | 2000-12-06 |
EP0815180A1 (en) | 1998-01-07 |
KR19980703241A (en) | 1998-10-15 |
AU1572397A (en) | 1997-08-20 |
US5703169A (en) | 1997-12-30 |
US5703170A (en) | 1997-12-30 |
ATE193046T1 (en) | 2000-06-15 |
DE69702022D1 (en) | 2000-06-21 |
EP0815180B1 (en) | 2000-05-17 |
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