WO1981002261A1 - Pressure-sensitive adhesive tape produced from photoactive mixture of acrylic monomers and polynuclear-chromo phore-substituted halomethyl-s-triazine - Google Patents
Pressure-sensitive adhesive tape produced from photoactive mixture of acrylic monomers and polynuclear-chromo phore-substituted halomethyl-s-triazine Download PDFInfo
- Publication number
- WO1981002261A1 WO1981002261A1 PCT/US1981/000082 US8100082W WO8102261A1 WO 1981002261 A1 WO1981002261 A1 WO 1981002261A1 US 8100082 W US8100082 W US 8100082W WO 8102261 A1 WO8102261 A1 WO 8102261A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- triazine
- parts
- pressure
- alkyl
- sensitive adhesive
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
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- 0 CC1=C*C(C(Cl)(Cl)Cl)=NC(c2cccc3c2C=CCC3)=N1 Chemical compound CC1=C*C(C(Cl)(Cl)Cl)=NC(c2cccc3c2C=CCC3)=N1 0.000 description 1
- WUXBEQVKJGGZOY-QPJJXVBHSA-N COC1C=CC(/C=C/[C@H]2N=C(C(Cl)(Cl)Cl)N=C(C(Cl)(Cl)Cl)N2)=CC1 Chemical compound COC1C=CC(/C=C/[C@H]2N=C(C(Cl)(Cl)Cl)N=C(C(Cl)(Cl)Cl)N2)=CC1 WUXBEQVKJGGZOY-QPJJXVBHSA-N 0.000 description 1
Classifications
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
- G03F7/0295—Photolytic halogen compounds
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- 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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- 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
- C08F20/00—Homopolymers and 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 a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/12—Esters of monohydric alcohols or phenols
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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
- 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
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/38—Pressure-sensitive adhesives [PSA]
- C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C09J7/385—Acrylic polymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/28—Non-macromolecular organic substances
- C08L2666/36—Nitrogen-containing compounds
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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
- C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
- C09J2301/302—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier the adhesive being pressure-sensitive, i.e. tacky at temperatures inferior to 30°C
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/913—Material designed to be responsive to temperature, light, moisture
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/114—Initiator containing
- Y10S430/12—Nitrogen compound containing
- Y10S430/121—Nitrogen in heterocyclic ring
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/14—Layer or component removable to expose adhesive
- Y10T428/1452—Polymer derived only from ethylenically unsaturated monomer
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/28—Web or sheet containing structurally defined element or component and having an adhesive outermost layer
- Y10T428/2809—Web or sheet containing structurally defined element or component and having an adhesive outermost layer including irradiated or wave energy treated component
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/28—Web or sheet containing structurally defined element or component and having an adhesive outermost layer
- Y10T428/2839—Web or sheet containing structurally defined element or component and having an adhesive outermost layer with release or antistick coating
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/28—Web or sheet containing structurally defined element or component and having an adhesive outermost layer
- Y10T428/2852—Adhesive compositions
- Y10T428/2878—Adhesive compositions including addition polymer from unsaturated monomer
- Y10T428/2891—Adhesive compositions including addition polymer from unsaturated monomer including addition polymer from alpha-beta unsaturated carboxylic acid [e.g., acrylic acid, methacrylic acid, etc.] Or derivative thereof
Definitions
- the invention concerns pressure-sensitive adhesive tape and a method of making such tape by coating a mixture of photopolymerizable monomers onto a backing member and exposing the coated mixture to ultraviolet radiation.
- Pressure-sensitive adhesive tape is generally manufactured by coating onto a backing sheet a solution or emulsion of a pressure-sensitive adhesive polymer and heating the coating to drive off the volatile vehicle.
- Belgian Patent No. 675,420 published May 16, 1966 concerns a process for making pressure-sensitive adhesive tape which evolves essentially no volatiles. While maintaining an inert atmosphere, a mixture of acrylic monomers and a photoinitiator is coated onto a backing sheet and then polymerized with ultraviolet radiation to a pressure-sensitive adhesive state.
- United States Patent No. 4,181,752 discloses a process for making pressure-sensitive adhesive tape which, like that of Belgian Patent No. 675,420, involves the photopolymerization of acrylic monomers. While the Belgian patent discloses nothing of the specific intensity and the specific spectral distribution of the irradiation, the Martens patent discloses that these must be controlled in order to attain desirably high cohesive strength and also to attain high peel resistance. It teaches that the polymerizable mixture should be subjected to radiation in the near ultraviolet region at a rate of irradiation in the 300-400 nanometer
- the pressure-sensitive adhesive layer may be crosslinked, particularly where it is desired to increase the cohesive strength of the adhesive without unduly affecting its compliance.
- This can be achieved by utilizing a photoactive crosslinking agent in conjunction with the photoinitiator.
- Preferred a the photoactive crosslinking agent are certain chromophore-substituted vinylhalomethyl-j5-triazines such as 2,4-bis(trichloromethyl)-6-p-methoxystyryl-;s-triazine which has the formula
- This compound is hereinafter called ,, MOST B .
- the present invention primarily concerns pressure-sensitive adhesive tape having at least one adhesive layer produced from a photopolymerizable mixture of acrylic monomers suc as alkyl acrylates those which become crosslinked during the photopolymerization.
- the photocrosslinkable mixture includes a photoactive agent which is a chromophore-substituted halomethyl-s-triazine, but this differs from MOST in that it has no styryl group, instead having a polynuclear moeity attached directly to its s-triazine ring.
- the photoactive s-triazine employed in the present invention can be made by a more simple and hence more economical process than can MOST, has better solubility in acrylic monomer mixtures than does MOST, and tends to provide desirably shortened reaction times and somewhat greater tolerance to oxygen. MOST tends to lend a yellowish color whereas the photoactive s_-triazine 5 employed in the invention usually produces no observable color.
- While the present invention primarily concerns tape produced from (1) photopolymerizable mixtures of ⁇ _ acrylic monomers which become crosslinked when subjected 10 to ultraviolet radiation, it also concerns tape produced from (2) photoactive mixtures of acrylic polymers which become crosslinked when subjected to ultraviolet radiation.
- the present invention 5 concerns a method of making a pressure-sensitive adhesive tape comprising the steps of (lj Mixing by weight
- the method of the present invention differs from ' 0 that of the Martens patent in that characterized in that the chromophore-substituted halomethyl-£-triazine has the formula
- each of R * j_ and R2 is hydrogen, alkyl (preferably methyl or ethyl), or alkoxy (preferably methoxy or ethoxy).
- R is hydrogen
- 2 may possibly be chlorine or bromine.
- any alkyl or alkoxy group of the ⁇ -triazine ha not more than 12 carbon atoms, and no more than two alkyl and alkoxy groups should have more than 6 carbon atoms. Adjacent alkoxy substituents may be interconnected to for 0 ' a ring.
- the s-triazine may be prepared by the co-trimerization of a polynuclear nitrile with trichloroacetonitrile in the presence of HC1 gas and a -Lewis acid such as AICI3, AlBr3 etc. [Bull. Che . Soc. Japan, Vol. 42, page 2924 (1969)].
- Th preferred first step is to mix alkyl acrylate monomer wit a photoinitiator which is not a crosslinking agent such that the dissolved amount of the photoinitiator provides ⁇ up to 0.5% by weight of the mixture.
- the second step is to expose the mixture to ultraviolet radiation to provide a partially-polymerized syrup having a viscosity of 300 to 20,000 centipoises at ordinary room temperature. Unless the alkyl acrylate 5 monomer was first at least partially polymerized, the viscosity of the mixture would be too low to provide uniform coatings of thicknesses most useful for pressure-sensitive adhesive tapes, e.g., 25 to 250 micrometers.
- the partial photopolymerizing may be stoppe 0 at any point simply by turning off the ultraviolet radiation.
- the third step is to mix with said syrup the above-identified photoactive s-triazine component (b).
- the modified syrup may be coated onto a backing member 5 and exposed to ultraviolet radiation to complete the polymerization.
- the third step may be performed using a syrup which has been prepared by conventional thermal polymerization techniques and has been quenched with air to attain the desired viscosity.
- an uncrosslinked polymer of alkyl acrylate monomer is mixed with the photoactive js-triazine component 5 (b) and the mixture is exposed to ultraviolet radiation, the polymer becomes crosslinked.
- a pressure-sensitive adhesive polymer of an alkyl acrylate which has been polymerized in emulsion or solution may be dissolved . -_ in an organic solvent and then mixed with the photoactive 10 -triazine. After coating this solution onto a flexible backing member and evaporating the solvent, exposure of the coating to ultraviolet radiation causes crosslinking of the polymer.
- an opaque backing member to shield the dried coating from accidental ultraviolet 5 radiation, the uncrosslinked tape may be marketed in commerce and eventually crosslinked by ultimate consumers.
- Photoinitiators which are useful for partially polymerizing alkyl acrylate monomer without crosslinking include the benzoin ethers (such as benzoin methyl ether 0 or benzoin isopropyl ether), substituted benzoin ethers
- acetophenones such as 2,2-diethoxyaceto ⁇ henone and 2,2-dimethoxy-2-phenyl-acetophenone
- substituted alpha-ketols such as 2-methyl-2-hydroxy ⁇ ropiophenone
- 5 aromatic sulfonyl chlorides such as 2-naphthalene- sulfonyl chloride
- photoactive oximes such as 1-phenyl-l,l-propanedione-2-(0-ethoxycarbonyl)oxime] .
- They may be used in amounts which as dissolved provide about 0.001 to 0.5 percent by weight of the alkyl acrylate O monomer, preferably at least 0.01 percent.
- either the amount of the photoactive s_-triazine component (b) should be kept below about 0.5% by weight of the above-identified composition (a) or the intensity of radiation should be reduced so that polymerization proceeds more slowly.
- the extent of polymerization can be monitored b measuring the refractive index of the polymerizable mixture.
- the refractive index may change from about 1.43 for a partially polymerized syrup to abou 1.47 at about 100% reaction.
- the change in refractive index occurs linearly with conversion of the unsaturated moiety. See, for example, discussions about the method i polymerization at Advanced Degrees of Conversion, G. P. Gladyshev and K. M. Gibov, Keter Press, Jerusalem, 1970.
- Alkyl acrylates wherein the alkyl group has 4-1 carbon atoms are readily photopolymerized in the practice of the invention to a pressure-sensitive adhesive state, either alone or in combination with various copolymerizable monoethylenically unsaturated monomers, usually at ratios of about 88-99 parts of the alkyl acrylate or acrylates and correspondingly 12-1 parts by weight of the copolymerizable monomer or monomers.
- the copolymerizable monomer or monomers should have highly polar groups such as are present in acrylic acid, methacrylic acid, itaconic acid, acrylamide, methacrylamide, N-substituted acrylamides, acrylonitrile, methacrylonitrile, hydroxyalkyl acrylates, cyanoethyl acrylate, N-vinylpyrrolidone, and maleic anhydride.
- Other useful copolymerizable monoethylenicall unsatured monomers include alkyl vinyl ethers, vinylidene chloride, styrene, and vinyltoluene.
- Other materials which can be blended with the photoactive mixture of this invention include tackifiers, reinforcing agents, and other modifiers, some of which ma
- Glass microbubbles having an average diameter of 10 to 200 micrometers can be blended with photoactive mixtures of this invention as taught in U.S. Patent No.
- the polymerized product will have a foam-like appearance and be suitable for uses to which foam-backed pressure- sensitive adhesive tapes are put.
- photopolymeriza- tion is carried out in an inert atmosphere.
- Any inert atmosphere such as nitrogen, carbon dioxide, helium or argon is suitable and, as noted above, some oxygen can be tolerated.
- a sufficiently inert atmosphere can be achieved by covering a layer of the photoactive mixture with a 'plastic film which is transparent to ultraviolet radiation and irradiating through that film in air.
- the peak wavelength of the ultraviolet radiation preferably is close to the wavelength of maximum absorption of the photoactive s-triazine component (b).
- Good results have been attained using a bank of 40-watt fluorescent black lamps.
- General Electric and Sylvania each market such a lamp designated "F40BL-Black Light".
- the GE lamp emits mainly between 310 nm and 430 nm with a maximum at 380 nm.
- the Sylvania lamp emits mainly between 310 nm and 400 nm with a maximum at 365 nm.
- Good results have also been obtained with mercury lamps, namely 400 watt and 1000 watt medium-pressure street lights (General Electric HID H400A-33-1).
- QMPI _ ⁇ ⁇ _ intensity has usually been adjusted to 2-4 milliwatts/cm 2 at a distance of 12.5 cm from the coating.
- the mercury street lights provided an intensity of about 2 milliwatts/cm 2 .
- the intensity of the irradiation was
- Pressure-sensitive adhesive tapes of the examples below employed as the backing member biaxially-oriented polyethylene terephthalate film having a thickness of about 2 mils (50 micrometers). Each tape 15 was slit to a width of 1/2 inch (1.27 cm) and had an adhesive, thickness of about 2 mils (50 micrometers). Tapes of Examples 1-7 were tested for Peel Value and Shea Value as indicated below. All failures in the tests for Shear Value were cohesive.
- Peel Value 20 Tape is adhered by its adhesive to a glass plat under the weight of a 4.5-kg hard rubber roller. Peelbac at 180° is measured by attaching the free end of the tape to a scale and moving the glass plate away from the scale at a rate of about 3.8 centimeters per second.
- a strip of tape is adhered by its adhesive to a stainless steel plate under the weight of a 4.5-kg hard rubber roller with a free end of the tape extending beyon the plate and the adhesive contact area being 1/2 inch by 1/2 inch (1.27 cm by 1.27 cm). After 30 minutes, the
- the partial photopolymerizing was accomplished in an inert (nitrogen) atmosphere using a bank of 40-watt fluorescent black lights (GE as described above) to provide coatable syrups of a viscosity (Brookfield) of about 1500 cps.
- a photoactive s-triazine was added to each syrup, sometimes together with additional "Irgacure 11 651, and thoroughly mixed.
- Each mixture was coated using a conventional knife coater onto biaxially-oriented polyethylene terephthalate film. The coated film was passed through an inert (nitrogen) chamber and irradiated with the same fluorescent lamps to provide pressure-sensitive adhesive layers.
- the examples employed the photoactive s-triazines of Table I:
- a pressure-sensitive adhesive tape was prepared from a 50% solution in heptane/toluene/methanol 56/24/20 of a 95:5 polymer of 2-ethylhexyl acrylate:acrylamide which had been solution-polymerized to substantially 100% conversion.
- Photoactive s-triazine I was added to the solution (0.165% of dry weight adhesive) and thoroughly mixed. This was knife-coated [4-mil (0.1 mm) orifice] onto a backing member, dried at 135°C for 5 minutes, and then irradiated in air using a standard medium-pressure mercury lamp (300 watts/inch) at 30 m/min.
- Example 5 The irradiated tape (Example 5) and an otherwise identical unirradiated tape (Comparative Example C-5) had Shear Values [except measured at room temperature and a contact area of 1/2 by 1 inch (1.27 cm by 2.54 cm)] of 10,000 and 100 minutes, respectively.
- a polymer of isooctyl acrylate and acrylic acid (95.5:4.5) was prepared by a conventional emulsion- polymerization technique. The polymer was dried and redissolved in 70:30 heptane: isopropanol, 25% solids.
- EXAMPLE 7 AND COMPARATIVE EXAMPLE C-7 Tapes were prepared from a commercial pressure sensitive adhesive which is understood to be a copolymer comprising a major proportion of 2-ethylhexyl acrylate a minor proportions of vinyl acetate, ethyl acrylate and
- Example 7 was irradiated as in Examples 1-4 in comparison to an unirradiated tape (Example C-7) which w identical except that it did not have any photoactive components. Test results were Shear Value
- the adhesive layer was permanently bonded to the polyethylene terephthalate backing member.
- the adhesive layer would be formed on a backing member having a low-adhesion layer from which the adhesive layer could be transferred.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Physics & Mathematics (AREA)
- Inorganic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Adhesive Tapes (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Polymerisation Methods In General (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BR8106700A BR8106700A (pt) | 1980-02-14 | 1981-01-19 | Fita adesiva sensivel a pressao, produzida com mistura fotoativa de monomeros acrilicos e halometil-s-triazina substuida por cromoforo polinuclear |
| AU67804/81A AU537310B2 (en) | 1980-02-14 | 1981-01-19 | Pressure-sensitive adhesive tape produced from photoactive mixture of acrylic monomers and polynuclear-chromophore- substituted halomethyl-s-triazine |
| DE8181900475T DE3169632D1 (en) | 1980-02-14 | 1981-01-19 | Pressure-sensitive adhesive tape produced from photoactive mixture of acrylic monomers and polynuclear-chromo phore-substituted halomethyl-s-triazine |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US121403 | 1980-02-14 | ||
| US06/121,403 US4329384A (en) | 1980-02-14 | 1980-02-14 | Pressure-sensitive adhesive tape produced from photoactive mixture of acrylic monomers and polynuclear-chromophore-substituted halomethyl-2-triazine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1981002261A1 true WO1981002261A1 (en) | 1981-08-20 |
Family
ID=22396486
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1981/000082 Ceased WO1981002261A1 (en) | 1980-02-14 | 1981-01-19 | Pressure-sensitive adhesive tape produced from photoactive mixture of acrylic monomers and polynuclear-chromo phore-substituted halomethyl-s-triazine |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4329384A (enExample) |
| EP (1) | EP0045769B1 (enExample) |
| JP (1) | JPS643238B2 (enExample) |
| BR (1) | BR8106700A (enExample) |
| CA (1) | CA1145294A (enExample) |
| DE (1) | DE3105342A1 (enExample) |
| ES (1) | ES499307A0 (enExample) |
| IT (1) | IT1170718B (enExample) |
| WO (1) | WO1981002261A1 (enExample) |
| ZA (1) | ZA81988B (enExample) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4599273A (en) * | 1980-08-11 | 1986-07-08 | Minnesota Mining And Manufacturing Co. | Photolabile blocked surfactants and compositions containing the same |
| US4696888A (en) * | 1983-10-12 | 1987-09-29 | Hoechst Aktiengesellschaft | Light-sensitive compounds possessing trichloromethyl groups, a process for their production and light-sensitive mixtures containing these compounds |
| US4740600A (en) * | 1984-05-10 | 1988-04-26 | Minnesota Mining And Manufacturing Company | Photolabile blocked surfactants and compositions containing the same |
| US5055579A (en) * | 1988-03-07 | 1991-10-08 | Hoechst Aktiengesellschaft | Heterocyclic compounds containing 4,6-bis-trichloromethyl-s-triazin-2-ly groups |
| US5064959A (en) * | 1988-03-07 | 1991-11-12 | Hoechst Aktiengesellschaft | Aromatic compounds substituted by 4,6-bis(trichloromethyl)-s-triazin-2-yl groups |
| WO1993013147A1 (en) * | 1991-12-31 | 1993-07-08 | Minnesota Mining And Manufacturing Company | Removable, low melt viscosity acrylic pressure sensitive adhesives |
| NL9301664A (nl) * | 1992-09-29 | 1994-04-18 | Toppan Printing Co Ltd | Lichtgevoelige kleursamenstelling, kleurfilter, werkwijze voor het vervaardigen van een kleurfilter en een weergeefinrichting op basis van een vloeibaar kristal. |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4181752A (en) * | 1974-09-03 | 1980-01-01 | Minnesota Mining And Manufacturing Company | Acrylic-type pressure sensitive adhesives by means of ultraviolet radiation curing |
| US4189323A (en) * | 1977-04-25 | 1980-02-19 | Hoechst Aktiengesellschaft | Radiation-sensitive copying composition |
| US4239850A (en) * | 1977-11-29 | 1980-12-16 | Fuji Photo Film Co., Ltd. | Photopolymerizable composition |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2718259C2 (de) * | 1977-04-25 | 1982-11-25 | Hoechst Ag, 6000 Frankfurt | Strahlungsempfindliches Gemisch |
-
1980
- 1980-02-14 US US06/121,403 patent/US4329384A/en not_active Expired - Lifetime
-
1981
- 1981-01-19 WO PCT/US1981/000082 patent/WO1981002261A1/en not_active Ceased
- 1981-01-19 BR BR8106700A patent/BR8106700A/pt not_active IP Right Cessation
- 1981-01-19 JP JP56500773A patent/JPS643238B2/ja not_active Expired
- 1981-01-19 EP EP81900475A patent/EP0045769B1/en not_active Expired
- 1981-01-27 CA CA000369385A patent/CA1145294A/en not_active Expired
- 1981-02-11 ES ES499307A patent/ES499307A0/es active Granted
- 1981-02-13 IT IT47794/81A patent/IT1170718B/it active
- 1981-02-13 ZA ZA00810988A patent/ZA81988B/xx unknown
- 1981-02-13 DE DE19813105342 patent/DE3105342A1/de not_active Withdrawn
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4181752A (en) * | 1974-09-03 | 1980-01-01 | Minnesota Mining And Manufacturing Company | Acrylic-type pressure sensitive adhesives by means of ultraviolet radiation curing |
| US4189323A (en) * | 1977-04-25 | 1980-02-19 | Hoechst Aktiengesellschaft | Radiation-sensitive copying composition |
| US4239850A (en) * | 1977-11-29 | 1980-12-16 | Fuji Photo Film Co., Ltd. | Photopolymerizable composition |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4599273A (en) * | 1980-08-11 | 1986-07-08 | Minnesota Mining And Manufacturing Co. | Photolabile blocked surfactants and compositions containing the same |
| US4696888A (en) * | 1983-10-12 | 1987-09-29 | Hoechst Aktiengesellschaft | Light-sensitive compounds possessing trichloromethyl groups, a process for their production and light-sensitive mixtures containing these compounds |
| US4740600A (en) * | 1984-05-10 | 1988-04-26 | Minnesota Mining And Manufacturing Company | Photolabile blocked surfactants and compositions containing the same |
| US5055579A (en) * | 1988-03-07 | 1991-10-08 | Hoechst Aktiengesellschaft | Heterocyclic compounds containing 4,6-bis-trichloromethyl-s-triazin-2-ly groups |
| US5064959A (en) * | 1988-03-07 | 1991-11-12 | Hoechst Aktiengesellschaft | Aromatic compounds substituted by 4,6-bis(trichloromethyl)-s-triazin-2-yl groups |
| WO1993013147A1 (en) * | 1991-12-31 | 1993-07-08 | Minnesota Mining And Manufacturing Company | Removable, low melt viscosity acrylic pressure sensitive adhesives |
| NL9301664A (nl) * | 1992-09-29 | 1994-04-18 | Toppan Printing Co Ltd | Lichtgevoelige kleursamenstelling, kleurfilter, werkwijze voor het vervaardigen van een kleurfilter en een weergeefinrichting op basis van een vloeibaar kristal. |
| WO2019123182A1 (en) * | 2017-12-21 | 2019-06-27 | 3M Innovative Properties Company | Polymeric compositions prepared with a controlled radical initiator |
| CN111511861A (zh) * | 2017-12-21 | 2020-08-07 | 3M创新有限公司 | 用受控自由基引发剂制备的聚合物组合物 |
| US10913807B2 (en) | 2017-12-21 | 2021-02-09 | 3M Innovative Properties Company | Polymeric compositions prepared with a controlled radical initiator |
| CN111511861B (zh) * | 2017-12-21 | 2021-06-18 | 3M创新有限公司 | 用受控自由基引发剂制备的聚合物组合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| ES8205844A1 (es) | 1982-07-01 |
| US4329384A (en) | 1982-05-11 |
| EP0045769A1 (en) | 1982-02-17 |
| JPS643238B2 (enExample) | 1989-01-20 |
| BR8106700A (pt) | 1981-12-22 |
| EP0045769B1 (en) | 1985-04-03 |
| IT8147794A0 (it) | 1981-02-13 |
| CA1145294A (en) | 1983-04-26 |
| DE3105342A1 (de) | 1981-12-17 |
| ES499307A0 (es) | 1982-07-01 |
| EP0045769A4 (en) | 1982-07-06 |
| IT1170718B (it) | 1987-06-03 |
| JPS57500105A (enExample) | 1982-01-21 |
| ZA81988B (en) | 1982-03-31 |
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