WO1979001013A1 - Ruban adhesif a pression reticule de copolymere d'acrylate d'alkyle et d'un acide copolymerisable - Google Patents

Ruban adhesif a pression reticule de copolymere d'acrylate d'alkyle et d'un acide copolymerisable Download PDF

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Publication number
WO1979001013A1
WO1979001013A1 PCT/US1979/000288 US7900288W WO7901013A1 WO 1979001013 A1 WO1979001013 A1 WO 1979001013A1 US 7900288 W US7900288 W US 7900288W WO 7901013 A1 WO7901013 A1 WO 7901013A1
Authority
WO
WIPO (PCT)
Prior art keywords
copolymer
carbon atoms
acrylic acid
percent
chromium
Prior art date
Application number
PCT/US1979/000288
Other languages
English (en)
Inventor
J Diamond
Original Assignee
Minnesota Mining & Mfg
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 Minnesota Mining & Mfg filed Critical Minnesota Mining & Mfg
Publication of WO1979001013A1 publication Critical patent/WO1979001013A1/fr

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Classifications

    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
    • H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
    • H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
    • H01B3/44—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes vinyl resins; acrylic resins
    • H01B3/447—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes vinyl resins; acrylic resins from acrylic compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
    • 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
    • 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
    • C08L2666/34—Oxygen-containing compounds, including ammonium and metal salts
    • 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

Definitions

  • the invention concerns a pressure-sensitive adhesive tape, the adhesive layer of which is a copolymer of alkyl acrylate and copolymerizable acid.
  • the tape is normally produced in the form of a wide sheet which may be slit to narrow widths and wound upon itself for convenient storage and shipment.
  • U. S. Patent No. Re.24,906 concerns pressure-sensitive tape adhesive consisting essentially of a copolymer of alkyl acrylate and a minor proportion of copolymerizable monomer such as acrylic acid. That acrylate copolymer provides excellent adhesion and holding power and experiences no observable deterioration even after years of storage in tape form.
  • the acrylate copolymer adhesive may be crosslinked.
  • U. S. Patent No. 2,973,286 teaches crosslinking it using an organic peroxide prior to coating and applying somewhat greater heat than would be necessary merely to dry the coating. However, the crosslinking is difficult to control.
  • U. S. Patent No. 2,925,174 teaches crosslinking the acrylate copolymer by reaction with a polyfunctional compound such as a polyamine, a polyol or a polyepoxide. The resultant tapes tend to be deficient in immediate adhesion, usually called "wet-grab", or if tailored to provide good wet-grab, to be deficient in internal strength at ambient temperatures.
  • U. S. Patent No. 3,284, 423 incorporates a third copolymerizable monomer, glycidyl acrylate or methacrylate, to crosslink the acrylate copolymer.
  • U. S. Patent No. 3,740,366 concerns a class of pressure-sensitive adhesives which is much broader than and includes the acrylate copolymer of Re. 24,906. It says that if such adhesives are crosslinked by a compatible polyvalent metal compound, the shear strength is improved without loss of tackiness and that the adhesive coating becomes resistant to alkaline solutions.
  • polyvalent metal compounds suggested in the patent is chromium acetate.
  • the present invention concerns what is believed to be the first crosslinked acrylate copolymer of the type disclosed in Re. 24,906, the crosslinking of which is easy to control and provides all of the following properties: good solvent resistance good wet-grab good internal strength at high temperatures unchanging properties during prolonged storage good electrical insulating properties.
  • the tape adhesive of the present invention comprises an acrylate copolymer of monomers
  • acrylic acid ester of non-tertiary alcohol the molecules of which have from 1-14 carbon atoms, the average being about 4-12 carbon atoms, at least a major proportion of said molecules having a carbon-to-carbon chain of at least 4 carbon atoms terminating at the hydroxyl oxygen atoms, said chain containing at least about 1/2 the total number of carbon atoms in the alcohol molecule
  • said acrylic acid ester being further characterized as being per se polymerizable to a sticky, stretchable elastic adhesive polymer mass
  • the pressure-sensitive tape adhesive of the present invention includes Cr 3+ ion in an amount up to 0.2 percent by weight of the acrylate copolymer. To provide significant improvements in internal strength and solvent resistance, at least 0.002 weight percent of Cr 3+ ion should be present, and preferably at least 0.005 percent when the acid content of the acrylate copolymer is above three percent. Above about 0.05 percent Cr 3+ ion, the adhesive may have less wet-grab than is desirable for most uses.
  • the adhesive layer of a tape of the present invention should be free from emulsifying agents and hence coated from solution, since it is not known how to obtain uniform coatings from emulsions without using dispersing agents which would be harmful to electrical insulating properties.
  • it should be added to the coating solution as a compound which is soluble in the acrylate copolymer.
  • Such compounds which have been used in the practice of this invention include chromium octoate, chromium acetate, chromium oleate, chromium neodecanoate and chromium naphthenate.
  • the Cr 3+ ion achieves the crosslinking is not clearly understood, it is believed that it forms an ionic or salt bridge between acid groups.
  • the crosslinking appears to proceed to virtual completion at times and temperatures that would have been used to drive off the solvent in the absence of any crosslinking agent.
  • the degree of insolubility attained is surprisingly high in view of the fact that the number of Cr 3+ ions may be only about 1/100 of the number of carboxylic acid groups in the copolymer.
  • the novel adhesive may be combined with a small amount of a highly reactive polyfunctional epoxide. However, to avoid noticeable loss of wet-grab, the amount of the epoxide should be less than that used in U. S.
  • Patent No. 2,925,174 i.e., less than 0.4 equivalent of the epoxide and preferably less than 0.1 equivalent of the epoxide per acid equivalent of the acrylate copolymer. It is believed that the Cr 3+ ion catalyzes reaction between the epoxy groups and the acid groups of the acrylate copolymer in addition to bridging others of the acid groups.
  • the adhesive includes epoxide, some crosslinking continues during storage at room temperature, whereas in the absence of epoxide, no continuing crosslinking has been noticeable.
  • the polymerizable mixture of nontertiary alkyl ester monomer (a) and the copolymerizable acid monomer (b) may include small amounts of other copolymerizable monomers such as ethyl acrylate, vinyl chloride, vinyl acetate, various methacrylic esters, butadiene, isoprene, diallyl phthalate and acrylamide in such limited amounts as do not produce drastically altered properties.
  • the amount of the copolymerizable acid monomer (b) is within the range of 1 to 6 percent of the total weight of the copolymerizable monomers. Below 1% , the resultant adhesive tends to have lower internal strength whereas above 6%, it tends to have reduced wet-grab.
  • adhesive layers of the invention are highly transparent. Inert fillers and pigments may be added for such purposes as to provide color and/or opacity, or to increase firmness. If the tape is to be exposed to certain solvents, the backing and primer coating should also be resistant to those solvents. Backing members which are resistant to most common solvents include biaxially-oriented polyethylene terephthalate, glass cloth, polytetrafluoroethylene, polyimide and metal foils.
  • Tapes of the present invention were tested as follows : Solubility A strip of the tape is immersed in a bottle of acetone. After 3 days at room temperature, the tape is removed and placed in an oven at 65°C overnight, cooled and weighed to determine the loss. In some cases, the same test is performed after holding a roll of the tape in an oven for 96 hours at 65°C.
  • test tape is slit to 1.27-cm width and adhered at the edge of a stainless steel plate by its own adhesive coating to provide a bonded area 1.27 cm square.
  • the tape is pressed into contact with the plate under the weight of 4 passes of a 2040-gram hard-rubber roller and held in an oven at 65°C for 10 minutes before testing at that temperature. With the steel plate in the vertical position, a 500-gram mass is suspended from the adhesive tape and the time to failure is noted. When the test is discontinued without failure, the time until discontinuance is reported with a "greater than" ( > ) sign.
  • Example 1 A copolymer of 98 parts of isooctyl acrylate and 2 parts acrylic acid was prepared as described in Re.24, 906 using ethyl acetate and heptane in 1:2 ratio as solvents and azobisisobutyronitrile as catalyst. The inherent viscosity of the copolymer was 1.51. The product solution contained 24.4% solids and had a coatable viscosity of 5500 cps at 25°C.
  • composition A Added to the product solution was a pigment dispersion comprising titanium dioxide plus a minor proportion of polyterephthalate aldazine which had been ball milled overnight in solvens .
  • the resultant composition (here called "Composition A”) comprised: Parts
  • the coatings were dried in an air-circulating oven at times and temperatures sufficient merely to drive off the solvents, and the resultant tapes were wound upon themselves in roll form.
  • the dried coating weight of the pressure-sensitive adhesive coating in each case was about 10 grains per 24 square inches (42 grams per square meter). Test results were as reported in Table A.
  • Example_3 Tapes were prepared as in Example 1 except using a copolymer of 94 parts isooctyl acrylate and 6 parts acrylic acid. Test results are reported in Table C.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Adhesive Tapes (AREA)

Abstract

Un ruban adhesif sensible a la pression comprenant un copolymere d'acrylate d'alkyle et d'un acide copolymerisable tel que l'acide acrylique, dans lequel l'adhesif comprend une petite quantite d'ions Cr3+ qui reticulent les groupes acides pour obtenir une resistance aux solvants tout en gardant de bonnes qualites adhesives. L'adhesif possede d'excellents proprietes d'isolation electrique.
PCT/US1979/000288 1978-05-01 1979-04-30 Ruban adhesif a pression reticule de copolymere d'acrylate d'alkyle et d'un acide copolymerisable WO1979001013A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US90168178A 1978-05-01 1978-05-01
US901681 1978-05-01

Publications (1)

Publication Number Publication Date
WO1979001013A1 true WO1979001013A1 (fr) 1979-11-29

Family

ID=25414631

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1979/000288 WO1979001013A1 (fr) 1978-05-01 1979-04-30 Ruban adhesif a pression reticule de copolymere d'acrylate d'alkyle et d'un acide copolymerisable

Country Status (2)

Country Link
EP (1) EP0011643A4 (fr)
WO (1) WO1979001013A1 (fr)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0100146A1 (fr) * 1982-07-19 1984-02-08 Minnesota Mining And Manufacturing Company Adhésifs, de type acryle réticulé, rendus collants
EP0197662A1 (fr) * 1985-03-15 1986-10-15 Minnesota Mining And Manufacturing Company Ruban adhésif sensible à la pression ayant une surface essentiellement non collante au toucher
AU604368B2 (en) * 1987-08-28 1990-12-13 Minnesota Mining And Manufacturing Company Unified pressure-sensitive adhesive tape
EP0620834A1 (fr) * 1992-01-10 1994-10-26 Avery Dennison Corporation Autoadhesif a emulsion acrylique separable, resistant a l'eau
US5732485A (en) * 1993-04-13 1998-03-31 Schering-Plough Healthcare Products, Inc. Foot and shoe deodorizer
US6227458B1 (en) 1993-12-03 2001-05-08 Schering-Plough Healthcare Products, Inc. Deodorizer
WO2001032798A1 (fr) * 1999-10-29 2001-05-10 Lts Lohmann Therapie-Systeme Ag Ruban adhesif technique pour la protection anticorrosion
WO2011063070A1 (fr) * 2009-11-23 2011-05-26 3M Innovative Properties Company Adhésifs acryliques sensibles à la pression avec système de réticulation aziridinyl-époxy
US8067504B2 (en) 2009-08-25 2011-11-29 3M Innovative Properties Company Acrylic pressure-sensitive adhesives with acylaziridine crosslinking agents
US8263711B2 (en) 2009-12-23 2012-09-11 3M Innovative Properties Company (Meth)acryloyl-aziridine crosslinking agents and adhesive polymers
US8420214B2 (en) 2008-06-09 2013-04-16 3M Innovative Properties Company Acrylic pressure-sensitive adhesives with aziridine crosslinking agents
US8507612B2 (en) 2009-03-09 2013-08-13 3M Innovative Properties Company Aziridine crosslinking agents for acrylic adhesives

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2925174A (en) * 1956-11-02 1960-02-16 Minnesota Mining & Mfg Solvent-resistant pressure-sensitive adhesive tape
US2973286A (en) * 1956-03-30 1961-02-28 Minnesota Mining & Mfg Solvent-resistant pressure-sensitive polyacrylic adhesive tape and method of preparing same
US3284423A (en) * 1963-12-20 1966-11-08 Monsanto Co Pressure-sensitive creep-resistant resin composition
US3617361A (en) * 1969-01-31 1971-11-02 Basf Ag Manufacture of pressure-sensitive adhesive articles
US3740366A (en) * 1969-04-28 1973-06-19 Rohm & Haas Pressure sensitive adhesive containing carboxylic acid groups and polyvalent metal
US3903332A (en) * 1973-02-15 1975-09-02 Uniroyal Inc Adhesion of polyester to rubber using an adhesive containing added metal compounds
CA984084A (en) * 1970-06-08 1976-02-17 Consolidated-Bathurst Limited Pressure sensitive adhesive composition and splicing film
US4005247A (en) * 1975-10-30 1977-01-25 Ashland Oil, Inc. Pressure sensitive adhesive compositions
US4049847A (en) * 1971-07-12 1977-09-20 Badische Anilin- & Soda-Fabrik Aktiengesellschaft Production of self-adhesive coatings on flat substrates

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU431566B2 (en) * 1969-10-24 1973-01-09 The British Oxygen Company Limited Acrylic dispersions for pressure sensitive adhesives

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2973286A (en) * 1956-03-30 1961-02-28 Minnesota Mining & Mfg Solvent-resistant pressure-sensitive polyacrylic adhesive tape and method of preparing same
US2925174A (en) * 1956-11-02 1960-02-16 Minnesota Mining & Mfg Solvent-resistant pressure-sensitive adhesive tape
US3284423A (en) * 1963-12-20 1966-11-08 Monsanto Co Pressure-sensitive creep-resistant resin composition
US3617361A (en) * 1969-01-31 1971-11-02 Basf Ag Manufacture of pressure-sensitive adhesive articles
US3740366A (en) * 1969-04-28 1973-06-19 Rohm & Haas Pressure sensitive adhesive containing carboxylic acid groups and polyvalent metal
CA984084A (en) * 1970-06-08 1976-02-17 Consolidated-Bathurst Limited Pressure sensitive adhesive composition and splicing film
US4049847A (en) * 1971-07-12 1977-09-20 Badische Anilin- & Soda-Fabrik Aktiengesellschaft Production of self-adhesive coatings on flat substrates
US3903332A (en) * 1973-02-15 1975-09-02 Uniroyal Inc Adhesion of polyester to rubber using an adhesive containing added metal compounds
US4005247A (en) * 1975-10-30 1977-01-25 Ashland Oil, Inc. Pressure sensitive adhesive compositions

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP0011643A4 *

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0100146A1 (fr) * 1982-07-19 1984-02-08 Minnesota Mining And Manufacturing Company Adhésifs, de type acryle réticulé, rendus collants
EP0197662A1 (fr) * 1985-03-15 1986-10-15 Minnesota Mining And Manufacturing Company Ruban adhésif sensible à la pression ayant une surface essentiellement non collante au toucher
AU604368B2 (en) * 1987-08-28 1990-12-13 Minnesota Mining And Manufacturing Company Unified pressure-sensitive adhesive tape
EP0620834A1 (fr) * 1992-01-10 1994-10-26 Avery Dennison Corporation Autoadhesif a emulsion acrylique separable, resistant a l'eau
EP0620834A4 (fr) * 1992-01-10 1995-06-07 Avery Dennison Corp Autoadhesif a emulsion acrylique separable, resistant a l'eau.
US5732485A (en) * 1993-04-13 1998-03-31 Schering-Plough Healthcare Products, Inc. Foot and shoe deodorizer
US6227458B1 (en) 1993-12-03 2001-05-08 Schering-Plough Healthcare Products, Inc. Deodorizer
WO2001032798A1 (fr) * 1999-10-29 2001-05-10 Lts Lohmann Therapie-Systeme Ag Ruban adhesif technique pour la protection anticorrosion
US8420214B2 (en) 2008-06-09 2013-04-16 3M Innovative Properties Company Acrylic pressure-sensitive adhesives with aziridine crosslinking agents
US8507612B2 (en) 2009-03-09 2013-08-13 3M Innovative Properties Company Aziridine crosslinking agents for acrylic adhesives
US8349962B2 (en) 2009-08-25 2013-01-08 3M Innovative Properties Company Acrylic pressure-sensitive adhesives with acylaziridine crosslinking agents
US8067504B2 (en) 2009-08-25 2011-11-29 3M Innovative Properties Company Acrylic pressure-sensitive adhesives with acylaziridine crosslinking agents
WO2011063070A1 (fr) * 2009-11-23 2011-05-26 3M Innovative Properties Company Adhésifs acryliques sensibles à la pression avec système de réticulation aziridinyl-époxy
CN102666613A (zh) * 2009-11-23 2012-09-12 3M创新有限公司 含有氮丙啶基-环氧交联体系的丙烯酸类压敏粘合剂
US8148471B2 (en) 2009-11-23 2012-04-03 3M Innovative Properties Company Acrylic pressure-sensitive adhesives with aziridinyl-epoxy crosslinking system
CN102666613B (zh) * 2009-11-23 2015-07-29 3M创新有限公司 含有氮丙啶基-环氧交联体系的丙烯酸类压敏粘合剂
US8263711B2 (en) 2009-12-23 2012-09-11 3M Innovative Properties Company (Meth)acryloyl-aziridine crosslinking agents and adhesive polymers

Also Published As

Publication number Publication date
EP0011643A1 (fr) 1980-06-11
EP0011643A4 (fr) 1982-01-26

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