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WO2011018513A1 - Compositions de cyanoacrylate contenant un colorant absorbant les infrarouges et procédé de soudage laser utilisant de telles compositions - Google Patents

Compositions de cyanoacrylate contenant un colorant absorbant les infrarouges et procédé de soudage laser utilisant de telles compositions Download PDF

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Publication number
WO2011018513A1
WO2011018513A1 PCT/EP2010/061830 EP2010061830W WO2011018513A1 WO 2011018513 A1 WO2011018513 A1 WO 2011018513A1 EP 2010061830 W EP2010061830 W EP 2010061830W WO 2011018513 A1 WO2011018513 A1 WO 2011018513A1
Authority
WO
WIPO (PCT)
Prior art keywords
dye
cyanoacrylate
group
region
welded
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
Application number
PCT/EP2010/061830
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English (en)
Inventor
Ciaran Bernard Mcardle
Maria Parals
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Henkel Loctite Ireland Ltd
Original Assignee
Henkel AG and Co KGaA
Henkel Loctite Ireland Ltd
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Application filed by Henkel AG and Co KGaA, Henkel Loctite Ireland Ltd filed Critical Henkel AG and Co KGaA
Publication of WO2011018513A1 publication Critical patent/WO2011018513A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C65/00—Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor
    • B29C65/02—Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor by heating, with or without pressure
    • B29C65/14—Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor by heating, with or without pressure using wave energy, i.e. electromagnetic radiation, or particle radiation
    • B29C65/16—Laser beams
    • B29C65/1629—Laser beams characterised by the way of heating the interface
    • B29C65/1635—Laser beams characterised by the way of heating the interface at least passing through one of the parts to be joined, i.e. laser transmission welding
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C65/00—Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor
    • B29C65/02—Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor by heating, with or without pressure
    • B29C65/14—Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor by heating, with or without pressure using wave energy, i.e. electromagnetic radiation, or particle radiation
    • B29C65/16—Laser beams
    • B29C65/1677—Laser beams making use of an absorber or impact modifier
    • B29C65/1683—Laser beams making use of an absorber or impact modifier coated on the article
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C65/00—Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor
    • B29C65/82—Testing the joint
    • B29C65/8253—Testing the joint by the use of waves or particle radiation, e.g. visual examination, scanning electron microscopy, or X-rays
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C66/00—General aspects of processes or apparatus for joining preformed parts
    • B29C66/01—General aspects dealing with the joint area or with the area to be joined
    • B29C66/05—Particular design of joint configurations
    • B29C66/10—Particular design of joint configurations particular design of the joint cross-sections
    • B29C66/11—Joint cross-sections comprising a single joint-segment, i.e. one of the parts to be joined comprising a single joint-segment in the joint cross-section
    • B29C66/112—Single lapped joints
    • B29C66/1122—Single lap to lap joints, i.e. overlap joints
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C66/00—General aspects of processes or apparatus for joining preformed parts
    • B29C66/40—General aspects of joining substantially flat articles, e.g. plates, sheets or web-like materials; Making flat seams in tubular or hollow articles; Joining single elements to substantially flat surfaces
    • B29C66/41—Joining substantially flat articles ; Making flat seams in tubular or hollow articles
    • B29C66/43—Joining a relatively small portion of the surface of said articles
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C35/00—Heating, cooling or curing, e.g. crosslinking or vulcanising; Apparatus therefor
    • B29C35/02—Heating or curing, e.g. crosslinking or vulcanizing during moulding, e.g. in a mould
    • B29C35/08—Heating or curing, e.g. crosslinking or vulcanizing during moulding, e.g. in a mould by wave energy or particle radiation
    • B29C35/0805—Heating or curing, e.g. crosslinking or vulcanizing during moulding, e.g. in a mould by wave energy or particle radiation using electromagnetic radiation
    • B29C2035/0822—Heating or curing, e.g. crosslinking or vulcanizing during moulding, e.g. in a mould by wave energy or particle radiation using electromagnetic radiation using IR radiation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C65/00—Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor
    • B29C65/02—Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor by heating, with or without pressure
    • B29C65/14—Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor by heating, with or without pressure using wave energy, i.e. electromagnetic radiation, or particle radiation
    • B29C65/16—Laser beams
    • B29C65/1603—Laser beams characterised by the type of electromagnetic radiation
    • B29C65/1606—Ultraviolet [UV] radiation, e.g. by ultraviolet excimer lasers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C65/00—Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor
    • B29C65/02—Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor by heating, with or without pressure
    • B29C65/14—Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor by heating, with or without pressure using wave energy, i.e. electromagnetic radiation, or particle radiation
    • B29C65/16—Laser beams
    • B29C65/1603—Laser beams characterised by the type of electromagnetic radiation
    • B29C65/1612—Infrared [IR] radiation, e.g. by infrared lasers
    • B29C65/1616—Near infrared radiation [NIR], e.g. by YAG lasers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C65/00—Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor
    • B29C65/02—Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor by heating, with or without pressure
    • B29C65/14—Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor by heating, with or without pressure using wave energy, i.e. electromagnetic radiation, or particle radiation
    • B29C65/16—Laser beams
    • B29C65/1629—Laser beams characterised by the way of heating the interface
    • B29C65/1674—Laser beams characterised by the way of heating the interface making use of laser diodes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C65/00—Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor
    • B29C65/02—Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor by heating, with or without pressure
    • B29C65/14—Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor by heating, with or without pressure using wave energy, i.e. electromagnetic radiation, or particle radiation
    • B29C65/16—Laser beams
    • B29C65/1677—Laser beams making use of an absorber or impact modifier
    • B29C65/168—Laser beams making use of an absorber or impact modifier placed at the interface
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C66/00—General aspects of processes or apparatus for joining preformed parts
    • B29C66/70—General aspects of processes or apparatus for joining preformed parts characterised by the composition, physical properties or the structure of the material of the parts to be joined; Joining with non-plastics material
    • B29C66/71—General aspects of processes or apparatus for joining preformed parts characterised by the composition, physical properties or the structure of the material of the parts to be joined; Joining with non-plastics material characterised by the composition of the plastics material of the parts to be joined
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C66/00—General aspects of processes or apparatus for joining preformed parts
    • B29C66/70—General aspects of processes or apparatus for joining preformed parts characterised by the composition, physical properties or the structure of the material of the parts to be joined; Joining with non-plastics material
    • B29C66/73—General aspects of processes or apparatus for joining preformed parts characterised by the composition, physical properties or the structure of the material of the parts to be joined; Joining with non-plastics material characterised by the intensive physical properties of the material of the parts to be joined, by the optical properties of the material of the parts to be joined, by the extensive physical properties of the parts to be joined, by the state of the material of the parts to be joined or by the material of the parts to be joined being a thermoplastic or a thermoset
    • B29C66/739—General aspects of processes or apparatus for joining preformed parts characterised by the composition, physical properties or the structure of the material of the parts to be joined; Joining with non-plastics material characterised by the intensive physical properties of the material of the parts to be joined, by the optical properties of the material of the parts to be joined, by the extensive physical properties of the parts to be joined, by the state of the material of the parts to be joined or by the material of the parts to be joined being a thermoplastic or a thermoset characterised by the material of the parts to be joined being a thermoplastic or a thermoset
    • B29C66/7392—General aspects of processes or apparatus for joining preformed parts characterised by the composition, physical properties or the structure of the material of the parts to be joined; Joining with non-plastics material characterised by the intensive physical properties of the material of the parts to be joined, by the optical properties of the material of the parts to be joined, by the extensive physical properties of the parts to be joined, by the state of the material of the parts to be joined or by the material of the parts to be joined being a thermoplastic or a thermoset characterised by the material of the parts to be joined being a thermoplastic or a thermoset characterised by the material of at least one of the parts being a thermoplastic
    • B29C66/73921—General aspects of processes or apparatus for joining preformed parts characterised by the composition, physical properties or the structure of the material of the parts to be joined; Joining with non-plastics material characterised by the intensive physical properties of the material of the parts to be joined, by the optical properties of the material of the parts to be joined, by the extensive physical properties of the parts to be joined, by the state of the material of the parts to be joined or by the material of the parts to be joined being a thermoplastic or a thermoset characterised by the material of the parts to be joined being a thermoplastic or a thermoset characterised by the material of at least one of the parts being a thermoplastic characterised by the materials of both parts being thermoplastics
    • 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
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0041—Optical brightening agents, organic pigments
    • 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
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/17—Amines; Quaternary ammonium 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
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds

Definitions

  • the present invention relates to infrared absorbing dye-containing cyanoacrylate compositions and a method of using such compositions, such as in forming a weld between at least two surfaces of one or more workpieces, over a joint region, using a laser.
  • Cyanoacrylates are well-known monomers that are quite useful as instant adhesives.
  • the "instant" nature of the adhesives is derived from their high reactivity that relates to their molecular structures. Cyanoacrylates are unique in their ability to instantly polymerise when required yet remain stable when stored or not in use. Nevertheless, such reactive
  • cyanoacrylate compositions have been colored with dyes.
  • European Patent No. 105 062 speaks to certain fluorescent dyes that are soluble in the cyanoacrylate monomers. These dyes are C.I. Solvent Green 5, C.I. Acid red 50 and C.I. Acid Red 52.
  • U.S. Patent No. 6,689,826 (Wojciak) is directed to and claims a cyanoacrylate composition having a cure indicator comprising a cyanoacrylate component; and a dye dissolved in the cyanoacrylate component to provide a solution having a first color, where a resultant cured composition has a second color.
  • the dyes are fluorescent and may be selected from fluorescein, diiodofluorescein, tetrabromofluorescein,
  • dyes in the ⁇ 826 patent include xanthenes and anthraquinones .
  • Fluorans are a preferred class of xanthene dyes suitable for use in the ⁇ 826 patent. Particularly
  • fluorescein D&C Yellow #7
  • dibromofluorescein D&C Orange #5
  • diiodofluorescein D&C Orange #10
  • tetrabromofluorescein D&C Red #21
  • Preferred antrhaquinone dyes in the ⁇ 826 patent are 7, 16-dichloro-6, 15-dihydro-5, 9, 14, 18-anthrazine-tetrone (D&C Blue #9), the disodium salt of 2, 2' - [ ( 9, 10, -dihydro-9, 10-dioxo- 1, 4-anthracenediyl) diimino] bis- [ 5-methylbenzenesulfonic acid (D&C Green #5), 1, 4-bis (4 ' -methylanilino) anthraquinone (D&C Green #6), and l-hydroxy-4- ( 4-methylanilino) anthraquinone (D&C Violet #2) .
  • Laser welding is a known method for welding together materials constructed from plastics.
  • the method involves positioning of two plastic substrates, that must be held in intimate contact with one another.
  • the substrate on the side addressed by the laser must be transparent to visible light and the other substrate may be opaque, to visible light.
  • Part of the region of contact between the two plastic substrates is then exposed to a laser beam.
  • the laser beam passes through the first plastic substrate on the laser address side and may be absorbed by the second plastic substrate which is opaque.
  • the temperature of the absorbing plastic substrate increases, causing the region of contact between the two plastic substrates to melt, thereby forming a weld.
  • This method however requires at least one substrate to be opaque to visible light.
  • the method also includes providing a radiation absorbing material at the joint region in one of the workpieces or between the workpieces which has an absorption band matched to the wavelength of the incident radiation so as to absorb the incident radiation and generate heat for the melting process, the absorption band being substantially outside the visible range so that the material does not affect the appearance of the joint region or the workpieces in visible light.
  • the present invention relates to infrared absorbing dye-containing cyanoacrylate compositions.
  • the present invention relates also to a method of forming a weld between at least two surfaces of one or more workpieces, over a joint region, using a laser and infrared absorbing dye-containing cyanoacrylate compositions.
  • a method of forming a weld between at least two surfaces of one or more workpieces over a joint region includes providing a composition comprising an infrared radiation absorbing material in a reactive carrier; effecting instant bonding the two surfaces to be subsequently welded into intimate contact; exposing the joint region to incident radiation having a wavelength outside the visible range so as to cause melting of the surface of one or both workpieces at the joint region, and allowing the melted material to cool thereby welding the workpieces together.
  • the reactive carrier is a liquid
  • instant bonding would be effected on contact of the two surfaces to be subsequently welded.
  • the reactive carrier is a solid form, such as a powder or film
  • instant bonding would be effected following mild heating in a general sense (as opposed to local fusion effected by a focused laser) .
  • the present invention relates to infrared absorbing dye-containing cyanoacrylate compositions, and a method of forming a weld between at least two surfaces of one or more workpieces, over a joint region, using a laser and infrared absorbing dye-containing cyanoacrylate compositions.
  • the infrared absorbing dye-containing cyanoacrylate composition includes at least one ⁇ -cyanoacrylate monomer of the formula :
  • R 1 represents a straight chain or branched chain alkyl group having 1 to 12 carbon atoms (which may be substituted with a substituent such as a halogen atom or an alkoxy group) , a straight chain or branched chain alkenyl group having 2 to 12 carbon atoms, a straight chain or branched chain alkynyl group having 2 to 12 carbon atoms, a C3-C12 cycloalkyl group, a C6-C20 aralkyl group or any C5-C20 aryl group.
  • R 1 are a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a pentyl group, a neopentyl group, a hexyl group, an allyl group, a methallyl group, a crotyl group, a propargyl group, a cyclohexyl group, a benzyl group, a phenyl group, a cresyl group, a
  • Ethyl cyanoacrylate is a particularly desirable choice for use in the inventive
  • Neopentyl cyanoacrylate is a particularly desirable choice for use in the inventive compositions and is a solid form monomer; melting such a material at approximately 45°C develops an instant adhesive.
  • a single ⁇ -cyanoacrylate monomer or a mixture of two or more of these ⁇ -cyanoacrylate monomers can be used.
  • the above ⁇ -cyanoacrylate monomer used alone as an adhesive, and one or more components such as those set forth below, are used to formulate a commercial composition.
  • the additional components include accelerators; anionic
  • polymerization inhibitors include radical polymerization inhibitors; additives, such as plasticizers, heat stabilizers and toughening agents .
  • the infrared absorbing dye-containing cyanoacrylate composition includes an amount of the ⁇ -cyanoacrylate monomer in the range of from about 50 to 99.5% by weight, such as 60 to 90% by weight, desirable 75% by weight, based on the total weight of the composition.
  • the infrared absorbing dyes useful in the present invention are preferably compatible with the ⁇ -cyanoacrylate monomer and thus creates the ability to formulate a one part composition.
  • the infrared absorbing dye may be dispensed onto a substrate to be welded either before or after the ⁇ -cyanoacrylate monomer is dispensed onto that substrate or another substrate to be laser welded to the first substrate.
  • the infrared absorbing dyes should having the following properties:
  • infrared absorbing dyes include the cyanine dyes, the squarylium dyes, and the croconium dyes.
  • metallized azo dye such as the ones disclosed in U.S. Patent No. 4,892,584
  • rare earth metal chelates such as the ones disclosed in U.S. Patent No. 5,837,042
  • polyester with phthalocyanines, naphthalocyanines, or squarines copolymerized therewith such as the ones disclosed in U.S. Patent No.
  • Other useful dyes include nickel dithiolate, nickel dithiolene, cyanine, squarylium and croconium.
  • Preferred dyes comprise tris (dialkylaminophenyl) aminium (or, tris [4- dialkylamino) phenyl] ammoniumyl) , tetrakis (dialkylaminophenyl) aminium (or, N,N-bis (4-dialkylaminophenyl) -N- [4- (N, N-bis (4- dialkylaminophenyl) -amino) phenyl] aminium), and tetrakis
  • dialkylaminophenyl diimonium or, 2 , 5-cyclohexadiene-l, 4- diylidene-bis [N, N-bis (4-dialkylaminophenyl) -ammonium] ) .
  • the tris (dialkylaminophenyl) aminium dye may be represented by the following structure:
  • Ri through R 6 each independently represent a substituted or unsubstituted alkyl group of 1 to 8 carbon atoms
  • X ⁇ represents an anion
  • Ri through R 6 each independently represent a methyl, ethyl, propyl or butyl group. More particularly, Ri through R 6 may each independently represent an n-propyl or i- propyl group; or an n-butyl, i-butyl, or t-butyl group.
  • Ri and R2 may join to form a ring, or R 3 and R4 may join to form a ring, or R5 and R 6 may join to form a ring .
  • the anion, X ⁇ is represented by hexafluoroantimonate, hexafluorophosphate, hexafluoroarsenate, perchlorate or
  • the tetrakis (dialkylaminophenyl) aminium dye may be represented by the following structure:
  • Ri through R 8 each independently represent a substituted or unsubstituted alkyl group of 1 to 8 carbon atoms
  • X ⁇ represents an anion
  • Ri through R 8 each independently represent a methyl, ethyl, propyl or butyl group. More particularly, Ri through R 8 may each independently represent an n-propyl or i- propyl group; or an n-butyl, i-butyl, or t-butyl group.
  • Ri and R2 may join to form a ring, or R3 and R4 may join to form a ring, or R5 and Re may join to form a ring, or R 7 and R 8 may join to form a ring.
  • the tetrakis (dialkylaminophenyl) diimonium dye may be represented by the following structure:
  • Ri through Rs each independently represent a substituted or unsubstituted alkyl group of 1 to 8 carbon atoms
  • X ⁇ represents an anion
  • Ri through R 8 each independently representing a methyl, ethyl, propyl or butyl group. More particularly, Ri through R 8 may each independently represent an n-propyl or i- propyl group; or an n-butyl, i-butyl, or t-butyl group.
  • Ri and R2 may join to form a ring, or R 3 and R4 may join to form a ring, or R5 and R ⁇ may join to form a ring, or R7 and R 8 may join to form a ring.
  • Cyclic planar compounds consisting of four pyrrole rings bridged to each other by methyne carbon atoms and chelated with a metal ion bearing a +2 charge, such as Pt +2 , Cu +2 , or Zn +2 , palladium porphyrin, metalloazaporphyrins, by cyclic planar compounds consisting of four pyrrole rings bridged to each other by nitrogen atoms and chelated with a metal ion bearing a +2 charge, such as Pt +2 , Cu +2 , Zn +2 , or Pd +2 , Fischer Base dyes, indolene molecules comprising a benzene ring fused to a pyrrole ring with the N in a position adjacent to the juncture.
  • a dienyl group is attached at the pyrrole carbon adjacent the N and is terminated with numerous molecular moieties which are conjugated with double bonded structures and with various alkyl substituents on the indolene ring.
  • the infrared absorbing dyes may be used as discrete components, or in blends of dyes. It is also possible that a blend of dyes containing a non-infrared dye, such as a radio- opaque dye, provided these non-infrared dyes do not confer substantial coloration to the part and of course are compatible with the cyanoacrylate monomer should it be mixed together therewith prior to application on a substrate. Such added non- infrared dyes may be useful in nondestructive testing or examination of subsequent welds.
  • a non-infrared dye such as a radio- opaque dye
  • Infrared dyes absorb radiation in the region beyond 780 nm with high efficiency. That is, these dyes have high extinction coefficients at one or more wavelengths in that spectral region. When this radiation is absorbed from a laser source, the dye dissipates the absorbed energy principally as heat via vibronic relaxations. The heat is localised to the dye and surrounding environment. Here, the surrounding environment is a polymer material, and thus melting occurs at the surface interface between the dye and polymer. If an infrared radiation transmissive polymer material is adjacent to this surface, the melting will cause a weld to occur.
  • the workpieces to be joined by the laser welding method using the infrared absorbing dye-containing cyanoacrylate compositions are constructed of a plastic material, examples of which include polycarbonate (“PC”) , polymethylmethacrylate (“PMMA”), polyamides, and polyesters.
  • the laser should be oriented to pass through for instance an upper substrate to the joint is described in U.S. Patent No. 5,893,959, the contents of which are incorporated herein by reference.
  • the laser address wavelength should be efficiently coupled into strong absorption bands provided by the infrared dye. Suitable laser wavelengths are known to those skilled in the art and may be derived from frequency doubled or tripled Nd:YAGs, Argon ion, Cu vapor, Ruby, HeNe, Krypton ion (647 nm) , diode and dye pumped lasers.
  • the infrared absorbing dye which may be in the reactive carrier.
  • the reactive carrier may be applied by dip coating, dye infusion, painting, spraying, printing, dry burnishing, paste application and the like. If solid, the reactive carrier may be applied as a preformed film or a powder. The reactive carrier, whether applied as a component of the composition or separately from the reactive carrier, will bond the surfaces to be joined at least
  • Bonding will occur instantly from the reactive liquid carriers, or on demand after mild bulk heating from the solid reactive carriers.
  • the infrared radiation will have a
  • a method of forming a weld between at least two surfaces of one or more workpieces over a joint region includes providing a composition comprising an infrared
  • the infrared absorbing dye-containing cyanoacrylate composition -- when in one part form -- is applied on at least one surface of one or more workpieces at the to-be-formed joint region (s ) .
  • Figure 1 shows a first plastics workpiece 1 and a second plastics workpiece 2
  • joint region 3 between the plastics workpiece 1,2 in the composition of the reactive liquid carrier and the radiation absorbing material.
  • the joint is welded by exposing the joint region 3 to a laser beam generating infrared radiation .
  • the first plastics workpiece 1 is transmissive to radiation from the radiation beam 4 and may or may not transmit visible light.
  • transmissive means that the plastics workpiece 1 absorbs less than a predetermined portion of the incident radiation. Accordingly, the plastics workpiece 1 may be transparent or translucent to radiation in the visible spectrum, or may reflect such radiation but typically will not be totally absorbent (i.e., black) .
  • the plasties workpiece 2 also may or may not be transmissive to radiation in the visible spectrum and may or may not absorb infrared radiation directly.
  • the radiation beam 4 has a wavelength outside the visible spectrum but in a range which will be absorbed by the dye .
  • the laser 5 may be an Nd:YAG laser, or a diode laser.
  • the additive When the joint region 3 is exposed to the radiation beam 4, the additive will absorb the radiation. This causes the workpiece, to which the infrared absorbing composition is applied, to heat up melting the plastics workpieces 1,2 in the joint region 3, whereby on cooling the workpieces weld together.
  • the weld is formed, because the materials at the weld are transmissive to radiation in the visible spectrum, the weld itself will make little or no change to the visible appearance of the component. Welding occurs as a result of the heat
  • cyanoacrylate monomers may be prepared by ready thermal depolymerisation of its polymer, so that heat absorbed in the infrared containing polycyanoacrylate may also cause interdiffusion of cyanoacrylate molecules into the substrate.
  • the heat generation at the weld interface is controlled by the absorption coefficient of the dye layer, and the processing parameters.
  • the main parameters are laser power, which is typically between 1OW and 500W, the welding speed
  • Processing can also be carried out with a fixed laser array, which would irradiate the joint area for a defined time.
  • Typical absorbent additives can be selected from chemical groups such as metal phthalocyanine dyes, metalated azo dyes and metalated indoaniline dyes. Table 1 below provides a set of examples of matched sources and materials:
  • the invention also provides a method for nondestructive testing of a laser welded plastic joint enabled by imaging from dye components contained in the region of the weld.
  • the method includes the steps of examining the welded region of intact welded parts by an X-Ray imaging system.
  • the invention also provides a method for providing insigna in a plastic welded part enabled by imaging from dye components contained in the region of the weld.
  • the method includes the steps of examining the welded region of intact welded parts by way of a spectrometer tuned to sense absorbivity of dye components in the welded region.
  • Example 1 PMMA sheet welding: Two clear sheets of polymethylmethacrylate approximately 3mm thick are lap welded using the ClearWeldTM process with a Nd:YAG laser. A 10-15 ⁇ m MMA film containing typically 0.01-0.1 wt % infrared absorbing dye is placed at the interface. The two pieces are clamped together and welded with an applied power of IOOW at speeds in the range 0.1-1. Om/min . The laser beam will be approximately 6mm in diameter and the film 5mm wide.
  • Example 2 PMMA sheet welding: Two clear sheets of polymethylmethacrylate approximately 3mm thick are lap welded using the ClearWeldTM process in combination with adhesive bonding.
  • the MEK based ClearWeldTM absorber dye is applied to only one coupon and the cyanoacrylate monomer to the other, prior to bonding and laser welding.
  • the amount of absorber applied is 50 nl/mm 2 .
  • the laser welding is carried out using a Nd:YAG laser and set at IOOW power, 3 m/min weld speed.
  • Example 3 PMMA sheet welding: Two clear sheets of polymethylmethacrylate approximately 3mm thick are lap welded using the ClearWeldTM process in combination with adhesive bonding.
  • the MEK based ClearWeldTM absorber dye is applied to one coupon and the cyanoacrylate monomer to the other, bringing the two coupons together prior to bonding and laser welding.
  • the amount of absorber applied was 80 nl/mm 2 .
  • the laser welding is carried out using a Nd:YAG laser and set at IOOW power, 3 m/min weld speed.
  • Example 4 PMMA sheet welding: Two clear sheets of polymethylmethacrylate approximately 3mm thick are lap welded using the ClearWeldTM process in combination with adhesive bonding. 10 ml of MEK based ClearWeldTM absorber is mixed with 20 g of cyanoacrylate. Two drops of this mixture are applied to one coupon and the two coupons are brought together and laser welded. The laser welding is carried out using a Nd:YAG laser and set at IOOW power, 3 m/min weld speed.
  • Example 5 Infrared dye-containing cyanoacrylate compositions: The infrared absorbing dye is dissolved in dry acetone forming a dye solution. The dye solution is
  • the dye- containing cyanoacrylate composition subsequently mixed with cyanoacrylate monomer forming the dye- containing cyanoacrylate composition.
  • Two drops of the dye- containing cyanoacrylate composition is applied to one PMMA coupon and then brought together to another PMMA coupon forming an instant joint (about 2 seconds) .
  • Some of the infrared dyes include the ADS 830AT (American Dye Source), S0268 or S2007 (FEW Chemicals), E1125 (Epolight) and IR-27 (Sigma-Aldrich) .
  • Standard dye concentrations in dye-containing cyanoacrylate compositions are from 0,001% to 0,02%.

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  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Mechanical Engineering (AREA)
  • Optics & Photonics (AREA)
  • Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Electromagnetism (AREA)
  • Lining Or Joining Of Plastics Or The Like (AREA)

Abstract

La présente invention porte sur des compositions de cyanoacrylate contenant un colorant absorbant les infrarouges et sur un procédé d'utilisation de telles compositions, par exemple dans la formation d'une soudure entre au moins deux surfaces d'une ou plusieurs pièces à travailler, sur une région de joint, à l'aide d'un laser.
PCT/EP2010/061830 2009-08-13 2010-08-13 Compositions de cyanoacrylate contenant un colorant absorbant les infrarouges et procédé de soudage laser utilisant de telles compositions Ceased WO2011018513A1 (fr)

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Cited By (6)

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Publication number Priority date Publication date Assignee Title
CN103192199A (zh) * 2013-04-18 2013-07-10 苏州光韵达光电科技有限公司 一种用于光纤激光切割陶瓷的吸收剂
US9353092B2 (en) 2013-06-27 2016-05-31 University Of Notre Dame Du Lac Synthesis and use of croconaine compounds
EP2923821B1 (fr) 2014-03-28 2019-08-07 Sogefi Engine Systems USA, Inc. Procédé de soudage direct par laser infrarouge
WO2020172618A3 (fr) * 2019-02-21 2020-10-22 Bambu Vault Llc Thérapie déclenchée à distance
EP3842792A1 (fr) * 2019-12-26 2021-06-30 Dukane IAS, LLC Procédés de mesure de l'absorption spectrale par des objets
EP3943534A1 (fr) * 2020-07-23 2022-01-26 Université de Haute Alsace Utilisation de colorants organiques générant de la chaleur rouge à proche infrarouge pour le retraitement/recyclage de polymères

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US20030138723A1 (en) * 2001-11-21 2003-07-24 Eastman Kodak Company Solid particle dispersions and their use in the preparation of laser thermal media
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Publication number Priority date Publication date Assignee Title
EP0105062A1 (fr) 1981-03-31 1984-04-11 Sumitomo Chemical Company, Limited Composition adhésive colorée à base de cyanoacrylate
US4892584A (en) 1988-12-05 1990-01-09 Eastman Kodak Company Water soluble infrared absorbing dyes and ink-jet inks containing them
US5093147A (en) 1990-09-12 1992-03-03 Battelle Memorial Institute Providing intelligible markings
US5893959A (en) 1994-03-31 1999-04-13 Marquardt Gmbh Workpiece of plastic and production process for such a workpiece
US5837042A (en) 1996-06-10 1998-11-17 Videojet Systems International, Inc. Invisible fluorescent jet ink
US5990197A (en) 1996-10-28 1999-11-23 Eastman Chemical Company Organic solvent based ink for invisible marking/identification
WO2000020157A1 (fr) 1998-10-01 2000-04-13 The Welding Institute Procede de soudage
US6149719A (en) 1998-10-28 2000-11-21 Hewlett-Packard Company Light sensitive invisible ink compositions and methods for using the same
WO2002083798A1 (fr) 2001-04-17 2002-10-24 Gentex Corporation Compositions d'encre contenant des colorants absorbants proche infrarouges et utilisation de ces compositions avec des appareils d'impression par jet d'encre
US6689826B2 (en) 2001-09-14 2004-02-10 Henkel Loctite Corporation Curable cyanoacrylate compositions and method of detecting cure
US20030130381A1 (en) * 2001-10-24 2003-07-10 Detlev Joachimi Laser-absorbing molding compositions with low carbon black contents
US20030138723A1 (en) * 2001-11-21 2003-07-24 Eastman Kodak Company Solid particle dispersions and their use in the preparation of laser thermal media
WO2006074890A1 (fr) 2005-01-14 2006-07-20 Henkel Kommanditgesellschaft Auf Aktien Compositions radiopaques de cyanoacrylate

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103192199A (zh) * 2013-04-18 2013-07-10 苏州光韵达光电科技有限公司 一种用于光纤激光切割陶瓷的吸收剂
US9353092B2 (en) 2013-06-27 2016-05-31 University Of Notre Dame Du Lac Synthesis and use of croconaine compounds
EP2923821B1 (fr) 2014-03-28 2019-08-07 Sogefi Engine Systems USA, Inc. Procédé de soudage direct par laser infrarouge
WO2020172618A3 (fr) * 2019-02-21 2020-10-22 Bambu Vault Llc Thérapie déclenchée à distance
EP3842792A1 (fr) * 2019-12-26 2021-06-30 Dukane IAS, LLC Procédés de mesure de l'absorption spectrale par des objets
US11125683B2 (en) 2019-12-26 2021-09-21 Dukane Ias, Llc Systems and methods for measuring spectral absorption by objects
EP3943534A1 (fr) * 2020-07-23 2022-01-26 Université de Haute Alsace Utilisation de colorants organiques générant de la chaleur rouge à proche infrarouge pour le retraitement/recyclage de polymères
WO2022018209A1 (fr) * 2020-07-23 2022-01-27 Université De Haute-Alsace Utilisation de colorants organiques générateurs de chaleur dans le rouge ou l'infrarouge proche pour retraitement/recyclage de polymères
EP4185630A1 (fr) * 2020-07-23 2023-05-31 Université de Haute-Alsace Utilisation de colorants organiques générateurs de chaleur dans le rouge ou l'infrarouge proche pour retraitement/recyclage de polymères

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