WO1995034263A1 - Laser-markable plastic labels - Google Patents
Laser-markable plastic labels Download PDFInfo
- Publication number
- WO1995034263A1 WO1995034263A1 PCT/US1995/006258 US9506258W WO9534263A1 WO 1995034263 A1 WO1995034263 A1 WO 1995034263A1 US 9506258 W US9506258 W US 9506258W WO 9534263 A1 WO9534263 A1 WO 9534263A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- laser
- label
- core layer
- opaque material
- skin layer
- Prior art date
Links
- 229920003023 plastic Polymers 0.000 title claims description 22
- 239000004033 plastic Substances 0.000 title claims description 22
- 239000000463 material Substances 0.000 claims abstract description 99
- 239000012792 core layer Substances 0.000 claims abstract description 45
- 229920002457 flexible plastic Polymers 0.000 claims abstract description 24
- 239000010410 layer Substances 0.000 claims description 63
- 238000000034 method Methods 0.000 claims description 37
- 230000008569 process Effects 0.000 claims description 21
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 14
- 230000000007 visual effect Effects 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 239000000853 adhesive Substances 0.000 claims description 11
- 230000001070 adhesive effect Effects 0.000 claims description 11
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims description 10
- 239000002245 particle Substances 0.000 claims description 7
- 239000004408 titanium dioxide Substances 0.000 claims description 7
- 239000010445 mica Substances 0.000 claims description 6
- 229910052618 mica group Inorganic materials 0.000 claims description 6
- 229920000098 polyolefin Polymers 0.000 claims description 6
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 3
- 230000001678 irradiating effect Effects 0.000 claims 2
- 238000002372 labelling Methods 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 23
- -1 conditioners Substances 0.000 description 19
- 239000011162 core material Substances 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- 229920001577 copolymer Polymers 0.000 description 15
- 238000010330 laser marking Methods 0.000 description 14
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 13
- 229920000642 polymer Polymers 0.000 description 13
- 238000007639 printing Methods 0.000 description 9
- 239000004743 Polypropylene Substances 0.000 description 7
- 229910002092 carbon dioxide Inorganic materials 0.000 description 7
- 238000001125 extrusion Methods 0.000 description 7
- 229920001155 polypropylene Polymers 0.000 description 7
- 239000004698 Polyethylene Substances 0.000 description 6
- 239000001569 carbon dioxide Substances 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 6
- 239000005038 ethylene vinyl acetate Substances 0.000 description 6
- 229920000573 polyethylene Polymers 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- 239000002356 single layer Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 229920001519 homopolymer Polymers 0.000 description 5
- 239000011159 matrix material Substances 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 238000005520 cutting process Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 4
- 229920000915 polyvinyl chloride Polymers 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 150000001336 alkenes Chemical group 0.000 description 3
- 238000000071 blow moulding Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000011236 particulate material Substances 0.000 description 3
- 239000002861 polymer material Substances 0.000 description 3
- 239000004800 polyvinyl chloride Substances 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 230000001010 compromised effect Effects 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 229920001903 high density polyethylene Polymers 0.000 description 2
- 239000004700 high-density polyethylene Substances 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 238000005549 size reduction Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 235000013175 Crataegus laevigata Nutrition 0.000 description 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 1
- NUFNQYOELLVIPL-UHFFFAOYSA-N acifluorfen Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 NUFNQYOELLVIPL-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000003522 acrylic cement Substances 0.000 description 1
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 1
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- VQLYBLABXAHUDN-UHFFFAOYSA-N bis(4-fluorophenyl)-methyl-(1,2,4-triazol-1-ylmethyl)silane;methyl n-(1h-benzimidazol-2-yl)carbamate Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1.C=1C=C(F)C=CC=1[Si](C=1C=CC(F)=CC=1)(C)CN1C=NC=N1 VQLYBLABXAHUDN-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 239000000882 contact lens solution Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000009998 heat setting Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229920000554 ionomer Polymers 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920000306 polymethylpentene Polymers 0.000 description 1
- 239000011116 polymethylpentene Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920000638 styrene acrylonitrile Polymers 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- G—PHYSICS
- G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
- G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
- G09F3/00—Labels, tag tickets, or similar identification or indication means; Seals; Postage or like stamps
- G09F3/02—Forms or constructions
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
- B41M5/267—Marking of plastic artifacts, e.g. with laser
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65C—LABELLING OR TAGGING MACHINES, APPARATUS, OR PROCESSES
- B65C3/00—Labelling other than flat surfaces
- B65C3/06—Affixing labels to short rigid containers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65C—LABELLING OR TAGGING MACHINES, APPARATUS, OR PROCESSES
- B65C9/00—Details of labelling machines or apparatus
- B65C9/46—Applying date marks, code marks, or the like, to the label during labelling
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
- B65D23/00—Details of bottles or jars not otherwise provided for
- B65D23/08—Coverings or external coatings
- B65D23/0842—Sheets or tubes applied around the bottle with or without subsequent folding operations
- B65D23/085—Sheets or tubes applied around the bottle with or without subsequent folding operations and glued or otherwise sealed to the bottle
-
- G—PHYSICS
- G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
- G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
- G09F3/00—Labels, tag tickets, or similar identification or indication means; Seals; Postage or like stamps
- G09F3/02—Forms or constructions
- G09F2003/0201—Label sheets intended to be introduced in a printer, e.g. laser printer
Definitions
- the present invention relates to flexible, plastic labels for use on flexible plastic bottles, which labels are both ink printable and laser-markable.
- plastic labels for squeezable, flexible plastic bottles have been made from paper coated with pressure sensitive adhesives. More recently, plastics have replaced paper to a large extent for this purpose. Plastic labels tend to exhibit a higher degree of flexibility, squeezability and a greater resistance to water and other chemicals than paper. Accordingly, plastic labels are becoming increasingly popular for use on flexible plastic bottles.
- Attaching flexible plastic labels to flexible plastic bottles is normally accomplished in one of two ways.
- a pressure sensitive adhesive is applied to the label and the label attached to a previously formed bottle by pressure.
- IMFL In Mold Film Label
- the label is placed into the mold used to form the bottle by blow molding and the label incorporated physically into the plastic bottle itself as part of the blow molding operation.
- a heat-activatable adhesive is normally applied to the label for firmly bonding the label to the bottle body.
- flexible plastic labels are attached to flexible plastic bottles at high rates of speed.
- typical industrial applications using pressure sensitive labels can process as many as 200 bottles per minute and even up to 600 bottles per minute.
- typical industrial applications for IMFL 5 to 150 bottles per minute can be made with labels attached.
- the labels must also exhibit additional properties such as die cutability, matrix stripability, dispensability (i.e., with enough stiffness to be dispensed at high speed from a peel plate or handled for insertion in a mold) and the like.
- pressure sensitive labels further need to be repositionable, i.e., when misapplied they can be easily peeled off the bottle in a single piece with all the adhesive remaining on the label.
- the label body is made by coextruding a number of different plastic materials together to form a multilayer coextruded product.
- a real advantage of this approach is that the main body of the film can be formulated to maximize the desired gross mechanical properties of the label, while the skin layers of the product can be tailored for accepting printing ink, for receiving adhesives or both.
- titanium dioxide-coated mica particles Another material also known to impart laser markability to various types of plastics is titanium dioxide-coated mica particles. Such materials are sold, for example, under the name AFFLAIR ® by E. Merk Company of Raway, New Jersey and MEARLIN ® Lustre Pigments sold by the Mearl Corporation of New York, New York.
- the present invention utilizes known laser marking technology to impart laser imprinted images to the unique, flexible, plastic labels made in accordance with the present invention.
- These unique plastic labels are multilayer coextrudates which are produced by coextrusion of at least two different polymer materials to form a product with at least two and preferably at least three distinct polymer layers bonded together.
- such products are composed of an inner core layer and at least one outer skin layer.
- the product will have two outer skin layers, one on each side.
- One of these outer skin layers is typically intended to be ink printable (hereinafter “printing skin”), and accordingly the material used to form this layer and the manner of its extrusion are selected to maximize its ability to accept and retain printing ink.
- the other outer skin (hereinafter “bonding skin”) is intended for bonding or facilitating bonding of the label to a bottle.
- the bonding skin layer can either be adapted to receive a subsequently applied adhesive or, in fact, may constitute the adhesive itself.
- the bonding skin is preferably a material which promotes wdhesion of the acrylic adhesive to the olefin core, for example, an olefin copolymer containing polymerized vinyl acetate.
- a label having a highly olefinic core layer is intended to be attached by IMFL to a highly olefinic bottle made, for example, from HDPE (high density polyethylene)
- the bonding skin layer can itself comprise the heat-activatable adhesive normally used for this purpose.
- a homopolymer or copolymer of ethylene or propylene is a good example of an appropriate material for this purpose.
- the thickness of the inventive labels can vary widely. Typically, they range between 0.5 and 15 mils, more preferably 1 to 10 mils, even more preferably between about 2 and 5 mils, thick. Of this amount, the printing and bonding skins each occupy about 5 to 25 percent of the thickness of the label, more typically about 10 to 15 percent of the thickness of the label, while the core layer occupies the rest.
- manufacture of the inventive labels involves production of a continuous sheet or web of the coextrudate, orientation of the web or sheet usually in a single direction (machine direction) only, and finally cutting or otherwise subdividing the web or sheet into individual, discrete labels.
- the coextruded web or sheet after orientation is usually laminated to a release liner comprising the pressure sensitive adhesive, a release agent such as a silicone resin and a paper or film backing layer.
- the laminate so formed is then typically slit longitudinally into strips and the strips wound up on spools, which are stored and/or sold, as desired.
- the laminate strip after unwinding from the spool is fed to a printer/die cutter.
- This machine ink prints the desired graphics on the coextrudate layer and immediately cuts this layer plus attached adhesive into individual labels.
- a small strip of the coextrudate layer is typically left between adjacent labels so that the coextrudate layer after cutting is composed of a plurality of individual, discrete labels plus an intergral matrix of coextrudate material surrounding the individual labels.
- This matrix is then removed leaving a strip comprising a continuous paper backing layer carrying discrete, physically separated labels thereon, each label comprising an ink- printed coextrudate with attached pressure sensitive adhesive mounted on the backing layer via a silicone release agent.
- This strip is then fed to an automatic label applying machine which manipulates the strip, for example, by sliding or rolling the strip around a peel plate at high speed, to cause the individual labels to automatically detach from the backing strip and be projected onto suitably placed bottles.
- the procedure is similar, except that the coextruded web or sheet is not laminated to a release layer. Rather, the web or sheet, after optional winding up into bulk rolls for storage, is slit and subjected to printing/die cutting with the individual labels produced thereby being bundled together in a stack. The blow-molder then loads individual labels from the stack into the label magazine of his blow-molding machine for automatic incorporation into the blow molded bottles as part of the bottle forming operation.
- coextrudates which have been oriented in the longitudinal, or machine, direction only.
- orientation is done by stretching the coextrudate while still hot in the machine direction at a stretch ratio of about 2:1 to about 9:1, with stretch ratios of 4:1 to 6:1 being typical.
- using a 5:1 stretch ratio will reduce the overall extrudate thickness from 16 mils at the extrusion nozzle to approximately 3.2 mils after stretching and will orient the polymer chains in the machine direction to thereby impart considerable stiffness in this direction but not in the transverse direction.
- Other known methods for orienting polymer films for example compression orientation or "blowing" a film produced by extrusion through an annular orifice, can be used.
- the hot-stretched coextrudates produced as described above can also be annealed or "heat set" in accordance with known techniques.
- this is done after extrusion and initial chilling of the extrudate by reheating the extrudate to an elevated temperature, for example, 300°F.
- the coextrudates can be directly processed into labels. More typically, however, the coextrudates are taken up (i.e. wound around) suitable cores to form rolls of material typically containing 500 to 15,000, preferably 2,000 to 10,000, linear meters of material in the form of continuous sheets or webs. Such rolls, which can be subdivided radially (i.e., cut in planes perpendicular to their axes to form rolls of smaller axial width) or left as is, can be stored, shipped and sold for use as needed.
- the coextrudates of the present invention can be formed from any materials commonly employed for making coextrudate flexible plastic labels.
- a suitable material for making the core layer for many applications in accordance with the present invention is polyethylene of low, medium or high density between 0.915 and 0.965 specific gravity. This is a relatively low cost, extrudable film- forming material whose stiffness is dependent, among other things, on the density selected and whose body and strength are sufficient for most uses.
- Polyethylene of lower densities, down to a specific gravity of 0.890, may be employed for greater flexibility.
- a preferred material for the core layer is polypropylene (or a propylene copolymer) having a flex modulus ranging between about 130,000 and 300,000 psi at 73°F., depending on the stiffness desired.
- Still other preferred materials for forming the core layer comprise copolymers of olefin monomers with ethylenically unsaturated carboxylic acid ester comonomers, such as ethylene-vinyl acetate copolymer, as well as blends of such copolymers with any and all of the other polymers and copolymers described above.
- Still other preferred materials comprise physical blends of (l) polypropylene or copolymers of polypropylene and polyethylene and (2) ethylene-vinyl acetate (EVA) in weight ratios ranging from 50/50 to 80/20, preferably 55/45 to 65/35.
- EVA ethylene-vinyl acetate
- a physical blend of (1) a copolymer of polypropylene and polyethylene and (2) ethylene-vinyl acetate (EVA) is also preferred.
- a preferred core layer is a physical blend of polypropylene and EVA.
- Polystyrene is also a candidate material for the core layer particularly where a stiffer label is desired.
- inorganic fillers may be incorporated into the polymer forming the layer.
- Useful fillers include calcium carbonate, titanium dioxide and blends thereof. Pigments and dyes can also be added for imparting color thereto.
- materials found suitable for the skin layers of the inventive labels are materials which are formed predominantly from polyolefins.
- predominantly from polyolefin is meant that the layer is formed from a homopolymer or copolymer of a polyolefin or blends of such homopolymers and/or copolymers, with the proviso that at least 50% of the polymerized monomers in the layer are polyolefins.
- Examples of such materials are homopolymers and copolymers of ethylene and propylene such as polyethylene, polypropylene and ethylene/propylene copolymer, copolymers of olefin monomers with ethylenically unsaturated carboxylic acid or ethyleni- cally unsaturated carboxylic acid ester comonomers such as ethylene- vinyl acetate copolymer (EVA) and blends of such homopolymers and copolymers.
- EVA ethylene- vinyl acetate copolymer
- the polymers, copolymers and blends described above in connection with the core layer can be used.
- meltable film-forming substances used alone or in combination such as polyethylene methyl acrylic acid, polyethylene ethyl acrylate, polyethylene methyl acrylate, acrylonitrile butadiene styrene polymer, polyethylene vinyl alcohol, nylon, polybutylene, polystyrene, polyurethane, polysulfone, polyvinylidene chloride, polypropylene, polycarbonate, polymethyl pentene, styrene maleic anhydride polymer, styrene acrylonitrile polymer, ionomers based on sodium, potassium, calcium or zinc salts of ethylene/ methacrylic acid, polymethyl methacrylates, cellulosics, fluoroplastics, polyacryloni- triles, and thermoplastic polyesters.
- the intensity of the marks made as a result of laser marking will not be compromised, and in fact may be improved, by restricting the laser- opaque materials to the core of the extrudate rather than in its skins.
- keeping the laser-opaque material out of the skins also has the beneficial effect of not deleteriously affecting the physical properties, particularly the smoothness of the skins or their chemical nature either.
- the coextrudates can be made without adversely affecting the various mechanical properties such as dimensional stability, stiffness, high speed dispensability, die cutability, matrix stripability, repositionability and the like of the label product.
- any type of laser-opaque material can be employed in accordance with the present invention.
- materials known for their ability to absorb and/or reflect laser light of different wave lengths and energy densities and, as a result, "interact" with a polymer material in which they are contained to cause a visible mark to form The type of "interaction,” e.g., thermal degradation of the polymer, simple chemical reaction, generation of gas bubbles, etc., varies depending on the type and operation of the laser employed as well as the type of polymer material employed, and accordingly there must be a "match" of the laser-opaque material with the polymer employed as well as the type and operation of the laser employed.
- any known laser- opaque material can be employed, so long as it "matches" both the polymer as well as the type and operation of the laser employed.
- the preferred laser-opaque materials used in accordance with the present invention are solid, particulate materials.
- Solid particulate materials having a high aspect ratio, particularly those which have a platelet structure, are especially preferred.
- particulate materials it is preferable that they have an average particle size from 0.2 to 400, preferably 0.5 to 60, most preferably 1 to 25 microns .
- Especially preferred laser-opaque materials are titanium dioxide-coated mica particles. These materials are commercially available from E. Merck Corporation of Hawthorne, New York under the designation AFFLAIR ® and The Mearl Corporation of New York, New York under the designation of MEARLIN ® luster pigments. These materials typically have particle sizes of 1 to 200, preferably 1 to 60, more preferably 1 to 25 microns.
- the amount of laser-opaque material to be incorporated into the core layer of the inventive coextrudate products can vary widely. Basically, the minimum amount is that amount which is sufficient to form a visible marking of the desired intensity. The maximum amount, in turn, is usually dictated by economics, amounts over that necessary to produce a mark of a desired intensity being unnecessary. Typically, the amount will be on the order of 0.1 to 10 percent by weight, based on the weight of the material forming the core layer (including any other filler or pigment such as titanium dioxide, calcium carbonate and the like) . More typically, the amount of laser-opaque material will be on the order of about 0.5 to 5 percent by weight.
- the amount of laser opaque material in the core layer of the inventive labels in terms of effective thickness.
- effective thickness is meant the number obtained by multiplying the thickness of the core layer, measured in mils, times the concentration of the laser-opaque material in the core layer, measured in weight percent expressed as a decimal. Measured in this way, it is preferable that the amount of laser opaque material in the core layer be enough so that the effective thickness thereof is 0.005 to 0.15, more preferably 0.01 to 0.10, even more preferably 0.02 to 0.06.
- the labels are irradiated with laser light containing or embodying the desired information or image therein.
- Nd/YAG systems and pulsed carbon dioxide lasers.
- the Nd/YAG systems and carbon dioxide lasers are typically used for plastics.
- eximer lasers have also been used for this purpose.
- each of these types of lasers can be used, although pulsed carbon dioxide TEA (transverse excited atmosphere) lasers are preferred from the point of view of cost and reliability.
- the conditions of laser marking vary widely and are dependent on a number of factors such as the identity and amounts of laser-opaque materials in the films, film thickness and the like.
- energy densities on the order of 0.8 to 36, preferably 1.8 to 28.8, Joules per square centimeter per pulse at pulse durations of 50 to 1,000, preferably 100 to 300, nanoseconds are appropriate.
- the laser beam generated by the laser is passed through a suitable stencil containing the desired information to generate an information-containing laser beam.
- This beam is then focused onto the label to be marked and the label irradiated with the laser light for the imprinting process. Exactly how this is done is well known to those skilled in the art of laser marking, and any conventional procedure for this purpose can be employed in accordance with the present invention.
- a hot coextrudate was produced in accordance with the process described in U.S. 5,242,650 with a total thickness of 17.5 mils. The coextrudate was then hot stretched to make a film of 3.5 mils. In each example, the coextrudate was made with two identical skins, each skin layer making up 10% of the total thickness of the coextrudate and the remainder comprising the core.
- each film was them imprinted with a simulated date and lot code by means of a Blazer 6000 Pulsed Carbon Dioxide Laser made by Lasertechnics Corporation of Albuquerque, New Mexico.
- the laser beam produced was passed through a mask having a simulated date and lot code about one inch wide and then focused to a reduced size onto the target film to imprint the image thereon. Imprinting was done at different energy levels (3 and 4 Joules per pulse) and different reduction ratios (ratio of mask size to image size).
- the laser beam as produced by the laser has an energy density of 0.8 Joules/cm 2 , at a maximum energy of 5 Joules.
- the energy density of the beam as it strikes the target can be reduced from this value by reducing the energy of the laser or increased by reducing (narrowing) the beam size between the mask and the surface of the target.
- the approximate energy densities of the laser beam striking the targets were as follows:
- the laser produces silvery-gray laser imprinted marks.
- the images so produced were visually observed and rated using an arbitrary scale of from 0 (no mark) to 10 (black and very distinct) .
- a coextrudate having the following composition was produced:
- Table 2 shows that the laser marking technique as described above produced images having a fairly high degree of contrast or intensity under essentially all the conditions tried in the experiment. This shows that images of good intensity can be produced in accordance with the present invention, even though the laser-opaque material is buried in the core and not present in the skin layers.
- Example 1 was repeated except that initial film thickness was 15 mils before stretching and final fill thickness was 3 mils after stretching.
- the amount of laser-opaque material in the core was. varied from 0 to 3.8 weight percent, based on the weight of the core, to illustrate the effect of varying concentration of this material.
- the specific compositions of the different layers used in these examples is set forth in the following Table 3. Unless otherwise indicated, the polymers and copolymers used have the same compositions as in Example 1:
- Example 1 was repeated except that the coextrudates in Examples 7 and 8 had the composition set forth in the following Tables 5 and 6:
- Example 9 a single layer extrudate was used, this
- Example 7 shows that when the
- Example 9 was
- Example 9 coextrudate contained a significantly greater overall amount of laser-opaque material than the coextrudate of Example 7. Notwithstanding this greater amount of active ingredient, the images produced in the Example 9 coextrudate have essentially the same visual impact as those of the Example 7 coextrudate.
- Example 7 shows that the results obtained in Example 7 are almost identical to those obtained in Example 4 in which the coextrudate had an effective thickness of laser-opaque material of 0.023. This, in turn, shows that "effective thickness" is a meaningful number.
- Afflair 100 rather than Afflair 110.
- Afflair 100 is slightly larger in particle size, and as can be seen below appears to be slightly less effective.
- Example 14 a single layer extrudate was produced rather than a multi-layer extrudate, while in one of these examples, Example 14, the extrudate was not oriented after extrusion but was simply produced as cast.
- Table 8 The results obtained are set forth in the following Table 8:
- Example 11 Comparison of Examples 10 and 11 in the above Table 8 shows that providing an extrudate with protective skins as accomplished in accordance with the present invention, does not hurt and also may even prevent burn through at more intense conditions.
- the composite of Example 11 is essentially the same as Example 10 in terms of the active thickness and active ingredient concentration, the only difference between that in Example 11, protective skins having no laser-opaque material therein are provided. This is significant in that it shows the coextrudated skins can be fine tuned to meet performance criteria without reducing laser-markability at the same additive cost.
- Example 12 Comparison of Example 12, in which a single layer extrudate thicker than that of Example 10 and hence having more overall laser- opaque material than in Examples 10 or 11 (0.027 effective thickness rather than 0.0252) shows that the visual impact of this extrudate is no better than that of the coextrudate of Example 11 even though the extrudate of Example 12 has more laser-opaque material.
- Examples 13 and 14 are comparable in that both have the same effective thickness of laser-opaque material.
- the Example 14 product which is a single layer extrudate not subjected to orientation, provides a visual impact which is noticeably less intense than that provided by the Example 13 product which is composed of multiple layers having been oriented in the machine direction. This shows that the combination of burying the laser-opaque material in the core and orienting in at least the machine direction facilitates reduction in the amount of expensive laser-opaque material necessary to produce a visually acceptable image.
- Example 15
- the recipe for an opaque white flexible film with a print layer, and an adhesive layer is as follows:
- the above film was coextruded as in previous Examples 2 through 7, but the coextrudate thickness was 20 mils, and stretching was done to produce a film of 4.0 mils. As in the previous examples, the thickness of the top and bottom layers were each 10% of the total, the central layer making up the remaining 80%.
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- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- General Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Theoretical Computer Science (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
- Laminated Bodies (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Blow-Moulding Or Thermoforming Of Plastics Or The Like (AREA)
- Labeling Devices (AREA)
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP95922091A EP0766546B1 (en) | 1994-06-13 | 1995-06-06 | Laser-markable plastic labels |
AU26901/95A AU709752B2 (en) | 1994-06-13 | 1995-06-06 | Laser-markable plastic labels |
AT95922091T ATE201318T1 (en) | 1994-06-13 | 1995-06-06 | LASER MARKABLE PLASTIC LABELS |
DE69521045T DE69521045T2 (en) | 1994-06-13 | 1995-06-06 | LASER-MARKABLE PLASTIC LABELS |
BR9508699A BR9508699A (en) | 1994-06-13 | 1995-06-06 | Process for forming a visual image on a flexible plastic label plastic label combination process for attaching a label to a flexible plastic bottle coextruded bottle useful for the manufacture of labels and material roll |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US25930194A | 1994-06-13 | 1994-06-13 | |
US08/259,301 | 1994-06-13 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1995034263A1 true WO1995034263A1 (en) | 1995-12-21 |
Family
ID=22984380
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1995/006258 WO1995034263A1 (en) | 1994-06-13 | 1995-06-06 | Laser-markable plastic labels |
Country Status (8)
Country | Link |
---|---|
EP (1) | EP0766546B1 (en) |
AT (1) | ATE201318T1 (en) |
AU (1) | AU709752B2 (en) |
BR (1) | BR9508699A (en) |
CA (1) | CA2192850A1 (en) |
DE (1) | DE69521045T2 (en) |
ES (1) | ES2157329T3 (en) |
WO (1) | WO1995034263A1 (en) |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2762425A1 (en) * | 1997-04-18 | 1998-10-23 | Chevillot Sa | INFALSIFIABLE, INDELEBILE AND CONTRAST MARKING OF OBJECTS AND PARTICULARLY LABELS |
US6054006A (en) * | 1997-12-01 | 2000-04-25 | Great Pacific Enterprises, Inc., Through Its Division, Montebello Packaging | Method and apparatus for applying a printed label to a metal container and the labeled container produced thereby |
US6180318B1 (en) | 1999-05-19 | 2001-01-30 | 3M Innovative Properties Company | Method of imaging an article |
FR2833518A1 (en) * | 2001-12-14 | 2003-06-20 | Gemplus Card Int | Carrier for laser-written data e.g. barcodes, comprises a plastic substrate coated with a transparent layer containing a pigment that absorbs light at the wavelengths of the laser |
KR100403212B1 (en) * | 1995-03-16 | 2004-03-19 | 테사 악티엔게젤샤프트 | Multilayer Laser Label and How to Use |
DE19913323B4 (en) * | 1999-03-24 | 2004-03-25 | Cleanpack Gmbh Innovative Verpackungen | Method of making labels |
US20090233067A1 (en) * | 2005-01-10 | 2009-09-17 | Avery Dennison Corporation | Removable curl labels |
WO2010060123A1 (en) * | 2008-11-03 | 2010-06-03 | Teich Aktiengesellschaft | Printed circuit board |
WO2011026106A1 (en) * | 2009-08-31 | 2011-03-03 | 3M Innovative Properties Company | Laser marking process and articles |
US8647721B2 (en) | 2008-11-05 | 2014-02-11 | Exatec, Llc | Part marking of coated plastic substrates |
US9334425B2 (en) | 2009-03-30 | 2016-05-10 | Avery Dennison Corporation | Removable adhesive label containing high tensile modulus polymeric film layer |
US9422465B2 (en) | 2006-11-02 | 2016-08-23 | Avery Dennison Corporation | Emulsion adhesive for washable film |
US10002549B2 (en) | 2009-03-30 | 2018-06-19 | Avery Dennison Corporation | Removable adhesive label containing polymeric film layer having water affinity |
US10157554B2 (en) | 2009-03-30 | 2018-12-18 | Avery Dennison Corporation | Removable adhesive label containing inherently shrinkable polymeric film |
US10687588B2 (en) | 2014-10-22 | 2020-06-23 | 3M Innovative Properties Company | Printed components and methods for making the same |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7485403B2 (en) | 2001-03-16 | 2009-02-03 | Datalase Ltd. | Laser-markable compositions |
US8048605B2 (en) | 2001-03-16 | 2011-11-01 | Datalase Ltd | Laser-markable compositions |
DE202009002784U1 (en) | 2009-02-27 | 2009-05-20 | Dittrich, Alwin | Labeled sheet material and labeling device |
EP3664987B1 (en) * | 2017-08-11 | 2022-08-24 | Husky Injection Molding Systems Ltd. | Molded article, container and a method for printing thereon |
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US4816374A (en) * | 1985-04-12 | 1989-03-28 | Societe D'applications Plastiques Rhone-Alpes (Sapra) | Method of making a plastic material sensitive to laser radiation and enabling it to be marked by a laser, and articles obtained thereby |
US5143570A (en) * | 1985-02-05 | 1992-09-01 | Avery Dennison Corporation | Composite facestocks and liners |
-
1995
- 1995-06-06 AT AT95922091T patent/ATE201318T1/en not_active IP Right Cessation
- 1995-06-06 AU AU26901/95A patent/AU709752B2/en not_active Ceased
- 1995-06-06 DE DE69521045T patent/DE69521045T2/en not_active Expired - Fee Related
- 1995-06-06 EP EP95922091A patent/EP0766546B1/en not_active Expired - Lifetime
- 1995-06-06 WO PCT/US1995/006258 patent/WO1995034263A1/en active IP Right Grant
- 1995-06-06 CA CA002192850A patent/CA2192850A1/en not_active Abandoned
- 1995-06-06 ES ES95922091T patent/ES2157329T3/en not_active Expired - Lifetime
- 1995-06-06 BR BR9508699A patent/BR9508699A/en not_active IP Right Cessation
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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US5143570A (en) * | 1985-02-05 | 1992-09-01 | Avery Dennison Corporation | Composite facestocks and liners |
US4816374A (en) * | 1985-04-12 | 1989-03-28 | Societe D'applications Plastiques Rhone-Alpes (Sapra) | Method of making a plastic material sensitive to laser radiation and enabling it to be marked by a laser, and articles obtained thereby |
Cited By (26)
Publication number | Priority date | Publication date | Assignee | Title |
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KR100403212B1 (en) * | 1995-03-16 | 2004-03-19 | 테사 악티엔게젤샤프트 | Multilayer Laser Label and How to Use |
US6779815B2 (en) | 1997-04-18 | 2004-08-24 | Societe Chevillot S.A. | Forgery proof, indelibly marked label having contrast to aid visibility |
AU725605B2 (en) * | 1997-04-18 | 2000-10-12 | Societe Chevillot S.A. | Method of marking objects, particularly labels, that is impossible to forge, is indelible and has contrast |
FR2762425A1 (en) * | 1997-04-18 | 1998-10-23 | Chevillot Sa | INFALSIFIABLE, INDELEBILE AND CONTRAST MARKING OF OBJECTS AND PARTICULARLY LABELS |
WO1998048398A1 (en) * | 1997-04-18 | 1998-10-29 | Societe Chevillot S.A. | Tamper-resistant, indelible and contrasting method for marking objects, in particular labels |
US6054006A (en) * | 1997-12-01 | 2000-04-25 | Great Pacific Enterprises, Inc., Through Its Division, Montebello Packaging | Method and apparatus for applying a printed label to a metal container and the labeled container produced thereby |
DE19913323B4 (en) * | 1999-03-24 | 2004-03-25 | Cleanpack Gmbh Innovative Verpackungen | Method of making labels |
US6180318B1 (en) | 1999-05-19 | 2001-01-30 | 3M Innovative Properties Company | Method of imaging an article |
FR2833518A1 (en) * | 2001-12-14 | 2003-06-20 | Gemplus Card Int | Carrier for laser-written data e.g. barcodes, comprises a plastic substrate coated with a transparent layer containing a pigment that absorbs light at the wavelengths of the laser |
CN1309579C (en) * | 2001-12-14 | 2007-04-11 | 格姆普拉斯公司 | Laser-marked data medium |
WO2003053709A1 (en) | 2001-12-14 | 2003-07-03 | Gemplus | Laser-marked data medium |
US9387652B2 (en) * | 2005-01-10 | 2016-07-12 | Avery Dennison Corporation | Removable curl labels |
US20090233067A1 (en) * | 2005-01-10 | 2009-09-17 | Avery Dennison Corporation | Removable curl labels |
US10590315B2 (en) | 2006-11-02 | 2020-03-17 | Avery Dennison Corporation | Emulsion adhesive for washable film |
US9422465B2 (en) | 2006-11-02 | 2016-08-23 | Avery Dennison Corporation | Emulsion adhesive for washable film |
WO2010060123A1 (en) * | 2008-11-03 | 2010-06-03 | Teich Aktiengesellschaft | Printed circuit board |
US9254796B2 (en) | 2008-11-05 | 2016-02-09 | Exatec, Llc | Part marking of coated plastic substrates |
US8647721B2 (en) | 2008-11-05 | 2014-02-11 | Exatec, Llc | Part marking of coated plastic substrates |
US9334425B2 (en) | 2009-03-30 | 2016-05-10 | Avery Dennison Corporation | Removable adhesive label containing high tensile modulus polymeric film layer |
US10002549B2 (en) | 2009-03-30 | 2018-06-19 | Avery Dennison Corporation | Removable adhesive label containing polymeric film layer having water affinity |
US10157554B2 (en) | 2009-03-30 | 2018-12-18 | Avery Dennison Corporation | Removable adhesive label containing inherently shrinkable polymeric film |
US10902750B2 (en) | 2009-03-30 | 2021-01-26 | Avery Dennison Corporation | Removable adhesive label containing inherently shrinkable polymeric film |
US8771919B2 (en) | 2009-08-31 | 2014-07-08 | 3M Innovative Properties Company | Laser marking process and articles |
CN102574408A (en) * | 2009-08-31 | 2012-07-11 | 3M创新有限公司 | Laser marking process and articles |
WO2011026106A1 (en) * | 2009-08-31 | 2011-03-03 | 3M Innovative Properties Company | Laser marking process and articles |
US10687588B2 (en) | 2014-10-22 | 2020-06-23 | 3M Innovative Properties Company | Printed components and methods for making the same |
Also Published As
Publication number | Publication date |
---|---|
BR9508699A (en) | 1997-08-12 |
AU709752B2 (en) | 1999-09-09 |
EP0766546B1 (en) | 2001-05-23 |
EP0766546A1 (en) | 1997-04-09 |
AU2690195A (en) | 1996-01-05 |
ATE201318T1 (en) | 2001-06-15 |
DE69521045T2 (en) | 2001-09-06 |
ES2157329T3 (en) | 2001-08-16 |
CA2192850A1 (en) | 1995-12-21 |
EP0766546A4 (en) | 1997-09-03 |
DE69521045D1 (en) | 2001-06-28 |
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