WO2024061576A1 - Mélange de substances photodurcissable - Google Patents

Mélange de substances photodurcissable Download PDF

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Publication number
WO2024061576A1
WO2024061576A1 PCT/EP2023/073550 EP2023073550W WO2024061576A1 WO 2024061576 A1 WO2024061576 A1 WO 2024061576A1 EP 2023073550 W EP2023073550 W EP 2023073550W WO 2024061576 A1 WO2024061576 A1 WO 2024061576A1
Authority
WO
WIPO (PCT)
Prior art keywords
light
curable
mixture
substance mixture
weight
Prior art date
Application number
PCT/EP2023/073550
Other languages
German (de)
English (en)
Inventor
Gerrit Scholz
Original Assignee
Amann Girrbach Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Amann Girrbach Ag filed Critical Amann Girrbach Ag
Publication of WO2024061576A1 publication Critical patent/WO2024061576A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
    • A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
    • A61K6/887—Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/20—Protective coatings for natural or artificial teeth, e.g. sealings, dye coatings or varnish
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/60—Preparations for dentistry comprising organic or organo-metallic additives
    • A61K6/62—Photochemical radical initiators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/70—Preparations for dentistry comprising inorganic additives
    • A61K6/71—Fillers
    • A61K6/76—Fillers comprising silicon-containing compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/70—Preparations for dentistry comprising inorganic additives
    • A61K6/71—Fillers
    • A61K6/77—Glass
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B33—ADDITIVE MANUFACTURING TECHNOLOGY
    • B33Y—ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING
    • B33Y70/00—Materials specially adapted for additive manufacturing
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B33—ADDITIVE MANUFACTURING TECHNOLOGY
    • B33Y—ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING
    • B33Y80/00—Products made by additive manufacturing
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/70—Preparations for dentistry comprising inorganic additives
    • A61K6/78—Pigments
    • 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
    • B29C64/00—Additive manufacturing, i.e. manufacturing of three-dimensional [3D] objects by additive deposition, additive agglomeration or additive layering, e.g. by 3D printing, stereolithography or selective laser sintering
    • B29C64/10—Processes of additive manufacturing
    • B29C64/106—Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material
    • B29C64/124—Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material using layers of liquid which are selectively solidified
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B33—ADDITIVE MANUFACTURING TECHNOLOGY
    • B33Y—ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING
    • B33Y10/00—Processes of additive manufacturing

Definitions

  • the present invention relates to a light-curable substance mixture and the use of a light-curable substance mixture.
  • Light-curable substance mixtures are of particular importance in two areas of application: in 3D printing processes and in light-curing applications for surface processing.
  • Class 1 medical products include, for example, tray material for impressions or try-ins.
  • Class 2 medical products include, for example, crowns, bridges, splints, drilling templates, complete dentures or teeth for complete dentures. Especially for Class 2 medical products, it is extremely important to prevent the absorption of potentially or actually toxic substances.
  • the light-curing application for surface treatment involves the design, creation and/or repair of objects such as jewelry.
  • a high level of biocompatibility is also necessary in this area, as toxicological risks must be excluded in the event of direct contact with the skin and/or food.
  • Light-curable substance mixtures contain photoinitiators, which are decomposed by the action of UV light and thus generate free radicals. These radicals initiate a polymerization reaction of unsaturated components within the substance mixture.
  • At least one polymer photoinitiator at least one polymer photoinitiator, the polymer photoinitiator having a molecular weight of at least 900 grams/mole, preferably at least 1000 grams/mole.
  • the invention therefore relates to a light-curable mixture of substances in which high-molecular polymer photoinitiators are used.
  • a basic inventive idea is that such polymer photoinitiators have a very low affinity for migration from the cured mixture of substances into the surrounding medium due to their very high molecular weight. This reduces the toxicological risks of the substances used and significantly increases biocompatibility.
  • light-curable substance mixtures according to the invention have a very low yellow discoloration and a high color stability.
  • Further positive properties of light-curable material mixtures according to the invention are favorable mechanical properties, a good depth of curing and rapid curing.
  • An ethylenically unsaturated component is a component with at least one carbon-carbon double bond.
  • a photoinitiator is a light-sensitive molecule that, when exposed to light, forms a reactive species that initiates a reaction.
  • the invention involves a light-induced or photoinduced reaction is a polymerization reaction, that is, a polymerization, a polyaddition and/or a polycondensation.
  • Polymer photoinitiators include, for example, the following two molecules, the structures of which are shown below: Tri(phenyl (2, 4, 6-trimethylbenzoyl) phosphinic acid) polyethylene glycol ester or Di ⁇ (ß-4[4-(2-dimethylamino-2-benzyl) butaonylphenyl ] piperazine) propane acid ⁇ polyethylene glycol ester . These are examples only and should not be construed as limiting.
  • the number of individual monomer units for a+b+c ranges from 1 to 30, in particular from 2 to 20.
  • the number of individual monomer units for n ranges from 1 to 20, preferably from 2 to 10.
  • the polymer photoinitiator has a molecular weight of at least 1200 grams/mol, preferably of at least 1500 grams/mol, particularly preferably of at least 2000 grams/mol.
  • the mass fraction of filler f in the light-curable substance mixture is from 0 to 70% by weight! , preferably from 2 to 40 weight! having .
  • the mass fraction of filler f in the light-curable material mixture is from 0 to 50% by weight! , preferably from 0 to 30 weight! , having .
  • the light-curable substance mixture has at least one ethylenically unsaturated component with a mass fraction of 15 to 95% by weight! and at least one polymer photoinitiator with a mass fraction of 0.3 to 10 by weight! on .
  • the light-curable substance mixture may or may not also contain at least one filler and/or at least one pigment and/or at least one additive. If at least one filler f is present, it can have a mass fraction of up to 85% by weight! on the light-curable substance mixture. If at least one pigment is present, so its mass fraction of the light-curable substance mixture can be up to 10% by weight! amount. If at least one additive is present, its mass fraction of the light-curable substance mixture can also be up to 10% by weight! amount.
  • the absence of a pigment can provide a colorless and/or transparent mixture of substances.
  • At least one pigment is also present in the light-curable substance mixture in addition to the at least one ethylenically unsaturated component and the at least one polymer photoinitiator, white, red, black or other pigments can be provided, for example.
  • a suitable recipe and the use of polymer photoinitiators can provide favorable mechanical properties of the cured mixture of substances.
  • the light-curable substance mixture has a 3-point bending strength of 70 megapascals to 130 megapascals after curing, with the 3-point bending strength for non-medical products being determined according to the DIN EN ISO 178 standard and the 3-point bending strength for medical products according to DIN EN ISO 20795-1 for, for example, complete dentures, fittings or individual impression trays, according to the DIN EN ISO 20795-2 standard for, for example, splints or drilling templates and according to the DIN EN ISO 10477 standard for crowns or bridges, for example.
  • the light-curable substance mixture has a Shore D hardness of 80 to 98, preferably 92 to 97, after curing. It can be provided that the light-curable substance mixture is processed with an accuracy of 20 gm to 150 gm after curing.
  • the polymer photoinitiator is an oligomeric polyol ester, preferably a
  • phosphinic acid polyethylene glycol ester or a piperazine-based aminoalkylphenone.
  • (phosphinic acid) polyethylene glycol ester can be understood to mean phosphinic acid polyethylene glycol ester.
  • the polymer photoinitiator has or consists of a simple molecular chain or a multi-branched molecular chain.
  • the branched molecular chain can have at least three chain ends, preferably four chain ends.
  • the polymer photoinitiator has or consists of a multi-branched molecular chain and the multi-branched molecular chain has at least three chain ends, preferably four chain ends
  • the polymer photoinitiator can have or consist of at least one dendrimer.
  • the light-curable substance mixture is mixed with a UV light is curable in the wavelength range from 320 nanometers to 500 nanometers, preferably in the wavelength range from 350 nanometers to 420 nanometers.
  • the light-curable material mixture can be cured with UV light in the wavelength range from 350 nanometers to 420 nanometers.
  • the light-curable substance mixture at room temperature before curing has a viscosity in the range from 0.05 pascal seconds to 5000 pascal seconds, preferably in the range from 0.05 pascal seconds to 10 pascal seconds.
  • the light-curable mixture of substances can have a viscosity in the range of 0.05 to 5000 Pascal seconds at room temperature before curing.
  • the light-curable substance mixture preferably has a viscosity in the range of 0.05 to 10 pascal seconds, preferably 0.2 - 2 pascal seconds, at room temperature before curing.
  • the at least one ethylenically unsaturated component has or consists of at least one monomer, an oligomer or a polymer.
  • the at least one ethylenically unsaturated component is at least one (meth)acrylate and/or
  • (Meth)acrylate can be understood as acrylate or methacrylate.
  • Epoxy (meth)acrylate can be understood as epoxy acrylate or epoxy methacrylate.
  • (meth)acrylated can be understood as acrylated or methacrylated.
  • the filler f is silicon dioxide and/or barium oxide and/or strontium oxide and/or glass powder and/or ceramic powder and/or zirconium oxide and/or zinc oxide and/or titanium dioxide and/or aluminum oxide and/or Has or is hydroxyapatite and/or a prepolymerized filler.
  • the additive has or consists of a UV absorber and/or a rheological agent and/or an inhibitor and/or an adhesion promoter and/or a stabilizer.
  • a rheological agent prevents sedimentation within the light-curable material mixture.
  • An inhibitor serves to control the reaction rate and thus reaction control.
  • An adhesion promoter improves the adhesion of a light-curable substance mixture to a substrate after curing.
  • the invention also relates to the use of a light-curable substance mixture according to the invention for producing a dental component in a 3D printing process, in particular for the dental sector.
  • a light-curable substance mixture according to the invention for surface processing of a metal and/or a metal alloy and/or a rock and/or a ceramic and/or a tile and/or a decorative item.
  • Fig. 1 a schematic exemplary embodiment of a 3D printing structure with a light-curable material mixture
  • FIG. 2 the exemplary embodiment from FIG. 1 with a laser Fig. 3 Bottom view of the tub from Fig. 2
  • FIG. 4 the exemplary embodiment from FIG. 1 with a light source and a cover
  • FIG. 5 the exemplary embodiment from FIG. 1 with a projector
  • FIG. 6 Bottom view of the tub from Fig. 4 and Fig. 5 Fig. 7 to 10 a schematic exemplary embodiment and a process of surface processing with a light-curable substance mixture
  • Fig. 1 shows a schematic exemplary embodiment of a 3D printing structure with a light-curable material mixture 1.
  • the light-curable substance mixture 1 is located in a trough 10.
  • the light-curable substance mixture 1 contains an ethylenically unsaturated component 2 as the basic component.
  • Further components of the light-curable material mixture 1 are fillers 3, pigments 4, additives 5 and a polymer photoinitiator 6. These individual components of the light-curable substance mixture 1 are shown in FIG. l only shown symbolically and are no longer shown explicitly in all other figures for reasons of clarity.
  • the 3D printed product 7 to be produced is a dental product, specifically a dental splint, which is connected to a movable platform 9.
  • support structures 8 are necessary between the toothed rail and the movable platform 9.
  • Such support structures 8 are known in the field of 3D printing and are separated from the toothed splint after it has been completed.
  • the movable platform 9 can move up and down in the vertical direction, specifically in the directions P. The directions of movement of the movable platform 9 are not limited to this exemplary embodiment.
  • the toothed rail connected to it can be inserted into the light-curable substance mixture 1 can be lowered and lifted out again.
  • Fig. 2 shows the exemplary embodiment from FIG. 1 with a laser 11.
  • the movable platform 9 together with the support structure 8 and the dental splint were lowered into the light-curable material mixture 1 in the tank 10.
  • the light-curable substance mixture 1 can be hardened selectively with respect to one or more desired contours and/or surfaces and thus form newly hardened layers 14.
  • the laser 11 generates a laser beam 12 which impinges on a movable mirror 13.
  • the laser beam 12 can selectively trace the desired contours and/or surfaces as newly hardened layers 14 on the toothed rail 7 and thus harden them.
  • the movable mirror 13 can be controlled electronically, with all common technologies such as CAD/CAM being used.
  • the laser beam 12 penetrates the bottom of the tub 10 and strikes a point on the lower edge of the dental splint or, more generally, the 3D printed product 7.
  • the bottom of the tub 10 must be sufficiently translucent in the required areas.
  • the light-curable substance mixture 1 is thus cured by the laser beam 12 between the bottom of the tub 10 and the dental splint, and therefore also on the dental splint.
  • a newly cured layer 14 is created on the left-hand side of the dental splint, as shown in Fig. 2.
  • Such an SLA process stereolithography apparatus
  • Stereolithography is a very precise process.
  • the laser beam 12 achieves a high resolution of the newly hardened layer 14, which hardens point by point.
  • Fig. 3 shows a bottom view of the tub 10 from Fig. 2.
  • the tub 10 contains the light-curable material mixture 1.
  • the part of the dental splint or, more generally, the 3D-printed product 7 that has already been produced can be seen when viewed from below.
  • a laser beam 12 has formed a new hardened layer 14 and has already hardened half of the left side of the lower edge of the dental splint.
  • the left part of the dental splint is hardened across the surface, following the contour.
  • the right part of the dental splint is then hardened in the same way to produce two complete, newly hardened layers 14.
  • Fig. 4 shows the exemplary embodiment from FIG. 1 with a light source 15 and an aperture 17.
  • the movable platform 9 together with the support structure 8 and the toothed rail or Generally speaking, the 3D printed product 7 is lowered into the light-curable substance mixture 1 in the tub 10.
  • a wide-area light source 15 is used here instead of a laser 11.
  • the wide-area lamp 15 radiates a wide cone of light 16 towards the transparent bottom of the tub 10.
  • the base must be transparent to the light 16 of the lamp 15 so that the light can be hardened Mixture of substances 1 can harden in the tub 10.
  • the light source 15 in this exemplary embodiment is preferably a light-emitting diode (LED).
  • the cover 17 can preferably be a digital cover, in particular an LCD screen. Light from the wide light cone 16 is only allowed to pass through the cover 17 at those positions where a new hardened layer 14 is to be created.
  • Fig. 5 shows the exemplary embodiment from Fig. 1 with a projector 15.
  • the movable platform 9 together with the support structure 8 and the toothed rail or Generally speaking, the 3D printed product 7 is lowered into the light-curable substance mixture 1 in the tub 10.
  • a light projector 15 is used, which can selectively illuminate one or more contours and/or surfaces at the same time.
  • a light projector 15 can preferably be a digital projector.
  • a digital projector can also be used which enables functionality based on DLP technology (Digital Light Processing).
  • the movement of the movable plate 9 causes new hardened layers 14 made of the light-curable substance mixture 1 to harden under constant and static irradiation.
  • the directions of movement of the movable platform 9 necessary for this are at right angles to the direction of irradiation. In other words, this means that the platform 9 can be designed to be movable.
  • Fig. 6 shows a bottom view of the tub 10 from Figs. 4 and 5.
  • Fig. 7 to 10 shows a schematic exemplary embodiment and the process of surface processing with a light-curable substance mixture 1.
  • Fig. 7 shows damage on a surface 18.
  • the surface 18 can consist of a wide variety of materials, for example a metal, a metal alloy, a rock and/or a ceramic and/or can, for example, be part of a tile or a decorative item.
  • the damage on the surface 18 in this case is an inwardly oriented dent.
  • Fig. 8 shows the damaged surface from Fig. 7 and an applicator 19, with the help of which a light-curable substance mixture 1 according to the invention can be applied.
  • Fig. 9 shows the light-curable substance mixture 1 applied to the damaged area, which is cured by a light source 15.
  • Fig. 10 shows the previously damaged surface, which has now been repaired.
  • the repaired area 20 contains the already cured substance mixture 1, which, for example, after grinding and/or polishing, is flush with the rest of the surface.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Materials Engineering (AREA)
  • Plastic & Reconstructive Surgery (AREA)
  • Biophysics (AREA)
  • Dental Preparations (AREA)

Abstract

L'invention concerne un mélange de substances photodurcissable (1) comprenant : de 15 à 95 % en poids d'au moins un composant éthyléniquement insaturé (2), de 0 à 85 % en poids d'au moins une matière de charge (3), de 0 à 10 % en poids d'au moins un pigment (4), de 0 à 10 % en poids d'au moins un additif (5) et de 0,3 à 10 % en poids d'au moins un photoamorceur polymère (6), le photoamorceur polymère (6) ayant un poids moléculaire d'au moins 900 g/mol, de préférence d'au moins 1000 g/mol.
PCT/EP2023/073550 2022-09-19 2023-08-28 Mélange de substances photodurcissable WO2024061576A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102022123995.0 2022-09-19
DE102022123995.0A DE102022123995A1 (de) 2022-09-19 2022-09-19 Lichthärtbares Stoffgemisch

Publications (1)

Publication Number Publication Date
WO2024061576A1 true WO2024061576A1 (fr) 2024-03-28

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PCT/EP2023/073550 WO2024061576A1 (fr) 2022-09-19 2023-08-28 Mélange de substances photodurcissable

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DE (1) DE102022123995A1 (fr)
WO (1) WO2024061576A1 (fr)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2420117A (en) * 2004-11-10 2006-05-17 Sun Chemical Ltd Piperazino based multi-functional photoinitiators
WO2018104213A1 (fr) * 2016-12-09 2018-06-14 Sicpa Holding Sa Encres d'impression offset et typographique durcissables à faible énergie et procédé d'impression

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3289029B1 (fr) 2015-05-01 2022-02-23 Sun Chemical Corporation Composition d'encre ou de revêtement durcissable par de l'énergie et électriquement isolante
KR20180120206A (ko) 2016-02-25 2018-11-05 벨록스-퓨어디지털 리미티드. 인쇄 제제 및 방법
US11584817B2 (en) 2018-06-29 2023-02-21 3M Innovative Properties Company Orthodontic articles comprising cured free-radically polymerizable composition with improved strength in aqueous environment

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2420117A (en) * 2004-11-10 2006-05-17 Sun Chemical Ltd Piperazino based multi-functional photoinitiators
WO2018104213A1 (fr) * 2016-12-09 2018-06-14 Sicpa Holding Sa Encres d'impression offset et typographique durcissables à faible énergie et procédé d'impression

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
ARMAN KANDIRMAZ EMINE ET AL: "Preparation of novel thioxanthone based polymeric photoinitiator for flexographic varnish and determination of their migration behaviour", PROCESS IN ORGANIC COATINGS, vol. 119, 1 June 2018 (2018-06-01), NL, pages 36 - 43, XP093106119, ISSN: 0300-9440, Retrieved from the Internet <URL:https://www.sciencedirect.com/science/article/pii/S0300944017301674/pdfft?md5=2ffb014172198fee4e01aa8d38902170&pid=1-s2.0-S0300944017301674-main.pdf> [retrieved on 20231128], DOI: 10.1016/j.porgcoat.2018.02.012 *

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