WO2018234643A1 - Photoamorceurs radicalaires et leurs utilisations dans les compositions silicones - Google Patents
Photoamorceurs radicalaires et leurs utilisations dans les compositions silicones Download PDFInfo
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- WO2018234643A1 WO2018234643A1 PCT/FR2018/000177 FR2018000177W WO2018234643A1 WO 2018234643 A1 WO2018234643 A1 WO 2018234643A1 FR 2018000177 W FR2018000177 W FR 2018000177W WO 2018234643 A1 WO2018234643 A1 WO 2018234643A1
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- 0 *Oc(cc1)cc2c1Oc1ccccc1C2=O Chemical compound *Oc(cc1)cc2c1Oc1ccccc1C2=O 0.000 description 1
- GLDOHLZDJTYXNX-UHFFFAOYSA-N CCCCCCCC(C#C)Oc(cc12)ccc1Sc1ccccc1C2=O Chemical compound CCCCCCCC(C#C)Oc(cc12)ccc1Sc1ccccc1C2=O GLDOHLZDJTYXNX-UHFFFAOYSA-N 0.000 description 1
- SKNTWSMWGJYFPA-UHFFFAOYSA-N CCCCCCCCOc(cc12)ccc1Oc1ccccc1C2=O Chemical compound CCCCCCCCOc(cc12)ccc1Oc1ccccc1C2=O SKNTWSMWGJYFPA-UHFFFAOYSA-N 0.000 description 1
- ANDAJDDWUJFOHL-UHFFFAOYSA-N CCCCCCOc(cc12)ccc1OC1=CC=CCC1(C)C2=O Chemical compound CCCCCCOc(cc12)ccc1OC1=CC=CCC1(C)C2=O ANDAJDDWUJFOHL-UHFFFAOYSA-N 0.000 description 1
- BBDIJGWZNUDTHW-UHFFFAOYSA-N CCCCCCOc(cc12)ccc1Sc1ccccc1C2=O Chemical compound CCCCCCOc(cc12)ccc1Sc1ccccc1C2=O BBDIJGWZNUDTHW-UHFFFAOYSA-N 0.000 description 1
- UJKYQUMNQMLPNA-UHFFFAOYSA-N COc(cc1C2=O)ccc1OC1C2=CC=CC1 Chemical compound COc(cc1C2=O)ccc1OC1C2=CC=CC1 UJKYQUMNQMLPNA-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
- C07D311/84—Xanthenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9
- C07D311/86—Oxygen atoms, e.g. xanthones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
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- 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
-
- 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
-
- 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
- B29C64/20—Apparatus for additive manufacturing; Details thereof or accessories therefor
- B29C64/264—Arrangements for irradiation
- B29C64/277—Arrangements for irradiation using multiple radiation means, e.g. micromirrors or multiple light-emitting diodes [LED]
-
- 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
- B29C64/20—Apparatus for additive manufacturing; Details thereof or accessories therefor
- B29C64/295—Heating elements
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
- C07D335/12—Thioxanthenes
- C07D335/14—Thioxanthenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9
- C07D335/16—Oxygen atoms, e.g. thioxanthones
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/28—Treatment by wave energy or particle radiation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- 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
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
Definitions
- the present invention relates to type II photoinitiators for the radical crosslinking of silicone compositions, especially acrylic silicone compositions.
- Another object of the present invention is to provide a radically polymerizable or crosslinkable silicone composition comprising a photoinitiator system. of type II adapted for the crosslinking of silicone compositions, in particular by exposure to radiation, and absorbing a light radiation of wavelength greater than 300 nm.
- the present invention also aims to provide a method for preparing a film or a coating on a substrate from the radical-polymerizable silicone composition according to the invention.
- the silicone compositions with a double crosslinking system have a certain interest for their use in 3D printing because they make it possible to increase the printing speed of silicone elastomeric parts. Irradiation of the layers of silicone compositions as the print is made allows the rapid gelation of part of the composition during production and thus each layer retains its shape without collapsing the printed structure. When the printing is complete, a heating step makes it possible to finish the crosslinking of the composition by polyaddition to obtain a silicone elastomer with good stability and good mechanical properties.
- Patent application WO2016 / 134972 discloses a method for producing a silicone elastomer article with a 3D extrusion or inkjet printer.
- a crosslinked silicone composition both by UV irradiation and by heating.
- the irradiation leads to the gelation of the layers and the final thermal hardening leads to a silicone elastomer with good stability and mechanical properties.
- the only photoinitiator described is a commercial type I photoinitiator Irgacure® 651 which corresponds to 2,2-dimethoxy-2-phenylacetophenone.
- UV radiation with a wavelength of 360 nm is used.
- the composition comprises a type II photoinitiator system which, under the effect of the absorption of the incident light energy, releases free radicals into the medium.
- These radicals act as initiators of radical polymerization of (meth) acrylic functions. Since it is the vector of hardening of the composition, the photoinitiator system is an essential key of this application.
- the silicone composition C1 has the advantage of efficiently crosslinking by exposure to UV or visible radiation.
- the free radical photoinitiator P of formula (I) has the advantage of being more soluble in organopolysiloxanes comprising at least one (meth) acrylate group than commercial free radical initiators such as benzophenone or isopropylthioxanthone.
- Y represents a linear or branched C 1 -C 4 alkylene radical which may be optionally extended by divalent C 1 -C 4 oxyalkylene polyoxyalkylene radicals optionally substituted with a hydroxyl radical;
- a is an integer equal to 0, 1 or 2
- the organopolysiloxane A may have a linear, branched, cyclic or network structure.
- linear organopolysiloxanes these can essentially consist of:
- R 2 represents the monovalent radical of formula Z and the symbols R 1 and R 3 have the same meaning as above.
- H represents the hydrogen atom
- f represents an integer equal to 0, 1, 2 or 3.
- the organohydrogenpolysiloxane H can have a linear, branched, cyclic or network structure.
- linear organohydrogenpolysiloxanes these can essentially consist of:
- siloxyl "M” units chosen from the units of formulas HL 2 SiOi / 2 (also called M 'unit) and L3S1O2 / 2,
- the silicone composition C1 comprises a radical photoinitiator P of formula
- R 1 and R 3 which are identical or different, are chosen from the group consisting of: a hydrogen atom, a hydroxyl and a group of formula -OZ with the symbol O being an oxygen atom and the symbol Z being chosen from the group consisting of:
- R 2 and R 4 are hydrogen atoms
- R 1 and R 3 which are identical or different, are chosen from the group consisting of: a hydrogen atom, a hydroxyl and a group of formula -OZ with the symbol O being an oxygen atom and the symbol Z being chosen from the group consisting of:
- the symbol X is an oxygen atom
- the symbols R 2 and R 4 are hydrogen atoms
- the symbols R 1 and R 3 which are identical or different, are chosen from the group consisting of: a hydrogen atom, a hydroxyl and a group of formula -OZ with the symbol O being an oxygen atom and the symbol Z being chosen from the group consisting of:
- composition C1 as described above,
- W represents independently an alkenyl group, preferably having from 2 to 6 carbon atoms and, more preferably still, a vinyl or allyl group, and
- Organopolysiloxane B may have a branched structure. This is called silicone resin.
- silicone resin comprising from 0.1 to 20% by weight, preferably from 4 to 20% by weight, of C2-C6 alkenyl groups bonded to silicon atoms.
- the alkenyl groups may be located on M, D or T siloxyl units. These resins may be prepared, for example, according to the process described in US Pat. U.S. Patent 2 676 1820.1 at 20%.
- the alkenyl groups are preferably chosen from vinyls, allyls and hexenyls.
- the silicone resin has the formula MD 2 or MIW 2 as described above.
- the catalyst K is platinum-based.
- the weight amount of catalyst K, calculated as weight of platinum-metal is generally between 2 and 400 ppm, preferably between 5 and 200 ppm based on the total weight of the composition C2.
- the silicone compositions C2 may further contain at least one of the following compounds:
- Adhesion promoters G As filler F can be used reinforcing mineral fillers or semi-reinforcing mineral fillers or stuffing.
- the reinforcing mineral fillers may be chosen from siliceous materials.
- the reinforcing siliceous fillers are chosen from colloidal silicas, silica powders of combustion and precipitation or their mixture. These powders have an average particle size generally less than 0.1 ⁇ m and a BET specific surface area greater than 50 m 2 / g, preferably between 150 and 350 m 2 / g. These silicas can be incorporated as such or after being treated with organosilicon compounds usually used for this purpose.
- Conductive fillers such as nano-based graphene or carbon nanotube objects can also be used.
- the silicone composition C2 comprises from 1 to 40 parts by weight of filler F, preferably from 1 to 25 parts by weight of filler F and more preferably from 1 to 15 parts of filler F per 100 parts by weight of silicone composition C2.
- crosslinking inhibitor I (or retarder of the polyaddition reaction) may, for its part, be chosen from the following compounds:
- organopolysiloxane advantageously cyclic, and substituted by at least one alkenyl, tetramethylvinyltetrasiloxane being particularly preferred, phosphines and organic phosphites,
- R 2 is a hydrogen atom, a linear or branched alkyl radical, or a phenyl radical;
- radicals R 1 , R 2 and the carbon atom located alpha of the triple bond may optionally form a ring;
- the total number of carbon atoms contained in R 1 and R 2 being at least 5, preferably from 9 to 20.
- Said alcohols are preferably chosen from those having a boiling point greater than 250 ° C.
- Examples of the following products that are commercially available include:
- Such a crosslinking inhibitor I is present at a maximum of 3000 ppm, preferably at 100 to 2000 ppm relative to the total weight of the composition C2.
- adhesion promoters G it will be possible to use the adhesion promoters usually used in the field. For example, we can use:
- the process for preparing silicone elastomer articles according to the invention may also comprise a heating step, preferably at a temperature of between 60 and 220 ° C., more preferably between 80 and 180 ° C.
- all 3D printing processes have a common starting point, which is a computer-generated data source or program that can describe an object.
- the computer generated data source or program may be based on a real or virtual object. For example, a real object can be scanned using a 3D scanner and the scan data can be used to create the computer generated data source or program. Alternatively, the computer generated data source or program can be designed from scratch.
- the computer generated data source or program is generally converted to a standard language file (STL) format. However, other file formats can be used.
- STL standard language file
- the file is usually read in the 3D printing software, which takes the file and possibly the input of the user to separate it into "slices" whose number can reach several thousand.
- the silicone compositions C2 according to the invention allow to increase the printing speed of the silicone elastomer parts. Irradiation of the layers of silicone compositions as the print is made allows the rapid gelation of part of the composition during production and thus each layer retains its shape without collapsing the printed structure. When the printing is complete, a heating step makes it possible to finish the crosslinking of the composition by polyaddition to obtain a silicone elastomer with good stability and good mechanical properties.
- the silicone compositions C2 according to the invention can be used for 3D printing processes using photopolymerization in the tank, the extrusion of material or the deposition of material by adapting the viscosity of the silicone composition C2 to the technology. employee.
- Photopolymerization in the tank is an additive manufacturing process in which a curable liquid resin present in a tank is selectively cured when the polymerization of its molecular chains is triggered by ultraviolet light.
- In-vat photopolymerization can employ a lamp or light-emitting diodes (LEDs) as a source of UV energy.
- LEDs light-emitting diodes
- the viscosity of the silicone composition C2 will be between 10 mPa.s and 100000 mPa.s, preferably between 100 and 10,000 mPa.s and even more preferably between 100 and 100 mPa.s. and 2000 mPa.s.
- the method further comprises the step of heating the silicone elastomer article obtained by 3D printing. The heating can be used to speed up the treatment.
- the method further comprises the step of further irradiating the silicone elastomer article obtained by 3D printing. Additional irradiation can be used to speed up the treatment.
- the method further comprises the two steps of heating and irradiating the silicone elastomer article obtained by 3D printing.
- post-processing steps can significantly improve the surface quality of printed articles. Sanding is a common way to reduce or eliminate visibly distinct layers of the model.
- Spraying or coating the surface of the elastomeric article with a heat-curable or UV-curable RTV or LSR silicone composition can be used to achieve the appearance of the smooth, straight surface.
- a surface treatment with a laser can also be done.
- sterilization of the final elastomeric article can be obtained by heating the object to a temperature greater than 100 ° C.
- the neodecanoic acid used for the synthesis of photoinitiators is branched with the various acids mentioned above.
- the 1,4-dioxane is evaporated on a rotary evaporator.
- the residue is dissolved with 0% Na 2 CO 3 solution and the solution is filtered.
- the filtrate is then introduced into a separating funnel and is washed with a 50/50 toluene / ethyl acetate mixture.
- the aqueous phase is recovered and acidified before filtering to obtain the reaction intermediate. (Yield: 75%)
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Abstract
Description
Claims
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA3067711A CA3067711A1 (fr) | 2017-06-22 | 2018-06-21 | Photoamorceurs radicalaires et leurs utilisations dans les compositions silicones |
KR1020207001381A KR102458743B1 (ko) | 2017-06-22 | 2018-06-21 | 자유-라디칼 광개시제 및 실리콘 조성물에서 이의 용도 |
BR112019027471-5A BR112019027471B1 (pt) | 2017-06-22 | 2018-06-21 | Composições de silicone, usos das composições, métodos para a preparação de filmes de silicone e para a preparação de artigos, elastômero de silicone, compostos e uso dos compostos |
CN201880052279.4A CN111295379B (zh) | 2017-06-22 | 2018-06-21 | 自由基光引发剂及其在有机硅组合物中的用途 |
JP2019571007A JP6944549B2 (ja) | 2017-06-22 | 2018-06-21 | フリーラジカル光開始剤及びシリコーン組成物におけるその使用 |
EP18750239.8A EP3642192A1 (fr) | 2017-06-22 | 2018-06-21 | Photoamorceurs radicalaires et leurs utilisations dans les compositions silicones |
US16/624,852 US11629233B2 (en) | 2017-06-22 | 2018-06-21 | Free-radical photoinitiators and uses of same in silicone compositions |
US18/159,308 US20230159706A1 (en) | 2017-06-22 | 2023-01-25 | Free-radical photoinitiators and uses of same in silicone compositions |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR1700671 | 2017-06-22 | ||
FR1700671 | 2017-06-22 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US16/624,852 A-371-Of-International US11629233B2 (en) | 2017-06-22 | 2018-06-21 | Free-radical photoinitiators and uses of same in silicone compositions |
US18/159,308 Division US20230159706A1 (en) | 2017-06-22 | 2023-01-25 | Free-radical photoinitiators and uses of same in silicone compositions |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2018234643A1 true WO2018234643A1 (fr) | 2018-12-27 |
Family
ID=60515426
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR2018/000177 WO2018234643A1 (fr) | 2017-06-22 | 2018-06-21 | Photoamorceurs radicalaires et leurs utilisations dans les compositions silicones |
Country Status (7)
Country | Link |
---|---|
US (2) | US11629233B2 (fr) |
EP (1) | EP3642192A1 (fr) |
JP (1) | JP6944549B2 (fr) |
KR (1) | KR102458743B1 (fr) |
CN (1) | CN111295379B (fr) |
CA (1) | CA3067711A1 (fr) |
WO (1) | WO2018234643A1 (fr) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2022189757A1 (fr) * | 2021-03-10 | 2022-09-15 | Elkem Silicones France Sas | Photoamorceur de type i pour la reticulation de compositions silicones |
WO2022240955A1 (fr) | 2021-05-12 | 2022-11-17 | Elkem Silicones USA Corp. | Procédé de production d'un article imprimé tridimensionnel |
WO2022240961A1 (fr) | 2021-05-12 | 2022-11-17 | Elkem Silicones USA Corp. | Procédé de production d'un article imprimé tridimensionnel |
JP2023509653A (ja) * | 2019-12-31 | 2023-03-09 | エルケム・シリコーンズ・シャンハイ・カンパニー・リミテッド | 導電性シリコーンエラストマー物品の製造方法 |
EP4272960A1 (fr) | 2022-05-06 | 2023-11-08 | ELKEM SILICONES France SAS | Procédé de fabrication additive d'un article 3d |
WO2024056948A1 (fr) | 2022-09-15 | 2024-03-21 | Elkem Silicones France Sas | Méthode de fabrication additive pour produire un article en élastomère silicone |
Citations (34)
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US2676182A (en) | 1950-09-13 | 1954-04-20 | Dow Corning | Copolymeric siloxanes and methods of preparing them |
US3159601A (en) | 1962-07-02 | 1964-12-01 | Gen Electric | Platinum-olefin complex catalyzed addition of hydrogen- and alkenyl-substituted siloxanes |
US3159602A (en) | 1962-06-07 | 1964-12-01 | Olin Mathieson | Preparation of polymeric phosphates |
US3220972A (en) | 1962-07-02 | 1965-11-30 | Gen Electric | Organosilicon process using a chloroplatinic acid reaction product as the catalyst |
US3377432A (en) | 1964-07-31 | 1968-04-09 | Bell Telephone Labor Inc | Telephone switching system |
FR1528464A (fr) | 1966-06-23 | 1968-06-07 | Dow Corning | Compositions d'organopolysiloxanes durcissables à une partie composante |
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JP7423790B2 (ja) | 2019-12-31 | 2024-01-29 | エルケム・シリコーンズ・シャンハイ・カンパニー・リミテッド | 導電性シリコーンエラストマー物品の製造方法 |
WO2022189757A1 (fr) * | 2021-03-10 | 2022-09-15 | Elkem Silicones France Sas | Photoamorceur de type i pour la reticulation de compositions silicones |
WO2022240955A1 (fr) | 2021-05-12 | 2022-11-17 | Elkem Silicones USA Corp. | Procédé de production d'un article imprimé tridimensionnel |
WO2022240961A1 (fr) | 2021-05-12 | 2022-11-17 | Elkem Silicones USA Corp. | Procédé de production d'un article imprimé tridimensionnel |
US11964425B2 (en) | 2021-05-12 | 2024-04-23 | Elkem Silicones USA Corp. | Method for producing a three-dimensional printed article |
EP4272960A1 (fr) | 2022-05-06 | 2023-11-08 | ELKEM SILICONES France SAS | Procédé de fabrication additive d'un article 3d |
WO2023213435A1 (fr) | 2022-05-06 | 2023-11-09 | Elkem Silicones France Sas | Procédé de fabrication additive d'un article 3d |
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Also Published As
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KR102458743B1 (ko) | 2022-10-24 |
CN111295379A (zh) | 2020-06-16 |
BR112019027471A2 (pt) | 2020-07-07 |
US20230159706A1 (en) | 2023-05-25 |
KR20200035004A (ko) | 2020-04-01 |
CA3067711A1 (fr) | 2018-12-27 |
US20210332191A1 (en) | 2021-10-28 |
EP3642192A1 (fr) | 2020-04-29 |
BR112019027471A8 (pt) | 2023-04-11 |
CN111295379B (zh) | 2023-08-22 |
JP6944549B2 (ja) | 2021-10-06 |
JP2020524735A (ja) | 2020-08-20 |
US11629233B2 (en) | 2023-04-18 |
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