Classifications

• • 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
  • C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
  • C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
  • C08F299/08—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polysiloxanes
• • 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
  • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
  • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
  • C08F290/06—Polymers provided for in subclass C08G
  • C08F290/068—Polysiloxanes
• • 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
  • C08G77/06—Preparatory processes
  • C08G77/08—Preparatory processes characterised by the catalysts used
• • 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
  • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
  • C08G77/442—Block-or graft-polymers containing polysiloxane sequences containing vinyl polymer sequences
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D11/00—Inks
  • C09D11/02—Printing inks
  • C09D11/10—Printing inks based on artificial resins
  • C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D11/00—Inks
  • C09D11/30—Inkjet printing inks
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D183/00—Coating compositions based on 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; Coating compositions based on derivatives of such polymers
  • C09D183/04—Polysiloxanes
• • 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

Definitions

• the present invention relates to a curable composition and an ink jet ink, and more particularly to a curable composition and an ink jet ink having good inkjet ejection properties and capable of both radical curing by ultraviolet irradiation and additional curing by heating. ..
• Inkjet ejection is an effective coating method for forming a thin film on a substrate.
• polydimethylsiloxane is not suitable for inkjet ejection because of its low surface tension, but acrylic-modified polysiloxane, whose surface tension is improved by substituting a long-chain alkyl group on the silicon atom, has good inkjet ejection.
• Patent Document 1 Patent Document 1
• Acrylic-modified polysiloxane is mixed with a photoinitiator and irradiated with ultraviolet rays to cleave the photoinitiator to generate active radicals, and the acrylic group is radically polymerized to promote curing.
• Curing proceeds instantaneously with ultraviolet irradiation, but the life of radicals is short, and in principle it is not possible to further cure by performing post-cure such as heating after ultraviolet irradiation. Further, when oxygen coexists during curing, there is a problem that curing inhibition occurs.
• the present invention has been made in view of the above circumstances, and an object of the present invention is to provide a curable composition and an ink for inkjet, which have good inkjet ejection properties and are capable of both radical curing and addition curing. ..
• the present inventors have obtained a (meth) acrylic functional organohydrogenpolysiloxane having a hydrosilyl group and an alkyl group in one molecule, a photopolymerization initiator and hydrosilylation.
• a curable composition containing a reaction catalyst and having a predetermined surface tension and viscosity has good inkjet ejection properties and is capable of both radical curing with a (meth) acrylic group and addition curing by hydrosilylation.
• the (meth) acrylic functionality means that it contains an acryloyloxyalkyl group or a methacryloyloxyalkyl group.
• R 1 independently represents a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms
• R 2 independently represents a substituted or unsubstituted alkyl group or aryl group, respectively.
• R 3 independently represents a hydrogen atom or a methyl group
• Me represents a methyl group
• m independently represents an integer of 1 to 10
• a and b are independent of each other. Therefore, a + b represents an integer of 1 or more, and a + b is an integer of 3 to 120.
• each siloxane unit in parentheses with a and b may be arbitrary.
• Inkjet ink which comprises the curable composition according to 1 or 2.
• 4. A cured product obtained by curing the curable composition according to 1 or 2 is provided.
• the curable composition of the present invention has good inkjet ejection properties, has addition curability with a SiH group as a reaction point for hydrosilylation, and has radical curability with a (meth) acrylic group as a reaction point. , Coating agents, sealants, adhesives, modeling materials for 3D printers, etc.
• the curable composition of the present invention is (A) Organopolysiloxane represented by the following formula (1), (B) Photopolymerization initiator and (C) Contains a hydrosilylation reaction catalyst.
• the component (A) of the present invention is an organopolysiloxane represented by the following formula (1).
• R 1 independently represents a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms
• R 2 independently represents a substituted or unsubstituted alkyl group or aryl group, respectively.
• R 3 independently represents a hydrogen atom or a methyl group
• Me represents a methyl group
• m independently represents an integer of 1 to 10
• a and b are independent of each other. Therefore, a + b represents an integer of 1 or more, and a + b is an integer of 3 to 120.
• the arrangement of each siloxane unit in parentheses with a and b may be arbitrary.
• the substituted or unsubstituted alkyl group having 1 to 8 carbon atoms of R 1 may be linear, branched or cyclic, and specific examples thereof include methyl, ethyl, n-propyl, isopropyl and n-. Examples thereof include butyl, isobutyl, tert-butyl, n-hexyl, cyclohexyl, n-octyl, 2-ethylhexyl group and the like.
• halogen atoms such as chlorine, fluorine and bromine, such as 3-chloropropyl, 3,3,3-trifluoropropyl groups and the like. It may be a halogen-substituted alkyl group.
• linear alkyl groups such as methyl, ethyl, n-propyl, n-butyl, n-hexyl, and n-octyl groups are preferable, and unreacted components can be easily removed and the surface tension is improved.
• Alkyl groups having 1 to 6 carbon atoms, particularly 3 to 6 are more preferable, and n-propyl groups are most preferable.
• the substituted or unsubstituted alkyl group of R 2 may be linear, branched or cyclic, and those having 1 to 8 carbon atoms are preferable, and specific examples thereof are methyl, ethyl and n-propyl. , Isopropyl, n-butyl, isobutyl, tert-butyl, n-hexyl, cyclohexyl, n-octyl, 2-ethylhexyl group and the like.
• chloromethyl, 3-chloropropyl, 3,3,3-trifluoropropyl in which some or all of the hydrogen atoms bonded to the carbon atoms of these alkyl groups are replaced with halogen atoms such as chlorine, fluorine and bromine.
• halogen atoms such as chlorine, fluorine and bromine.
• examples thereof include halogen-substituted alkyl groups such as groups.
• the substituted or unsubstituted aryl group preferably has 6 to 20 carbon atoms, and specific examples thereof include a phenyl group and a tolyl group.
• halogen-substituted aryl groups such as chlorophenyl and fluorophenyl groups in which some or all of the hydrogen atoms bonded to the carbon atoms of these aryl groups are substituted with the same halogen atoms as described above can be mentioned.
• an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 10 carbon atoms is preferable, and a methyl group is more preferable.
• a represents an integer of 1 or more, preferably 1 to 60, more preferably 1 to 30, still more preferably an integer of 3 to 20, and b represents an integer of 1 or more, preferably 1 to 60, It is more preferably an integer of 1 to 30, still more preferably 3 to 20, a + b is an integer of 3 to 120, preferably 3 to 80, and particularly preferably an integer of 6 to 20.
• m is an integer of 1 to 10, preferably an integer of 1 to 5, and particularly preferably an integer of 2 to 4. If m exceeds 10, it becomes difficult to remove unreacted disiloxane during synthesis.
• the arrangement of each siloxane unit in the formula (1) may be arbitrary, and may be random, block, alternate, or the like.
• the component (meth) acrylic functional organopolysiloxane preferably has a surface tension of 23 to 30 mN / m at 23 ° C. and a viscosity of 5 at 23 ° C. It is preferably about 80 mPa ⁇ s.
• the surface tension is a value measured using an automatic surface tension meter CBVP-Z manufactured by Kyowa Interface Science Co., Ltd.
• the viscosity is a value measured using a rotary viscometer manufactured by Toki Sangyo Co., Ltd.
• the component (A) is, for example, a cyclic organohydrogenpolysiloxane represented by the following general formula (2-1), a cyclic organohydrogenpolysiloxane represented by the following general formula (2-2), and the following general formula. It can be obtained by reacting a mixture of cyclic dimethylpolysiloxane represented by (2') with disiloxane represented by the following general formula (3) in the presence of Bronsted acid.
• R 1 is as described above.
• A1 and b1 each independently represent an integer of 1 to 7, and a1 + b1 represent an integer of 3 to 8.
• Each siloxane unit in parentheses. The arrangement of is arbitrary.
• c1 represents an integer of 3 to 10.
• R 2 , R 3 and m are as described above.
• a1 and b1 are independently integers of 1 to 7, preferably 1 to 4, and more preferably 1 to 3.
• a1 + b1 is an integer of 3 to 8, preferably an integer of 3 to 7, and more preferably an integer of 3 to 5.
• a cyclic siloxane having a1 + b1 of less than 3 may be difficult to synthesize, and if it exceeds 8, it may be difficult to remove the unreacted cyclic organohydrogenpolysiloxane.
• the ratio of b1 / (a1 + b1) is preferably 0.25 to 0.5 from the viewpoint of ring-opening polymerization reactivity and surface tension of the obtained polysiloxane.
• the arrangement of each siloxane unit in the formula (2-1) may be arbitrary, and may be random, block, alternate, or the like.
• c1 is preferably an integer of 4 to 8, more preferably an integer of 4 to 6.
• cyclic organohydrogenpolysiloxane represented by the formula (2-1) include 2,4,6,8-tetramethylcyclotetrasiloxane, 2,2,4,6,6,8-. Hexamethylcyclotetrasiloxane, 2,4,6,8-tetramethyl-2-n-propylcyclotetrasiloxane, 2,4,6,8-tetramethyl-2,4-di-n-propylcyclotetrasiloxane, 2,4,6,8-Tetramethyl-2,6-di-n-propylcyclotetrasiloxane, 2,4,6,8-tetramethyl-2,4,6-tri-n-propylcyclotetrasiloxane, etc. Can be mentioned.
• 2,4,6,8-tetramethyl-2,4-di-n-propylcyclotetrasiloxane 2,4,6,8-tetramethyl-2,6-di-n-propylcyclotetra Siloxane is preferred.
• the compound of the formula (3) include, for example. 1,3-bis (acryloyloxymethyl) tetramethyldisiloxane, 1,3-bis (methacryloyloxymethyl) tetramethyldisiloxane, 1,3-bis (acryloyloxypropyl) tetramethyldisiloxane, Examples thereof include 1,3-bis (methacryloyloxypropyl) tetramethyldisiloxane.
• the amount of the compound used is such that the values of a and b in the obtained organopolysiloxane represented by the formula (1) are in the above range, and the amounts of the compounds a1 and b1 in the compound of the formula (2-1) which are the raw materials are in the above range. It can be adjusted by the number and the molar ratio of the compounds of the formulas (2-1) and (3) in the ring-opening polymerization reaction. Further, it is adjusted by the number of a1 of the formula (2-2) and c1 of the formula (2') and the molar ratio of the compounds of the formulas (2-2), (2') and (3) in the ring-opening polymerization reaction. be able to.
• Bronsted acids include concentrated hydrochloric acid, concentrated sulfuric acid, concentrated nitrate, trifluoroacetic acid, methanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, p-nitrobenzenesulfonic acid, 1,1,1- Examples thereof include trifluoro-N-[(trifluoromethyl) sulfonyl] methanesulfonamide.
• concentrated hydrochloric acid and concentrated sulfuric acid from the viewpoint of compatibility between the cyclic organohydrogenpolysiloxane represented by the general formula (2-1) and the disiloxane represented by the general formula (3).
• Trifluoroacetic acid, methanesulfonic acid, trifluoromethanesulfonic acid are preferable.
• the amount of Bronsted acid added is the cyclic organohydrogenpolysiloxane represented by the above general formula (2-1) or the general formulas (2-2) and (2') in consideration of the reaction time and the neutralization step. 0.01 to 2 parts by mass is preferable with respect to 100 parts by mass in total of the siloxane and the disiloxane represented by the general formula (3).
• the polymerization may be carried out in a solvent-free system or by using an organic solvent such as toluene. Further, in order to prevent gelation during polymerization, an antioxidant such as dit-butylhydroxytoluene may be added.
• the polymerization may be carried out under known conditions, preferably at 50 to 100 ° C. for 1 to 24 hours.
• the component (B) of the present invention is a photopolymerization initiator.
• the photopolymerization initiator include 2,2-diethoxyacetophenone, 2,2-dimethoxy-1,2-diphenylethane-1-one (Omnirad 651), 1-hydroxy-cyclohexyl-phenyl-ketone (Omnirad 184), and the like.
• the amount of the photopolymerization initiator added is not particularly limited, but is preferably 0.01 to 20 parts by mass, preferably 0.1 to 20 parts by mass, based on 100 parts by mass in total of the component (A) and any component (D) described later. 10 parts by mass is more preferable. If it is less than 0.01 parts by mass, the curability of the composition may be insufficient, and if it exceeds 20 parts by mass, the amount of weight loss during curing may be large and the mechanical properties after curing may be deteriorated. ..
• the component (C) of the present invention is an addition reaction with a (meth) acrylic group in the above component (A), a (meth) acrylic group in the component (D) described later, and a hydrosilyl group in the component (A).
• It is a hydrosilylation reaction catalyst for accelerating the above, and a well-known catalyst can be mentioned as a catalyst used for the hydrosilylation reaction.
• a well-known catalyst can be mentioned as a catalyst used for the hydrosilylation reaction.
• platinum group metal-based catalysts for example, platinum group metals such as platinum (including platinum black), rhodium, and palladium; H 2 PtCl 4 ⁇ nH 2 O, H 2 PtCl 6 ⁇ nH.
• the amount of the hydrosilylation reaction catalyst added is not limited as long as it promotes curing (hydrosilylation reaction) of the present composition, with respect to a total of 100 parts by mass of the component (A) and any component (D) described later.
• the amount is preferably 0.01 to 20 parts by mass, more preferably 0.1 to 10 parts by mass (particularly, the amount of the platinum group metal atom in this component is 0.01 to 500 ppm in terms of mass, and more preferably. Is an amount of 0.05 to 100 ppm, more preferably 0.01 to 50 ppm). If it is less than 0.01 parts by mass, the curability of the composition may be insufficient, and if it exceeds 20 parts by mass, the storage stability may be deteriorated and the curable composition may be thickened.
• the component (D) is a monofunctional or polyfunctional (meth) acrylate compound containing no siloxane structure, and can be used as a reactive diluent or a surface tension improver by mixing with the component (A).
• Examples of the monofunctional (meth) acrylate compound containing no siloxane structure include isoamyl acrylate, lauryl acrylate, stearyl acrylate, ethoxy-diethylene glycol acrylate, methoxy-triethylene glycol acrylate, 2-ethylhexyl-diglycol acrylate, phenoxyethyl acrylate, and phenoxydiethylene glycol.
• Examples thereof include acrylate, tetrahydrofurfuryl acrylate, isobornyl acrylate, and a mixture thereof, and isobornyl acrylate is particularly preferable.
• Examples of the polyfunctional (meth) acrylate compound containing no siloxane structure include triethylene glycol diacrylate, polytetramethylene glycol diacrylate, neopentyl glycol diacrylate, 1,6-hexanediol diacrylate, and dimethylol-tricyclodecanediacrylate. , Trimethylolpropantriacrylate, pentaerythritol tetraacrylate, a mixture thereof and the like, and dimethylol-tricyclodecanediacrylate is particularly preferable.
• the (meth) acrylate compound of the component (D) may be used alone or in combination of two or more types, and when the component (D) is used, the amount added is the viscosity of the composition and the surface. From the viewpoint of tension and curing shrinkage, 0.1 to 100 parts by mass is preferable, 5 to 100 parts by mass is more preferable, and 10 to 50 parts by mass is more preferable with respect to 100 parts by mass of the component (A). is there.
• the curable composition of the present invention contains other components exemplified below as long as the object of the present invention is not impaired. May be good.
• the curable composition of the present invention can contain a compound (hydrosilylation reaction control agent) having an effect of suppressing and controlling an addition curing reaction.
• a compound hydrosilylation reaction control agent
• a conventionally known compound can be used.
• phosphorus-containing compounds such as triphenylphosphine
• compounds containing nitrogen atoms such as tributylamine, tetramethylethylenediamine and benzotriazole
• compounds containing sulfur atoms such as tributylamine, tetramethylethylenediamine and benzotriazole
• acetylene compounds such as acetylene alcohols
• hydro Peroxy compounds maleic acid derivatives and the like can be mentioned.
• Other components include a cross-linking agent having a hydrosilyl group for enhancing addition curability, an adhesive-imparting agent for a substrate such as a silane coupling agent, an antioxidant and a light stabilizer; metal oxide, metal water. Examples thereof include heat resistance improvers such as oxides and dyes for coloring.
• the curable composition of the present invention can be obtained by stirring and mixing the components (A), (B), (C), and if necessary, the component (D) and other components by a conventional method.
• the device used for operations such as stirring is not particularly limited, but a grinder, a three-roll, a ball mill, a planetary mixer, or the like can be used. Moreover, you may combine these devices as appropriate.
• the surface tension of the composition at 23 ° C. is preferably 23 to 30 mN / m, preferably 23 to 28 mN / m, and the viscosity at 23 ° C. is a guideline for inkjet ejection. It is 5 to 80 mPa ⁇ s, preferably 8 to 70 mPa ⁇ s. Within these ranges, stable inkjet ejection can be performed, and the composition of the present invention can be suitably used as an inkjet ink. The method for measuring the viscosity of the composition is as described later.
• the curing conditions of the curable composition of the present invention can be, for example, 25 ° C. for 1 to 24 hours, but it can also be heated to 40 to 120 ° C. to promote curing.
• examples of the light source of the ultraviolet rays to be irradiated include UV LED lamps, high-pressure mercury lamps, ultra-high pressure mercury lamps, metal halide lamps, carbon arc lamps, xenon lamps and the like. ..
• the irradiation amount (integrated light amount) of ultraviolet rays is preferably 1 to 5,000 mJ / cm 2 and more preferably 10 to 10 to a sheet obtained by molding the composition of the present invention into a thickness of about 2.0 mm.
• UV rays having an illuminance of 100 mW / cm 2 are used, the ultraviolet rays may be irradiated for about 0.01 to 50 seconds. Further, these curing methods may be combined, and for example, post-curing by heating after irradiation with ultraviolet rays can be performed to further promote curing.
• the curable composition of the present invention can be applied to various substrates and can also be used as a coating or an adhesive.
• the base material those used in the fields of coating, bonding and sealing of casings or members such as composite materials, metal members, plastic members or ceramic members, electrical applications, electronic applications and optical applications can be used.
• Mn and Mw by gel permeation chromatography are standard polystyrene-equivalent values using HLC-8320 GPC manufactured by Tosoh Corporation. 1 1 H-NMR was measured using a nuclear magnetic resonance apparatus manufactured by JEOL Ltd. Further, in the following formula, Me represents a methyl group and n-Pr represents an n-propyl group.
• Examples 1 to 4 Comparative Examples 1 to 6
• a curable composition was prepared according to a conventional method with the compositions shown in Table 1 below.
• the components used in the examples and comparative examples are as follows.
• formulas (5)-(7) and (10) the sequence of each siloxane unit in parentheses is random, alternating or blocking.
• the obtained curable composition was evaluated by the following method. The results are shown in Table 1.
• ⁇ viscosity The viscosity was measured at 23 ° C. using a rotary viscometer manufactured by Toki Sangyo Co., Ltd.
• ⁇ surface tension ⁇ The surface tension was measured at 23 ° C. using an automatic surface tension meter CBVP-Z type manufactured by Kyowa Interface Science Co., Ltd.
• Inkjet ejection property For the inkjet ejection property, a camera is used to capture the ejection state under the ejection conditions of a frequency of 10 kHz, a head temperature of 23 ° C. It was evaluated by taking a picture with.
• the radical curability is determined by weighing 0.5 g of a liquid curable composition on an aluminum mast to form a liquid film having a thickness of about 300 ⁇ m, and then using a UV-LED lamp having a peak wavelength of 365 nm and using 365 nm light as an index.
• the evaluation was made by irradiating each composition with ultraviolet rays under a nitrogen atmosphere so that the irradiation intensity was 100 mW / cm 2 and the dose was 3,000 mJ / cm 2 at ° C., and a touch test was performed immediately after the irradiation was completed. If the composition did not adhere to the finger, it was rated as ⁇ , and if it adhered, it was rated as x. [Additional curability] The additional curability was evaluated by weighing 0.5 g of a liquid curable composition on an aluminum petri dish to form a liquid film having a thickness of about 300 ⁇ m, subjecting it to 120 ° C. for 60 minutes, and then performing a touch test. If the composition did not adhere to the finger, it was rated as ⁇ , and if it adhered, it was rated as x.
• the curable compositions of Examples 1 to 4 had good inkjet ejection properties and were capable of both radical curing and addition curing.
• Comparative Examples 1, 2 and 6 in which the viscosity and / or the surface tension did not meet the range of the present invention, the result was that the inkjet ejection property was inferior.
• Comparative Example 3 in which a (meth) acrylic functional organopolysiloxane having no Si—H group was used instead of the component (A) of the present invention, no addition curability was exhibited.
• a (meth) acrylic functional organopolysiloxane having no Si—H group and an organohydrogenpolysiloxane having no (meth) acrylic functional group were used in combination.
• the radical curability was inferior.

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• 2020
  • 2020-12-17 EP EP20912936.0A patent/EP4089147B1/en active Active
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  • 2020-12-17 WO PCT/JP2020/047127 patent/WO2021140862A1/ja not_active Ceased
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