WO2013011822A2 - Sel d'onium ayant un groupe trialcoxysilylalkyle - Google Patents

Sel d'onium ayant un groupe trialcoxysilylalkyle Download PDF

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Publication number
WO2013011822A2
WO2013011822A2 PCT/JP2012/066824 JP2012066824W WO2013011822A2 WO 2013011822 A2 WO2013011822 A2 WO 2013011822A2 JP 2012066824 W JP2012066824 W JP 2012066824W WO 2013011822 A2 WO2013011822 A2 WO 2013011822A2
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WIPO (PCT)
Prior art keywords
carbamoyloxyethyl
bis
trifluoromethanesulfonyl
imide
trimethoxysilylpropyl
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PCT/JP2012/066824
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English (en)
Japanese (ja)
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WO2013011822A3 (fr
Inventor
洋輔 田中
卓彦 神野
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広栄化学工業株式会社
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Application filed by 広栄化学工業株式会社 filed Critical 広栄化学工業株式会社
Priority to KR1020147002021A priority Critical patent/KR101991272B1/ko
Priority to CN201280020083.XA priority patent/CN103596965B/zh
Publication of WO2013011822A2 publication Critical patent/WO2013011822A2/fr
Publication of WO2013011822A3 publication Critical patent/WO2013011822A3/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/16—Anti-static materials
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/54—Quaternary phosphonium compounds
    • C07F9/5407—Acyclic saturated phosphonium compounds

Definitions

  • the present invention relates to a novel onium salt having a trialkoxysilylalkyl group.
  • an onium salt having a trialkoxysilylalkyl group one in which a cation is a nitrogen atom or a phosphorus atom and a silicon atom bonded with an alkyl group, and an anion is bis (perfluoroalkylsulfonyl) imide is known.
  • the onium salt can impart excellent antistatic properties to the fluororesin (see Patent Document 1).
  • Patent Document 1 when the inventor applied the onium salt described in Patent Document 1 as an antistatic agent for an acrylic resin, the surface resistivity was 10 13 ⁇ / ⁇ or more, which was sufficient as an antistatic agent for an acrylic resin. It was found that it has no antistatic ability.
  • An object of the present invention is to provide a novel onium salt having a trialkoxysilylalkyl group particularly useful as an antistatic agent for acrylic resins.
  • the present inventor found an onium salt represented by the formula (1) and further used the onium salt as an antistatic agent in an acrylic resin.
  • the inventors have found that antistatic properties can be imparted, and have completed the present invention. That is, the present invention provides the formula (1): Formula (1): (In the formula, Q + represents a nitrogen cation or a phosphor cation.
  • R 1 to R 3 represent an alkyl group having 1 to 6 carbon atoms, and R 1 and R 2 are bonded to each other at the terminal to form a pyrrolidine ring or a piperidine ring.
  • D represents CH 2 , CH (CH 3 ) or CH (CH 3 ) CH 2
  • E represents NH or a sulfur atom
  • m represents an integer of 0 to 3
  • n represents an integer of 1 to 4.
  • a ⁇ represents an anion.
  • the onium salt (1) of the present invention is a useful compound because it can impart excellent antistatic properties to the acrylic resin.
  • the onium salt (1) of the present invention has the formula (1): ((Where Q + Represents a nitrogen cation or a phosphorus cation.
  • R 1 ⁇ R 3 Represents an alkyl group having 1 to 6 carbon atoms
  • R 1 And R 2 May be bonded to each other at the terminal to form a pyrrolidine ring, piperidine ring, pyridine ring, phosphorane ring, phosphorinane ring or phospholine ring.
  • R 3 Does not exist.
  • R 4 Represents an alkyl group having 1 to 4 carbon atoms.
  • D is CH 2 , CH (CH 3 ) Or CH (CH 3 ) CH 2 Indicates.
  • E represents NH or a sulfur atom.
  • m is an integer of 0 to 3
  • n is an integer of 1 to 4.
  • R in formula (1) 1 ⁇ R 3 Is an alkyl group having 1 to 6 carbon atoms, which may be linear or branched, and is preferably a linear alkyl group.
  • R 1 And R 2 And may be bonded to each other at the terminal to form a pyrrolidine ring, piperidine ring, pyridine ring, phosphorane ring, phosphorinane ring or phospholine ring.
  • R 3 Does not exist.
  • R 4 Represents an alkyl group having 1 to 4 carbon atoms, preferably an alkyl group having 1 to 2 carbon atoms.
  • D is CH 2 , CH (CH 3 ) Or CH (CH 3 ) CH 2 Indicates.
  • E represents NH or a sulfur atom.
  • m is an integer of 0 to 3, preferably 0 to 2.
  • n is an integer of 1 to 4, preferably 1 to 3.
  • a ⁇ represents an anion and (CF 3 SO 2 ) 2 N ⁇ , (FSO 2 ) 2 N ⁇ , BF 4 ⁇ , PF 6 ⁇ , CH 3 (CH 2 ) 10 CH 2 C 6 H 4 SO 3 ⁇ , CH 3 C 6 H 4 SO 3 ⁇ Or Cl ⁇ Is preferred.
  • the onium salt (1) include N- ⁇ (3-trimethoxysilylpropyl) carbamoyloxyethyl) ⁇ -N, N, N, -trimethylammonium bis (trifluoromethanesulfonyl) imide, N- ⁇ (3-Trimethoxysilylpropyl) carbamoyloxyethyl) ⁇ -N-ethyl-N, N-dimethylammonium bis (trifluoromethanesulfonyl) imide, N- ⁇ (3-trimethoxysilylpropyl) carbamoyloxyethyl) ⁇ - N, N-dimethyl-N-propyl-ammonium bis (trifluoromethanesulfonyl) imide, N- ⁇ (3-trimethoxysilylpropyl) carbamoyloxyethyl) ⁇ -N-butyl-N, N-dimethylammonium bis ( Trifluoromethanes
  • the onium salt (1) of the present invention can be produced by various methods.
  • the typical method is demonstrated in the following Reaction formula 1 and Reaction formula 2.
  • Q + , R 1 ⁇ R 4 , E, n and A ⁇ Is the same as above, Q is a nitrogen atom or a phosphorus atom, X ⁇ Represents a halogen ion, and M represents a metal atom.
  • the onium salt (6) can be produced by an ion exchange reaction between the onium halide (4) and the alkali metal salt represented by the formula (5) (hereinafter referred to as alkali metal salt (5)).
  • onium Salt (1a) can be produced.
  • compound (2) includes N-methylpyrrolidine, N-methylpiperidine, N-methylmorpholine, N-ethylpyrrolidine, N-ethylpiperidine, N-ethylmorpholine, N-propylpyrrolidine, N-propyl.
  • Piperidine N-propylmorpholine, N-isopropylpyrrolidine, N-isopropylpiperidine, N-isopropylmorpholine, N-butylpyrrolidine, N-butylpiperidine, N-butylmorpholine, N-pentylpyrrolidine, N-pentylpiperidine, N-pentyl Morpholine, N-hexylpyrrolidine, N-hexylpiperidine, N-hexylmorpholine, N-methyl-2-methylpyrrolidine, N-methyl-2-methylpiperidine, N-methyl-2-methylmorpholine, N-methyl-3- Methylpi Lysine, N-methyl-3-methylpiperidine, N-methyl-3-methylmorpholine, N-methyl-4-methylpiperidine, N-methyl-2-ethylpyrrolidine, N-methyl-2-propylpyrrolidine, N-methyl 2-isopropylpyrrolidine, N-methyl-2-butylpyr
  • Examples of the haloalkyl alcohols (3) include 2-chloroethanol, 2-bromoethanol, 2-iodoethanol and the like.
  • Examples of the alkali metal salt (5) include bis (trifluoromethanesulfonyl) imide lithium, bis (trifluoromethanesulfonyl) imide sodium, bis (trifluoromethanesulfonyl) imide potassium, lithium tetrafluoroborate, sodium tetrafluoroborate, tetrafluoro Potassium borate, lithium hexafluorophosphate, sodium hexafluorophosphate, potassium hexafluorophosphate, lithium phenol sulfonate, sodium phenol sulfonate, potassium phenol sulfonate, sodium p-toluene sulfonate, sodium p-dodecylbenzene sulfonate, etc.
  • trialkoxysilylalkyl isocyanates (7) include trimethoxysilylmethyl isocyanate, trimethoxysilylethyl isocyanate, trimethoxysilylpropyl isocyanate, trimethoxysilylbutyl isocyanate, triethoxysilylmethyl isocyanate, triethoxysilylpropyl isocyanate, Triethoxysilylbutyl isocyanate, triethoxysilylbutyl isocyanate, tripropoxysilylmethyl isocyanate, tripropoxysilylethyl isocyanate, tripropoxysilylpropyl isocyanate, tripropoxysilylbutyl isocyanate, tributoxysilylmethyl isocyanate, tributoxysilylethyl isocyanate, tributoxy Cyril Pro Le isocyanate include tributoxysilyl butyl isocyanate.
  • the quaternization reaction between the compound (2) and the haloalkyl alcohol (3) may or may not use a solvent.
  • the solvent when using the solvent include alcohols such as methanol, ethanol and 2-propanol, acetonitrile, ethyl acetate, tetrahydrofuran, dimethylformamide and the like.
  • the amount of the haloalkyl alcohol (3) used may be 0.7 mol or more, preferably 0.9 to 1.5 mol, relative to 1 mol of the compound (2).
  • the amount of the alkali metal salt (5) used in the ion exchange reaction is usually 0.8 mol or more, preferably 0.9 mol to 1.2 mol, based on 1 mol of the onium halide (4).
  • the amount is preferably 1 to 1.05 mol.
  • the ion exchange reaction is usually performed in a solvent.
  • the solvent include ketones such as acetone and methyl ethyl ketone, alcohols such as methanol, ethanol and 2-propanol, acetonitrile, ethyl acetate, tetrahydrofuran and dimethylformamide.
  • the amount used is not particularly limited, but is usually 10 parts by weight or less, preferably 1 to 10 parts by weight, particularly preferably 2 to 6 parts by weight, based on 1 part by weight of onium halides (4).
  • the onium halides (4) may be added after mixing the alkali metal salt (5) and the solvent.
  • the reaction temperature in the ion exchange reaction is usually 10 ° C. or higher, preferably 10 to 60 ° C., particularly preferably 10 to 30 ° C.
  • the solvent and the generated inorganic salt may be removed from the reaction solution.
  • the reaction solution is filtered or washed with water to remove the precipitated inorganic salt, and then combined with unit operations such as concentration, filtration, extraction, etc. (6) can be isolated.
  • the reaction solution is concentrated to precipitate the inorganic salt, filtered or washed with water to remove the inorganic salt, and then concentrated, filtered,
  • the onium salt (6) can be isolated by appropriately combining unit operations such as extraction.
  • the reaction of the obtained onium salt (6) and trialkoxysilylalkyl isocyanate (7) may or may not use a solvent.
  • Examples of the solvent when using the solvent include acetone, acetonitrile, ethyl acetate, tetrahydrofuran, dichloromethane and the like.
  • the amount of trialkoxysilylalkyl isocyanate (7) used may be 0.7 mol or more, preferably 0.9 to 1.5 mol, per 1 mol of onium salt (6).
  • As a method for separating the onium salt (1a) from the reaction solution after completion of the reaction the same method as that for the onium salt (6) can be used.
  • the onium salt (1b) can be produced by reacting the onium salt (9) with a trialkoxysilylalkyl compound represented by the formula (10) (hereinafter referred to as trialkoxysilylalkyl compound (10)).
  • onium halides (8), for example, N- (2-acryloyloxyethyl) -N, N, N-trimethylammonium chloride, N- (2-acryloyloxyethyl) -N, N , N-trimethylammonium bromide, N- (2-acryloyloxyethyl) -N, N, N-trimethylammonium iodide, N- (2-methacryloyloxyethyl) -N, N, N-trimethylammonium chloride N- (2-methacryloyloxyethyl) -N, N, N-trimethylammonium chloride, N- (2-methacryloyloxyethyl) -N, N, N-trimethylammonium bromide, N- (2- (Methacryloyloxyethyl) -N, N, N-trimethylammonium iodide and the like.
  • trialkoxysilylalkyl compounds (10) include trialkoxysilylalkylamines and trialkoxysilylalkylthiols.
  • trialkoxysilylalkylamines include trimethoxysilylmethylamine, trimethoxysilylethylamine, trimethoxysilylpropylamine, trimethoxysilylbutylamine, triethoxysilylmethylamine, triethoxysilylpropylamine, triethoxysilylbutylamine, Triethoxysilylbutylamine, tripropoxysilylmethylamine, tripropoxysilylethylamine, tripropoxysilylpropylamine, tripropoxysilylbutylamine, tributoxysilylmethylamine, tributoxysilylethylamine, tributoxysilylpropylamine, tributoxysilylbutylamine, etc.
  • trialkoxysilylalkylthiols include trimethoxysilylmethylthiol, trimethoxysilylethylthiol, trimethoxysilylpropylthiol, trimethoxysilylbutylthiol, triethoxysilylmethylthiol, triethoxysilylpropylthiol, triethoxysilyl Butylthiol, Triethoxysilylbutylthiol, Tripropoxysilylmethylthiol, Tripropoxysilylethylthiol, Tripropoxysilylpropylthiol, Tripropoxysilylbutylthiol, Tributoxysilylmethylthiol, Tributoxysilylethylthiol, Tributoxysilylpropylthiol , Tributoxysilylbutylthiol and the like.
  • the amount of the alkali metal salt (5) used in the ion exchange reaction is usually 0.8 mol or more, preferably 0.9 mol to 1.2 mol, based on 1 mol of the onium halide (8).
  • the amount is preferably 1 to 1.05 mol.
  • the ion exchange reaction is usually performed in a solvent.
  • the solvent include ketones such as acetone and methyl ethyl ketone, alcohols such as methanol, ethanol and 2-propanol, acetonitrile, ethyl acetate, tetrahydrofuran and dimethylformamide.
  • the amount used is not particularly limited, but is usually 10 parts by weight or less, preferably 1 to 10 parts by weight, particularly preferably 2 to 6 parts by weight, based on 1 part by weight of the onium halides (8).
  • the onium halides (8) may be added after mixing the alkali metal salt (5) and the solvent.
  • the reaction temperature in the ion exchange reaction is usually 10 ° C. or higher, preferably 10 to 60 ° C., particularly preferably 10 to 30 ° C.
  • the solvent and the generated inorganic salt may be removed from the reaction solution. If an inorganic salt is precipitated in the obtained reaction solution, the reaction solution is filtered or washed with water to remove the precipitated inorganic salt, and then combined with unit operations such as concentration, filtration, extraction, etc. (9) can be isolated. In addition, when the inorganic salt is not precipitated in the obtained reaction solution, the reaction solution is concentrated to precipitate the inorganic salt, filtered or washed with water to remove the inorganic salt, and then concentrated, filtered, The onium salt (9) can be isolated by appropriately combining unit operations such as extraction.
  • the reaction of the obtained onium salt (9) and trialkoxysilylalkyl compound (10) may or may not use a solvent.
  • the solvent when using the solvent include acetone, acetonitrile, ethyl acetate, tetrahydrofuran, dichloromethane and the like.
  • the amount of trialkoxysilylalkyl compound (10) used may be 0.7 mol or more, preferably 0.9 to 1.5 mol, per 1 mol of onium salt (9).
  • the same method as that for the onium salt (9) can be used.
  • the onium salt (1) thus obtained is mixed with an acrylic resin monomer and an appropriate solvent (for example, ethyl acetate, toluene, etc.) to prepare a solution, and then the solution is applied to the surface of the resin. It can be used as an antistatic agent for acrylic resins by a method such as removing the solvent.
  • a solution in which a photopolymerization initiator is added to a solution containing an acrylic resin monomer and an onium salt (1) is prepared, and the solution is applied to the surface of the resin and irradiated with ultraviolet rays to charge the acrylic resin. It can be used as an inhibitor, and an acrylic resin composition containing the onium salt (1) can be obtained.
  • 1 H-NMR uses “AL-400” manufactured by JEOL Datum Co., Ltd., and 400 MHz using (CD 3 ) 2 CO as a solvent, except when the solvent used is described. Measured with Moreover, the surface resistance value was measured at an applied voltage of 500 V using Hiresta UP (MCP-HT450) manufactured by Mitsubishi Chemical Corporation.
  • N- (2-hydroxyethyl) pyridinium bromide 522.4 g (2.56 mol), lithium bis (trifluoromethanesulfonyl) imido acid 771.7 g (2.69 mol), and ion-exchanged water 1357.8 g were added. Stir at room temperature for 2 hours.
  • N- ⁇ (3-triethoxysilylpropyl) carbamoyloxyethyl) ⁇ pyridinium bis (trifluoromethanesulfonyl) imide.
  • 1 H-NMR of the obtained N- ⁇ (3-triethoxysilylpropyl) carbamoyloxyethyl) ⁇ pyridinium bis (trifluoromethanesulfonyl) imide is shown below.
  • N- [2- ⁇ 3- (3-trimethoxysilylpropylamino) -1-oxopropoxy ⁇ ethyl] -N, N, N-trimethylammonium bis (trifluoromethanesulfonyl) imide 80.8 g (yield 97.6%) was obtained.
  • 1 H-NMR of the obtained N- [2- ⁇ 3- (3-trimethoxysilylpropylamino) -1-oxopropoxy ⁇ ethyl] -N, N, N-trimethylammonium bis (trifluoromethanesulfonyl) imide Is shown below.
  • N- [2- ⁇ 3- (3-trimethoxysilylpropylthio) -2-methyl-1-oxopropoxy ⁇ ethyl] -trimethylammonium bis (trifluoromethanesulfonyl) imide 8 g (yield 96.7%) was obtained.
  • N, N-trimethylammonium bis (trifluoromethanesulfonyl) imide 1 H-NMR is shown below.
  • N- (2-hydroxyethyl) pyridinium hexafluorophosphate 28.4 g (0.11 mol) was dissolved in acetonitrile 28.6 g, 3-trimethoxysilylpropyl isocyanate 23.1 g (0.11 mol), and 0.35 g (0.55 mmol) of dibutyltin dilaurate was added and reacted at room temperature for 5 hours.
  • the oil layer was obtained by liquid separation, and the obtained oil layer was separated and washed twice with 100 g of ion-exchanged water.
  • 1 H-NMR of the obtained tributyl (2-hydroxyethyl) phosphonium bis (trifluoromethanesulfonyl) imide is shown below.
  • Application examples 2-8 instead of N- ⁇ (3-triethoxysilylpropyl) carbamoyloxyethyl) ⁇ -N, N, N, -trimethylammonium bis (trifluoromethanesulfonyl) imide of Application Example 1, the onium salts of the present invention shown in Table 1
  • a test piece was prepared in the same manner as in Application Example 1 except that was used, and the surface resistance value of the adhesive of the test piece was measured in the same manner as in Application Example 1. The results are shown in Table 1.
  • Comparative application example 1 Similar to Application Example 1 except that N- ⁇ (3-triethoxysilylpropyl) carbamoyloxyethyl) ⁇ -N, N, N, -trimethylammonium bis (trifluoromethanesulfonyl) imide of Application Example 1 was not used. A test piece was prepared, and the surface resistance value of the adhesive of the test piece was measured in the same manner as in Application Example 1. The results are shown in Table 1.
  • the acrylic resin pressure-sensitive adhesive containing the onium salt of the present invention has a low surface resistance value.
  • Application examples 9 and 10 Dipentaerythritol hexaacrylate (A-DPH: Shin-Nakamura Chemical Co., Ltd.) 0.50 g, Pentaerythritol triacrylate (A-TMN-3LM-N: Shin-Nakamura Chemical Co., Ltd.) 1.50 g, trimethylolpropane 0.50 g of triacrylate (A-TMPT: manufactured by Shin-Nakamura Chemical Co., Ltd.), 0.23 g of onium salt (1) shown in Table 2 and colloidal silica isopropyl alcohol dispersion (IPA-ST: silica solid content 30 wt%, (Made by Nissan Chemical Industries, Ltd.) 1.80 g is mixed, and 2.16 g of isopropyl alcohol and 0.15 g of 2-hydroxy-2-methylpropiophenone as a photopolymerization
  • a monomer and photopolymerization agent-containing coating solution was prepared.
  • the resulting coating solution was coated on a 100 ⁇ m thick polyester film using a bar coater so that the coating thickness when dried was about 5 ⁇ m.
  • Acrylic resin hard coat film was prepared by irradiating ultraviolet rays from a high pressure mercury UV lamp (120 W / cm) from the coating film side under the condition of an integrated light quantity of about 400 mJ / cm 2 and curing treatment, and the obtained hard coat film The surface resistance value of was measured. The surface resistance value was 25 ⁇ 2 ° C., and the humidity was 50 ⁇ 5%. The results are shown in Table 2.
  • Comparative application example 3 Hard coat films were prepared in the same manner as in Application Examples 9 and 10 except that N- (3-trimethoxysilylpropyl) pyridinium bis (trifluoromethanesulfonyl) imide was used as the onium salt. The surface resistance value of the obtained hard coat film was measured. The results are shown in Table 2. From the results in Table 2, it was found that the acrylic resin hard coat film prepared by using the hard coat liquid containing the onium salt of the present invention showed a low surface resistance value.
  • the onium salt (1) of the present invention is a useful compound because it can impart excellent antistatic properties to the acrylic resin.

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Abstract

L'invention concerne un sel d'onium représenté par la formule (1) (Dans la formule : A- représente un anion; et le reste de la formule représente un cation onium quaternaire (dans celle-ci, Q+ représente un cation azote ou un cation phosphore; R1-R3 représentent des groupes alkyle en C1-6, et les terminaisons de R1 et R2 peuvent se lier pour former un noyau pyrrolidine, un noyau pipéridine, un noyau pyridine, un noyau phosphorane, un noyau phosphorinane ou un noyau phosphorine; si un noyau pyridine ou un noyau phosphorine est formé, R3 ne sera pas présent; R4 représente un groupe alkyle en C1-4 ; D représente CH2, CH(CH3) ou CH(CH3)CH2 ; E représente NH ou un atome de soufre; m est un entier dans la plage de 0-3, et n est un entier se situant dans la plage de 1-4).
PCT/JP2012/066824 2011-06-24 2012-06-25 Sel d'onium ayant un groupe trialcoxysilylalkyle WO2013011822A2 (fr)

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KR1020147002021A KR101991272B1 (ko) 2011-06-24 2012-06-25 트리알콕시실릴알킬기를 갖는 오늄염
CN201280020083.XA CN103596965B (zh) 2011-06-24 2012-06-25 具有三烷氧基甲硅烷基烷基的鎓盐

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JP2012078024A JP6190572B2 (ja) 2011-06-24 2012-03-29 トリアルコキシシリルアルキル基を有するオニウム塩
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EP2860183A1 (fr) * 2013-03-25 2015-04-15 Sumitomo Riko Company Limited Liquide ionique réactif et particules d'oxyde métallique immobilisées par des ions produites à l'aide de celui-ci, élastomère à ions immobilisés, et transducteur
JP2017048149A (ja) * 2015-09-02 2017-03-09 広栄化学工業株式会社 アルコキシシリルアルキル基を有するオニウム塩
WO2019073397A1 (fr) * 2017-10-10 2019-04-18 Ppg Industries Ohio, Inc. Liquides ioniques

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JP6196470B2 (ja) * 2013-05-21 2017-09-13 広栄化学工業株式会社 新規オニウム塩及びそれを含有する帯電防止剤
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JP6296857B2 (ja) 2014-03-27 2018-03-20 広栄化学工業株式会社 ポリシロキサン共重合体を含むシリコーン樹脂組成物
JP6177430B2 (ja) * 2014-04-21 2017-08-09 広栄化学工業株式会社 ポリシロキサン共重合体及びそれを含有する帯電防止剤
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JP6067075B2 (ja) * 2015-08-26 2017-01-25 藤森工業株式会社 帯電防止剤を含有する粘着剤組成物、及び粘着フィルム
JP6259060B2 (ja) * 2016-12-16 2018-01-10 藤森工業株式会社 帯電防止剤を含有する粘着剤組成物、及び粘着フィルム
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