JP2021123628A - Adhesive silicone resin composition and adhesive film coated with the same - Google Patents
Adhesive silicone resin composition and adhesive film coated with the same Download PDFInfo
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- 239000000853 adhesive Substances 0.000 title claims abstract description 30
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 30
- 239000011342 resin composition Substances 0.000 title claims abstract description 23
- 229920002050 silicone resin Polymers 0.000 title claims abstract description 23
- 239000002313 adhesive film Substances 0.000 title abstract description 31
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 64
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 18
- 229920006136 organohydrogenpolysiloxane Polymers 0.000 claims abstract description 16
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 15
- 229920005989 resin Polymers 0.000 claims abstract description 15
- 239000011347 resin Substances 0.000 claims abstract description 15
- 150000003568 thioethers Chemical class 0.000 claims abstract description 14
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 11
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- 238000007259 addition reaction Methods 0.000 claims abstract description 8
- 125000005372 silanol group Chemical group 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 11
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims description 8
- 229910004283 SiO 4 Inorganic materials 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 229910020388 SiO1/2 Inorganic materials 0.000 abstract 2
- 229910020485 SiO4/2 Inorganic materials 0.000 abstract 2
- 230000000052 comparative effect Effects 0.000 description 7
- -1 copper Chemical class 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- 239000011521 glass Substances 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 229920001721 polyimide Polymers 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 229920006267 polyester film Polymers 0.000 description 3
- 229910000679 solder Inorganic materials 0.000 description 3
- ODJQKYXPKWQWNK-UHFFFAOYSA-N 3,3'-Thiobispropanoic acid Chemical compound OC(=O)CCSCCC(O)=O ODJQKYXPKWQWNK-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000002683 reaction inhibitor Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- QYLFHLNFIHBCPR-UHFFFAOYSA-N 1-ethynylcyclohexan-1-ol Chemical compound C#CC1(O)CCCCC1 QYLFHLNFIHBCPR-UHFFFAOYSA-N 0.000 description 1
- GSQDENNAGLQNCW-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol 3-dodecylsulfanylpropanoic acid Chemical compound OCC(CO)(CO)CO.CCCCCCCCCCCCSCCC(O)=O GSQDENNAGLQNCW-UHFFFAOYSA-N 0.000 description 1
- IHFZNOGVOSLFRI-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol 3-dodecylsulfanylpropanoic acid Chemical compound OCC(CO)(CO)CO.CCCCCCCCCCCCSCCC(O)=O.CCCCCCCCCCCCSCCC(O)=O.CCCCCCCCCCCCSCCC(O)=O.CCCCCCCCCCCCSCCC(O)=O IHFZNOGVOSLFRI-UHFFFAOYSA-N 0.000 description 1
- VMAWODUEPLAHOE-UHFFFAOYSA-N 2,4,6,8-tetrakis(ethenyl)-2,4,6,8-tetramethyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical compound C=C[Si]1(C)O[Si](C)(C=C)O[Si](C)(C=C)O[Si](C)(C=C)O1 VMAWODUEPLAHOE-UHFFFAOYSA-N 0.000 description 1
- CEBKHWWANWSNTI-UHFFFAOYSA-N 2-methylbut-3-yn-2-ol Chemical compound CC(C)(O)C#C CEBKHWWANWSNTI-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000002788 crimping Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- BITPLIXHRASDQB-UHFFFAOYSA-N ethenyl-[ethenyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound C=C[Si](C)(C)O[Si](C)(C)C=C BITPLIXHRASDQB-UHFFFAOYSA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000006459 hydrosilylation reaction Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 150000003058 platinum compounds Chemical class 0.000 description 1
- 229920003223 poly(pyromellitimide-1,4-diphenyl ether) Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Adhesive Tapes (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Description
本発明は、ポリエステルフィルムやポリイミドフィルム等のベースフィルムの少なくとも片面に塗布してシリコーン層を形成して粘着フィルムとする粘着性シリコーン樹脂組成物及びこれを塗布した粘着フィルムに関し、特には該粘着フィルムが貼着された電子部材が例えば、はんだリフロー工程において２５０℃超の環境下に置かれた場合であっても、電子部材側に粘着フィルムのシリコーン層の一部が残ったり、シリコーン層の痕跡が生じる（以下、糊残り、という）ことが無い、粘着性シリコーン樹脂組成物及びこれを塗布した粘着フィルムに関する。 The present invention relates to an adhesive silicone resin composition which is applied to at least one surface of a base film such as a polyester film or a polyimide film to form a silicone layer to form an adhesive film, and an adhesive film to which the adhesive film is applied. For example, even when the electronic member to which is attached is placed in an environment of more than 250 ° C. in the solder reflow process, a part of the silicone layer of the adhesive film remains on the electronic member side or traces of the silicone layer. The present invention relates to an adhesive silicone resin composition and an adhesive film coated with the adhesive silicone resin composition, which does not cause (hereinafter, referred to as adhesive residue).
従来、銅などの金属に対して用いた場合でも糊残りしない粘着テープとして、（Ａ）アルケニル基含有ポリジオルガノシロキサン２０〜８０重量部、（Ｂ）Ｒ１ ３ＳｉＯ０．５単位及びＳｉＯ２単位を含有し、Ｒ１ ３ＳｉＯ．５単位／ＳｉＯ２単位のモル比が０．６〜１．７であるポリオルガノシロキサン（Ｒ１は炭素数１〜１０の１価炭化水素基）８０〜２０重量部、（Ｃ）ＳｉＨ基を含有するポリオルガノシロキサン（Ａ）成分中のアルケニル基に対する（Ｃ）成分中のＳｉＨ基のモル比が０．５〜２０となる量、（Ｄ）制御剤 （Ａ），（Ｂ）成分の合計１００重量部に対して０〜５．０重量部、（Ｅ）白金系触媒 （Ａ），（Ｂ）成分の合計に対し白金分として１〜５，０００ｐｐｍ、（Ｆ）フェノール系酸化防止剤として、分子中に特定構造で示される構造を有するフェノール系化合物 （Ａ），（Ｂ）の合計１００重量部に対して０．１〜１０重量部を含有することを特徴とするシリコーン粘着剤組成物が提案されている（特許文献１）。 Conventionally, as an adhesive tape without adhesive residue even with respect to metals such as copper, (A) alkenyl group-containing polydiorganosiloxane 20-80 parts by weight, (B) R 1 3 SiO 0.5 units and SiO 2 units Containing R 1 3 Si O. 80 to 20 parts by weight of polyorganosiloxane (R 1 is a monovalent hydrocarbon group having 1 to 10 carbon atoms) having a molar ratio of 5 units / SiO 2 units of 0.6 to 1.7, and (C) SiH group. The amount by which the molar ratio of the SiH group in the component (C) to the alkenyl group in the polyorganosiloxane (A) component contained is 0.5 to 20, and the total of the components (D) and the control agents (A) and (B). 0 to 5.0 parts by weight with respect to 100 parts by weight, 1 to 5,000 ppm as platinum content with respect to the total of (E) platinum-based catalysts (A) and (B) components, and (F) as a phenol-based antioxidant. , A silicone pressure-sensitive adhesive composition containing 0.1 to 10 parts by weight with respect to a total of 100 parts by weight of the phenolic compounds (A) and (B) having a structure represented by a specific structure in the molecule. Has been proposed (Patent Document 1).
しかしながら、該シリコーン粘着剤組成物は、これが塗布されシリコーン層が形成された粘着フィルムが貼着された電子部材等が例えば、はんだリフロー工程において２５０℃超の環境下に置かれた場合、電子部材側に粘着フィルムのシリコーン層の一部が糊残りすることがあるという課題がある。 However, in the silicone pressure-sensitive adhesive composition, when an electronic member or the like to which the pressure-sensitive adhesive film coated with the silicone pressure-sensitive adhesive film is attached is placed in an environment of more than 250 ° C. in a solder reflow process, for example, the electronic member There is a problem that a part of the silicone layer of the adhesive film may remain on the side.
本発明が解決しようとする課題は、シリコーン層が形成された粘着フィルムが貼着された電子部材等が、２５０℃超の環境下に置かれた場合であっても、電子部材側に粘着フィルムのシリコーン層の一部が糊残りすることが無い、粘着性シリコーン樹脂組成物及びこれを塗布した粘着フィルムを提供することにある。 The problem to be solved by the present invention is that the adhesive film on the electronic member side even when the electronic member or the like to which the adhesive film on which the silicone layer is formed is placed in an environment of more than 250 ° C. It is an object of the present invention to provide an adhesive silicone resin composition and an adhesive film coated with the adhesive silicone resin composition, in which a part of the silicone layer of the above does not remain adhesive.
上記課題を解決するため、請求項１記載の発明は、
１分子中にＳｉＨ基と反応する珪素結合アルケニル基を少なくとも２個有するオルガノポリシロキサン（Ａ）と、
１分子中に少なくとも３個のＳｉＨ基を有するオルガノ水素ポリシロキサン（Ｂ）と、
１分子中に少なくとも１個のシラノール基を有し、一般式ＳｉＯ１／２単位とＳｉＯ４／２単位から成り、ＳｉＯ１／２単位／ＳｉＯ４／２単位のモル比が０．５〜１．０であるオルガノポリシロキサン樹脂（Ｃ）と
付加反応に必要な硬化触媒（Ｄ）と、
分子中に下記化学式Ｉを有するチオエーテル系酸化防止剤（Ｅ）
Organopolysiloxane (A) having at least two silicon-bonded alkenyl groups that react with SiH groups in one molecule,
Organohydrogen polysiloxane (B) having at least 3 SiH groups in one molecule,
It has at least one silanol group in one molecule, and is composed of the general formula SiO 1/2 unit and SiO 4/2 unit, and the molar ratio of SiO 1/2 unit / SiO 4/2 unit is 0.5 to 1. Organopolysiloxane resin (C) of .0, curing catalyst (D) required for addition reaction, and
Thioether-based antioxidant (E) having the following chemical formula I in the molecule
また請求項２記載の発明は、
オルガノポリシロキサン樹脂（Ｃ）はオルガノポリシロキサン（Ａ）とオルガノポリシロキサン樹脂（Ｃ）の合計部数１００重量部に対して１０〜９０重量部であり、
オルガノ水素ポリシロキサン（Ｂ）はオルガノポリシロキサン（Ａ）中のアルケニル基に対するオルガノ水素ポリシロキサン（Ｂ）のＳｉＨ基のモル比が０．５〜２０となる量であり、
チオエーテル系酸化防止剤（Ｅ）は組成物全体１００重量部に対して０．０２〜５重量部である、
ことを特徴とする粘着性シリコーン樹脂組成物を提供する。
The invention according to claim 2 is the invention.
The organopolysiloxane resin (C) is 10 to 90 parts by weight based on 100 parts by weight of the total number of the organopolysiloxane (A) and the organopolysiloxane resin (C).
The organohydrogen polysiloxane (B) is an amount such that the molar ratio of the SiH group of the organohydrogen polysiloxane (B) to the alkenyl group in the organopolysiloxane (A) is 0.5 to 20.
The thioether-based antioxidant (E) is 0.02 to 5 parts by weight based on 100 parts by weight of the entire composition.
Provided is an adhesive silicone resin composition characterized by the above.
また請求項３記載の発明は、
ベースフィルムの少なくとも片面に請求項１又は請求項２に記載の粘着性シリコーン樹脂組成物を塗布してシリコーン層を形成したことを特徴とする粘着フィルムを提供する。
The invention according to claim 3 is the invention.
Provided is an adhesive film characterized in that a silicone layer is formed by applying the adhesive silicone resin composition according to claim 1 or 2 to at least one surface of a base film.
本発明の粘着性シリコーン樹脂組成物は、ポリエステルフィルムやポリイミドフィルム等のベースフィルム対して十分な接着力を有し、結果としてこれが塗布されシリコーン層が形成された粘着フィルムは、貼着される部材に対して十分な剥離強度を有する効果がある。また本発明の粘着性シリコーン樹脂組成物が塗布されシリコーン層が形成された粘着フィルムが貼着された電子部材等が例えば、はんだリフロー工程において２５０℃超の環境下に置かれた場合であっても、電子部材側に粘着フィルムのシリコーン層の一部が糊残りすることがないという効果がある。 The adhesive silicone resin composition of the present invention has sufficient adhesive strength with respect to a base film such as a polyester film or a polyimide film, and as a result, the adhesive film to which the adhesive film is applied to form a silicone layer is a member to be attached. It has the effect of having sufficient peeling strength. Further, when the electronic member or the like to which the adhesive silicone resin composition of the present invention is applied and the adhesive film on which the silicone layer is formed is attached is placed in an environment of more than 250 ° C. in the solder reflow process, for example. However, there is an effect that a part of the silicone layer of the adhesive film does not remain on the electronic member side.
以下、本発明に係る粘着性シリコーン樹脂組成物について具体的に説明する。 Hereinafter, the adhesive silicone resin composition according to the present invention will be specifically described.
＜オルガノポリシロキサン（Ａ）＞
本発明に使用するオルガノポリシロキサン（Ａ）は、１分子中にＳｉＨ基と反応する珪素結合アルケニル基を少なくとも２個有し、該アルケニル基はビニル基、アリル基、プロペニル基、イソプロペニル基、ブテニル基、イソブテニル基、ヘキセニル基などの炭素−炭素二重結合である。該オルガノポリシロキサン（Ａ）は例えば主鎖がジオルガノシロキサンの繰返し単位であり、末端にアルケニル基を有するものが例示され、分岐や環状構造を有するものであってもよい。末端や繰返し単位中のケイ素に結合するオルガノ基としてはメチル基、エチル基、フェニル基などが例示される。具体例としては、両末端にビニル基を有するジメチルビニルポリシロキサンが挙げられる。
<Organopolysiloxane (A)>
The organopolysiloxane (A) used in the present invention has at least two silicon-bonded alkenyl groups that react with a SiH group in one molecule, and the alkenyl groups are a vinyl group, an allyl group, a propenyl group, an isopropenyl group, and the like. It is a carbon-carbon double bond such as a butenyl group, an isobutenyl group, and a hexenyl group. The organopolysiloxane (A) is, for example, a repeating unit having a main chain of diorganosiloxane and having an alkenyl group at the terminal, and may have a branched or cyclic structure. Examples of the organogroup bonded to silicon at the terminal or in the repeating unit include a methyl group, an ethyl group, and a phenyl group. Specific examples include dimethylvinylpolysiloxane having vinyl groups at both ends.
＜オルガノ水素ポリシロキサン（Ｂ）＞
本発明に使用するオルガノ水素ポリシロキサン（Ｂ）は、１分子中に少なくとも３個のＳｉＨ基を含有する。珪素原子に結合している水素原子の含有量は０．５ｍｍｏｌ／ｇ〜２０．０ｍｍｏｌ／ｇであることが好ましく、０．５ｍｍｏｌ／ｇ以上であると硬化性がよくなる。水素原子の含有量が２０．０ｍｍｏｌ／ｇ超であると、硬化物表面ベタツキが生じやすくなる。ベタツキが生じ難くするためには水素原子含有量は１．５ｍｍｏｌ／ｇ〜１５．０ｍｍｏｌ／ｇであることがより好ましい。珪素原子に結合するオルガノ基としては、メチル基、エチル基、フェニル基などが例示される。該オルガノ水素ポリシロキサンは、例えば直鎖状または分岐鎖状、であってもよく、具体例としては、ジメチル水素ポリシロキサンが挙げられる。オルガノ水素ポリシロキサン（Ｂ）の配合量は、上記オルガノポリシロキサン（Ａ）のアルケニル基１モルに対して珪素結合水素原子が０．５〜２０モルとなる量が好ましい。０．５モル未満では硬化性が低下し、２０モル超では硬化物が発泡する場合がある。
<Organo hydrogen polysiloxane (B)>
The organohydrogen polysiloxane (B) used in the present invention contains at least three SiH groups in one molecule. The content of the hydrogen atom bonded to the silicon atom is preferably 0.5 mmol / g to 20.0 mmol / g, and when it is 0.5 mmol / g or more, the curability is improved. When the content of hydrogen atoms exceeds 20.0 mmol / g, the surface of the cured product tends to become sticky. The hydrogen atom content is more preferably 1.5 mmol / g to 15.0 mmol / g in order to prevent stickiness. Examples of the organogroup bonded to the silicon atom include a methyl group, an ethyl group, and a phenyl group. The organohydrogen polysiloxane may be, for example, linear or branched chain, and specific examples thereof include dimethyl hydrogen polysiloxane. The blending amount of the organohydrogen polysiloxane (B) is preferably an amount in which the silicon-bonded hydrogen atom is 0.5 to 20 mol with respect to 1 mol of the alkenyl group of the organopolysiloxane (A). If it is less than 0.5 mol, the curability is lowered, and if it is more than 20 mol, the cured product may foam.
＜オルガノポリシロキサン樹脂（Ｃ）＞
本発明に使用するオルガノポリシロキサン樹脂（Ｃ）は、１分子中に少なくとも１個のシラノール基を有し、一般式ＳｉＯ１/２単位とＳｉＯ４/２単位から成り、ＳｉＯ１/２単位／ＳｉＯ４/２単位のモル比が０．５〜１．０であり、本発明である粘着性シリコーン樹脂組成物の初期粘着性を向上させるために配合する。ＯＨ基含有量は０．１〜５．０重量％が好ましく、ＯＨ基含有量が５．０重量％超となると組成物の硬化性が低下する。ＳｉＯ１/２単位／ＳｉＯ４/２単位のモル比が０．５未満及び１．０超では剥離強度が不十分となることがある。
<Organopolysiloxane resin (C)>
The organopolysiloxane resin (C) used in the present invention has at least one silanol group in one molecule, and is composed of the general formula SiO 1/2 unit and SiO 4/2 unit, and SiO 1/2 unit / The molar ratio of 4/2 units of SiO is 0.5 to 1.0, and it is blended in order to improve the initial adhesiveness of the adhesive silicone resin composition of the present invention. The OH group content is preferably 0.1 to 5.0% by weight, and when the OH group content exceeds 5.0% by weight, the curability of the composition is lowered. If the molar ratio of SiO 1/2 unit / SiO 4/2 unit is less than 0.5 and more than 1.0, the peel strength may be insufficient.
上記オルガノポリシロキサン樹脂（Ｃ）は、オルガノポリシロキサン（Ａ）とオルガノポリシロキサン樹脂（Ｃ）との合計部数１００重量部に対して１０〜９０重量部が好ましく、１０重量部未満又は９０重量部超では十分な粘着力が得られない場合がある。 The organopolysiloxane resin (C) is preferably 10 to 90 parts by weight, preferably less than 10 parts by weight or 90 parts by weight, based on 100 parts by weight of the total number of copies of the organopolysiloxane (A) and the organopolysiloxane resin (C). Sufficient adhesive strength may not be obtained with super.
＜硬化触媒（Ｄ）＞
本発明に使用される硬化触媒（Ｄ）は、上記オルガノポリシロキサン（Ａ）及びオルガノ水素ポリシロキサン（Ｂ）との付加反応を起こさせるために使用され、付加反応であるヒドロシリル化反応の触媒活性を有する公知の金属、金属化合物、金属錯体などを用いることができる。特に白金、白金化合物、それらの錯体を用いることが好ましい。これらの触媒は単独で使用してもよく、２種以上を併用してもよい。また、助触媒を併用してもよい。硬化触媒（Ｄ）の配合量は組成物全体に対して０．１ｐｐｍ〜１０００ｐｐｍとすることが好ましく、より好ましくは０．５〜２００ｐｐｍであり、さらにより好ましくは１〜５０ｐｐｍである。
<Curing catalyst (D)>
The curing catalyst (D) used in the present invention is used to cause an addition reaction with the organopolysiloxane (A) and the organohydrogenpolysiloxane (B), and the catalytic activity of the hydrosilylation reaction, which is an addition reaction. Known metals, metal compounds, metal complexes and the like having the above can be used. In particular, it is preferable to use platinum, a platinum compound, or a complex thereof. These catalysts may be used alone or in combination of two or more. Further, a co-catalyst may be used in combination. The blending amount of the curing catalyst (D) is preferably 0.1 ppm to 1000 ppm, more preferably 0.5 to 200 ppm, and even more preferably 1 to 50 ppm with respect to the entire composition.
＜チオエーテル系酸化防止剤（Ｅ）＞
本発明に使用するチオエーテル系酸化防止剤は、分子中に下記化学式Ｉを有する。本発明においては該チオエーテル系酸化防止剤を他のフェノール系酸化防止剤と併用せずとも耐熱性が付与され、具体的には、例えば２５０℃超の熱履歴を受けても糊残りが生じない。該チオエーテル系酸化防止剤（Ｅ）は組成物全体１００重量部に対して０．０２〜５重量部含有することが好ましく、０．０５〜３重量部含有することがより好ましい。含有量が０．０２重量部未満では糊残りが生じる場合があり、５重量部超ではオルガノポリシロキサン（Ａ）とオルガノ水素ポリシロキサン（Ｂ）との付加反応による硬化が不十分となる場合がある。含有量が０．０５重量部未満では糊残りが生じる傾向がみられる場合があり、３重量部超ではオルガノポリシロキサン（Ａ）とオルガノ水素ポリシロキサン（Ｂ）との付加反応による硬化が不十分となる傾向がみられる場合がある。
The thioether-based antioxidant used in the present invention has the following chemical formula I in its molecule. In the present invention, heat resistance is imparted without using the thioether-based antioxidant in combination with another phenol-based antioxidant. Specifically, for example, no adhesive residue is generated even when subjected to a heat history of more than 250 ° C. .. The thioether-based antioxidant (E) is preferably contained in an amount of 0.02 to 5 parts by weight, more preferably 0.05 to 3 parts by weight, based on 100 parts by weight of the entire composition. If the content is less than 0.02 parts by weight, adhesive residue may occur, and if it exceeds 5 parts by weight, curing by the addition reaction of organopolysiloxane (A) and organohydrogenpolysiloxane (B) may be insufficient. be. If the content is less than 0.05 parts by weight, adhesive residue may tend to occur, and if it exceeds 3 parts by weight, curing due to the addition reaction of organopolysiloxane (A) and organohydrogenpolysiloxane (B) is insufficient. There may be a tendency to become.
チオエーテル系酸化防止剤（Ｅ）の具体例としては、下記化学式ＩＩを有する３，３´−チオビスプロピオン酸ジドリデシルや、下記化学式ＩＩＩを有するテトラキス［３−（ドデシルチオ）プロピオン酸］ペンタエリトリトールがある。
本組成物には、その他任意の成分として、３−メチル−１−ブチン−３−オール、３,５−ジメチル−１−ヘキシン−３−オール、エチニルシクロヘキサノール等のアルキンアルコール；３−メチル−３−ペンテン−１−イン、３,５−ジメチル−３−ヘキセン−１−イン等のエンイン化合物；１,３,５,７−テトラメチル−１,３,５,７−テトラビニルシクロテトラシロキサン、１,３,５,７−テトラメチル−１,３,５,７−テトラヘキセニルシクロテトラシロキサン、１，３ジビニルテトラメチルジシロキサン、ベンゾトリアゾール等の反応抑制剤を含有してもよい。この反応抑制剤は付加反応による硬化性を抑制しない程度の含有量としてオルガノポリシロキサン（Ａ）とオルガノ水素ポリシロキサン（Ｂ）との合計配合物数１００重量部に対して０.０００１〜１重量部の範囲内であることが好ましい。 In this composition, as any other component, alkyne alcohols such as 3-methyl-1-butyne-3-ol, 3,5-dimethyl-1-hexin-3-ol, and ethynylcyclohexanol; 3-methyl- Enyne compounds such as 3-pentene-1-in, 3,5-dimethyl-3-hexen-1-in; 1,3,5,7-tetramethyl-1,3,5,7-tetravinylcyclotetrasiloxane Reaction inhibitors such as 1,3,5,7-tetramethyl-1,3,5,7-tetrahexenylcyclotetrasiloxane, 1,3 divinyltetramethyldisiloxane, and benzotriazole may be contained. The content of this reaction inhibitor is 0.0001 to 1 weight based on 100 parts by weight of the total amount of the organopolysiloxane (A) and the organohydrogenpolysiloxane (B) so as not to suppress the curability due to the addition reaction. It is preferably within the range of parts.
また本組成物には発明の目的を損なわない程度に、その他任意成分として粘度調整、硬さ調整のために炭酸カルシウム、硅砂、タルク、カーボンブラック、酸化チタン、酸化亜鉛、カオリン、二酸化ケイ素、メラミン等の無機充填材を含有してもよく、有機充填材、硬化樹脂の補強のためにガラス繊維等の補強材、軽量化及び粘度調整などのためにシラスバルーン、ガラスバルーン等の中空体を添加できる。また粘度を下げて塗工性を向上させるためにトルエン、キシレン、酢酸エチル、ヘキサン、オクタン等の有機系溶剤を添加しても良い。その他、酸化防止剤、有機顔料、蛍光顔料、腐食防止剤、酸化防止剤などを適宜使用することができる。 In addition, the present composition contains calcium carbonate, glass sand, talc, carbon black, titanium oxide, zinc oxide, kaolin, silicon dioxide, and melamine as other optional components to the extent that the object of the invention is not impaired. Inorganic fillers such as organic fillers, reinforcing materials such as glass fibers for reinforcing cured resins, and hollow bodies such as silas balloons and glass balloons for weight reduction and viscosity adjustment are added. can. Further, an organic solvent such as toluene, xylene, ethyl acetate, hexane or octane may be added in order to lower the viscosity and improve the coatability. In addition, antioxidants, organic pigments, fluorescent pigments, corrosion inhibitors, antioxidants and the like can be appropriately used.
本発明の請求項３に記載の粘着フィルムは、ポリエステルフィルムやポリイミドフィルム等のベースフィルムの少なくとも片面に上記請求項１又は請求項２に記載の粘着性シリコーン樹脂組成物を塗布してシリコーン層を形成した粘着フィルムである。 The adhesive film according to claim 3 of the present invention is formed by applying the adhesive silicone resin composition according to claim 1 or 2 to at least one side of a base film such as a polyester film or a polyimide film to form a silicone layer. The formed adhesive film.
シリコーン層塗工液の塗工方法としては、３本オフセットグラビアコーターや５本ロールコーターに代表される多段ロールコーター、ダイレクトグラビアコーター、バーコーター、エアナイフコーター等が適宜使用される。ベースフィルムは易接着層としてポリエステル樹脂が塗工されていても未処理のポリエステル等のフィルムであってもよい。 As a coating method of the silicone layer coating liquid, a multi-stage roll coater typified by a three-off offset gravure coater or a five-roll coater, a direct gravure coater, a bar coater, an air knife coater, or the like is appropriately used. The base film may be a film such as polyester which has been coated with a polyester resin as an easy-adhesion layer or has not been treated.
シリコーン層を形成後は、該シリコーン層の表面の汚れや異物付着を防止すると共に、粘着フィルムのハンドリング性を向上させるためにさらに樹脂フィルムやコート紙等のセパレータをシリコーン層面に貼り合わせるとよい。 After forming the silicone layer, it is preferable to further attach a separator such as a resin film or coated paper to the surface of the silicone layer in order to prevent stains and foreign matter from adhering to the surface of the silicone layer and to improve the handleability of the adhesive film.
次に、本発明である粘着性シリコーン樹脂組成物について、実施例及び比較例により詳細に説明する。 Next, the adhesive silicone resin composition of the present invention will be described in detail with reference to Examples and Comparative Examples.
＜実施例及び比較例＞
オルガノポリシロキサン（Ａ）として、末端及び側鎖にビニル基を有し、ビニル基含有率が０．０７重量％でありＧＰＣによる重量平均分子量が６００，０００であるオルガノポリシロキサン（Ａ１）、及び末端及び側鎖にビニル基を有し、ビニル基含有率が１．０重量％であり同重量平均分子量が５００，０００であるオルガノポリシロキサン（Ａ２）を、オルガノ水素ポリシロキサン（Ｂ）として、側鎖にＳｉＨ基を有し、珪素原子に結合している水素原子の含有量が１４ｍｍｏｌ／ｇであり同重量平均分子量が４５０のオルガノ水素ポリシロキサン（Ｂ１）を、オルガノポリシロキサン樹脂（Ｃ）としてＯＨ基含有量が１．５重量％でＳｉＯ１/２単位／ＳｉＯ４/２単位から成り、ＳｉＯ１/２単位／ＳｉＯ４/２単位のモル比が０．７からなるオルガノポリシロキサン樹脂（Ｃ１）を、硬化触媒（Ｄ）として白金―ビニルダイマー錯体（Ｐｔ：１２％ｗｔ）を、チオエーテル系酸化防止剤（Ｅ）として、上記化学式ＩＩで示される３，３´−チオビスプロピオン酸ジドリデシルから成るチオエーテル系酸化防止剤（Ｅ１）、及び上記化学式ＩＩＩで示されるテトラキス［３−（ドデシルチオ）プロピオン酸］ペンタエリトリトールから成るチオエーテル系酸化防止剤（Ｅ２）を、これらのチオエーテル系酸化防止剤（Ｅ）と比較するため、下記化学式ＩＶで示されるオクチル−３，５−ジ−ｔｅｒｔ−ブチル−４−ヒドロキシ−ヒドロ肉桂酸から成るフェノール系酸化防止剤を、反応制御剤として１−エチニルシクロヘキサノールを、それぞれ使用し、表１の配合にて均一に混合し、実施例及び比較例の粘着性シリコーン樹脂組成物を得て、該組成物１００重量部にトルエン１５０重量部を均一に混合し、粘着性シリコーン樹脂組成物の塗工液とした。次に該塗工液を、厚さ５０μｍのポリイミド製フィルム カプトン２００ＥＮ（東レ・デュポン株式会社製）上に乾燥後の厚みが２５μｍと成るように塗布し１３０℃にて１２０秒間硬化させることによりシリコーン層を形成し、実施例及び比較例の粘着性シリコーン樹脂組成物が塗布された粘着フィルムを得た。
Organopolysiloxane (A) includes organopolysiloxane (A1), which has vinyl groups at the ends and side chains, has a vinyl group content of 0.07% by weight, and has a weight average molecular weight of 600,000 according to GPC. Organopolysiloxane (A2) having vinyl groups at the ends and side chains, having a vinyl group content of 1.0% by weight and having the same weight average molecular weight of 500,000 is used as organohydrogenpolysiloxane (B). An organohydrosiloxane polysiloxane (B1) having a SiH group in the side chain, having a hydrogen atom content of 14 mmol / g bonded to a silicon atom, and having the same weight average molecular weight of 450 is used as an organopolysiloxane resin (C). OH group content consists SiO 1/2 units / SiO 4/2 units 1.5% by weight, the organopolysiloxane resin molar ratio of SiO 1/2 units / SiO 4/2 units is 0.7 Using (C1) as a curing catalyst (D), a platinum-vinyl dimer complex (Pt: 12% wt) as a thioether-based antioxidant (E), and 3,3'-thiobispropionic acid represented by the above chemical formula II. A thioether-based antioxidant (E1) composed of didridecyl and a thioether-based antioxidant (E2) composed of tetraxane [3- (dodecylthio) propionic acid] pentaerythritol represented by the above chemical formula III are used as these thioether-based antioxidants. In order to compare with (E), a phenolic antioxidant composed of octyl-3,5-di-tert-butyl-4-hydroxy-hydrosilicate silicate represented by the following chemical formula IV is used as a reaction control agent for 1-ethynylcyclo. Hexanol was used and mixed uniformly according to the formulation shown in Table 1 to obtain the adhesive silicone resin compositions of Examples and Comparative Examples, and 150 parts by weight of toluene was uniformly mixed with 100 parts by weight of the composition. , A coating liquid for an adhesive silicone resin composition. Next, the coating liquid is applied onto a polyimide film Kapton 200EN (manufactured by Toray DuPont Co., Ltd.) having a thickness of 50 μm so that the thickness after drying is 25 μm, and the silicone is cured at 130 ° C. for 120 seconds. A layer was formed, and an adhesive film coated with the adhesive silicone resin compositions of Examples and Comparative Examples was obtained.
＜評価項目及び評価方法＞ <Evaluation items and evaluation methods>
＜硬化性＞
実施例及び比較例の各粘着フィルムを２．５ｃｍ×１５ｃｍの短冊状に成形し、該粘着フィルムのシリコーン層をソーダガラス表面に密着させ、ＪＩＳＺ０２３７に規定する２ｋｇのハンドローラーを粘着フィルム上で１往復させて該シリコーン層を圧着させた。その後、粘着フィルムをゆっくりと剥がし、ガラス表面の状態を目視及び指触にて観察した。ガラス表面に曇りやべたつきが無いものを○、曇りやべたつきが有るものを×と評価した。
<Curable>
Each of the pressure-sensitive adhesive films of Examples and Comparative Examples was formed into a strip of 2.5 cm × 15 cm, the silicone layer of the pressure-sensitive adhesive film was brought into close contact with the surface of soda glass, and a 2 kg hand roller specified in JISZ0237 was placed on the pressure-sensitive adhesive film. The silicone layer was crimped by reciprocating. Then, the adhesive film was slowly peeled off, and the state of the glass surface was visually and touched. Those with no cloudiness or stickiness on the glass surface were evaluated as ◯, and those with cloudiness or stickiness were evaluated as ×.
＜剥離強度＞
実施例及び比較例の各粘着フィルムを２．５ｃｍ×１５ｃｍの短冊状に成形し、該粘着フィルムのシリコーン層をＳＵＳ３０４製のステンレス板に密着させ、ＪＩＳＺ０２３７に規定する２ｋｇのハンドローラーを粘着フィルム上で１往復させて該シリコーン層を圧着させた。圧着後、２３℃下において、ＪＩＳＺ０２３７に準拠して１８０度剥離強度（Ｎ／２５ｍｍ）を測定した。剥離強度が１．０Ｎ／２５ｍｍ超であれば十分な剥離強度を有すると判断した。
<Peeling strength>
Each of the adhesive films of Examples and Comparative Examples was formed into a strip of 2.5 cm × 15 cm, the silicone layer of the adhesive film was brought into close contact with a stainless plate made of SUS304, and a 2 kg hand roller specified in JISZ0237 was placed on the adhesive film. The silicone layer was crimped by reciprocating once. After crimping, the peel strength (N / 25 mm) of 180 degrees was measured at 23 ° C. in accordance with JISZ0237. It was judged that the peel strength was sufficient if the peel strength was more than 1.0 N / 25 mm.
＜糊残り性＞
実施例及び比較例の各粘着フィルムを２．５ｃｍ×１５ｃｍの短冊状に成形し、該粘着フィルムのシリコーン層をＳＵＳ３０４製のステンレス板に密着させ、ＪＩＳＺ０２３７に規定する２ｋｇのハンドローラーを粘着フィルム上で１往復させて該シリコーン層を圧着させた。その後、２７０℃のオーブン内に２時間放置した後２３℃に徐冷し、粘着フィルムをゆっくりと剥がし、ステンレス板表面の状態を目視及び指触にて観察した。ステンレス板表面にシリコーン層の移行が無いものを○、シリコーン層の移行が有るものを×と評価した。
<Glue residue>
Each of the adhesive films of Examples and Comparative Examples was formed into a strip of 2.5 cm × 15 cm, the silicone layer of the adhesive film was brought into close contact with a stainless plate made of SUS304, and a 2 kg hand roller specified in JISZ0237 was placed on the adhesive film. The silicone layer was crimped by reciprocating once. Then, after leaving it in an oven at 270 ° C. for 2 hours, it was slowly cooled to 23 ° C., the adhesive film was slowly peeled off, and the state of the surface of the stainless steel plate was visually and touched. Those without the migration of the silicone layer on the surface of the stainless steel plate were evaluated as ◯, and those with the migration of the silicone layer were evaluated as x.
＜評価結果＞
評価結果を表２に示す。
<Evaluation result>
The evaluation results are shown in Table 2.
Claims (3)
１分子中に少なくとも３個のＳｉＨ基を有するオルガノ水素ポリシロキサン（Ｂ）と、
１分子中に少なくとも１個のシラノール基を有し、一般式ＳｉＯ１／２単位とＳｉＯ４／２単位から成り、ＳｉＯ１／２単位／ＳｉＯ４／２単位のモル比が０．５〜１．０であるオルガノポリシロキサン樹脂（Ｃ）と
付加反応に必要な硬化触媒（Ｄ）と、
分子中に下記化学式Ｉを有するチオエーテル系酸化防止剤（Ｅ）
Organohydrogen polysiloxane (B) having at least 3 SiH groups in one molecule,
It has at least one silanol group in one molecule, and is composed of the general formula SiO 1/2 unit and SiO 4/2 unit, and the molar ratio of SiO 1/2 unit / SiO 4/2 unit is 0.5 to 1. Organopolysiloxane resin (C) of .0, curing catalyst (D) required for addition reaction, and
Thioether-based antioxidant (E) having the following chemical formula I in the molecule
オルガノ水素ポリシロキサン（Ｂ）はオルガノポリシロキサン（Ａ）中のアルケニル基に対するオルガノ水素ポリシロキサン（Ｂ）のＳｉＨ基のモル比が０．５〜２０となる量であり、
チオエーテル系酸化防止剤（Ｅ）は組成物全体１００重量部に対して０．０２〜５重量部である、
ことを特徴とする粘着性シリコーン樹脂組成物。 The organopolysiloxane resin (C) is 10 to 90 parts by weight based on 100 parts by weight of the total number of the organopolysiloxane (A) and the organopolysiloxane resin (C).
The organohydrogen polysiloxane (B) is an amount such that the molar ratio of the SiH group of the organohydrogen polysiloxane (B) to the alkenyl group in the organopolysiloxane (A) is 0.5 to 20.
The thioether-based antioxidant (E) is 0.02 to 5 parts by weight based on 100 parts by weight of the entire composition.
An adhesive silicone resin composition.
A pressure-sensitive adhesive film obtained by applying the pressure-sensitive silicone resin composition according to claim 1 or 2 to form a silicone layer on at least one surface of a base film.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008274251A (en) * | 2007-03-30 | 2008-11-13 | Shin Etsu Chem Co Ltd | Solventless silicone pressure-sensitive adhesive composition |
| JP2011001448A (en) * | 2009-06-18 | 2011-01-06 | Shin-Etsu Chemical Co Ltd | Addition reaction-curing silicone adhesive composition and adhesive tape |
| JP2016122730A (en) * | 2014-12-25 | 2016-07-07 | 信越化学工業株式会社 | Wafer-processing body, tentatively-sticking material for wafer processing, and method for manufacturing thin wafer |
| JP2017179056A (en) * | 2016-03-29 | 2017-10-05 | アイカ工業株式会社 | Silicone adhesive composition and adhesive tape |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008274251A (en) * | 2007-03-30 | 2008-11-13 | Shin Etsu Chem Co Ltd | Solventless silicone pressure-sensitive adhesive composition |
| JP2011001448A (en) * | 2009-06-18 | 2011-01-06 | Shin-Etsu Chemical Co Ltd | Addition reaction-curing silicone adhesive composition and adhesive tape |
| JP2016122730A (en) * | 2014-12-25 | 2016-07-07 | 信越化学工業株式会社 | Wafer-processing body, tentatively-sticking material for wafer processing, and method for manufacturing thin wafer |
| JP2017179056A (en) * | 2016-03-29 | 2017-10-05 | アイカ工業株式会社 | Silicone adhesive composition and adhesive tape |
Cited By (1)
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|---|---|---|---|---|
| WO2023195268A1 (en) * | 2022-04-07 | 2023-10-12 | 信越化学工業株式会社 | Silicone pressure-sensitive adhesive composition, silicone pressure-sensitive adhesive, pressure-sensitive adhesive film, image display device, and method for evaluating silicone pressure-sensitive adhesive |
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