JP6863751B2 - 粘着剤および、粘着剤製造方法 - Google Patents
粘着剤および、粘着剤製造方法 Download PDFInfo
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- JP6863751B2 JP6863751B2 JP2017002531A JP2017002531A JP6863751B2 JP 6863751 B2 JP6863751 B2 JP 6863751B2 JP 2017002531 A JP2017002531 A JP 2017002531A JP 2017002531 A JP2017002531 A JP 2017002531A JP 6863751 B2 JP6863751 B2 JP 6863751B2
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- Prior art keywords
- pressure
- monool
- sensitive adhesive
- adhesive
- prepolymer
- Prior art date
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- 230000001070 adhesive effect Effects 0.000 title claims description 54
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- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 68
- 229920006295 polythiol Polymers 0.000 claims description 43
- 125000000524 functional group Chemical group 0.000 claims description 26
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 22
- 229920005862 polyol Polymers 0.000 claims description 20
- 150000003077 polyols Chemical class 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 16
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- 238000006243 chemical reaction Methods 0.000 claims description 8
- 230000001678 irradiating effect Effects 0.000 claims description 6
- 230000009257 reactivity Effects 0.000 claims 8
- 238000002360 preparation method Methods 0.000 claims 1
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- -1 aromatic isocyanates Chemical class 0.000 description 24
- 238000000034 method Methods 0.000 description 21
- 239000006260 foam Substances 0.000 description 20
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- 238000011156 evaluation Methods 0.000 description 13
- 238000002156 mixing Methods 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 12
- 230000000704 physical effect Effects 0.000 description 12
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
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- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
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- 239000012948 isocyanate Substances 0.000 description 7
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
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- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
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- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
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- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 4
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- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
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- 239000012975 dibutyltin dilaurate Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
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- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 2
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 2
- PFNHSEQQEPMLNI-UHFFFAOYSA-N 2-methyl-1-pentanol Chemical compound CCCC(C)CO PFNHSEQQEPMLNI-UHFFFAOYSA-N 0.000 description 2
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- HMBNQNDUEFFFNZ-UHFFFAOYSA-N 4-ethenoxybutan-1-ol Chemical compound OCCCCOC=C HMBNQNDUEFFFNZ-UHFFFAOYSA-N 0.000 description 2
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229920002799 BoPET Polymers 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
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- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 229920005830 Polyurethane Foam Polymers 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- JOBBTVPTPXRUBP-UHFFFAOYSA-N [3-(3-sulfanylpropanoyloxy)-2,2-bis(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS JOBBTVPTPXRUBP-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
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- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
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- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 2
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Description
図4〜図7に示す配合の原料から、実施例1〜14の粘着剤および比較例1〜4の粘着剤を製造した。以下に、各原料の詳細を示す。
・ポリオールb;ポリプロピレングリコール(PPG)、商品名:アクトコールD1000(Mw:1000)、三井化学(株)製
・ポリオールc;2−ブチル−2−エチル−1,3−プロパンジオール、商品名:BEPD(Mw:160.3)、Perstorp製
・ポリイソシアネート;TDI、商品名:ルプラネートT−80(Mw:174.2)、BASF製
・モノオール;2−エチルヘキシルグリコール、商品名:EHG(Mw:174.3)、日本乳化剤(株)製
・アクリレート;ヒドロキシエチルアクリレート(Mw:116.1)、大阪有機化学工業(株)製
・ビニルエーテル;ヒドロキシブチルビニルエーテル(Mw:116.2)、日本カーバイド(株)製
・アリルエーテル;ヒドロキシエチルアリルエーテル(Mw:102.13)、日本乳化剤(株)製
・ポリチオールB;官能基数4、ペンタエリスリトールテトラキス、商品名:PEMP(Mw:488.6)、SC有機化学(株)製
・ポリチオールC;官能基数6、ジペンタエリスリトールヘキサキス、商品名:DPMP(Mw:783.0)、SC有機化学(株)製
・粘着付与剤;ロジン系粘着付与剤、商品名:スーパーエステルA100、荒川化学工業(株)製
上述のように製造された実施例1〜14の粘着剤(両面テープ)、および、比較例1〜4の粘着剤(両面テープ)に対して、以下の方法によって物性評価を行なった。
Claims (5)
- ウレタンプレポリマーと、チオール基を有するポリチオールと、粘着付与剤とからなる組成物を用いて作成される粘着剤であって、
前記ウレタンプレポリマーが、
ラジカル反応性を有するモノオールと、ラジカル反応性を有しないモノオールと、ポリオールと、ポリイソシアネートとからなる組成物を用いて作成され、
前記ラジカル反応性を有しないモノオールのモル数に対する前記ラジカル反応性を有するモノオールのモル数の比率が、0.8〜3.5であり、
前記ウレタンプレポリマーの重量平均分子量が、2500〜22000であることを特徴とする粘着剤。 - 前記ラジカル反応性を有する官能基の全当量数に対する前記ポリチオールが有するチオール基の全当量数の比率が、0.8〜2.3であることを特徴とする請求項1に記載の粘着剤。
- 前記ポリチオールの平均官能基数が、2.5以上であることを特徴とする請求項1または請求項2に記載の粘着剤。
- 前記粘着付与剤の量が、前記ウレタンプレポリマー100重量部に対して、1〜30重量部であることを特徴とする請求項1ないし請求項3のいずれか1つに記載の粘着剤。
- ラジカル反応性を有するモノオールと、ラジカル反応性を有しないモノオールと、ポリオールと、ポリイソシアネートとを用いて、ウレタンプレポリマーを作成する作成工程と、
前記ウレタンプレポリマーと、チオール基を有するポリチオールと、粘着付与剤とを混合したものに、光を照射する照射工程と
を含み、
前記ラジカル反応性を有しないモノオールのモル数に対する前記ラジカル反応性を有するモノオールのモル数の比率が、0.8〜3.5であり、
前記ウレタンプレポリマーの重量平均分子量が、2500〜22000であり、
光重合反応により粘着剤を製造する粘着剤製造方法。
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