JP2022135773A - 二液硬化型ポリウレタン樹脂組成物 - Google Patents
二液硬化型ポリウレタン樹脂組成物 Download PDFInfo
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- JP2022135773A JP2022135773A JP2021035798A JP2021035798A JP2022135773A JP 2022135773 A JP2022135773 A JP 2022135773A JP 2021035798 A JP2021035798 A JP 2021035798A JP 2021035798 A JP2021035798 A JP 2021035798A JP 2022135773 A JP2022135773 A JP 2022135773A
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- Prior art keywords
- polyol
- polyurethane resin
- component
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- resin composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 239000011342 resin composition Substances 0.000 title claims abstract description 42
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- 229920005989 resin Polymers 0.000 claims abstract description 56
- 239000011347 resin Substances 0.000 claims abstract description 56
- 150000003505 terpenes Chemical class 0.000 claims abstract description 54
- 235000007586 terpenes Nutrition 0.000 claims abstract description 54
- 239000005062 Polybutadiene Substances 0.000 claims abstract description 37
- 229920002857 polybutadiene Polymers 0.000 claims abstract description 37
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 35
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 35
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- 235000019438 castor oil Nutrition 0.000 claims description 23
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- 239000000203 mixture Substances 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 239000005011 phenolic resin Substances 0.000 claims description 5
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- 239000000758 substrate Substances 0.000 description 8
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- -1 acrylic polyol Chemical class 0.000 description 5
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- 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 2
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- XSCLFFBWRKTMTE-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCC(CN=C=O)C1 XSCLFFBWRKTMTE-UHFFFAOYSA-N 0.000 description 1
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- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- AHBNSOZREBSAMG-UHFFFAOYSA-N 1,5-diisocyanato-2-methylpentane Chemical compound O=C=NCC(C)CCCN=C=O AHBNSOZREBSAMG-UHFFFAOYSA-N 0.000 description 1
- ATOUXIOKEJWULN-UHFFFAOYSA-N 1,6-diisocyanato-2,2,4-trimethylhexane Chemical compound O=C=NCCC(C)CC(C)(C)CN=C=O ATOUXIOKEJWULN-UHFFFAOYSA-N 0.000 description 1
- QGLRLXLDMZCFBP-UHFFFAOYSA-N 1,6-diisocyanato-2,4,4-trimethylhexane Chemical compound O=C=NCC(C)CC(C)(C)CCN=C=O QGLRLXLDMZCFBP-UHFFFAOYSA-N 0.000 description 1
- OEVVKKAVYQFQNV-UHFFFAOYSA-N 1-ethenyl-2,4-dimethylbenzene Chemical compound CC1=CC=C(C=C)C(C)=C1 OEVVKKAVYQFQNV-UHFFFAOYSA-N 0.000 description 1
- WTPYFJNYAMXZJG-UHFFFAOYSA-N 2-[4-(2-hydroxyethoxy)phenoxy]ethanol Chemical compound OCCOC1=CC=C(OCCO)C=C1 WTPYFJNYAMXZJG-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
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- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/69—Polymers of conjugated dienes
- C08G18/698—Mixtures with compounds of group C08G18/40
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
- C08G18/24—Catalysts containing metal compounds of tin
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/36—Hydroxylated esters of higher fatty acids
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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Abstract
Description
[1] ポリオールおよびテルペン樹脂を含む第1成分と、ポリイソシアネートを含む第2成分と、を含み、前記ポリオールは、ポリブタジエンポリオールおよび/または水添ポリブタジエンポリオールを30質量%以上含み、前記テルペン樹脂の含有量が、前記ポリオール100質量部に対して1~60質量部である、二液硬化型ポリウレタン樹脂組成物。
[2] 前記テルペン樹脂が、ポリテルペン樹脂、芳香族変性テルペン樹脂、およびテルペンフェノール樹脂からなる群から選択される少なくとも1種である、[1]に記載の二液硬化型ポリウレタン樹脂組成物。
[3] 前記ポリオールが、ひまし油系ポリオールをさらに含む、[1]または[2]に記載の二液硬化型ポリウレタン樹脂組成物。
[4] 電気電子部品封止用である、[1]~[3]のいずれか1項に記載の二液硬化型ポリウレタン樹脂組成物。
[5] [1]~[4]のいずれか1項に記載の二液硬化型ポリウレタン樹脂組成物を用いて樹脂封止された電気電子部品。
[6] 二液硬化型ポリウレタン樹脂組成物のポリオール成分として用いられるポリオール組成物であって、ポリオールおよびテルペン樹脂を含み、前記ポリオールは、ポリブタジエンポリオールおよび/または水添ポリブタジエンポリオールを30質量%以上含み、前記テルペン樹脂の含有量が、前記ポリオール100質量部に対して1~60質量部である、ポリオール組成物。
[ポリブタジエンポリオール(A1-1)および/または水添ポリブタジエンポリオール(A1-2)]
第1成分に含まれるポリオール(A)としては、ポリブタジエンポリオール(A1-1)および/または水添ポリブタジエンポリオール(A1-2)(以下、両者をまとめて「PBポリオール(A1)」ということがある。)が用いられる。
ポリオール(A)には、さらにひまし油系ポリオール(A2)が含まれてもよい。ひまし油系ポリオール(A2)としては、ひまし油、ひまし油脂肪酸、及びこれらに水素付加した水添ひまし油や水添ひまし油脂肪酸を用いて製造されたポリオールを使用することができる。より詳細には、ひまし油系ポリオール(A2)としては、例えば、ひまし油、ひまし油とその他の天然油脂とのエステル交換物、ひまし油と多価アルコールとの反応物、ひまし油脂肪酸と多価アルコールとのエステル化反応物、及びこれらにアルキレンオキサイドを付加重合したポリオールなどが挙げられる。
ポリオール(A)は、PBポリオール(A1)のみで構成されてもよく、PBポリオール(A1)およびひまし油系ポリオール(A2)のみで構成されてもよく、また、PBポリオール(A1)とともに他のポリオール(A3)を含有してもよく、PBポリオール(A1)およびひまし油系ポリオール(A2)とともに他のポリオール(A3)を含有してもよい。ポリオール(A)は、2官能のもののみで構成されてもよく、3官能以上のものを含んでもよいが、ポリイソシアネート(C)が2官能のもののみで構成される場合、ポリウレタン樹脂組成物を熱硬化性にするべく3官能以上のポリオールを含むことが好ましい。
本実施形態では、第1成分に、PBポリオール(A1)とともにテルペン樹脂(B)を用いる。テルペン樹脂(B)はPBポリオール(A1)との相溶性に優れるため、第1成分の分離や濁りを抑制することができる。また、PBポリオール(A1)とテルペン樹脂(B)を併用することにより、電子回路基板等との密着性を向上することができ、かつ、誘電率が低いポリウレタン樹脂を得ることができる。
第1成分には、上記した各成分の他に、必要に応じて、例えば、触媒、酸化防止剤、整泡剤、希釈剤、難燃剤、紫外線吸収剤、着色剤、充填剤、可塑剤などの各種添加剤を、本実施形態の目的を損なわない範囲で加えることができる。
[ポリイソシアネート(C)]
第2成分に含まれるポリイソシアネート(C)としては、特に限定されず、1分子中に2つ以上のイソシアネート基を有する種々のポリイソシアネート化合物を用いることができる。ポリイソシアネート(C)としては、例えば、脂肪族ポリイソシアネート化合物(C1)、脂環式ポリイソシアネート化合物(C2)、および芳香族ポリイソシアネート化合物(C3)、ならびにこれらの変性体および多核体が挙げられ、いずれか1種用いても2種以上併用してもよい。
第2成分はポリイソシアネート(C)のみで構成してもよく、また、ポリイソシアネート(C)の他に、必要に応じて、例えば、触媒、酸化防止剤、整泡剤、希釈剤、難燃剤、紫外線吸収剤、着色剤、充填剤、可塑剤などの各種添加剤を、本実施形態の目的を損なわない範囲で加えることができる。
本実施形態に係る二液硬化型ポリウレタン樹脂組成物は、通常は、第1成分としての第1液と第2成分としての第2液とで構成されるが、第1成分および第2成分の他に、任意成分としての上記その他の成分を含む第3成分を第3液として備えてもよい。
一実施形態に係るポリオール組成物は、二液硬化型ポリウレタン樹脂組成物のポリオール成分として用いられるものであり、上記第1成分がこれに相当する。そのため、該ポリオール組成物は、ポリオール(A)およびテルペン樹脂(B)を含み、該ポリオール(A)がポリブタジエンポリオールおよび/または水添ポリブタジエンポリオールを30質量%以上含み、テルペン樹脂(B)の含有量がポリオール(A)100質量部に対して1~60質量部である。ポリオール(A)、テルペン樹脂(B)およびその他の成分についての詳細は上述したとおりであり、説明は省略する。
本実施形態に係る二液硬化型ポリウレタン樹脂組成物の用途は、特に限定されないが、電気電子部品の封止のために用いられることが好ましい。電気電子部品としては、例えば、トランスコイル、チョークコイルおよびリアクトルコイルなどの変圧器、機器制御基板、センサ、無線通信部品などが挙げられる。該二液硬化型ポリウレタン樹脂組成物は、低誘電特性に優れ(すなわち誘電率が低く)電波の影響を受けにくいため、無線通信を行う無線通信部品を外部環境から保護するために当該無線通信部品を樹脂封止、すなわち被覆する封止材として用いられることが好ましく、例えば、検知した情報を無線通信により送信するセンサの封止材として用いてもよい。
・ポリブタジエンポリオール1:水酸基価47mgKOH/g、製品名:Poly bd R-45HT、出光興産(株)製
・ポリブタジエンポリオール2:水酸基価107mgKOH/g、製品名:Poly bd R-15HT、出光興産(株)製
・ポリブタジエンポリオール3:水酸基価49mgKOH/g、製品名:KRASOL LBH-2000、クレイバレー社製
・水添ポリブタジエンポリオール:水酸基価49mgKOH/g、製品名:KRASOL H-LBH-2000、クレイバレー社製
・ひまし油系ポリオール:水酸基価120mgKOH/g、製品名:HS2G-120、豊国製油(株)製
・ポリエーテルポリオール:水酸基価160mgKOH/g、製品名:G-1000、第一工業製薬(株)製
・テルペン樹脂1:リモネン・スチレン共重合体、有効成分50質量%、製品名:YSレジンLP、ヤスハラケミカル(株)製
・テルペン樹脂2:ピネン・ジペンテン共重合体、有効成分80質量%、製品名:ダイマロン、ヤスハラケミカル(株)製
・テルペン樹脂3:フェノール・α-ピネン共重合体、有効成分100質量%、製品名:YS POLYSTER T80、ヤスハラケミカル(株)製
・石油樹脂:東ソー(株)製、製品名:ペトロタック
[触媒]
・スズ系触媒:製品名:ネオスタンU-810、日東化成(株)製
・ポリイソシアネート1:ポリメリックMDI、製品名:ミリオネートMR-200、東ソー(株)製
・ポリイソシアネート2:カルボジイミド変性MDI、製品名:ルプラネートMM103、BASF INOAC ポリウレタン(株)製
・ポリイソシアネート3:イソシアヌレート変性HDI、製品名:デュラネートTPA-100、旭化成(株)製
下記表1および表2に示す配合(質量部)により、各実施例及び各比較例の二液硬化型ポリウレタン樹脂組成物を調製した。調製に際しては、表1および表2に示す第1成分を所定量秤量し、適宜熱をかけて溶かし込みながら攪拌混合を行い、混合後、25℃に調整した。続いて、この混合物に25℃に調整した第2成分(ポリイソシアネート(C))を表1および表2に記載のとおりに加えて攪拌混合し、脱泡した。
第1成分を混合した後の液の様子を確認して、テルペン樹脂または比較用樹脂とポリオール(A)との相溶性を、下記基準により評価した。
A:透明
B:若干の濁りあり
C:濁りあり
D:30分以上経過後に分離発生
E:30分未満で分離発生
市販されているFR-4エポキシ基板上に、上記脱泡後の二液硬化型ポリウレタン樹脂組成物を直径1cmほど垂らし、80℃にて16時間(一晩)養生し、硬化させた。硬化後のポリウレタン樹脂とエポキシ基板上の境目を狙い、カッターナイフにて樹脂を斫り、基板上に残ったポリウレタン樹脂を目視によって確認した。評価は、凝集破壊をポリウレタン樹脂部分が基板上に残っている状態、界面剥離を基板上からポリウレタン樹脂がはがれてしまう状態とし、両状態が混在している際は、その面積割合に応じて下記基準により評価を行った。
A:凝集破壊100%
B:凝集破壊が75%以上100%未満、界面剥離が0%超25%以下
C:凝集破壊が50%以上75%未満、界面剥離が25%超50%以下
D:凝集破壊が25%以上50%未満、界面剥離が50%超75%以下
E:凝集破壊が25%未満、界面剥離が75%以上
上記脱泡後の二液硬化型ポリウレタン樹脂組成物を厚み3mmの金型に流し、80℃にて16時間(一晩)養生し、3mm厚の樹脂シートを作製した。該樹脂シートを50mm×50mm×3mmのシートに切り分け、測定用サンプルとした。測定は、アジレント・テクノロジー(株)製の装置(本体の型式:E4980A、名称:Precision LCR Meter。電極部分の型式:16451B、名称:DIELECTRIC TEST FIXTURE)を用いて実施し、周波数1MHz時の誘電率(比誘電率)の値を測定した。
Claims (6)
- ポリオールおよびテルペン樹脂を含む第1成分と、
ポリイソシアネートを含む第2成分と、を含み、
前記ポリオールは、ポリブタジエンポリオールおよび/または水添ポリブタジエンポリオールを30質量%以上含み、
前記テルペン樹脂の含有量が、前記ポリオール100質量部に対して1~60質量部である、二液硬化型ポリウレタン樹脂組成物。 - 前記テルペン樹脂が、ポリテルペン樹脂、芳香族変性テルペン樹脂、およびテルペンフェノール樹脂からなる群から選択される少なくとも1種である、請求項1に記載の二液硬化型ポリウレタン樹脂組成物。
- 前記ポリオールが、ひまし油系ポリオールをさらに含む、請求項1または2に記載の二液硬化型ポリウレタン樹脂組成物。
- 電気電子部品封止用である、請求項1~3のいずれか1項に記載の二液硬化型ポリウレタン樹脂組成物。
- 請求項1~4のいずれか1項に記載の二液硬化型ポリウレタン樹脂組成物を用いて樹脂封止された電気電子部品。
- 二液硬化型ポリウレタン樹脂組成物のポリオール成分として用いられるポリオール組成物であって、
ポリオールおよびテルペン樹脂を含み、
前記ポリオールは、ポリブタジエンポリオールおよび/または水添ポリブタジエンポリオールを30質量%以上含み、
前記テルペン樹脂の含有量が、前記ポリオール100質量部に対して1~60質量部である、ポリオール組成物。
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