JP6637207B1 - 濡れ性向上剤 - Google Patents
濡れ性向上剤 Download PDFInfo
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- JP6637207B1 JP6637207B1 JP2019068410A JP2019068410A JP6637207B1 JP 6637207 B1 JP6637207 B1 JP 6637207B1 JP 2019068410 A JP2019068410 A JP 2019068410A JP 2019068410 A JP2019068410 A JP 2019068410A JP 6637207 B1 JP6637207 B1 JP 6637207B1
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- ammonium ion
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- 239000000080 wetting agent Substances 0.000 title claims abstract description 5
- -1 phosphate ester ion Chemical class 0.000 claims abstract description 143
- 150000003839 salts Chemical class 0.000 claims abstract description 59
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 41
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 35
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 6
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims abstract description 6
- 229910019142 PO4 Inorganic materials 0.000 claims abstract description 3
- 239000010452 phosphate Substances 0.000 claims abstract description 3
- 150000002500 ions Chemical class 0.000 claims description 32
- 229920000642 polymer Polymers 0.000 claims description 20
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 8
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- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 4
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
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- 150000001252 acrylic acid derivatives Chemical class 0.000 description 6
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 6
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 6
- 229910052753 mercury Inorganic materials 0.000 description 6
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- 229940085991 phosphate ion Drugs 0.000 description 6
- 229920002647 polyamide Polymers 0.000 description 6
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 5
- 239000004925 Acrylic resin Substances 0.000 description 5
- 229920000178 Acrylic resin Polymers 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000004734 Polyphenylene sulfide Substances 0.000 description 5
- 229920001971 elastomer Polymers 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 229920005672 polyolefin resin Polymers 0.000 description 5
- 229920000069 polyphenylene sulfide Polymers 0.000 description 5
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000012719 thermal polymerization Methods 0.000 description 5
- DCNHQNGFLVPROM-QXMHVHEDSA-N (z)-n,n-dimethyloctadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN(C)C DCNHQNGFLVPROM-QXMHVHEDSA-N 0.000 description 4
- OADIZUFHUPTFAG-UHFFFAOYSA-N 2-[2-(2-ethylhexoxy)ethoxy]ethanol Chemical compound CCCCC(CC)COCCOCCO OADIZUFHUPTFAG-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 239000012965 benzophenone Substances 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 238000001723 curing Methods 0.000 description 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 4
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- 239000000806 elastomer Substances 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
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- 125000001453 quaternary ammonium group Chemical class 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
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- AKACRNIHUAEVAW-KHPPLWFESA-N (z)-n-methyloctadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCNC AKACRNIHUAEVAW-KHPPLWFESA-N 0.000 description 3
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- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
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- WZYYQKWAHFYHLI-UHFFFAOYSA-N n,n-dimethyloctadecan-2-amine Chemical compound CCCCCCCCCCCCCCCCC(C)N(C)C WZYYQKWAHFYHLI-UHFFFAOYSA-N 0.000 description 1
- SPTCUDGTCPPMGY-UHFFFAOYSA-N n,n-dimethyloctadecan-3-amine Chemical compound CCCCCCCCCCCCCCCC(CC)N(C)C SPTCUDGTCPPMGY-UHFFFAOYSA-N 0.000 description 1
- GUZMHAGBKLERCD-UHFFFAOYSA-N n,n-dimethyloctadecan-5-amine Chemical compound CCCCCCCCCCCCCC(N(C)C)CCCC GUZMHAGBKLERCD-UHFFFAOYSA-N 0.000 description 1
- VXRNYQMFDGOGSI-UHFFFAOYSA-N n-(1,3-dihydroxy-2-methylpropan-2-yl)-2-[[1-[(1,3-dihydroxy-2-methylpropan-2-yl)amino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCC(C)(CO)NC(=O)C(C)(C)N=NC(C)(C)C(=O)NC(C)(CO)CO VXRNYQMFDGOGSI-UHFFFAOYSA-N 0.000 description 1
- WVFLGSMUPMVNTQ-UHFFFAOYSA-N n-(2-hydroxyethyl)-2-[[1-(2-hydroxyethylamino)-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCO WVFLGSMUPMVNTQ-UHFFFAOYSA-N 0.000 description 1
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- DFFZOPXDTCDZDP-UHFFFAOYSA-N naphthalene-1,5-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1C(O)=O DFFZOPXDTCDZDP-UHFFFAOYSA-N 0.000 description 1
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
- MNZMMCVIXORAQL-UHFFFAOYSA-N naphthalene-2,6-diol Chemical compound C1=C(O)C=CC2=CC(O)=CC=C21 MNZMMCVIXORAQL-UHFFFAOYSA-N 0.000 description 1
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
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- 239000002736 nonionic surfactant Substances 0.000 description 1
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- XNTUJOTWIMFEQS-UHFFFAOYSA-N octadecanoyl octadecaneperoxoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCCCCCCCC XNTUJOTWIMFEQS-UHFFFAOYSA-N 0.000 description 1
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- HPAFOABSQZMTHE-UHFFFAOYSA-N phenyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)C1=CC=CC=C1 HPAFOABSQZMTHE-UHFFFAOYSA-N 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
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- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
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- NMOALOSNPWTWRH-UHFFFAOYSA-N tert-butyl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)C NMOALOSNPWTWRH-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
Q+は、炭素数18の飽和又は不飽和の炭化水素基を有するアンモニウムイオンからなる群から選択される少なくとも1種であり、
T−は、下記式(2)で表される基を有する、リン酸エステルイオン、硫酸エステルイオン、及びスルホン酸イオンからなる群から選択される少なくとも1種である;
A1は、炭素数2〜4のアルキレン基を表し、
nは、1〜50の整数を表す。
本発明の濡れ性向上剤は、以下に示すイオン結合性塩またはその重合体を含む。
(イオン結合性塩の構造)
本発明の濡れ性向上剤に含まれるイオン結合性塩は、下記式(1)で表される。
Q+は、炭素数18の炭化水素基を有するアンモニウムイオンである。炭素数18の炭化水素基は、飽和又は不飽和のいずれであってもよいが、高い親水性付与効果を発揮できることから、不飽和炭化水素基であることが好ましい。
上記イオン結合性塩の製造方法は、特に制限されず、例えば、アニオン交換法、中和法、酸エステル法などが挙げられる。また、硫酸エステルのアンモニウム塩またはスルホン酸のアンモニウム塩と、窒素含有化合物とを反応させアンモニアを留去してイオン結合性塩を得る脱アンモニア法なども好適に用いられる。
本発明の一実施形態に係る濡れ性向上剤は、T−がエチレン性不飽和結合を有する上記イオン結合性塩由来の構成単位を有する重合体を含む。当該重合体は、イオン結合性塩の単独重合体またはイオン結合性塩およびその他のモノマーの共重合体のいずれであってもよい。
上記重合体は、イオン結合性塩、ならびに必要に応じて他のモノマー、溶媒、添加剤等を混合し、加熱あるいは(紫外線等の)光照射等により重合させて得ることができる。重合方法は特に制限されず、高圧ラジカル重合法、中低圧重合法、溶液重合法、スラリー重合法、塊状重合法、乳化重合法、気相重合法等の公知の方法を用いることができる。
本発明は、上記の濡れ性向上剤と、樹脂と、を含む樹脂組成物についても提供する。樹脂としては、熱可塑性樹脂または/および熱硬化性樹脂が好ましく、熱可塑性樹脂がより好ましい。以下、各樹脂について説明する。なお、本明細書において、「樹脂」との語には、モノマー、オリゴマー、プレポリマーおよびポリマーが包含される。
本発明で用いられる熱可塑性樹脂は、特に制限されないが、例えば、(メタ)アクリル樹脂、スチレン樹脂、オレフィン樹脂(環状オレフィン樹脂を含む)、ポリエステル樹脂、ポリカーボネート樹脂、ポリアミド樹脂、ポリフェニレンエーテル樹脂、ポリフェニレンスルフィド樹脂、ハロゲン含有樹脂(ポリ塩化ビニル、ポリ塩化ビニリデン、フッ素樹脂など)、ポリスルホン樹脂(ポリエーテルスルホン、ポリスルホンなど)、セルロース誘導体(セルロースエステル類、セルロースカーバメート類、セルロースエーテル類など)、シリコーン樹脂(ポリジメチルシロキサン、ポリメチルフェニルシロキサンなど)、ポリ酢酸ビニルなどのポリビニルエステル樹脂、ポリビニルアルコール樹脂およびこれらの誘導体樹脂、ゴムまたはエラストマー(ポリブタジエン、ポリイソプレンなどのジエンゴム、スチレン−ブタジエン共重合体、アクリロニトリル−ブタジエン共重合体、アクリルゴム、ウレタンゴム、シリコーンゴムなど)などが挙げられる。上記熱可塑性樹脂は、単独でもまたは2種以上組み合わせても使用することができる。
本発明で用いられる熱硬化性樹脂は、特に制限されないが、例えば、フェノール樹脂、ユリア樹脂、メラミン樹脂、エポキシ樹脂、不飽和ポリエステル樹脂、シリコーン樹脂、ポリウレタン樹脂、ポリイミド樹脂、ジアリルフタレート樹脂などが挙げられる。上記熱硬化性樹脂は、合成品を用いてもよいし、市販品を用いてもよい。
本発明の濡れ性向上剤およびこれを含む樹脂組成物は、親水化コーティング剤として好適に使用できる。具体的には、本発明の濡れ性向上剤または樹脂組成物からなる親水化コーティング剤を成形品の表面に塗布して乾燥または硬化させることで、成形品表面に親水性塗膜が形成される。得られる親水性塗膜の表面は、親水性に優れ、例えば、水に対する接触角が、好ましくは35°以下、より好ましくは20°以下、さらにより好ましくは10°以下、特に好ましくは5°以下、最も好ましくは5°未満である。ゆえに、上記親水性塗膜が表面に配置された成形品は、親水性ひいては耐汚染性に優れる。
[試験片の作製]
上記で合成した各イオン結合性塩を用いて、親水性塗膜を有する試験片を下記の手順で作製した。
[接触角測定]
上記実施例で得られた樹脂組成物について、水の接触角を測定した。接触角計を用い、乾燥状態(25℃/50%RH)で、液体として純水を使用して約1μLの液滴を針先に作り、これを樹脂組成物の表面に接触させて樹脂組成物上に液滴を作った。着滴後30秒後に接触角を測定し、親水性塗膜と液体とが接する点における、液体表面に対する接線と親水性塗膜の表面とがなす角で、液体を含む側の角度を接触角とした。
Claims (10)
- 下記式(1)で示されるイオン結合性塩を含む、濡れ性向上剤;
式(1)中、
Q+は、炭素数18の炭化水素基を有する、第一級アンモニウムイオン(N + RH 3 )、第二級アンモニウムイオン(N + R 2 H 2 )、及び第三級アンモニウムイオン(N + R 3 H)からなる群から選択される少なくとも1種であり、
T−は、下記式(2)で表される基を有する、リン酸エステルイオン、及び硫酸エステルイオンからなる群から選択される少なくとも1種である;
式(2)中、
A1は、炭素数2〜4のアルキレン基を表し、
nは、1〜50の整数を表す。 - 前記式(1)中、前記炭化水素基は、不飽和炭化水素基である、請求項1に記載の濡れ性向上剤。
- 前記式(1)中、前記炭化水素基は、オレイル基である、請求項1又は2に記載の濡れ性向上剤。
- 前記式(1)中、Q+は、第三級アンモニウムイオンである、請求項1〜3のいずれか1項に記載の濡れ性向上剤。
- 前記式(1)中、Q+は、ジアルキルオレイルアンモニウムイオンである、請求項1〜4のいずれか1項に記載の濡れ性向上剤。
- 前記式(1)中、Q+は、ジメチルオレイルアンモニウムイオンである、請求項1〜5のいずれか1項に記載の濡れ性向上剤。
- 前記式(1)中、T−は、リン酸エステルイオンである、請求項1〜6のいずれか1項に記載の濡れ性向上剤。
- 前記式(2)中、A1は、エチレン基、プロピレン基、及びエチルエチレン基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1〜7のいずれか1項に記載の濡れ性向上剤。
- 前記T−は、エチレン性不飽和結合を有する、請求項1〜8のいずれか1項に記載の濡れ性向上剤。
- 請求項9に記載のイオン結合性塩由来の構成単位を有する重合体を含む、濡れ性向上剤。
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