JP6495449B2 - ポリイソシアネート組成物、ポリウレタン樹脂および二液硬化型ポリウレタン組成物 - Google Patents
ポリイソシアネート組成物、ポリウレタン樹脂および二液硬化型ポリウレタン組成物 Download PDFInfo
- Publication number
- JP6495449B2 JP6495449B2 JP2017523662A JP2017523662A JP6495449B2 JP 6495449 B2 JP6495449 B2 JP 6495449B2 JP 2017523662 A JP2017523662 A JP 2017523662A JP 2017523662 A JP2017523662 A JP 2017523662A JP 6495449 B2 JP6495449 B2 JP 6495449B2
- Authority
- JP
- Japan
- Prior art keywords
- mass
- xylylene diisocyanate
- isocyanurate
- polyisocyanate
- derivative
- 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.)
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- 239000005056 polyisocyanate Substances 0.000 title claims description 120
- 229920001228 polyisocyanate Polymers 0.000 title claims description 120
- 239000000203 mixture Substances 0.000 title claims description 104
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- 229920002635 polyurethane Polymers 0.000 title claims description 15
- 239000004814 polyurethane Substances 0.000 title claims description 15
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical class OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 107
- 238000006243 chemical reaction Methods 0.000 claims description 89
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 claims description 62
- 229920005862 polyol Polymers 0.000 claims description 45
- 150000003077 polyols Chemical class 0.000 claims description 38
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical class NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims description 35
- 125000001931 aliphatic group Chemical group 0.000 claims description 34
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 29
- 238000002156 mixing Methods 0.000 claims description 20
- 238000005227 gel permeation chromatography Methods 0.000 claims description 9
- 239000004793 Polystyrene Substances 0.000 claims description 8
- 239000003607 modifier Substances 0.000 claims description 8
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- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 150000001298 alcohols Chemical group 0.000 description 50
- -1 xylylene diisocyanate polyol Chemical class 0.000 description 44
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- 239000003054 catalyst Substances 0.000 description 28
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 26
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- 238000000034 method Methods 0.000 description 23
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- 238000004821 distillation Methods 0.000 description 21
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- 239000000243 solution Substances 0.000 description 20
- 238000012986 modification Methods 0.000 description 19
- 230000004048 modification Effects 0.000 description 19
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 18
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 17
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 15
- 238000004519 manufacturing process Methods 0.000 description 15
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- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 14
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- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 11
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
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- 150000002513 isocyanates Chemical class 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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- 239000003963 antioxidant agent Substances 0.000 description 8
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 8
- 230000003287 optical effect Effects 0.000 description 8
- 239000003973 paint Substances 0.000 description 8
- 230000003078 antioxidant effect Effects 0.000 description 7
- 235000019437 butane-1,3-diol Nutrition 0.000 description 7
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 230000000704 physical effect Effects 0.000 description 7
- 239000003381 stabilizer Substances 0.000 description 7
- FWWWRCRHNMOYQY-UHFFFAOYSA-N 1,5-diisocyanato-2,4-dimethylbenzene Chemical compound CC1=CC(C)=C(N=C=O)C=C1N=C=O FWWWRCRHNMOYQY-UHFFFAOYSA-N 0.000 description 6
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 229910000831 Steel Inorganic materials 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 6
- 239000010959 steel Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000000853 adhesive Substances 0.000 description 5
- 230000001070 adhesive effect Effects 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 5
- 229920005906 polyester polyol Polymers 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 235000013772 propylene glycol Nutrition 0.000 description 5
- 229960004063 propylene glycol Drugs 0.000 description 5
- 150000003335 secondary amines Chemical class 0.000 description 5
- 239000010409 thin film Substances 0.000 description 5
- 239000013638 trimer Substances 0.000 description 5
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical class NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 5
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 4
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 4
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 125000002723 alicyclic group Chemical group 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 4
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 4
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- 229940059574 pentaerithrityl Drugs 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 4
- 239000004926 polymethyl methacrylate Substances 0.000 description 4
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 4
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- OHLKMGYGBHFODF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=C(CN=C=O)C=C1 OHLKMGYGBHFODF-UHFFFAOYSA-N 0.000 description 3
- ROHUXHMNZLHBSF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCC(CN=C=O)CC1 ROHUXHMNZLHBSF-UHFFFAOYSA-N 0.000 description 3
- SPSPIUSUWPLVKD-UHFFFAOYSA-N 2,3-dibutyl-6-methylphenol Chemical compound CCCCC1=CC=C(C)C(O)=C1CCCC SPSPIUSUWPLVKD-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 3
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
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Images
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- C08G18/80—Masked polyisocyanates
- C08G18/8003—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen
- C08G18/8006—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32
- C08G18/8009—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203
- C08G18/8012—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203 with diols
- C08G18/8019—Masked aromatic polyisocyanates
-
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- 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
- C08G18/80—Masked polyisocyanates
- C08G18/8003—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen
- C08G18/8006—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32
- C08G18/8009—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203
- C08G18/8022—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203 with polyols having at least three hydroxy groups
- C08G18/8029—Masked aromatic polyisocyanates
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- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
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Description
そして、反応混合液におけるアルコール変性率は、反応混合液におけるキシリレンジイソシアネートおよびイソシアヌレート誘導体に対するアルコール類の変性量であって、キシリレンジイソシアネートの仕込み質量に対するアルコール類の仕込み質量の配合割合として算出することができる。
イソシアヌレート誘導体の蒸留収率は、反応混合液(蒸留前液)およびイソシアヌレート誘導体(蒸留後液)の質量をそれぞれ測定し、下記式により反応混合液の質量に対するイソシアヌレート誘導体の質量の割合を算出することにより求めた。
<イソシアヌレート誘導体に対するアルコール類による変性量(イソシアヌレート誘導体のアルコール変性率)>
反応混合液における、キシリレンジイソシアネートおよびイソシアヌレート誘導体に対するアルコール類の変性量(反応混合液におけるアルコール変性率)は、キシリレンジイソシアネートの仕込み質量に対するアルコール類の仕込み質量として算出した。
<転化率(反応率)(%)>
反応液(反応混合液またはイソシアヌレート誘導体)中のイソシアネート基濃度を、JIS K−1603−1(2010年)に準拠して測定し、その減少率を求めることにより、イソシアネート基の転化率(反応率)を求めた。
イソシアヌレート誘導体のサンプルをゲルパーミエーションクロマトグラフィ(GPC)測定し、得られたクロマトグラム(チャート)において、ポリスチレン換算分子量400〜1000の間をピークトップとするピークの面積の、全ピークの面積に対する面積率から、3分子体面積率を求めた。
(1)分析装置 : Alliance(Waters)
(2)ポンプ : Alliance 2695(Waters)
(3)検出器 : 2414型示差屈折検出器(Waters)
(4)溶離液 : Tetrahydrofuran
(5)分離カラム :Plgel GUARD + Plgel 5μmMixed−C×3本(50×7.5mm,300×7.5mm)
メーカー ; Polymer Laboratories
品番 ; PL1110−6500
(6)測定温度 : 40℃
(7)流速 : 1mL/min
(8)サンプル注入量 : 100μL
(9)解析装置 : EMPOWERデータ処理装置(Waters)
・システム補正
(1)標準物質名 : Polystyrene
(2)検量線作成方法 : 分子量の異なるTOSOH社製 TSKstandard Polystyreneを用い、リテンションタイムと分子量のグラフを作成。
(3)注入量、注入濃度 : 100μL、 1mg/mL
なお、製造例4のキシリレンジイソシアネートのイソシアヌレート誘導体のゲルパーミエーションクロマトグラムを図1に示し、製造例9のキシリレンジイソシアネートのイソシアヌレート誘導体のゲルパーミエーションクロマトグラムを図2に示す。
製造例1
温度計、撹拌装置、窒素導入管および冷却管が装着された反応器に、窒素雰囲気下、1,3−キシリレンジイソシアネート(三井化学社製、m−XDI)100質量部と、2,6−ジ(tert-ブチル)−4−メチルフェノール(別名:ジブチルヒドロキシトルエン、BHT、ヒンダードフェノール系酸化防止剤(安定剤))0.025phrと、テトラフェニル・ジプロピレングリコール・ジホスファイト(JPP−100(商品名、城北化学工業社製)有機亜リン酸エステル、助触媒)0.05phrとを仕込んだ後、この仕込み液に、イソシアヌレート化触媒として、テトラブチルアンモニウムのハイドロオキサイド(TBAOH)の溶液(37%メタノール溶液)を0.04phr(固形分換算0.015phr)配合し、反応開始温度60℃で120分間反応させた。反応中の到達最高温度は、68℃であった。
表1に示す処方および製造条件に変更したこと以外は、製造例1と同様にして、キシリレンジイソシアネートのイソシアヌレート誘導体を得た。
温度計、撹拌装置、窒素導入管および冷却管が装着された反応器に、窒素雰囲気下、1,3−キシリレンジイソシアネート(三井化学社製、m−XDI)100質量部と、イルガノックス1076(Irg1076(商品名、チバ・ジャパン社製)ヒンダードフェノール系酸化防止剤)0.025phrと、トリデシルホスファイト(JP−310(商品名、城北化学工業社製)、脂肪族有機亜リン酸エステル、助触媒)0.05phrとを仕込んだ後、この仕込み液に、1,3−ブタンジオール4.00質量部を加え、仕込み液を75℃に昇温して、ウレタン化反応させた。1,3−ブタンジオールのヒドロキシ基に対する、1,3−キシリレンジイソシアネートのイソシアネート基の当量比(NCO/OH)は12であった。
Irg1076:イルガノックス1076、ヒンダードフェノール系酸化防止剤、チバ・ジャパン社製
BHT:2,6−ジ(tert-ブチル)−4−メチルフェノール(別名:ジブチルヒドロキシトルエン、ヒンダードフェノール系酸化防止剤
JP−310:トリデシルホスファイト、脂肪族有機亜リン酸エステル、助触媒、城北化学工業社製
JPP−100:テトラフェニル・ジプロピレングリコール・ジホスファイト、有機亜リン酸エステル、助触媒、城北化学工業社製
TBAOH:テトラブチルアンモニウムのハイドロオキサイドの溶液、溶媒プロピレングリコールモノメチルエーテルアセテート、濃度9.09質量%
1,3−BG:1,3−ブタンジオール
実施例1〜14、実施例16〜20、参考例15、参考例21および比較例1〜15
各製造例で得られたキシリレンジイソシアネートのイソシアヌレート誘導体、市販のキシリレンジイソシアネートのポリオール誘導体、市販の脂肪族ポリイソシアネート(ヘキサメチレンジイソシアネート)のビウレット誘導体、および、市販の脂肪族ポリイソシアネート(ヘキサメチレンジイソシアネート)の三量体を、表3〜表8に示す組み合わせおよび処方で配合し、ポリイソシアネート組成物を得た。
(塗工溶液の調製)
各実施例、各参考例および各比較例で得られたポリイソシアネート組成物を、酢酸エチルで希釈し、固形分75質量%の溶液を調製した。次いで、得られたポリイソシアネート組成物の溶液と、アクリルポリオール(三井化学社製、商品名:オレスターQ666、以下、Q666と略する。)とを、ポリイソシアネート組成物中のイソシアネート基に対するアクリルポリオール中の水酸基の当量比(NCO/OH)が1.0となる割合で配合し、シンナー(酢酸エチル/プロピレングリコールモノメチルエーテルアセテート/酢酸ブチルを重量比1:1:1で混合したもの)で、固形分50質量%になるように希釈した後に、23℃で5分間攪拌した。さらに、10分間超音波処理することにより、脱泡して、塗工溶液を得た。
(ウレタン皮膜の作製)
上記方法により得られた塗工溶液を、鋼板(SPCC、PBN−144処理品)およびポリメチルメタクリレート(PMMA)板上にそれぞれ乾燥膜厚が40μmになるように、ガラス板上に乾燥膜厚が100μmになるように、それぞれ塗工した。次いで、23℃で2時間乾燥後に、80℃で30分熱処理した。その後、23℃、相対湿度55%で7日間熟成することにより鋼板、PMMA板、およびガラス板上それぞれにウレタン皮膜を得た。
各実施例、各参考例および各比較例の塗工溶液およびウレタン皮膜を用いて、下記の物性についてそれぞれ評価した。
アプリケーターを用いて100μmの厚み(乾燥前厚み)になるように塗工溶液をガラス板上に塗工した。塗工後、23℃、相対湿度30%の条件下で、指で触った時にタックがなくなるまでの時間を測定した。
アプリケーターを用いて100μmの厚み(乾燥前厚み)になるように塗工溶液をガラス板上に塗工した。塗工後、23℃、相対湿度30%の条件下で、指を強く押し付けた時に指紋の跡がつかなくなるまでの時間を測定した。
ガラス板上に塗工したウレタン皮膜のヘイズを、ヘイズメーター(日本電色工業社製、NDH2000)にて評価した。
促進耐候性試験機(デューパネル光コントロールウェザーメーター、スガ試験機社製)にて、PMMA板上に塗工したウレタン皮膜を、昼間(60℃×相対湿度10%×4時間×光照射)、夜間(50℃×相対湿度95%×4時間×光照射なし)のサイクルで600時間処理した。処理前後のウレタン皮膜を色差計(日本電色工業社製、SE2000)にて評価し、処理前後の色差(ΔE)を算出した。また、光沢度を光沢度計(日本電色工業社製、VG2000)にて評価し、初期の光沢度を100としたときの光沢保持率(600時間後)を算出した。
鋼板上に塗工したウレタン皮膜を、デュポン式衝撃試験器の1/2インチの撃ち型と受け台との間に挟み、おもり(300g)を用いて、鋼板におけるウレタン皮膜が形成された面(表面)から衝撃を加え、ウレタン皮膜に損傷が現れるおもりの高さ(cm)を測定した。
JIS K 5600−5−2(1999年)に準拠して、鋼板上に塗工したウレタン皮膜表面と反対側とから20mm径の押し込み器をあて、鋼板をしっかり固定しておき、所定の速度で押し込み器を押し出しウレタン皮膜表面に割れ、剥れを生じた時の押し出し長さをエリクセン(mm)として評価した。
D−110N:キシリレンジイソシアネートのトリメチロールプロパン変性体、NCO基含有率:11.5質量%、固形分濃度:75質量%、溶剤:酢酸エチル、粘度(25℃):500mPa・s、三井化学社製
D−165N:ヘキサメチレンジイソシアネートのビウレット変性体、NCO基含有率:23.3質量%、固形分濃度:100質量%、粘度(25℃):2300mPa・s、三井化学社製
D−170N:ヘキサメチレンジイソシアネートの三量体、NCO基含有率:20.7質量%、固形分濃度:100質量%、粘度(25℃):2000mPa・s、三井化学社製
なお、上記発明は、本発明の例示の実施形態として提供したが、これは単なる例示に過ぎず、限定的に解釈してはならない。当該技術分野の当業者によって明らかな本発明の変形例は、後記特許請求の範囲に含まれる。
Claims (6)
- キシリレンジイソシアネートのイソシアヌレート誘導体と、
脂肪族ポリイソシアネートのビウレット誘導体と
を含有し、
前記キシリレンジイソシアネートのイソシアヌレート誘導体をゲルパーミエーションクロマトグラフ測定したときのクロマトグラムにおいて、ポリスチレン換算分子量400〜1000の間をピークトップとするピークの面積の、全ピークの面積に対する面積率が、35%以上80%以下である
ことを特徴とする、ポリイソシアネート組成物。 - 前記ポリイソシアネート組成物の総量100質量部に対して、
前記キシリレンジイソシアネートのイソシアヌレート誘導体の含有割合が5〜95質量部であり、
前記脂肪族ポリイソシアネートのビウレット誘導体の含有割合が95〜5質量部である
ことを特徴とする、請求項1に記載のポリイソシアネート組成物。 - 前記キシリレンジイソシアネートのイソシアヌレート誘導体が、
活性水素基含有化合物を変性剤として配合せずに、キシリレンジイソシアネートをイソシアヌレート化反応させた反応生成物であることを特徴とする、請求項1に記載のポリイソシアネート組成物。 - 前記キシリレンジイソシアネートのイソシアヌレート誘導体をゲルパーミエーションクロマトグラフ測定したときのクロマトグラムにおいて、ポリスチレン換算分子量400〜1000の間をピークトップとするピークの面積の、全ピークの面積に対する面積率が、40%以上70%以下である
ことを特徴とする、請求項1に記載のポリイソシアネート組成物。 - 請求項1に記載のポリイソシアネート組成物と、
活性水素基含有化合物と
の反応により得られることを特徴とする、ポリウレタン樹脂。 - 請求項1に記載のポリイソシアネート組成物を含有するポリイソシアネート成分と、
ポリオール成分と
を含むことを特徴とする、二液硬化型ポリウレタン組成物。
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