JP2022511239A - ジイソシアネートモノマー含量が低いイソシアネート基含有ポリマー - Google Patents
ジイソシアネートモノマー含量が低いイソシアネート基含有ポリマー Download PDFInfo
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- JP2022511239A JP2022511239A JP2021505241A JP2021505241A JP2022511239A JP 2022511239 A JP2022511239 A JP 2022511239A JP 2021505241 A JP2021505241 A JP 2021505241A JP 2021505241 A JP2021505241 A JP 2021505241A JP 2022511239 A JP2022511239 A JP 2022511239A
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- diisocyanate
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- 229920000642 polymer Polymers 0.000 title claims abstract description 120
- 125000005442 diisocyanate group Chemical group 0.000 title claims abstract description 55
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 title claims abstract description 50
- 239000000178 monomer Substances 0.000 title claims abstract description 24
- 239000000203 mixture Substances 0.000 claims abstract description 146
- 239000004814 polyurethane Substances 0.000 claims abstract description 55
- 229920002635 polyurethane Polymers 0.000 claims abstract description 53
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 52
- 229920000570 polyether Polymers 0.000 claims abstract description 52
- 238000000034 method Methods 0.000 claims abstract description 29
- 239000000853 adhesive Substances 0.000 claims abstract description 27
- 230000001070 adhesive effect Effects 0.000 claims abstract description 27
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000000576 coating method Methods 0.000 claims abstract description 14
- 238000000926 separation method Methods 0.000 claims abstract description 6
- -1 1,2-propyleneoxy groups Chemical group 0.000 claims description 59
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical group C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 38
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 29
- 239000000758 substrate Substances 0.000 claims description 25
- 150000001412 amines Chemical class 0.000 claims description 16
- 239000012948 isocyanate Substances 0.000 claims description 15
- 238000007789 sealing Methods 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 13
- 238000004821 distillation Methods 0.000 claims description 13
- 150000002513 isocyanates Chemical class 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
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- 238000011156 evaluation Methods 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 238000005304 joining Methods 0.000 claims description 3
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- 229910052757 nitrogen Inorganic materials 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 229920001451 polypropylene glycol Polymers 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
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- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 150000002009 diols Chemical class 0.000 description 9
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- 150000001875 compounds Chemical class 0.000 description 7
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
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- 238000012360 testing method Methods 0.000 description 6
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- 239000005058 Isophorone diisocyanate Substances 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 239000011324 bead Substances 0.000 description 5
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- 239000010408 film Substances 0.000 description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 description 5
- 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 5
- 238000004519 manufacturing process Methods 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 5
- JLEXUIVKURIPFI-UHFFFAOYSA-N tris phosphate Chemical compound OP(O)(O)=O.OCC(N)(CO)CO JLEXUIVKURIPFI-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 4
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- 150000001299 aldehydes Chemical class 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 239000004568 cement Substances 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
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- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
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- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- 238000004073 vulcanization Methods 0.000 description 4
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000004359 castor oil Substances 0.000 description 3
- 235000019438 castor oil Nutrition 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000004567 concrete Substances 0.000 description 3
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- 238000010276 construction Methods 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
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- 229910052742 iron Inorganic materials 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
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- 229920000647 polyepoxide Polymers 0.000 description 3
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- NSNIMHFJAMGNCZ-UHFFFAOYSA-N (3-hydroxy-2,2-dimethylpropyl) dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCC(C)(C)CO NSNIMHFJAMGNCZ-UHFFFAOYSA-N 0.000 description 2
- 0 *C(*)N=CC(*)(*)C(*)OC(*)=O Chemical compound *C(*)N=CC(*)(*)C(*)OC(*)=O 0.000 description 2
- 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 2
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 2
- SLAMLWHELXOEJZ-UHFFFAOYSA-N 2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- ZMSQJSMSLXVTKN-UHFFFAOYSA-N 4-[2-(2-morpholin-4-ylethoxy)ethyl]morpholine Chemical compound C1COCCN1CCOCCN1CCOCC1 ZMSQJSMSLXVTKN-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
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- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
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- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
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Abstract
Description
- このポリマーが、1.3重量%~1.9重量%の範囲のNCO含量と、
- 0.5重量%以下のモノマーであるジイソシアネートの含量を有していること、
- そして、少なくとも一種のモノマーである芳香族ジイソシアネートと、2.2~2.6の範囲の平均OH官能価及び25~32mgKOH/gの範囲のOH価を有するポリエーテルトリオールとを、少なくとも3/1のNCO/OH比で反応させ、次いで適切な分離方法によって、モノマーである芳香族ジイソシアネートの大部分を除去することにより、このポリマーが得られること。
nは、2又は3であり、
Aは、任意選択的にエーテル酸素を含み、28~6000g/molの範囲の分子量を有するn価のヒドロカルビル基であり、
R1及びR2は、それぞれ独立して、1~12個の炭素原子を有する一価のヒドロカルビル基であるか、又は、共に結合して、任意選択的に置換された、5~8個、好ましくは6個の炭素原子を有する炭素環式環の一部を構成する、4~12個の炭素原子を有する二価のヒドロカルビル基であり、
R3は、水素ラジカル、又は1~12個の炭素原子を有する、直鎖状若しくは分岐状の、アルキル、アリールアルキル、若しくはアルコキシカルボニル基であり、
R4は、水素ラジカル、又は1~20個の炭素原子を有する一価のヒドロカルビル基であり、そして
R5は、6~20個の炭素原子を有するアルキル又はアルコキシ基である]
- 無機若しくは有機の顔料、特には、二酸化チタン、酸化クロム、又は酸化鉄;
- 繊維、特には、ガラス繊維、炭素繊維、金属繊維、セラミック繊維、ポリマー繊維たとえば、ポリアミド繊維若しくはポリエチレン繊維、又は天然繊維たとえば、羊毛、セルロース、麻、若しくはサイザル麻;
- ナノ充填剤たとえば、グラフェン又はカーボンナノチューブ;
- 染料;
- 乾燥剤、特には、モレキュラーシーブ粉体、酸化カルシウム、高反応性イソシアネートたとえば、p-トシルイソシアネート、モノオキサゾリジンたとえば、Incozol(登録商標)2(Incorez製)、又はオルトギ酸エステル;
- 接着促進剤、特には、オルガノアルコキシシラン、特にはエポキシシランたとえば、特には、3-グリシドオキシプロピルトリメトキシシラン若しくは3-グリシドオキシプロピルトリエトキシシラン、(メタ)アクリロシラン、アンヒドリドシラン、カルバマトシラン、アルキルシラン、若しくはイミノシラン、又はこれらのシランのオリゴマーの形、又はチタネート;
- イソシアネート基の反応を加速するさらなる触媒、特にはスズ、亜鉛、ビスマス、鉄、アルミニウム、モリブデン、ジオキソモリブデン、チタン、ジルコニウム、若しくはカリウムの塩、石鹸、若しくは錯体、特にはスズ(II)2-エチルヘキサノエート、スズ(II)ネオデカノエート、亜鉛(II)アセテート、亜鉛(II)2-エチルヘキサノエート、亜鉛(II)ラウレート、亜鉛(II)アセチルアセトネート、アルミニウムラクテート、アルミニウムオレエート、ジイソプロポキシチタンビス(エチルアセトアセテート)又は酢酸カリウム;三級アミノ基を含む化合物、特にはN-エチルジイソプロピルアミン、N,N,N’,N’-テトラメチルアルキレンジアミン、ペンタメチルアルキレントリアミン、及びより高級なそれらの同族体、ビス(N,N-ジエチルアミノエチル)アジペート、トリス(3-ジメチルアミノプロピル)アミン、1,4-ジアザビシクロ[2.2.2]オクタン(DABCO)、1,8-ジアザビシクロ[5.4.0]ウンデス-7-エン(DBU)、1,5-ジアザビシクロ[4.3.0]ノネ-5-エン(DBN)、N-アルキルモルホリン、N,N’-ジメチルピペラジン;芳香族窒素化合物たとえば、4-ジメチルアミノピリジン、N-メチルイミダゾール、N-ビニルイミダゾール、若しくは1,2-ジメチルイミダゾール;有機アンモニウム化合物たとえば、ベンジルトリメチルアンモニウムヒドロキシド、若しくはアルコキシル化三級アミン;「遅延作用性(delayed action)」触媒と呼ばれているもの(それらは、公知の金属又はアミン触媒を変性したものである);
- レオロジー調節剤、特には増粘剤、特には層状シリケートたとえばベントナイト、ヒマシ油の誘導体、水素化ヒマシ油、ポリアミド、ポリアミドワックス、ポリウレタン、ウレア化合物、ヒュームドシリカ、セルロースエーテル、又は疎水化変性されたポリオキシエチレン;
- 溶媒、特には、アセトン、酢酸メチル、酢酸tert-ブチル、酢酸1-メトキシ-2-プロピル、3-エトキシプロピオン酸エチル、ジイソプロピルエーテル、ジエチレングリコールジエチルエーテル、エチレングリコールジエチルエーテル、エチレングリコールモノブチルエーテル、エチレングリコールモノ-2-エチルヘキシルエーテル、アセタールたとえば、プロピラール、ブチラール、2-エチルヘキシラール、ジオキソラン、グリセロールホルマール、又は2,5,7,10-テトラオキサウンデカン(TOU)、トルエン、キシレン、ヘプタン、オクタン、ナフサ、ホワイトスピリット、石油エーテル若しくはガソリン、特にはSolvesso(商標)グレード(Exxon製)、及びプロピレンカーボネート、ジメチルカーボネート、ブチロラクトン、N-メチルピロリドン、N-エチルピロリドン、p-クロロベンゾトリフルオリド、又はベンゾトリフルオリド;
- 天然樹脂、油脂たとえば、ロジン、セラック、アマニ油、ヒマシ油、又はダイズ油;
- 非反応性ポリマー、特には、特にはエチレン、プロピレン、ブチレン、イソブチレン、イソプレン、酢酸ビニル、又はアルキル(メタ)アクリレートを含む群からの不飽和モノマーのホモポリマー若しくはコポリマー、特にはポリエチレン(PE)、ポリプロピレン(PP)、ポリイソブチレン、エチレン-酢酸ビニルコポリマー(EVA)、又はアタクチックポリ-α-オレフィン(APAO);
- 難燃剤物質、特には先にも述べた水酸化アルミニウム又は水酸化マグネシウム充填剤、及びさらに特には、有機リン酸エステルたとえば、特に、リン酸トリエチル、リン酸トリクレジル、リン酸トリフェニル、リン酸ジフェニルクレジル、リン酸イソデシルジフェニル、リン酸トリス(1,3-ジクロロ-2-プロピル)、リン酸トリス(2-クロロエチル)、リン酸トリス(2-エチルヘキシル)、リン酸トリス(クロロイソプロピル)、リン酸トリス(クロロプロピル)、各種のイソプロピル化度のイソプロピル化リン酸トリフェニル、リン酸モノ-、ビス-、若しくはトリス-(イソプロピルフェニル)、レソルシノールビス(ジフェニルホスフェート)、ビスフェノールAビス(ジフェニルホスフェート)又はポリリン酸アンモニウム;
- 添加剤、特には濡れ剤、レベリング剤、消泡剤、脱気剤、酸化、熱、光、若しくはUV放射線に対する安定剤、又は殺虫剤;
又は、湿分硬化型ポリウレタン組成物において慣用されるさらなる物質。
- 20重量%~60重量%の本発明のポリマー、
- 20重量%~60重量%の充填剤、
- 0重量%~35重量%の可塑剤、
及び任意選択的に、さらなる構成成分、特には、オリゴマー性イソシアネート(イソシアネートオリゴマー)、ブロックトアミン(ブロック化アミン)、触媒、又はさらなるポリマー。
- ガラス、ガラスセラミック、コンクリート、モルタル、セメントスクリード、繊維セメント、特には繊維セメントボード、れんが、タイル、セッコウ、特にはセッコウボード若しくは無水物スクリード、又は天然の石材たとえば、花崗岩若しくは大理石;
- PCC(ポリマー変性セメントモルタル)又はECC(エポキシ樹脂変性セメントモルタル)をベースとする修理又は平坦化用コンパウンド物;
- 金属又は合金たとえば、アルミニウム、銅、鉄、鋼、非鉄金属(表面仕上げ金属又は合金たとえば、亜鉛メッキ若しくはクロムメッキした金属を含む);
- アスファルト又はビチューメン;
- 皮革、織物、紙、木材、樹脂たとえば、フェノール樹脂、メラミン樹脂又はエポキシ樹脂を用いて接合させた木材料、樹脂/織物の複合材料、又はさらなるポリマー複合材料と呼ばれている材料;
- プラスチックたとえば、硬質及び軟質のPVC、ポリカーボネート、ポリスチレン、ポリエステル、ポリアミド、PMMA、ABS、SAN、エポキシ樹脂、フェノール樹脂、PUR、POM、TPO、PE、PP、EPM、又はEPDM(いずれの場合においても、表面処理されていなくても、或いは、プラズマ、コロナ、若しくは火炎の手段により表面処理されていてもよい);
- 繊維強化プラスチック、たとえば炭素繊維強化プラスチック(CFP)、ガラス繊維強化プラスチック(GFP)、及びシートモールディングコンパウンド(SMC);
- 断熱フォーム、特には、EPS、XPS、PUR、PIR、ロックウール、ガラスウール、又は発泡ガラスから作られたもの;
- コーティング又はペイントされた基材、特には、ペインテッドタイル、コーテッドコンクリート、粉体塗装した金属若しくは合金、又はペインテッド金属シート;
- ペイント又はワニス、特には自動車のトップコート。
(i)前述の湿分硬化型ポリウレタン組成物を、
- 第一の基材に適用し、その組成物のオープンタイムの間に、その組成物を第二の基材と接触させるか、又は
- 第一の基材及び第二の基材に適用し、その組成物のオープンタイムの間に、その二つの基材を接合するか、又は
- 二つの基材の間に適用すること、
(ii)湿分と接触させることよって組成物を硬化させること。
(i)前述の湿分硬化型ポリウレタン組成物を基材に適用すること、
(ii)湿分と接触させることよって組成物を硬化させること。
粘度は、恒温のRheotec RC30 コーン-プレート粘度計(コーン直径:25mm、コーン角度:1度、コーンチップ-プレート間距離:0.05mm、剪断速度:10s-1)を用いて測定した。
725.0gのDesmophen(登録商標)5031 BTポリエーテルトリオール、及び275.0gのジフェニルメタン4,4’-ジイソシアネート(Desmodur(登録商標)44 MC L、Covestro製)を、公知の方法により80℃で反応させて、7.6重量%のNCO含量、6.5Pa・sの20℃での粘度、及び約20重量%のモノマー性ジフェニルメタン4,4’-ジイソシアネート含量を有するポリエーテルウレタンポリマーを得た。
724.0gのAcclaim(登録商標)6300ポリエーテルトリオール、及び276.0gのジフェニルメタン4,4’-ジイソシアネート(Desmodur(登録商標)44 MC L、Covestro製)を、公知の方法により80℃で反応させて、7.5重量%のNCO含量、9.9Pa・sの20℃での粘度、及び約20重量%のモノマー性ジフェニルメタン4,4’-ジイソシアネート含量を有するポリエーテルウレタンポリマーを得た。
682.9gのVoranol(登録商標)CP 4755ポリエーテルトリオール、及び317.0gのジフェニルメタン4,4’-ジイソシアネート(Desmodur(登録商標)44 MC L、Covestro製)を、公知の方法により80℃で反応させて、8.8重量%のNCO含量、5.1Pa・sの20℃での粘度、及び約25重量%のモノマー性ジフェニルメタン4,4’-ジイソシアネート含量を有するポリエーテルウレタンポリマーを得た。
727.0gのAcclaim(登録商標)4200ポリエーテルジオール、及び273.0gのジフェニルメタン4,4’-ジイソシアネート(Desmodur(登録商標)44 MC L、Covestro製)を、公知の方法により80℃で反応させて、7.6重量%のNCO含量、5.2Pa・sの20℃での粘度、及び約18重量%のモノマー性ジフェニルメタン4,4’-ジイソシアネート含量を有するポリエーテルウレタンポリマーを得た。
1000gのDynacoll(登録商標)7360ポリエーテルジオール及び142gのジフェニルメタン4,4’-ジイソシアネート(Desmodur(登録商標)44 MC L、Covestro製)を、公知の方法により80℃で反応させて、2.0重量%のNCO含量及び2.3重量%のモノマー性ジフェニルメタン4,4’-ジイソシアネート含量を有する、室温で固体のポリマーを得た。
アルジミン A1:N,N’-ビス(2,2-ジメチル-3-ラウロイルオキシプロピリデン)-3-アミノメチル-3,5,5-トリメチルシクロヘキシルアミン
最初に、100.0g(0.35mol)の2,2-ジメチル-3-ラウロイルオキシプロパナールを、窒素雰囲気下に丸底フラスコに仕込んだ。次いで、27.9g(0.16mol)の3-アミノメチル-3,5,5-トリメチルシクロヘキシルアミン(Vestamin(登録商標)IPD、Evonik製)を、よく撹拌しながら添加し、次いで80℃、10mbarの減圧下で揮発性成分を除去した。得られたものは、153mgKOH/gのアミン価(計算アルジミン当量367g/molに相当)を有する無色の液体であった。
組成物Z1~Z4:
それぞれの組成物では、表1に記載の成分を記載された量(単位:重量部)でプラネタリーミキサーの手段により、減圧下で湿分を排除しながら混合し、湿分を排除して貯蔵した。
それぞれの組成物では、表3に記載の成分を記載された量(単位:重量部)でプラネタリーミキサーの手段により、減圧下で湿分を排除しながら混合し、湿分を排除して貯蔵した。それぞれの組成物を、以下の手順で試験した。
「極めて良好(very good)」は、95%を超える凝集破壊(cohesive failure)を表し、
「良好(good)」は、75%~95%の凝集破壊を表し、
「中程度(moderate)」は、25%~75%の凝集破壊を表し、
「不十分(poor)」は、25%未満の凝集破壊を表し、そして
「接着せず(no adhesion)」は、0%の凝集破壊、すなわち100%の接着層破壊(adhesive failure)を表す。
Claims (13)
- イソシアネート基を含むポリエーテルウレタンポリマーであって、
- 1.3重量%~1.9重量%の範囲のNCO含量と、
- 0.5重量%以下のモノマーであるジイソシアネートの含量と、を有し、かつ
- 少なくとも一種のモノマーである芳香族ジイソシアネートと、2.2~2.6の範囲の平均OH官能価及び25~32mgKOH/gの範囲のOH価を有するポリエーテルトリオールとを、少なくとも3/1のNCO/OH比で反応させ、次いで適切な分離方法によって、モノマーである前記芳香族ジイソシアネートの大部分を除去することにより得られる
ことを特徴とするポリマー。 - 移動相としてのテトラヒドロフラン、屈折率検出器、及び200g/molからの評価を使って、ポリスチレン標準に対するゲル浸透クロマトグラフィーを用いて測定して、5000~15,000g/molの範囲の平均分子量Mnを有することを特徴とする、請求項1に記載のポリマー。
- モノマーである前記芳香族ジイソシアネートが、ジフェニルメタン4,4’-ジイソシアネートであることを特徴とする、請求項1又は2に記載のポリマー。
- 前記ポリエーテルトリオールが、25~32mgKOH/gの範囲のOH価を有し、かつすべての繰り返し単位を基準にして、80重量%~90重量%の1,2-プロピレンオキシ基及び10重量%~20重量%の1,2-エチレンオキシ基を有していることを特徴とする、請求項1~3のいずれか一項に記載のポリマー。
- 過剰なモノマーである前記ジイソシアネートを、蒸留法によって除去することを特徴とする、請求項1~4のいずれか一項に記載のポリマー。
- 前記NCO含量が、前記ポリエーテルトリオールのOH基1モルあたり1モルのモノマーであるジイソシアネートが付加したとして計算した理論的なNCO含量の、少なくとも80%、特には少なくとも85%であることを特徴とする、請求項1~5のいずれか一項に記載のポリマー。
- 組成物全体を基準にして0.1重量%未満のモノマーであるジイソシアネートの含量を有する湿分硬化型ポリウレタン組成物であって、請求項1~6のいずれか一項に記載のポリマーを含む、組成物。
- 10重量%~80重量%の範囲の、請求項1~6のいずれか一項に記載のポリマーの含量を有することを特徴とする、請求項7に記載の組成物。
- 少なくとも一種のブロック化アミンをさらに含むことを特徴とする、請求項7又は8に記載の組成物。
- イソシアネートオリゴマー、触媒、充填剤、及び可塑剤から選択される、少なくとも一種のさらなる構成成分をさらに含むことを特徴とする、請求項7~9のいずれか一項に記載の組成物。
- 以下の工程を含む、接着接合又はシーリングの方法:
(i)請求項7~10のいずれか一項に記載の組成物を、
- 第一の基材に適用し、かつ前記組成物のオープンタイムの間に、前記組成物を第二の基材と接触させるか、又は
- 第一の基材及び第二の基材に適用し、かつ前記組成物のオープンタイムの間に、前記二つの基材を接合するか、又は
- 二つの基材の間に適用すること、
(ii)湿分と接触させることよって前記組成物を硬化させること。 - 以下を含む、コーティング又はシーリングの方法:
(i)請求項7~10のいずれか一項に記載の組成物を基材に適用すること、
(ii)湿分と接触させることよって前記組成物を硬化させること。 - 請求項11又は12に記載の方法から得られる物品。
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WO2022261855A1 (en) * | 2021-06-16 | 2022-12-22 | Ddp Specialty Electronic Materials Us, Llc | One-component polyurethane adhesive |
CN113956436B (zh) * | 2021-11-09 | 2023-05-30 | 万华化学(宁波)有限公司 | 一种浅色且存储过程中色号稳定的二苯基甲烷二异氰酸酯组合物 |
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