JP2020527187A - (環式)脂肪族ジイソシアネートのポリイソシアネートを含有する色安定性硬化剤組成物 - Google Patents
(環式)脂肪族ジイソシアネートのポリイソシアネートを含有する色安定性硬化剤組成物 Download PDFInfo
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- JP2020527187A JP2020527187A JP2020502326A JP2020502326A JP2020527187A JP 2020527187 A JP2020527187 A JP 2020527187A JP 2020502326 A JP2020502326 A JP 2020502326A JP 2020502326 A JP2020502326 A JP 2020502326A JP 2020527187 A JP2020527187 A JP 2020527187A
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- Prior art keywords
- group
- polyisocyanate
- polyisocyanate composition
- acid
- tert
- Prior art date
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- 229920001228 polyisocyanate Polymers 0.000 title claims abstract description 127
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- PJMDLNIAGSYXLA-UHFFFAOYSA-N 6-iminooxadiazine-4,5-dione Chemical group N=C1ON=NC(=O)C1=O PJMDLNIAGSYXLA-UHFFFAOYSA-N 0.000 claims description 3
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- 229910021488 crystalline silicon dioxide Inorganic materials 0.000 description 1
- NLCKLZIHJQEMCU-UHFFFAOYSA-N cyano prop-2-enoate Chemical class C=CC(=O)OC#N NLCKLZIHJQEMCU-UHFFFAOYSA-N 0.000 description 1
- 150000003997 cyclic ketones Chemical class 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- DTPCFIHYWYONMD-UHFFFAOYSA-N decaethylene glycol Polymers OCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO DTPCFIHYWYONMD-UHFFFAOYSA-N 0.000 description 1
- DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical class CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 description 1
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- SEGLCEQVOFDUPX-UHFFFAOYSA-N di-(2-ethylhexyl)phosphoric acid Chemical compound CCCCC(CC)COP(O)(=O)OCC(CC)CCCC SEGLCEQVOFDUPX-UHFFFAOYSA-N 0.000 description 1
- PNOXNTGLSKTMQO-UHFFFAOYSA-L diacetyloxytin Chemical compound CC(=O)O[Sn]OC(C)=O PNOXNTGLSKTMQO-UHFFFAOYSA-L 0.000 description 1
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- 235000014113 dietary fatty acids Nutrition 0.000 description 1
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- 239000003085 diluting agent Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- PLSFNSJUKGEOSL-UHFFFAOYSA-N dioctoxy(oxo)phosphanium Chemical compound CCCCCCCCO[P+](=O)OCCCCCCCC PLSFNSJUKGEOSL-UHFFFAOYSA-N 0.000 description 1
- CELQKAGZRYFGIL-UHFFFAOYSA-N diphosphanium difluoride Chemical compound [F-].[F-].[PH4+].[PH4+] CELQKAGZRYFGIL-UHFFFAOYSA-N 0.000 description 1
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- GLVVKKSPKXTQRB-UHFFFAOYSA-N ethenyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC=C GLVVKKSPKXTQRB-UHFFFAOYSA-N 0.000 description 1
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- 150000002923 oximes Chemical class 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
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- DYKKZVSISRMJIL-UHFFFAOYSA-N phenol;2,4,6-tritert-butylphenol Chemical compound OC1=CC=CC=C1.CC(C)(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 DYKKZVSISRMJIL-UHFFFAOYSA-N 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
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- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
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- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
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- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical compound C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 238000010345 tape casting Methods 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 150000005201 tetramethylbenzenes Chemical class 0.000 description 1
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- 150000003606 tin compounds Chemical class 0.000 description 1
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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 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000723 toxicological property Toxicity 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
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- 150000005199 trimethylbenzenes Chemical class 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- VNTDZUDTQCZFKN-UHFFFAOYSA-L zinc 2,2-dimethyloctanoate Chemical compound [Zn++].CCCCCCC(C)(C)C([O-])=O.CCCCCCC(C)(C)C([O-])=O VNTDZUDTQCZFKN-UHFFFAOYSA-L 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
-
- 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
- C08G18/244—Catalysts containing metal compounds of tin tin salts of carboxylic acids
- C08G18/246—Catalysts containing metal compounds of tin tin salts of carboxylic acids containing also tin-carbon bonds
-
- 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
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
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Abstract
Description
−(A)少なくとも1種のモノメリックイソシアネートの反応により得ることができる、少なくとも1種の(環式)脂肪族ポリイソシアネート、
−(B)40℃未満の融点および650〜2550g/molの数平均分子量Mnを有し、少なくとも2個のフェノール性基を有する、少なくとも1種の立体障害フェノール、
−(C)イソシアネート基と、イソシアネートに対して反応性の基との反応を促進することができる、少なくとも1種のルイス酸性有機金属化合物、
−(D)少なくとも1種の溶剤、
−(E)任意に、少なくとも1種のさらなる酸化防止剤、
−(F)任意に、4未満のpKa値を有する、少なくとも1種のブレンステッド酸、
−(G)任意に、その他の塗料添加剤
を含有する、ポリイソシアネート組成物によって解決された。
そのような化合物の平均NCO官能性は、通例、少なくとも1.8であり、8まで、好ましくは2〜5および特に好ましくは2.4〜4であってよい。
1) 脂肪族および/または環式脂肪族ジイソシアネートのイソシアヌレート基含有ポリイソシアネート。特に好ましいのは、この場合に、ヘキサメチレンジイソシアネートおよびイソホロンジイソシアネートをベースとするジイソシアネートである。その際に存在するイソシアヌレートは、殊に、該ジイソシアネートの環状三量体であるトリスイソシアナトアルキルイソシアヌレートもしくはトリスイソシアナトシクロアルキルイソシアヌレートであるか、またはそれらと、1個を上回るイソシアヌレート環を有する、より高次の同族体との混合物である。該イソシアナトイソシアヌレートは、一般に、10〜30質量%、殊に15〜25質量%のNCO含有率および2.6〜8の平均NCO官能性を有する。
該イソシアヌレート基含有ポリイソシアネートは、より少ない範囲で、アロファネート基および/またはウレタン基も、好ましくは該ポリイソシアネートを基準として2%未満の結合したアルコール含有率で、有していてよい。
該ウレトジオン基含有ポリイソシアネートはしばしば、その他のポリイソシアネート、殊に1)のもとに挙げられたものとの混合物で得られる。ウレトジオン基含有ポリイソシアネートは、通常、2〜3の官能性を有する。
これは、任意の組成のウレトジオン/イソシアヌレート混合物も、殊に、1〜40%、殊に3〜15%、殊に5〜10%のモノメリックウレトジオン(二量体)含有率で、含む。
そのためには、該ジイソシアネートは、ウレトジオン基ならびにその他のポリイソシアネートが形成されるか、または最初に該ウレトジオン基が形成され、かつこれらが続いてその他のポリイソシアネートに変換されるか、または該ジイソシアネートが最初にその他のポリイソシアネートに変換され、かつこれらが続いてウレトジオン基含有生成物に変換される反応条件下で変換することができる。
これらのアロファネート基および/またはウレタン基含有ポリイソシアネートはしばしば、1)のもとに挙げられたポリイソシアネートとの混合形で生じる。
Rは、線状または分岐状であり、かつ繰返し単位[−CH2−R−O−]から繰返し単位[−CH2−R−O−]まで異なっていてよい、任意に置換されたC1〜C5−アルキル基であり、好ましくはR=−CH2−、−(CH2)2−、−CH(CH3)−および−(CH2)3−から選択され、より好ましくは各繰返し単位中のRは同じであり、殊に好ましくはR=−CH2−であるかまたは−(CH2)2−および−CH(CH3)−から選択されるかまたは−CH2−、−(CH2)2−および−CH(CH3)−から選択され;
iは、2〜4の整数であり;
nは、自然数(0を含む)であり、ここで、化合物(B)毎の2、3または4個のnは、同じかまたは異なっていてよく、かつ該化合物(B)中の2、3または4個のnの合計は、全ての分子(B)の平均で、2より大きく、かつ最大45であり;
R1、R2は、同じかまたは異なるアルキル基であり、好ましくはC1〜C10アルキル基、より好ましくはC4〜C6アルキル基、最も好ましくはsec−ブチル基、tert−ブチル基またはtert−アミル基、および殊にtert−ブチル基であり、ここで、化合物(B)毎の2、3または4個のR1およびR2は、同じかまたは異なっていてよく、
かつ
Xは、脂肪族の二官能性、三官能性または四官能性の脂肪族の線状または分岐状の基である。
Rは、線状または分岐状であり、かつ繰返し単位[−CH2−R−O−]から繰返し単位[−CH2−R−O−]まで異なっていてよい、任意に置換されたC1〜C5−アルキル基であり、好ましくはR=−CH2−、−(CH2)2−、−CH(CH3)−、および−(CH2)3−から選択され(後者はポリ−THF、殊に約250、650、1000、1800または2000g/molのモル質量のものに由来している)、より好ましくは各繰返し単位中のRは同じであり、殊に好ましくはR=−CH2−であるかまたは−(CH2)2−および−CH(CH3)−から選択されるかまたは−CH2−、−(CH2)2−または−CH(CH3)−から選択され;
nは、自然数であり、ここで、該化合物(B)中の(n+1)は、全ての分子(B)の平均で、3より大きく、かつ最大46であり;
かつ
R11、R21、R12およびR22は、同じかまたは異なるアルキル基、好ましくはC1〜C10アルキル基、より好ましくはC4−C6アルキル基、最も好ましくはsec−ブチル基、tert−ブチル基またはtert−アミル基、および殊にtert−ブチル基である。
− モノ−/ジ(エチルヘキシル)ホスフェート
− モノ−/ジブチルホスフェート
− モノ−/ジエチルホスフェート
である。
− King Industries社のNacure(登録商標) 4000(前のNacure(登録商標) C 207)、詳細に定義されないアルキルリン酸エステル
− King Industries社のNacure(登録商標) 4054、詳細に定義されないアルキルリン酸エステル
− Cytec社のCycat(登録商標) 296-9、詳細に定義されないアルキルリン酸エステル
− ベンゼンスルホン酸
− パラ−トルエンスルホン酸
− パラ−エチルベンゼンスルホン酸
− パラ−ドデシルベンゼンスルホン酸
− ビスノニルナフタレンスルホン酸
− ビスノニルナフタレンビススルホン酸
− ビスドデシルナフタレンスルホン酸
− Nacure(登録商標) XC-C210(King Industries社の明記されない構造の疎水性酸触媒)
(A)20〜99質量%、好ましくは20〜95質量%、特に好ましくは30〜90質量%、極めて特に好ましくは40〜80質量%、
(B)立体障害フェノール100〜10000質量ppm、好ましくは200〜5000質量ppm、特に好ましくは250〜3000質量ppm、極めて特に好ましくは300〜1500質量ppm、
(C)ルイス酸1〜10000質量ppm、好ましくは20〜2000質量ppmおよび特に好ましくは50〜500質量ppm、
(D)溶剤1〜80質量%、好ましくは溶剤5〜80質量%、特に好ましくは10〜70質量%、極めて特に好ましくは20〜60質量%、
(E)さらなる酸化防止剤0〜2000ppm、好ましくは10〜600ppm、特に好ましくは50〜300ppm、
(F)ブレンステッド酸0〜1000質量ppm、好ましくは2〜300質量ppm、特に好ましくは10〜100質量ppm、
(G)添加剤0〜5質量%、
ただし、該成分(B)、(C)、(E)、(F)、および(G)の質量ppmの記載はポリイソシアネート(A)に対するものであり、かつ該成分(A)および(D)の合計は、常に100質量%である、
(H)任意に、前記の成分(A)〜(G)に加えて、さらに顔料。
シュウ酸、マレイン酸、フマル酸、コハク酸、グルタル酸、アジピン酸、セバシン酸、ドデカン二酸、o−フタル酸、イソフタル酸、テレフタル酸、トリメリト酸、アゼライン酸、1,4−シクロヘキサンジカルボン酸またはテトラヒドロフタル酸、スベリン酸、アゼライン酸、無水フタル酸、テトラヒドロフタル酸無水物、ヘキサヒドロフタル酸無水物、テトラクロロフタル酸無水物、エンドメチレンテトラヒドロフタル酸無水物、グルタル酸無水物、無水マレイン酸、ダイマー脂肪酸、それらの異性体および水素化生成物ならびに挙げられた酸のエステル化できる誘導体、例えば無水物またはジアルキルエステル、例えばC1〜C4−アルキルエステル、好ましくはメチル、エチルまたはn−ブチルエステルが使用される。好ましいのは、一般式HOOC−(CH2)y−COOHのジカルボン酸であり、ここで、yは、1〜20の数、好ましくは2〜20の偶数であり、特に好ましいのは、ヘキサヒドロフタル酸無水物、コハク酸、アジピン酸、セバシン酸およびドデカンジカルボン酸である。
ppmの量の記載は、一般に質量ppmである。
ポリイソシアネートA:ヘキサメチレンジイソシアネートをベースとするイソシアヌレート:ヘキサメチレンジイソシアネートHDIを、触媒として、ヘキサメチレンジイソシアネートに対して60ppmの、エチルヘキサノール中5%濃度のベンジルトリメチルアンモニウムヒドロキシイソブチレートの存在下で、各40minの平均スループット時間を有する3つの反応器からなるカスケードにおいて120℃で変換した。該反応を、スタティックミキサー中で、該触媒に対して化学量論的、22%の、ヘキサメチレンジイソシアネート中に溶解した10%濃度のジ−(2−エチルヘキシル)ホスフェートで停止させた。ヘキサメチレンジイソシアネートを、複数の蒸留段階によって留去した。生成物のNCO含有率:22.2%、色数 19Hz(ハーゼン単位);粘度:2630mPa・s。
本発明による:
フェノールB1:978g/molの数平均分子量Mnおよび−2℃の融点を有するポリエチレングリコール−ビス[3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオネート]:
ポリエチレングリコール500g(Mw=201.8g/mol、2.5mol)を、3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオン酸メチルエステル1310g(292.4g/mol;5mol)ならびにジブチルスズジラウレート500ppmと共に、300mlフラスコ中に添加した。これを170℃に加熱した。該溶液に、慎重に窒素を導入した。生じたメタノールを、リービッヒ冷却器中で凝縮させた。18h後に、該反応が終了した。GPCによる分析は、その出発成分の完全な転化を確認する。
インジェクター:オートサンプラーWATERS 717 Plus
溶離液:テトラヒドロフラン(流量:1ml/min)
ポンプ:WATERS Modell 515(ダブルプランジャーポンプ)
検出器1:UV検出器WATERS 2489(波長:254nm)
検出器2:示差屈折計WATERS 2414(測定温度:35℃)
カラムセット:PLゲルカラム(300×7.5mm)、4本のカラムを直列に接続:カラム材料:架橋ポリスチレン−ジビニルベンゼンマトリックス、粒度5μm:孔径:2×500Å;1×1000Å、1×10000Å
校正:ポリスチレン標準、モル質量範囲450000〜312g/mol
ソフトウェア:PSS WinGPC Unity NT
フェノールB2:C7〜C9−分岐状アルキルエステル−3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオネート(BASF SEのIrganox(登録商標) 1135)
フェノールB3:2,6−ジ−tert−ブチル−4−メチルフェノール(BHT)
フェノールB4:ペンタエリトリトール−テトラキス[3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオネート](BASF SEのIrganox(登録商標) 1010)、分岐状テトラフェノール
D1:ソルベントナフサ(Solvesso(登録商標) 100、沸点範囲 約170〜180℃)
D2:メチルエチルケトン
酸化防止剤E:
E1:ジオクチルホスホネート(BASF SEのIrgafos(登録商標) OPH)
E2:トリフェニルホスフィット(Tppt、Aldrich)
これらは、製造における通常のプロセス時間内に、純ポリイソシアネート(A)に良溶であるべきである。フェノール(B)のポリイソシアネート(A)への溶解度は、市販のポリイソシアヌレートBasonat(登録商標) HI 100中の1および10%のフェノール(B)を用いて、試料をローラー上で35回転/minの速度で室温で回転させることによって決定した。良好な配合性のためには、該フェノール(B)が、工業的な配合の際に技術的課題を引き起こさないためには、少なくとも10%中に室温で30分以内に溶解しなければならないことが確かめられた。
Claims (16)
- ポリイソシアネート組成物であって、
−(A)少なくとも1種のモノメリックイソシアネートの反応により得られる、少なくとも1種の(環式)脂肪族ポリイソシアネート、
−(B)40℃未満の融点および650〜2550g/molの数平均分子量Mnを有し、少なくとも2個のフェノール性基を有する、少なくとも1種の立体障害フェノール、
−(C)イソシアネート基と、イソシアネートに対して反応性の基との反応を促進することができる、少なくとも1種のルイス酸性有機金属化合物、
−(D)少なくとも1種の溶剤、
−(E)任意に、少なくとも1種のさらなる酸化防止剤、
−(F)任意に、4未満のpKa値を有する、少なくとも1種のブレンステッド酸、
−(G)任意に、その他の塗料添加剤
を含有する、前記ポリイソシアネート組成物。 - 前記モノメリックイソシアネートが、1,6−ヘキサメチレンジイソシアネート、1,5−ペンタメチレンジイソシアネート、イソホロンジイソシアネート、1,3−ビス(イソシアナトメチル)シクロヘキサン、4,4′−ジ(イソシアナトシクロヘキシル)メタンおよび2,4′−ジ(イソシアナトシクロヘキシル)メタンからなる群から選択されるジイソシアネート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。
- 前記ポリイソシアネート(A)が、イソシアヌレート基、ビウレット基、アロファネート基、ウレタン基、ウレトジオン基および/またはイミノオキサジアジンジオン基を有することを特徴とする、請求項1または2に記載のポリイソシアネート組成物。
- 前記ポリイソシアネート(A)が、5〜25質量%の範囲内のNCO含有率を有することを特徴とする、請求項1から3までのいずれか1項に記載のポリイソシアネート組成物。
- 前記ポリイソシアネート(A)が、アンモニウムカルボキシレート、アンモニウムヒドロキシカルボキシレートまたは水酸化アンモニウム触媒を使用して製造された、イソシアヌレート基、および/またはアロファネート/ウレタン基を有することを特徴とする、請求項1から4までのいずれか1項に記載のポリイソシアネート組成物。
- 前記ポリイソシアネートが、500〜4000mPa・sの粘度を有する主としてイソシアヌレート基を有するポリイソシアネート、および/または150〜1600mPa・sの粘度を有する任意にイソシアヌレートおよび/またはウレタンを有する低粘度アロファネートおよび/または300〜1200mPa・sの粘度を有する任意にイソシアヌレートを有するイミノオキサジアジンジオンであることを特徴とする、請求項1から5までのいずれか1項に記載のポリイソシアネート組成物。
- 化合物(B)が、芳香環あたり正確に1個のフェノール性ヒドロキシ基を有し、かつ前記フェノール性ヒドロキシ基に対して両方のオルト位でアルキル基で、好ましくはC1〜C10アルキルで、より好ましくはC4〜C6アルキルで、よりいっそう好ましくはsec−ブチル、tert−ブチルまたはtert−アミルで、および殊に両方のオルト位でtert−ブチルで、置換されていることを特徴とする、請求項1から6までのいずれか1項に記載のポリイソシアネート組成物。
- 化合物(B)が、ポリアルキレンオキシド−ビス−/トリまたは−/テトラ−[3−(3,5−ジアルキル−4−ヒドロキシフェニル)プロピオネート]の次の構造を有し、
Rは、線状または分岐状であり、かつ繰返し単位[−CH2−R−O−]から繰返し単位[−CH2−R−O−]まで異なっていてよい、任意に置換されたC1〜C5−アルキル基であり、好ましくはR=−CH2−、−(CH2)2−、−CH(CH3)−および−(CH2)3−から選択され、より好ましくは各繰返し単位中のRは同じであり、殊に好ましくはR=−CH2−であるかまたは−(CH2)2−および−CH(CH3)−から選択されるかまたは−CH2−、−(CH2)2−および−CH(CH3)−から選択され;
iは、2〜4の整数であり;
nは、自然数(0を含む)であり、ここで、化合物(B)毎の2、3または4個のnは、同じかまたは異なっていてよく、かつ前記化合物(B)中の2、3または4個のnの合計は、全ての分子(B)の平均で、2より大きく、かつ最大45であり;
R1、R2は、同じかまたは異なるアルキル基、好ましくはC1〜C10アルキル基、より好ましくはC4〜C6アルキル基、最も好ましくはsec−ブチル基、tert−ブチル基またはtert−アミル基、および殊にtert−ブチル基であり、ここで、化合物(B)毎の2、3または4個のR1およびR2は、同じかまたは異なっていてよく、
かつ
Xは、脂肪族の二官能性、三官能性または四官能性の脂肪族の線状または分岐状の基である
ことを特徴とする、請求項1から7までのいずれか1項に記載のポリイソシアネート組成物。 - 化合物(B)が、ポリアルキレンオキシド−ビス−[3−(3,5−アルキル−4−ヒドロキシフェニル)プロピオネート]の次の構造を有し、
Rは、線状または分岐状であり、かつ繰返し単位[−CH2−R−O−]から繰返し単位[−CH2−R−O−]まで異なっていてよい、任意に置換されたC1〜C5−アルキル基であり、好ましくはR=−CH2−、−(CH2)2−、−CH(CH3)−、および−(CH2)3−から選択され(後者は、殊に約250、650、1000、1800または2000g/molのモル質量の、ポリ−THFに由来している)、より好ましくは各繰返し単位中のRは同じであり、殊に好ましくはR=−CH2−であるかまたは−(CH2)2−および−CH(CH3)−から選択されるかまたは−CH2−、−(CH2)2−または−CH(CH3)−から選択され;
nは、自然数であり、ここで、前記化合物(B)中の(n+1)は、全ての分子(B)の平均で、3より大きく、かつ最大46であり;
かつ
R11、R21、R12およびR22は、同じかまたは異なるアルキル基、好ましくはC1〜C10アルキル基、より好ましくはC4〜C6アルキル基、最も好ましくはsec−ブチル基、tert−ブチル基またはtert−アミル基、および殊にtert−ブチル基である
ことを特徴とする、請求項1から8までのいずれか1項に記載のポリイソシアネート組成物。 - 前記ルイス酸性有機金属化合物(C)が、スズ、亜鉛、チタン、ジルコニウム、およびビスマスからなる群から選択される金属を含有するか、またはそのような化合物の混合物を含有することを特徴とする、請求項1から9までのいずれか1項に記載のポリイソシアネート組成物。
- 前記溶剤(D)が、芳香族炭化水素、(環式)脂肪族炭化水素、ケトン、エステル、エーテル、エーテルエステルおよびカーボネートから、殊に、主にC9およびC10−芳香族化合物を有する芳香族炭化水素の蒸留留分から、およびジアルキルケトンから、またはそれらの混合物からなる群から選択されていることを特徴とする、請求項1から10までのいずれか1項に記載のポリイソシアネート組成物。
- 前記酸化防止剤(E)が、ホスフィット、ホスホニット、ホスホネートおよびチオエーテルの群から選択されていることを特徴とする、請求項1から11までのいずれか1項に記載のポリイソシアネート組成物。
- 少なくとも1種のポリイソシアネート(A)を含有するポリイソシアネート組成物を安定化させる方法であって、前記ポリイソシアネート組成物に、さらに、40℃未満の融点および650〜2550g/molの数平均分子量を有し、少なくとも2個のフェノール性基を有する少なくとも1種の立体障害フェノール(B)、ならびにイソシアネート基と、イソシアネートに対して反応性の基との反応を促進することができる少なくとも1種のルイス酸性有機金属化合物(C)、少なくとも1種の溶剤(D)、任意に少なくとも1種のさらなる酸化防止剤(E)、任意に4未満のpKa値を有する少なくとも1種のブレンステッド酸(F)、および任意にその他の塗料添加剤(G)を混合する
ことを特徴とする、前記方法。 - ポリウレタン塗料を製造する方法であって、請求項1から12までのいずれか1項に記載のポリイソシアネート組成物を、イソシアネートに対して反応性の基を有する少なくとも1種のバインダーと反応させることを特徴とする、前記方法。
- ポリウレタン塗料を製造する方法であって、請求項1から12までのいずれか1項に記載のポリイソシアネート組成物を、ポリアクリレートポリオール、ポリエステルポリオール、ポリエーテルポリオール、ポリウレタンポリオール、ポリ尿素ポリオール、ポリエーテルオール、ポリカーボネート、ポリエステルポリアクリレートポリオール、ポリエステルポリウレタンポリオール、ポリウレタンポリアクリレートポリオール、ポリウレタン変性アルキド樹脂、脂肪酸変性ポリエステルポリウレタンポリオール、アリルエーテルを有するコポリマーおよび挙げた物質群のコポリマーもしくはグラフトポリマー、好ましくはポリアクリレートポリオールおよび/またはポリエステルポリオールからなる群から選択される、少なくとも1種のバインダーと反応させることを特徴とする、前記方法。
- 補修塗装、自動車補修塗装、自動車塗装、大型車両塗装および木材塗装の分野のプライマー、プライマーサーフェーサー、顔料添加されたトップコート、ベースコートおよびクリアコートにおけるコーティング組成物中の硬化剤として、ならびに塗料、接着剤およびシーラントにおける硬化剤としての、請求項1から12までのいずれか1項に記載のポリイソシアネート組成物の使用。
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CN114316210A (zh) * | 2022-01-05 | 2022-04-12 | 万华化学(宁波)有限公司 | 一种缩二脲多异氰酸酯组合物及其制备方法 |
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