JP5930345B2 - マイケル付加によって製造できるアミン付加物 - Google Patents
マイケル付加によって製造できるアミン付加物 Download PDFInfo
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- JP5930345B2 JP5930345B2 JP2014541562A JP2014541562A JP5930345B2 JP 5930345 B2 JP5930345 B2 JP 5930345B2 JP 2014541562 A JP2014541562 A JP 2014541562A JP 2014541562 A JP2014541562 A JP 2014541562A JP 5930345 B2 JP5930345 B2 JP 5930345B2
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- 239000000347 magnesium hydroxide Substances 0.000 description 1
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- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
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- KMBPCQSCMCEPMU-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)CCCN KMBPCQSCMCEPMU-UHFFFAOYSA-N 0.000 description 1
- AQGNVWRYTKPRMR-UHFFFAOYSA-N n'-[2-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCNCCN AQGNVWRYTKPRMR-UHFFFAOYSA-N 0.000 description 1
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- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
- SCHTXWZFMCQMBH-UHFFFAOYSA-N pentane-1,3,5-triamine Chemical compound NCCC(N)CCN SCHTXWZFMCQMBH-UHFFFAOYSA-N 0.000 description 1
- 239000010451 perlite Substances 0.000 description 1
- 235000019362 perlite Nutrition 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
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- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
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- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
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- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
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- 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 1
- YPMOSINXXHVZIL-UHFFFAOYSA-N sulfanylideneantimony Chemical compound [Sb]=S YPMOSINXXHVZIL-UHFFFAOYSA-N 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
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- 239000003784 tall oil Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical group CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- 238000004627 transmission electron microscopy Methods 0.000 description 1
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- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical group OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- YFHICDDUDORKJB-UHFFFAOYSA-N trimethylene carbonate Chemical compound O=C1OCCCO1 YFHICDDUDORKJB-UHFFFAOYSA-N 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical compound [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/45—Anti-settling agents
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
- C08G63/6854—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen derived from polycarboxylic acids and polyhydroxy compounds
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/91—Polymers modified by chemical after-treatment
- C08G63/912—Polymers modified by chemical after-treatment derived from hydroxycarboxylic 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/91—Polymers modified by chemical after-treatment
- C08G63/914—Polymers modified by chemical after-treatment derived from polycarboxylic acids and polyhydroxy compounds
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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
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
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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
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
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- 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
- C09D17/00—Pigment pastes, e.g. for mixing in paints
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J167/00—Adhesives based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Adhesives based on derivatives of such polymers
- C09J167/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/28—Non-macromolecular organic substances
- C08L2666/34—Oxygen-containing compounds, including ammonium and metal salts
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/28—Non-macromolecular organic substances
- C08L2666/36—Nitrogen-containing compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Paints Or Removers (AREA)
- Polyesters Or Polycarbonates (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Description
(A):(B)=1:1000〜1:1、および
(A):(C)=1:100〜100:1
の質量比で反応させるアミン付加物の製造方法であって、前記反応は、
反応変法i)によれば、まずポリアミン成分(A)とポリエステル成分(B)から反応中間生成物(A−B)を生成し、それを引き続き炭化水素成分(C)と反応させるか、または
反応変法ii)によれば、まずポリアミン成分(A)と炭化水素成分(C)から反応中間生成物(A−C)を形成させ、それを次いでポリエステル成分(B)と反応させるか、または
反応変法iii)によれば、まずポリアミン成分(A)をポリエステル成分(B)および炭化水素成分(C)と同時に反応させるか、
のいずれかで実施し、その際、
前記ポリエステル成分(B)および炭化水素成分(C)は、前記反応の反応条件で互いに反応せず、
前記ポリアミン成分(A)は、有機ポリアミン化合物(A’)の形で存在し、
前記有機ポリアミン化合物(A’)は、第一級および第二級アミノ基から選択される、それぞれポリエステル成分(B)および炭化水素成分(C)と反応可能なそれぞれ少なくとも3つのアミノ基(A’+)を有し、
前記ポリエステル成分(B)は、ポリエステル化合物(B’)の形で存在し、
前記ポリエステル化合物(B’)は、それぞれ第一級アミノ基を有さずかつそれぞれ第二級アミノ基を有さず、それぞれ少なくとも3つのエステル基を有し、かつカルボキシル基もしくは無水カルボン酸基として存在する、第一級および/または第二級アミノ基と反応可能なそれぞれ1つのカップリング基(B’+)を有し、かつ
前記炭化水素成分(C)は、それぞれ1つの結合基(C’+)を有する分枝鎖状もしくは非分枝鎖状の飽和もしくは不飽和の炭化水素化合物(C’)の形で存在し、
前記炭化水素化合物(C’)は、それぞれ第一級アミノ基を有さず、それぞれ第二級アミノ基を有さず、それぞれカルボキシル基を有さず、かつそれぞれ無水カルボン酸基を有さず、かつそれぞれ炭素原子の、元素O、N、P、S、Siの群から選択されるヘテロ原子に対する全体比が少なくとも2:1であり、その際、前記結合基(C’+)は、それぞれ、第一級アミノ基と反応して第二級アミノ基を生成する特性および/または第二級アミノ基と反応して第三級アミノ基を形成する特性を有し、かつ前記結合基(C’+)は、それぞれ更に一般式(I)
R4R5C=CR6R7 (I)
[式中、R4、R5、R6およびR7は、それぞれ互いに独立して、電子吸引性置換基E、Hおよび/または飽和もしくは不飽和の分枝鎖状もしくは非分枝鎖状のC1〜C12−炭化水素基によって表されるが、但し、基R4、R5、R6、R7からの全体で2つの基は、それぞれ閉環によって互いに結合されていてよく、基R4、R5、R6、R7からの少なくとも1つの基は、電子吸引性置換基Eとして存在し、かつ基R4、R5、R6、R7からの1つの基は、二価の単位であり、前記単位を介して、前記結合基(C’+)と炭化水素化合物(C’)の他の部分とが結合されている]の活性化されたアルケニル官能基の形で存在する、アミン付加物の製造方法である。
(A):(B)=1:100〜1:4、好ましくは(A):(B)=1:25〜1:7の質量比、および
(A):(C)=1:10〜10:1、好ましくは(A):(C)=1:2〜2:1の質量比
で実施される。
ポリアミン成分(A)の好適なポリアミン化合物(A’)のための例は、脂肪族の直鎖状ポリアミン、例えばジエチレントリアミン(DETA)、トリエチレンテトラミン(TETA)、テトラエチレンペンタミン(TEPA)、ペンタエチレンヘキサミン、ヘキサエチレンヘプタミンおよびより高級の同族体、一般式NH2−(C2H4NH)n−C2H4−NH2(n>5)のより高級の直鎖状縮合物、ジプロピレントリアミン、3−(2−アミノエチル)アミノプロピルアミン、N,N−ビス(3−アミノプロピル)メチルアミン、テトラメチルイミノビスプロピルアミン、N,N−ジメチルジプロピレントリアミン、ビス(3−ジメチルアミノプロピル)アミンおよびN,N’−ビス(3−アミノプロピル)エチレンジアミンである。
前記ポリエステル成分(B)のポリエステル化合物(B’)としては、例えば、ジカルボン酸ならびにそれらのエステル化可能な誘導体、例えば無水物、酸塩化物またはジアルキルエステル、例えばジメチルエステルまたはジエチルエステルの反応によって、ジオールおよび一官能性のカルボン酸との反応によって製造される化合物が好適である。ジヒドロキシポリエステルの形成は、必要に応じて、相応の化学量論量の一官能性カルボン酸を使用することによって抑制できる。前記エステル化は、そのままでまたは共沸剤の存在下での共沸エステル化によって実施することができる。かかる縮合反応は、例えば約50℃〜250℃の温度で実施される。相応して使用可能なジカルボン酸のための例は、コハク酸、マレイン酸、フマル酸、グルタル酸、アジピン酸、セバシン酸、ピメリン酸、フタル酸または二量化脂肪酸およびそれらの異性体ならびにそれらの水素化生成物である。相応して使用できるジオールのための例は、エチレングリコール、1,2−プロパンジオール、1,3−プロパンジオール、1,4−ブタンジオール、1,6−ヘキサンジオール、ネオペンチルグリコール、シス−1,2−シクロヘキサンジメタノール、トランス−1,2−シクロヘキサンジメタノールならびにエチレングリコールおよび/またはプロピレングリコールをベースとするポリグリコールである。相応して出発成分として使用されるモノカルボン酸は、好ましくは1〜42個の、特に4〜18個の、好ましくは8〜14個の炭素原子を有し、かつ前記カルボン酸は、飽和もしくは不飽和であってよく、脂肪族または芳香族であってよく、直鎖状、分枝鎖状および/または環状であってよい。相応して好適なモノカルボン酸のための例は、ステアリン酸、イソステアリン酸、オレイン酸、ラウリン酸および安息香酸である。更なる好適な酸は、コッホ酸とも呼ばれる第三級の飽和モノカルボン酸、例えば2,2−ジメチルプロパン酸、2,2−ジメチルブタン酸、2,2−ジメチルペンタン酸、t−ノナン酸ならびにネオデカン酸である。市販品として、かかるコッホ酸は、例えばVersatic(登録商標)酸(Shell)、Neo酸(Neosaeure)(Exxon)またはCeKanoic酸(Kuhlmann)の名称でも知られている。前記Versatic(登録商標)酸は、その分子が有している炭素原子の総数に応じて命名されている。好適な例は、Versatic(登録商標)酸5、6、9、10、913、1019である。
好ましくは、前記炭化水素成分(C)の炭化水素化合物(C’)は、それぞれ正確に1つの結合基(C’+)を有し、かつ好ましくはポリアミン成分(A)との反応に際して反応する更なる官能基を有さない。
−O−CO−CH=CR8R9 (Ia)
[式中、R8およびR9は、それぞれ同一または異なっており、かつそれぞれ互いに独立して、Hおよび/または飽和の、分枝鎖状もしくは非分枝鎖状のC1〜C12−炭化水素基によって表される]に従って存在する。
a)ラクトンからのポリエステル成分の一般的製造法:
撹拌機、温度計、還流冷却器および窒素導入管を備えた四ツ口フラスコにおいて、物質R1a)〜R1c)を装入し、N2ガス下で撹拌しながら100℃に加熱する。次いで、触媒を添加し、更にN2ガス下でT1へと加熱する。この温度で、FKが99%以上に達するまで撹拌する。
撹拌機、温度計、還流冷却器および窒素導入管を備えた四ツ口フラスコにおいて、物質R1a)〜R1c)を、N2ガス下で撹拌しながら100℃に加熱する。100℃で触媒を添加し、水分離器を被せる。それを更に加熱し、遊離した水を水分離器によって分離する。反応温度を、遊離した水に合わせ、T1までにする。反応水がもはや遊離しなくなったら、反応は完了している。
撹拌機、温度計、還流冷却器、水分離器および窒素導入管を備えた四ツ口フラスコにおいて、物質R1a)〜R1c)を触媒と一緒に量り入れ、N2ガス下で加熱する。生成された反応水を水分離器を介して捕集する。反応温度を、遊離した水に合わせ、T1までにする。反応水がもはや遊離しなくなったら、反応は完了している。
水の脱離下でのポリエステルとアミンとの反応:
撹拌機、温度計、還流冷却器、水分離器および窒素導入管を備えた四ツ口フラスコにおいて、物質R2aおよびR2b)を装入し、N2ガス下で加熱する。遊離した反応水を水分離器を介して捕集する。反応温度を、遊離した水に合わせ、T1までにする。反応水がもはや遊離しなくなったら、反応は完了している。
アミンと炭化水素成分との反応
撹拌機、温度計、還流冷却器および窒素導入管を備えた四ツ口フラスコにおいて、反応成分R2a)を装入し、N2ガス下で反応温度T1にまで加熱する。反応成分R2b)を予め定められた時間X1で計量供給する。後反応は、T1で1時間である。
撹拌機、温度計、還流冷却器および窒素導入管を備えた四ツ口フラスコにおいて、反応成分3a)を装入し、N2ガス下で100℃にまで加熱する。次いで、反応成分3b)を添加する。T1で時間X1にわたり撹拌する。次いで、反応成分3c)を添加し、そしてN2ガス下でT2に加熱する。後反応は、T2で時間X2にわたる。原料3d)との更なる反応の場合には、該原料は3c)の1時間後に添加され、相応の後反応時間を伴う。
撹拌機、温度計、還流冷却器および窒素導入管を備えた四ツ口フラスコにおいて、反応成分3a)を装入し、N2ガス下で100℃にまで加熱する。100℃で、反応成分3b)を添加し、次いでT1に加熱し、時間X1にわたり撹拌する。
撹拌機、温度計、還流冷却器および窒素導入管を備えた四ツ口フラスコにおいて、反応成分3a)を装入し、T1にまで加熱する。成分3b)をX1で計量供給する。計量供給後に、T1で0.5時間の後反応を行う。引き続き、反応成分3c)を添加し、そしてN2ガス下でT2に加熱する。引き続き、T2で後反応時間X2を行う。
撹拌機、温度計、還流冷却器および窒素導入管を備えた四ツ口フラスコにおいて、反応成分3a)を装入し、T1にまで加熱する。成分3b)を時間X1で添加する。引き続きN2ガス下でT2にまで加熱する。後反応時間は、次いでT2でX2である。
撹拌機、温度計、還流冷却器および窒素導入管を備えた四ツ口フラスコにおいて、反応成分3a)を装入し、N2ガス下でT1にまで加熱する。引き続き、反応成分3b)および3c)を、それぞれ別々にZ1で添加する。次いで、T2に加熱し、時間X2にわたり該混合物をT2で後反応のために撹拌する。
撹拌機、温度計、還流冷却器および窒素導入管を備えた四ツ口フラスコにおいて、反応成分3a)およびb)を装入し、N2ガス下でT1にまで加熱する。反応成分3c)をX1で計量供給する。引き続きT1で0.5時間の後反応を行う。引き続き、反応成分3d)を添加し、N2ガス下で更にT2にまで加熱する。引き続き、N2ガス下でT2で後反応をX2にわたり行う。
撹拌機、温度計、還流冷却器および導入管を備えた四ツ口フラスコにおいて、5.5部のヒドロキシエチルアクリレートを、66.00部のカプロラクトンおよび28.3部のバレロラクトンと一緒に0.01%のモノブチルスズオキシドおよび0.1%のヒドロキノンを用いて空気雰囲気下で撹拌しながら120℃に加熱することで、Mn2100を有するポリエステルが得られる。120℃で12時間後に、65℃に冷却する。次いで、6.91部のポリエチレンイミン(分子量2000)を添加する。反応物を次いで65℃で2時間にわたり撹拌する。
撹拌機、温度計、還流冷却器および導入管を備えた四ツ口フラスコにおいて、94.3部のポリエステルB10を装入し、100℃に加熱し、そして分子量2000を有するポリエチレンイミンを5.7部添加する。次いで、140℃に加熱し、この温度で2時間にわたり撹拌する。
本発明により関連するアミン付加物(ポリマー)は、とりわけ顔料濃縮物、塗料系およびインクジェット系の製造のための湿潤剤および分散剤として使用される。
作業装置:
シェイカー:LAU-Paint Shaker DAS H[/A]200-K
光沢/ヘイズ測定:
・ Trigloss(Byk Gardner)
・ 測定角20°
応用技術的試験のための物質:
Vinnol溶液: 75%ブチルグリコールアセテート+20%シクロヘキサノン+5%Vinnol 15/45
Vinnol 15/45: 約85質量%の塩化ビニルおよび約15質量%の酢酸ビニルからなるコポリマー(製造元Wacker)
Novoperm P-M3R: P.Y.139
Ink Jet Magenta E02: P.R.122、タイプA
Irgalite Blue: P.B.15:4、タイプB
NiPex 90: p.Bk-7、pH=9.0
・ 顔料濃縮物の製造のために、100mlのガラス瓶中に項目1〜4を量り入れて、混合する。引き続き100gのジルコニウムビーズ(0.4〜0.6mm)を加える
・ 予備混合された顔料濃縮物を、前記シェイカー中で冷却レベル3で960分にわたり分散させる
・ 顔料濃縮物を50mlのガラス瓶中でこす
・ 一晩貯蔵した後と、40℃で1週間にわたり貯蔵した後に、粘度をStress Tech Instrumentによって測定する
・ 該濃縮物を、PUシート上に25μmの湿式被膜厚で塗布する
・ 色強度および透明性の評価は、そのシート上で視覚的に行い、光沢とヘイズの測定については、前記シートを黒色の厚紙に載せて測定する
本発明により関連するポリマーの特に良好な品質は、低い粘度、色強度、透明性および良好な光沢に関して示している。該ポリマーの具体的な利点は、バインダー溶液における特に良好な混入性にもある。
作業装置:
Dispermat CV
Trigloss(Byk Gardner)
Scandexシェイカー
ランプブラックFW200→ PB 7
Laropoal A81→ アルデヒド樹脂(製造元BASF)
Paraloid DM 66→ 熱可塑性アクリレート樹脂(TPA)(製造元DOW)
Macrynal SM 510→ アクリレート樹脂70%(製造元Cytec)
Desmodur N75→ 脂肪族イソシアネート、メトキシプロピルアセテート中75%(製造元Bayer)
Setalux 1756 V V65→ アクリレート樹脂、ソルベントナフサ中65%(製造元Nuplex)
Setamine US 138 0→ メラミン樹脂、n−ブタノール中70%(製造元Nuplex)
Epikote 1001→ エポキシ樹脂、キシレン中75%(製造元Brenntag)
Aradur 115→ ポリアミドアミン(製造元Huntsman)
Dowanol PMA→ メトキシプロピルアセテート(製造元DOW)
Dowanol PM→ メトキシプロパノール(製造元DOW)
Solvesso 100→ 芳香族溶剤(Exxon)
BYK 306/310/325→ レベリング添加剤(製造元BYK)
顔料濃縮物の製造:
・ 塗料成分を示した順序で量り入れる(それぞれの添加直後に手で撹拌する)
・ Dispermat CV/60分/10000回転/分(23m/s)を40℃で
粉砕物/ガラスビーズ(0.8〜1.2mm)比は1:1(質量比)である
・ 分散後にガラスビーズを篩別する
・ 粘度を視覚的に評価する(製造の1日後)
塗料の製造:
・ 顔料濃縮物を5分にわたってScandexシェイカーで種々の塗料系に混入させる
・ 希釈された塗料をPEシート上に注ぐ
・ 透明性と光学に関して視覚的に全体評価する→ 1〜5(1は良い、5は悪い)
・ Triglossで光沢測定をする
塗料系における光学:1〜5(1は良い、5は悪い)
粘度: hvは高粘度で、mvは中粘度で、nvは低粘度である
12.5%のカーボンブラックを有し、かつ顔料に対してちょうど80%の添加剤を有する顔料ペースト
本発明によるアミン付加物は、種々の塗料系における特に良好な相容性の点で優れている。相応の顔料ペーストは、低粘度であり、かつ優れた混入性を有する。より高い顔料含有率を有する顔料ペーストの製造が簡単にできる。顔料濃縮物の優れた良好な光沢および優れた貯蔵安定性が特に強調される。
Claims (10)
- ポリアミン成分(A)と、ポリエステル成分(B)と、炭化水素成分(C)とを、
(A):(B)=1:1000〜1:1、および
(A):(C)=1:100〜100:1
の質量比で反応させるアミン付加物の製造方法であって、前記反応は、
反応変法i)によれば、まずポリアミン成分(A)とポリエステル成分(B)から反応中間生成物(A−B)を生成し、それを引き続き炭化水素成分(C)と反応させるか、または
反応変法ii)によれば、まずポリアミン成分(A)と炭化水素成分(C)から反応中間生成物(A−C)を形成させ、それを次いでポリエステル成分(B)と反応させるか、または
反応変法iii)によれば、まずポリアミン成分(A)をポリエステル成分(B)および炭化水素成分(C)と同時に反応させるか、
のいずれかで実施し、その際、
前記ポリエステル成分(B)および炭化水素成分(C)は、前記反応の反応条件で互いに反応せず、
前記ポリアミン成分(A)は、有機ポリアミン化合物(A’)の形で存在し、
前記有機ポリアミン化合物(A’)は、第一級および第二級アミノ基から選択される、それぞれポリエステル成分(B)および炭化水素成分(C)と反応可能なそれぞれ少なくとも3つのアミノ基(A’+)を有し、
前記ポリエステル成分(B)は、ポリエステル化合物(B’)の形で存在し、
前記ポリエステル化合物(B’)は、それぞれ第一級アミノ基を有さずかつそれぞれ第二級アミノ基を有さず、それぞれ少なくとも3つのエステル基を有し、かつカルボキシル基もしくは無水カルボン酸基として存在する、第一級および/または第二級アミノ基と反応可能なそれぞれ1つのカップリング基(B’+)を有し、かつ
前記炭化水素成分(C)は、それぞれ1つの結合基(C’+)を有する分枝鎖状もしくは非分枝鎖状の飽和もしくは不飽和の炭化水素化合物(C’)の形で存在し、
前記炭化水素化合物(C’)は、それぞれ第一級アミノ基を有さず、それぞれ第二級アミノ基を有さず、それぞれカルボキシル基を有さず、かつそれぞれ無水カルボン酸基を有さず、かつそれぞれ炭素原子の、元素O、N、P、S、Siの群から選択されるヘテロ原子に対する全体比が少なくとも2:1であり、その際、前記結合基(C’+)は、それぞれ、第一級アミノ基と反応して第二級アミノ基を生成する特性および/または第二級アミノ基と反応して第三級アミノ基を形成する特性を有し、かつ前記結合基(C’+)は、それぞれ更に一般式(I)
R4R5C=CR6R7 (I)
[式中、R4、R5、R6およびR7は、それぞれ互いに独立して、電子吸引性置換基E、Hおよび/または飽和もしくは不飽和の分枝鎖状もしくは非分枝鎖状のC1〜C12−炭化水素基によって表されるが、但し、基R4、R5、R6、R7からの全体で2つの基は、それぞれ閉環によって互いに結合されていてよく、基R4、R5、R6、R7からの少なくとも1つの基は、電子吸引性置換基Eとして存在し、かつ基R4、R5、R6、R7からの1つの基は、二価の単位であり、前記単位を介して、前記結合基(C’+)と炭化水素化合物(C’)の他の部分とが結合されている]の活性化されたアルケニル官能基の形で存在する、アミン付加物の製造方法。 - 請求項1に記載の方法であって、(A)、(B)ならびに(C)の反応は、
(A):(B)=1:100〜1:4の質量比、および
(A):(C)=1:10〜10:1の質量比
で実施されることを特徴とする方法。 - 請求項1または2に記載の方法であって、使用されるポリエステル化合物(B’)の少なくとも50質量%は直鎖状のモノカルボキシ官能性のカプロラクトンポリエステルの形で存在することを特徴とする方法。
- 請求項1から3までのいずれか1項の方法であって、前記炭化水素成分(C)は、少なくとも30質量%の、それぞれ少なくとも1つのアリール基および/またはアルキルアリール基を有する不飽和のC6〜C50−炭化水素化合物(C’)を含有することを特徴とする方法。
- 請求項1から3までのいずれか1項の方法であって、前記炭化水素成分(C)は、少なくとも30質量%の、それぞれ少なくとも1つの分枝鎖状のアルキル基および/または分枝鎖状のアルケニル基を含むC10〜C70−炭化水素化合物(C’)を含有することを特徴とする方法。
- 請求項1から5までのいずれか1項の方法であって、成分(A)、(B)および(C)は、使用されるポリアミン化合物(A’)の反応可能なアミノ基(A’+)の全体の少なくとも50モル%が全体でポリエステル化合物(B’)および/または炭化水素化合物(C’)と反応するような化学量論比でそれぞれ使用されることを特徴とする方法。
- 請求項1から6までのいずれか1項の方法であって、前記アミン付加物は、室温で、それぞれ固体形で生じ、その際、(B)と(C)とは、2:1〜50:1の質量比で反応され、かつ前記アミン付加物は、30〜200℃の溶融範囲を有することを特徴とする方法。
- 請求項1から7までのいずれか1項の方法であって、反応変法iv)によれば、前記ポリアミン成分(A)、ポリエステル成分(B)および炭化水素成分(C)は、経時的に変動する量比で反応されるが、但し、前記反応の少なくとも第一の期間は、反応の変法i)〜iii)の1つに従って行われることを特徴とする方法。
- 請求項1から8までのいずれか1項の方法に従って製造できるアミン付加物を、添加剤として、コーティングにおいて用いるか、あるいは塗料、プラスチック、顔料ペースト、シーラント、化粧品、セラミック、接着剤、流延材料、平面ディスプレイ技術の顔料含有材料、フィラー材料、印刷インキまたはインキにおいて用いる使用。
- 請求項9に記載の使用であって、前記アミン付加物が、湿潤剤または分散剤であることを特徴とする使用。
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DE102014205680A1 (de) * | 2014-03-26 | 2015-10-01 | Evonik Degussa Gmbh | Dispergierharze |
WO2016053641A1 (en) | 2014-09-29 | 2016-04-07 | Blue Cube Ip Llc | Adduct composition |
CN105413507A (zh) * | 2015-12-08 | 2016-03-23 | 无锡万能胶粘剂有限公司 | 一种粘合剂配液乳化机 |
US10626314B1 (en) | 2016-07-11 | 2020-04-21 | Byk-Chemie, Gmbh | Additive for drilling fluids |
EP3512899B1 (de) | 2016-09-16 | 2021-11-10 | BYK-Chemie GmbH | Polyestermodifizierte aminoaddukte |
EP3428216B1 (en) | 2017-07-11 | 2022-11-02 | Henkel AG & Co. KGaA | Method for producing functionalized polyesters |
JP6986134B2 (ja) * | 2017-08-08 | 2021-12-22 | ベーイプシロンカー ヘミー ゲゼルシャフト ミット ベシュレンクター ハフトゥング | アミン官能性化合物 |
KR102227518B1 (ko) | 2018-08-14 | 2021-04-16 | (주)파밍봇 | 클라우드 데이터베이스 연동 일괄 인쇄 장치 및 그 방법 |
CN112867751B (zh) * | 2018-08-16 | 2023-10-27 | 巴斯夫欧洲公司 | 用于涂料体系的分散剂 |
CN109851800B (zh) * | 2018-12-27 | 2021-10-01 | 博邦新材料科技(广州)有限公司 | 一种基于松香衍生物的分散剂及其制备方法 |
EP3938422B1 (en) * | 2019-03-14 | 2024-05-01 | Lubrizol Advanced Materials, Inc. | Multi-amine polyester dispersant made via an anhydride intermediate |
WO2021257937A1 (en) * | 2020-06-18 | 2021-12-23 | Nanometics Llc (D.B.A. Phd Biosciences) | Chemically cross-linked elastomers formed by michael addition and compositions comprising such elastomers |
PL3943526T3 (pl) * | 2020-07-23 | 2024-05-20 | Evonik Operations Gmbh | Dyspergatory poliamidoaminowe |
TW202244137A (zh) * | 2021-02-18 | 2022-11-16 | 日商富士軟片股份有限公司 | 樹脂組成物、膜、濾光器、固體攝像元件、圖像顯示裝置、樹脂及樹脂之製造方法 |
WO2023180240A1 (en) | 2022-03-21 | 2023-09-28 | Byk-Chemie Gmbh | Dispersant composition for use in manufacturing batteries |
Family Cites Families (29)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US13807A (en) | 1855-11-13 | Steaw-cuttek | ||
JPS6312335A (ja) * | 1986-07-02 | 1988-01-19 | Dainippon Ink & Chem Inc | 分散剤ならびにそれを含有する分散液 |
CA1303783C (en) * | 1986-10-07 | 1992-06-16 | Robert Dean Lundberg | Lactone modified, aminated dispersant additives useful in oleaginous compositions |
US4963275A (en) | 1986-10-07 | 1990-10-16 | Exxon Chemical Patents Inc. | Dispersant additives derived from lactone modified amido-amine adducts |
DE3641581C3 (de) | 1986-12-05 | 1996-08-01 | Byk Chemie Gmbh | Verfahren zur Herstellung von Dispergiermitteln und deren Salzen und ihre Verwendung |
DE3643007A1 (de) | 1986-12-17 | 1988-06-30 | Basf Ag | Haertbare polyesterformmassen |
JPH0248029A (ja) * | 1988-08-05 | 1990-02-16 | Dainippon Ink & Chem Inc | 分散剤及び該分散剤を含有する分散液 |
JP2704211B2 (ja) | 1988-08-22 | 1998-01-26 | 大日本インキ化学工業株式会社 | 分散剤並びにそれを含有する分散液 |
JPH03103478A (ja) * | 1988-08-26 | 1991-04-30 | Nippon Oil & Fats Co Ltd | 顔料分散剤 |
EP0358358B1 (en) | 1988-08-26 | 1994-11-30 | Nippon Oil And Fats Company, Limited | Pigment dispersing agent |
US5187229A (en) | 1988-08-26 | 1993-02-16 | Nippon Oil And Fats Company, Ltd. | Pigment dispersing agent |
JPH02107327A (ja) | 1988-10-14 | 1990-04-19 | Dai Ichi Kogyo Seiyaku Co Ltd | 微粉末の非水系分散剤 |
JPH06312335A (ja) | 1993-04-26 | 1994-11-08 | Murata Mfg Co Ltd | ワーク挿入装置 |
JP3313897B2 (ja) | 1994-08-01 | 2002-08-12 | ダイセル化学工業株式会社 | 顔料分散剤 |
JPH08143851A (ja) | 1994-11-18 | 1996-06-04 | Hitachi Ltd | 不凍液の再生処理装置 |
JP3534859B2 (ja) | 1994-11-22 | 2004-06-07 | ダイセル化学工業株式会社 | 顔料分散剤、塗料組成物および印刷インキ組成物 |
US6194539B1 (en) | 1994-11-22 | 2001-02-27 | Daicel Chemical Industries, Inc. | Polylactone having amino groups, a process for the preparation thereof, a compound having amino group, a composition for coatings, a composition for printing inks |
JP3419927B2 (ja) * | 1994-11-22 | 2003-06-23 | ダイセル化学工業株式会社 | アミノ基含有ポリラクトン類およびその製造方法 |
JP3488001B2 (ja) * | 1995-12-08 | 2004-01-19 | ダイセル化学工業株式会社 | 顔料分散剤、塗料組成物及び印刷インキ組成物 |
DE19732251B4 (de) | 1997-07-26 | 2004-07-29 | Byk-Chemie Gmbh | Versalzungsprodukte von Polyaminen und deren Einsatz als Dispergiermittel für Pigmente und Füllstoffe |
GB9809025D0 (en) * | 1998-04-28 | 1998-06-24 | Zeneca Ltd | Amine dispersants |
JP2002088334A (ja) | 2000-09-11 | 2002-03-27 | Diabond Industry Co Ltd | 生分解性ホットメルト接着剤 |
DE10326147A1 (de) * | 2003-06-06 | 2005-03-03 | Byk-Chemie Gmbh | Epoxid-Addukte und deren Salze als Dispergiermittel |
DE102005004024A1 (de) | 2005-01-28 | 2006-08-03 | Goldschmidt Gmbh | Polyether/Polyester enthaltende Dispergierharze |
DE102006012999A1 (de) * | 2006-03-22 | 2007-09-27 | Byk-Chemie Gmbh | Additionsverbindungen als Dispergiermittel und Dispersionsstabilisatoren |
WO2007114152A1 (ja) | 2006-03-29 | 2007-10-11 | Sakata Inx Corp. | チタン酸バリウム分散組成物 |
JP5044759B2 (ja) | 2007-03-16 | 2012-10-10 | 名古屋市 | 蛍光性樹脂組成物及びその製造方法 |
JP5728816B2 (ja) | 2010-03-26 | 2015-06-03 | 東洋インキScホールディングス株式会社 | 無機酸化物分散用ビニル重合体、およびそれを含んでなる導電性無機酸化物分散体 |
KR101940359B1 (ko) | 2011-11-18 | 2019-04-10 | 비와이케이-케미 게엠베하 | 에폭시드 화합물을 기제로 하는 아민 부가생성물 |
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US20140296430A1 (en) | 2014-10-02 |
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ES2543112T3 (es) | 2015-08-14 |
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EP2780391B1 (de) | 2015-03-04 |
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