JP6862431B2 - 還流冷却下でポリアスパラギン酸を生成させるための方法 - Google Patents
還流冷却下でポリアスパラギン酸を生成させるための方法 Download PDFInfo
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- JP6862431B2 JP6862431B2 JP2018512188A JP2018512188A JP6862431B2 JP 6862431 B2 JP6862431 B2 JP 6862431B2 JP 2018512188 A JP2018512188 A JP 2018512188A JP 2018512188 A JP2018512188 A JP 2018512188A JP 6862431 B2 JP6862431 B2 JP 6862431B2
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- ZYFXHKPHYKLIDV-UHFFFAOYSA-N hydrogen peroxide;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound OO.OC(=O)CC(O)(C(O)=O)CC(O)=O ZYFXHKPHYKLIDV-UHFFFAOYSA-N 0.000 description 1
- KCYQMQGPYWZZNJ-BQYQJAHWSA-N hydron;2-[(e)-oct-1-enyl]butanedioate Chemical compound CCCCCC\C=C\C(C(O)=O)CC(O)=O KCYQMQGPYWZZNJ-BQYQJAHWSA-N 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
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- 239000011261 inert gas Substances 0.000 description 1
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- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
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- ISPMIYRVKUAKMX-UHFFFAOYSA-N magnesium hydrogen phosphite Chemical compound [Mg++].OP([O-])[O-] ISPMIYRVKUAKMX-UHFFFAOYSA-N 0.000 description 1
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- GVALZJMUIHGIMD-UHFFFAOYSA-H magnesium phosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O GVALZJMUIHGIMD-UHFFFAOYSA-H 0.000 description 1
- 239000004137 magnesium phosphate Substances 0.000 description 1
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- 159000000003 magnesium salts Chemical class 0.000 description 1
- YZQBYALVHAANGI-UHFFFAOYSA-N magnesium;dihypochlorite Chemical compound [Mg+2].Cl[O-].Cl[O-] YZQBYALVHAANGI-UHFFFAOYSA-N 0.000 description 1
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- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
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- GGRGTHFWHGANTA-UHFFFAOYSA-N pentane-1,3,3,5-tetracarboxylic acid Chemical compound OC(=O)CCC(C(O)=O)(C(O)=O)CCC(O)=O GGRGTHFWHGANTA-UHFFFAOYSA-N 0.000 description 1
- HWGNBUXHKFFFIH-UHFFFAOYSA-I pentasodium;[oxido(phosphonatooxy)phosphoryl] phosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O HWGNBUXHKFFFIH-UHFFFAOYSA-I 0.000 description 1
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- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052615 phyllosilicate Inorganic materials 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- SATVIFGJTRRDQU-UHFFFAOYSA-N potassium hypochlorite Chemical compound [K+].Cl[O-] SATVIFGJTRRDQU-UHFFFAOYSA-N 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 125000003595 primary aliphatic amine group Chemical group 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- NJEVMKZODGWUQT-UHFFFAOYSA-N propane-1,1,3,3-tetracarboxylic acid Chemical compound OC(=O)C(C(O)=O)CC(C(O)=O)C(O)=O NJEVMKZODGWUQT-UHFFFAOYSA-N 0.000 description 1
- JXHDZGPVOXKUSI-UHFFFAOYSA-N propane-1,2,2,3-tetracarboxylic acid Chemical compound OC(=O)CC(C(O)=O)(C(O)=O)CC(O)=O JXHDZGPVOXKUSI-UHFFFAOYSA-N 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- 235000002639 sodium chloride Nutrition 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical group [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- 239000012418 sodium perborate tetrahydrate Substances 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 235000019830 sodium polyphosphate Nutrition 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- IBDSNZLUHYKHQP-UHFFFAOYSA-N sodium;3-oxidodioxaborirane;tetrahydrate Chemical compound O.O.O.O.[Na+].[O-]B1OO1 IBDSNZLUHYKHQP-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 230000019635 sulfation Effects 0.000 description 1
- 238000005670 sulfation reaction Methods 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
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- 230000001629 suppression Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000007885 tablet disintegrant Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
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- 229940095064 tartrate Drugs 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 150000004685 tetrahydrates Chemical class 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 229940038773 trisodium citrate Drugs 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 238000004457 water analysis Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/3719—Polyamides or polyimides
-
- 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/04—Preparatory processes
-
- 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/08—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids
- C08G69/10—Alpha-amino-carboxylic 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Description
(a)(i)アスパラギン酸、
(ii)1〜25モル%、好ましくは2〜20モル%、好ましくは3〜15モル%、好ましくは3〜10モル%、特に好ましくは3〜8モル%の酸触媒、及び
(iii)任意選択で、水
の混合物を反応器中で接触させるステップ、
(b)(a)による混合物を、水の蒸留除去なしに還流冷却下で、100〜220℃、好ましくは120〜200℃、好ましくは140〜200℃、好ましくは150〜200℃、特に好ましくは160〜180℃の反応温度で、少なくとも1%、好ましくは少なくとも3%、好ましくは少なくとも5%、好ましくは少なくとも7%、好ましくは15%までの程度まで、特に好ましくは10%までの程度までの変換率(degree of conversion)まで加熱するステップ、
(c)(b)による反応混合物を、水の同時蒸留除去と共に、170〜250℃、特に好ましくは200〜230℃で重縮合させるステップ、
(d)(c)による重縮合物を塩基の添加によって加水分解するステップ、並びに
(e)任意選択で(d)で得られたポリアスパラギン酸の塩を酸性化するステップ
を含む、方法に関する。
C=(X-Y)/X
(式中、X[g]は、ステップ(b)の開始前の規定量の反応混合物のアスパラギン酸含有量である)
によって計算され得る。
(a)本発明によって調製されるか又は調製可能な、及び本明細書に記載される、1〜20重量%、好ましくは1〜15重量%、特に好ましくは2〜12重量%のポリアスパラギン酸;
(b)0〜50重量%の錯化剤;
(c)0.1〜80重量%のビルダー及び/又はコビルダー(co-builder);
(d)0.1〜20重量%の非イオン性界面活性剤;
(e)0〜30重量%の漂白剤、漂白活性化剤及び漂白触媒;
(f)0〜8重量%の酵素;並びに
(g)0〜50重量%の添加剤
を含む。
R1-O-(CH2CH2O)a-(CHR2CH2O)b-R3 (I)
(式中、R1は、8〜22個の炭素原子を有する直鎖又は分岐アルキル基であり、
R2及びR3は、それぞれ独立して、水素、又は1〜10個の炭素原子を有する直鎖若しくは分岐アルキル基若しくはHであり、ここで、R2は、好ましくはメチルであり、
a及びbは、それぞれ独立して0〜300である)
の界面活性剤を含む。好ましくは、a=1〜100であり、b=0〜30である。
R4-O-[CH2CH(CH3)O]c[CH2CH2O]d[CH2CH(CH3)O]eCH2CH(OH)R5 (II)
(式中、R4は、4〜22個の炭素原子を有する直鎖若しくは分岐脂肪族ヒドロカルビル基又はその混合物であり、
R5は、2〜26個の炭素原子を有する直鎖若しくは分岐ヒドロカルビル基であるか、又はその混合物を指し、
c及びeは、0〜40の値を有し、
dは、少なくとも15の値である)
の界面活性剤も適当である。
R6O-(CH2CHR7O)f(CH2CH2O)g(CH2CHR8O)h-CO-R9 (III)
(式中、R6は、8〜16個の炭素原子を有する分岐又は非分岐アルキル基であり、
R7、R8は、それぞれ独立して、H、又は1〜5個の炭素原子を有する分岐若しくは非分岐アルキル基であり、
R9は、5〜17個の炭素原子を有する非分岐アルキル基であり、
f、hは、それぞれ独立して、1〜5の数であり、
gは、13〜35の数である)
の界面活性剤も適当である。
は、当業者に公知の代表的なものであり得る。漂白剤は、酸素漂白剤及び塩素漂白剤に細分される。使用される酸素漂白剤は、アルカリ金属過ホウ酸塩及びその水和物、並びにまたアルカリ金属過炭酸塩である。これに関連する好ましい漂白剤は、一-又は四水和物の形態の過ホウ酸ナトリウム、過炭酸ナトリウム又は過炭酸ナトリウムの水和物である。同様に酸素漂白剤として使用可能なものは、パーサルフェート及び過酸化水素である。典型的な酸素漂白剤はまた、有機過酸、例えば、過安息香酸、ペルオキシ-アルファ-ナフトン酸、ペルオキシラウリン酸、ペルオキシステアリン酸、フタルイミドペルオキシカプロン酸、1,12-ジペルオキシドデカンジオン酸、1,9-ジペルオキシアゼライン酸、ジペルオキソイソフタル酸(diperoxoisophthalic acid)又は2-デシルジペルオキシブタン-1,4-ジオン酸である。さらに、以下の酸素漂白剤も、食器洗浄組成物に使用されてもよい:カチオン性過酸(これは、US 5,422,028、US 5,294,362及びUS 5,292,447に記載されている)、及びスルホニルペルオキシ酸(これは、US 5,039,447に記載されている)。酸素漂白剤は、一般に、食器洗浄組成物全体に基づいて、0.1〜30重量%、好ましくは1〜20重量%、より好ましくは3〜15重量%の量で使用されてもよい。
(AL)本明細書に記載され及び本発明によって使用される、0.1〜20重量%の少なくとも1種のポリアスパラギン酸、
(BL)1〜80重量%の界面活性剤、
(CL)0.1〜50重量%のビルダー、コビルダー及び/又は錯化剤、
(DL)0〜20重量%の漂白系、
(EL)0.1〜60重量%の洗剤又は清浄組成物成分、すなわち、他の通例の成分、例えば、アルカリ担体、消泡剤、酵素(例えば、リパーゼ、プロテアーゼ、アミラーゼ、セルラーゼ)、染料、芳香剤、香料担体、灰色化抑制剤、染料移行抑制剤、色保護添加剤、繊維保護添加剤、光学的増白剤(optical brightener)、防汚ポリエステル、腐食抑制剤、殺細菌剤及び防腐剤、有機溶媒、可溶化剤、pH調整剤、ヒドロトロープ、増粘剤、レオロジー調整剤及び/又はアルカノールアミン、並びに
(FL)0〜98.7重量%の水
を含む、液体又はゲル形態の洗剤及び清浄組成物に関する。(AL)〜(FL)の総合計は、100重量%である。
(AF)本明細書に記載され及び本発明によって使用される0.1〜20重量%の少なくとも1種のポリアスパラギン酸、
(BF)1〜50重量%の界面活性剤、
(CF)0.1〜70重量%のビルダー、コビルダー及び/又は錯化剤、
(DF)0〜30重量%の漂白系、並びに
(EF)0.1〜70重量%の洗剤又は清浄組成物成分、すなわち、他の通例の成分、例えば、調整剤(例えば、硫酸ナトリウム)、消泡剤、酵素(例えば、リパーゼ、プロテアーゼ、アミラーゼ、セルラーゼ)、染料、芳香剤、香料担体、灰色化抑制剤、染料移行抑制剤、色保護添加剤、繊維保護添加剤、光学的増白剤、防汚ポリエステル、腐食抑制剤、殺細菌剤及び防腐剤、溶解促進剤、崩壊剤、加工助剤及び/又は水
を含む、固形洗剤及び清浄組成物に関する。(AF)〜(EF)からの成分の総合計は、100重量%である。
ロック単位を有するブロックコポリマーだけでなく、EO-PO-EOコポリマー又はPO-EO-POコポリマーも使用することが可能である。当然に、EO及びPO単位が、ブロックでないが、ランダム分布である、混合アルコキシル化非イオン性界面活性剤を使用することも可能である。このような生成物は、脂肪アルコール上でのエチレンオキシド及びプロピレンオキシドの同時作用によって得ることができる。
R10O(G)i (V)
(式中、R10は、8〜22個、好ましくは12〜18個の炭素原子を有する、第一級直鎖又はメチル分岐、特に2-メチル分岐の脂肪族基であり、Gは、5又は6個の炭素原子を有するグリコシド単位、好ましくはグルコースである)
のアルキルグリコシドを使用することも可能である。モノグリコシド及びオリゴグリコシドの分布を示す、オリゴマー化度iは、1〜10の任意の所望の数であり、好ましくはiは、1.2〜1.4である。
のポリヒドロキシ脂肪酸アミドである。ポリヒドロキシ脂肪酸アミドは、典型的にはアンモニア、アルキルアミン又はアルカノールアミンによる還元糖の還元アミノ化、及びその後の、脂肪酸、脂肪酸アルキルエステル又は脂肪酸クロリドによるアシル化によって得ることができる公知の物質である。これに関連して、ポリヒドロキシ脂肪酸アミドの群にはまた、式(VII)
の化合物が含まれる。R17は、好ましくは糖、例えば、グルコース、フルクトース、マルトース、ラクトース、ガラクトース、マンノース又はキシロースの還元アミノ化によって得られる。次いで、N-アルコキシ-又はN-アリールオキシ-置換化合物は、例えば、WO95/07331に従い、触媒としてのアルコシドの存在下での脂肪酸メチルエステルとの反応によって、所望のポリヒドロキシ脂肪酸アミドに変換され得る。
- C7〜C25アルキルアミン、
- N,N-ジメチル-N-(ヒドロキシ-C7〜C25アルキル)アンモニウム塩、
- アルキル化剤で四級化されたモノ-及びジ(C7〜C25アルキル)ジメチルアンモニウム化合物、
- エステルクワット、特にC8〜C22カルボン酸でエステル化された第四級エステル化モノ-、ジ-及びトリアルカノールアミン、
- イミダゾリンクワット、特に式VIII又は式IX
R18 C1〜C25-アルキル又はC2〜C25-アルケニル、
R19 C1〜C4-アルキル又はヒドロキシ-C1〜C4-アルキル、
R20 C1〜C4-アルキル、ヒドロキシ-C1〜C4-アルキル又はR1-(CO)-R21-(CH2)j-(R21:-O-又は-NH-;j:2又は3)基、
ここで、少なくとも1個のR18基は、C7〜C22アルキルである)
の1-アルキルイミダゾリニウム塩
である。
- イオン交換特性を有する結晶性及び非晶性アルミノシリケート、例えば、特にゼオライト:様々なタイプのゼオライト、特に、ゼオライトA、X、B、P、MAP及びHS(それらのNa形態、又はNaが他のカチオン、例えば、Li、K、Ca、Mg又はアンモニウムと部分的に交換されている形態)、
- 結晶性シリケート、例えば、特にジシリケート(disilicate)及び層状シリケート(sheet silicate)、例えば、δ-及びβ-Na2Si2O5。シリケートは、それらのアルカリ金属、アルカリ土類金属又はアンモニウム塩の形態で使用することができ、Na、Li及びMgのケイ酸塩が優先される、
- 非晶性シリケート、例えば、メタケイ酸ナトリウム及び非晶性ジシリケート、
- カーボネート及びハイドロゲンカーボネート:これらは、それらのアルカリ金属、アルカリ土類金属又はアンモニウムの塩の形態で使用され得る。Na、Li及びMgの炭酸塩及び炭酸水素塩、特に炭酸ナトリウム及び/又は炭酸水素ナトリウム、並びに
- ポリホスフェート、例えば、三リン酸五ナトリウム
である。
- 低分子量カルボン酸、例えば、クエン酸、疎水性変性クエン酸、例えば、アガリン酸、リンゴ酸、酒石酸、グルコン酸、グルタル酸、コハク酸、イミドジコハク酸、オキシジコハク酸、プロパントリカルボン酸、ブタンテトラカルボン酸、シクロペンタンテトラカルボン酸、アルキル-及びアルケニルコハク酸及びアミノポリカルボン酸、例えば、ニトリロトリ酢酸、β-アラニンジ酢酸、エチレンジアミン四酢酸、セリンジ酢酸、イソセリンジ酢酸、N-(2-ヒドロキシエチル)イミノ酢酸、エチレンジアミンジコハク酸、グルタミン酸ジ酢酸並びにメチル-及びエチルグリシンジ酢酸又はそれらのアルカリ金属塩;特に好ましい錯化剤は、メチルグリシンジ酢酸及びその塩、とりわけ、そのモノ-、ジ-及びトリナトリウム、-カリウム、-リチウム及び-アンモニウム塩である。メチルグリシンジ酢酸の塩は、D-及びL-エナンチオマーが等モル混合物で存在することを意味するラセミ形態であってもよく、又は一方のエナンチオマー、例えば、L-エナンチオマーが、過剰に存在してもよい。
- オリゴマー及びポリマーカルボン酸、例えば、アクリル酸のホモポリマー、アクリル酸とスルホン酸基含有コモノマー、例えば、2-アクリルアミド-2-メチルプロパンスルホン酸(AMPS)、アリルスルホン酸及びビニルスルホン酸とのコポリマー、オリゴマレイン酸、マレイン酸とアクリル酸、メタクリル酸又はC2〜C22オレフィン、例えば、イソブテン又は長鎖α-オレフィン、ビニル-C1〜C8アルキルエーテル、酢酸ビニル、プロピオン酸ビニル、C1〜C8アルコールの(メタ)アクリル酸エステル及びスチレンとのコポリマー。アクリル酸のホモポリマー、及びアクリル酸とマレイン酸又はAMPSとのコポリマーが優先される。オリゴマー及びポリマーカルボン酸は、酸形態で又はそのナトリウム塩として使用される;
- ホスホン酸、例えば、1-ヒドロキシエチレン(1,1-ジホスホン酸)、アミノトリ(メチレンホスホン酸)、エチレンジアミンテトラ(メチレンホスホン酸)及びジエチレントリアミンペンタ(メチレンホスホン酸)並びにそれらのアルカリ金属塩
が含まれる。
項1
ポリアスパラギン酸を生成させるための方法であって、以下のステップ:
(a)(i)アスパラギン酸、
(ii)1〜25モル%の酸触媒、及び
(iii)任意選択で、水
の混合物を反応器中で接触させるステップ、
(b)(a)による混合物を、水の蒸留除去なしに還流冷却下で、100〜220℃の反応温度で、少なくとも1%の、アスパラギン酸の変換率まで加熱するステップ、
(c)(b)による反応混合物を、水の同時蒸留除去と共に、170〜250℃で重縮合させるステップ、
(d)(c)による重縮合物を塩基の添加によって加水分解するステップ、並びに
(e)任意選択で(d)で得られたポリアスパラギン酸の塩を酸性化するステップ
を含む方法。
項2
3〜15モル%の酸触媒が添加される、項1に記載の方法。
項3
酸触媒が、メタンスルホン酸である、項1又は2に記載の方法。
項4
重縮合が、200〜250℃で行われる、項1から3のいずれか一項に記載の方法。
項5
塩基が、水酸化ナトリウム水溶液、水酸化カリウム水溶液、水酸化カルシウム、水酸化バリウム、炭酸ナトリウム、炭酸カリウム、アンモニア及び水酸化アンモニウムからなる群から選択される、項1から4のいずれか一項に記載の方法。
項6
酸性化が、鉱酸又は酸性イオン交換体で行われる、項1から5のいずれか一項に記載の方法。
項7
ステップ(b)において、アスパラギン酸の変換率が少なくとも5%である、項1から6のいずれか一項に記載の方法。
項8
ステップ(b)において、温度が、160〜180℃である、項1から7のいずれか一項に記載の方法。
項9
項1〜8のいずれか一項によって得ることができるポリアスパラギン酸を含む組成物であって、食器洗浄組成物、洗剤組成物及び清浄組成物からなる群から選択される、組成物。
項10
食器洗浄剤、洗剤及び清浄剤における添加剤としての、項1から9のいずれか一項によって得ることができるポリアスパラギン酸の使用。
項11
食器洗浄剤が、機械的食器洗浄用である、項10に記載の使用。
項12
導水システムにおけるスケール抑制剤又は分散剤としての、項1から9のいずれか一項によって得ることができるポリアスパラギン酸の使用。
以下の実施例は、本発明を例証するために役立つものであり、それに対する制限と理解されてはならない。
133.1gのL-アスパラギン酸、30gの水及び4.81gのメタンスルホン酸(100%)を、撹拌機及び温度センサーを備えた2l容量のガラス反応器に最初に投入した。この反応混合物を、蒸留による水の同時除去と共に穏やかな窒素流下で攪拌しながら210℃〜220℃の縮合温度に加熱した。15分後、非常に粘性の高いペーストが形成し、これはもはや攪拌することができなかった。さらに15分以内に、反応生成物が、固体塊に固化していた。反応器を室温に冷却した。ケーキ化した反応混合物をへらで反応器から取り出し、乳棒及び乳鉢を使用して粉末に粉砕した。粉砕された反応混合物を反応器に再度入れ、穏やかな窒素流下で攪拌しながら210℃〜220℃の縮合温度に加熱し、この温度で蒸留による水の同時除去と共にさらに5.5時間重縮合させた。ポリアスパラギン酸のナトリウム塩水溶液を調製するために、100gの冷却反応生成物を100gの水に分散させ、この混合物を70℃に加熱し、この温度でpHが7〜9の範囲であるように十分な50%水酸化ナトリウム水溶液を添加した。水に分散された粉末は徐々に溶解し、ポリアスパラギン酸の透明なナトリウム塩水溶液が得られた。重量平均分子量Mwは、7700g/モルであった。
266.2gのL-アスパラギン酸、60gの水及び9.62gのメタンスルホン酸を、0.7lのLIST Discotherm B反応器に最初に投入した。反応器内容物を、蒸留による水の同時除去と共に穏やかな窒素流下で1分当たり20回転で攪拌しながら230℃の縮合温度に加熱した。15分後、非常に粘性が高い粘着性のペーストが形成され、高いトルク増加が観測された。さらに15分後、反応生成物は固体塊に固化し、撹拌機シャフトは最終的に停止した。室温に冷却後、ケーキ化した反応混合物をへらによって反応器から取り出し、乳棒及び乳鉢を使用して粉末に粉砕した。粉砕された反応混合物を反応器に再度入れ、穏やかな窒素流下で攪拌しながら230℃の縮合温度に加熱し、この温度で蒸留による水の同時除去と共にさらに5.5時間重縮合させた。ポリアスパラギン酸のナトリウム塩水溶液を得るための得られた最終生成物の加水分解は、C1に記載したとおりに行った。重量平均分子量Mwは、7700g/モルであった。
266.2gのL-アスパラギン酸、10gの水及び13.7gのメタンスルホン酸(水中70%)を、撹拌機及び温度センサーを備えた2l容量のガラス反応器に最初に投入した。反応器内容物を、還流冷却下、170〜180℃の温度で1分当たり20回転で攪拌した。試料を、30分後、90分後、120分後及び180分後のそれぞれの場合において採取し、L-アスパラギン酸の変換率を決定した(以下に記載されるとおりに測定した):
30分後のL-アスパラギン酸の変換率は、2.0%であった。
90分後のL-アスパラギン酸の変換率は、5.2%であった。
120分後のL-アスパラギン酸の変換率は、9.5%であった。
180分後のL-アスパラギン酸の変換率は、8.5%であった。
266.2gのL-アスパラギン酸、10gの水及び13.7gのメタンスルホン酸(水中70%)を、0.7lのLIST Discotherm B反応器に最初に投入した。反応器内容物を、1分当たり20回転で攪拌しながら170〜180℃の温度で還流冷却下で2時間加熱した。このステップ後のL-アスパラギン酸の変換率は、9.5%であった(以下に記載されるとおりに測定した)。次いで、この反応混合物を、穏やかな窒素流下で攪拌しながら210℃〜220℃の縮合温度に加熱し、この温度で蒸留による水の同時除去と共に5時間重縮合させた。反応混合物のケーキ化、したがって装置の停止は、起こらなかった。へら又は乳鉢による手作業の粉砕は必要なかった。ポリアスパラギン酸のナトリウム塩水溶液を得るための得られた最終生成物の加水分解は、C1に記載したとおりに行った。重量平均分子量Mwは、7680g/モルであった。
266.2gのL-アスパラギン酸、20gの水及び13.7gのメタンスルホン酸(水中70%)を、0.7lのLIST Discotherm B反応器に最初に投入した。反応器内容物を、1分当たり20回転で攪拌しながら170〜180℃の温度で還流冷却下で1時間加熱した。このステップ後のL-アスパラギン酸の変換率は、2.0%であった(以下に記載されるとおりに測定した)。次いで、この反応混合物を、穏やかな窒素流下で攪拌しながら210℃〜220℃の縮合温度に加熱し、この温度で蒸留による水の同時除去と共に5時間重縮合させた。反応混合物のケーキ化、したがって装置の停止は、起こらなかった。へら又は乳鉢による手作業の粉砕は必要なかった。ポリアスパラギン酸のナトリウム塩水溶液を得るための得られた最終生成物の加水分解は、C1に記載したとおりに行った。重量平均分子量Mwは、7530g/モルであった。
266.2gのL-アスパラギン酸、10gの水及び18.5gのリン酸(水中85%)を、撹拌機及び温度センサーを備えた2l容量のガラス反応器に最初に投入した。反応器内容物を、1分当たり20回転で攪拌しながら170〜180℃の温度で還流冷却下で2時間加熱した。このステップ後のL-アスパラギン酸の変換率は、3.7%であった(以下に記載されるとおりに測定した)。次いで、この反応混合物を、穏やかな窒素流下で攪拌しながら210℃〜220℃の縮合温度に加熱し、この温度で蒸留による水の同時除去と共に4.5時間重縮合させた。反応混合物のケーキ化、したがって装置の停止は、起こらなかった。へら又は乳鉢による手作業の粉砕は必要なかった。ポリアスパラギン酸のナトリウム塩水溶液を得るための得られた最終生成物の加水分解は、C1に記載したとおりに行った。重量平均分子量Mwは、9780g/モルであった。
266.2gのL-アスパラギン酸及び9.61gのメタンスルホン酸(100%)を、撹拌機及び温度センサーを備えた2l容量のガラス反応器に最初に投入した。反応器内容物を、1分当たり20回転で攪拌しながら170〜180℃の温度で還流冷却下で1.5時間加熱した。このステップ後のL-アスパラギン酸の変換率は、5.2%であった(以下に記載されるとおりに測定した)。次いで、この反応混合物を、穏やかな窒素流下で攪拌しながら210℃〜220℃の縮合温度に加熱し、この温度で蒸留による水の同時除去と共に6時間重縮合させた。反応混合物のケーキ化、したがって装置の停止は、起こらなかった。へら又は乳鉢による手作業の粉砕は必要なかった。ポリアスパラギン酸のナトリウム塩水溶液を得るための得られた最終生成物の加水分解は、C1に記載したとおりに行った。重量平均分子量Mwは、8300g/モルであった。
実施例の重量平均又は数平均分子量(Mw及びMn)は、以下の条件下でGPC(ゲル浸透クロマトグラフィー)により決定した:
変換率Cを決定するために、ステップ(b)後の反応混合物中の未反応モノマーのアスパラギン酸の割合を決定した。このために、ステップ(b)後に得られた100mgの初期縮合物を、50mlのガラスアンプル中に秤量し、9.9mLの1N HClを添加し、この混合物を350rpmで3時間攪拌した。次いで、試料をSpartan 30mm/0.45μm RCシリンジフィルター(GE Healthcare)に通してろ過し、水で1:10(v/v)に希釈した。この希釈溶液のアスパラギン酸含有量Yを、高性能液体クロマトグラフィー(HPLC)により、
C=(X-Y)/X
(ここで、Xは、ステップ(b)の開始前の100mgの反応混合物中のアスパラギン酸含有量である)
に従って、決定した。
C=(91.8mg-90mg)/91.8mg=2.0%
であった。
C=(91.8mg-87mg)/91.8mg=5.2%
であった。
C=(91.8mg-83mg)/91.8mg=9.5%
であった。
C=(91.8mg-84mg)/91.8mg=8.5%
であった。
Claims (8)
- ポリアスパラギン酸を生成させるための方法であって、以下のステップ:
(a)(i)アスパラギン酸、
(ii)1〜25モル%の酸触媒、及び
(iii)任意選択で、水
の混合物を反応器中で接触させるステップ、
(b)(a)による混合物を、水の蒸留除去なしに還流冷却下で、100〜220℃の反応温度で加熱して、少なくとも1%の、アスパラギン酸の変換率まで前縮合させるステップ、
(c)(b)による反応混合物を、水の同時蒸留除去と共に、170〜250℃で重縮合させるステップ、
(d)(c)による重縮合物を塩基の添加によって加水分解するステップ、並びに
(e)任意選択で(d)で得られたポリアスパラギン酸の塩を酸性化するステップ
を含む方法。 - 3〜15モル%の酸触媒が添加される、請求項1に記載の方法。
- 酸触媒が、メタンスルホン酸である、請求項1又は2に記載の方法。
- 重縮合が、200〜250℃で行われる、請求項1から3のいずれか一項に記載の方法。
- 塩基が、水酸化ナトリウム水溶液、水酸化カリウム水溶液、水酸化カルシウム、水酸化バリウム、炭酸ナトリウム、炭酸カリウム、アンモニア及び水酸化アンモニウムからなる群から選択される、請求項1から4のいずれか一項に記載の方法。
- 酸性化が、鉱酸又は酸性イオン交換体で行われる、請求項1から5のいずれか一項に記載の方法。
- ステップ(b)において、アスパラギン酸の変換率が少なくとも5%である、請求項1から6のいずれか一項に記載の方法。
- ステップ(b)において、温度が、160〜180℃である、請求項1から7のいずれか一項に記載の方法。
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US5552517A (en) | 1995-03-03 | 1996-09-03 | Monsanto Company | Production of polysuccinimide in an organic medium |
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US5837663A (en) | 1996-12-23 | 1998-11-17 | Lever Brothers Company, Division Of Conopco, Inc. | Machine dishwashing tablets containing a peracid |
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