JP2016532763A - ポリアスパラギン酸の製造方法 - Google Patents
ポリアスパラギン酸の製造方法 Download PDFInfo
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- JP2016532763A JP2016532763A JP2016541898A JP2016541898A JP2016532763A JP 2016532763 A JP2016532763 A JP 2016532763A JP 2016541898 A JP2016541898 A JP 2016541898A JP 2016541898 A JP2016541898 A JP 2016541898A JP 2016532763 A JP2016532763 A JP 2016532763A
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- acid
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- polyaspartic acid
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- 229920000805 Polyaspartic acid Polymers 0.000 title claims abstract description 83
- 108010064470 polyaspartate Proteins 0.000 title claims abstract description 82
- 238000000034 method Methods 0.000 title claims abstract description 44
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- 239000012459 cleaning agent Substances 0.000 claims abstract description 7
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 66
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- 108090000790 Enzymes Proteins 0.000 claims description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 22
- 235000003704 aspartic acid Nutrition 0.000 claims description 22
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- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 7
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 7
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- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 6
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- ARGDYOIRHYLIMT-UHFFFAOYSA-N n,n-dichloro-4-methylbenzenesulfonamide Chemical compound CC1=CC=C(S(=O)(=O)N(Cl)Cl)C=C1 ARGDYOIRHYLIMT-UHFFFAOYSA-N 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- KKEVZZILFAOSIL-UHFFFAOYSA-N n-chloro-n-(chlorocarbamoyl)benzamide Chemical compound ClNC(=O)N(Cl)C(=O)C1=CC=CC=C1 KKEVZZILFAOSIL-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000004967 organic peroxy acids Chemical class 0.000 description 1
- 150000002923 oximes Chemical group 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000002245 particle Substances 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
- 229960003330 pentetic acid Drugs 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- PATMLLNMTPIUSY-UHFFFAOYSA-N phenoxysulfonyl 7-methyloctanoate Chemical compound CC(C)CCCCCC(=O)OS(=O)(=O)OC1=CC=CC=C1 PATMLLNMTPIUSY-UHFFFAOYSA-N 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
- 229910052698 phosphorus 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
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920005646 polycarboxylate Polymers 0.000 description 1
- 229910052573 porcelain Inorganic materials 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
- IFIDXBCRSWOUSB-UHFFFAOYSA-M potassium;1,5-dichloro-4,6-dioxo-1,3,5-triazin-2-olate Chemical compound [K+].ClN1C(=O)[N-]C(=O)N(Cl)C1=O IFIDXBCRSWOUSB-UHFFFAOYSA-M 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002335 preservative effect 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
- 235000019260 propionic acid Nutrition 0.000 description 1
- YLQLIQIAXYRMDL-UHFFFAOYSA-N propylheptyl alcohol Chemical compound CCCCCC(CO)CCC YLQLIQIAXYRMDL-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000005581 pyrene group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 229940071207 sesquicarbonate Drugs 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate 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
- MSFGZHUJTJBYFA-UHFFFAOYSA-M sodium dichloroisocyanurate Chemical compound [Na+].ClN1C(=O)[N-]C(=O)N(Cl)C1=O MSFGZHUJTJBYFA-UHFFFAOYSA-M 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- QUCDWLYKDRVKMI-UHFFFAOYSA-M sodium;3,4-dimethylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1C QUCDWLYKDRVKMI-UHFFFAOYSA-M 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical group [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical compound S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
- 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
- 235000002906 tartaric acid Nutrition 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
- 239000004753 textile Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 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
- 150000005691 triesters Chemical class 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical group OOO JSPLKZUTYZBBKA-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
- 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
- 230000002087 whitening effect Effects 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- 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
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1092—Polysuccinimides
-
- 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
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/14—Polyamide-imides
-
- 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
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/0036—Soil deposition preventing compositions; Antiredeposition agents
-
- 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
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- 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
- C08G2230/00—Compositions for preparing biodegradable polymers
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W10/00—Technologies for wastewater treatment
- Y02W10/30—Wastewater or sewage treatment systems using renewable energies
- Y02W10/37—Wastewater or sewage treatment systems using renewable energies using solar energy
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- Chemical & Material Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Detergent Compositions (AREA)
- Polyamides (AREA)
- Inorganic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Abstract
Description
(1)洗浄組成物、洗濯組成物、例えば食器洗浄組成物に添加剤として、特に食器の機械的洗浄用の無リン酸の洗浄組成物及び洗濯組成物の添加物として、液体及び固体洗剤の添加物として、並びに、スケール抑制及び/又は分散のために導水システムに使用され、
(2)容易に可変の方式で、それらのポリマー構造及び分子量を調整することが可能であり、
(3)高い生成物収率を有し、且つ、
(4)生物分解が可能である、
ポリマーの製造方法を提供することにある。
(i)重縮合する工程、該工程が、
(a)アスパラギン酸を、
(b)(a)に使用されたアスパラギン酸の量に基づいて、1モル%〜15モル%、好ましくは2モル%〜13モル%、特に好ましくは3モル%〜10モル%のメタンスルホン酸の存在下で、
170℃〜230℃の温度で、1分〜50時間の期間に重縮合し、
(ii)その後、塩基を添加して重縮合物を加水分解する工程、及び、
(iii)任意に、鉱酸、例えば硫酸又は塩酸で、工程(ii)に得られたポリアスパラギン酸の塩を酸性化する工程、
を含む、6000g/mol〜15000g/molの重量平均分子量(MW)を有するポリアスパラギン酸の製造方法に関する。
(a)1質量%〜20質量%、好ましくは1質量%〜15質量%、特に好ましくは2質量%〜12質量%の本発明及びここの記載によって製造又は調製できるポリアスパラギン酸、
(b)0質量%〜50質量%の錯化剤、
(c)0.1質量%〜80質量%のビルダー及び/又はコビルダー
(d)0.1質量%〜20質量%の非イオン界面活性剤、
(e)0質量%〜30質量%の漂白剤、漂白活性剤及び漂白触媒、
(f)0質量%〜8質量%の酵素、及び、
(g)0質量%〜50質量%の添加剤、
を含む。
R1-O-(CH2CH2O)a-(CHR2CH2O)b-R3 (I),
式中、R1が、8個〜22個の炭素原子を有する直鎖又は分枝アルキル残基(residue)であり、
R2及びR3が、それぞれに独立して、水素、又は1個〜10個の炭素原子若しくはHを有する直鎖若しくは分枝アルキル残基であり、そのうち、好ましくはR2がメチルであり、
a及びbが、それぞれに独立して、0〜300である。好ましくは、aは1〜100であり、bは0〜30である。
R4-O-[CH2CH(CH3)O]c[CH2CH2O]d[CH2CH(CH3)O]eCH2CH(OH)R5 (II),
式中、R4が、4個〜22個の炭素原子を有する直鎖状又は分枝状脂肪族炭化水素残基又はそれらの混合物であり、
R4が、2個〜26個の炭素原子を有する直鎖状又は分枝状脂肪族炭化水素残基であり、又はそれらの混合物に関し、
c及びeが、0〜40の間の数値を有し、
dが少なくとも15の数値である。
R6O-(CH2CHR7O)f(CH2CH2O)g(CH2CHR8O)h-CO-R9 (III),
式中、R6が、8個〜16個の炭素原子を有する直鎖状又は非分枝状アルキル残基であり、
R7、R8が、それぞれに独立して、H、又は1個〜5個の炭素原子を有する直鎖状又は非分枝状アルキル残基であり、
R9が、5個〜17個の炭素原子を有する非分枝状アルキル残基であり、
f、hが、それぞれに独立して、1〜5の数字であり、
gが、13〜35の数字である。
(AL)0.1質量%〜20質量%の、ここに記載され、且つ本発明に使用される少なくとも1種のポリアスパラギン酸、
(BL)1質量%〜80質量%の界面活性剤、
(CL)0.1質量%〜50質量%のビルダー、コビルダー及び/又は錯化剤、
(DL)0質量%〜20質量%の漂白系、
(EL)0.1質量%〜60質量%の洗剤又は洗浄成分、換言すれば、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、香料、香料担体、グレー化抑制剤、転染抑制剤、着色防止添加剤、ファイバー保護添加剤、光学的増白剤、防汚ポリエステル、腐食防止剤、殺菌剤、防腐剤、有機溶媒、溶解剤、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質量%〜98.7質量%の水、
を含む液体又はゲル状の洗剤及び洗浄組成物に関する。(AL)〜(FL)の合計は100質量%である。
(AF)0.1質量%〜20質量%の、ここに記載され、且つ本発明に使用される少なくとも1種のポリアスパラギン酸、
(BF)1質量%〜50質量%の界面活性剤、
(CF)0.1質量%〜70質量%のビルダー、コビルダー及び/又は錯化剤、
(DF)0質量%〜30質量%の漂白系、並びに、
(EF)0.1質量%〜70質量%の洗剤又は洗浄成分、換言すれば、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、香料、香料担体、グレー化抑制剤、転染抑制剤、着色防止添加剤、ファイバー保護添加剤、光学的増白剤、防汚ポリエステル、腐食防止剤、殺菌剤、防腐剤、溶解促進剤、崩壊剤、処理補助剤及び/又は水、
を含む固体洗剤及び洗浄組成物に関する。(AF)〜(EF)の合計は100質量%である。
R10O(G)i (V)
(式中、R10が、8個〜22個、好ましくは12個〜18個の炭素原子を有する第1級の直鎖又は分枝状、特に2−メチル−分枝の脂肪族残基であり、Gが、5個〜6個の炭素原子を有するグリコシドユニット、好ましくはグルコースである)の使用も可能である。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iの程度は、1〜10の間の任意の所望の数字である。好ましくは、iが1.2〜1.4である。
− 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、
− アルキル化剤により四級化されたモノ−及びジ(C7〜C25−アルキル)ジメチルアンモニウム化合物、
− エステルクォート、特にC8〜C22−カルボン酸によりエステル化される第4級エステル化モノ−、ジ−及びトリエタノールアミン、
− イミダゾリンクォート、特に一般式VIII又はIXの1−アルキルイミダゾリニウム塩であり、
R18は、C1〜C25−アルキル、又はC2〜C25−アルケニルであり、
R19は、C1〜C4−アルキル、又はヒドロキシ−C1〜C4−アルキルであり、
R20は、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が−O−又は−NH−であり、jが2又は3である)残基であり、
そのうち、少なくとも1つのR18残基はC7〜C22−アルキルである。
− ポリリン酸塩、例えばトリリン酸ペンタナトリウムである。
ポリアスパラギン酸の調製
ポリマー1〜6及びC2:
最初に、133.10gのL−アスパラギン酸、30gの水及び表1に記載の量のメタンスルホン酸を、撹拌器及び温度センサーを備える2リットル容量の反応器に注入した。反応混合物を、窒素の緩流下で撹拌しながら210℃〜220℃の凝縮温度まで加熱し、蒸留により水の除去をする同時にこの温度で6時間凝縮した。反応を完結させた後、得たポリアスパルトイミドを粉砕し冷却した。ポリアスパラギン酸のナトリウム塩を調製するために、凝縮工程により生成した100gのポリアスパルトイミドを100gの水に分散した。混合物を70℃まで加熱し、この温度で、pHが7〜9の範囲になるように十分な50%の水酸化ナトリウム水溶液を添加した。水に分散した粉末は徐々に溶解し、透明なポリアスパラギン酸のナトリウム塩の水溶液を得た。未反応のアスパラギン酸の残留物含有量を、1H−NMR分光法により測定した。これは、使用したアスパラギン酸に基づいて、0.5質量%未満であった。
133.10gのL−アスパラギン酸を、ロータリーエバポレーター中で210℃〜220℃の温度で2時間重縮合した。生成したポリアスパルトイミドを加水分解して、ポリマー1〜6及びC2と類似した方法でポリアスパラギン酸のナトリウム塩の水溶液を得た。重量平均分子量Mwは5400g/molであった。
US 5,457,176の実施例5の記載に従ってポリアスパラギン酸を調製した。使用したMeSO3H(3g)の量は、使用したL−アスパラギン酸(27g)の量に基づいて15.4モル%であり、その故にL−Asp:MeSO3Hのモル比は6.5:1であった。重縮合を、US 5,457,176の実施例5に記載するように240℃で行い、生成した固体塊を粉砕するために繰り返し中断しなければならなかった。得た生成物について、ここに記載のCaCO3抑制試験(表2bに参照する)を行った。
分子量(Mw及びMn)の測定
実施例の重量平均又は数平均分子量(Mw及びMn)を、下記の条件下で、GPC(ゲル浸透クロマトグラフィー)により測定した。
炭酸カルシウム抑制の試験
70℃で、水浴中で、NaHCO3と、MgSO4と、CaCl2とポリマーとの溶液を2時間振とうさせた。0.45μm Milex濾過器を通して未だに温かい溶液を濾過した後、濾液のCa含有量を、錯滴定又はCa2+選択電極により測定し、CaCO3抑制の前/後との比較により%で(式1に参照する)決定した。
Mg2+ 43mg/l
HCO3 − 1220mg/l
Na+ 460mg/l
Cl− 380mg/l
SO4 2− 170mg/l
ポリマー 3mg/l(表2aに参照する)又は1.5mg/l(表2bに参照する)
温度 70℃
時間 2時間
pH 8.0〜8.5
CaCO3抑制(%)=[(mg(Ca2+)24時間後−mg(Ca2+)24時間後の空試験値)/(mg(Ca2+)ゼロ値−mg(Ca2+)24時間後の空試験値)]x100
食器洗浄機の試験
下記の無リン処方物PF1で、ポリマーを試験した。
食器洗浄機:Miele G 1222 SCL
プログラム:65℃(予備洗浄を有する)
食器:3つのナイフ(ニッケルクロムナイフKarina、ソレックスドイツGmbH、D−75239 Eisingen)
3つの飲用グラスAmsterdam 0.2リットル
3つの朝食皿「OCEAN BLUE」(メラミン)
3つの磁器皿FLAT RIMMED PLATES 19 CM
配置:カトラリーラックにナイフ、上部バスケットにグラス、下部バスケットに皿
食器洗浄剤:18g
汚れの添加:予備洗浄の後、添加した処方物で50gのバラスト汚れ(その成分については下記に参照する)を融解する
洗浄温度:65℃
水の硬度:21°dH(Ca/Mg):HCO3 (3:1):1.35
洗浄サイクル:15、それぞれのサイクルの間に1時間停止し(10分間蓋を閉め、50分間蓋を開ける)
評価:15サイクルの後に目視による
澱粉: 0.5%のジャガイモ澱粉、2.5%のグレイビー
脂肪: 10.2%のマーガリン
蛋白質: 5.1%の卵黄、5.1%のミルク
その他: 2.5%のトマトケチャップ、2.5%のマスタード、0.1%の安息香酸、71.5%の水
本発明に従って変性されたポリアスパラギン酸を有する処方物は、特に、グラス及びナイフ上の無機及び有機の堆積に関してそれらの非常に優れたスケール抑制効果を特徴とした。さらに、それらは、食器洗剤の洗浄力を向上させ、食器からの脱水に有利であり、それで特にきれいなグラス及び光沢のある金属食器を得た。
Claims (18)
- 6000g/mol〜15000g/molの重量平均分子量(Mw)を有するポリアスパラギン酸を製造する方法であって、
(i)重縮合する工程、該工程が、
(a)アスパラギン酸を、
(b)(a)に使用されるアスパラギン酸の量に基づいて、1モル%〜15モル%のメタンスルホン酸の存在下で、
170℃〜230℃の温度で、1分〜50時間の期間に重縮合する工程であり、
(ii)その後、塩基を添加してその重縮合物を加水分解する工程、及び、
(iii)場合により、鉱酸又は酸性イオン交換体により、工程(ii)で得られたポリアスパラギン酸の塩を酸性化する工程、
を含むことを特徴とする方法。 - (a)に使用されるアスパラギン酸の量に基づいて、2モル%〜13モル%のメタンスルホン酸が、工程(i)(b)に使用される請求項1に記載の方法。
- (a)に使用されるアスパラギン酸の量に基づいて、3モル%〜10モル%のメタンスルホン酸が、工程(i)(b)に使用される請求項1又2に記載の方法。
- 工程(i)の前記重縮合が、190℃〜220℃の温度で行われる請求項1から3のいずれか一項に記載の方法。
- 製造される前記ポリアスパラギン酸の重量平均分子量(Mw)と数平均分子量(Mn)との比率が、3以下である請求項1から4のいずれか一項に記載の方法。
- 前記比率が2.5以下である請求項5に記載の方法。
- 工程(ii)に使用される前記塩基が、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6のいずれか一項に記載の方法。
- 工程(iii)に使用される前記鉱酸が硫酸又は塩酸である請求項1から7のいずれか一項に記載の方法。
- 請求項1から8のいずれか一項に記載の方法により得られるポリアスパラギン酸。
- 請求項9に記載のポリアスパラギン酸又は請求項1から8のいずれか一項に記載の方法により得られるポリアスパラギン酸を含むことを特徴とする組成物。
- 前記組成物が、食器洗浄組成物、洗剤組成物又は洗浄組成物である請求項10に記載の組成物。
- (a)1質量%〜20質量%の請求項9に記載のポリアスパラギン酸、
(b)0質量%〜50質量%の錯化剤、
(c)0.1質量%〜80質量%のビルダー及び/又はコビルダー
(d)0.1質量%〜20質量%の非イオン性界面活性剤、
(e)0質量%〜30質量%の漂白剤、漂白活性剤及び漂白触媒、
(f)0質量%〜8質量%の酵素、並びに、
(g)0質量%〜50質量%の添加剤、
を含むことを特徴とする食器洗浄組成物。 - (AF)0.1質量%〜20質量%の請求項9に記載のポリアスパラギン酸、
(BF)1質量%〜50質量%の界面活性剤、
(CF)0.1質量%〜70質量%のビルダー、コビルダー及び/又は錯化剤、
(DF)0質量%〜30質量%の漂白系、並びに、
(EF)0.1質量%〜70質量%の洗剤又は洗浄成分、
を含むことを特徴とする固体の洗剤組成物又は洗浄組成物。 - (AL)0.1質量%〜20質量%の請求項9に記載のポリアスパラギン酸、
(BL)1質量%〜80質量%の界面活性剤、
(CL)0.1質量%〜50質量%のビルダー、コビルダー及び/又は錯化剤、
(DL)0質量%〜20質量%の漂白系、
(EL)0.1質量%〜60質量%の洗剤又は洗浄成分、並びに、
(FL)0質量%〜98.7質量%の水、
を含むことを特徴とする液体又はゲル状の洗剤組成物及び洗浄組成物。 - 請求項9に記載の前記ポリアスパラギン酸又は請求項1から8のいずれか一項に記載の方法により得られる前記ポリアスパラギン酸をスケール抑制剤及び/又は分散剤として使用する方法。
- 導水システムに、請求項15に記載の前記ポリアスパラギン酸をスケール抑制剤及び/又は分散剤として使用する方法。
- 食器洗剤、洗剤又は洗浄剤に、請求項9に記載の前記ポリアスパラギン酸又は請求項1から8のいずれか一項に記載の方法により得られる前記ポリアスパラギン酸を添加物として使用する方法。
- 前記食器洗剤が食器の機械的洗浄用である請求項17に記載の使用方法。
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JP2021024997A (ja) * | 2019-08-08 | 2021-02-22 | 三井化学株式会社 | 温水式洗浄用再付着防止剤、温水式洗浄用洗剤組成物及び温水式洗浄方法 |
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CN105555836B (zh) | 2018-10-02 |
US20160229956A1 (en) | 2016-08-11 |
RU2016114685A (ru) | 2017-10-20 |
JP6639399B2 (ja) | 2020-02-05 |
WO2015036344A1 (de) | 2015-03-19 |
EP3046949A1 (de) | 2016-07-27 |
US10233286B2 (en) | 2019-03-19 |
MX2016003441A (es) | 2016-06-28 |
BR112016005592A2 (pt) | 2017-08-01 |
EP3046949B1 (de) | 2019-06-26 |
ES2746223T3 (es) | 2020-03-05 |
CN105555836A (zh) | 2016-05-04 |
RU2673812C2 (ru) | 2018-11-30 |
BR112016005592B1 (pt) | 2021-08-24 |
KR20160058139A (ko) | 2016-05-24 |
CA2922734A1 (en) | 2015-03-19 |
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