JP2017536437A - 1,3−ジアルコールをベースとするポリエーテルアミン - Google Patents
1,3−ジアルコールをベースとするポリエーテルアミン Download PDFInfo
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- JP2017536437A JP2017536437A JP2017516653A JP2017516653A JP2017536437A JP 2017536437 A JP2017536437 A JP 2017536437A JP 2017516653 A JP2017516653 A JP 2017516653A JP 2017516653 A JP2017516653 A JP 2017516653A JP 2017536437 A JP2017536437 A JP 2017536437A
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- ether amine
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- 239000000203 mixture Substances 0.000 claims abstract description 118
- -1 ether amine Chemical class 0.000 claims abstract description 44
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 36
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 25
- 238000005576 amination reaction Methods 0.000 claims abstract description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 10
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 36
- 150000000185 1,3-diols Chemical class 0.000 claims description 25
- 150000001412 amines Chemical class 0.000 claims description 21
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 19
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 9
- 239000010949 copper Substances 0.000 claims description 9
- 229910052759 nickel Inorganic materials 0.000 claims description 9
- 230000002829 reductive effect Effects 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 8
- 229910017052 cobalt Inorganic materials 0.000 claims description 8
- 239000010941 cobalt Substances 0.000 claims description 8
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 8
- 229920000570 polyether Polymers 0.000 claims description 8
- 230000009467 reduction Effects 0.000 claims description 8
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 claims description 7
- 150000002927 oxygen compounds Chemical class 0.000 claims description 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 6
- 229910052782 aluminium Inorganic materials 0.000 claims description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- 238000007278 cyanoethylation reaction Methods 0.000 claims description 6
- 238000009472 formulation Methods 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 229910052802 copper Inorganic materials 0.000 claims description 5
- 229920000642 polymer Polymers 0.000 claims description 5
- JVZZUPJFERSVRN-UHFFFAOYSA-N 2-methyl-2-propylpropane-1,3-diol Chemical compound CCCC(C)(CO)CO JVZZUPJFERSVRN-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 150000002009 diols Chemical class 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 229910052718 tin Inorganic materials 0.000 claims description 4
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 claims description 3
- 239000011149 active material Substances 0.000 claims description 3
- QUQFTIVBFKLPCL-UHFFFAOYSA-L copper;2-amino-3-[(2-amino-2-carboxylatoethyl)disulfanyl]propanoate Chemical compound [Cu+2].[O-]C(=O)C(N)CSSCC(N)C([O-])=O QUQFTIVBFKLPCL-UHFFFAOYSA-L 0.000 claims description 3
- 239000003822 epoxy resin Substances 0.000 claims description 3
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 3
- 229920000647 polyepoxide Polymers 0.000 claims description 3
- 239000000344 soap Substances 0.000 claims description 3
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 2
- 229920002396 Polyurea Polymers 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 2
- 229920002635 polyurethane Polymers 0.000 claims description 2
- 239000004814 polyurethane Substances 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 239000002453 shampoo Substances 0.000 claims description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 2
- 239000000853 adhesive Substances 0.000 claims 1
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- 229920006345 thermoplastic polyamide Polymers 0.000 claims 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 238000004140 cleaning Methods 0.000 description 58
- 238000005406 washing Methods 0.000 description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 239000003921 oil Substances 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 17
- 239000004744 fabric Substances 0.000 description 17
- 239000003599 detergent Substances 0.000 description 16
- 239000000463 material Substances 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 14
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 239000004094 surface-active agent Substances 0.000 description 12
- 239000000654 additive Substances 0.000 description 11
- 239000003925 fat Substances 0.000 description 9
- 239000002689 soil Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 150000001340 alkali metals Chemical class 0.000 description 7
- 238000004851 dishwashing Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000006722 reduction reaction Methods 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- 238000006268 reductive amination reaction Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 239000012018 catalyst precursor Substances 0.000 description 4
- 239000002131 composite material Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920001515 polyalkylene glycol Polymers 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 229910052570 clay Inorganic materials 0.000 description 3
- 238000007046 ethoxylation reaction Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- VASIZKWUTCETSD-UHFFFAOYSA-N oxomanganese Chemical compound [Mn]=O VASIZKWUTCETSD-UHFFFAOYSA-N 0.000 description 3
- 235000011007 phosphoric acid Nutrition 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 229920002689 polyvinyl acetate Polymers 0.000 description 3
- 239000011118 polyvinyl acetate Substances 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- 239000011135 tin Substances 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- BHEIMYVOVVBWRL-UHFFFAOYSA-N 2-methyl-2-phenylpropane-1,3-diol Chemical compound OCC(C)(CO)C1=CC=CC=C1 BHEIMYVOVVBWRL-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
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- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
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- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
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- 150000004679 hydroxides Chemical class 0.000 description 2
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- 238000004806 packaging method and process Methods 0.000 description 2
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- NJHQOQAEEYIWOB-UHFFFAOYSA-N 2-methyl-2-propan-2-ylpropane-1,3-diol Chemical compound CC(C)C(C)(CO)CO NJHQOQAEEYIWOB-UHFFFAOYSA-N 0.000 description 1
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 1
- JPFNKCYHAFWXPA-UHFFFAOYSA-N 2-pentyl-2-propylpropane-1,3-diol Chemical compound CCCCCC(CO)(CO)CCC JPFNKCYHAFWXPA-UHFFFAOYSA-N 0.000 description 1
- SYURNNNQIFDVCA-UHFFFAOYSA-N 2-propyloxirane Chemical compound CCCC1CO1 SYURNNNQIFDVCA-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
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- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
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- B29C35/00—Heating, cooling or curing, e.g. crosslinking or vulcanising; Apparatus therefor
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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Abstract
Description
R1〜R6の少なくとも1つ及びR7〜R12の少なくとも1つは、Hと異なる基であり、
A1〜A9は、独立して、2〜18個の炭素原子、好ましくは2〜10個の炭素原子、最も好ましくは2〜5個の炭素原子を有する直鎖又は分岐のアルキレンから選択され、
Z1〜Z4は、独立して、OH又はCH2CH2CH2NH2、NH2、NHR’又はNR’R’’から選択され、
アミノ化度は、50%未満であり、
R’及びR’’は、独立して、2個〜6個の炭素原子を有するアルキレンから選択され、
x+yの合計は、約2〜約200の範囲であり、
x≧1、y≧1であり、
x1+y1は、約2〜約200、好ましくは2〜20、最も好ましくは2〜10の範囲であり、
x1≧1、y1≧1である)
のアミンを含むエーテルアミン混合物により達成される。
a)式(III)、
の1,3−ジオール(化合物A)をプロピレンオキシド及び/又はエチレンオキシドと、1:2〜1:10の範囲である1,3−ジオールとC2〜C18−アルキレンオキシドとのモル比で、反応させる工程と、次に以下のいずれか1つの工程、
b1)アルコキシル化1,3−ジオールを、アンモニアでアミノ化させる工程、又は、
b2)アルコキシル化1,3−ジオールを還元的シアノエチル化させる工程と、
を含む方法により得られうる。
置換された1,3−ジオール(式III)は、WO10026030、WO10026066、WO09138387、WO09153193、WO10010075に従って合成される。
R1〜R6の少なくとも1つ及びR7〜R12の少なくとも1つは、Hと異なる基であり、
A1〜A9は、独立して、2〜18個の炭素原子、好ましくは2〜10個の炭素原子、最も好ましくは2〜5個の炭素原子を有する直鎖又は分岐のアルキレンから選択され、
x+yの合計が約2〜約200の範囲にあり、
x≧1、y≧1であり、
x1+y1の合計が、約2〜約200、好ましくは2〜20、最も好ましくは2〜10の範囲にあり、
x1≧1、y1≧1である)
に示される構造をもたらす。
1,3−ジオールのアミノ化は、2つの異なる方法、還元的アミノ化(b1)又は還元的シアノエチル化(b2)により行うことができ、式I及び/又は式II、
R1〜R6の少なくとも1つ及びR7〜R12の少なくとも1つは、Hと異なる基であり、
A1〜A9は、独立して、2〜18個の炭素原子、好ましくは2〜10個の炭素原子、最も好ましくは2〜5個の炭素原子を有する直鎖又は分岐のアルキレンから選択され、
Z1〜Z4は、独立して、OH又はCH2CH2CH2NH2、NH2、NHR’及びNR’R’’から選択され、
アミノ化度は、50%未満であり、
R’及びR’’は、独立して、2個〜6個の炭素原子を有するアルキレンから選択され、
x+yの合計は、約2〜約200の範囲であり、
x≧1、y≧1であり、
x1+y1は、約2〜約200、好ましくは2〜20、最も好ましくは2〜10の範囲であり、
x1≧1、y1≧1である)
を有する新しい構造をもたらす。
式(I)及び/又は式(II)によるポリエーテルアミンは、水素及びニッケル含有触媒の存在下で、アルコキシル化1,3−ジオール混合物(式IV及び/又は式V)とアンモニアとの還元的アミノ化により得られる。好適な触媒は、WO2011/067199A1、WO2011/067200A1及びEP0696572B1に記載されている。好ましい触媒は、担持された銅−、ニッケル−及びコバルト−含有の触媒であり、この触媒の、水素で還元する前の触媒活性物質が、アルミニウム、銅、ニッケル及びコバルトの酸素化合物を、SnOとして計算されるスズの酸素化合物を0.2〜5.0質量%の範囲で含む。他の好ましい触媒は、担持された銅−、ニッケル−及びコバルト−含有の触媒であり、この触媒の、水素で還元する前の触媒活性物質が、アルミニウム、銅、ニッケル、コバルト及びスズの酸素化合物を、それぞれY2O3、La2O3、Ce2O3及びHf2O3として計算されるイットリウム、ランタン、セリウム及び/又はハフニウムの酸素化合物の0.2〜5.0質量%の範囲で含む。別の好ましい触媒は、ジルコニウム、銅、ニッケル触媒であり、その触媒活性組成物が、20〜85質量%の酸素含有ジルコニウム化合物(ZrO2として計算される)、1〜30質量%の銅の酸素含有化合物(CuOとして計算される)、30〜70質量%のニッケルの酸素含有化合物(NiOとして計算される)、0.1〜5質量%のアルミニウム及び/又はマンガンの酸素含有化合物(それぞれAl2O3、MnO2として計算される)を含む。
式(I)及び/又は式(II)によるポリエーテルアミンは、アルコキシル化1,3−ジオール混合物(式IV及び/又は式V)の還元的シアノエチル化により得られる。還元的シアノエチル化は、水素及び触媒での水素化の後、塩基の存在下で、式(I)及び/又は式(II)によるポリエーテルアミンとアクリロニトリルとの反応により行われる。
本発明のエーテルアミン混合物は、パーソナルケア、特にシャンプー及びボディソープの処方物に使用することができる。
洗浄組成物は、十分な量の界面活性剤系を含み、所望の洗浄特性を提供する。ある実施態様において、洗浄組成物は、組成物質量に対して、約1質量%〜約70質量%の界面活性剤系を含む。他の実施態様において、液体洗浄組成物は、組成物質量に対して、約2質量%〜約60質量%の界面活性剤系を含む。さらなる実施態様において、洗浄組成物は、組成物質量に対して、約5質量%〜約30質量%の界面活性剤系を含む。界面活性剤系は、アニオン性界面活性剤、非イオン性界面活性剤、カチオン性界面活性剤、両性イオン界面活性剤、(酸性と塩基性の)両性界面活性剤(amphoteric surfactants)、両性(電解質)界面活性剤(ampholytic surfactants)及びこれらの混合物から選択された洗浄界面活性剤(detersive surfactant)を含んでもよい。当業者は、洗浄界面活性剤が、汚れた材料に対して、洗浄、汚れ除去、又は洗濯のメリットを提供する任意の界面活性剤又は界面活性剤の混合物を含有すると理解するであろう。
また、本発明の洗浄組成物は補助洗浄の添加剤を含んでもよい。好適な補助洗浄の添加剤としては、ビルダー、構造化剤又は増粘剤、粘土汚れ(clay soil)の除去/再付着防止剤、高分子防汚剤(polymeric soil release agents)、高分子分散剤、高分子油脂洗浄剤、酵素、酵素安定系、漂白化合物、漂白剤、漂白活性化剤、漂白触媒、増白剤、染料、色相剤(hueing agents)、転染抑制剤、キレート剤、発泡抑制剤、柔軟剤及び香料を含む。
本発明には、汚れた材料を洗浄する方法が含まれる。当業者に受け入れられるように、本発明の洗浄組成物は、洗濯前処理用途、洗濯洗浄用途、家庭ケア用途における使用に適する。
汚れた食器、食卓用食器、銀製食器又は他の台所用具の機洗浄又は手洗い方法は含まれる。1つの機洗浄方法は、本発明に記載の食器の機洗浄組成物の有効量をそれに溶解又は分散された水溶液によって汚れた食器、食卓用食器、銀製食器又は他の台所用具を処理する工程を含む。食器の機洗浄組成物の有効量は、約3リットル〜約10リットル体積の洗濯液に約8g〜約60gの製品を溶解又は分散することを意味する。
ここに記載の洗浄組成物は、紙、ボール紙(cardboard)、プラスチック材料及び任意の好適な薄板で構成されるものを含む任意の好適な容器中に包装することができる。任意の包装タイプは、ヨーロッパ出願No.94921505.7に記載されている。
また、ここに記載の洗浄組成物は、多区画の洗浄組成物として包装されてもよい。
2リットルのオートクレーブ中で、313.1gの2−ブチル−2−エチル−1,3−プロパンジオール及び3.8gのKOH(50%の水溶液)を混合し、120℃で真空(10ミリバール未満)したで2時間攪拌した。該オートクレーブを、窒素でパージして、140℃まで加熱した。635.6gのプロピレンオキシドを、6時間以内に分けて添加した。反応を完結させるために、混合物を140℃でさらに5時間後反応させた。窒素で反応混合物を揮散し、80℃で真空下に揮発性化合物を除去した。50.9gの水及び8.2gのリン酸(40%の水溶液)を添加し、100℃で0.5時間撹拌し、真空下で2時間脱水することにより、触媒を除去した。濾過後、930.0gの淡黄色オイル(ヒドロキシ価:233mgKOH/g)を得た。
15mLのシリカ(3x3mmのペレット)、その後に70mLの触媒前駆体(WO 2013/072289 A1に従って製造され、1.0〜1.6mmに分裂した、ガマ−Al2O3の上にあるニッケル、コバルト、銅及びスズの酸化物を含む)(74g)を入れ、シリカ(約15mL)で充填した管型反応装置(長さ500mm、直径18mm)中で、(1a)のアミノ化を行った。
牛の脂肪、豚の脂肪及びソーセージの油脂を含む青いニット綿の工業汚れ見本(Technical stain swatches)を、Warwick Equest株式会社から購入し、加熱しないで59分の洗濯サイクルを選択し、75gの液体洗剤組成物LA1(表9)、及びエーテルアミンの添加の後にpHを再調整するためのいくらかの塩酸(1Lの水において、75gのLA1(表2)のpHは、pH=8.3であるべきである)を、1.125gのエーテルアミン添加剤と一緒に、又はそれを用いないで使用して、従来の西欧の洗濯機(Miele Waschmaschine Softronic W 2241)で洗濯した。水の硬度は2.5mM(Ca2+:Mg2+は3:1であった)であった。標準測色測定を用いて、それぞれの汚れの洗濯前後のL*、a*、b*値を得た。L*、a*、b*値で、汚れのレベルを計算した。
ΔE後は、洗濯後の汚れレベルである。
11蛍光増白剤1はTinopal(登録商標)AMSであり、蛍光増白剤2はCiba Specialty Chemicals,Basel,Switzerlandから購入した。
Claims (24)
- エーテルアミン混合物であって、
該エーテルアミン混合物の総質量に基づいて、少なくとも90質量%の、式(I)及び/又は(II)、
R1〜R6の少なくとも1つ及びR7〜R12の少なくとも1つは、Hと異なる基であり、
A1〜A9は、独立して、2〜18個の炭素原子、好ましくは2〜10個の炭素原子、最も好ましくは2〜5個の炭素原子を有する直鎖又は分岐のアルキレンから選択され、
Z1〜Z4は、独立して、OH、CH2CH2CH2NH2、NH2、NHR’又はNR’R’’から選択され、
アミノ化度は、50%未満であり、
R’及びR’’は、独立して、2個〜6個の炭素原子を有するアルキレンから選択され、
x+yの合計は、2〜200の範囲であり、
x≧1、y≧1であり、
x1+y1は、2〜200、好ましくは2〜20、最も好ましくは2〜10の範囲であり、
x1≧1、y1≧1である)
のアミンを含む、エーテルアミン混合物。 - 前記エーテルアミン混合物が、前記エーテルアミン混合物の総質量に基づいて、少なくとも95質量%の式(I)及び/又は(II)のアミンを含む、請求項1に記載のエーテルアミン混合物。
- 式(I)又は式(II)の前記ポリエーテルアミンにおいて、x+yが2〜20の範囲にある、請求項1又は2に記載のエーテルアミン混合物。
- 式(I)又は式(II)の前記ポリエーテルアミンにおいて、x+yが3〜20の範囲にある、請求項1から3のいずれか一項に記載のエーテルアミン混合物。
- 式(I)又は式(II)の前記ポリエーテルアミンにおいて、アミノ化度が、30%から50%未満の範囲にある請求項1から4のいずれか一項に記載のエーテルアミン混合物。
- 式(I)又は式(II)の前記ポリエーテルアミンにおいて、A1〜A9が、独立して、エチレン、プロピレン又はブチレン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エーテルアミン混合物。
- 式(I)又は式(II)の前記ポリエーテルアミンにおいて、A1〜A9のそれぞれがプロピレンである、請求項1から4のいずれか一項に記載のエーテルアミン混合物。
- 式(I)又は式(II)の前記ポリエーテルアミンにおいて、R1、R2、R5、R6、R7、R8、R11及びR12がHであり、R3、R4、R9及びR10が独立してC1〜16アルキル又はアリールから選択される、請求項1から6のいずれか一項に記載のエーテルアミン混合物。
- 式(I)又は式(II)の前記ポリエーテルアミンにおいて、R1、R2、R5、R6、R7、R8、R11及びR12がHであり、R3、R4、R9及びR10が独立してブチル基、エチル基、メチル基、プロピル基又はフェニル基から選択される、請求項1から6のいずれか一項に記載のエーテルアミン混合物。
- 式(I)又は式(II)の前記ポリエーテルアミンにおいて、R3及びR9がそれぞれエチル基であり、R1、R2、R5、R6、R7、R8、R11及びR12がそれぞれHであり、R4及びR10がそれぞれブチル基である、請求項1から6のいずれか一項に記載のエーテルアミン混合物。
- 式(I)又は式(II)の前記ポリエーテルアミンが、約290〜約1000グラム/モルの質量平均分子量を有する、請求項1から9のいずれか一項に記載のエーテルアミン混合物。
- 式(I)又は式(II)の前記ポリエーテルアミンが酸と反応した、請求項1から9のいずれか一項に記載のエーテルアミン混合物。
- 式(I)及び/又は式(II)のエーテルアミンを、当該エーテルアミン混合物の総質量に基づいて、少なくとも90質量%含むエーテルアミン混合物の製造方法であって、
以下の工程:
a)式(III)
R1〜R6から選択される少なくとも1つの基は、Hと異なる基である)
の1,3−ジオールとC2〜C18アルキレンオキシドとを、1,3−ジオールとC2〜C18アルキレンオキシドとのモル比を1:2〜1:10の範囲にして、反応させる工程と、次に以下のいずれか1つの工程、
b1)アルコキシル化1,3−ジオールを、アンモニアでアミノ化させる工程、又は、
b2)アルコキシル化1,3−ジオールを還元的シアノエチル化させる工程と、
を含む、方法。 - 1,3−ジオールとC2〜C18アルキレンオキシドとの前記モル比が、1:3〜1:8の範囲にある、請求項12に記載の方法。
- 1,3−ジオールとC2〜C18アルキレンオキシドとの前記モル比が、1:4〜1:6の範囲にある、請求項12又は13に記載の方法。
- 前記C2〜C18アルキレンオキシドが、エチレンオキシド、プロピレンオキシド、ブチレンオキシド又はこれらの混合物からなる群から選択される、請求項12から14のいずれか一項に記載の方法。
- 前記C2〜C18アルキレンオキシドがプロピレンオキシドである、請求項12から14のいずれか一項に記載の方法。
- 式(III)の前記1,3−ジオールが、2−ブチル−2−エチル−1,3−プロパンジオール、2−メチル−2−プロピル−1,3−プロパンジオール、2−メチル−2−フェニル−1,3−プロパンジオール、2,2−ジメチル−1,3−プロパンジオール、2−エチル−1,3−ヘンキサンジオールからなる群から選択される、請求項12から16のいずれか一項に記載の方法。
- 前記アミノ化工程が、銅−、ニッケル−又はコバルト−含有触媒の存在下で行われる、請求項12から17のいずれか一項に記載の方法。
- 水素で還元する前の、前記触媒の触媒活性材料が、アルミニウム、銅、ニッケル及びコバルトの酸素化合物を含み、SnOとして計算されるスズの酸素化合物を0.2〜5.0質量%の範囲で含んでいる、請求項18に記載の方法。
- 請求項1〜11に記載のエーテルアミン混合物を、パーソナルケアに使用する方法。
- 請求項1〜11に記載のエーテルアミン混合物を、シャンプー製剤及びボディソープ製剤に使用する方法。
- 請求項1〜11に記載のエーテルアミン混合物を、エポキシ樹脂の硬化剤に又はポリマー製造における反応剤として使用する方法。
- 請求項1〜11に記載のエーテルアミン混合物を、ポリウレタン、ポリ尿素に、及び熱可塑性ポリアミド接着剤として使用する方法。
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