RU2020105707A - Алкоксилированные сложные эфирамины и их соли - Google Patents
Алкоксилированные сложные эфирамины и их соли Download PDFInfo
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- RU2020105707A RU2020105707A RU2020105707A RU2020105707A RU2020105707A RU 2020105707 A RU2020105707 A RU 2020105707A RU 2020105707 A RU2020105707 A RU 2020105707A RU 2020105707 A RU2020105707 A RU 2020105707A RU 2020105707 A RU2020105707 A RU 2020105707A
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- 150000003839 salts Chemical class 0.000 title claims 13
- 125000000217 alkyl group Chemical group 0.000 claims 12
- -1 ethyleneoxy group Chemical group 0.000 claims 11
- 150000001875 compounds Chemical class 0.000 claims 7
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- 239000004471 Glycine Substances 0.000 claims 3
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 3
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 3
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 3
- 239000004472 Lysine Substances 0.000 claims 3
- 235000004279 alanine Nutrition 0.000 claims 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims 2
- 239000004475 Arginine Substances 0.000 claims 2
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims 2
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims 2
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims 2
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 2
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims 2
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims 2
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims 2
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims 2
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims 2
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 2
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims 2
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims 2
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims 2
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 2
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims 2
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims 2
- 239000004473 Threonine Substances 0.000 claims 2
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims 2
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 2
- 235000009697 arginine Nutrition 0.000 claims 2
- 235000009582 asparagine Nutrition 0.000 claims 2
- 229960001230 asparagine Drugs 0.000 claims 2
- 235000003704 aspartic acid Nutrition 0.000 claims 2
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims 2
- 235000018417 cysteine Nutrition 0.000 claims 2
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims 2
- 235000004554 glutamine Nutrition 0.000 claims 2
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims 2
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims 2
- 229960000310 isoleucine Drugs 0.000 claims 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 2
- 229930182817 methionine Natural products 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims 2
- 230000005588 protonation Effects 0.000 claims 2
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims 2
- 239000004474 valine Substances 0.000 claims 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
- 229920002396 Polyurea Polymers 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 239000000853 adhesive Substances 0.000 claims 1
- 230000001070 adhesive effect Effects 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000003822 epoxy resin Substances 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 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 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000004310 lactic acid Substances 0.000 claims 1
- 235000014655 lactic acid Nutrition 0.000 claims 1
- 229940098779 methanesulfonic acid Drugs 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 229920000647 polyepoxide Polymers 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- 229920002635 polyurethane Polymers 0.000 claims 1
- 239000004814 polyurethane Substances 0.000 claims 1
- 239000002453 shampoo Substances 0.000 claims 1
- 229920006345 thermoplastic polyamide Polymers 0.000 claims 1
Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
- C08G65/2609—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aliphatic hydroxyl groups
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- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
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- A—HUMAN NECESSITIES
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- A61Q19/10—Washing or bathing preparations
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- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/08—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to hydrogen atoms
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- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
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- C07C309/01—Sulfonic acids
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- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
- Cosmetics (AREA)
- Adhesives Or Adhesive Processes (AREA)
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Claims (37)
1. Сложный эфирамин формулы (I) или его соль,
где независимо друг от друга
t представляет собой целое число от 1 до 100;
A1 независимо для каждой повторяющейся единицы t выбрана из перечня, состоящего из этиленоксигруппы, 1,2-пропиленоксигруппы, 1,2-бутиленоксигруппы, 2,3-бутиленоксигруппы, изобутиленоксигруппы, пентиле-ноксигруппы, гексиленоксигруппы, стирилоксигруппы, деценилоксигруппы, до-деценилоксигруппы, тетрадеценилоксигруппы и гексадеканилоксигруппы, где когда t равно 1, атом кислорода группы A1 связан с группой В, и следующая группа Ai всегда связана через атом кислорода с предшествующей группой A1;
B1 независимо друг от друга выбраны из группы, состоящей из связи, линейных C1 - С12 алкандииловых групп и разветвленных C1 - С12 алкандииловых групп;
R4, R8, и R12 выбраны из группы, состоящей из Н, линейного алкила, разветвленного алкила и циклоалкила;
при условии, что Z1 выбрана из группы, состоящей из аланина, аргинина, аспарагина, аспарагиновой кислоты, цистеина, глютамина, глицина, гистидина, изолейцина, лейцина, лизина, метионина, фенилаланина, пролина, серина, треонина, триптофана, тирозина, валина и соединения формулы (II), где указанное соединение формулы (II) соединяется с соединением формулы (I) через связь, обозначенную с помощью *, при условии, что по меньшей мере одна группа R4, R8, и/или R12 содержит по меньшей мере 7 или более атомов углерода;
(Формула II),
где независимо друг от друга
w представляет собой целое число от 0 до 12;
R13 и R14 независимо для каждой повторяющейся единицы w выбраны из группы, состоящей из Н, линейного алкила, разветвленного алкила и циклоалкила;
R15, R16, R17, и R18 выбраны из группы, состоящей из Н, линейного алкила, разветвленного алкила и циклоалкила.
2. Соль сложного эфирамина по п. 1, где соль образована посредством по меньшей мере частичного протонирования аминной группы кислотой, представляющей собой протонную органическую или неорганическую кислоту.
3. Соль сложного эфирамина по любому из пп. 1 или 2, где соль образована посредством по меньшей мере частичного протонирования аминной группы кислотой, выбранной из группы, содержащей метансульфоновую кислоту, соляную кислоту, бромистоводородную кислоту, серную кислоту, фосфорную кислоту, лимонную кислоту и молочную кислоту.
4. Сложный эфирамин или его соль по любому из предшествующих пунктов, где A1 независимо для каждой повторяющейся единицы t выбрана из перечня, состоящего из этиле ноксигруппы, 1,2-пропиленоксигруппы и 1,2-бутиленоксигруппы.
5. Сложный эфирамин или его соль по любому из предшествующих пунктов, где Z1 выбрана из группы, состоящей из аланина, глицина, лизина и соединения формулы (II), где w представляет собой целое число в интервале от 1 до 4, и где соединение формулы (II) соединяется с соединением формулы (I) через связь, обозначенную с помощью *, при условии, что по меньшей мере одна группа R4, R8, и/или R12 содержит по меньшей мере 7 или более атомов углерода.
6. Способ получения сложного эфирамина или его соли по п. 1, включающий стадии
а) реакции спирта формулы (III)
Формула (III)
где независимо друг от друга
В1 выбрана из группы, состоящей из связи, линейных С1 - С12 алкандииловых групп и разветвленных C1 - С12 алкандииловых групп;
R4, R8, и R12 выбраны из группы, состоящей из Н, линейного алкила, разветвленного алкила и циклоалкила;
с одним или более С2 - С16 алкиленоксидами, с последующей
b) по меньшей мере частичной эстерификацией алкоксилированного спирта с по меньшей мере одним соединением, выбранным из группы, состоящей из аланина, аргинина, аспарагина, аспарагиновой кислоты, цистеина, глютамина, глицина, гистидина, изолейцина, лейцина, лизина, метионина, фенилаланина, пролина, се-рина, треонина, триптофана, тирозина, валина, кислот формулы (IV) и их солей;
(Формула IV),
где w представляет собой целое число от 0 до 12,
R13 и R14 независимо для каждой повторяющейся единицы w выбраны из группы, состоящей из Н, линейного алкила, разветвленного алкила и циклоалкила;
R15, R16, R17, и R17 выбраны из группы, состоящей из Н, линейного алкила, разветвленного алкила и циклоалкила.
7. Способ по п. 6, где молярное соотношение спирта формулы (III) и С2 - С12 ал-киленоксида в общем находится в интервале от 1:1 до 1:400.
8. Способ по п. 6 или 7, где молярное соотношение кислотных и гидроксильных групп алкоксилированного спирта находится в интервале от 0.1:1 до 1:1.
9. Применение сложного эфирамина или его соли по пп. 1-5 для личной гигиены в качестве отверждающего средства для эпоксидных смол, в качестве реагента для получения полимеров, в полиуретанах, полимочевинах или в качестве термопластичных полиамидных адгезивов.
10. Применение сложного эфирамина или его соли по п. 9 в составах шампуня или моющего средства для тела.
11. Композиция для личной гигиены, содержащая сложный эфирамин или его соль по любому из пп. 1-6.
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| MX2022008436A (es) * | 2020-01-29 | 2022-08-02 | Procter & Gamble | Una composicion de limpieza. |
| MX2023000161A (es) | 2020-07-03 | 2023-02-22 | Basf Se | Esteraminas sulfatadas. |
| EP3933017A1 (en) | 2020-07-03 | 2022-01-05 | The Procter & Gamble Company | Fabric and home care product comprising a sulfatized esteramine |
| MX2023000568A (es) * | 2020-07-13 | 2023-02-13 | Advansix Resins & Chemicals Llc | Tensioactivos de aminoacidos ramificados para la produccion de gas y petroleo. |
| EP4019614A1 (en) | 2020-12-28 | 2022-06-29 | The Procter & Gamble Company | Cleaning product |
| EP4019615A1 (en) | 2020-12-28 | 2022-06-29 | The Procter & Gamble Company | Liquid hand dishwashing cleaning composition |
| WO2024042005A1 (en) | 2022-08-22 | 2024-02-29 | Basf Se | Process for producing sulfatized esteramines |
| EP4386074A1 (en) | 2022-12-16 | 2024-06-19 | The Procter & Gamble Company | Fabric and home care composition |
| DE102023135175A1 (de) | 2022-12-16 | 2024-06-27 | Basf Se | Verfahren zur Herstellung von Aminosäureestern und organischen Sulfonsäuresalzen sowie Aminosäureestern und deren Salzen |
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| JPH0273803A (ja) * | 1988-09-09 | 1990-03-13 | Lion Corp | ポリマーラテックス |
| US5624906A (en) * | 1994-12-08 | 1997-04-29 | Lever Brothers Company, Division Of Conopco, Inc. | Oral hygiene compositions comprising heteroatom containing alkyl aldonamide compounds |
| IN190971B (ru) | 1999-04-19 | 2003-09-06 | Council Scient Ind Res | |
| JP2003064282A (ja) | 2001-08-29 | 2003-03-05 | Mitsubishi Chemicals Corp | 半導体超微粒子 |
| DE60231428D1 (de) | 2001-12-21 | 2009-04-16 | 3M Innovative Properties Co | Medizinische aerosolzusammensetzungen mit einem funktionalisierten polyethylenglykol-hilfsstoff |
| JP4593134B2 (ja) | 2004-03-17 | 2010-12-08 | 株式会社リコー | 可逆性熱記録用インク、インクカートリッジ、及びインク記録物、並びに、画像記録方法及び画像記録装置 |
| DE102005054037A1 (de) | 2005-11-12 | 2007-05-16 | Clariant Produkte Deutschland | Verwendung von Pyroglutaminsäureestern als Gashydratinhibitoren mit verbesserter biologischer Abbaubarkeit |
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| JP7341978B2 (ja) | 2023-09-11 |
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| CN117024291A (zh) | 2023-11-10 |
| WO2019007750A1 (en) | 2019-01-10 |
| CN110832004A (zh) | 2020-02-21 |
| RU2020105707A3 (ru) | 2021-10-22 |
| US20200140374A1 (en) | 2020-05-07 |
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