JPH0753874B2 - パーム核油脂肪酸アルキルエステルの安定化方法 - Google Patents

パーム核油脂肪酸アルキルエステルの安定化方法

Info

Publication number: JPH0753874B2
Authority: JP; Japan
Prior art keywords: fatty acid; palm kernel; kernel oil; oil fatty; methyl ester
Prior art date: 1985-01-14
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

JP61006135A

Other languages

English (en)

Japanese (ja)

Other versions

JPS61163999A (ja

Inventor

アルフレート・シユトルーフエ

リヒヤルト・シエーフ

ホルスト・バウマン

ハルトビツヒ・シユツト

ハラルト・バリス

Original Assignee

ヘンケル・コマンデイツトゲゼルシヤフト・アウフ・アクチエン

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1985-01-14

Filing date

1986-01-14

Publication date

1995-06-07

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=6259752&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=JPH0753874(B2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1986-01-14 Application filed by ヘンケル・コマンデイツトゲゼルシヤフト・アウフ・アクチエン filed Critical ヘンケル・コマンデイツトゲゼルシヤフト・アウフ・アクチエン

1986-07-24 Publication of JPS61163999A publication Critical patent/JPS61163999A/ja

1995-06-07 Publication of JPH0753874B2 publication Critical patent/JPH0753874B2/ja

2010-06-07 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000003346 palm kernel oil Substances 0.000 title claims description 48
235000019865 palm kernel oil Nutrition 0.000 title claims description 48
235000014113 dietary fatty acids Nutrition 0.000 title claims description 37
229930195729 fatty acid Natural products 0.000 title claims description 37
239000000194 fatty acid Substances 0.000 title claims description 37
238000000034 method Methods 0.000 title description 7
230000000087 stabilizing effect Effects 0.000 title description 4
239000000203 mixture Substances 0.000 claims description 22
150000004665 fatty acids Chemical class 0.000 claims description 20
239000003381 stabilizer Substances 0.000 claims description 13
150000004702 methyl esters Chemical class 0.000 claims description 6
125000005907 alkyl ester group Chemical group 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
125000004492 methyl ester group Chemical group 0.000 claims 1
235000019387 fatty acid methyl ester Nutrition 0.000 description 26
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
239000007795 chemical reaction product Substances 0.000 description 13
235000019482 Palm oil Nutrition 0.000 description 12
239000002540 palm oil Substances 0.000 description 12
150000002148 esters Chemical class 0.000 description 10
OKLNGCVEHOKJIY-UHFFFAOYSA-N 3-butyl-4-methylphenol Chemical compound CCCCC1=CC(O)=CC=C1C OKLNGCVEHOKJIY-UHFFFAOYSA-N 0.000 description 8
239000007858 starting material Substances 0.000 description 8
238000003860 storage Methods 0.000 description 8
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000003963 antioxidant agent Substances 0.000 description 6
235000006708 antioxidants Nutrition 0.000 description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
239000003240 coconut oil Substances 0.000 description 6
235000019864 coconut oil Nutrition 0.000 description 6
-1 fatty acid esters Chemical class 0.000 description 6
229910052760 oxygen Inorganic materials 0.000 description 6
239000001301 oxygen Substances 0.000 description 6
238000007127 saponification reaction Methods 0.000 description 6
239000000243 solution Substances 0.000 description 6
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
238000010521 absorption reaction Methods 0.000 description 5
239000013065 commercial product Substances 0.000 description 5
229910052740 iodine Inorganic materials 0.000 description 5
239000011630 iodine Substances 0.000 description 5
239000003921 oil Substances 0.000 description 5
235000019198 oils Nutrition 0.000 description 5
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000000126 substance Substances 0.000 description 4
GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 4
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 3
239000004255 Butylated hydroxyanisole Substances 0.000 description 3
239000002253 acid Substances 0.000 description 3
235000019282 butylated hydroxyanisole Nutrition 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
238000004821 distillation Methods 0.000 description 3
239000003925 fat Substances 0.000 description 3
235000019197 fats Nutrition 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
150000002978 peroxides Chemical class 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
238000012545 processing Methods 0.000 description 3
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 3
235000019345 sodium thiosulphate Nutrition 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
230000032683 aging Effects 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
235000010323 ascorbic acid Nutrition 0.000 description 2
239000011668 ascorbic acid Substances 0.000 description 2
229960005070 ascorbic acid Drugs 0.000 description 2
CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 2
229940043253 butylated hydroxyanisole Drugs 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
230000032050 esterification Effects 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
235000011187 glycerol Nutrition 0.000 description 2
230000001771 impaired effect Effects 0.000 description 2
230000007774 longterm Effects 0.000 description 2
239000000463 material Substances 0.000 description 2
230000001590 oxidative effect Effects 0.000 description 2
239000000047 product Substances 0.000 description 2
235000010388 propyl gallate Nutrition 0.000 description 2
238000010992 reflux Methods 0.000 description 2
235000010384 tocopherol Nutrition 0.000 description 2
239000011732 tocopherol Substances 0.000 description 2
229930003799 tocopherol Natural products 0.000 description 2
229960001295 tocopherol Drugs 0.000 description 2
238000005809 transesterification reaction Methods 0.000 description 2
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
OTJFQRMIRKXXRS-UHFFFAOYSA-N (hydroxymethylamino)methanol Chemical compound OCNCO OTJFQRMIRKXXRS-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 description 1
235000000072 L-ascorbyl-6-palmitate Nutrition 0.000 description 1
239000011786 L-ascorbyl-6-palmitate Substances 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 1
239000002250 absorbent Substances 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229940087168 alpha tocopherol Drugs 0.000 description 1
229940064063 alpha tocotrienol Drugs 0.000 description 1
RZFHLOLGZPDCHJ-DLQZEEBKSA-N alpha-Tocotrienol Natural products Oc1c(C)c(C)c2O[C@@](CC/C=C(/CC/C=C(\CC/C=C(\C)/C)/C)\C)(C)CCc2c1C RZFHLOLGZPDCHJ-DLQZEEBKSA-N 0.000 description 1
238000005576 amination reaction Methods 0.000 description 1
230000003078 antioxidant effect Effects 0.000 description 1
238000006701 autoxidation reaction Methods 0.000 description 1
UDSAIICHUKSCKT-UHFFFAOYSA-N bromophenol blue Chemical compound C1=C(Br)C(O)=C(Br)C=C1C1(C=2C=C(Br)C(O)=C(Br)C=2)C2=CC=CC=C2S(=O)(=O)O1 UDSAIICHUKSCKT-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000012993 chemical processing Methods 0.000 description 1
229960004106 citric acid Drugs 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
239000008139 complexing agent Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
235000021588 free fatty acids Nutrition 0.000 description 1
235000010382 gamma-tocopherol Nutrition 0.000 description 1
WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000006698 induction Effects 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
230000004130 lipolysis Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
229940097411 palm acid Drugs 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000000473 propyl gallate Substances 0.000 description 1
229940075579 propyl gallate Drugs 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000000344 soap Substances 0.000 description 1
239000008149 soap solution Substances 0.000 description 1
HSFQBFMEWSTNOW-UHFFFAOYSA-N sodium;carbanide Chemical group [CH3-].[Na+] HSFQBFMEWSTNOW-UHFFFAOYSA-N 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
239000013589 supplement Substances 0.000 description 1
229960000984 tocofersolan Drugs 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
238000005406 washing Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
RZFHLOLGZPDCHJ-XZXLULOTSA-N α-Tocotrienol Chemical compound OC1=C(C)C(C)=C2O[C@@](CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1C RZFHLOLGZPDCHJ-XZXLULOTSA-N 0.000 description 1
235000004835 α-tocopherol Nutrition 0.000 description 1
239000002076 α-tocopherol Substances 0.000 description 1
239000011730 α-tocotrienol Substances 0.000 description 1
235000019145 α-tocotrienol Nutrition 0.000 description 1
239000002478 γ-tocopherol Substances 0.000 description 1
QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B5/00—Preserving by using additives, e.g. anti-oxidants
- C11B5/0021—Preserving by using additives, e.g. anti-oxidants containing oxygen
- C11B5/0035—Phenols; Their halogenated and aminated derivates, their salts, their esters with carboxylic acids

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Emergency Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Oil, Petroleum & Natural Gas (AREA)
Wood Science & Technology (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Fats And Perfumes (AREA)
Cosmetics (AREA)

JP61006135A 1985-01-14 1986-01-14 パーム核油脂肪酸アルキルエステルの安定化方法 Expired - Lifetime JPH0753874B2 (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE3500938.1		1985-01-14
DE19853500938 DE3500938A1 (de)	1985-01-14	1985-01-14	Stabilisierung von palmkernoel und palmkernfettsaeurealkylestern fuer deren verarbeitung zu farbneutralen reaktionsfolgeprodukten

Publications (2)

Publication Number	Publication Date
JPS61163999A JPS61163999A (ja)	1986-07-24
JPH0753874B2 true JPH0753874B2 (ja)	1995-06-07

Family

ID=6259752

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP61006135A Expired - Lifetime JPH0753874B2 (ja)	1985-01-14	1986-01-14	パーム核油脂肪酸アルキルエステルの安定化方法

Country Status (6)

Country	Link
EP (1)	EP0189049B2 (fr)
JP (1)	JPH0753874B2 (fr)
BR (1)	BR8600103A (fr)
DE (2)	DE3500938A1 (fr)
GB (1)	GB2169611B (fr)
MY (1)	MY102435A (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IE980887A1 (en) *	1998-10-27	2000-05-03	Diarmaid Joseph Long	Anti-oxidant formulations
DE102005015474A1 (de)	2005-04-04	2006-10-05	Degussa Ag	Verfahren zur Erhöhung der Oxidationsstabilität von Biodiesel
WO2009108747A1 (fr) *	2008-02-27	2009-09-03	Wayne State University	Effet d’antioxydants naturels et synthétiques sur la stabilité à l’oxydation de biodiésel
US20120233912A1 (en)	2011-03-18	2012-09-20	Otkrytoe Aktsionernoe Obschestvo "Sterlitamaxky Neftekhimichesky Zavod"	Antioxidant additive composition, a solution thereof, and a method for improving the storage stability of biodiesel fuel (variants)
EA201490985A1 (ru) *	2011-11-16	2014-10-30	Текникс Индастриз Лимитед	Разжижающие битум добавки
RU2476585C1 (ru)	2012-03-07	2013-02-27	Открытое Акционерное Общество "Стерлитамакский Нефтехимический Завод"	Композиция антиокислительной присадки, ее раствор и способ повышения стабильности биодизельного топлива при хранении (варианты)
US11535774B2 (en)	2021-03-08	2022-12-27	Technix EnviroCutter IP Limited	Bitumen cutback compositions and methods of use thereof

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB754388A (en) *	1954-04-02	1956-08-08	Alfred William Brickman	Improvements in the inhibition of oxidation of fats or fatty oils
JPS5373206A (en) *	1976-12-10	1978-06-29	Riken Vitamin Co Ltd	Antioxidant composition for fat and oil
JPS5554400A (en) *	1978-10-17	1980-04-21	Nisshin Oil Mills Ltd	Manufacture of high antiioxidability fat and oil
JPS5944344B2 (ja) *	1978-11-17	1984-10-29	田辺製薬株式会社	抗酸化剤
JPS6042495A (ja) *	1983-08-17	1985-03-06	日清製油株式会社	油脂脱臭留出物のメチルエステル化法

1985
- 1985-01-14 DE DE19853500938 patent/DE3500938A1/de active Granted
1986
- 1986-01-02 GB GB8600027A patent/GB2169611B/en not_active Expired
- 1986-01-07 EP EP86100134A patent/EP0189049B2/fr not_active Expired - Lifetime
- 1986-01-07 DE DE8686100134T patent/DE3673027D1/de not_active Expired - Lifetime
- 1986-01-13 BR BR8600103A patent/BR8600103A/pt unknown
- 1986-01-14 JP JP61006135A patent/JPH0753874B2/ja not_active Expired - Lifetime
1987
- 1987-04-18 MY MYPI87000504A patent/MY102435A/en unknown

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
油化学第２８巻第１０号（１９７９），Ｐ．７４７〜７５９

Also Published As

Publication number	Publication date
JPS61163999A (ja)	1986-07-24
EP0189049B1 (fr)	1990-08-01
GB8600027D0 (en)	1986-02-12
MY102435A (en)	1992-06-30
DE3673027D1 (de)	1990-09-06
GB2169611B (en)	1989-09-13
GB2169611A (en)	1986-07-16
EP0189049A1 (fr)	1986-07-30
BR8600103A (pt)	1986-09-23
DE3500938C2 (fr)	1993-06-24
EP0189049B2 (fr)	1993-12-15
DE3500938A1 (de)	1986-07-17

Legal Events

Date	Code	Title	Description
2004-06-08	R250	Receipt of annual fees	Free format text: JAPANESE INTERMEDIATE CODE: R250
2004-12-09	S111	Request for change of ownership or part of ownership	Free format text: JAPANESE INTERMEDIATE CODE: R313113 Free format text: JAPANESE INTERMEDIATE CODE: R313111
2004-12-16	R350	Written notification of registration of transfer	Free format text: JAPANESE INTERMEDIATE CODE: R350
2005-06-07	R250	Receipt of annual fees	Free format text: JAPANESE INTERMEDIATE CODE: R250
2006-01-14	EXPY	Cancellation because of completion of term

Publication	Publication Date	Title
JP3005226B2 (ja)	2000-01-31	抗酸化剤混合物の製造法
CN1117845C (zh)	2003-08-13	具有优良的温和性、起泡和抗变色的透明无色皂条
JP5159321B2 (ja)	2013-03-06	クリプテコディニウム属からの抗酸化抽出物の製造および使用
CA1167467A (fr)	1984-05-15	Preparation d'esters d'acides a-sulfo-gras, legerement colores et actifs au lavage
DE3419796A1 (de)	1984-11-29	Zusammensetzungen, enthaltend ungesaettigte fettsaeuren und verfahren zu deren stabilisierung
JPH0753874B2 (ja)	1995-06-07	パーム核油脂肪酸アルキルエステルの安定化方法
JPH0657247A (ja)	1994-03-01	酸化防止剤組成物
Chisholm et al.	1957	An oxygenated fatty acid from the seed oil of Hibiscus esculentus
Kiritsakis et al.	1983	Effect of selected antioxidants on the stability of virgin olive oil
JP6817313B2 (ja)	2021-01-20	育児用調製粉乳に用いるための油脂組成物
US5948926A (en)	1999-09-07	Method for inhibiting oxidation of oils and fats or fatty acids
Cowan et al.	1962	Citric acid: Inactivating agent for metals or acidic synergist in edible fats?
DE69809743T2 (de)	2003-09-04	An omega-3 ungesättigten fettsäuren angereicherte wachsester, ihre herstellung und verwendung
US2441547A (en)	1948-05-11	Hydroxylamine stabilized fatty materials
US2123863A (en)	1938-07-12	Food composition and process of inhibiting oxygenation thereof
Buxton	1947	Tocopherols as antioxidants for vitamin A in fish liver oils
DE2515112A1 (de)	1975-11-13	Praeparate
US2813112A (en)	1957-11-12	Soap composition
US1913367A (en)	1933-06-13	Preservation of oils, fats, fatty oils, fatty esters, fatty acids, fatty acid salts,and related compounds
NO133920B (fr)	1976-04-12
JPH09111297A (ja)	1997-04-28	透明固形洗浄剤組成物
Golumbic et al.	1946	Flavor reversion in soybean oil: III. The preparation and flavor characteristics of a simulated soybean oil
US2324347A (en)	1943-07-13	Preservation of perfumes
DE19736737C2 (de)	1999-11-11	Verfahren zu Herstellung von oxidationsstabilen Oleinen und ihre Verwendung zur Herstellung von Wasch- und Reinigungsmitteln, kosmetischen und/oder pharmazeutischen Formulierungen, ungesättigten Fettalkoholen oder Estern
Potter et al.	1950	Factors involved in the spectrophotometric analysis of fats