NZ619374B2 - Palm olein oil composition - Google Patents
Palm olein oil composition Download PDFInfo
- Publication number
- NZ619374B2 NZ619374B2 NZ619374A NZ61937412A NZ619374B2 NZ 619374 B2 NZ619374 B2 NZ 619374B2 NZ 619374 A NZ619374 A NZ 619374A NZ 61937412 A NZ61937412 A NZ 61937412A NZ 619374 B2 NZ619374 B2 NZ 619374B2
- Authority
- NZ
- New Zealand
- Prior art keywords
- palm olein
- oil
- sts
- ester
- composition according
- Prior art date
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- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 title claims abstract description 272
- 239000000203 mixture Substances 0.000 title claims abstract description 200
- IJCWFDPJFXGQBN-BIFNRIDTSA-N Sorbitan tristearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)[C@H]1OC[C@@H](O)[C@@H]1OC(=O)CCCCCCCCCCCCCCCCC IJCWFDPJFXGQBN-BIFNRIDTSA-N 0.000 claims abstract description 238
- 235000011078 sorbitan tristearate Nutrition 0.000 claims abstract description 237
- 239000001589 sorbitan tristearate Substances 0.000 claims abstract description 237
- 229960004129 sorbitan tristearate Drugs 0.000 claims abstract description 237
- 150000002148 esters Chemical class 0.000 claims abstract description 123
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 104
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 103
- 239000000194 fatty acid Substances 0.000 claims abstract description 103
- 238000002425 crystallisation Methods 0.000 claims abstract description 95
- 230000005712 crystallization Effects 0.000 claims abstract description 95
- 229940080352 Sodium Stearoyl Lactylate Drugs 0.000 claims abstract description 72
- ODFAPIRLUPAQCQ-UHFFFAOYSA-M Sodium stearoyl lactylate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC(=O)OC(C)C(=O)OC(C)C([O-])=O ODFAPIRLUPAQCQ-UHFFFAOYSA-M 0.000 claims abstract description 72
- 150000003839 salts Chemical class 0.000 claims abstract description 72
- 239000011780 sodium chloride Substances 0.000 claims abstract description 72
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims abstract description 50
- 235000014655 lactic acid Nutrition 0.000 claims abstract description 50
- 239000004310 lactic acid Substances 0.000 claims abstract description 49
- 150000003903 lactic acid esters Chemical class 0.000 claims abstract description 35
- 238000003860 storage Methods 0.000 claims abstract description 25
- 229920000223 polyglycerol Polymers 0.000 claims abstract description 13
- 239000003921 oil Substances 0.000 claims description 139
- 235000019198 oils Nutrition 0.000 claims description 139
- 150000003626 triacylglycerols Chemical class 0.000 claims description 40
- 230000002401 inhibitory effect Effects 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 33
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 32
- IPCSVZSSVZVIGE-UHFFFAOYSA-N Palmitic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 22
- 159000000000 sodium salts Chemical class 0.000 claims description 22
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 20
- QIQXTHQIDYTFRH-UHFFFAOYSA-N Stearic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 18
- 159000000007 calcium salts Chemical class 0.000 claims description 15
- DPUOLQHDNGRHBS-KTKRTIGZSA-N Erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 claims description 10
- 235000021355 Stearic acid Nutrition 0.000 claims description 9
- 159000000001 potassium salts Chemical class 0.000 claims description 9
- 239000008117 stearic acid Substances 0.000 claims description 9
- 239000005642 Oleic acid Substances 0.000 claims description 8
- 235000021314 Palmitic acid Nutrition 0.000 claims description 8
- 150000004671 saturated fatty acids Chemical class 0.000 claims description 7
- 235000019486 Sunflower oil Nutrition 0.000 claims description 6
- 239000000828 canola oil Substances 0.000 claims description 6
- 235000019519 canola oil Nutrition 0.000 claims description 6
- 239000002600 sunflower oil Substances 0.000 claims description 6
- 238000010899 nucleation Methods 0.000 claims description 5
- 235000019483 Peanut oil Nutrition 0.000 claims description 4
- 235000019774 Rice Bran oil Nutrition 0.000 claims description 4
- 239000000312 peanut oil Substances 0.000 claims description 4
- 239000008165 rice bran oil Substances 0.000 claims description 4
- 235000010469 Glycine max Nutrition 0.000 claims description 3
- 235000019485 Safflower oil Nutrition 0.000 claims description 2
- 239000002285 corn oil Substances 0.000 claims description 2
- 235000005687 corn oil Nutrition 0.000 claims description 2
- 235000012343 cottonseed oil Nutrition 0.000 claims description 2
- 239000002385 cottonseed oil Substances 0.000 claims description 2
- 239000010658 moringa oil Substances 0.000 claims description 2
- 239000004006 olive oil Substances 0.000 claims description 2
- 235000008390 olive oil Nutrition 0.000 claims description 2
- 235000005713 safflower oil Nutrition 0.000 claims description 2
- 239000003813 safflower oil Substances 0.000 claims description 2
- 240000006240 Linum usitatissimum Species 0.000 claims 1
- 235000004431 Linum usitatissimum Nutrition 0.000 claims 1
- WYMSBXTXOHUIGT-UHFFFAOYSA-N Paraoxon Chemical compound CCOP(=O)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 WYMSBXTXOHUIGT-UHFFFAOYSA-N 0.000 claims 1
- 235000004426 flaxseed Nutrition 0.000 claims 1
- OEUVSBXAMBLPES-UHFFFAOYSA-L Calcium stearoyl-2-lactylate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC(=O)OC(C)C(=O)OC(C)C([O-])=O.CCCCCCCCCCCCCCCCCC(=O)OC(C)C(=O)OC(C)C([O-])=O OEUVSBXAMBLPES-UHFFFAOYSA-L 0.000 abstract description 26
- 235000010957 calcium stearoyl-2-lactylate Nutrition 0.000 abstract description 26
- GTNNCNWLWZLCGV-UHFFFAOYSA-M potassium;2-(2-octadecanoyloxypropanoyloxy)propanoate Chemical compound [K+].CCCCCCCCCCCCCCCCCC(=O)OC(C)C(=O)OC(C)C([O-])=O GTNNCNWLWZLCGV-UHFFFAOYSA-M 0.000 abstract description 24
- 229910052708 sodium Inorganic materials 0.000 abstract description 21
- 239000011734 sodium Substances 0.000 abstract description 21
- GDIUOQQOLKSNCD-UHFFFAOYSA-M sodium;2-(2-docosanoyloxypropanoyloxy)propanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCCCCC(=O)OC(C)C(=O)OC(C)C([O-])=O GDIUOQQOLKSNCD-UHFFFAOYSA-M 0.000 abstract description 10
- 239000000654 additive Substances 0.000 abstract 2
- 229940071209 stearoyl lactylate Drugs 0.000 abstract 1
- 239000008162 cooking oil Substances 0.000 description 23
- 238000010410 dusting Methods 0.000 description 17
- 230000000694 effects Effects 0.000 description 14
- 239000007787 solid Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 239000003112 inhibitor Substances 0.000 description 10
- 238000005189 flocculation Methods 0.000 description 9
- 230000016615 flocculation Effects 0.000 description 9
- 238000005429 turbidity Methods 0.000 description 9
- POULHZVOKOAJMA-UHFFFAOYSA-N Lauric acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 8
- 239000003995 emulsifying agent Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 239000002540 palm oil Substances 0.000 description 7
- 229940045902 sodium stearyl fumarate Drugs 0.000 description 7
- STFSJTPVIIDAQX-LTRPLHCISA-M sodium;(E)-4-octadecoxy-4-oxobut-2-enoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCOC(=O)\C=C\C([O-])=O STFSJTPVIIDAQX-LTRPLHCISA-M 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- UKMSUNONTOPOIO-UHFFFAOYSA-N Behenic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 6
- 235000019482 Palm oil Nutrition 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- 235000019197 fats Nutrition 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- NTYZDAJPNNBYED-UHFFFAOYSA-M sodium;2-(2-dodecanoyloxypropanoyloxy)propanoate Chemical compound [Na+].CCCCCCCCCCCC(=O)OC(C)C(=O)OC(C)C([O-])=O NTYZDAJPNNBYED-UHFFFAOYSA-M 0.000 description 4
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 description 3
- 235000021357 Behenic acid Nutrition 0.000 description 3
- 229940067606 Lecithin Drugs 0.000 description 3
- 229940116226 behenic acid Drugs 0.000 description 3
- 229950008690 docosanoic acid Drugs 0.000 description 3
- 235000019869 fractionated palm oil Nutrition 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 239000000787 lecithin Substances 0.000 description 3
- 235000010445 lecithin Nutrition 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 235000011837 pasties Nutrition 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- -1 CITREMs) Substances 0.000 description 2
- 240000003133 Elaeis guineensis Species 0.000 description 2
- 239000005639 Lauric acid Substances 0.000 description 2
- DCXXMTOCNZCJGO-UHFFFAOYSA-N Stearin Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 2
- 230000000111 anti-oxidant Effects 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000010411 cooking Methods 0.000 description 2
- 238000004332 deodorization Methods 0.000 description 2
- 230000002708 enhancing Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000006011 modification reaction Methods 0.000 description 2
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 229940092258 rosemary extract Drugs 0.000 description 2
- 235000020748 rosemary extract Nutrition 0.000 description 2
- 239000001233 rosmarinus officinalis l. extract Substances 0.000 description 2
- 125000005480 straight-chain fatty acid group Chemical group 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 235000006008 Brassica napus var napus Nutrition 0.000 description 1
- 235000006618 Brassica rapa subsp oleifera Nutrition 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- 244000188595 Brassica sinapistrum Species 0.000 description 1
- 229940043253 Butylated Hydroxyanisole Drugs 0.000 description 1
- 239000004255 Butylated hydroxyanisole Substances 0.000 description 1
- 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 1
- 235000001950 Elaeis guineensis Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Natural products OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 240000007842 Glycine max Species 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- WBHHMMIMDMUBKC-QJWNTBNXSA-N Ricinoleic acid Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(O)=O WBHHMMIMDMUBKC-QJWNTBNXSA-N 0.000 description 1
- WBHHMMIMDMUBKC-GKUQOKNUSA-N Ricinoleic acid Natural products CCCCCC[C@H](O)C\C=C/CCCCCCCC(O)=O WBHHMMIMDMUBKC-GKUQOKNUSA-N 0.000 description 1
- 238000010793 Steam injection (oil industry) Methods 0.000 description 1
- PVNIQBQSYATKKL-UHFFFAOYSA-N Tripalmitin Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCC PVNIQBQSYATKKL-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 235000008984 brauner Senf Nutrition 0.000 description 1
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002288 cocrystallisation Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000001419 dependent Effects 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 235000018927 edible plant Nutrition 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000009884 interesterification Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000010773 plant oil Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000002195 synergetic Effects 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 125000002640 tocopherol group Chemical group 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- 229930003799 tocopherols Natural products 0.000 description 1
- 229960001947 tripalmitin Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
- A23D9/013—Other fatty acid esters, e.g. phosphatides
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/02—Other edible oils or fats, e.g. shortenings, cooking oils characterised by the production or working-up
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/06—Preservation of finished products
Abstract
There is provided a palm olein composition comprising: (a) palm olein oil (b) a lactic acid ester selected from an ester of lactic acid and a C12 to C22 fatty acid, salts thereof and mixtures thereof, wherein the oil exhibits reduced crystallisation during storage. The lactic acid ester may be sodium stearoyl lactylate, potassium stearoyl lactylate, calcium stearoyl lactylate, sodium palmitoyl lactylate, sodium lauryl lactylate, sodium behenoyl lactylate, or mixtures thereof. The palm olein composition may further comprise sorbitan tristearate (STS), a polyglycerol ester, a second oil or other further additives. um stearoyl lactylate, potassium stearoyl lactylate, calcium stearoyl lactylate, sodium palmitoyl lactylate, sodium lauryl lactylate, sodium behenoyl lactylate, or mixtures thereof. The palm olein composition may further comprise sorbitan tristearate (STS), a polyglycerol ester, a second oil or other further additives.
Description
PALM OLEIN OIL COMPOSITION
The present invention relates to a composition. In particular, the present invention
relates to a palm olein oil composition containing a material that inhibits crystallisation of
fat present in the palm olein oil. The invention further relates to processes for inhibiting
crystallisation of said fat and to use of the crystallisation inhibitor.
INTRODUCTION
Palm olein is globally used as cooking oil. Palm olein having an iodine value of 56 or
more is often used in cooking oils in many Asian countries, but also to some extent in
South America, especially in domestic situations. One of the quality criteria for cooking
oil is the ability of the oil to stay crystal-free during storage, for example in a
supermarket. High premium cooking oil is mostly free of any visible crystal formation
during long storage time. Initial crystallisation is commonly, although not exclusively,
visible as a thin fat crystal layer at the bottom.
Palm olein is produced from palm oil by fractionation – usually by dry fractionations
where no solvents are used. Palm olein is the liquid fraction of palm oil and the high
melting triglycerides such as PPP (tripalmitin) are removed from or at least reduced to a
low level in the olein fraction. This is illustrated in Figure 1, which shows the different
palm oil fractions. It is noted that the first olein (single fractionated olein) can be
fractionated further to a palm mid fraction and double fractionated olein. The double
fractionated olein has less tendency to crystallise than the single fractionated olein at
typical storage temperature (of approximately 20 C).
Traditionally, the olein fraction has been the valuable part of palm oil and oil producers
tend to increase the olein yield during fractionation by minimising the amount of palm
stearine that is removed during fractionation. This however tends to increase the risk of
crystallisation in the palm olein. Hence in practice it is a compromise between yield and
cooking oil quality. This balance is often addressed to some degree with the
introduction of anticrystallisers into the oil. Diglycerides are also commonly found in
palm oil, and can concentrate into the olein fraction where they act to increase the cloud
point. Anticrystallizers can be useful in lengthening the period of clarity obtained from
such diglyceride containing oleins.
For many years sorbitan tristearate (STS) has been sold as an anticrystalliser in
cooking oil. The window where STS provides satisfactory results, is however quite
narrow. Below 20 C STS functionality progressively decreases. In well fractionated
olein, STS can delay the onset of crystallisation by a factor of 10. However, the effect
depends very much on the olein composition. A further improvement in inhibition of fat
crystallisation may be obtained by combining STS with soy lecithin. However, due to the
colouring effect of lecithin in cooking oil during heating, the inclusion of lecithin is not a
practical solution. Yet further improvement can be obtained by blending palm olein with
liquid oils such as soyabean oil. It is known in the art that such blends can also be
treated with STS in order to extend the time before noticeable crystallisation occurs.
However, such liquid oils are usually more expensive than palm olein and it would be
desirable to use less of them. To some extent STS allows this.
SUMMARY OF INVENTION
In a first aspect the present invention provides a palm olein composition comprising:
(a) palm olein oil
(b) a lactic acid ester selected from an ester of lactic acid and a C12 to C22 fatty acid,
salts thereof and mixtures thereof.
In a second aspect the present invention provides a process for inhibiting crystallisation
of triglyceride in palm olein oil, the process comprising the step of combining with the
palm olein oil, a lactic acid ester selected from an ester of lactic acid and a C12 to C22
fatty acid, salts thereof and mixtures thereof.
In a third aspect the present invention provides use of a lactic acid ester selected from
an ester of lactic acid and a C12 to C22 fatty acid, salts thereof and mixtures thereof,
for inhibiting crystallisation of triglyceride in palm olein oil.
The present invention provides a crystallisation inhibitor for the inhibition of
crystallisation of triglycerides in palm olein. In particular the present inhibitor, namely a
lactic acid ester selected from an ester of lactic acid and a C12 to C22 fatty acid, salts
thereof and mixtures thereof, provides inhibition of crystallisation of triglycerides in palm
olein.
It will be understood by one skilled in the art that in the context of the present invention
the term "inhibition" or "inhibitor" in relation to crystallisation means that the material
reduces the amount of triglyceride that crystallizes in a given period and/or increases
the time before which a given amount of triglyceride has crystallized. Although it is
desired that all triglyceride crystallisation is prevented during likely storage periods, this
is not an essential requirement for a crystallisation inhibitor.
The present inventors have particularly found that not only may the presently described
lactic acid esters inhibit crystallisation of triglyceride in palm olein oil, they may also
enhance the effect of STS as a crystallisation inhibitor. This was unexpected. Thus not
only do the presently described lactic acid esters act as a crystallisation inhibitor
themselves, but they may also be combined with the known inhibitor STS to provide a
beneficial effect. In this aspect the present invention provides
• a palm olein composition comprising:
(a) palm olein oil;
(b) a lactic acid ester selected from an ester of lactic acid and a C12 to C22 fatty
acid, salts thereof and mixtures thereof.
(c) sorbitan tristearate.
• a process for inhibiting crystallisation of triglyceride in palm olein oil, the process
comprising the step of combining
(a) a lactic acid ester selected from an ester of lactic acid and a C12 to C22 fatty
acid, salts thereof and mixtures thereof, and
(b) sorbitan tristearate, with the palm olein oil.use of (a) a lactic acid ester
selected from an ester of lactic acid and a C12 to C22 fatty acid, salts thereof
and mixtures thereof, and (b) sorbitan tristearate for inhibiting crystallisation of
triglyceride in palm olein oil.
For ease of reference, these and further aspects of the present invention are now
discussed under appropriate section headings. However, the teachings under each
section are not necessarily limited to each particular section.
DETAILED DESCRIPTION
As discussed herein, the present invention provides a palm olein composition
comprising:
(a) palm olein oil
(b) a lactic acid ester selected from an ester of lactic acid and a C12 to C22 fatty acid,
salts thereof and mixtures thereof.
Palm Olein Oil
Palm oil is an edible plant oil derived from the pulp of the fruit of the oil palm Elaeis
guineensis. Palm oil is fractionated with crystallisation and separation processes to
obtain a solid stearine fraction and a liquid olein fraction. Palm olein oil as referred to
herein is a liquid fraction of fractionated palm oil, such as the liquid fraction of single or
double fractionated palm oil. Palm olein oil as referred to herein may be a liquid fraction
of fractionated palm oil having an iodine value of 56 or more, such as an iodine value of
60 or more.
In one preferred aspect the palm olein is double fractionated.
A preferred palm olein oil is deodorised palm olein oil or refined palm olein oil. The palm
olein may be refined by chemical means or by physical means. Typical chemical
refining comprises steps of contacting the palm olein with caustic, washing the caustic
containing material, bleaching and then deodorising. Typical physical refining comprises
the steps of bleaching the palm olein, deodorising and then "stripping off" under a
vacuum with steam injection. A preferred palm olein oil is deodorised palm olein oil.
When the palm olein oil is deodorised palm olein oil, the ester of (i) lactic acid and (ii) a
C12 to C22 fatty acid, or a salt thereof, may be added to the oil before or after
deodorization. It is preferred to add the ester/salt after deodorization because the
ester/salt may have a tendency to act as an interesterification catalyst.
The palm olein oil may in one aspect be the sole oil component of the palm olein
composition. However, in other aspects the palm olein composition may contain one or
more oils in addition to the palm olein oil. For example, the one or more oils may be
selected from other 'soft oils'. Examples of soft oils are moringa oil, soy oil, cottonseed
oil, canola oil, rapeseed oil (such as high oleic rapeseed oil, that is rapeseed oil
containing at least 82% oleic acid based on the total weight of fatty acids; and such as
low erucic acid rapeseed oil or high erucic acid rapeseed oil, low erucic acid rapeseed
oil may also be known as canola oil), peanut oil, rice bran oil (such as dewaxed rice
bran oil), corn oil, safflower oil, sunflower oil (such high oleic sunflower oil, that is
sunflower oil containing at least 82% oleic acid based on the total weight of fatty acids),
linseed oil, olive oil, peanut oil and mixtures thereof.
When the palm olein oil is combined with one or more further oils (such as a soft oil) the
oils may be combined in any suitable ratio. Particularly preferred weight ratios of soft oil
to palm olein are 9:1 to 0:1, such as 9:1 to 1:9, such as 8:1 to 1:8, such as 7:1 to 1:7,
such as 6:1 to 1:6, such as 5:1 to 1:5, such as 4:1 to 1:4, such as 3:1 to 1:3, such as 2:1
to 1:2, such as approximately 1:1. In one aspect weight ratios of soft oil to palm olein
are 1:1 to 0:1, such as 1:2 to 0:1, such as 1:3 to 0:1, such as 1:3 to 0:1, such as 1:4 to
0:1, such as 1:5 to 0:1, such as 1:6 to 0:1, such as 1:7 to 0:1, such as 1:8 to 0:1, such
as 1:9 to 0:1.
Lactic Acid
The ester used in the present invention is an ester of lactic acid. Lactic acid is also
known as 2-hydroxypropanoic acid.
In one preferred aspect the ester is a lactic acid ester selected from an ester of lactic
acid and a C12 to C22 fatty acid, salts thereof and mixtures thereof.
Fatty Acid
The fatty acid used to prepare the lactic acid ester of the present invention is a C12 to
C22 fatty acid.
In one aspect the fatty acid is a C12 to C22 fatty acid. Preferably the fatty acid is a C16
to C22 fatty acid. Preferably the fatty acid is a C18 to C22 fatty acid. Preferably the fatty
acid is a C16 to C20 fatty acid. Preferably the fatty acid is a C18 to C20 fatty acid.
Preferably the fatty acid is a C16 to C18 fatty acid. In one aspect the fatty acid is a C18
fatty acid. In one aspect the fatty acid is a C16 fatty acid. Preferably the fatty acid is a
mixture of C16 fatty acid and C18 fatty acid.
In one aspect the fatty acid is a C12 fatty acid. In one aspect the fatty acid is a C14 fatty
acid. In one aspect the fatty acid is a C16 fatty acid. In one aspect the fatty acid is a
C18 fatty acid. In one aspect the fatty acid is a C20 fatty acid. In one aspect the fatty
acid is a C22 fatty acid.
The fatty acid may be any suitable C12 to C22 to provide the desired crystallisation
inhibition. The fatty acid may be a saturated or unsaturated fatty acid. If the fatty acid is
unsaturated it may have one or more degrees of unsaturation, for example one, two or
three degrees of unsaturation (that is it contains, for example, one two or three double
bonds). In respect of the one or more double bonds, each may independently be in the
cis configuration or in the trans configuration. In one aspect each double bond is in the
trans configuration. In one aspect each double bond is in the cis configuration. In one
preferred aspect, the fatty acid is a saturated fatty acid.
The fatty acid may be a straight chain fatty acid or a branched chain fatty acid. In one
aspect the fatty acid may be a straight chain fatty acid, which may be saturated or
unsaturated.
In a preferred aspect the fatty acid is a straight chain saturated fatty acid. In a preferred
aspect the fatty acid is a saturated fatty acid.
In a preferred aspect the fatty acid may be substituted by one or more hydroxyl groups.
This fatty acid may be a saturated or unsaturated fatty acid. An example of such a fatty
acid is ricinoleic acid.
Among the fatty acids that may be used in the present invention are oleic acid, stearic
acid, lauric acid, palmitic acid and behenic acid. Particularly preferred fatty acids are
stearic acid, palmitic and behenic acid, preferably stearic acid and palmitic acid. Most
preferred is stearic acid. Highly preferred saturated fatty acids are palmitic acid, stearic
acid or mixture thereof. In one aspect the fatty acid comprises at least oleic acid. In one
aspect the fatty acid comprises at least lauric acid. In one aspect the fatty acid
comprises at least palmitic acid. In one aspect the fatty acid comprises at least behenic
acid. In one preferred aspect the fatty acid comprises at least stearic acid. In one
preferred aspect the fatty acid is at least palmitic acid. In one preferred aspect the fatty
acid comprises a mixture of stearic acid and palmitic acid.
Salt
The ester of the present invention formed from lactic acid may, as appreciated by one
skilled in the art, have an acid group. The acid group of the ester may in one preferred
aspect be in the form of a salt. The salt may be any suitable metal salt. In particular the
salt may be any metal salt of a Group I (alkali metal) or Group II (alkaline earth metal).
In one preferred aspect the salt is a sodium, calcium or potassium salt of the ester of
lactic acid and a C12 to C22 fatty acid. In one aspect the salt is a potassium salt. In a
preferred aspect the salt is a sodium salt. In one aspect the salt is a calcium salt.
Ester
It will be appreciated by one skilled in the art that the esters of the present invention
may be denoted by the following structures. In respect of the lactic acid esters, the
structure is:
O CH O
R C O C C O
wherein n is from 1 to 5, X is a metal ion or H, R is a C12 to C22 fatty acid residue.
Preferably n is from 1 to 3. More preferably n is approximately 2.
X is preferably selected from H, Na, Ca and K. In one aspect X is K. X is more
preferably selected from Na and Ca.
In a preferred embodiment the ester is selected from the group consisting of sodium
stearoyl lactylate, potassium stearoyl lactylate, calcium stearoyl lactylate, sodium oleyl
lactylate, sodium palmitoyl lactylate, sodium lauryl lactylate, sodium behenoyl lactylate,
and mixtures thereof.
Thus in one aspect the present invention provides a palm olein composition comprising:
(a) palm olein oil
(b) a compound selected from the group consisting of sodium stearoyl lactylate,
potassium stearoyl lactylate, calcium stearoyl lactylate, sodium oleyl lactylate, sodium
palmitoyl lactylate, sodium lauryl lactylate, sodium behenoyl lactylate, and mixtures
thereof.
In a second aspect the present invention provides a process for inhibiting crystallisation
of triglyceride in palm olein oil, the process comprising the step of combining with the
palm olein oil, a compound selected from the group consisting of sodium stearoyl
lactylate, potassium stearoyl lactylate, calcium stearoyl lactylate, sodium oleyl lactylate,
sodium palmitoyl lactylate, sodium lauryl lactylate, sodium behenoyl lactylate, and
mixtures thereof.
In a preferred embodiment the ester is selected from the group consisting of sodium
stearoyl lactylate, potassium stearoyl lactylate, calcium stearoyl lactylate, sodium
palmitoyl lactylate, sodium lauryl lactylate, sodium behenoyl lactylate, and mixtures
thereof.
In a highly preferred embodiment the ester is sodium stearoyl lactylate.
In one aspect the ester is a sodium, calcium or potassium salt of the ester of lactic acid
and a C12 fatty acid. In one aspect the ester is a sodium, calcium or potassium salt of
the ester of lactic acid and a C14 fatty acid. In one aspect the ester is a sodium, calcium
or potassium salt of the ester of lactic acid and a C16 fatty acid. In one aspect the ester
is a sodium, calcium or potassium salt of the ester of lactic acid and a C18 fatty acid. In
one aspect the ester is a sodium, calcium or potassium salt of the ester of lactic acid
and a C20 fatty acid. In one aspect the ester is a sodium, calcium or potassium salt of
the ester of lactic acid and a C22 fatty acid.
In one aspect the ester is a sodium or calcium salt of the ester of lactic acid and a C12
fatty acid. In one aspect the ester is a sodium or calcium salt of the ester of lactic acid
and a C14 fatty acid. In one aspect the ester is a sodium or calcium salt of the ester of
lactic acid and a C16 fatty acid. In one aspect the ester is a sodium or calcium salt of
the ester of lactic acid and a C18 fatty acid. In one aspect the ester is a sodium or
calcium salt of the ester of lactic acid and a C20 fatty acid. In one aspect the ester is a
sodium or calcium salt of the ester of lactic acid and a C22 fatty acid.
In one aspect the ester is a sodium salt of the ester of lactic acid and a C12 fatty acid.
In one aspect the ester is a sodium salt of the ester of lactic acid and a C14 fatty acid.
In one aspect the ester is a sodium salt of the ester of lactic acid and a C16 fatty acid.
In one aspect the ester is a sodium salt of the ester of lactic acid and a C18 fatty acid.
In one aspect the ester is a sodium salt of the ester of lactic acid and a C20 fatty acid.
In one aspect the ester is a sodium salt of the ester of lactic acid and a C22 fatty acid.
The ester or salt thereof should of course be present in any suitable amount to provide
the desired crystallisation inhibition. The minimum amount may be readily determined
by one skilled in the art. For example, The ester or salt thereof may be present in an
amount of at least 0.001 wt%, such in an amount of at least 0.002 wt%, such in an
amount of at least 0.003 wt%, such in an amount of at least 0.005 wt%, such in an
amount of at least 0.007 wt%, such in an amount of at least 0.01 wt%, such in an
amount of at least 0.02 wt% based on the weight of palm olein oil, such in an amount of
at least 0.05 wt% based on the weight of palm olein oil, such in an amount of at least
0.1 wt% based on the weight of palm olein oil. It will be appreciated by one skilled in the
art that below a certain level the ester or salt thereof will not have the desired
crystallisation inhibitory effect. The amount of ester or salt thereof required may be
readily determined by one skilled in the art by comparison of the palm olein in
accordance with the experimental methods described herein with the ester or salt
thereof present at varying amounts.
It may be desirable for the ester or salt thereof to be present in maximum amounts. The
maximum amount may be determined by one or more considerations. One important
consideration is the amount permitted by the statutes and regulations of any country in
which the product is to be sold. The maximum amount may be determined by one
skilled in the art dependent on the relevant conditions, such as statute and regulation.
For example, the ester or salt thereof may be present in an amount of no greater than
1.0 wt%, such in an amount of no greater than 0.7 wt%, such in an amount of no
greater than 0.5 wt%, such in an amount of no greater than 0.3 wt%, such in an amount
of no greater than 0.2 wt%, such in an amount of no greater than 0.1 wt%, such as in an
amount of no greater than 0.05 wt%, such as in an amount of no greater than 0.04 wt%,
such as in an amount of no greater than 0.03 wt%, such as in an amount of no greater
than 0.02 wt%, such as in an amount of no greater than 0.01 wt% based on the weight
of palm olein oil.
Further Components
The palm olein composition may optionally contain one or more further components in
addition to the ester or salt thereof. These components may be for example
antioxidants, antispattering agents, emulsifiers (such as CITREMs), lecithin, and
flavourings. Antioxidants that may be present in the composition include GRINDOX 204
(available from DuPont formerly Danisco A/S), GUARDIAN Rosemary Extract 08
(available from DuPont formerly Danisco A/S), GUARDIAN Rosemary Extract 201
(available from DuPont formerly Danisco A/S), butylated hydroxyanisole, tocopherols
and mixtures thereof.
In one preferred aspect, and as discussed herein, the palm olein composition further
comprises (c) sorbitan tristearate (STS). If present the STS should of course be present
in any suitable amount to provide the desired effect, such as improved crystallisation
inhibition. This amount may be readily determined by one skilled in the art. For
example, the STS may be present in an amount of at least 0.001 wt%, such in an
amount of at least 0.002 wt%, such in an amount of at least 0.003 wt%, such in an
amount of at least 0.005 wt%, such in an amount of at least 0.007 wt%, such in an
amount of at least 0.01 wt%, such in an amount of at least 0.02 wt%, such in an amount
of at least 0.04 wt%, such in an amount of at least 0.06 wt%, such in an amount of at
least 0.08 wt% based on the weight of palm olein oil, such in an amount of at least 0.1
wt% based on the weight of palm olein oil, such in an amount of at least 0.15 wt%
based on the weight of palm olein oil.
It may be desirable for STS, if present, to be present in maximum amounts. These may
be determined by one skilled in the art. For example, the STS may be present in an
amount of no greater than 1.0 wt%, such as in an amount of no greater than 0.7 wt%,
such as in an amount of no greater than 0.5 wt%, such as in an amount of no greater
than 0.3 wt%, such as in an amount of no greater than 0.2 wt%, such as in an amount
of no greater than 0.1 wt%, such as in an amount of no greater than 0.05 wt%, such as
in an amount of no greater than 0.03 wt%, such as in an amount of no greater than 0.02
wt%, such as in an amount of no greater than 0.01 wt% based on the weight of palm
olein oil.
Preferred amounts of ester or salt thereof and STS are given in the table below. For
each preferred amount of ester or salt thereof, the preferred amounts of STS are listed
in the adjoining column.
Ester or Salt thereof STS
(based on the weight of palm (based on the weight of palm olein oil)
olein oil)
at least 0.001 wt% at least 0.001 wt% at least 0.002 wt%
at least 0.003 wt% at least 0.005 wt%
at least 0.007 wt% at least 0.01 wt%
at least 0.02 wt%
no greater than 1.0 wt% no greater than 0.7 wt%
no greater than 0.5 wt% no greater than 0.3 wt%
no greater than 0.2 wt% no greater than 0.1 wt%
no greater than 0.05 wt% no greater than 0.03
no greater than 0.02 wt% no greater than 0.01
at least 0.002 wt% at least 0.001 wt% at least 0.002 wt%
at least 0.003 wt% at least 0.005 wt%
at least 0.007 wt% at least 0.01 wt%
at least 0.02 wt%
no greater than 1.0 wt% no greater than 0.7 wt%
no greater than 0.5 wt% no greater than 0.3 wt%
no greater than 0.2 wt% no greater than 0.1 wt%
no greater than 0.05 wt% no greater than 0.03
no greater than 0.02 wt% no greater than 0.01
at least 0.003 wt% at least 0.001 wt% at least 0.002 wt%
at least 0.003 wt% at least 0.005 wt%
at least 0.007 wt% at least 0.01 wt%
at least 0.02 wt%
no greater than 1.0 wt% no greater than 0.7 wt%
no greater than 0.5 wt% no greater than 0.3 wt%
no greater than 0.2 wt% no greater than 0.1 wt%
Ester or Salt thereof STS
(based on the weight of palm (based on the weight of palm olein oil)
olein oil)
no greater than 0.05 wt% no greater than 0.03
no greater than 0.02 wt% no greater than 0.01
at least 0.005 wt% at least 0.001 wt% at least 0.002 wt%
at least 0.003 wt% at least 0.005 wt%
at least 0.007 wt% at least 0.01 wt%
at least 0.02 wt%
no greater than 1.0 wt% no greater than 0.7 wt%
no greater than 0.5 wt% no greater than 0.3 wt%
no greater than 0.2 wt% no greater than 0.1 wt%
no greater than 0.05 wt% no greater than 0.03
no greater than 0.02 wt% no greater than 0.01
at least 0.007 wt% at least 0.001 wt% at least 0.002 wt%
at least 0.003 wt% at least 0.005 wt%
at least 0.007 wt% at least 0.01 wt%
at least 0.02 wt%
no greater than 1.0 wt% no greater than 0.7 wt%
no greater than 0.5 wt% no greater than 0.3 wt%
no greater than 0.2 wt% no greater than 0.1 wt%
no greater than 0.05 wt% no greater than 0.03
no greater than 0.02 wt% no greater than 0.01
at least 0.01 wt% at least 0.001 wt% at least 0.002 wt%
at least 0.003 wt% at least 0.005 wt%
at least 0.007 wt% at least 0.01 wt%
at least 0.02 wt%
no greater than 1.0 wt% no greater than 0.7 wt%
no greater than 0.5 wt% no greater than 0.3 wt%
Ester or Salt thereof STS
(based on the weight of palm (based on the weight of palm olein oil)
olein oil)
no greater than 0.2 wt% no greater than 0.1 wt%
no greater than 0.05 wt% no greater than 0.03
no greater than 0.02 wt% no greater than 0.01
at least 0.02 wt% at least 0.001 wt% at least 0.002 wt%
at least 0.003 wt% at least 0.005 wt%
at least 0.007 wt% at least 0.01 wt%
at least 0.02 wt%
no greater than 1.0 wt% no greater than 0.7 wt%
no greater than 0.5 wt% no greater than 0.3 wt%
no greater than 0.2 wt% no greater than 0.1 wt%
no greater than 0.05 wt% no greater than 0.03
no greater than 0.02 wt% no greater than 0.01
no greater than 1.0 wt% at least 0.001 wt% at least 0.002 wt%
at least 0.003 wt% at least 0.005 wt%
at least 0.007 wt% at least 0.01 wt%
at least 0.02 wt%
no greater than 1.0 wt% no greater than 0.7 wt%
no greater than 0.5 wt% no greater than 0.3 wt%
no greater than 0.2 wt% no greater than 0.1 wt%
no greater than 0.05 wt% no greater than 0.03
no greater than 0.02 wt% no greater than 0.01
no greater than 0.7 wt% at least 0.001 wt% at least 0.002 wt%
at least 0.003 wt% at least 0.005 wt%
at least 0.007 wt% at least 0.01 wt%
at least 0.02 wt%
no greater than 1.0 wt% no greater than 0.7 wt%
Ester or Salt thereof STS
(based on the weight of palm (based on the weight of palm olein oil)
olein oil)
no greater than 0.5 wt% no greater than 0.3 wt%
no greater than 0.2 wt% no greater than 0.1 wt%
no greater than 0.05 wt% no greater than 0.03
no greater than 0.02 wt% no greater than 0.01
no greater than 0.5 wt% at least 0.001 wt% at least 0.002 wt%
at least 0.003 wt% at least 0.005 wt%
at least 0.007 wt% at least 0.01 wt%
at least 0.02 wt%
no greater than 1.0 wt% no greater than 0.7 wt%
no greater than 0.5 wt% no greater than 0.3 wt%
no greater than 0.2 wt% no greater than 0.1 wt%
no greater than 0.05 wt% no greater than 0.03
no greater than 0.02 wt% no greater than 0.01
no greater than 0.3 wt% at least 0.001 wt% at least 0.002 wt%
at least 0.003 wt% at least 0.005 wt%
at least 0.007 wt% at least 0.01 wt%
at least 0.02 wt%
no greater than 1.0 wt% no greater than 0.7 wt%
no greater than 0.5 wt% no greater than 0.3 wt%
no greater than 0.2 wt% no greater than 0.1 wt%
no greater than 0.05 wt% no greater than 0.03
no greater than 0.02 wt% no greater than 0.01
no greater than 0.2 wt% at least 0.001 wt% at least 0.002 wt%
at least 0.003 wt% at least 0.005 wt%
at least 0.007 wt% at least 0.01 wt%
at least 0.02 wt%
Ester or Salt thereof STS
(based on the weight of palm (based on the weight of palm olein oil)
olein oil)
no greater than 1.0 wt% no greater than 0.7 wt%
no greater than 0.5 wt% no greater than 0.3 wt%
no greater than 0.2 wt% no greater than 0.1 wt%
no greater than 0.05 wt% no greater than 0.03
no greater than 0.02 wt% no greater than 0.01
no greater than 0.1 wt% at least 0.001 wt% at least 0.002 wt%
at least 0.003 wt% at least 0.005 wt%
at least 0.007 wt% at least 0.01 wt%
at least 0.02 wt%
no greater than 1.0 wt% no greater than 0.7 wt%
no greater than 0.5 wt% no greater than 0.3 wt%
no greater than 0.2 wt% no greater than 0.1 wt%
no greater than 0.05 wt% no greater than 0.03
no greater than 0.02 wt% no greater than 0.01
no greater than 0.05 wt% at least 0.001 wt% at least 0.002 wt%
at least 0.003 wt% at least 0.005 wt%
at least 0.007 wt% at least 0.01 wt%
at least 0.02 wt%
no greater than 1.0 wt% no greater than 0.7 wt%
no greater than 0.5 wt% no greater than 0.3 wt%
no greater than 0.2 wt% no greater than 0.1 wt%
no greater than 0.05 wt% no greater than 0.03
no greater than 0.02 wt% no greater than 0.01
no greater than 0.03 wt% at least 0.001 wt% at least 0.002 wt%
at least 0.003 wt% at least 0.005 wt%
at least 0.007 wt% at least 0.01 wt%
Ester or Salt thereof STS
(based on the weight of palm (based on the weight of palm olein oil)
olein oil)
at least 0.02 wt%
no greater than 1.0 wt% no greater than 0.7 wt%
no greater than 0.5 wt% no greater than 0.3 wt%
no greater than 0.2 wt% no greater than 0.1 wt%
no greater than 0.05 wt% no greater than 0.03
no greater than 0.02 wt% no greater than 0.01
no greater than 0.02 wt% at least 0.001 wt% at least 0.002 wt%
at least 0.003 wt% at least 0.005 wt%
at least 0.007 wt% at least 0.01 wt%
at least 0.02 wt%
no greater than 1.0 wt% no greater than 0.7 wt%
no greater than 0.5 wt% no greater than 0.3 wt%
no greater than 0.2 wt% no greater than 0.1 wt%
no greater than 0.05 wt% no greater than 0.03
no greater than 0.02 wt% no greater than 0.01
no greater than 0.01 wt% at least 0.001 wt% at least 0.002 wt%
at least 0.003 wt% at least 0.005 wt%
at least 0.007 wt% at least 0.01 wt%
at least 0.02 wt%
no greater than 1.0 wt% no greater than 0.7 wt%
no greater than 0.5 wt% no greater than 0.3 wt%
no greater than 0.2 wt% no greater than 0.1 wt%
no greater than 0.05 wt% no greater than 0.03
no greater than 0.02 wt% no greater than 0.01
If STS is present, the ratio of STS:Ester/Salt may be from 15:1 to 5:1, such as 12:1 to
7:1, such as 10:1 to 7:1, such as 9:1 to 7:1, such as approximately 8:1.
If STS is present, in one aspect (for example when the palm olein is stored at a
temperature of at least 10 C) it is preferred that the ratio of STS:Ester/Salt is from 15:1
to 1:15, such as 15:1 to 1:14, such as 15:1 to 1:13, such as 15:1 to 1:12, such as 15:1
to 1:11, such as 15:1 to 1:10, such as 15:1 to 1:9, such as 15:1 to 1:8, such as 15:1 to
1:7, such as 15:1 to 1:6, such as 15:1 to 1:5, such as 15:1 to 1:4, such as 15:1 to 1:3,
such as 15:1 to 1:2, such as 15:1 to 1:1, such as 14:1 to 1:15, such as 13:1 to 1:15,
such as 12:1 to 1:15, such as 11:1 to 1:15, such as 10:1 to 1:15, such as 9:1 to 1:15,
such as 8:1 to 1:15, such as 7:1 to 1:15, such as 6:1 to 1:15, such as 5:1 to 1:15, such
as 4:1 to 1:15, such as 3:1 to 1:15, such as 2:1 to 1:15, such as 1:1 to 1:15, such as
14:1 to 1:5, such as 13:1 to 1:5, such as 12:1 to 1:5, such as 11:1 to 1:5, such as 10:1
to 1:5, such as 9:1 to 1:5, such as 8:1 to 1:5, such as 7:1 to 1:5, such as 6:1 to 1:5,
such as 5:1 to 1:5, such as 5:1 to 1:4, such as 5:1 to 1:3, such as 5:1 to 1:2, such as 5:1
to 1:1, such as 4:1 to 1:2, such as 3:1 to 1:2, such as 2:1 to 1:2, such as 2:1 to 1:1,
such as 4:1 to 1:1, such as 3:1 to 1:1, such as 2:1 to 1:1, such as 2.5:1 to 1.5:1 such as
approximately 2:1.
If STS is present, in one aspect (for example when the palm olein is stored at a
temperature of at least 10 C) it is preferred that the ratio of STS:Ester/Salt is from 15:1
to 1:5, such as 15:1 to 1:4, such as 15:1 to 1:3, such as 15:1 to 1:2, such as 15:1 to 1:1,
such as 14:1 to 1:5, such as 13:1 to 1:5, such as 12:1 to 1:5, such as 11:1 to 1:5, such
as 10:1 to 1:5, such as 9:1 to 1:5, such as 8:1 to 1:5, such as 7:1 to 1:5, such as 6:1 to
1:5, such as 5:1 to 1:5, such as 5:1 to 1:4, such as 5:1 to 1:3, such as 5:1 to 1:2, such
as 5:1 to 1:1, such as 4:1 to 1:2, such as 3:1 to 1:2, such as 2:1 to 1:2, such as 2:1 to
1:1, such as 4:1 to 1:1, such as 3:1 to 1:1, such as 2:1 to 1:1, such as 2.5:1 to 1.5:1
such as approximately 2:1.
If STS is present, in one aspect (for example when the palm olein is stored at a
temperature of approximately 0 C) it is preferred that the ratio of STS:Ester/Salt is from
:1 to 1:15, such as 14:1 to 1:15, such as 13:1 to 1:15, such as 12:1 to 1:15, such as
11:1 to 1:15, such as 10:1 to 1:15, such as 9:1 to 1:15, such as 8:1 to 1:15, such as 7:1
to 1:15, such as 6:1 to 1:15, such as 5:1 to 1:15, such as 4:1 to 1:15, such as 3:1 to
1:15, such as 2:1 to 1:15, such as 1:1 to 1:15, such as 1:1 to 1:14, such as 1:1 to 1:13,
such as 1:1 to 1:12, such as 1:1 to 1:11, such as 1:1 to 1:10, such as 1:1 to 1:9, such as
1:2 to 1:14, such as 1:3 to 1:13, such as 1:4 to 1:12, such as 1:5 to 1:12, such as 1:6 to
1:12, such as 1:7 to 1:11, such as 1:8 to 1:10, such as approximately 1:9.
If STS is present, it is preferred that the amounts of STS and Ester/Salt based on the
combined amount of STS and Ester/Salt are selected from the following:
Ester/Salt (wt %) STS (wt %)
1-20 80-99
1-15 85-99
1-10 90-99
2-10 90-98
2-8 92-98
4-6 94-96
If STS is present, the combined STS and Ester/Salt may be dosed into the palm olein in
a total combined amount of 0.01 to 0.5 wt% based on the palm olein, such as in a total
combined amount of 0.01 to 0.4 wt% based on the palm olein, such as in a total
combined amount of 0.01 to 0.3 wt% based on the palm olein, such as in a total
combined amount of 0.01 to 0.2 wt% based on the palm olein, such as in a total
combined amount of 0.01 to 0.1 wt% based on the palm olein, such as in a total
combined amount of 0.02 to 0.1 wt% based on the palm olein, such as in a total
combined amount of 0.04 to 0.1 wt% based on the palm olein, such as in a total
combined amount of 0.05 to 0.1 wt% based on the palm olein. Preferably the combined
STS and Ester/Salt are dosed into the palm olein in a total combined amount of 0.06 to
0.08 wt% based on the palm olein.
If STS is present, it is preferred that the combined STS and Ester/Salt are dosed into
the palm olein in a total combined amount of 0.001 to 0.5 wt% based on the palm olein,
such as in a total combined amount of 0.001 to 0.4 wt% based on the palm olein, such
as in a total combined amount of 0.001 to 0.3 wt% based on the palm olein, such as in
a total combined amount of 0.001 to 0.2 wt% based on the palm olein, such as in a total
combined amount of 0.002 to 0.2 wt% based on the palm olein, such as in a total
combined amount of 0.003 to 0.2 wt% based on the palm olein, such as in a total
combined amount of 0.004 to 0.2 wt% based on the palm olein, such as in a total
combined amount of 0.005 to 0.2 wt% based on the palm olein, such as in a total
combined amount of 0.006 to 0.2 wt% based on the palm olein, such as in a total
combined amount of 0.007 to 0.2 wt% based on the palm olein, such as in a total
combined amount of 0.008 to 0.2 wt% based on the palm olein, such as in a total
combined amount of 0.009 to 0.2 wt% based on the palm olein, such as in a total
combined amount of 0.01 to 0.2 wt% based on the palm olein, such as in a total
combined amount of 0.01 to 0.15 wt% based on the palm olein, such as in a total
combined amount of 0.01 to 0.1 wt% based on the palm olein, such as in a total
combined amount of 0.01 to 0.09 wt% based on the palm olein, such as in a total
combined amount of 0.01 to 0.08 wt% based on the palm olein, such as in a total
combined amount of 0.01 to 0.07 wt% based on the palm olein, such as in a total
combined amount of 0.01 to 0.06 wt% based on the palm olein, such as in a total
combined amount of 0.01 to 0.05 wt% based on the palm olein, such as in a total
combined amount of 0.015 to 0.05 wt% based on the palm olein, such as in a total
combined amount of 0.02 to 0.05 wt% based on the palm olein.
In one aspect the STS has an acid value of no greater than 10. In a further aspect, the
STS has an acid value of no greater than 8. In a further aspect, the STS has an acid
value of no greater than 7. In a further aspect, the STS has an acid value of no greater
than 5. In a further aspect, the STS has an acid value of no greater than 4. In a further
aspect, the STS has an acid value of no greater than 3. In a further aspect, the STS has
an acid value of no greater than 2.
If STS is present, the STS and Ester/Salt may be dosed into the palm olein either
sequentially or together. If they are dosed sequentially, either the STS or the Ester/Salt
may be added first. The STS and Ester/Salt may be blended together for dosing as a
single material. For example, the STS and Ester/Salt may be co-crystallised and,
optionally then spray crystallised to form a powder, such that a single material of a
given ratio of STS to Ester/Salt is provided.
We have now surprisingly found that the esters described herein, such as SSL, may
enhance the effect of PGE, which is a known prior art anticrystalliser. In one preferred
aspect, and as discussed herein, the palm olein composition further comprises a
polyglycerol ester. The present inventors have further found that a lactic acid ester
selected from an ester of lactic acid and a C12 to C22 fatty acid, salts thereof and
mixtures thereof, may be combined with a polyglycerol ester as a crystallisation
inhibitor. Thus not only does the present lactic acid ester or fumaric acid ester act a
crystallisation inhibitor itself, but it may also be combined with a known polyglycerol
ester to provide a beneficial effect. In this aspect the present invention provides
• a palm olein composition comprising:
(a) palm olein oil;
(b) a lactic acid ester selected from an ester of lactic acid and a C12 to C22 fatty
acid, salts thereof and mixtures thereof.
(c) a polyglycerol ester.
• a process for inhibiting crystallisation of triglyceride in palm olein oil, the process
comprising the step of combining (a) a lactic acid ester selected from an ester of
lactic acid and a C12 to C22 fatty acid, salts thereof and mixtures thereof, and
(b) a polyglycerol ester with the palm olein oil.
• use of (a) a lactic acid ester selected from an ester of lactic acid and a C12 to
C22 fatty acid, salts thereof and mixtures thereof, and (b) a polyglycerol ester for
inhibiting crystallisation of triglyceride in palm olein oil.
If present, the polyglycerol ester should of course be present in any suitable amount to
provide the desired effect, such as improved crystallisation inhibition. This amount may
be readily determined by one skilled in the art.
The palm olein composition may contain both STS described herein and a polyglycerol
ester as described herein. Namely, there is provided a palm olein composition
comprising: (a) palm olein oil; (b) a lactic acid ester selected from an ester of lactic acid
and a C12 to C22 fatty acid, salts thereof and mixtures thereof, (c) a polyglycerol ester,
and (d) STS.
When the present palm olein composition contains solely palm olein oil and ester/salt,
then it will be appreciated that these components may be combined together in any
suitable manner. When further components are present it is envisaged that the
components may be combined in any suitable order or simultaneously. For example,
then STS is present the ester/salt may be combined with the oil and the STS added, the
STS may be combined with the oil and the ester/salt added, or the STS and ester/salt
combined and then contacted with the oil. In the latter aspect, the ester/salt may be
dissolved in liquid STS or the ester/salt may be dry mixed with STS.
Process
In one aspect the present invention provides a process for inhibiting crystallisation of
triglyceride in palm olein oil, the process comprising the step of combining with the palm
olein oil, a lactic acid ester selected from an ester of lactic acid and a C12 to C22 fatty
acid, salts thereof and mixtures thereof.
It will be appreciated that 'combining' as discussed herein may be by any suitable
means. For example the components may be mixed, melted, dissolved or combinations
thereof.
The process should provide inhibition of crystallisation across a range of temperatures
at which the palm olein composition is likely to be stored during acceptable handling. In
a preferred aspect, the crystallisation of triglyceride in the palm olein composition is
inhibited during storage of the palm olein composition at a temperature of less than
25 C, preferably the crystallisation of triglyceride in palm olein composition is inhibited
during storage of the palm olein composition at a temperature of less than 20 C,
preferably the crystallisation of triglyceride in palm olein composition is inhibited during
storage of the palm olein composition at a temperature of less than 18 C, preferably the
crystallisation of triglyceride in palm olein composition is inhibited during storage of the
palm olein oil at a temperature of less than 15 C, preferably the crystallisation of
triglyceride in palm olein composition is inhibited during storage of the palm olein
composition at a temperature of less than 12 C, preferably the crystallisation of
triglyceride in palm olein composition is inhibited during storage of the palm olein
composition at a temperature of less than 10 C, preferably the crystallisation of
triglyceride in palm olein composition is inhibited during storage of the palm olein
composition at a temperature of less than 5 C, preferably the crystallisation of
triglyceride in palm olein composition is inhibited during storage of the palm olein
composition at a temperature of at least 0 C.
In a preferred aspect, the crystallisation of triglyceride in the palm olein composition is
inhibited during storage of the palm olein composition at a temperature of approximately
C, preferably the crystallisation of triglyceride in palm olein composition is inhibited
during storage of the palm olein composition at a temperature of from 25 C to 20 C,
preferably the crystallisation of triglyceride in palm olein composition is inhibited during
storage of the palm olein composition at a temperature of from 25 C to 18 C, preferably
the crystallisation of triglyceride in palm olein composition is inhibited during storage of
the palm olein oil at a temperature of from 25 C to 15 C, preferably the crystallisation of
triglyceride in palm olein composition is inhibited during storage of the palm olein
composition at a temperature of from 25 C to 12 C, preferably the crystallisation of
triglyceride in palm olein composition is inhibited during storage of the palm olein
composition at a temperature of from 25 C to 10 C, preferably the crystallisation of
triglyceride in palm olein composition is inhibited during storage of the palm olein
composition at a temperature of from 25 C to 5 C, preferably the crystallisation of
triglyceride in palm olein composition is inhibited during storage of the palm olein
composition at a temperature of from 25 C to 0 C.
It is a requirement that the present invention inhibits crystallisation of triglyceride in the
palm olein oil. This inhibition may be any mechanism. Without being bound by theory it
is understood that the lactic acid ester described herein inhibits nucleation of the
triglyceride such that its crystallisation is inhibited.
It will be understood by one skilled in the art that the process steps described herein are
not exhaustive and that the invention may be practiced by addition of one or more steps
either before the steps recited herein, after the steps recited herein, intermediate to the
steps recited herein, and combinations thereof.
Further Aspects
In one further aspect the present invention provides a palm olein composition
comprising: (a) palm olein oil (b) an ester of (i) lactic acid and (ii) a C12 to C22 fatty
acid, or a salt thereof.
In one further aspect the present invention provides a process for inhibiting
crystallisation of triglyceride in palm olein oil, the process comprising the step of
combining with the palm olein oil, an ester of (i) lactic acid and (ii) a C12 to C22 fatty
acid or a salt thereof.
In one further aspect the present invention provides use of an ester of (i) lactic acid and
(ii) a C12 to C22 fatty acid or a salt thereof for inhibiting crystallisation of triglyceride in
palm olein oil.
The present invention will now be described in further detail by way of example only
with reference to the accompanying figures in which:-
Figure 1 shows a scheme; and
Figures 2 and 3 show samples.
The present invention will now be described in further detail in the following examples.
EXAMPLES
EXAMPLE 1
In the following example sodium stearoyllactylate (GRINDSTED SSL P45 and
GRINDSTED SSL P55) was incorporated into double fractionated 60IV palm olein
cooking oils, both alone and in combination with sorbitan tristearate (GRINDSTED STS
GRINDSTED SSL P45, GRINDSTED SSL P55 and GRINDSTED STS Q are each
available from DuPont (formerly Danisco A/S).
Samples of cooking oil were made as below:
i. a 1% w/w solution of SSL was made up in 60IV palm olein, and held warm
(60°C) until required.
ii. to each test beaker, add the required amount of SSL solution and sufficient
60IV palm olein to enable final net beaker weight of 170g.
iii. place each beaker on a stirrer/hotplate, add required STS and heat to 65°C
with agitation: ensure all SSL and STS is dissolved.
iv. add 145g of each solution to a sample bottle, retaining the balance for
turbidity measurement.
v. transfer sample bottles to 65°C water bath and hold 2 hours.
vi. place samples on bench (22°C) for 90 minutes.
vii. transfer samples to 18°C water bath and monitor visually on a daily basis.
The observer monitored for signs of crystallisation.
Negative controls consisted of pure 60IV palm olein.
Positive controls contained either 0.04, 0.06 or 0.08% w/w GRINDSTED STS Q.
SSL was tested in the range 0.02 – 0.1% w/w either on its own, or in combination with
one of 0.04, 0.06 or 0.08% GRINDSTED STS Q.
The amounts introduced into each of the sample bottles is given in the table below.
Bottle # Sample STS Q g/170g total 1% P55 in
1 0.04 STS Q 0.068 0
2 0.06 STS Q 0.102 0
3 0.08 STS Q 0.136 0
4 0.02P55 + 0.04 STSQ 0.068 3.4
0.04P55 + 0.04 STSQ 0.068 6.8
6 0.08P55 + 0.04 STS Q 0.068 13.6
7 0.1P55 + 0.04 STS Q 0.068 17
8 0.02P55 + 0.06 STSQ 0.102 3.4
9 0.04P55 + 0.06 STSQ 0.102 6.8
0.08P55 + 0.06 STS Q 0.102 13.6
11 0.1P55 + 0.06 STS Q 0.102 17
12 0.02P55 + 0.08 STSQ 0.136 3.4
13 0.04P55 + 0.08 STSQ 0.136 6.8
14 0.08P55 + 0.08STS Q 0.136 13.6
0.1P55 + 0.08 STS Q 0.136 17
16 0.02% P55 0 3.4
17 0.04% P55 0 6.8
18 0.08% P55 0 13.6
19 0.10% P55 0 17
CONTROL 60IV 0 0
Samples of 0.02% SSL by itself, and with SSL + STS were found to resist crystallisation
onset in a superior fashion to untreated palm olein.
Figure 2: cooking oil samples at 107 days.
From left to right:
untreated palm olein (negative control);
0.02% GRINDSTED SSL P55 + 0.06% GRINDSTED STS Q;
0.02% GRINDSTED SSL P45.
Only the untreated olein shows crystallisation (see for example, bottom 1/8th of bottle).
EXAMPLE 2
In the following example sodium stearoyllactylate (GRINDSTED SSL P45,
GRINDSTED SSL P55, and GRINDSTED SSL P86) both alone and in combination with
sorbitan tristearate (GRINDSTED STS Q), was incorporated into (refined bleached
deodorised) fractionated 60IV palm olein cooking oils and into blends of 60IV palm olein
cooking oil and rape seed oil.
Samples of cooking oil were made as below:
1. Heat the oil or oil blend to 60°C for 30 min and mix. Allow to cool to ambient
temperature.
2. Weigh off the anticrystalliser and the oil phase.
3. Place the samples at 90°C for 3 h and mix.
4. Cool the samples to ambient temperature.
5. Place the samples at the test temperatures.
* denotes that the sample showed turbidity prior to crystallisation being observed.
SSL P55 and STS Q
18°C Palm olein Cp 5°C
STS Q
SSL P55 0% 0.02% 0.04% 0.06% 0.08% 0.10% 0.12%
0% 9 12 28 28 12 30 33
0.0050% 13 98 103 98 99 131 103
0.0100% 20 113 110 72 91 119* 132*
0.0150% 32 124 132 125* 142* 121* 161*
0.0200% 106 118 119 97* 105 105* 143*
°C Palm olein Cp 5°C
STS Q
SSL P55 0% 0.02% 0.04% 0.06% 0.08% 0.10%
0% 4 4 10 10 10 16*
0.0020% 4 7 15 13 17 20*
0.0050% 4 16 19 20* 20* 17*
0.0100% 9 17 20 21* 23* 18*
12°C 50:50 Blend (palm olein Cp 5°C : rape seed oil)
STS Q
SSL P55 0% 0.02% 0.04% 0.06% 0.08% 0.10%
0% 7 11 13 13 10 13
0.0020% 6 24 23 19 13 19
0.0050% 7 32 29 29 24* 23*
0.0100% 21 44 35 29 38* 31*
0.0150% n/a 33* 26* 31* 38* 38*
SSL P45 and STS Q
18°C Palm olein Cp 5°C
STS Q
SSL P45 0% 0.02% 0.04% 0.06% 0.08% 0.10% 0.12%
0% 14 34 38 49 64 112 112
0.0050% 17 92 134 >167 118 117 >167
0.0100% 27 140 >167 >167 >167 56* 70*
0.0150% 77 132* 131* >167* 58* 138* >167*
0.0200% 65* 137* >167* >167* >167* >167* >167*
°C Palm olein Cp 5°C
STS Q
SSL P45 0% 0.02% 0.04% 0.06% 0.08% 0.10% 0.12%
0% 5 8 11 17 13* 13* 13*
0.0050% 8 20 29 31 42* 38* 32*
0.0100% 11 41* 36* 45* 37* 66* 32*
0.0150% 14 38* 56* 45* 45* 44* 52*
0.02% 34* 35* 34* 42* 39* 43* 39*
12°C 50:50 Blend (palm olein Cp 5°C (080212-01) : rape
seed oil)
STS Q
SSL P45 0% 0.02% 0.04% 0.06% 0.08% 0.10%
0% 5 9* 19* 23* 19* 19*
0.0020% 5* 14* 14* 13* 23* 21*
0.0050% 6 32 21 23 22* 21*
0.0100% 10 22 41* 35* 41* 12*
0.0150% 22* 25* 30* 26* 34* 38*
SSL P86 and STS Q
°C Palm olein Cp 5°C
STS Q
SSL P86 0% 0.02% 0.04% 0.06% 0.08% 0.10% 0.12%
0% 4 4 6 8 12* 12* 12*
0.0050% 4 9 15 21 28 29* 15
0.0100% 4 20 19 28 27 29* 30*
0.0150% 6 14 32 32 19 28* 27*
0.02% 7 16 17 17 20 18* 18*
18°C Palm olein Cp 5°C
STS Q
SSL P86 0% 0.02% 0.04% 0.06% 0.08% 0.10% 0.12%
0% 5 7 11 13 19 27* 21*
0.0050% 5 12 26 57 39 >112 42
0.0100% 7 >112 92 74 >112 >112 >112
0.0150% 15 53 104 >112 >112 53 >112
0.0200% 21 57 108 75 >112 91 57
12°C 50:50 Blend (palm olein Cp 5°C : rape seed oil)
STS Q
SSL P86 0% 0.02% 0.04% 0.06% 0.08% 0.10%
0% 5 9 9 21* 17* 8*
0.0020% 5 16 19 14 12* 23*
0.0050% 7 33 36 20 17 13*
0.0100% 12 21* 20* 30* 30* 13*
0.015% 24* 27* 33* 30* 30* 50*
EXAMPLE 3
In the following example potassium stearoyllactylate (PSL) both alone and in
combination with sorbitan tristearate (GRINDSTED STS Q), was incorporated into
fractionated 60IV palm olein cooking oil and into a 50:50 blend of 60IV palm olein
cooking and rape seed oil.
The samples of cooking oil were made in accordance with Example 2.
* denotes that the sample showed turbidity prior to crystallisation being observed.
12°C 50:50 Blend (Palm olein Cp 5°C : rape seed oil)
STS Q
PSL 0% 0.02% 0.04% 0.06% 0.08% 0.10%
0% 7 12 21* 21* 20* 20*
0.0020% 10 26 27 25 20* 19*
0.0050% 19 70* 71* 40* 40* 61*
0.0100% 103* >160* 125* 74* 62* 61*
°C Palm olein Cp 5°C
STS Q
PSL 0% 0.02% 0.04% 0.06% 0.08% 0.10%
0% 4 5 6 6 7 7
0.0020% 4 7 9 9 10 10*
0.0050% 4 7 10 10 26* 12*
0.0100% 4 7 18* 10* 10* 5
EXAMPLE 4
In the following example sodium oleyllactylate (SOL) was prepared from approx 34%
lactic acid and based on Palmac 760 (min 75% oleic acid). The sample is denoted SOL.
The SOL was tested both alone and in combination with sorbitan tristearate
(GRINDSTED STS Q) in a 50:50 blend of 60IV palm olein cooking oil and rape seed oil.
The samples of cooking oil were made in accordance with Example 2.
* denotes that the sample showed turbidity prior to crystallisation being observed.
12°C 50:50 Blend (palm olein Cp 5°C (080212-01) : rape
seed oil)
SOL STS Q
0% 0.02% 0.04% 0.06% 0.08% 0.10%
0% 4 8 15 11* 10* 10*
0.0020% 4 8 12 11* 24* 21*
0.0050% 5 15 26 18 12* 28*
0.0100% 6 27 24 25 45 14
0.0150% 6 27 46 26 54* 43*
0.0200% 6 31 41 45 49* 49*
0.0250% 6 34 54 54 50 48
EXAMPLE 5
Samples of cooking oil were made as below:
1. prepare a 2% concentrate of the anticrystallizer by dispersing in the oil blend
and heating until a clear, homogeneous solution is obtained (heat to 75°C and
hold 10 minutes). Typically, depending on the number of samples to be put on,
this comprises either dissolving 1g of anticrystalliser in 49g of oil blend, or 2g of
anticrystalliser in 98g of oil blend
2. dose this concentrate at the required level into the required aliquot of the oil
blend which has been tempered to 30°C and mix for 20 minutes, holding the
mixture at 30°C.
3. Typically this is to produce a 200g total. A 400g tall form beaker is used to hold
this mixture, and it is agitated with an overhead stirrer fitted with a propeller type
impeller.
4. Transfer 150g to a test bottle, and fix the cap.
. transfer to storage temperature (12°C for the work reported herein) and monitor
at regular intervals, ideally daily, for signs of instability. Failure is any significant
loss of
6. clarity, crystallisation, appearance of sediment or formation of flocculant or
curtain like structures within the oil.
7. report result as days to failure.
In the following example sodium stearoyllactylate (SSL), sodium palmitoyl lactylate
(SPL) and potassium stearoyllactylate (PSL), each alone and in combination with
sorbitan tristearate (GRINDSTED STS Q), was incorporated into an oil which was 50:50
blend of canola oil and a palm olein having a diglyceride content of 9.2%. The samples
were tested at 12°C
Bottle Anti % % % % g 1% g 1% Failure How failed
# Cryst. STS SSL PSL SPL STS Q/ SPL/ days
Q 200g 200g
total total
1 0 0 3 crystallisation
2 STS 0.02 0 4 4 turbid
3 STS 0.04 0 8 4 turbid
4 STS 0.06 0 12 4 floc
STS 0.08 0 16 3 floc
6 STS 0.1 0 20 3 floc
7 SPL 0 0.005 1 3 crystallisation
8 SPL 0 0.01 2 3 crystallisation
9 SPL 0 0.015 3 3 crystallisation
SPL 0 0.02 4 4 dusting
11 SPL/STS 0.02 0.005 4 1 4 turbid
12 SPL/STS 0.02 0.01 4 2 10 turbid
13 SPL/STS 0.02 0.015 4 3 31 crystallisation
14 SPL/STS 0.02 0.02 4 4 40 dusting
SPL/STS 0.04 0.005 8 1 4 turbid
16 SPL/STS 0.04 0.01 8 2 6 turbid
17 SPL/STS 0.04 0.015 8 3 20 crystallisation
18 SPL/STS 0.04 0.02 8 4 32 dusting
19 PSL/STS 0.02 0.01 3 21 crystallisation
PSL/STS 0.03 0.015 4.5 40 Dusting
21 PSL/STS 0.04 0.02 6 20 Cloudy
22 PSL/STS 0.05 0.025 7.5 40 Sl. Turbid
23 P55/STS 0.02 0.01 3 10 turbid
24 P55/STS 0.03 0.015 4.5 10 crystallisation
P55/STS 0.04 0.02 6
31 Dusting
26 P55/STS 0.05 0.025 7.5 39 Dusting
27 SPL/STS 0.02 0.01 10 crystallisation
28 SPL/STS 0.03 0.015 17 Dusting
29 SPL/STS 0.04 0.02 40 Dusting
SPL/STS 0.05 0.025 40 Dusting
Bottles 19-22 contain a co-crystallised blend of 2 parts STS Q: 1 part PSL.
Bottles 23-26 contain the co-crystallised blend of 2 parts STS Q: 1 part SSL P55.
Bottles 27-30 contain varying amounts as specified of STS Q and SPL in the ratio 2:1,
added as singles.
EXAMPLE 6
In the following example sodium stearoyllactylate (SSL) was used in combination
with sorbitan tristearate (GRINDSTED STS Q), was incorporated into an oil which was
50:50 blend of canola oil and a palm olein having a diglyceride content of 9.2%. The
samples were tested at 12°C. Samples of STS alone were also tested.
Blend 019 is a blend of 33wt% SSL P55 and 67wt% STS Q. The sample is prepared by
co-crystallisation.
The samples of cooking oil were made in accordance with Example 5 except that the oil
was heated to 70 C in step 1.
5R, 6R and 7R are replicates of 5, 6 and 7 but made up with a palm olein having a
diglyceride content of approximately 7.5%.
Bottle Oil Blend 019 ST S Blend Average How failed
# (% Canola Blend % (g 2% Failure days
/ % 60IV (% w/w) w/w) solution/170 (duplicate
olein) g bottle)* runs)
1 50/50 0 1 flocculation
2 50/50 0.03 2.55 13 dusting
3 50/50 0.045 3.825 17 dusting
4 50/50 0 0.06 0.102 7 flocculation
60/40 0 2 flocculation
6 60/40 0.03 2.55 46
7 60/40 0.045 3.825 35 dusting
8 60/40 0 0.06 0.102 17 flocculation
5R 60/40 0 17 nucleation
6R 60/40 0.03 2.55 30 slight turbidity
7R 60/40 0.045 3.825 31 slight turbidity
9 70/30 0 4 dusting
70/30 0.03 2.55 7 flocculation
11 70/30 0.045 3.825 41 nucleation
12 70/30 0 0.06 0.102 11 flocculation
13 80/20 0 17 haze
14 80/20 0.03 2.55 7 flocculation
80/20 0.045 3.825 22 flocculation
16 80/20 0 0.06 0.102 9 flocculation
EXAMPLE 7
In the following example calcium stearoyllactylate (CSL) was used alone and in
combination with sorbitan tristearate (GRINDSTED STS Q), was incorporated into an oil
which was 50:50 blend of canola oil and a palm olein having a diglyceride content of
9.2%. The samples were tested at 12°C.
The samples of cooking oil were made in accordance with Example 5.
Bottle AntiCryst %ST %CSL g 1% STSQ/ g 1% CSL/ Failure How failed
# . SQ 200 g total 200 g total days
1 0 0 <3 Turbid
2 STS 0.02 0 4 <3 Turbid
3 STS 0.04 0 8 <3 Turbid
4 STS 0.06 0 12 <3 Turbid
STS 0.08 0 16 <3 Turbid
6 STS 0.1 0 20 <3 Turbid
7 CSL 0 0.005 1 <3 Crystallisation
8 CSL 0 0.01 2 <3 Crystallisation
9 CSL 0 0.015 3 <3 Crystallisation
CSL 0 0.02 4 <3 Crystallisation
11 CSL/STS 0.02 0.005 4 1 <3 Turbid
12 CSL/STS 0.02 0.01 4 2 <3 Turbid
13 CSL/STS 0.02 0.015 4 3 <3 Turbid
14 CSL/STS 0.02 0.02 4 4 <3 Turbid
CSL/STS 0.04 0.005 8 1 <3 Turbid
16 CSL/STS 0.04 0.01 8 2 <3 Turbid
17 CSL/STS 0.04 0.015 8 3 <3 Turbid
18 CSL/STS 0.04 0.02 8 4 <3 Turbid
19 CSL/STS 0.02 0.010 4 2 <3 Turbid
CSL/STS 0.03 0.015 6 3 5 Cloudy
21 CSL/STS 0.04 0.020 8 4 <3 Turbid
22 CSL/STS 0.05 0.025 10 5 <3 Turbid
EXAMPLE 8
In the following example sodium stearoyllactylate (SSL) was used alone and was
incorporated into an oil which was a 30:70 blend of palm olein cooking oil (CP 5 C) and
rape seed oil. The mix was subjected to a very stringent test of being cooled to 0 C,
Procedure
1. Heat oil blend with emulsifiers to 130°C (cabinet 200°C).
2. Filter (Whatmann 115).
3. Fill 225 g in suitable blue cap bottle.
4. Cool to 25°C in water bath.
5. Place samples in ice water and inspect for turbidity and crystallisation for 5.5 h.
Time h Ref 0.005% 0.010%
SSL P 55 SSL P 55
0.5 Clear Clear clear
1 slightly turbid Clear clear
1.5 Clear clear
2 slightly turbid slightly turbid clear
2.5 Turbid clear
3 Turbid very turbid clear
4 very turbid very turbid clear
4.5 very turbid clear
very very turbid clear
.5 starts to solidify very very turbid clear
EXAMPLE 9
In the following example sodium stearoyllactylate (SSL P55) was used in
combination with sorbitan tristearate (GRINDSTED STS Q) and was incorporated into
an oil which was 40:60 blend of palm olein have a cloud point of 5 C and rape seed oil.
The mix was subjected to the very stringent procedure of Example 8, being cooled to
0 C.
The data are given below and the samples are shown in Figure 3. As can be seen in
Figure 3, the difference between samples 2 to 7 is small, but sample 5 is the best. The
hazy appearance on bottles 2-7 is due to water condensation.
Oil blend 30:70 - palm olein CP 5°C: rape seed oil
1 2 3 4 5 6 7 8
SSL P55 % 0 0.01 0.01 0.01 0.01 0.01 0.01 0.01
STS Q % 0 0 0.0001 0.0005 0.0011 0.0033 0.001 0.002
Time (h)
0.5 Clear Clear Clear Clear Clear Clear Clear Clear
1 Clear Clear Clear Clear Clear Clear Clear Turbid
1.5 Clear Clear Clear Clear Clear Clear Clear Very turbid
2 Slightly turbid Clear Clear Clear Clear Clear Clear Very turbid
2.5 Turbid Clear Clear Clear Clear Clear Clear Very, very
turbid
3 Very turbid Clear, but Clear Clear, but Clear Clear Clear Very, very
clouds locally clouds locally turbid
3.5 Very turbid Clear, but Clear, but Clear, but Clear Clear Clear Very, very
clouds locally clouds locally clouds locally turbid
4 Very turbid Clear, but Clear, but Clear, but Clear Clear, but Clear, but Pasty
clouds locally clouds locally clouds locally some crystals some crystals
in upper half in upper half
4.5 Very turbid Clear, but Clear, but Clear, but Clear, but few Clear, but Slightly turbid Nearly solid
clouds locally clouds locally clouds locally crystals in top some crystals with crystals
in upper half
Very turbid Clear, but Clear, but Clear, but Clear, but few Clear, but Slightly turbid Solid
clouds locally clouds locally clouds locally crystals in top some crystals with crystals
in upper half
.5 Very turbid Clear, but Clear, but Clear, but Clear, but few Clear, but A good deal Solid
clouds locally clouds locally clouds locally crystals in top some crystals of crystals
in upper half
Oil mix - 40% Palm olein CP 5°C and 60% Rape seed oil
Time (h) Reference 0,005% SSL P55 0.001% SSL P55
0.5 Clear Clear Clear
1 Very turbid Very turbid Very, very turbid
2 Very, very turbid Very, very turbid Very, very turbid
3 Nearly solid Nearly solid Nearly solid
4 Solid Solid Solid
.5 Solid Solid Solid
REFERENCE EXAMPLE 10
In the following example sodium stearyl fumarate (SSF) (available from A&Z Food
Additives Co. Ltd, China and having a purity > 99%) was used in combination with
sorbitan tristearate (GRINDSTED STS Q) and was incorporated into an oil which was
50:50 blend of palm olein having a cloud point of 5 C and rape seed oil. The samples
were tested at 12°C
Procedure:
After weighing out the emulsifiers and oil blends the mixes were heated together to
90°C for 3 hours in closed blue cap bottles followed by gentle shaking of the bottles.
The samples were allowed to cool to ambient temperature and subsequently stored at
the test temperature. The samples were inspected daily for appearance and
crystallisation.
STS Q
SSF 0% 0.02% 0.04%
0% 4 6 13
0.0020% 4* 7* 15*
0.0050% 4* 6* 14*
0.0100% 4* 13* 20*
0.0200% 4* 9* 14*
* all samples with SSF did not dissolve completely during sample preparation.
The un-dissolved SSF formed a thin dusty layer at the bottom during storage
A synergistic anticrystalliser effect is seen at 0.01% SSF + 0.04% STS Q as compared
to addition of STS Q alone. SSF has very low solubility in oil, which causes the initial
precipitation.
EXAMPLE 11
In the following example potassium stearoyl lactylate (PSL) was used in combination
with sorbitan tristearate (GRINDSTED STS Q) and was incorporated into an oil which
was 50:50 blend of palm olein have a cloud point of 5 C and rape seed oil. The samples
were tested at 12°C and 15°C
Procedure:
The samples were prepared in the same manner as Reference Example 10.
STS Q
PSL 2671/051 0% 0.02% 0.04% 0.06% 0.08%
0% 7 12 7 7 7
0.0020% 10 26 27 25 4
0.0050% 19 21 21 4 4
0.0100% 4 4 4 4 4
PSL at 12°C shows effect as anticrystalliser in cooking oil in combination with STS and
as single ingredient.
As for SSL high concentration of either PSL or STS causes turbidity or clouding.
STS Q
PSL 2671/051 0% 0.02% 0.04% 0.06% 0.08% 0.10%
0% 4 5 6 6 7 7
0.0020% 4 7 9 9 10 3
0.0050% 4 7 10 10 3 3
0.0100% 4 7 3 3 3 5
EXAMPLE 12
In the following example sodium lauroyl lactylate (SLL) was used in combination with
sorbitan tristearate (GRINDSTED STS Q) and was incorporated into an oil which was
50:50 blend of palm olein have a cloud point of 5 C and rape seed oil. The samples
were tested at 12°C.
Procedure:
The samples were prepared in the same manner as Reference Example 10.
STS Q
SLL 0% 0.02% 0.04%
0% 3 7 6
0.0020% 3 15 19
0.0050% 5 14 6
0.0100% 9 32 >35
0.0200% 11 >35 >35
A clear effect is seen with SLL added as single ingredient as well as together with STS
Q. The optimal dosage range is slightly higher than for SSL.
EXAMPLE 13
In the following example sodium behenoyl lactylate (SBL) was used in combination with
sorbitan tristearate (GRINDSTED STS Q) and was incorporated into an oil which was
50:50 blend of palm olein have a cloud point of 5 C and rape seed oil. The samples
were tested at 12°C.
Procedure:
The samples were prepared in the same manner as Reference Example 10.
STS Q
SBL 0% 0.02% 0.04%
0% 3 7 6
0.0020% 3 7 12
0.0050% 7 19 22
0.0100% 9 >35 >35
0.0200% 9 6 6
A clear effect is seen with SBL added as single ingredient as well as together with STS
Q. Optimal dosage range as for SSL/STS combinations.
EXAMPLE 14
In the following example different blends of sodium stearoyllactylate (SSL) and
sodium palmitoyl lactylate (SPL) was used in combination with sorbitan tristearate
(GRINDSTED STS Q) and was incorporated into an oil which was 50:50 blend of palm
olein have a cloud point of 5 C and rape seed oil. The samples were tested at 12°C.
Procedure:
The samples were prepared in the same manner as Reference Example 10.
SPL:SSL Amount of STS Q
ratio blend 0% 0.02% 0.04%
0.0000% 3 8 18
100:0 0.0020% 3 8 19
100:0 0.0050% 5 19 11
100:0 0.0100% 12 17 9
STS Q
SPL:SSL Amount of
ratio blend 0% 0.02% 0.04%
0.0000% 3 8 18
75:25 0.0020% 4 11 22
75:25 0.0050% 7 17 10
75:25 0.0100% 13 17 17
SPL:SSL Amount of STS Q
ratio blend 0% 0.02% 0.04%
0.0000% 3 8 18
50:50 0.0020% 3 10 20
50:50 0.0050% 5 20 20
50:50 0.0100% 18 7 6
STS Q
SPL:SSL Amount of
ratio blend 0% 0.02% 0.04%
0% 7 11 13
:70 0.0020% 6 24 23
:70 0.0050% 7 32 29
:70 0.0100% 21 44 35
SPL:SSL Amount of STS Q
ratio blend 0% 0.02% 0.04%
0.0000% 3 8 18
:75 0.0020% 4 10 30
:75 0.0050% 6 14 10
:75 0.0100% 11 7 5
SPL:SSL Amount of STS Q
ratio blend 0% 0.02% 0.04%
0.0000% 3 8 18
0:100 0.0020% 5 9 11
0:100 0.0050% 7 32 13
0:100 0.0100% 15 6 4
A further subtrial was performed using a 100% palm olein with better cold stability
properties.
Best results are seen with a fatty acid composition with at least 50% by weight of C18
based on the total amount of fatty acids. However for the 50:50 blends the two samples
marked † were actually much better than the results indicate. A few crystals appeared
after 20 days, but no more crystallisation is seen even after 34 days. This means the
best range for the fatty acid composition is from 50% C18 and up including 50% in the
range.
EXAMPLE 15
In the following example sodium oleoyl lactylate (SOL) was used in combination with
sorbitan tristearate (GRINDSTED STS Q) and was incorporated into an oil which was
50:50 blend of palm olein having a cloud point of 5 C and rape seed oil. The samples
were tested at 12°C.
Procedure:
The samples were prepared in the same manner as Reference Example 10.
STS Q
SOL (2440/207) 0% 0.02% 0.04% 0.06%
0% 4 8 15 11
0.0020% 4 8 12 11
0.0050% 5 15 26 18
0.0100% 6 27 24 25
0.0150% 6 27 46 26
0.0200% 6 31 41 45
0.0250% 6 34 54 54
2440/207: approx 34% lactic acid and based on Palmac 760 fatty acids (min 75% oleic
acid).
SOL is very effective in combination with STS Q with optimal dosage range 0.015-
0.025% for SOL and for STS Q in the range 0.04-0.06%. Note that SOL requires slightly
higher dosage than SSL when combined with STS Q.
EXAMPLE 16
In the following example SSL was incorporated into an oil which was 30:70 blend of
palm olein having a cloud point of 5 C and rape seed oil. The test was performed as
follows:
Procedure:
Heat oil blend with emulsifiers to 130°C (cabinet 200°C).
Filter (Whatmann filter paper 115).
Fill 225 g in suitable blue cap bottle.
Cool to 25°C in water bath.
Place samples in ice water and inspect for turbidity and crystallisation for 5.5 h.
SSL P 55
Time h 0.0010% 0.005% 0.010%
0.5 clear Clear clear
1 clear Clear clear
1.5 slightly turbid Clear clear
2 turbid slightly turbid clear
2.5 turbid Turbid clear
3 very turbid very turbid clear
4 very turbid very turbid clear
4.5 very turbid very turbid clear
pasty (more than 0.005%) very very turbid clear
.5 pasty (more than 0.005%) very very turbid clear
EXAMPLE 17
Experimental procedure
1% (concentrate) solutions of both GRINDSTED STS Q and SSL (sample 1830/107)
were prepared by weighing the required amount of emulsifier and adding to the oil blend
under agitation. The mixture was heated to 70°C by which time the emulsifiers had
dissolved yielding a homogeneous, clear solution of each emulsifier. These solutions
were held warm to maintain them as solutions.
To prepare each test sample, the required mass of emulsifier concentrate was added
into a beaker, and oil blend added to make a 200g total. The mixture was heated to
70°C, producing a clear solution.
150g of the solution was transferred to a test bottle (200mL "McCarthy" bottle), and the
bottle capped and labelled.
Once all test bottles had been prepared they were transferred to a 75°C water bath and
held for 2 hours. The bottles were then transferred to the lab bench at room
temperature for 90 minutes following which they were transferred to a 12°C water bath.
Samples were observed daily and failure date recorded.
Results
Bottle # Anti Cryst. % STS Q % 1830/107 Failure days How failed
1 0 0 1 Dusting
2 STS 0.02 0 4 Crystallisation
3 STS 0.04 0 6 Sl. Turbid
4 STS 0.06 0 1 Cloudy
STS 0.08 0 1 Cloudy
6 STS 0.1 0 1 Cloudy
8 1830/107 0 0.01 1 Dusting
9 1830/107 0 0.015 1 Dusting
1830/107 0 0.02 4 Crystallisation
11 1830/107 0 0.025 12 Crystallisation
12 1830/107 0 0.03 19 Crystallisation
13 1830/107 / STS 0.02 0.01 8 Nucleation
14 1830/107 / STS 0.02 0.015 13 Crystallisation
1830/107 / STS 0.02 0.02 42 Crystallisation
16 1830/107 / STS 0.02 0.025 >57
17 1830/107 / STS 0.02 0.03 > 57
18 1830/107 / STS 0.04 0.01 15 Crystallisation
19 1830/107 / STS 0.04 0.015 42 Crystallisation
1830/107 / STS 0.04 0.02 35 Crystallisation
21 1830/107 / STS 0.04 0.025 39 Crystallisation
22 1830/107 / STS 0.04 0.03 1 Crystallisation
23 1830/107 / STS 0.06 0.01 1 Cloudy
24 1830/107 / STS 0.06 0.015 7 Sl. Cloud
1830/107 / STS 0.06 0.02 25 Dusting
26 1830/107 / STS 0.06 0.025 25 Dusting
27 1830/107 / STS 0.06 0.03 >57
28 1830/107 / STS 0.08 0.01 1 Cloudy
29 1830/107 / STS 0.08 0.015 4 Cloudy
Bottle # Anti Cryst. % STS Q % 1830/107 Failure days How failed
1830/107 / STS 0.08 0.02 41
31 1830/107 / STS 0.08 0.025 29 Cloudy
32 1830/107 / STS 0.08 0.03 55 Cloudy
33 1830/107 / STS 0.1 0.01 1 Cloudy
34 1830/107 / STS 0.1 0.015 1 Cloudy
1830/107 / STS 0.1 0.02 6 Sl. Turbid
36 1830/107 / STS 0.1 0.025 1 Crystallisation
37 1830/107 / STS 0.1 0.03 26 Clouding
Conclusion
40% lactic acid SSL was found to have an effect in its own right, particularly at
concentrations >0.02%. It was superior to STS by itself, which had a maximum
performance of 6 days in this experiment.
The combination demonstrated a synergy of effect, with several combinations providing
clarity for >57 days.
EXAMPLE 18
In the following example sodium stearoyllactylate (GRINDSTED SSL P55) alone and
in combination with a polyglycerol ester (PGE) was incorporated into a 50:50 blend of
palm olein cooking and rape seed oil.
The PGE was a decaglycerol ester in which >95% of all hydroxyl groups are esterified,
the predominant fatty acid component is C16. The PGE has an acid value of <10 mg
KOH/g and a hydroxyl value of <12 mg KOH/g.
The samples of cooking oil were made in accordance with Example 2.
12°C 50:50 Blend (palm olein Cp 5°C : rape
seed oil)
SSL P55 PGE
0% 0.04% 0.06% 0.08% 0.10%
0% 3 17& 17& 18& 18&
0.0020% 3 12 12 18† 32
0.0050% 5 28 58 58 >76
0.0100% 10 45 31 >76 >76
& denotes that the sample showed clouding after 6 days.
† denotes that the sample showed clouding after 15 days.
All publications mentioned in the above specification are herein incorporated by
reference. Various modifications and variations of the described methods and system of
the invention will be apparent to those skilled in the art without departing from the scope
and spirit of the invention. Although the invention has been described in connection with
specific preferred embodiments, it should be understood that the invention as claimed
should not be unduly limited to such specific embodiments. Indeed, various
modifications of the described modes for carrying out the invention which are obvious to
those skilled in chemistry or related fields are intended to be within the scope of the
following claims.
Where the terms “comprise”, “comprises”, “comprised” or “comprising” are used in this
specification, they are to be interpreted as specifying the presence of the stated
features, integers, steps or components referred to, but not to preclude the presence or
addition of one or more other feature, integer, step, component or group thereof.
Claims (37)
1. A palm olein composition comprising: (a) palm olein oil 5 (b) a lactic acid ester selected from an ester of lactic acid and a C12 to C22 fatty acid, salts thereof and mixtures thereof.
2. A palm olein composition according to claim 1 wherein the fatty acid is a C16 to C22 fatty acid.
3. A palm olein composition according to any one of the preceding claims wherein the fatty acid is a C18 to C22 fatty acid.
4. A palm olein composition according to any one of the preceding claims wherein the 15 fatty acid is a C18 fatty acid.
5. A palm olein composition according to any one of the preceding claims wherein the fatty acid is a mixture of C16 and C18 fatty acid. 20
6. A palm olein composition according to any one of the preceding claims wherein the fatty acid is a saturated fatty acid.
7. A palm olein composition according to any one of the preceding claims wherein the fatty acid is palmitic acid, stearic acid or a mixture thereof.
8. A palm olein composition according to claim 4 wherein the fatty acid is at least stearic acid.
9. A palm olein composition according to any one of the preceding claims wherein the 30 lactic acid ester is in the form of a sodium, calcium or potassium salt thereof.
10. A palm olein composition according to any one of the preceding claims wherein the lactic acid ester is in the form of a sodium salt thereof. 35
11. A palm olein composition according to any one of the preceding claims wherein (b) is sodium stearoyl lactylate.
12. A palm olein composition according to any one of the preceding claims wherein the palm olein is double fractionated.
13. A palm olein composition according to any one of the preceding claims wherein the lactic acid ester is present in an amount of at least 0.001 wt% based on the weight of palm olein oil. 10
14. A palm olein composition according to any one of the preceding claims wherein the lactic acid ester is present in an amount of at least 0.005 wt% based on the weight of palm olein oil.
15. A palm olein composition according to any one of the preceding claims wherein the 15 lactic acid ester is present in an amount of at least 0.01 wt% based on the weight of palm olein oil.
16. A palm olein composition according to any one of claims 1 to 8 wherein the lactic acid ester is present in an amount of no greater than 0.1 wt% based on the weight of 20 palm olein oil.
17. A palm olein composition according to any one of claims 1 to 8 wherein the lactic acid ester is present in an amount of no greater than 0.04 wt% based on the weight of palm olein oil.
18. A palm olein composition according to any one of claims 1 to 8 wherein the lactic acid ester is present in an amount of no greater than 0.02 wt% based on the weight of palm olein oil. 30
19. A palm olein composition according to any one of the preceding claims wherein the composition further comprises (c) sorbitan tristearate.
20. A palm olein composition according to claim 19 wherein the sorbitan tristearate is 35 present in an amount of at least 0.01 wt% based on the weight of palm olein oil.
21. A palm olein composition according to claim 19 wherein the sorbitan tristearate is present in an amount of at least 0.04 wt% based on the weight of palm olein oil. 5
22. A palm olein composition according to claim 19 wherein the sorbitan tristearate is present in an amount of at least 0.06 wt% based on the weight of palm olein oil.
23. A palm olein composition according to claim 19 wherein the sorbitan tristearate is present in an amount of at least 0.08 wt% based on the weight of palm olein oil.
24. A palm olein composition according to any one of the preceding claims wherein the composition further comprises a polyglycerol ester
25. A palm olein composition according to any one of the preceding claims wherein the 15 composition further comprises (d) a second oil.
26. A palm olein composition according to claim 25 wherein the second oil is selected from the group consisting of moringa oil, soy oil, cottonseed oil, canola oil, rapeseed oil 20 (including high oleic rapeseed oil, that is rapeseed oil containing at least 82% oleic acid based on the total weight of fatty acids and including low erucic acid rapeseed oil or high erucic acid rapeseed oil), peanut oil, rice bran oil (including dewaxed rice bran oil), corn oil, safflower oil, sunflower oil (including high oleic sunflower oil, that is sunflower oil containing at least 82% oleic acid based on the total weight of fatty acids), linseed 25 oil, olive oil, peanut oil and mixtures thereof.
27. A process for inhibiting crystallisation of triglyceride in palm olein oil, the process comprising the step of combining with the palm olein oil, a lactic acid ester selected from an ester of lactic acid and a C12 to C22 fatty acid, salts thereof and mixtures 30 thereof.
28. A process according to claim 27 wherein the crystallisation of triglyceride in palm olein oil is inhibited during storage of the palm olein oil at a temperature of less than 25 C.
29. A process according to claim 27 wherein the crystallisation of triglyceride in palm olein oil is inhibited during storage of the palm olein oil at a temperature of less than 15 C. 5
30. A process according to any one of claims 27 to 29 wherein the palm olein oil with which the lactic acid ester is mixed is deodorised palm olein oil or refined palm olein oil.
31. A process according to any one of claims 27 to 30 characterised by the features of any one of claims 2 to 26.
32. Use of a lactic acid ester selected from an ester of lactic acid and a C12 to C22 fatty acid, salts thereof and mixtures thereof, for inhibiting crystallisation of triglyceride in palm olein oil. 15
33. Use according to claim 32 characterised by the features of any one of claims 2 to
34. Use according to claim 32 or 33 wherein nucleation of the triglyceride such that it crystallises is inhibited.
35. A palm olein composition according to claim 1 as substantially hereinbefore described.
36. A process according to claim 27 as substantially hereinbefore described.
37. A use according to claim 32 as substantially hereinbefore described.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1112729.7 | 2011-07-25 | ||
GBGB1112729.7A GB201112729D0 (en) | 2011-07-25 | 2011-07-25 | Composition |
GBGB1208992.6A GB201208992D0 (en) | 2012-05-22 | 2012-05-22 | Composition |
GB1208992.6 | 2012-05-22 | ||
PCT/IB2012/053787 WO2013014622A1 (en) | 2011-07-25 | 2012-07-25 | Palm olein oil composition |
Publications (2)
Publication Number | Publication Date |
---|---|
NZ619374A NZ619374A (en) | 2015-05-29 |
NZ619374B2 true NZ619374B2 (en) | 2015-09-01 |
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