WO2009024475A1 - Coated benzoic acid or benzoate salt - Google Patents

Coated benzoic acid or benzoate salt Download PDF

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Publication number
WO2009024475A1
WO2009024475A1 PCT/EP2008/060401 EP2008060401W WO2009024475A1 WO 2009024475 A1 WO2009024475 A1 WO 2009024475A1 EP 2008060401 W EP2008060401 W EP 2008060401W WO 2009024475 A1 WO2009024475 A1 WO 2009024475A1
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Prior art keywords
benzoic acid
salt
composition
particles
coated
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Application number
PCT/EP2008/060401
Other languages
French (fr)
Inventor
Richard Johannes Matheus Janssen
Original Assignee
Dsm Ip Assets B.V.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
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Publication of WO2009024475A1 publication Critical patent/WO2009024475A1/en

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/111—Aromatic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K40/00—Shaping or working-up of animal feeding-stuffs
    • A23K40/30—Shaping or working-up of animal feeding-stuffs by encapsulating; by coating
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
    • A23P10/00—Shaping or working of foodstuffs characterised by the products
    • A23P10/30—Encapsulation of particles, e.g. foodstuff additives
    • A23P10/35—Encapsulation of particles, e.g. foodstuff additives with oils, lipids, monoglycerides or diglycerides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
    • A23P10/00—Shaping or working of foodstuffs characterised by the products
    • A23P10/40—Shaping or working of foodstuffs characterised by the products free-flowing powder or instant powder, i.e. powder which is reconstituted rapidly when liquid is added
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
    • A23P10/00—Shaping or working of foodstuffs characterised by the products
    • A23P10/40—Shaping or working of foodstuffs characterised by the products free-flowing powder or instant powder, i.e. powder which is reconstituted rapidly when liquid is added
    • A23P10/47—Shaping or working of foodstuffs characterised by the products free-flowing powder or instant powder, i.e. powder which is reconstituted rapidly when liquid is added using additives, e.g. emulsifiers, wetting agents or dust-binding agents

Definitions

  • the present invention relates to coated composition containing flakes of benzoic acid or a salt thereof, to a method for the preparation of such coated composition, and to methods for the improvement of the flowability and impairment of caking of compositions containing flakes of benzoic acid or a salt thereof as well to a method for the reduction of dust in the handling of compositions containing flakes of benzoic acid or a salt thereof.
  • Coated particles of an organic agent such as benzoic acid for use in food or feed are known from US patent No. 5,008,1 18.
  • the organic agent is coated by contacting a powder of the organic agent with a powder of lipid having a melting point not lower than 40 0 C by a process which comprises mixing of the two powders and subsequent agitation of the mixture causing melting of the lipid powder due to friction heat whereby the organic agent is coated with the lipid.
  • processes are known, whereby the particles of an organic agent are coated by dispersion or suspension in a melted coating component at elevated temperature and subsequent spraying and cooling of the coated particles of the organic agent.
  • the aim of such coating of particles generally is e.g. to protect the organic agent from contact with air or moisture or to mask undesired odors of the organic agent.
  • compositions of flakes of benzoic acid show a very heterogeneous size distribution of the particles.
  • flake particles of benzoic acid or benzoate salt have an irregular shape with a tendency to erode readily. According to the present invention it has surprisingly been found that compositions containing flakes of benzoic acid or benzoate salt can be successfully coated, thereby resulting in a composition with less formation of dust, with an adequate reduction of the odor of the material, with less sensitivity for moisture and particularly with less tendency of caking and hence better flowability as compared to the non-coated material.
  • a coated composition containing benzoic acid or a salt thereof comprising flake particles of benzoic acid or a salt thereof provided with an outer layer of a hydrocarbon composition, wherein the hydrocarbon composition has a slip melting point below 4O 0 C.
  • a coated composition containing flakes of benzoic acid or a salt thereof can be prepared by contacting a powder containing flakes of benzoic acid or a salt thereof with a liquid hydrocarbon composition having a slip melting point below about 4O 0 C and mixing these components under conditions suitable to essentially maintain the particulate nature of the composition.
  • the flowability of a composition containing flakes of benzoic acid or a salt thereof can be improved by contacting a powder containing flakes of benzoic acid or a salt thereof with a liquid hydrocarbon composition having a slip melting point below about 4O 0 C and mixing these components under conditions suitable to essentially maintain the particulate nature of the composition.
  • the caking of particles of a composition containing flakes of benzoic acid or a salt thereof can be impaired by contacting a powder containing flakes of benzoic acid or a salt thereof with a liquid hydrocarbon composition having a slip melting point below about 4O 0 C and mixing these components under conditions suitable to essentially maintain the particulate nature of the composition.
  • the development of dust during the handling of a composition containing flakes of benzoic acid or a salt thereof can be reduced by contacting a powder containing flakes of benzoic acid or a salt thereof with a liquid hydrocarbon composition having a slip melting point below about 4O 0 C and mixing these components under conditions suitable to essentially maintain the particulate nature of the composition.
  • hydrocarbon composition a composition containing at least one constituent selected from the group consisting of a natural oil, a vegetable oil, a mineral oil, a synthetic oil, a fatty alcohol, a bi-functional alcohol and a tri-functional alcohol.
  • the composition may also contain fats or waxes which in isolation would have a slip melting point higher than about 4O 0 C, but wherein the composition as a whole has a slip melting point below about 4O 0 C.
  • slip melting point is meant here the temperature at which the amount of solid phase in the melting hydrocarbon composition has become so low that an air bubble is forced upwards in an open capillary filled with the hydrocarbon composition.
  • Salts of benzoic acid acceptable for use in food or feed are for example calcium, potassium, ammonium or sodium salts.
  • the composition contains flakes of benzoic acid or salt thereof.
  • a flake is meant here a body of solid benzoic acid or benzoate salt having an irregular shape comprising two essentially flat and parallel surfaces with about equal Feret's diameters along the two axes of the surfaces (Feret x and Feret y ) and wherein the distance between the surfaces has a much smaller Feret's diameter (Feret z ).
  • Essentially parallel means that the flat surfaces may have an angle with respect to each other of not more than about 10°.
  • a Feret's diameter is the distance between two tangents on opposite sides of a particle.
  • the ratio between Feret m ⁇ n (the smallest value of Feret z of the particle) and Feret max (the largest value of Feret x or Feret y of the same particle) is referred to here as the aspect ratio (AR).
  • the flakes of benzoic acid or benzoate salt typically have an AR of between 0.01 and 0.2.
  • the compositions of benzoic acid or benzoate salt preferably contain at least 10 % w/w of flakes, more preferably at least 20% w/w of flakes, and further contain flake fragments.
  • the flakes have Feret max of at least 500 ⁇ m, preferably at least 1000 ⁇ m, more preferably at least 2000 ⁇ m.
  • the Feret's diameter can be measured e.g. microscopically or using the Sympatec Qicpic, a dynamic image analysis system using the Sympatec Gradis dispersion technique. This latter equipment is provided by Sympatec, Am Pulverhaus 1 , D-38678 Clausthal-Zellerfeld, Germany. In the Sympatec Gradis the particles are accelerated in a fail shaft by the gravity of earlh.
  • Sympatec Qicpic is an image analysis sensor, which combines particle size and shape analysis. It uses an exposure time of less than 1 ns, which provides images of particles with a speed of up to 100 m/s. More -A-
  • Benzoic acid or benzoate salt flakes have the tendency to erode easily during handling, i.e. the sharp edges of the flakes may easily brake upon contact between the flake particles or of flake particles with other solid materials. It was expected that this also would be the case with coated flakes and that this would give rise to partial loss of the coating (which would lead to hygroscopic behavior of the particles, such as caking) and/or to generation of smaller dust-forming particles.
  • the dosage of the hydrocarbon substance to benzoic acid or a salt thereof is between 0.05 and 10 mass %.
  • the coated benzoic acid or salt thereof according to the present invention may be used as a constituent of food or feed e.g. to reduce the emission of ammonia in the excrements animals.
  • the present invention also relates to food or feed compositions comprising coated particles as described herein. Furthermore, the present invention relates to premixes for use in the preparation of food or feed compositions, wherein the premixes comprise coated particles as described herein.
  • the coating of the particulate benzoic acid or salt thereof can be carried out for example by adding the coating composition drop-wise into a rotating drum or any other type of mixing device containing flakes of benzoic acid or a slat thereof
  • composition containing flakes of benzoic acid or salt thereof can also be spray coated.
  • the coating composition is sprayed onto said composition of benzoic acid or salt thereof by means of a nozzle. This can be done in a rotating drum or any other type of mixing device.
  • the caking test is done as follows: a cylindrical sample holder is filled with 100-200 g of material.
  • the sample holder is made of a flexible rubber membrane; the sample holder is closed with a lid that is attached to the flexible membrane; the sample holder is put upside down and placed in a pressure chamber; because of the flexible membrane pressure can be applied on the sample by applying an overpressure in the chamber: the sample is consolidated; - an overpressure of 1 bar is used; the sample is stored at room temperature during 1 day; after storage the caked samples are broken by means of a tensile/consolidating bench. This is done by lowering a piston on the sample holder and recording the stress needed to break the sample. The maximum value recorded is the caking tendency expressed in bar (i.e. the maximum force divided by the top surface of the sample holder with a diameter of 40 mm).
  • the value for a reasonable caking tendency is below 0.8 bar, preferably below 0.5 bar and most preferably below 0.25 bar.
  • the principle of the small bag caking test consists of placing small bags with about 200 g of material under a consolidation load (-15 kPa) and store them for 14 days at room temperature. After storage the weight percentage of lumps in the bag is measured. This is a measure for the caking tendency of the material.
  • Soy oil was heated to 80 0 C and was added drop wise to 1500 g of benzoic acid flakes that were kept moving in a rotating drum (35 rpm, diameter 25 cm, length 15 cm) at room temperature. The total rotating of the benzoic acid flakes in the drum took about 3 minutes.
  • Dust consists of small particles and can be measured by quantifying the fraction of particles smaller than 0.5 mm.
  • Quantification of the fraction smaller than 0.5 mm particles is measured by sieving with a 0.5 mm sieve on a Retsch sieve machine type AS 200 control "g".
  • the amplitude setting is 1 mm, the sieving time 1 minute and about 50 gram of material is sieved at one time. In total about 300 grams of material has been sieved.

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Zoology (AREA)
  • Animal Husbandry (AREA)
  • Health & Medical Sciences (AREA)
  • Biophysics (AREA)
  • Molecular Biology (AREA)
  • Fodder In General (AREA)

Abstract

The present invention relates to coated particles of benzoic acid or a salt thereof for use in food or feed, to a method for the preparation of such particles, and to methods for the improvement of the flowability and impairment of caking of particles of an organic agent as well as to a method for the reduction of dust in the handling of particles of an organic agent. To this end a coated particle comprises a flakes of benzoic acid or a salt thereof and an outer layer of a hydrocarbon composition wherein the hydrocarbon composition has a melting point below about 40°C. The present invention also relates to the use of these coated particles in food or feed and to food or feed compositions containing these coated particles.

Description

COATED BENZOIC ACID OR BENZOATE SALT
The present invention relates to coated composition containing flakes of benzoic acid or a salt thereof, to a method for the preparation of such coated composition, and to methods for the improvement of the flowability and impairment of caking of compositions containing flakes of benzoic acid or a salt thereof as well to a method for the reduction of dust in the handling of compositions containing flakes of benzoic acid or a salt thereof. Coated particles of an organic agent such as benzoic acid for use in food or feed are known from US patent No. 5,008,1 18. According to this publication, the organic agent is coated by contacting a powder of the organic agent with a powder of lipid having a melting point not lower than 400C by a process which comprises mixing of the two powders and subsequent agitation of the mixture causing melting of the lipid powder due to friction heat whereby the organic agent is coated with the lipid. Furthermore, processes are known, whereby the particles of an organic agent are coated by dispersion or suspension in a melted coating component at elevated temperature and subsequent spraying and cooling of the coated particles of the organic agent. The aim of such coating of particles generally is e.g. to protect the organic agent from contact with air or moisture or to mask undesired odors of the organic agent.
In the handling of particles of organic agents also other particles problems arise, such as interactions between the particles leading to clumping, also known as caking, or even low flowability of the particles, or the development of dust during the handling.
The known processes generally relate to the coating of particles with a relatively uniform distribution of size. However, compositions of flakes of benzoic acid show a very heterogeneous size distribution of the particles. Furthermore, flake particles of benzoic acid or benzoate salt have an irregular shape with a tendency to erode readily. According to the present invention it has surprisingly been found that compositions containing flakes of benzoic acid or benzoate salt can be successfully coated, thereby resulting in a composition with less formation of dust, with an adequate reduction of the odor of the material, with less sensitivity for moisture and particularly with less tendency of caking and hence better flowability as compared to the non-coated material. According to a first embodiment of the present invention a coated composition containing benzoic acid or a salt thereof is provided comprising flake particles of benzoic acid or a salt thereof provided with an outer layer of a hydrocarbon composition, wherein the hydrocarbon composition has a slip melting point below 4O0C.
According to a further embodiment of the present invention a coated composition containing flakes of benzoic acid or a salt thereof can be prepared by contacting a powder containing flakes of benzoic acid or a salt thereof with a liquid hydrocarbon composition having a slip melting point below about 4O0C and mixing these components under conditions suitable to essentially maintain the particulate nature of the composition.
According to a further embodiment of the present invention the flowability of a composition containing flakes of benzoic acid or a salt thereof can be improved by contacting a powder containing flakes of benzoic acid or a salt thereof with a liquid hydrocarbon composition having a slip melting point below about 4O0C and mixing these components under conditions suitable to essentially maintain the particulate nature of the composition.
According to a further embodiment of the present invention the caking of particles of a composition containing flakes of benzoic acid or a salt thereof can be impaired by contacting a powder containing flakes of benzoic acid or a salt thereof with a liquid hydrocarbon composition having a slip melting point below about 4O0C and mixing these components under conditions suitable to essentially maintain the particulate nature of the composition. According to a further embodiment of the present invention the development of dust during the handling of a composition containing flakes of benzoic acid or a salt thereof can be reduced by contacting a powder containing flakes of benzoic acid or a salt thereof with a liquid hydrocarbon composition having a slip melting point below about 4O0C and mixing these components under conditions suitable to essentially maintain the particulate nature of the composition.
With a "hydrocarbon composition" according to the present invention is meant here a composition containing at least one constituent selected from the group consisting of a natural oil, a vegetable oil, a mineral oil, a synthetic oil, a fatty alcohol, a bi-functional alcohol and a tri-functional alcohol. Next to any of the above constituents, the composition may also contain fats or waxes which in isolation would have a slip melting point higher than about 4O0C, but wherein the composition as a whole has a slip melting point below about 4O0C.
With "slip melting point" is meant here the temperature at which the amount of solid phase in the melting hydrocarbon composition has become so low that an air bubble is forced upwards in an open capillary filled with the hydrocarbon composition.
Salts of benzoic acid acceptable for use in food or feed are for example calcium, potassium, ammonium or sodium salts.
According to the present invention the composition contains flakes of benzoic acid or salt thereof. With a flake is meant here a body of solid benzoic acid or benzoate salt having an irregular shape comprising two essentially flat and parallel surfaces with about equal Feret's diameters along the two axes of the surfaces (Feretx and Ferety) and wherein the distance between the surfaces has a much smaller Feret's diameter (Feretz). Essentially parallel here means that the flat surfaces may have an angle with respect to each other of not more than about 10°.
A Feret's diameter is the distance between two tangents on opposite sides of a particle. The ratio between Feretmιn (the smallest value of Feretz of the particle) and Feretmax (the largest value of Feretx or Ferety of the same particle) is referred to here as the aspect ratio (AR). Hence
Feret- = AR
Feret max
The flakes of benzoic acid or benzoate salt typically have an AR of between 0.01 and 0.2. The compositions of benzoic acid or benzoate salt preferably contain at least 10 % w/w of flakes, more preferably at least 20% w/w of flakes, and further contain flake fragments. The flakes have Feretmax of at least 500 μm, preferably at least 1000 μm, more preferably at least 2000 μm.
The Feret's diameter can be measured e.g. microscopically or using the Sympatec Qicpic, a dynamic image analysis system using the Sympatec Gradis dispersion technique. This latter equipment is provided by Sympatec, Am Pulverhaus 1 , D-38678 Clausthal-Zellerfeld, Germany. In the Sympatec Gradis the particles are accelerated in a fail shaft by the gravity of earlh. Sympatec Qicpic is an image analysis sensor, which combines particle size and shape analysis. It uses an exposure time of less than 1 ns, which provides images of particles with a speed of up to 100 m/s. More -A-
information is provided at http://www.sympalec.com/lmageAnalysis/QICPIC.hlml and at http.//www. sympatec.com/lmageAnalysis/GRADlS-L.html.
Benzoic acid or benzoate salt flakes have the tendency to erode easily during handling, i.e. the sharp edges of the flakes may easily brake upon contact between the flake particles or of flake particles with other solid materials. It was expected that this also would be the case with coated flakes and that this would give rise to partial loss of the coating (which would lead to hygroscopic behavior of the particles, such as caking) and/or to generation of smaller dust-forming particles.
Surprisingly, upon handling the coated flake containing compositions did not show the formation of dust particles nor did it lead to loss of coating to an extent that hygroscopic behavior occurred.
According to a preferred embodiment of the present invention the dosage of the hydrocarbon substance to benzoic acid or a salt thereof is between 0.05 and 10 mass %. The coated benzoic acid or salt thereof according to the present invention may be used as a constituent of food or feed e.g. to reduce the emission of ammonia in the excrements animals.
The present invention also relates to food or feed compositions comprising coated particles as described herein. Furthermore, the present invention relates to premixes for use in the preparation of food or feed compositions, wherein the premixes comprise coated particles as described herein.
The coating of the particulate benzoic acid or salt thereof can be carried out for example by adding the coating composition drop-wise into a rotating drum or any other type of mixing device containing flakes of benzoic acid or a slat thereof
The composition containing flakes of benzoic acid or salt thereof can also be spray coated. To this end the coating composition is sprayed onto said composition of benzoic acid or salt thereof by means of a nozzle. This can be done in a rotating drum or any other type of mixing device.
Further methods for the coating of particles according to the present invention are rotating pan coaters, drum coaters and fluid bed coaters which are typical coating unit operations with the particle technology field (see W. Pietsch,
Agglomeration Processes - Phenomena, Technologies, Equipment, Wiley-VCH Verlag GmbH, 2002). Examples Materials used
Benzoic acid flakes (VevoVitall) supplied by DSM Nutritional Products, Deinze Soy oil supplied by Van Wijk & Olthuis - slip melting point typically -10 °C.
Test descriptions
1. Uniaxial caking test
The caking test is done as follows: a cylindrical sample holder is filled with 100-200 g of material. The sample holder is made of a flexible rubber membrane; the sample holder is closed with a lid that is attached to the flexible membrane; the sample holder is put upside down and placed in a pressure chamber; because of the flexible membrane pressure can be applied on the sample by applying an overpressure in the chamber: the sample is consolidated; - an overpressure of 1 bar is used; the sample is stored at room temperature during 1 day; after storage the caked samples are broken by means of a tensile/consolidating bench. This is done by lowering a piston on the sample holder and recording the stress needed to break the sample. The maximum value recorded is the caking tendency expressed in bar (i.e. the maximum force divided by the top surface of the sample holder with a diameter of 40 mm).
The value for a reasonable caking tendency is below 0.8 bar, preferably below 0.5 bar and most preferably below 0.25 bar.
2. Small bag caking test
The principle of the small bag caking test consists of placing small bags with about 200 g of material under a consolidation load (-15 kPa) and store them for 14 days at room temperature. After storage the weight percentage of lumps in the bag is measured. This is a measure for the caking tendency of the material.
Example 1 Application of coating on benzoic acid flakes
Soy oil was heated to 80 0C and was added drop wise to 1500 g of benzoic acid flakes that were kept moving in a rotating drum (35 rpm, diameter 25 cm, length 15 cm) at room temperature. The total rotating of the benzoic acid flakes in the drum took about 3 minutes.
Effect of coating on caking tendency
Table 1 : Caking results of benzoic acid flakes
Figure imgf000007_0001
value is average of 3 tests *2 value is average of 5 tests
Effect of coating on dust formation The coating has a positive effect on the dustiness of the product. Dust consists of small particles and can be measured by quantifying the fraction of particles smaller than 0.5 mm.
Quantification of the fraction smaller than 0.5 mm particles is measured by sieving with a 0.5 mm sieve on a Retsch sieve machine type AS 200 control "g". The amplitude setting is 1 mm, the sieving time 1 minute and about 50 gram of material is sieved at one time. In total about 300 grams of material has been sieved.
Table 2: Dust in benzoic acid flakes
Figure imgf000007_0002
The results in table 2 show that coated benzoic acid flakes has less free small particles than untreated benzoic acid flakes. The coating makes the smaller particles stick to the larger particles and thus less small particles are free to form dust. This was also visible from the fact that with no coating applied to the product more dust adhered to the walls than with the coated product.
Furthermore, it was clearly observed that the smell (typical for benoic acid preparations) of the coated particles was considerably less than the smell of the non-coated particles.

Claims

1. A coated composition containing benzoic acid or a salt thereof comprising flake particles of benzoic acid or a salt thereof provided with an outer layer of a hydrocarbon composition, wherein the hydrocarbon composition has a slip melting point below 4O0C.
2. A coated particle according to claim 1 , characterized in that the hydrocarbon composition contains a compound selected from at least on member of the group consisting of a natural oil, a vegetable oil, a mineral oil, a synthetic oil, a fatty alcohol, a bi-functional alcohol and a tri-functional alcohol.
3. A method for the preparation of a coated composition containing flakes of benzoic acid or a salt thereof by contacting a powder containing flakes of benzoic acid or a salt thereof with a liquid hydrocarbon composition having a slip melting point below about 4O0C and mixing these components under conditions suitable to essentially maintain the particulate nature of the composition.
4. A method for the improvement of the flowability of a composition containing flakes of benzoic acid or a salt thereof by contacting a powder containing flakes of benzoic acid or a salt thereof with a liquid hydrocarbon composition having a slip melting point below about 4O0C and mixing these components under conditions suitable to essentially maintain the particulate nature of the composition.
5. A method for reducing the caking tendency of particles of a composition containing flakes of benzoic acid or a salt thereof by contacting a powder containing flakes of benzoic acid or a salt thereof with a liquid hydrocarbon composition having a slip melting point below about 4O0C and mixing these components under conditions suitable to essentially maintain the particulate nature of the composition.
6. A method for reducing the odor of particles of a composition containing flakes of benzoic acid or a salt thereof by contacting a powder containing flakes of benzoic acid or a salt thereof with a liquid hydrocarbon composition having a slip melting point below about 4O0C and mixing these components under conditions suitable to essentially maintain the particulate nature of the composition.
7. A method for reducing the development of dust during the handling of a composition containing flakes of benzoic acid or a salt thereof by contacting a powder containing flakes of benzoic acid or a salt thereof with a liquid hydrocarbon composition having a slip melting point below about 4O0C and mixing these components under conditions suitable to essentially maintain the particulate nature of the composition.
8. A method according to any of claim 3 to 7, characterized in that the hydrocarbon composition contains a compound selected from at least on member of the group consisting of a natural oil, a vegetable oil, a mineral oil, a synthetic oil, a fatty alcohol, a bi-functional alcohol and a tri-functional alcohol.
9. Method according to any of claims 3 to 8, characterized in that the dosage of the hydrocarbon substance to the benzoic acid or a salt thereof is between 0.05 and 10 mass %.
10. Method according to any of claims 3 to 9, characterized in that the particles of benzoic acid or a salt thereof is spray coated or dripped with the hydrocarbon composition.
1 1. Food or feed compositions comprising coated particles according to claim 1 or 2.
12. Premixes for use in the preparation of food or feed compositions, wherein the premixes comprise coated particles according to claim 1 or 2.
PCT/EP2008/060401 2007-08-20 2008-08-07 Coated benzoic acid or benzoate salt WO2009024475A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP07114591.6 2007-08-20
EP07114591 2007-08-20

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015011271A1 (en) * 2013-07-26 2015-01-29 Dsm Ip Assets B.V. Improved powderous formulations of organic acids or esters having an aromatic ring system
US9504269B2 (en) 2012-02-14 2016-11-29 Purina Animal Nutrition Llc Weatherized minerals and methods of making and using same

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3520965A (en) * 1968-07-09 1970-07-21 Tenneco Chem Treatment of sodium benzoate
US5008118A (en) * 1987-06-23 1991-04-16 Nippon Oil And Fats Method for producing organic agent coated with powders of coating agent
GB2388008A (en) * 2002-05-03 2003-11-05 Danisco Coating food grade powders to aid dispersion
EP1413202A1 (en) * 2002-10-22 2004-04-28 CSM Nederland B.V. Lipid-encapsulated functional bakery ingredients

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3520965A (en) * 1968-07-09 1970-07-21 Tenneco Chem Treatment of sodium benzoate
US5008118A (en) * 1987-06-23 1991-04-16 Nippon Oil And Fats Method for producing organic agent coated with powders of coating agent
GB2388008A (en) * 2002-05-03 2003-11-05 Danisco Coating food grade powders to aid dispersion
EP1413202A1 (en) * 2002-10-22 2004-04-28 CSM Nederland B.V. Lipid-encapsulated functional bakery ingredients

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9504269B2 (en) 2012-02-14 2016-11-29 Purina Animal Nutrition Llc Weatherized minerals and methods of making and using same
US10709154B2 (en) 2012-02-14 2020-07-14 Purina Animal Nutrition Llc Weatherized minerals and methods of making and using same
US10856561B2 (en) 2012-02-14 2020-12-08 Purina Animal Nutrition Llc Weatherized minerals and methods of making and using same
WO2015011271A1 (en) * 2013-07-26 2015-01-29 Dsm Ip Assets B.V. Improved powderous formulations of organic acids or esters having an aromatic ring system
JP2016539636A (en) * 2013-07-26 2016-12-22 ディーエスエム アイピー アセッツ ビー．ブイ． Improved powder formulations of organic acids or esters having aromatic ring systems
US9693938B2 (en) 2013-07-26 2017-07-04 Dsm Ip Assets B.V. Powderous formulations of organic acids or esters having an aromatic ring system

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