WO2004045319A1 - Produit encapsule et procede de preparation et d'utilisation de celui-ci - Google Patents

Produit encapsule et procede de preparation et d'utilisation de celui-ci Download PDF

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Publication number
WO2004045319A1
WO2004045319A1 PCT/EP2003/012836 EP0312836W WO2004045319A1 WO 2004045319 A1 WO2004045319 A1 WO 2004045319A1 EP 0312836 W EP0312836 W EP 0312836W WO 2004045319 A1 WO2004045319 A1 WO 2004045319A1
Authority
WO
WIPO (PCT)
Prior art keywords
acid
encapsulated
active ingredient
encapsulated product
encapsulation
Prior art date
Application number
PCT/EP2003/012836
Other languages
English (en)
Inventor
Finn Madsen
Original Assignee
Danisco A/S
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
Application filed by Danisco A/S filed Critical Danisco A/S
Priority to AU2003289874A priority Critical patent/AU2003289874A1/en
Publication of WO2004045319A1 publication Critical patent/WO2004045319A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A21—BAKING; EDIBLE DOUGHS
    • A21D—TREATMENT, e.g. PRESERVATION, OF FLOUR OR DOUGH, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS; PRESERVATION THEREOF
    • A21D2/00—Treatment of flour or dough by adding materials thereto before or during baking
    • A21D2/08—Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
    • A21D2/14—Organic oxygen compounds
    • A21D2/16—Fatty acid esters
    • A—HUMAN NECESSITIES
    • A21—BAKING; EDIBLE DOUGHS
    • A21D—TREATMENT, e.g. PRESERVATION, OF FLOUR OR DOUGH, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS; PRESERVATION THEREOF
    • A21D2/00—Treatment of flour or dough by adding materials thereto before or during baking
    • A21D2/08—Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
    • A21D2/14—Organic oxygen compounds
    • A—HUMAN NECESSITIES
    • A21—BAKING; EDIBLE DOUGHS
    • A21D—TREATMENT, e.g. PRESERVATION, OF FLOUR OR DOUGH, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS; PRESERVATION THEREOF
    • A21D8/00—Methods for preparing or baking dough
    • A21D8/02—Methods for preparing dough; Treating dough prior to baking
    • A21D8/04—Methods for preparing dough; Treating dough prior to baking treating dough with microorganisms or enzymes
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/70—Fixation, conservation, or encapsulation of flavouring agents
    • A23L27/72—Encapsulation
    • 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
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

Definitions

  • the present invention relates to an encapsulated product that comprises an improved encapsulation providing desired release properties for the prospective use.
  • the invention also relates to a method of preparing an encapsulated product and to the use thereof.
  • An encapsulated process according to the invention can be used in various food industry applications.
  • Encapsulation has been used in the food industry for more that 30 years, and normally involves the coating of an ingredient before introducing it into a food system.
  • the combination of the coating and the ingredient is referred to as an encapsulate.
  • Ingredients used in the food industry are sometimes encapsulated in fatty substances (such as triglycerides and emulsifiers), starch, carbohydrates (such as sugars), maltodextrin or hydro- colloids, for a variety of reasons, including improved functionality of the ingredient, accurate timing of the release of the ingredient into the desired food system, protection of the ingredient from degradation during processing and storage of the food systems, prevention of premature reactions, precise delivery of the ingredient into the food system and taste masking of vitamins and minerals.
  • fatty substances such as triglycerides and emulsifiers
  • starch such as starch
  • carbohydrates such as sugars
  • the release of an active ingredient may be controlled by e.g. the temperature, mechanical stress, time, pH or osmotic pressure.
  • the temperature is used to control the release of an active ingredient into a food system, the release is retarded until the food system approaches or attains the melting temperature of the encapsulation material. At that temperature the active ingredient is ultimately released into the food product.
  • the encapsulation is also used to improve e.g. the handling of the active ingredient. Active ingredients as such may be difficult to handle because of dusting.
  • the handling and the dosage of an active ingredient might be improved when the active ingredient is encapsulated in beads.
  • calcium propionate is used in bakery products to prevent moulding and to provide long shelf life to the product.
  • the calcium propionate encapsulated in beads of an emulsifier is only partially released from the beads during mixing and proofing of the dough and a final release is obtained when the temperature of the dough approaches or attains the melting temperature of the emulsifier used for the encapsulation
  • Calcium propionate is difficult to handle because of its property to dust when added into a dough. In order to diminish the dusting of the calcium propionate it has been encapsulated in e.g. emulsifiers.
  • US 6,312,741 describes a monodis- persed fumaric acid particulate encapsulated with a coating having a melting point within normal baking temperature.
  • the encapsulated fumaric acid is used in dough compositions to provide an acid environment into a dough.
  • the encapsulation of fumaric acid or other acidu- lants prevents the unwanted acid hydrolysis of other food components and ingredients.
  • flavours such as strawberry flavouring
  • the release of the flavour is retarded and a final release is obtained when the food product approaches or attains the melting temperature of the coating material in question.
  • Fat encapsulation of FeSO 2 alone or with ascorbic acid, and FeCl 3 , were developed to fortify cheese and other high moisture foods with iron. It was shown that microcapsules made with cottonseed stearine had good oxidative stability and low leakage of iron under rapid stirring of food systems.
  • the encapsulation is not always as effective as intended for example because of the structure of the encapsulate. In some cases it is desirable that the active ingredient is released little by little from the encapsulated product or that it is released in several stages. If the encapsulation has a very porous structure with many cracks and channels, it might be difficult to control the leakage of the ingredient resulting in a premature release from the encapsulate and therefore a different or non-optimal effect of the ingredient not.
  • Some of the active ingredient may be lost due to a too early release through the cracks and channels in the encapsulation.
  • the active ingredient may also be released at a wrong time so that the conditions are not suitable for its action and it does not work properly.
  • calcium propionate may harm the yeast in a dough if it is released at a wrong time.
  • Too early release of a baking powder causes premature gas release, which deteriorates the quality of the final product.
  • An encapsulated product of the invention comprises an active ingredient encapsulated by an encapsulation material, which comprises a fatty substance and a conditioner. It has been surprisingly found that the integration of a conditioner to the encapsulation material improves the effect of the encapsulation. It is possible to prohibit, retard or control the release of the active ingredient from said encapsulated product with the present invention.
  • One object of the present invention is to provide an improved encapsulation to the encapsulated product and thus provide appropriate release properties of the active ingredient when released from the encapsulated product.
  • the active ingredient is not released too early because of the defects in the encapsulation, but the active ingredient is released precisely at the desired time. The timing of the release is determined by e.g. the melting properties of the encapsulation material, mechanical stress, time, pH or osmotic pressure.
  • the fatty substance used in the present invention is any conventional fatty substance used in encapsulation.
  • the fatty substance forms the basis of the encapsulation material used in the encapsulation of an active ingredient.
  • a conditioner is used in the encapsulation material in addition to the fatty substance.
  • the conditioner and the fatty substance together form an encapsulation material, which provides specific release properties to the product.
  • the encapsulation material itself may also be an active ingredient.
  • the fatty substance used in the present invention is a component selected from the group consisting of a monoglyceride of an edible fatty acid, a diglyceride of an edible fatty acid, a mono/diglyceride of an edible fatty acid, a triglyceride of an edible fatty acid, a mixture of such glycerides, waxes, a propylene glycol ester of an edible fatty acid, a stearoyl lactylate, a sucrose ester of an edible fatty acid, a diacetyl tartaric acid ester of a mono- or diglyceride of an edible fatty acid, a citric acid ester of a mono- or diglyceride of an edible fatty acid and an acetic acid ester of a mono- or diglyceride of an fatty edible acid.
  • the conditioner used in the present invention is any substance that is capable of influencing the crystallizing and re-crystallisation properties of the fatty substance used in the encapsulation of an active ingredient with the encapsulation material.
  • crystallizing means the phase where a liquid is transformed into a crystal form.
  • re-crystallisation on the other hand means the transformation from one crystal form into another.
  • the conditioner is preferably an anti-crystallizer, a plasticizer and/or a kinetic modifier.
  • Especially preferred conditioners are a sorbitan ester of an edible fatty acid, lecithin, a lecithin fraction, a phosphor lipid or a combination thereof.
  • the active ingredients used in the invention are any active food ingredients.
  • the active ingredients used in the present invention are e.g. preservatives, flavours, spices, sweeteners, amino acids, colours, vitamins, minerals or biologically active ingredients like enzymes or microorganisms functioning during the production or in the final product.
  • Preferred active ingredients used in the present invention are adipic acid, ascorbic acid, azodi- carbonamide, calcium propionate, citric acid, delta-gluconolactone, fumaric acid, lactic acid, malic acid, potassium propionate, potassium sorbate, sodium aluminium phosphate, sodium bicarbonate, sodium chloride, sodium diacetate, sodium propionate, sorbic acid, sorbitol, tartaric acid, vanillin, xylitol, amino acids, flavours, colours, vitamins, minerals enzymes and/or microorganisms.
  • the present invention relates also to a method of preparing an encapsulated product comprising an active ingredient encapsulated by an encapsulation material.
  • a fatty substance and a conditioner are mixed to obtain the encapsulation material.
  • the active ingredient is then encapsulated with said encapsulation material by matrix encapsulation, layered coating or a combination thereof to prohibit, retard or control the release of said active ingredient from said encapsulate.
  • Matrix encapsulation is performed in a conventional way by spray cooling or drum cooling of a homogeneous blend of the melted encapsulating material and the active ingredient. In order to keep the blend homogeneous constant agitation may be used.
  • Layered coating is performed in a conventional way by fiuidising the active ingredient while the melted encapsulating material is sprayed on the surface (of the active ingredient).
  • the air used to fluidise the active ingredient is at the same time used for cooling the product.
  • molten encapsulation material In spray chilling molten encapsulation material is solidified using chilled air.
  • the active ingredient is dispersed in a molten encapsulation material.
  • the dispersion is atomised into a cooling chamber where the encapsulate solidifies.
  • a bed or a column of solid particles is suspended in a moving gas stream.
  • a liquid encapsulation material is sprayed onto the suspended particles and the coated particles are cycled into a zone where the encapsulation material is solidified by solvent evaporation or by cooling.
  • the amount of said conditioner is used in present invention is determined by the prospective use of the encapsulated product.
  • the amount of the conditioner is preferably about 0.1 to 5 %, more preferably about 0.5 to 2 %, most preferably about 1 to 1.5 %.
  • a conditioner like an anti-crystallizer
  • a fatty substance such as an emulsifier
  • distilled monoglyceride is used as a fatty substance and sorbitan tristearate is used as a conditioner.
  • Sorbitan tristearate is an anti-crystallizer, which can be used for example for retarding the crystal transformation or for preventing cloudiness in liquid oils caused by the presence of fat crystals.
  • the amount of said anti-crystallizer is about 0,1 to 5 %, preferably about 0,5 to 2 %, most preferably about 1 to 1,5 % based on the weight of said emulsifier.
  • the active ingredient used in this embodiment is calcium propionate.
  • Calcium propionate is encapsulated by matrix coating with said encapsulation material.
  • the encapsulation material comprising distilled monoglyceride and sorbitan tristearate provides a tighter encapsulation to the encapsulated product.
  • the right timing of the release of the calcium propionate provided by the tight encapsulation gives less inhibition to the yeast growth resulting in a higher dough and bread volume or alternatively allows the use of less yeast.
  • An encapsulated product according to the present invention is used in various applications in the food industry.
  • the release of an active ingredient is prohibited, retarded or controlled by the use of an encapsulated product according to the invention in e.g. bakery, dairy, ice cream, confectionary, fruit preparations, fat or any other food product. It is obvious for those skilled in the art that there are many more food applications in which the invention will work as well.
  • the fat part was melted, and calcium propionate was dispersed in the liquid fat phase.
  • Spray cooling was performed using a Niro FU11 spray tower, Type P6,3.
  • the calcium liberation was measured in a dough model system.
  • the encapsulated product was added to dough, which was mixed in a mini dough mixer (Farino- graph). Calcium dissolution was measured as a function of time using a calcium selective electrode. (Radiometer SE 25 Ca electrode). The test showed that the calcium liberation was slowed down in the encapsulated product according to the invention compared to a conventional encapsulated product.
  • Figure 1 shows the release curves of calcium propionate in a dough model system.
  • the solid circles curve represents the release profile of the non-encapsulated product.
  • the curve with triangles are an encapsulate based on DIMODAN® HP and calcium propionate and finally the curve with the squares is an encapsulate comprising a fat matrix composed of 99.0 % DIMODAN® HP and 1.0 % GRINDSTED® STS 30 (Sorbitan tristearate) as a modifier and calcium propionate. It is easily seen that the encapsulate containing GRINDSTED® STS 30 as a modifier has a slower release and thereby an enhanced encapsulation efficiency.
  • a Chopin Rheofermentometer analysis was used to measure the gas release from a dough system.
  • the gas is produced by the yeast and therefore an indication of the effectiveness of the yeast. Normally the calcium propionate inhibits the yeast growths, which is an unwanted effect. Gas release was followed during 183 minutes proofing period at 30 °C. The test showed that the yeast growth was not inhibited as much as with a conventional encapsulated product resulting in a higher dough volume and a higher gas release. The results can be seen in Figures 2 to 5.
  • Figure 2 shows the gas release of a standard dough system without any addition of calcium propionate.
  • the two numbers in focus are the total gas release after 3 hours and 3 minutes and the gas release after 20 minutes here used as an index.
  • the total gas release is 1604 mL and the release after 20 minutes is at index 42.
  • Figure 3 shows the gas release of a standard dough system with the addition of unencapsulated calcium propionate.
  • the total gas release is 1318 mL and the gas release after 20 minutes is at index 23.
  • These numbers are regarded as a negative reference as they indicate that the yeast growth has been inhibited and does not perform at its optimal.
  • Figure 4 shows the gas release of a standard dough system with the addition of calcium propionate encapsulated in a distilled monoglyceride.
  • the total gas release is 1455 mL and the gas release after 20 minutes is at index 27.
  • These numbers indicate that the encapsulation of calcium propionate has an influence on the dough system that makes the yeast perform better than with the addition of the unencapsulated calcium propionate. Though the gas release is not as good as in the dough system with calcium propionate.
  • Figure 5 shows the gas release of a standard dough system with the addition of a calcium propionate encapsulated in a fat system comprising a distilled monoglyceride and sorbitan tristearate according to the invention.
  • the total gas release is 1538 mL and the gas release after 20 minutes is at index 36.
  • the fat part was melted, and calcium propionate was dispersed in the liquid fat phase.
  • Spray cooling was performed using a Niro FU11 spray tower, Type P6,3.
  • Figures 6 shows the release curves of calcium propionate in a dough model system.
  • the solid circles curve represents the release profile of the non-encapsulated product.
  • the curve with triangles are an encapsulate based on DIMODAN® HP and calcium propionate and finally the curve with the squares is an encapsulate comprising a fat matrix composed of 99.5 % DIMODAN® HP and 0.5 % YOLKIN IP LECITHIN as a modifier and calcium propionate. It is easily seen that the encapsulate containing lecithin as a modifier has a slower release and thereby an enhanced encapsulation efficiency.
  • An encapsulated product containing 59.5 % distilled monoglycerides (DIMODAN® HP produced by Danisco A/S), 0.5 % lecithin (HEALTHY SOY LECITHIN) and 40 % calcium propionate was prepared.
  • the lecithin has an enriched content of phosphatidylcholin (PC).
  • PC phosphatidylcholin
  • the fat part was melted, and calcium propionate was dispersed in the liquid fat phase.
  • Spray cooling was performed using a Niro FU11 spray tower, Type P6,3.
  • Figures 7 shows the release curves of calcium propionate in a dough model system.
  • the solid circles curve represents the release profile of the non-encapsulated product.
  • the curve with triangles are an encapsulate based on DIMODAN® HP and calcium propionate and finally the curve with the squares is an encapsulate comprising a fat matrix composed of 99.5 % DIMODAN® HP and 0.5 % HEALTHY SOY LECITHIN as a modifier and calcium propionate. It is easily seen that the encapsulate containing lecithin as a modifier has a slower release and thereby an enhanced encapsulation efficiency.
  • the fat part was melted, and calcium propionate was dispersed in the liquid fat phase.
  • Spray cooling was performed using a Niro FU11 spray tower, Type P6,3.
  • Figures 8 shows the release curves of calcium propionate in a dough model system.
  • the solid circles curve represents the release profile of the non-encapsulated product.
  • the curve with triangles are an encapsulate based on DIMODAN® HP and calcium propionate and finally the curve with the squares is an encapsulate comprising a fat matrix composed of 99.5 % DIMODAN® HP and 0.5 % GRINDSTED® CITREM LR 10 as a modifier and calcium propionate. It is easily seen that the encapsulate containing GRINDSTED® CITREM LR 10 as a modifier has a slower release and thereby an enhanced encapsulation efficiency.
  • the present invention has been illustrated in detail by the above example. It is evident to those skilled in the art that the invention may be used in many different ways and many different applications.

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  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Microbiology (AREA)
  • Nutrition Science (AREA)
  • Biophysics (AREA)
  • Molecular Biology (AREA)
  • General Preparation And Processing Of Foods (AREA)

Abstract

L'invention concerne un produit encapsulé comprenant un ingrédient actif encapsulé par un matériau d'encapsulation, ce dernier comprenant une substance grasse et un améliorant. L'invention concerne également un procédé de préparation dudit produit encapsulé qui comprend un ingrédient actif encapsulé par un matériau d'encapsulation dans lequel une substance grasse et un améliorant sont mélangés afin d'obtenir ledit matériau d'encapsulation, ledit ingrédient actif étant encapsulé avec le matériau d'encapsulation par un procédé d'encapsulation matricielle, par un procédé de revêtement en couches ou une combinaison de ces procédés, afin d'empêcher, de retarder ou de commander la libération dudit ingrédient actif depuis ledit produit encapsulé. Ce produit encapsulé peut être utilisé dans diverses applications alimentaires.
PCT/EP2003/012836 2002-11-18 2003-11-17 Produit encapsule et procede de preparation et d'utilisation de celui-ci WO2004045319A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003289874A AU2003289874A1 (en) 2002-11-18 2003-11-17 An encapsulated product and a method for preparing and the use thereof

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0226877.9 2002-11-18
GBGB0226877.9A GB0226877D0 (en) 2002-11-18 2002-11-18 An encapsulated product and a method for preparing and the use thereof

Publications (1)

Publication Number Publication Date
WO2004045319A1 true WO2004045319A1 (fr) 2004-06-03

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GB (1) GB0226877D0 (fr)
WO (1) WO2004045319A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11186697B2 (en) 2017-12-20 2021-11-30 3M Innovative Properties Company Composite particles, composition and foam compositions containing composite particles, articles, and methods of making and using same
US11767406B2 (en) 2019-06-18 2023-09-26 3M Innovative Properties Company Compositions and foam compositions containing composite particles, articles, composite particles, and methods

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1190696A (en) * 1967-07-07 1970-05-06 Wallace & Tiernan Inc Baking Method and Salt Compositions.
JPS53127819A (en) * 1977-04-12 1978-11-08 Riken Vitamin Co Ltd Stabilization of l-asocorbic acid and its salt
JPS54157821A (en) * 1978-06-02 1979-12-13 Nippon Synthetic Chem Ind Co Ltd:The Sorbic acid preparation having improved quality
JPS5537159A (en) * 1978-09-07 1980-03-15 Nippon Synthetic Chem Ind Co Ltd:The Preparation of coated sorbic acid pharmaceutical
JPS5588666A (en) * 1978-12-27 1980-07-04 Ueno Seiyaku Oyo Kenkyusho:Kk Coated organic acid preparation having improved quality, and its preparation
US4218262A (en) * 1978-11-02 1980-08-19 Balchem Corporation Nonclumping, delayed action viscosity increasing agent
JPH01252241A (ja) * 1988-03-31 1989-10-06 Ajinomoto Co Inc 食用油脂コーティングドライイースト及びこれを用いたオールインワン型パンミックス粉
WO1999008553A1 (fr) * 1997-08-20 1999-02-25 Danisco A/S Compositions renfermant des additifs alimentaires encapsules et leur utilisation
US6312741B1 (en) * 2000-02-22 2001-11-06 Balchem Corporation Encapsulated food acids for preservation of baked goods

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1190696A (en) * 1967-07-07 1970-05-06 Wallace & Tiernan Inc Baking Method and Salt Compositions.
JPS53127819A (en) * 1977-04-12 1978-11-08 Riken Vitamin Co Ltd Stabilization of l-asocorbic acid and its salt
JPS54157821A (en) * 1978-06-02 1979-12-13 Nippon Synthetic Chem Ind Co Ltd:The Sorbic acid preparation having improved quality
JPS5537159A (en) * 1978-09-07 1980-03-15 Nippon Synthetic Chem Ind Co Ltd:The Preparation of coated sorbic acid pharmaceutical
US4218262A (en) * 1978-11-02 1980-08-19 Balchem Corporation Nonclumping, delayed action viscosity increasing agent
JPS5588666A (en) * 1978-12-27 1980-07-04 Ueno Seiyaku Oyo Kenkyusho:Kk Coated organic acid preparation having improved quality, and its preparation
JPH01252241A (ja) * 1988-03-31 1989-10-06 Ajinomoto Co Inc 食用油脂コーティングドライイースト及びこれを用いたオールインワン型パンミックス粉
WO1999008553A1 (fr) * 1997-08-20 1999-02-25 Danisco A/S Compositions renfermant des additifs alimentaires encapsules et leur utilisation
US6312741B1 (en) * 2000-02-22 2001-11-06 Balchem Corporation Encapsulated food acids for preservation of baked goods

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DATABASE WPI Section Ch Week 198005, Derwent World Patents Index; Class D12, AN 1980-08038C, XP002276527 *
DATABASE WPI Section Ch Week 198946, Derwent World Patents Index; Class D11, AN 1989-336993, XP002276528 *
PATENT ABSTRACTS OF JAPAN vol. 0040, no. 73 (C - 012) 28 May 1980 (1980-05-28) *
PATENT ABSTRACTS OF JAPAN vol. 0041, no. 40 (C - 026) 3 October 1980 (1980-10-03) *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11186697B2 (en) 2017-12-20 2021-11-30 3M Innovative Properties Company Composite particles, composition and foam compositions containing composite particles, articles, and methods of making and using same
US11767406B2 (en) 2019-06-18 2023-09-26 3M Innovative Properties Company Compositions and foam compositions containing composite particles, articles, composite particles, and methods
US12110375B2 (en) 2019-06-18 2024-10-08 3M Innovative Properties Company Compositions and foam compositions containing composite particles, articles, composite particles, and methods

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GB0226877D0 (en) 2002-12-24

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