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PT81097B - METHOD FOR PREPARING A STABLE ANTI-PLASTIC DENTIFRICE CONTAINING A QUATERNARY AMMONIUM COMPOSITE - Google Patents

METHOD FOR PREPARING A STABLE ANTI-PLASTIC DENTIFRICE CONTAINING A QUATERNARY AMMONIUM COMPOSITE Download PDF

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Publication number
PT81097B
PT81097B PT81097A PT8109785A PT81097B PT 81097 B PT81097 B PT 81097B PT 81097 A PT81097 A PT 81097A PT 8109785 A PT8109785 A PT 8109785A PT 81097 B PT81097 B PT 81097B
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Prior art keywords
water
process according
gel
gel phase
amount
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PT81097A
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Portuguese (pt)
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PT81097A (en
Inventor
Robert J Ferlauto
Kathleen M Yuhasz
Original Assignee
Colgate Palmolive Co
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Publication of PT81097A publication Critical patent/PT81097A/en
Publication of PT81097B publication Critical patent/PT81097B/en

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/042—Gels
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/26—Aluminium; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/416—Quaternary ammonium compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A61K8/442—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof substituted by amido group(s)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/731—Cellulose; Quaternized cellulose derivatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/54—Polymers characterized by specific structures/properties
    • A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge
    • A61K2800/5422—Polymers characterized by specific structures/properties characterized by the charge nonionic

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Dispersion Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Cosmetics (AREA)
  • Dental Preparations (AREA)

Abstract

A chemically and physically stable antiplaque dentifrice comprises an antiplaque quaternary ammonium compound, a betaine surfactant, a humectant system of glycerin and/or sorbitol and a nonionic gelling agent, and is prepared by a process which comprises the preparation of two separate gel phases, an oil gel phase and a water gel phase, combining the gel phases into a single gel, and adding a dental abrasive as the final step, or adding the abrasive to the water gel phase prior to the addition of the oil gel phase.

Description

Descrição detalhada do invento

Os inventos que se seguem ilustram melhor a natureza do presente invento mas é obvio que o invento não se confina aos mesmos. As composições preparam-se de modo usual e todos os compostos e proporções referidos aqui e nas reivindicações em anexo referem-se a quantidades em peso, a não ser que se indique de outro modo.

Exemplo 1

Dentifrico Antiplaca de humectante de glicerina

Ingredientes _%

Agua (desionizada) 19,34 Sacarina sídica 0,30 Monofluorofosfato de sódio 0,76 Hidroxietilcelulose 1,10 Glicerina 20,00 Cloreto de benzotónio 0,50 Aromatizante 1,00 Cocoamidopropi1 betaína 5,00 Alumina calcinada 10,00 Alumina hidratada 42,00

Dispersa-se o cloreto de benzetóniO no aromatizante e agita-se esta dispersão na betaina para formar um gel de óleo. Dissolve-se a sacarina sódica e o monofluorofosfato de sódio (MFP) em ãgua. Dispersa-se hidroxietilcelulose em glicerina e adiciona-se esta mistura â solução de âgua-sacarina-MFP, que se agita para formar um gel de âgua. Misturam-se os geles de óleo e água para formar um gel matriz estável. Mistura-se alumina calcinada e alumina hidratada com o gel matriz para produzir um dentifrico final que é eficaz contra a bactéria relacionada com a placa possuindo uma excelente estabilidade química e cosmética bem como a característica de espuma suficiente. Este dentifrico ê preparado â temperatura ambiente.

Exemplo 2

Repete-se o exemplo 1 exceptuando a substituição de sorbitol a 20% por glicerina a 20%. 0 produto

resultante é igualmente eficaz contra a bactéria relacionada com a placa e também possui uma excelente estabilidade química e cosmética e propriedades de espuma suficientes.

Estudos de estabilidade MFP indicam que o novo dentifrico de glicerina e dentifrico de sorbitol apresentam um excelente perfil de estabilidade MFP. 0 exemplo 1 (glicerina a 20%), apresentava um valor total de fluoreto solúvel de 990 ppm e um valor de MFP como F de 950 ppm.

20um valor inicial de MFP como F de

0 exemplo 2 (sorbitol a 20%) apresentav de solubilidade total de fluoreto e um valor 1.020 ppm e 980 ppm respectivamente

Quadro III

Perfil de Estabilidade do MFP de um novo dentifrico BTC composto totalmente por glicerina e um novo dentifrico BTC composto totaímente por sorbitol

(nove semanas (s) de envelhecimento a 49°C)

PH Ex. Humectante T F solúvel F iónico MPP como P 9s I 9s i 9s I 9s 1 totalmente com 7,8 8,o 990 820 43 94 950 730 postos glicerina 2 totalmente com 7,6 7,7 1020 960 43 45 980 910 postos sorbitol 0 perfil de pH de ambas as formulações só aumentou ligeiramente nove semanas após o envelhecimento

a 49°C. Após um envelhecimento acelerado, os valores do total de fluoreto solúvel e de MFP como F eram de 820 ppm e

730 ppm respectivamente para o Exemplo 1 e 960 ppm e 910 ppm respectivamente para o Exemplo 2.

Pode-se alterar as formulações acima

indicadas. Por exemplo, pode-se substituir nos exemplos,

cocoamidopropi1. , por outras betaínas como a lauroamidopropil betaína, cocobetaina e outros semelhantes. Do mesmo modo

21podem substituir-se por outros abrasivos, os abrasivos específicos dos exemplos. De modo idêntico podem substituir-se outros compostos contendo fluoreto como o fluoreto de sódio, fluoreto de potássio etc. pelo monofluorofosfato de sódio dos exemplos correspondentes. De modo análogo podem substituir-se por cloreto de benzetónio e cloreto cetil piridínio ou outros agentes antiplaca de amónio quaternário. 0 ciclamato de sódio também pode substituir a sacarina sódica.

E evidente que a presente descrição detalhada pretende ser unicamente uma ilustração e que se poderão fazer variações a partir da presente sem que se verifique um afastamento do espirito do invento.

0 resumo anteriormente exposto aparece meramente para conveniência de investigadores técnicos e não deverá ser tomado em consideração no que respeita ao âmbito do invento.

‘V.

Detailed Description of the Invention

The following inventions further illustrate the nature of the present invention but it is obvious that the invention is not confined thereto. The compositions are prepared in the usual manner and all the compounds and proportions referred to herein and in the appended claims refer to amounts by weight, unless otherwise indicated.

Example 1

Dentifrice Glycerin Humectant Antiplaque

Ingredients _%

Water (deionized) 19.34 Saccharin sodium 0.30 Sodium monofluorophosphate 0.76 Hydroxyethylcellulose 1.10 Glycerin 20.00 Benzotonium chloride 0.50 Flavoring 1.00 Cocoamidopropyl betaine 5.00 Calcined alumina 10.00 Hydrated alumina 42.00

The benzethonium chloride is dispersed in the flavorant and this dispersion is stirred in the betaine to form an oil gel. Dissolve sodium saccharin and sodium monofluorophosphate (MFP) in water. Hydroxyethylcellulose is dispersed in glycerin and this mixture is added to the water-saccharin-MFP solution, which is stirred to form an aqueous gel. The oil and water gels are mixed to form a stable matrix gel. Calcined alumina and hydrated alumina are mixed with the matrix gel to produce a final dentifrice that is effective against plaque-related bacteria having excellent chemical and cosmetic stability as well as sufficient foam characteristics. This dentifrice is prepared at room temperature.

Example 2

Example 1 is repeated except that 20% sorbitol is replaced with 20% glycerol. The product

is also effective against plaque-related bacteria and also has excellent chemical and cosmetic stability and sufficient foam properties.

MFP stability studies indicate that the new glycerin dentifrice and sorbitol dentifrice have an excellent MFP stability profile. Example 1 (20% glycerol) had a total soluble fluoride value of 990 ppm and a MFP value as F of 950 ppm.

An initial value of MFP as F of

Example 2 (20% sorbitol) shows total fluoride solubility and a value of 1020 ppm and 980 ppm respectively

Table III

Stability Profile of the MFP of a new BTC dentifrice composed entirely of glycerine and a new BTC dentifrice all compounded by sorbitol

(nine weeks of aging at 49øC)

PH Ex. Humectant T Soluble F F ionic MPP as P 9s I 9s i 9s I 9s 1 with 7.8 8, o 990 820 43 94 950 730 glycerin 2 totally with 7.6 7.7 1020 960 43 45 980 910 sorbitol stations 0 profile of pH in both the formulations only slightly increased nine weeks after the aging

at 49 ° C. After accelerated aging, the values of total soluble fluoride and MFP as F were 820 ppm and

730 ppm respectively for Example 1 and 960 ppm and 910 ppm respectively for Example 2.

The above formulations can be modified

indicated. For example, one may substitute in the examples,

cocoamidopropyl. , by other betaines such as lauroamidopropyl betaine, cocobetaine and the like. In the same way

They can be replaced by other abrasives, the specific abrasives of the examples. Similarly, other fluoride-containing compounds such as sodium fluoride, potassium fluoride and the like may be substituted. by the sodium monofluorophosphate of the corresponding examples. Similarly benzethonium chloride and cetyl pyridinium chloride or other quaternary ammonium antiplaque agents may be substituted. Sodium cyclamate may also substitute sodium saccharin.

It will be understood that the present detailed description is intended to be only an illustration and that variations may be made from the present without departing from the spirit of the invention.

The foregoing summary appears purely for the convenience of technical researchers and should not be taken into account with regard to the scope of the invention.

'V.

Claims (19)

REIVINDICAÇÕES 1-. - Processo para a preparação de um dentifrico antiplaca química e físicamente estável, caracterizado por se incluir no referido dentifrico um compos_ to de amónio quaternário antiplaca, um composto tensioactivo de betaína, um sistema humectante de glicarina e/ou sorbitol e um composto de gelificação não iónico e por compreender a preparação de duas fases gel separadas, uma fase óleo-gel e uma fase água-gel, a combinação das fases gel mencionadas num único gel e ainda a adição de um material abrasivo no passo final, ou a adição do referido material abrasivo â fase gel-ãgua antes da adição da fase óleo-gel.1-. A process for the preparation of a chemically and physically stable antiplaque dentifrice, characterized in that a quaternary ammonium antiplaque composition, a betaine surfactant compound, a glycine and / or sorbitol humectant system and a non-gelling compound are included in said dentifrice. and comprising the preparation of two separate gel phases, an oil-gel phase and a water-gel phase, the combination of the mentioned gel phases in a single gel and addition of an abrasive material in the final step, or the addition of said gel phase abrasive material to the gel-water phase prior to addition of the oil-gel phase. 2ã. - Processo de acordo com2 ã . - Process according to a reivindicação 1, caracterizado por a fase óleo-gel consistir no composto antiplaca de amónio quaternário, um composto tensioactivo de betaína e uma substância aromatizante: e por a fase água-gel consistir em água, humectante e um agente de gelificação não iónico.Claim 1, characterized in that the oil-gel phase consists of the quaternary ammonium antiplaque compound, a betaine surfactant compound and a flavoring substance: and in that the water-gel phase consists of water, a wetting agent and a nonionic gelling agent. 3â. - Processo de acordo com3 â . - Process according to a reivindicação 2, caracterizado por se dissolver um composto que contém fluor na quantidade de água de fórmula antes de se adicionar a água ao humectante e agente de gelificação na formação da fase água-gel.Claim 2, wherein a fluorine-containing compound is dissolved in the amount of water of formula prior to adding water to the humectant and gelling agent in the formation of the water-gel phase. 4â. - Processo de acordo com qualquer uma das reivindicações 2 ou3, caracterizado por se dissolver um material edulcorante solúvel em água, na quanU dade de água de fórmula, antes de se adicionar a água ao humectante e agente de gelificação na formação da fase água-gel.4 â . A process according to any one of claims 2 or 3, characterized in that a water-soluble sweetening material is dissolved in the quantity of water of formula, before the water is added to the humectant and gelling agent in the formation of the water-gel phase . 5â. - Processo de acordo com5 â . - Process according to eapMCJwrw’)»'37 eapMCJwrw ')''37 a reivindicação 4, caracterizado por o material edulcorante ser sacarina sódica.Claim 4, characterized in that the sweetening material is saccharin sodium. 62. - Processo de preparação de um dentifrico antiplaca cosmético e quimicamente estável, que consiste essencialmente na formação de duas fases, uma fase óleo-gel e uma fase água-gel, caracterizado por compreender a seguinte sequência de passos:6 2 . A process for preparing a cosmetically and chemically stable antiplaque dentifrice consisting essentially of two-phase formation, an oil-gel phase and a water-gel phase, characterized in that it comprises the following sequence of steps: a. dispersão da quantidade de fórmula de um agente antiplaca de amónio quaternário, na quantidade de fórmula de subs tância aromatizante,The. dispersing the amount of the formula of a quaternary ammonium antiplaque agent in the amount of the flavoring ingredient formula, b. mistura da dispersão amónio quaternário-substância aro matizante na quantidade de fórmula de composto tensioactivo de betaina para formar a fase Óleo-gel,B. mixing the quaternary ammonium dispersion-aromatic ring substance in the amount of betaine surfactant compound formula to form the Oil-gel phase, c. Dispersão da quantidade de fórmula de um agente de ge. lificação não iónico na quantidade de fórmula de um humectaji te de glicerina e/ou sorbitol,W. Dispersing the amount of the formula of an agent of ge. nonionic addition in the amount of the formula of a glycerol and / or sorbitol humectant, d. mistura da dispersão agente de gelificação humectante mencionada com a quantidade de fórmula de água para formar a fase água-gel,d. mixing the above mentioned wetting gelling agent dispersion with the amount of water formula to form the water-gel phase, e. combinação das.duas fases gel para formar uma fase gel original estável,and. combination of the two phases gel to form a stable original gel phase, f. adição do abrasivo dentário à fase água-gel ou â fase gel original por agitação, ef. adding the dental abrasive to the water-gel phase or the original gel phase by shaking, and g. obtenção de um dentifrico antiplaca estável.g. obtaining a stable antiplaque dentifrice. -247-. - Processo de acordo com a reivindicação 6, caracterizado por se dissolver um mate rial edulcorante solúvel em água, um composto que contém fluor ou ambos, na quantidade de água de fórmula antes de serem adicionados â dispersão humectante-agente de gelificação na formação da fase água-gel.-247-. 6. A process according to claim 6, wherein a water-soluble sweetening agent, a fluorine-containing compound or both are dissolved in the amount of water of the formula before being added to the wetting dispersion-gelling agent in the formation of the phase water-gel. 8a. - Processo de acordo com a reivindicação 7, caracterizado por o material edulcorante mencionado ser sacarina sódica e o composto que contêm fluor ser monofluorofosfato de sódio.8 a . 7. A process according to claim 7, wherein said sweetening material is saccharin sodium and the fluorine-containing compound is sodium monofluorophosphate. 9a. - Processo de acordo com9 a . - Process according to quaisquer das reivindicações 6-8, caracterizado por o agente de gel ser hidroxietilcelulose.any of claims 6-8, characterized in that the gel agent is hydroxyethylcellulose. 10a. - Processo de acordo com10 a . - Process according to a reivindicação 1, caracterizado por o conteúdo de betaína corresponder a cerca de 3-5% em peso da formulação.Claim 1, characterized in that the betaine content corresponds to about 3-5% by weight of the formulation. 11a. - Processo de acordo com a reivindicação 10, caracterizado por o agente de gelifica ção não iónico ser hidroxietilcelulose em quantidades de ce_r ca de 0,8-1,5% em peso.11 a . 5. A process according to claim 10, wherein the nonionic gelling agent is hydroxyethylcellulose in amounts of about 0.8-1.5% by weight. 12a. - Processo de acordo com a reivindicação 11, caracterizado por se incluir cerca de 18-23% em peso de glicerina, sorbitol ou uma sua mistura como sistema humectante.12 a . A process according to claim 11, characterized in that about 18-23% by weight of glycerin, sorbitol or a mixture thereof is included as a wetting system. 13a. - Processo de acordo com13 a . - Process according to a reivindicação 1, caracterizado por se incluir cerca deClaim 1, characterized in that about 35-65% em peso de um abrasivo dentário insolúvel em água.35-65% by weight of a water-insoluble dental abrasive. __ 2 gsiv__ 2 gsiv 14â. - Processo de acordo com a reivindicação 13, caracterizado por o abrasivo dentário ser um abrasivo que contém alumina.14 â . 11. A method according to claim 13, wherein the dental abrasive is an abrasive containing alumina. 15â. - Processo de acordo com a reivindicação 14, caracterizado por o agente antiplaca ser cloreto de benzetónio numa quantidade de cerca de 0,1-1% em peso.15 â . 5. A process according to claim 14, wherein the antiplaque agent is benzethonium chloride in an amount of about 0.1-1% by weight. 16â. - Processo de acordo com a reivindicação 3, caracterizado por o composto dador de fluoreto estar presente numa quantidade suficiente para libertar cerca de 0,005-1% em peso de ião fluoreto no dentí frico.16 â . A process according to claim 3, wherein the fluoride donor compound is present in an amount sufficient to deliver about 0.005-1% by weight of fluoride ion in the dentifrice. 175. - Processo de acordo com a reivindicação 16, caracterizado por o composto dador de fluoreto ser monofluorofosfato de sódio. 5 . A process according to claim 16, wherein the fluoride donor compound is sodium monofluorophosphate. 18â. - Processo de acordo com18 â . - Process according to a reivindicação 10, caracterizado por a betaína ser cocoamido propi1-betaína.Claim 10, wherein the betaine is cocoamido propyl betaine. 19â. - Processo de acordo com a reivindicação 14, caracterizado por o abrasivo ser uma mis_ tura de alumina hidratada e alumina calcinada.19 â . 6. A process according to claim 14, wherein the abrasive is a blend of hydrated alumina and calcined alumina. 205. - Processo de acordo com a reivindicação 2, caracterizado por a substância aromatiza^ te constituir cerca de 0,5-2% em peso. 5 . 2. A process according to claim 2, wherein the flavoring substance comprises about 0.5-2% by weight. -2621â. - Processo de acordo com a reivindicação 5, caracterizado por a sacarina sódica constituir cerca de 0,01-0,5% em peso.-2621 â . 5. A process according to claim 5, wherein the sodium saccharin constitutes about 0.01-0.5% by weight.
PT81097A 1984-09-10 1985-09-05 METHOD FOR PREPARING A STABLE ANTI-PLASTIC DENTIFRICE CONTAINING A QUATERNARY AMMONIUM COMPOSITE PT81097B (en)

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US5023074A (en) * 1986-05-13 1991-06-11 Colgate-Palmolive Company Stabilized amine fluoride dental cream
GB8719775D0 (en) * 1987-08-21 1987-09-30 Unilever Plc Oral products
US5783200A (en) * 1997-01-21 1998-07-21 The Procter & Gamble Company Personal cleansing compositions
US5785979A (en) * 1997-01-21 1998-07-28 The Procter & Gamble Company Personal cleansing compositions
JP5168465B2 (en) * 2007-12-25 2013-03-21 ライオン株式会社 Dentifrice composition

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US4117107A (en) * 1975-10-17 1978-09-26 Noxell Corporation Method and composition for improving oral hygiene
SE431285B (en) * 1976-08-16 1984-01-30 Colgate Palmolive Co MUNVARDS COMPOSITION CONTAINING A PHOSPHONE SOCIETY, FOR REDUCING MISSING DIFFERENCE PICTURED BY AN INCLUDING NITROGEN ANTIBACTERIAL PLAQUE
US4130637A (en) * 1977-01-31 1978-12-19 Colgate-Palmolive Company Anti-plaque agents
SE444112B (en) * 1978-06-15 1986-03-24 Dental Therapeutics Ab DENTINYTOR CLEANER
IN161843B (en) * 1983-07-13 1988-02-13 Colgate Palmolive Co

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GB8522158D0 (en) 1985-10-09
ZW14385A1 (en) 1985-12-10
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GR852186B (en) 1986-01-10
IT8548541A0 (en) 1985-09-09
BE903203A (en) 1986-03-10
MY101907A (en) 1992-02-15
DK411085A (en) 1986-03-11
PH22177A (en) 1988-06-28
DK411085D0 (en) 1985-09-10
FI81256C (en) 1990-10-10
IT1182856B (en) 1987-10-05
ATA258285A (en) 1988-11-15
NL8502468A (en) 1986-04-01
SG54791G (en) 1991-09-13
DE3531337A1 (en) 1986-03-20
AU581247B2 (en) 1989-02-16
NZ213285A (en) 1988-07-28
ES8702785A1 (en) 1987-01-16
FI81256B (en) 1990-06-29
SE8504002D0 (en) 1985-08-28
MX164748B (en) 1992-09-21
NO853519L (en) 1986-03-11
HK61291A (en) 1991-08-16
NO165477B (en) 1990-11-12
AU4710885A (en) 1986-03-20
CH669112A5 (en) 1989-02-28
JPS6168409A (en) 1986-04-08
SE8504002L (en) 1986-03-11
KR920007830B1 (en) 1992-09-18
ZA856445B (en) 1987-04-29
ES546810A0 (en) 1987-01-16
AT388293B (en) 1989-05-26
PT81097A (en) 1985-10-01
SE458586B (en) 1989-04-17
NO165477C (en) 1991-02-20
CA1261758A (en) 1989-09-26
BR8504325A (en) 1986-07-01
FI853425L (en) 1986-03-11
FR2569981A1 (en) 1986-03-14
GB2164255A (en) 1986-03-19
KR860002264A (en) 1986-04-24
GB2164255B (en) 1988-08-17
ZM5985A1 (en) 1987-04-30
IN164485B (en) 1989-03-25
FR2569981B1 (en) 1990-02-02

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