DE2021786A1 - Coating compound - Google Patents

Description

Or. O. DfttTTunn K. L. Schiff Dr. A. ν. FOR DIPING. P. Strihl

fi Munich 9Q | Marirtiifptatj 2 * VTetoton 45 404Q 2021786

Patent application P 20 21 786 “1

Colorcon incorporated

Our file OÄ-K545 (E ~ 215b) A; May 1970

SB / KLS / Sch (copy of August 3, 1970)

Excess mass

Priority dated 9th time 1963 », United States v. America,

No. 823 _t 514 |

The invention relates to airtight and watertight Coating composition for tablets and the like based on stabilized shellac,

In the field of tlberdehece of phamiaseutlschen and HahrtingsBiitteitabletten, shellac has established itself as a very desirable coating compound for solid formulations and is used worldwide. In the pharmaceutical industry, pellets and tablets are coated with a coating film of shellac, and in the confectionery industry large quantities of shellac are used to glaze all types of solid goods. Probably no other material is so impermeable to gas and water vapor. The use of shellac has several disadvantages, however A well-known difficulty is that aged shellac solutions do not dry on a tray. Another

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Γ 20 21 73fi.l Colorcor Inc.

Difficulty lies in the fact that the Schallacküberzug on a The tablet hardens during storage and sometimes reaches such a hardness that the tablet will wear through after ingestion does not dissolve a patient and passes through the body without dissolution instead of being dissolved in the stomach or intestinal tract as intended to become.

Because of these problems, a great deal of research and work has been directed towards using shellac as a coating composition for tablets to improve or replace.

The aim of the invention is therefore to produce stabilized shellac for use as a sealant coating for tablets which dries easily on the tablet and does not harden during storage on the tablet and therefore no lack of dissolution in the stomach or after ingestion Showing intestinal tract of a patient. The invention also aims a process for the production of the stabilized shellac ^ Coating film and a tablet, which is provided with a dense coating film of stabilized shellac.

Shellac is a naturally occurring polyester that Contains free hydroxyl and carboxyl groups. The lack of drying aged shellac solution and hardening of shellac coatings during storage these free hydroxyl and carboxyl groups of the shellac can be attributed to «shellac. in alcohol shows a tendency during storage to cause to esterify solvents, being a non-drying material is formed · after application to a® tray® possesses the

Shellac the maturity for further polymerization and self-crosslinking via the free hydroxyl and carboxyl groups. This continued polymerization on the tablet makes the shellac coating film less soluble and causes delays in dissolving the tablet in the stomach or intestinal tract, which is undesirable are.

The invention now provides a shellac coating and a method for producing this coating, which Λ showed improved stability both during storage in the form of a solution and as an already applied film on a tablet Contains basic groups, to the shellac, such materials include polyvinylpyrrolidone (hereinafter often referred to as PVP for short) _/ polyvinylpyridine and polyamide hairs with free amino groups. These polymers block the carboxyl group of the shellac and prevent it from being crosslinked with the help of an acid-base reaction. The basic group ™ of the polyvinylpyrrolidone combines with the carboxyl group of the shellac and in this way blocks the esterification.

The invention accordingly provides a tightly sealing coating composition which is a polymeric material with free basic groups and shellac with free acid groups in a molar ratio of free basic groups to free acid groups of the shellac of about ItI contains. As a polymer material with free basic groups is probably polyvinylpyrrolidone

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BATH

DA-K545 -4- 202 ί 786

Subject invention also provides a process for preparing a stabilized shellac coating composition, in particular for coating tablets and the like, after a desired amount of shellac a quantity of a polymeric material containing free basic groups, in particular polyvinyl pyrrolidone added m.xa _s which the the corresponding to the acidic groups of the shellac © has the number of moles of basic groups and the shellac and the polymeric material are mixed with one another in a solvent. The number of acid groups in the shellac is determined by titrating a shellac sample.

The invention also relates to the use this coating composition for coating tablets.

By adding a certain amount of a basic polymer, some of the carboxyl groups are bound and the The proportion of carboxyl groups available for crosslinking is reduced, thereby reducing the undesirable crosslinking of the shellac is prevented.

By adding too much of the basic polymer, which are used to prevent undesired crosslinking of the shellac exceeds the required amount, a film having the properties of polyvinylpyrrolidone is formed, which is undesirable is because polyvinylpyrrolidone is not a tight seal against the ingress of moisture.

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The sealing properties of the Schellck film are desirable in coating tablets and the Coating compound must be composed so that the stability of the shellac is guaranteed without its being desirable Properties are noticeably changed. The adjustment of this composition requires knowledge of the stoichiometric Ratios of shellac and the basic polymer used. - .- ■■ '.. ■ "." .- ::. ■ -

The composition of the shellac varies depending on the origin and treatment of the shellac, incl. the amount of blessings, the health of the trees, depending on whether the shellac was dewaxed, in what way the shellac has been discolored and the like. Because of these fluctuations, one mole of free carboxyl groups in 600 grams of shellac solids, or in 900 grams of shellac solids, or any amount by weight of shellac solids between these weights to be established. This variation is due to the fact that shellac is a naturally occurring polymer and therefore 'depending on the growth and treatment conditions varies.

On the other hand, polyvinylpyrrolidone is a synthetic material and can be manufactured with the desired technical data. One mole of basic groups can be contained in 111 g of polyvinylpyrrolidone.

■ The preferred stoichiometric Mo! Ratio of free Carboxyl groups of the Sehellaok to free basic groups that

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Polyvinylpyrrolidone is 111, because of the changes in the However, the acid number of the shellac can be the weight ratio of shellac to polyvinylpyrrolidone in the range from 600 to 900 g Shellac to 111 g of polyvinylpyrrolidone lie.

The weight ratio of other basic polymers shellac can be achieved with knowledge of the stoichiometric composition of the basic polymer can be determined in the same way for a molar ratio of 1 ι 1.

Already an amount as small as 1 percent by weight of polyvinylpyrrolidone, in terms of shellac solids, see as proved suitable for stabilizing the shellac coating film and it has been found that up to 20 percent by weight of polyvinylpyrrolidone, based on shellac solids, give the shellac film a good stability without affecting the desirable stability loses sealing properties of the shellac film. Higher amounts of polyvinylpyrrolidone result in films that are stronger are sensitive to moisture and more permeable to moisture. It has been found that the preferred molar ratio of free acid groups to free basic groups from 1 ι 1 to a concentration of 10 to 15 percent by weight polyvinylpyrrolidone, based on the shellac solids, because the acid content of commercially available shellac fluctuates. This preferred Concentration prevents further esterification and still causes the stabilized shellac film to have the desired barrier properties of the shellac coating film.

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PVP is the preferred basic polymer; it can however, other polymers can also be used, including polyvinylpyrrolidone and polymers made from polymerized linoleic acid Polyamines according to the general formula n-HQOü-R-COOH,

1 1

where R is an alkyl group, plus nH "N-Ä-R -NH ₉ , where R

is an alkylene radical.

The shellac film, which is stabilized according to the invention and forms a dense coating, contains shellac and polyvinylpyrrolidone or another basic polymer in a solvent mixed together in such amounts that a molar ratio of free acid groups in shellac draft-free basic groups in the Polyvinylpyrrolidone of about 1: 1 is present.

One mole of free carboxyl groups can be found in any amount between 600 and 900 grams of shellac solids. den and one mole of free basic groups can be found in 111 g of polyvinylpyrrolidone are in favor. .

The process of making a film-forming sealant Composition as a top coat for tablets and the like includes the following stage: presenting a desired amount of the Shellac, titrating a sample of the shellac to determine the number of moles of s & tire groups in the shellac, adding a such amount ^ polyvinylpyrrolidone to the shellac, which the contains the same number of basic groups and mixing the Sonic lacquer and polyvinylpyrrolidone in a solvent.

The process also includes the process steps of

Mixing a stickiness preventive agent into the

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stabilized Schellaek coating film to prevent picking during the tablet coating process, to prevent the incorporation of a plasticizer into the film to prevent the Increase the flexibility of the film and the mixing of a dye into the film to color the tablets.

The method may further comprise applying successive layers of the film to tablet cores, while these are circulated in a coating kettle. The stabilized shellac coating film seals the cores containing water-sensitive material tightly against moisture, such as from kernels from various drugs were manufactured.

To further Veransehaulichtung the invention are the following examples are given.

example 1 Ingredients quantity

2.72 kg (6 pounds) of purified cut shellac in ethyl alcohol 4.536 kg (160 ounces)

Polyvinyl pyrrolidone. 0.283 kg (10 ounces)

SDA 3-A alcohol 2.891 kg (102 ounces)

The polyvinylpyrrolidone is dissolved in the alcohol and then the shellac is stirred into the mixture. 2.72 kg of the cut, purified shellac in Äthylalkcfhol containing 45% shellac solids, so that in the 4.536 kg 2.041 kg of this ingredient 3chellackfeststoife and 2, 4 $ S kg ethyl alcohol present.

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Example 2 Ingredients quantity

2.72 kg (6 pounds) cut, purified shellac in ethyl alcohol 4.536 kg (160 ounces)

Polyvinylpyrrolidone 0.283 kg (10 ounces)

acetylated monoglyceride 0.283 kg (10 ounces)

SDA 3-A alcohol 3.855 kg (136 ounces)

The polyvinylpyrrolidone and the acetylated monoglyceride A are dissolved in the alcohol and the shellac is then stirred into the solution.

The 2.72 kg of cut, purified shellac in ethyl alcohol contains 45% shellac solids, so in The 4.536 kg of this ingredient has 2.041 kg of shellac solids and 2.495 kg of ethyl alcohol. The acetylated monoglyceride is a plasticizer that reduces the brittleness and increases the flexibility of the stabilized shellac film.

The solutions of Examples 1 and 2 are storage-stable and the films they form on tablets and the like, are very stable after being deposited. The solutions of Examples 1 and 2 can be used to produce a tight seal Coating on tablets, candies, nuts or any solid parts. These solutions can also be used in can also be used effectively to form a film on sugar-coated parts, which has a printable or

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dyeable underlay or a base for applying a Wax coating or a tight seal against penetration of gases and moisture.

Example 3

8.165 kg of sugar-coated tablets were placed in A 18 inch stainless steel kettle is placed and the kettle set in rotating motion, so that the tablets were turned over and set in a tumbling motion. then 30 ml of the solution according to Example 2 were applied to the tablets, by pouring the solution into the kettle. After rotating for a few minutes, the coating dried on the

Tablets without sticking or sticking. The stabilized from this The printing base formed by the shellac coating film did not noticeably delay the time required to dissolve, which was measured immediately after the tablet coatings had dried and also in the course of the following 6 months.

Example 4

2 parts by volume of the solution from Example 2 were mixed with 1 part by volume of -OPASPRAY * while stirring. "OPASPRÄY ¹ · is a solution of officially approved color additives in ethyl alcohol made by Colorcon Inc., West Point, Pa

Unroll tablets. The mixture from the solution of the example

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with the ÖPASPRAY solution of a desired color were applied to the In the kettle agitated tablets sprayed until full color was trained. The tablets were densely coated and glazed (finished) by this single process.

Example 5

Components,

1.814 kg cut shellac in ethyl alcohol

Jetyl alcohol Isopropyl alcohol Sorbitan monooleate (Atlas * Span 80) Sorbitan trioleate (Atlas' Span 85) FD&G yellow Ko, 5 - dye FD&C yellow Ho. 6 - dye titanium dioxide polyvinylpyrrolidone

lot

5.556 kg (196 ounces) g (3.6 ounces)

1.208 kg (42.6 ounces) 161 g (5.7 ounces) 161g- (5.7 ounces)

1.361 kg (48 ounces) 567 g (20 ounces)

1.474 kg (52 ounces) 366 g (13 ounces}

The dyes and titanium dioxide were stirred in the Schell-fj varnish dispersed and the other parts of the bistro then «« set and stirred together * This formulation was poured or sprayed onto the tablets to give an even color over the top to achieve.

The 1,814 kg of crushed shellac in ethyl alcohol contain 37 percent by weight shellac solids, so that of the 5.556 kg of this ingredient 2.055 kg scbell varnish solids and represented 3.501 kg of ethyl alcohol.

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The cetyl alcohol is a stickiness preventive Agent that prevents sticking during the coating process. The isopropyl alcohol serves as the solvent, sorbitan monooleate and sorbitan trioleate are plasticizers which prevent the film from becoming too brittle and which increase flexibility of the film. Span 80 is sorbitan monooleate and Span 85 is sorbitan trioleate manufactured by Atlas Chemical Industries, Inc. Wilmington, Delaware. The organic dyes and titanium dioxide serve as dyes.

Even though the preferred molar ratio of free basic groups of the polymer to free acid groups of the Shellac is 1: 1, as illustrated in Examples 1 to 5, but it has also proven to be such a small amount such as 1 percent by weight of the polymer, based on shellac solids, as valuable in stabilizing the shellac coating film proven. One percent by weight of PVP gives a molar ratio of basic groups in the PVP to free acid groups in the shellac of about 0.1: 1.

In addition, up to 20 percent by weight of the polymer based on the shellac solids has been found to be suitable proved to stabilize the shellac film without impairing the moisture-proof properties of the shellac film get lost. However, above this limit of 20%, the shellac film gradually becomes water sensitive and moisture permeable. This proportion of 20 percent by weight

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PVP gives a molar ratio of basic group dee PVP to free acid groups of shellac from about 1.3 to 1.

Examples of shellac filiae containing 1 to 20 weight percent PVP based on shellac solids will be given below,

Example 6 Ingredients quantity

2.72 kg shellac fraction in ethyl alcohol 4.536 kg (160 ounce «)

Polyvinylpyrrolidone ^ 0.198 kg (7 ounces),

acetylated monoglyceride 0.198 kg (7 ounces)

The polyvinylpyrrolidone is in the shellac solution dissolved and then the acetylated monoglyceride, a plasticizer, stirred into the mixture. The weight ratio of polyvinylpyrrolidone to shellac solids is about 1 ι 10 and that The molar ratio of free basic groups in polyvinylpyrrolidone to free acid groups in shellac is around 0.6 ι 1.

Example 7 Ingredients Men ^ e

2.72 kg shellac fraction in ethyl alcohol 4.536 kg (160 ounces)

Polyvinylpyrrolidone 0.028 kg (1 ounce)

Castor oil 0.283 kg (10 ounce »)

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The polyvinylpyrrolidone is dissolved in the shellac solution and then the castor oil, a plasticizer, is added to the mixture stirred in. The weight ratio of polyvinylpyrrolidone to shellac solids is about 0.14 to 10 and the mole ratio from free basic groups of polyvinylpyrrolidone to free acid groups of shellac is about 0.1 χ 1.

Example 8

Ingredients quantity

2.72 kg shellac fraction in ethyl alcohol 4.536 kg (160 ounces) Polyvinylpyrrolidone 0.396 kg (14 ounces)

acetylated monoglyceride 0.283 kg (10 ounces)

The polyvinylpyrrolidone is dissolved in the shellac solution and then the acetylated monoglyceride is stirred into the mixture. The weight ratio of polyvinylpyrrolidone to shellac solids is about 0.2: 1 and the molar ratio of free basic groups of the polyvinylpyrrolidone to free acid groups of the shellac is about 1.3 t 1.

Besides polyvinylpyrrolidone can be used in conjunction with the · shellac solution also includes other polymeric materials that have basic groups can be used. Such other polymeric materials include polyvinyl pyridine and Polycondensates from polymerized lineal acid with polyamines, according to the general formula n-HOOC-R-COOH, where R

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is alkylene, plus n-HgN-R'-lIHg, where R 'is the residue of an alkyleneamine. The use of such compounds is illustrated in the following examples.

Example 9

Components

2.72 kg of purified roof varnish fraction in ethyl alcohol

Polyvinylpyridine 3-A-alcohol amount

4.536 kg (160 ounces) 0.283 kg (10 ounces) 2.891 kl (102 ounces)

Example 10 Components

2.72 kg of purified roof varnish fraction Monoglyceride acetylated in ethyl alcohol polyvinylpyridine SDA 3-A alcohol

Example 11 Components

1.814 kg of shellac fraction in ethyl alcohol

Cetyl Alcohol Isopropyl Alcohol Sorbitan Monooleate (Atlas' Span 80) quantity

4.536 kg (160 ounces) 0.283 kg (10 ounces) 0.283 kg (10 ounces) 2.891 kg (102 ounces)

lot

5.556 kg (196 ounces) 0.102 kg (3.6 ounces) 1.361 kg (42.6 ounces) 0.161 kg (5.7 ounces)

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Ingredients quantity

Sorbitan trioleate (Atlas' Span 85) 0.161 kg (5.7 ounces)

FD&C yellow No. 5 - dye, 1.361 kg (48 ounces)

FD&C yellow No. 6 - dye 0.567 kg (20 ounces)

Titanium dioxide 1.474 kg (52 ounces)

Polyvinylpyridine 0.368 kg (13 ounces)

Example 12

Components Quantity e

2.72 kg of purified shellac fraction

in ethyl alcohol ■ 4,536 kg (160 ounces)

Polyamide Versamid 125 0.567 kg (20 ounces)

SDA 3-A alcohol 2.891 kg (102 ounces)

Polyamide Versamid 125 is a polyamide resin manufactured by General Mills, Inc. that is obtained by condensation of
Polyamines such as diethylenetriamine with a polymeric fatty acid known as dimer acid, the main component of which is a dibasic acid having 36 carbon atoms. She is in The Inherent Corrosion-Inhibiting Properties c? the Polyamide-Epoxy-Vehicle ", Witteoff and Baldwin, Journal of Paint Technology, Volume 38,
No. 500, February 1966, pages 556-563.

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Claims (13)

Example 13 Ingredients Amount 2.72 kg of purified shellac fraction in ethyl alcohol 4.536 kg (160 ounces) polyamide Versataid 140 0.567 kg (20 ounces) SDA 3-A alcohol 2.891 kg (102 ounces) polyamide Versamid 140 is another polyamide resin from General Mills, Inc. and is described in the referenced publication. In the attached drawing, a table or pill designed according to the invention is shown in cross section in perspective. The tablet core containing a water-sensitive material is denoted by 1 herein. The core is enclosed by a tightly sealing moisture-impermeable film 2 made of one of the coating compounds specified above. CHECK OUT 1. Gas and moisture impermeable coating compound for Tablets and the like containing a polymeric material with free basic groups and shellac with free acid groups in a Mo! ratio of free basic groups to shellac free acid groups of about 1 s 1, 0Ü9883 / 2078 2. Coating compound according to Jlnspruch 1, thereby g e k β η η ζ ei chnet that they are polyvinylpyrrolidone as a polymeric material contains. 3. Coating composition according to claim 1, characterized in that it is polyvinylpyridine as the polymeric material contains. 4. Coating composition according to claim 1, characterized in that it is a polyamide resin as the polymeric material contains. 5. Coating composition according to claim 1 or 4, characterized in that it is used as a polymeric material a polymer of polymerized lineal acid with polyamines contains, these compounds having the formulas n-HOOC-R-COOH, in which R is an alkylene group and n-HgN-R'-NtL, wherein R 'is the residue of an alkyleneamine. 6. Coating composition according to claim 1, characterized in that it is polyvinylpyrrolidone as the polymeric material contains and the weight ratio of shellac to polyvinylpyrrolidone about 600 to 900 parts of shellac is about 111 parts of polyvinylpyrrolidone. 7. coating composition according to claim 1 to 6, characterized in that it is used as a polymeric material ' Polyvinylpyrrolidone in an amount of about 10 parts by weight of polyvinylpyrrolidone to about 72 parts by weight of shellac. 009883/2078 8. Coating composition according to claim 1, 2, 6 or 7, characterized g e k en η ze i c h.n.e.t that they are about 72 1/2 weight steep Shellac contains about 13 parts by weight of polyvinylpyrrolidone, 9. About Zugsnasse according to claim 1, ge k e η η ζ e i c h η e t by a content of 5.556 kg of a solution of 1.814 kg Shellac fraction in ethyl alcohol, 0.102kg cetyl alcohol, 1.361 kg isopropyl alcohol, 0.161 kg sorbitan monooleate, 0.161 kg Sorbitan trioleate, 1.361 kg dye FD&C Yellow Ur. 5, 0.567 kg Dye TÖ & C Yellovi Hr. 6, 1.474 kg of titanium dioxide and 0.368 kg Polyvinylpyrrolidone, 10. Process for the production of a coating wet Claims 1 to 9, characterized in that by titrating a sample of the shellac, the number of moles of notes free acid groups in the shellac to the desired Amount of shellac such an amount of a polymeric material are, which has the same number of moles of free basic groups and these ingredients in a solvent mixed together. 11. The method according to claim 10, characterized in that g e k e η η, that polyvinylpyrrolidone, polyvinylpyridine or a polyamide resin are used as the polymeric material. 12. The method according to claim 10 or 11, characterized in that the coating mass is a non-life preventing agent, a plasticizer and a V arbstof; "to see. 13. Tablet for oral administration, characterized in that a tablet core containing a water-sensitive ^ dterial, is surrounded by a tightly sealing, moisture sundurchlässigen film of according to any one of claims 1 to ¹ J composite coating composition. 0 0988 ^ / 2078 BAD ORfQtNAL