* GB786154 (A)

Description: GB786154 (A) ? 1957-11-13

Improvements relating to electric switch operating mechanisms

Description of GB786154 (A)

PATENT SPEUFICATIOIN 7 Date of filing Complete Specification: Dec 15, 1953. X) Application Date: Sept 16, 1952 No 23262152. Complete Specification Published: Nov 13, 1957. Index at Acceptance:-Class 38 ( 5), B 1 F 3, B 2 A( 5 A 5: 7: 18), B 2 B 10, B 2 C 602. International Cla Ssification:-H 01 n H 02 c. COMPLETE SPECIFICATION. Improvements relating to Electric Switch Operating Mechanisms I, SIDNEY GEOFFREY YOUNG, of 154 Blackfriars Road, London, S E 1, a British Subject, do hereby declare the invention, for which I pray that a patent may be granted to me, and the method by which it is to be performed, to be particularly described in and by the following statement:- This invention relates to improvements in electric switches of the type operated by successive unidirectional movements of an actuating member, and is directed more particularly to switches of the ceiling type operated by a cord. The primary object of the invention is to provide a simplified construction involving fewer than the number of parts usually employed in such switches, with consequent economies in manufacture and assembly, while retaining a mechanism both simple and reliable in operation. The contact operating mechanism employed in the improved switch is operated by a pivotally arranged operating member, the exact structure of such mechanism forming no part of the present invention Preferably, however, the control mechanism will be of a snap-action type employing a resilient "snapper" such as is described in one of my prior Patents Nos 594,114, 654,715, 645,716 and 669,969 The present invention is concerned with the mechanism whereby the pivoted operating member or

"dolly" is caused to swing back and forth by the actuating member the movement of which consists of a number of successive substantially linear movements in the same direction Thus, for example, the operating dolly is firstly moved to one extreme position, e g to close a circuit, by a linear movement of the actuating member in a given direction, usually away from the dolly. This is followed by a reverse movement of the actuating member back to its original r Pr Zl Ce 3 s 6 ff-ji QC,;, A, se position, normally as a result of spring pressure, the dolly remaining unaffected. Movement of the dolly back to its original position, e g to reopen the circuit, is then caused by a second movement of the actuating member in the same direction as the first such movement Finally the actuating member again returns to its original position without affecting the position of the dolly and the cycle is completed. Many mechanisms accomplishing this change of motion from successive unidirectional movements to reciprocating swinging movements have already been manufactured, but they have all suffered from complexity of construction which has led to unreliable operation or high cost of manufacture. The present invention provides mechanism in which only three parts are required to operate the dolly One of these is the actuating member to which is connected a cord or push-button or other external operating part depending on whether the switch is to be the pull-pull or push-push operating type; the second part is a spring arranged to return the actuating member to its original position after each operative stroke; and the third part is a swinging link interconnecting the rectilinearly moving actuating member and the pivoting dolly. One form of construction in accordance with the invention is illustrated in the accompanying drawing by way of example. In this drawing:Fig 1 shows a central section through a switch of the "ceiling" type; Fig 2 shows a view of the same switch as Fig 1 taken on a central section at right angles to that of Fig 1; and Fig 3 shows a plan view separately of the swinging link used in the switch of Figs. 1 and 2. This swinging link 1 takes the form of a 6,6954 786,154 small piece of stiff material such as sheet metal stamped or otherwise cut out to provide, essentially, a hook portion 2 adapted to engage in a slot 3 in the dolly 4 and a base portion 5 adapted to be journalled in a recess 6 or like aperture formed near the end of the actuating member 7 This base portion 5 extends transversley to the longitudinal axis of the actuating member 7 sufficiently to bear at its ends against the end coil of a helical spring 8 (constituting the above mentioned

second part), such spring 8 being disposed around the actuating member 7 and advantageously being of low rate As shown, the actuating member is preferably in the form of a flat elongated piece of stiff material such as sheet metal having at one end the aforementioned aperture 6 bearing the swinging 0 link 1 and at the other end means for engaging a cord. In accordance with a further optional feature of the invention as described and claimed in my Application No 10044/56 (Serial No 786,155) and best seen in Fig 2, such cord engaging means comprise a bent portion 9 of the actuating member 7 itself extending at an angle of about 45 from the main plane of such member and then transversely to such plane to intersect the same. A key-hole type slot 10 (Fig 1) is provided in this bent portion 9, the circular part of the slot being adjacent the unbent part of the member 7 A cord (not shown) terminating in a knot can then be slipped into this slot 10, the knot passing through the circular part and finally being drawn by tension in the cord against the thin portion of the slot through which it cannot pass The cord will then lie substantially in a continuation of the plane of the actuating member 7 while its knot bears stably against a surface transverse thereto. These three parts are housed in a cylindrical housing 11 having a slot 12 along which the actuating member 7 may slide and an inner annular surface 13 supporting the helical spring 8, this housing 11 being arranged for connection by screws 14 to the main housing 15 containing the dolly 4, the snapper 16 and its associated contacts and terminals A cover 17 is screwed onto the housing 11. In operation, the actuating member 7 when pulled by the cord transmits this tractive force to the swinging link 1 through the end portion 18 of itself beyond the aperture 6, such end portion forming in effect a hook since the aperture is open at one side of the member to enable the parts to be assembled This tractive force is in turn transmitted through the hook portion 2 of the swinging link 1 to the dolly 4, the slot 3 of which has a recess 19 at each end in its surface nearer to the swinging link and the actuating member As the dolly 4 is swung from one position to the other, one end of the slot 3 (and therewith one of the said recesses 19) is brought approximately into register with the plane along which the O actuating member 7 slides, while the other end of the slot occupies a position to the side of such plane and more remote from the actuating member When the snapper 16 is snapped over, the dispositions of the ends 75 of the slot 3 relative to the actuating member 7 are effectively reversed Prior to the first pull on the actuating member 7, the hook 2 of the swinging link 1 engages that recess 19 in the slot 3 of the dolly 4 which 80 is then "remote" as explained above, i e.

as seen in Fig 1 When the tractive force is then applied through the hook 2 of the swinging link 1, the remote end of the dolly slot is thus drawn towards the central plane 85 of the switch, i e that along which the actuating member slides This results in snapping over the snapper 16 or other switching mechanism that may be employed, and reorientation of the dolly 4 in its new 90 position. The next stage in the operation is release of the actuating member 7 by relaxation of the tension in the cord by which it is pulled. Return of the actuating member 7 is brought 95 about by the spring 8 acting through the transverse base portion 5 of the swinging link 1 At first both the swinging link 1 and the actuating member 7 move rectilinearly, until the hook portion 2 of the swinging link 100 1 bears against the remote surface 20 of the slot 3 in the dolly 4 This surface 20 is smoothly curved to guide such hook portion 2 along the slot 3 and in so doing to commence to rotate the swinging link 1 in its 105 bearing in the aperture 6 in the end of the actuating member 7, such aperture 6 preferably being substantially triangular in shape as illustrated, to facilitate such action This rotation of the swinging link 1 inclines the 110 centre lines of such swinging link 1 and the actuating member 7 to each other, until finally the transverse base portion 5 of the swinging link 1 is in compression transmitting the force of the spring 8 to the portion 115 18 of the actuating member 7, is sharply turned sideways like a toggle Its sideways movement is however limited by the freedom of its hook portion 2 in the dolly slot 3, and the parts thus come to rest with the 120 plane of the swinging link 1 inclined at about to the centre line of the actuating member 7, and the hook portion 2 of such link at the "remote" end of the dolly slot 3 i e. as shown in Fig 1 except that the parts are 125 in the reverse position. When the actuating member 7 is again pulled to effect reversal of the switch, such hook portion 2 engages the recess 19 at the "remote" end of the slot 3 and an operation 130 formed from sheet material to have a hook portion engaging a slot in the operating member and a base portion mounted for swinging movement in a cavity at one end of the actuating member, such base portion extending transversely to engage the end coil of a helical spring.

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* 5.8.23.4; 93p

* GB786155 (A)

Description: GB786155 (A) ? 1957-11-13

Improvements relating to card-operable electric switches

Description of GB786155 (A)

PATENT SPECIFICATION Dotse j',ll 'lg >,ilete Specificatiot: D Tc 1 5, 195:. A 1,pbuil l'ia,, little: Sept 16, 195 X) 100 f 4- 5 ( 6 (Dii 7 idd out of No 786 154 f.'o)) i R c; icatio)n Pi Thlis,?ed: o 13 19 5 >. Indlex at Aeeeptancee:-Classes 3 B\ 5 \, B 2 A 18; 44, BE( 12: 13 B); and 109, D 3 B 2. International Classification:-D 07 F 06 b HO 2 c. COMPLETE SPECIFICATION. EREPATET. SFECIFICATION NO 786,1 n-5 Page 1, Title, for "Card-Cperabletr read n Cord-Operatle". THE PATETT OFFICE, 21 St Airil, 1958 DB 0437 T/2 ( 7)/3 C 011 'A transiationai movement is imparrea to mne actuating member and the switch is operated; wherein the actuating member comprises a rigid member having a key-hole slot for the reception and engagement of a knotted end of the cord. Preferably, in the switch of the invention, that portion of the actuating member in the 2.5 region of the key-hole slot is so formed that the reduced portion of the slot extends in a direction transverse to and intersecting the path of movement of the actuating member. In the switches of the invention, a knot already tied in the end of a cord can readily be pressed into or out from the enlarged part of the key-hole slot in the actuating member and tension applied to the cord to draw the knot along the reduced portion of the slot wherein it is firmly engaged As will be appreciated the use of a key-hole slot avoids the necessity of forming a knot in the end of a flexible cord after passing such end through a hole in the actuating member to which it is to be connected. The accompanying drawing shows a preferred form of actuating member

for use in lPrice 3 s 6 d l eniargea part or sucn siot iying in -u y ition 8 and the reduced portion of such slot in the portion 10 A cord (not shown) terminating in a knot can be slipped into the slot 10, the knot passing through the enlarged part and then being drawn by tension in the cord against the portion 9, being unable to pass through the reduced portion of the slot 10 in such portion 9 The cord will then be substantially in a continuation of the plane of the plate 7 with its knot bearing stably against a surface transverse thereto While the knot and thus the cord is clearly held securely by the improved connection against accidental displacement or disconnection, it can readily be disconnected by slipping the knot back through the enlarged portion of the slot 10, without the necessity, normally encountered, of cutting away or untying the knot.

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* GB786156 (A)

Description: GB786156 (A) ? 1957-11-13

Morphine derivatives and processes for producing them

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PATENT SPECIFICATION

786, 156 he Date of Application and filing Complete Specification: May 12, 1954. __ No13937154. Application made in United States of America on June 2, 1953. ___g D Complete Specification Published: Nov 13, 1957. Index at acceptance:-Class 2 ( 3), C 3 A 6, C 3 AMOE( 3 A 4: 3 C 4: 5 A: SE), C 3 A 13133. International Classification:-CO 7 d. COMPLETE SPECIFICATION Morphine Derivatives, and Processes for producing them We, MERCK & Co, INC, a corporation duly organised and existing under the laws of the State of New Jersey, United States of America, of Rahway, New Jersey, United States of America, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement: - This invention relates to morphine derivatives In brief, this invention provides novel \ 6-desoxymorphine compounds having an aryl or lower alkyl substituent attached to the carbon atom in the 6-position of the molecule, and a carboalkoxy or carboaralkoxy group on the oxygen atom attached to the carbon atom in the 3-position of the molecule, salts of the said compounds, and processes for preparing such compounds and removing the 03 substituent from them to produce A 6-desoxymorphine compounds having an aryl or lower alkyl substituent attached to the 6-carbon atom In the specification of Patent No. 738,207 ( 12826/53), A 6-6-(lower alkyl)-desoxymorphine compounds and their salts and alkanoyl esters are claimed per se. In the present specification, the term "lower alkyl " is to be understood as denoting allyl groups containing not more than 5 carbon atoms. The novel compounds of the invention may be represented by one of the following formulae: wherein R is an aryl or lower alkyl substituent, R' is carboalkoxy or carboa 1:alkoxy, and HA is anacn lPrice 3 s g-Are I I The chemical relationship of the novel compounds to morphine is clear from a comparison of the foregoing formulae with the 40 structural formula of morphine which is as follows: Although the alkaloid morphine has for centuries been known to possess analgesic activity, the contribution of each and every characteristic portion of this complex molecule to the analgesic and narcotic properties is still not fully understood Extensive research has established the chemical structure of this important narcotic, and has given some indications as to the effect of certain structural characteristics on analgesic activity.

There is no way known, however, for predicting the pharmacological properties of derivatives prepared by introducing new substituents at various points in the morphine nucleus The 6-alkyl-A 6-desoxymorphines, and their lower alkanoyl esters, and salts, have been found very much more active than morphine For example, 6-methyl-A 6-desoxymorphine has been found to possess over one hundred times the analgesic activity possessed by morphine itself Moreover, 6-methyl-AA 6desoxymorphine possesses, in addition to its extremely high potency, an extraordinary promptness of onset of analgesic action. An improved synthesis of A'-desoxymorphine compounds having a lower alkyl or aryl substituent attached to the carbon atom in the 6-position of the molecule was desired, since the processes originally developed involved prolonged periods of heating at elevated temperatures and pressures with large excesses of the reactants. A vastly improved procedure for the preparation of these valuable compounds has now been developed which greatly increases the yield of the product and simplifies operation conditions considerably. Regarded-in certain of its broader aspects, the process of the present invention involves esterification of the phenolic hydroxyl group of a 6-(lower alkyl) or 6-aryl-dihydromorphine to form an 03-acyl-6-(lower alkyl)-dihydromorphine or an O'-acyl-6-aryl-dihydromorphine, dehydration of the ester to produce an 0 '-acyl-6-(lower alkyl)-i; 1 '-desoxymorphine or an O '-acyl-6-aryl-A 6-desoxymorphine compound and hydrolysis of the latter compound to form the desired 6-(lower alkyl)-1-desoxymorphine or 6-aryl- -i Y-desoxymorphine This process can be chemically represented as follows: Io to 42 t'ff D1 OARP Onv 2 ' El YSS C Ol AMD/N 1 3 Co Mvp M 1 i', 4 where R represents a lower alkyl or aryl radical and R' represents an acyl radical The first step forms part of the invention claimed in the specification of our copending application No 6447/57 (Serial No 786,157) The term " acyl " as used throughout the specification and claims includes the residue of a carboxylic acid, such as acetyl, as well as carboalkoxy and carboaralkoxy. An O ' acyl 6 (lower alkyl) dihydromorphine or 0 '-acyl-6-aryl-dihydromorphine, which can be prepared by the method described and claimed in the specification of our copending application 6447/57 (Serial No. 786,157), can be dehydrated to form an 0-acyl-6-(lower alkyl)-6 \ 6-desoxymorphine or an O '-acyl-6-aryl-A 6-desoxymorphine by using as dehydrating agent one of the phosphorus, sulphur, or acyl halides Example of suitable dehydrating agents include compounds such as phosphorus tribromide, phosphorus trichloride, thionyl chloride, thionyl bromide, phosphorus pentachloride, sulphuryl chloride, sulphuryl bromide and acetyl chloride.

The dehydration reaction can be carried out in solution in pyridine, water, or organic solvents having no reactive hydrogen atoms. Pyridine is preferred, and when it is used as solvent, the reaction is conveniently run at room temperature, although when solvents other than pyridine are used, slightly higher temperatures are preferred; for example, when chloroform is employed the mixture is held at reflux temperature for approximately eighteen hours The temperature and the length of reaction time are dependent upon each other and on the choice of solvent It is possible to carry out the reaction between about room temperature and 1000 C using times of from six to twenty-four hours. It is not necessary that the O '-acyl-6-(lower alkyl)-dihydroi-nrphiine or O-acyl-6-aryl-dihydromorphine be a pure crystalline material although the best yields are obtained when pure material is used As an alternative method, the crude 03-acyl-6-(lower alkyl)dihydromorphine or 0-acyl-6-aryl-dihydromorphine may be treated with the dehydrating agent without further purification In order to further simplify the process of this invention it is possible to esterify the phenolic hydroxyl group and dehydrate at the 6-7 positions without isolation of intermediates by employing a reagent, such as an acyl halide, e g. acetyl chloride, which will cause both reactions to take place. Removal of the acyl group from the O'-acyl-6-(lower alkyl)-\-desoxymorphine or 0 '-acyl-6-aryl-A',-desoxymorphine e g by hydrolysis or alcoholysis, to yield 6-(lower alkyl)-AL 6-desoxymorphine or 6-aryl-A&-desoxymorphine may be carried out using either acid or alkaline reagents in aqueous, anhydrous organic, or aqueous organic solvent. Alkaline hydrolysis may be conducted using alkali or alkaline-earth metal oxides, hydroxides, alkoxides or carbonates, and acid hydrolysis may be effected using any of the common mineral acids in dilute aqueous solution When using an alkali, alcoholysis by 786,156 morphine was dissolved in 50 mnl of 95 % alcohol and 2 grams of potassium hydroxide and a small volume of water was added After refluxing the solution for 30 minutes in a nitrogen atmosphere, the p H of the mixture was adjusted to 9 The alcohol was removed by evaporation in vacua and the residual 6methyl-A 6-desoxymorphine was extracted into chloroform The chloroform extract was dried and concentrated in vacuc The residue was crystallized from ethyl acetate to yield 1 38 grams of 6-methyl-A 6-desoxymorphine having a melting point of 227 -229 C-, 'm"= -221 C ( 1 % absolute alcohol) Recrystallization from the same solvent raised the melting point to 236-237 C. EXAMPLE 2. Preparation of O '-carbomethoxy-6-MethylA\-Desoxymorphine.

A mixture of 2 4 g of O '-carbomethoxy6-methyldihydromorphine, prepared as in Example 1 of specification No 6447/57, 25 ml of pyridine and 2 ml of thionyl chloride was prepared and allowed to stand at room temperature for 24 hours The mixture was then decomposed on ice and the p H adjusted to 8 5 with sodium bicarbonate It was then extracted with chloroform and the chloroform extract concentrated in vacua to an oil The oil was then leached with 100 ml of boiling ether, filtered, and the ethereal filtrate concentrated to give as a solid product O'-carbomethoxy-6-methyl E-6-desoxymorphine, having a melting point of 135 -140 C. heating with alcoholic potassium hydroxide at temperatures below about 1000 C for approximately fifteen minutes is a preferred process It is preferable to maintain an atmosphere of nittogen during the alkaline alcoholysis reaction in order to minimize decomposition and achieve maximum yields The alcoholysis may be carried out between the temperatures of 25 '-1250 C over a period of from a few minutes to 24 hours. Dilute acid hydrolysis is the normally preferred procedure since the acid addition salt of 6-methyl-Z\ 6-desoxymorphine may be readily isolated from the reaction mixture and the salt is the preferred form of the compound for therapeutic administration rather than the free base Thus, following acid hydrolysis of the O'-acyl-6-(lower alkyl)-AY-desoxymorphine, the desired acid addition salt of 6(lower alkyl)-A 6-desoxymorphine may be obtained by concentrating the aqueous solution and allowing the product to crystallize For example, 6-(lower alkyl)-A 6-desoxymorphine acid addition salts such as the 6-(lower alkyl)16-desoxymorphine hydrochloride, 6-(lower alkyl)-A\-desoxymorphine sulfate, 6-(lower alkyl)-AG-desoxymorphine hydrobromide or 6(lower alkyl)-A 6-desoxymorphine phosphate may be prepared preferably by contacting the Os acyl 6-(lower alkyl)-/A 0-desoxymorphine compound with a dilute aqueous solution of the appropriate mineral acid at not higher than 1000 C for approximately one to three hours The 6-aryl-A 6-desoxymorphine addition salts may be prepared in like manner. Although the elevated temperature may be necessary to effect ester hydrolysis, the formation of the acid addition salt takes place readily at room temperature. The following examples illustrate methods of carrying out the present invention, but it is to be understood that these examples are given primarily by way of illustration and not of limitation. EXAMPLE 1. Preparation of 03-Carbomethoxy-6-MethylA 6-Desoxymorphine. 3 g of O '-carbomethoxy-6-methyl dihydromorphine, prepared as in Example 1 of specification No 6447/57 (Serial No.

786,157), was dissolved in 100 ml of absolute chloroform and 3 ml of thionyl chloride was added dropwise with stirring ( 250 C) The colorless solution was stirred at room temperature for one hour and then refluxed for seven hours The chloroform solution was then poured onto crushed ice and the p H of the resulting mixture was adjusted to 9 with potassium hydroxide The mixture was then extracted with chloroform and the chloroform extract concentrated in vacuo to yield 03carbomethoxy-6-methyl-ZA 6-desoxymorphine. Preparation of 6-Methyl-A,-Desoxymorphine. The O '-carbomethoxy-6-methyl-A 6-desoxyPreparation of 6-Methyl-A 6-Desoxymorphine Alkaline Hydrolysis 100 The O '-carbomethoxy-6-methyl-A,-desoxymorphine was heated with 2 g of sodium hydroxide and dissolved in aqueous alcohol for about 30 minutes The alcohol was then removed from the mixture by evaporation 105 under reduced pressure and the product, 6-me-thyl-Al-desoxymnor Dhine, was extracted into chloroform and the chloroform extract concentrated to an oil Trituration of the residual oil resulted in 1 33 g of crystalline 110 6-methyl-A 6-desoxymorphine having a melting point of 2280-2320 C The product was then recrystallized from ethyl acetate to yield a product having a melting point of 236 2370 C, a D= 2270 ( 1 % absolute alcohol) 115 Analysis calculated for: C 18,H,ON ( 283 3): C, 75 28; H, 7 47; N, 4 94; Found: C, 76 43; H, 7 40; N, 5 14. EXAMPLE 3. Preparation of 0 '-Carboethoxy-6-Methyl-A/ 120 Desoxymorphine. 2.7 g of 03-carboethoxy-6-methyl-dihydromorphine, prepared as in Example 2 of specification No 6447/57 (Serial No 786,157), was dissolved in 100 ml of alcohol-free 125 chloroform and 3 ml of thionyl chloride was added dropwise The solution was then refluxed overnight Addition of another small 786,156 volume of thionyl chloride did not release more hydrogen chloride gas; hence, reaction was complete The chloroform solution was then poured onto crushed ice, and the p H of the resulting mixture was adjusted to 9 with potassium hydroxide The mixture was then extracted with chloroform and the chloroform extract concentrated in vacuo to yield 03carboethoxy-6-methyl-A 6-desoxymorphine. Preparation of 6-Methyl-'Y-Desoxymorphine. The crude O-carboethoxy-6-methyl-A'-desoxymorphine obtained as described above was dissolved in 50 ml of 95 % alcohol and 1 g. of potassium hydroxide in a small volume of water was added After refluxing the solution for 30 minutes in a nitrogen atmosphere the p H of the mixture was adjusted to 9, the alcohol was removed by evaporation in vacuo and the residual crude 6-methyl-A 6-desoxymorphine was extracted into chloroform The chloroform extract

was dried and concentrated in vacuo The residue was crystallized from ml of ethyl acetate to yield 1 27 g of essentially pure 6-methyl-A 6-desoxymorphine having a melting point of 225 -229 ' C, = -215 C ( 1 %' absolute alcohol) Concentration of the solvent and chilling yielded a second crop of 0 27 g of 6-methyl-'\ 6-desoxymorphine Further purification raised the melting point to 235 -237 C. Analysis calculated for: C 1 f Hfl ON ( 203 3): C, 76 28; H, 7 47; N, 4 94; Found: C, 76 31; H, 7 40; N, 4 81. 6 Methyl G desoxymorphine hydrochloride melted at 288 -289 C, D 425 = 1860 C ( 1 % absolute alcohol) and was anhydrous after crystallization from alcoholether and drying at 1000/1 mm. The 6-methyl-A 6-desoxymorphline hydrobromide decomposed at 293 -297 C, t D 25 1670 C (C= 0 6, methyl alcohol). Ex AMPLE 4. Preparation of O '-Carboethoxy-6-Ethyl-A/Desoxyrnorphine. 03 carboethoxy-6-ethvl-dihydromorphine, prepared as described in Example 3 of specification No 6447/57 (Serial No 786,157) was dissolved in alcohol-free chloroform and 1 ml of thionyl chloride was added dropwise. The solution was then refluxed for 15 hours. The chloroform solution was then poured onto crushed ice and the resulting mixture was adjusted to p H 9 with potassium hydroxide The mixture was then extracted with chloroform and the chloroform extract concentrated in va Cuo to yield O '-carboethoxy-6ethyl-AY-desoxymorphine. Preparation of 6-Ethyl- 'L-Desoxymorphine. The crude 06-carboethoxy-6-ethyl-^\-desoxymorphine was dissolved in 95 % alcohol and potassium hydroxide and a small volume of water was added After refluxing the solution for 30 minutes at 1000 C under a nitrogen atmosphere the p H of the mixture was adjusted to 9 The alcohol was removed by evaporation in vacuo and the residual crude 6-ethyl-A 6-desoxymorphine was extracted into chloroform The chloroform extract was dried and concentrated in vacuo The residue was crystallized from ethyl acetate to yield 0 51 grams of 6-ethyl- A-desoxymorphine, having a melting point of 119 -121 C One further crystallization from ethyl acetate raised the melting point to 122 '-124 ' C, = 1850 C ( 1 % absolute alcohol) Addition of a slight excess of alcoholic hydrogen bromide to the base gave the crystalline 6-ethyl-A\ 6desoxymorphine-hydrobromide having a melting point of 277 -284 ' C (decomposed). The analytical sample was dried at 780/1 mm. Analysis calculated for: CH,,H 2 ON Br ( 3783): C, 60 32; H, 6 39; Found: C, 59 62; H, 6 13.

EXAMPLE 5. Preparation of O-Carboethoxy-6-Phenyl-A 6 85 Desoxymorphine. 0 carboethoxy 6 phenyl dihydromorphine, prepared as in Example 4 of specification No 6447/57, was dissolved in alcohol-free chloroform and thionyl chloride 90 was added dropwise to this mixture The solution was then refluxed overnight The chloroform solution was then poured onto crushed ice and the p H of the resulting mixture was adjusted to 9 with potassium 95 hydroxide The mixture was then extracted with chloroform-and the chloroform extract concentrated in vacuao to yield 0-carboethoxy-6-phenyl-Al \-desoxymorphine. Preparation of 6-Phenyrl 16-Desoxymorphine 100 1.3 g of O '-carboethoxy-6-phenyl-A\ 6-desoxymorphine was dissolved in 15 ml of 95 %O alcohol containing 1 g of potassium hydroxide pellets, and 2 ml of water was added After refluxing the solution for 30 minutes in a 105 nitrogen atmosphere, the p H of the mixture was adjusted to 9 The alcohol was removed by evaporation in vacua and the residual crude 6-phenyl-A 16-desoxymorphine was extracted into chloroform The chloroform extract was 110 dried and concentrated in vacuo to yield 6-phenyl-A\-desoxymorphine Dissolution of the residue in alcoholic hydrogen chloride yielded 6-phenyl-A 6-desoxymorphine hydrochloride, melting point 265 -210 ' C (dec), 115 D 25 = -287 ' C ( 1 absolute alcohol). EXAMPLE 6. Preparation of 0-Carbobenzoxy-6-MethylA 6-Desoxymorphine. The crude O '-carbobenzoxy-6-methyl-di 120 hydromorphine obtained by the process of Example 5 of specification No 6447/57 (Serial No 786,157), was dissolved in 100 ml. of absolute chloroform and 2 ml of thionyl chloride was added The mixture was refluxed 125 overnight The chloroform solution was then poured onto crushed ice and the p H of the 786,156 specification No 6447/57 (Serial No. 786,157), was dissolved in absolute chloroform and 3 ml of thionyl chloride was added dropwise The solution was then refluxed for hours at 65 C The chloroform solution was poured onto crushed ice and the resulting solution was adjusted to p H 9 with potassium hydroxide The mixture was then extracted with chloroform and the chloroform extract concentrated in vacuo to yield O'-carboethoxy-6-butyl-A 6-desoxymorphine. resulting mixture was adjusted to 9 with potassium hydroxide The mixture was then extracted with chloroform and the chloroform extract concentrated in vacuo to yield O 'carbobenzoxy-6-methyl d 6-desoxymorphine. Preparation of 6-Methyl-A 6-Desoxymorphine. The crude O '-carbobenzoxy-6-methyl-A 6desoxymorphine was dissolved in

50 ml of % alcohol and one gram of potassium. hydroxide and a small volume of water was added After refluxing the solution for 30 minutes in a nitrogen atmosphere, the p H of the mixture was adjusted to 9 The alcohol was removed by evaporation in vacuo and the residual crude 6 methyl _ desoxymorphine was extracted into chloroform The chloroform extract was dried and concentrated in vacuo The residue was crystallized from 30 ml of ethyl acetate to yield 0 4 grams of essentially pure 6 methyl desoxymorphine having a melting point of 225 2300 C. EXAMPLE 7. Preparation of 03-Acetyl-6-Methyl-A 6Desoxymorphine. 0.5 g of 0 ' acetyl -6 methyl dihydromorphine, obtained as in Example 6 of specification No 6447/57 (Serial No. 786,157), 0 5 ml of thionyl chloride and 10 ml of pyridine were mixed and allowed to stand at room temperature for 24 hours The resulting brown solution was decomposed on ice, the p H adjusted to 8 5 with sodium bicarbonate and the mixture extracted with chloroform The chloroform extract was water washed, dried and concentrated in vacuo to remove the chloroform The concentrate, 0.25 g of 0 '-acetyl-6-methyl-A 6-desoxymorphine, was crystallized from ether to yield a pure 03-acetyl-6-methyl-A 6-desoxymorphine, having a melting point of 1700 C, a J 25 = _ 229 C ( 1 % absolute alcohol). Analysis calculated for: C O H,0,H; C. 73.82: H, 7 12; N, 4 31; Found: C, 73 76; H, 7 13; N, 3 92. The 03-acetyl-6-methyl-A 6-desoxymorphine hydrochloride melted at 2850-290 C. Preparation of 6-Methyl-A 6-Desoxymorphine. Approximately 200 mg of O-acetyl-6methyl A 6-desoxymorphine was heated with 0.5 g of potassium hydroxide in dilute alcohol for 30 minutes on a steam bath The mixture was adjusted to p H 9 and extracted with chloroform The chloroform extract was concentrated in vacuo and the crude product recrystallized twice from ethyl acetate to yield pure 6-methyl-A 6-desoxymorphine, having a melting point of 236 -237 C. EXAMPLE 8. Preparation of O'-Carboethoxy-6-Butyl='Desoxymorphine. 4 g of 0-carboethoxy-6-butyl-dihydromorphine, prepared as in Example 7 of Preparation of 6-Butyl A 6-Desoxymorphine 75 The crude O '-carboethoxy-6-butyl- A 6-desoxymorphine was dissolved in a solution of 3 g of sodium hydroxide in 70 ml of 50 % alcohol and containing a trace of sodium bisulphite After refluxing the solution under a 80 nitrogen atmosphere, the p H of the mixture was adjusted to 9, the alcohol was removed by evaporation in vacuo and the residual crude 6-butyl,6-desoxymorphine was extracted into chloroform The chloroform extract was dried 85 and concentrated in vacuo The residue was

crystallized from ethyl acetate to yield 6butylh\-desoxymorphine, having a melting point of 167 -169 C, a"= _ 213 C. ( 1 % absolute alcohol) 90 Analysis of a sample dried in vacuo indicated solvation Hence, a small portion was sublimed at 180 C /1 mm. Analysis calculated for: C 21 H 2702 N ( 325 4): C, 77 50; H, 8 36; N, 4 30; Found: 95 C, 77 59; H, 8 40; N, 4 56.

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* GB786157 (A)

Description: GB786157 (A) ? 1957-11-13

Morphine derivatives

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PATENT SPEFCATION PATENT SPECIFICATION Date of Application and filing Complete Specification: May 12, t& t No 6447/57. Application made in United States of America on June 2, 1953. (Divided out of No 786,156). ,os'' Complete Specification Published: Nov 13, 1957.

Index at acceptance:-Class 2 ( 3), C 3 A 6, C 3 A 7 (A 4: C: El: H: J 1), C 3 A 13 D. International Classification:-CO 7 d. COMPLETE SPECIFICATION Morphine Derivatives We, MERCK & CO, INC, a corporation duly organised and existing under the laws of the State of New Jersey, United States of America, of Rahway, New Jersey, United States of America, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement:This invention relates to morphine derivatives. In brief, this invention provides dihydromorphine compounds of the general formula OR' 4 u E in which R represents lower alkyl or aryl and R 1 represents acyl, the term " acyl " being used herein to include the residue of a carboxylic acid, carboalkloxy, and carboaralkoxy, and the term " lower alkyl " denoting alkyl groups containing from one to five carbon atoms These compounds are readily converted to valuable \<-desoxy-morphine derivatives by processes described in the Specification of copending Application 13937/54 (Serial No 786,156). The formula of morphine is shown for comparison: This invention also provides a process for producing the said compounds from a 6(lower alkyl or aryl)-dihydromorphine by esterifying its phenolic hydroxy group 6(lower alkyl or aryl)-dihydromorphines can themselves be produced by the reaction of dihydromorplilnone with an ethereal solution of an alkyl lithium or an aryl lithium such as methyl lithium, ethyl lithium, propyl lithium, butyl lithium and phenyl lithium, thereby forming the corresponding 6-alkyldihydromnorphine or 6-aryl-dihydromorphine, such as 6-methyl dihydromorphine, 6-ethyldihydromorphine, 6-propyl-dihydromorphine, 6-butyl-dihydromorphine and 6-phenyl-dihydromorphine. Esterification of the 3-hydroxy group of the 6-(lower alkyl)-dihydromorphine or 6aryl-dihydromorphine is accomplished by reacting the 6-(lower allkyl)-dihydromorphine or 6-aryl-dihydromorphine with an organic esterifying agent such as an organic acid halide or an organic acid anhydride. Examples of the esterifying agents which can be used satisfactorily in the process of this invention are aliphatic and aromatic acid anhydrides and halides as well as carboalkoxy and carboaralkoxy halides. Some of the specific compounds which have served as esterifying agents are acetyl chloride, carboethoxy chloride, carbobenzoxy chloride, and acetic anhydride Excess amounts of the esterifying agent may be used in the process without adversely affecting the yield of the esterified

product In fact, if the esterifying agent is a liquid it may be used in excess to replace the solvent which would ordinarily be employed during the reaction The preferred esterifying agents are acetic anhydride or carboalkoxy chlorides. Although pyridine is the solvent of choice for the esterification, other solvents such as water or organic solvents having no reactive hydrogen atoms can be employed efficiently in this process Examples of the solvents that can be used are aliphatic, alicyclic, and aromatic hydrocarbons, halogenated hydro(pfls, 786,157 1954. i _e 2 786,157 carbons, ethers, ketones and tertiary amines, (such as toluene, chloroqorm, dioxane, and N-ethyl piperidine. It is generally preferred to conduct the reaction of the 6-alkyl-dihydromorphine or 6aryl-dihydromorphine with an esterifying agent in the presence of an acid binding agent, thus neutralizing the acid formed during the reaction and increasing the yield of the ester The basic material used may be an alkali or alkaline earth metal oxide, hydroxide, carbonate or bicarbonate or an organic tertiary amine The preferred acid binding agent is pyridine. It is convenient to carry out the esterification at approximately room temperature or slightly above room temperature for a period of about six to twenty-four hours although higher temperatures may be employed with resultant shortening of the time cycle. The reaction product, an O',-acyl-6-(lower alkyl)-dihydromorphine or an O-acyl-6-aryldihydromorphine, may be purified by extraction into a solvent immiscible with the reaction mixture, and subsequently crystallized by trituration with ether. The following-examples are given to illustrate methods of carrying out the process of the invention. EXAMPLE 1. Preparation of O '-Carbomethoxy-6-MethylDihydromorphine. 11 g of 6-methyl-dihydromorphine (which can be prepared as set forth hereinbelow) was dissolved in 80 ml of dry pyridine To this mixture was added dropwise 7 ml of methyl chlorocarbonate while cooling and stirring. After standing overnight at room temperature the solution was poured onto crushed ice and a small quantity of sodium bicarbonate solution was added The mixture was extracted with chloroform, the extract washed with water, dried over anhydrous sodium sulphate and concentrated in vacuo to a viscous syrup Trituration of the syrup with a small volume of ether induced instant crystallisation of 7 5 ' grains of O'-carbomethoxy-6-methyl-dihydromorphine having a melting point of 139 -141 C, i>D 2 = -241 ' C ( 1 % absolute alcohol). Analysis calculated for: C 2,HQON ( 359 4); C, 66 83; H, 7 01; N, 3 90 Found:

C, 67 42; H, 7 13; N, 3 96. The 6-methyl dihydromorphine starting material in this example was prepared as follows: 13 5 g ( 0 047 moles) of solid dihydromorphinone were added with stirring, over a twenty-minute period, to 107 ml of a 1 3 molar solution of methyl lithium in absolute ether ( 0 14 moles of Chl Li) Thle resulting mixture was stirred for an additional period of forty-five minutes maintaining the temperature of the mixture at approximately 20 ' C The reaction mixture was then added to a cold dilute aqueous solution of acetic acid, and sufficient ammonium hydroxide was added to the resulting mixture to adjust the p H to approximately 9 The aqueous alkaline solution was then extracted with chloroform, and the chloroform extract was evaporated to 70 dryness in vacuo The residual material was recrystallized from 200 ml of acetone to give 6-methyl dihydromorphine; melting point 210-211 ' C. EXAMPLE 2 75 Preparation of O'-Carboethoxy-6-MethylDihydromorphine. 1.18 g ( 0 0039 moles) of 6-methyl-dihydromorphine was dissolved in 25 ml of dry pyridine To this mixture was added drop 80 wise 0 5 g of ethyl chlorocarbonate (with cooling) A transient precipitate and slight yellow coloration were noted in the reaction mixture After standing overnight at room temperature the holution was poured onto 85 crushed ice and a small quantity of sodium bicarbonate solution was added The mixture was extracted with chloroform, the extract washed with water, dried over anhydrous sodium-sulphate and concentrated in vacuo 90 to a viscous syrup Trituration of the syrup with a small volume of ether induced instant crystallization of O-carboethoxy-6-methyldihydromorphine, having a melting point of 119 '-121 V C A yield of 1 3 g was 95 obtained Recrystallization of 03 carboethoxy-6-methyl-dihydromorphine from ether resulted in a product having a melting point of 120 '-121 ' C, 71,25 = -216 ' C ( 1 % absolute alcohol) 100 Analysis Calculated For: C>,,IH 7 ON ( 373 4); C, 67 54; H, 7 28; N, 3 75; Found: C, 68 08; H, 7 26; N, 4 20. EXAMPLE 3. Preparation of 0-Carboethoxy-6-Ethyl 105 Dihydromorphine. 1.7 g of 6-ethyl-dihydromorphine (which can be prepared as set forth hereinbelow) was dissolved in 10 ml of dry pyridine To this mixture was added dropwise 1 ml of 11 C ethyl chlorocarbonate (with cooling) After standing overnight at room temperature, the solution was poured onto crushed ice and a small quantity of sodium bicarbonate was added The mixture was extracted with 115 chloroform, the extract washed with water, dried over anhydrous sodium sulphate and concentrated in vaouo to a viscous syrup The 0 '-carboethoxy-6-ethyl-dihydromorpliine was obtained as a colourless oil which was highly 12 C soluble in organic

solvents. The 6-ethyl dihydromorphine starting material in this example was prepared as follows: 10 g ( 0 035 moles) of dihydronmorphinone was added over a twenty-minute 125 period of 250 ml of an ethereal solution containing 0 11 moles of ethyl lithium The mixture was stirred at room temperature for a period of about 45 minutes The reaction mixture was poured into cold dilute aqueous 13 C 786,157 EXAMPLE 5. Preparation of O '-Carbobenzoxy-6-MethylDihydromorphine. To 1 9 g of 6-methyl-dihydromorphine in 65 ml of dry pyridine was added 1 2 g of carbobenzoxy chloride in toluene solution. After standing overnight at room temperature the solution was poured onto crushed ice and a small quantity of sodium bicarbonate solu 70 tion was added The mixture was extracted with chloroform>, the extract washed with water, dried over anhydrous sodium sulphate and concentrated in vacuo to a viscous syrup. EXAMPLE 6 75 Preparation of O'-Acetyl-6-MethylDihydromorphine. A mixture of 5 g of 6-methyl-dihydromorphine, 50 ml of dry pyridine and 3 rml of acetic anhydride was prepared and allowed 80 to stand overnight at room temperature The product, O '-acetyl-6-methyl-dihydroinorphine, was extracted into chloroform in the usual manner The chloroform extract was dried and concentrated and the residual oil crystal 85 lized from ether to yield a pure product, 0 'acetyl 6 methyldihydromorphine, having a melting point of 1730 C, 'D 2 '= 2310 C. ( 1 % absolute alcohol). Analysis Calculated For: C 2 OH,,04 N 90 ( 343 4): C, 69 93; H, 7 34; N, 4 08 F Pound: C, 70 18; H, 7 65; N, 4 01. EXAMPLE 7. Preparation of 0 '-Carboethoxy-6-ButylDihydromorphine 95 4.5 g of 6-butyl-dihydromorphine (which can be prepared as set forth hereinbelow) was dissolved in pyridine To this mixture was added dropwise an excess of ethyl chlorocarbanate (with cooling) After standing 100 overnight at room temperature, the solution was poured onto crushed ice and a small quantity of sodium bicarbonate solution was added The mixture was extracted with chloroform, the extract washed with water, 105 dried over anhydrous sodium sulphate and concentrated in vacuo to a viscous syrup Trituration of the syrup with a small volume of ether induced crystallization of O '-carboethoxy-6-butyl-dihydromorphine 110 The 6-butyl dihydromorphine starting material in this example was prepared as foflows: 0.2 mole of n-butyl-lithium was reacted with 17 1 grams ( 0 06 mole)

of the dihydro 115 morphinone at 00 C The oily residue of 6butyl dihydromorphine slowly crystallized and, after washing with acetone, melted at 1750 C The yield was 4 5 grams Recrystallization did not raise the melting point The 120 analytical sample was sublimed in vacva lC'1 = 1500 C ( 1 % absolute alcohol).

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* GB786158 (A)

Description: GB786158 (A) ? 1957-11-13

Improvements in pigment compositions

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PATENT SPEGICATION Date of filing Complete Specification: Aug 10, 1955. Application Date: Sept 24, 1954 No 27635/54. Complete Specification Published: Nov 13, 1957. 786,158 Index at Acceptance -Classes 2 ( 2), F( 2 B: 2 F: 811); 2 ( 6), P 7 (C 8 B: 020 A: D 1 A: D 2 A 1: 52); and 95, A 5. International Classification -CO 8 b, f CO 9 d. COMPLETE SPECIFICATION. Improvements in Pigment Compositions.

We, RAYMOND DEVERELL-SMITH, ERIC I'ANSON, JACK MELLOR and HARRY JAMES TWITCHETT, of Hexagon House, Blackley, Manchester, all British Subjects, and IMPERIAL CHEMICAL INDUSTRIES LIMITED, of Imperial Chemical House, Millbank, London, S W A, a British -Company, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement:- This invention relates to new compositions of matter and in particular it relates to new pigment compositions for use in the coloration of Dlastic media. It has hitherto been proposed to use lead chromate pigments, which possess bright shades and good fastness properties to light and heat, in the coloration of plastic media and particularly in the coloration of polystyrene and polythene plastic mouldings. The lead chromate pigments however suffer from the disadvantage that they are unstable in many plastic media at the high temperatures, for example 260-280 C, that are now used in the trade for moulding. We have now found that this disadvantage can be obviated in the case of polystyrene plastic media by adding a di or tri-carboxylic aromatic acid to the lead chromate pigment. According to our invention therefore we provide in the first place new pigment compositions suitable for the coloration of polystyrene plastic media which comprise lead chromate pigments wherein for every parts by weight of a lead chromate pigment there is present between 5 parts and parts by weight of a di or tri-carboxylic aromatic acid. lPrice ri WI l 4 S 6 d The said lead chromate pigment may be for example a middle, lemon, primrose or scarlet (molybdate) chrome pigment. As suitable di or tri-carboxylic acids there may be mentioned for example terephthalic acid, 2-chloroisophthalic acid, diphenylether-4: 41-dicarboxylic acid, naphthalene- 11:4: 8-tricarboxylic acid, monochloroterephtbalic acid, 4: 5-diphenphthalic acid and 4-chlorophthalic acid. The said new pigment compositions may also contain other suitable pigments, provided that these pigments are stable in polystyrene plastic media, in order to obtain compound shades Moreover, opaque white pigments for example titanium dioxide, or extenders for example blanc fixe may be added. The new pigment compositions may also contain other constituents for example basic aluminium sulphate as described in our copending U K Application No 27636/54 (Serial No 786,159) and such compositions may be used also for the coloration of cellulose acetate plastic media as therein described. We have also found that pigment compositions which comprise both the

di or tricarboxylic aromatic acid and the basic aluminium sulphate may also be used for the coloration of polythene plastic media and particularly in the coloration of polythene plastic mouldings and extrusions. These media are not satisfactorily coloured by pigment compositions which comprise only the di or tri-carboxylic acid and not the basic aluminium sulphate, or vice versa. Thus according to a further feature of our invention we Provide in the second place new pigment compositions suitable for the coloration of plastic media, particularly polystyrene, polythene and cellulose acetate 2 _; 3 r,plastic media, which comprise lead chromate pigments wherein for every 100 parts by weight of a lead chromate pigment there is present between 5 and 75 parts by weight of a di or tri-carboxylic aromatic acid and also basic aluminium sulphate in amount preferably between 50 and 500 parts by weight. The expression "basic aluminium sulphate" relates to that product which may be obtained by the interaction of aqueous solutions of sodium carbonate and aluminium sulphate and in the trade this product is also known and used under such expressions as "alumina white," "alumina hydrate," "alumina hydroxide," or "hydrated aluminium hydroxide " According to yet another feature of our invention we provide a process for the 2 D manufacture of coloured plastic media especially polythene, polystyrene and cellulose acetate plastic media which comprises incorporating the aforesaid new pigment compositions of the invention into plastic media. The said incorporation may be brought about for example by masticating mixtures of the new pigment compositions and the said plastic media on a hot roll mill and then cooling and granulating to produce homogeneously coloured moulding powders or extrusion compounds. The new pigment compositions are useful for the production of full, reduced or pastel shades in plastic media and especially at the high temperatures now used in the trade for moulding and extrusion Mouldings and extrusions so obtained at these high temperatures are brighter than those obtained at the same temperatures using pigment compositions which do not contain the described additions. The invention is illustrated but not limited by the following Examples in which the parts are by weight:EXAMPLE 1. A polystyrene moulding powder is obtained by mixing the following:parts of polystyrene; 05 part of the scarlet chrome pigment obtained by the addition of an aqueous solution containing sodium chromate, sodium sulphate and sodium molybdate to an aqueous solution of lead nitrate; 0 1 part of terephthalic acid, and masticating the said mixture on a hot roll mill or in an extrusion machine The mixture is then cooled and granulated and there is obtained a polystyrene

moulding powder A moulding may be manufactured from the said moulding powder by the use of a prolonged moulding cycle at a high temperature for exam Dle 15 minutes at 280 ' C When so obtained, the moulding is scarlet in colour whereas omission of the terephthalic acid from the said moulding powder gives a moulding in which the colour is destroyed. EXAMPLE 2. A polystyrene moulding powder obtained by mixing the following:is 70 parts of polystyrene, 0.5 part of the scarlet chrome pigment (obtained as described in Exam Dle 1); 0.1 part of tereplithalic acid; 0.5 part of titanium dioxide, and masticating the said mixture on a hot roll mill or in an extrusion machine The mixture is then cooled and granulated and there is obtained a polystyrene moulding powder A moulding may be manufactured from the said moulding powder by the use of a prolonged moulding cycle at a high temperature, for example, 15 minutes at 280 ' C When so obtained, the moulding retains much more nearly the original scarlet shade of the moulding powder than when the terephthalic acid is omitted from the moulding powder. EXAMPLE 3. A polystyrene moulding powder obtained by mixing the following is parts of polystyrene; 0.5 part of a lemon chrome pigment obtained by precipitating together a mixture of lead chromate and lead sulphate; 0.1 part chloroterephthalic acid; s O and masticating the said mixture on a hot roll mill or in an extrusion machine The 100 mixture is then cooled and granulated and there is obtained a polystyrene moulding powder A moulding may be manufactured from the said moulding powder by the use of prolonged moulding cycle at a high tem 105 perature for example 15 minutes at 280 ' C. When so obtained the moulding is yellow in colour wherein when the choloterephthalic acid is omitted from the moulding powder there is obtained a moulding in which the 110 colour is largely destroyed. EXAMPLE 4. A polystyrene moulding powder is obtained as described in Example 3 but adding 0 5 part of titanium dioxide to the 115 mixture of polystyrene, lemon chrome pigment and chloroterephthalic acid prior to mastication The moulding obtained at 280 ' C is pastel yellow in shade whereas when the chloroterephthalic acid is omitted 120 786,158 parts of polythene, 0.5 part of the scarlet chromie pigment (obtained as described in Example 7); 0.1 part of chloroterephthalic acid; 0.5 part of titanium dioxide; 0.4 part of basic aluminium sulphate; and masticating the said mixture on a hot roll mill The mixture is then cooled and granulated and there is obtained a moulding compound A moulding may be manufactured from the said moulding powder by the use of a prolonged moulding cycle at a high temperature, for example, 15

minutes at 2400 C When so obtained, the moulding retains much more nearly the original bright orange shade of the moulding compound than when the terephthalic acid is omitted from the moulding powder. from the moulding powder there results a moulding the colour of which is largely destroyed. EXAMPLE 5. A polystyrene moulding powder is obtained as described in Example 3 using as mixture: parts of polystyrene; 0.5 part of primrose chrome pigment obtained by precipitating a mixture of lead sulphate and lead chromate under acid conditions; 0.1 part of terephthalic acid. The moulding obtained at 2800 C is greenish-yellow in shade whereas when the terephthalic acid is omitted from the moulding powder there results a moulding the colour of which is largely destroyed. EXAMPLE 6. A polystyrene moulding powder is obtained as described in Example 5 but adding 0 5 part of titanium dioxide to the mixture of polystyrene, Drimrose chrome pigment and terephthalic acid prior to mastication. The moulding obtained at 280 ' C is a pastel shade of greenish-yellow whereas when the terephthalic acid is omitted from the moulding powder a moulding is obtained the colour of which is largely destroyed. EXAMPLE 7. A polythene moulding powder is obtained by mixing the following: parts of polythene; 0 5 part of the scarlet chrome pigment obtained by the addition of an aqueous solution containing sodium chromate, sodium sulphate and sodium molybdate to an aqueous solution of lead nitrate; 0 1 part chloroterephthalic acid; 0.5 part basic aluminium sulphate; and masticating, the said mixture on a hot roll mill or in an extrusion machine The mixture, is then cooled and granulated and. there is obtained a polythene moulding powder A moulding may be manufactured from the said moulding powder by the use of a prolonged moulding cycle at a high temperature for example 15 minutes at 2400 C When so obtained, the moulding is scarlet in colour whereas omission of the terephthalic acid from the said moulding powder gives a moulding in which the colour is much duller. EXAMPLE 8. A polythene moulding powder is obtained by mixing the following:EXAMPLE 9. A polytliene moulding powder is obtained as described in Example 8 but using;parts polythene; 0.5 part of a lemon chrome pigment obtained by precipitating together a mixture of lead chromate and lead sulphate; 0.4 part basic aluminium sulphate; 0.1 part chloroterephthalic acid; The moulding obtained is yellow in colour whereas when the basic aluminium sulphate and chloroterephthalic acid are omitted the colour is largely destroyed.

EXAMPLE 1:0. A polythene moulding powder is obtained. as described in Example 9, but adding 05. part of titanium dioxide to the mixture of Vpolythene; lemon chrome, basic aluminium 95 sulphate and chloroterephthalic acid prior to mastication. The moulding obtained is pastel yellow inshade whereas when the chloroterephthalic acid and basic aluminium sulphate: are 100 omitted the colour is largely destroyed. EXAMPLE 11-. A polythene moulding powder is obtained as described in Example 9 by using: parts polythene; 0.5 part primrose chrome pigment, obtained by precipitating a mixture of lead sulphate and lead chromate under acid conditions; 0.1 part chloroterephthalic acid; 0.4 part basic aluminium sulphate. The moulding obtained is greenish-yellow whereas when the chloroterephthalic acid and basic aluminium sulphate are omitted 786,158 -1 a moulding is obtained in which the colour is largely destroyed.

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