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In the Matter of Tiemann's Patent.

first step towards the finished product; but there is no difficulty in any chemist following out the process by the directions, and the processes were old and well known. As to the second paragraph of the Specification, it is objected that the description of the way of getting rid of the unattacked citral and the unchanged 5 acetone and volatile products of condensation is not sufficient; but I am instructed that there is no difficulty in carrying off these products by steamthe boiling point of acetone is very low, about 60°, that of citral about 110° to to 112°. One merely takes off the more volatile elements by means of steam. Pseudo-ionone was first ascertained in this Patent, and in answer to the 10 objection of insufficiency of description of the process-first, it is ample for anyone who understands organic chemistry; and, secondly, up to that point the invention was not of any process. Coming to paragraph 4, ionone is of great value as producing the violet perfume, and it is in substance the invention. The process of conversion is sufficient, and it is a new process. One is to distil 15 as often as one wishes to between 125° and 135° under the pressure mentioned until one gets the product one desires. At the word "collected" the product is a commercial one, and valuable for perfumery purposes; but Dr. Tiemann, in order to disclose all he knew, adds the next words as to further purification, and there is no difficulty in carrying this out. The next passage says that you 20 can treat the pseudo-ionone with the acid treatment in the same way as you can treat the ionone. The two products resemble one another closely; the formula is the same, and the indices of refraction and specific weights only differ slightly. Nothing arises here on the paragraph of the Specification preceding the claims. Claim 1 is a product claim for ionone; as to Claim 2, you get 25 ionone substantially as described when you get to the word "collected" in the Specification; and, if further purification is wanted, the Patentee tells the way of doing that. As to Claim 3, the new point was in utilising the process to obtain the product. In Claim 4, the words "or" to "derivatives" must be read together. Coming to the Particulars of Objections, the point as to utility 30 in No. 1 is in substance the same as No. 2, under which the real contest will be. As to 2 (1) the process is very simple, and is very simply described. The shaking has to go on for a long time-the Specification says for several days. The instance given in the Specification works very well. As to sub-clause 2, the ordinary normal temperature will do, and with regard to the strength of 35 solution of the alkaline agent that does not matter; in the instance given it does not matter what proportion is taken; any person skilled in organic chemistry could carry through the operation, the process being perfectly well known. As to sub-clause 3, the objection is merely that there is one alkaline agent-ammonia-which, as was well known, would not be used to condense 40 a ketone. The Specification directs the use of one of the hydrates of alkaline earths, or hydrates of alkali metals, or other alkaline agents as a condensation agent, and all of them which would be known to chemists as condensation agents can be used, and all produce the result by the process described. As to sub-clause 4, there is no question of pressure; one simply applies a current 45 of steam to carry off the more volatile bodies. Sub-clause 5 is the same in other words. Purification by fractional distillation is perfectly well known, and it is perfectly easily worked. Sub-clause 6 relates to the purification of ionone, and the process works and is sufficiently described, the method is possible and everything is told; when one has applied the dilute acids, one has to skim off 50 the surface the product obtained. Furthermore the process is an old one. All the purification which is necessary is got at the stage where the word "collected is reached. The next lines only give an alternative method of further purification, which was well known although not applied to this subject matter, and which will work. It will be said on the other side that if you want to get 55 that purity of product which is denoted by a product that boils at 128°, you do not get it at the word "collected." The claim is not limited to tie the inventor down to that pure ionone, corresponding to a particular formula and boiling at

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In the Matter of Tiemann's Patent.

a certain temperature. He is claiming ionone sufficiently pure for commercial purposes. He says "about 128°," and we can get such a product at the word "collected," one has to go on with fractional distillation until one gets the particular purity one desires. But the Patentee is not limited to a particular purity of ionone which boils at 128°. As to sub-clause 7 and No. 3 of the 5 Particulars of Objections, they are quite unfounded.

Professor J. Dewar* and Dr. Adolph Liebmann were called as witnesses on behalf of the Respondents.

Moulton, Q.C., during his cross-examination of Professor Dewar, proposed to put certain questions relating to the passage in the Specification:-"The 10 "ketone derivatives of the pseudo-ionone are converted under similar conditions "into ketone-derivatives of the ionone." Cripps, Q.C., objected that the Particulars of Objections did not raise the point. Moulton, Q.C., relied on Particular 2 (6). There are two methods claimed in the fourth claim for making ionone; the first is by treating the pseudo-ionone finally with acids and the 15 other, "or its ketone condensation products with phenylhydrazine or other "ammonia derivatives." The way of obtaining the ketone derivatives of ionone given in the passage in question is part of the process of carrying out Claim 4. [COZENS-HARDY, J.-Particular 2 (6) only deals with the question of purification.] It is really the question of manufacture of ionone, although 20 we say purification. The ionone referred to in the second claim is pure ionone. [Cripps, Q.C.-What is said in Particular 2 (6) is that the further purification of ionone by the use of phenylhydrazine cannot successfully be carried out.] After the conversion which is mentioned, the rest is separation. The ionone claimed in Claim 2 is not simply the mixture but the pure body 25 made in the conversion and having the characteristics set forth as to boiling point, specific weight, and index of refraction. The whole mixture is not transformed into an isomeric ketone, but in the resulting mixture there is an isomeric ketone which he calls ionone. If the ionone claimed is the pure body, then under the Objection the point is—are there sufficient directions for making 30 what is claimed in Claim 2? The question of purification is really a question of extraction. [Cripps, Q.C.-The question asked was as to the conversion of the ketone derivatives of the pseudo-ionone into ketone derivatives of the ionone. That has nothing to do with the point as to purification.] Part of Claim 4 relates to getting ionone through the ketone derivative of pseudo- 35 ionone. The passage in question tells one how to do that, because it says one may get from those to the ketone derivatives of the ionone; and the previous lines give one a way of purifying which consists in passing through a ketone derivative of ionone. According to the first part of the fourth claim one starts from pseudo-ionone; one gets ionone in the 40 mixture, then one gets the ketone derivative, and then ionone. But, according to the alternative way, one makes the ketone derivative of the pseudo-ionone, and turns it into the ketone derivative of the ionone, and then, as before, one obtains the pure ionone. [CoZENS-HARDY, J.-You are asking me to say that in Particular of Objection 2 (6), the "purification" means 45 "production."]

Astbury, Q.C.-Under the Patent one has to get one definite ketone, not a mixture of isomers. By the treatment in the acid bath the whole of the pseudo-ionone is not made into ionone. The next step is the fractional distillation. By "purification" the Patentee means "isolation." 50 When he says that the product may be still further purified, &c., he means that it may be done by that method or other methods. Assuming that the Specification is right, one manufactures ionone when one gets off

* Professor Dewar said that the formula for citral was C10H160 and for acetone C,H2O; that these bodies combined by the loss of molecules of water, so that substracting H2O from the sum that left C13H200.

In the Matter of Tiemann's Patent.

the mixture boiling between 125° and 135°, but it is with other things; the point of the purification is to separate it from those. Particular of Objection 2 (6) says that no sufficient directions are given for the purification of ionone, and one must not exclude from that a step which is for the purpose of 5 what the Patentee calls purification.

Cripps, Q.C.-The point is not raised by the Particulars. The point that is raised is that of purification or separation, and that is raised with respect to the lines preceding the passage in question. One produces ionone when one gets the mixture mentioned, there is no further conversion, but one 10 separates out the ionone.

COZENS-HARDY, J.-I think that this point is not covered by the Particulars of Objections. It seems to me that the word "purification" here is deliberately used to distinguish it from the mode of production. The production of the ionone is referred to very distinctly in Claim 4, and it is marvellous that 15 that is not found here, but it is not to be found here. Purification deals with the result of the whole process after the ionone has been produced, and is found mixed with other things. The only matter which is referred to by the sixth Objection, as I read it, is the mode of purifying the product, which is described in the last two lines at the bottom of page 2 of the Specification. 20 Therefore, I do not think that I can allow the cross-examination on the two lines on the top of page 3.†

Moulton, Q.C., asked for leave to amend. COZENS-HARDY, J., assented on the terms of the case standing over and the Petitioners paying the costs. Moulton, Q.C., said that, if it was a matter of the case standing 25 over, he should not ask to amend. Subsequently, Cripps, Q.C., objecting to other questions put in cross-examination as not being within the limits of the Particulars of Objections. Moulton, Q.C.-This is on Clause 1, that the invention described is not useful; that means that it will not work. COZENS-HARDY, J.-I cannot allow you to go into that under a general 30 Objection. In Particular 2 the Petitioners have given seven particulars as to insufficient description. Moulton, Q.C.-The Objection that it will not work is a different one, and it is covered by the Objection of non-utility (Kurtz v. Spence). Cripps, Q.C.-This point is not in the report. [The question was dropped for the time being.]

35

*

Moulton, Q.C.-This was a Patent for a new substance, produced from citral, a well-known organic body, and acetone by a condensation process. The reactions are very complicated. It is a process which involves the breaking up of two complex molecules; and in the breaking up different bodies are formed. A di-acetone may be formed or a di-citral, or other more complicated 40 bodies, which, although distinct, may have the same components. In such a case it is necessary that complete and accurate directions should be given. The witnesses for the Petitioners will say that they have followed the directions given, but the result has been failure. Turning to the Particulars of Objections, the objection that the invention is not useful does not mean that ionone, if 45 obtained, is not useful. The meaning is that the Patentee has not given a process that will work and make the ionone; that is covered by the objection (Frost on Patents, p. 145, quoting the judgment of Lindley, L.J., in Lane-Fox v. The Kensington and Knightsbridge Electric Lighting Company, Ld., 9 R.P.C. at p. 417). It may also mean that there is no utility in what the 50 Patentee does. [COZENS-HARDY, J.-I understand that Particular 1 means that, because in 2 you specify certain respects in which you allege that the Patent will not work.] It may be that there is repetition. [COZENS-HARDY, J.In that case the Particulars are misleading.] Non-utility means that the thing is impracticable (Tolson v. Speight & Sons, 13 R.P.C. 718). [Cripps, Q.C.

* The trial of the action is reported 4 R.P.C. 161.
Ante, page 563, 11. 19 and 20.

In the Matter of Tiemann's Patent.

The issue of utility would be whether it produces a smelling substance for perfumery purposes.] The invention must, when put in practice by a competent man, do what it professes to do. As to Particular 2 (1), I shall show that the pseudo-ionine may not be formed at all; the directions are not sufficient to insure it being made. Other ways of making it are now 5 known. In Claim 1, as well as in the body of the Specification, alkaline agents generally are mentioned. The directions are insufficient in this respect. Alkaline agents will not produce pseudo-ionone if used as directed, at all events not with certainty. Coming to Particular 2 (2), the body is not one that is formed without any bye-products, there are other products of condensation. 10 Then there is also Particular 2 (3). [COZENS-HARDY, J.-That distinctly raises the question of the quantity yielded.] As to Particular 2 (4), the evidence will be that distilling by steam does not assist. Particular 2 (5) refers to the steam treatment and to the distillation. As to 2 (6), there is no difference really between the terms purification and separation, because ionone is a definite 15 body. As to 2 (7), the evidence will show that the Patentee must have had further information than he gave. His duty was to give full and complete directions. Our witnesses will say that the condensation process described may produce a variety of results, and any one following it out will get little, if any, pseudo-ionone. With many of the alkaline agents none would be obtained. 20 One would get condensation products, but they would be other bodies. The Specification gives no indication of the proper strength of the condensation agent. One might happen to use an alkaline agent which forms the pseudo-ionone and then destroys it. The Patentee must have known what would succeed. The production of the pseudo-ionone is only during the condensation process, what is 25 done afterwards is done to separate it. The limit of 138° to 155° is taken widely to make sure that one has got the bodies between 143° and 145°. One fractionisation only is intended. It was well known that separation by steam may separate bodies that will not separate by fractional distillation. The fair way of carrying it out would be to keep the steam on until it has carried off what it will carry off 30 readily. It is desired to get rid of any citral, and the two indications that that is done would be, first, that little is going over, and secondly, that there is no smell of citral. Volatinisation by steam is not a practical way of getting the pseudo-ionone; it would itself come over. Anyone following the Specification would follow it very closely because he would not know what the dangers were. 35 To retain everything between 140° and 150° instead of between 143° and 145° is contrary to the directions given. It is found that the bulk comes over about 148° and 149°, and not much between 143° and 145°, therefore, if what comes over between 140° and 150° is taken, one gets more of what is not pseudoionone than one does of pseudo-ionone. The latter is a perfectly definite body, 40 and all that is obtained between 128° and 135° is not pseudo-ionone, which was what Professor Dewar suggested. The effect of the acid is to arrange the parts of the molecule, so as to turn pseudo-ionone into ionone, which has the same composition. But there are also other isomers absolutely different from these. I do not deny that by the method given in lines 43-46 if one has the real 45 pseudo-ionone, one gets a conversion, but one gets other bodies besides ionone. The method of purifying given in 11. 50 to 52 fails. Phenylhydrazine is an important purifying or separating agent, when it forms crystals. But with this body it does not form these, and it takes up all the ketones, all the impurities, and leaves the thing no better than before. Dr. Liebmann had to use fractional 50 distillation afterwards. This is a Patent for producing certain definite bodies, namely pseudo-ionone and ionone separately. The Patentee gives particulars to identify ionone, and the question is whether one is told how to get it. Claim 1 is for a new definite product, and the Patentee was bound to define it

* Ante, p. 563, 1. 15 to 1. 18.

In the Matter of Tiemann's Patent.

otherwise than by the process. So in Claim 2 also ionone is claimed by the characteristics. Claim 3 is for the process for producing pseudo-ionone. Claim 4 claims two methods of producing ionone, one is to get it from pseudoionone directly, and the other to get it through the phenylhydrazine compounds. 5 But neither method will enable one to get it separately than other bodies.

The following witnesses gave evidence on behalf of the Petitioners, namely, Dr. Passmore, Dr. Ziegler, Dr. Ostermann, Professor Semmler, and Mr. Ballantyne.

At the conclusion of the Petitioners' evidence, Dr. Tiemann was called and 10 Dr. Liebmann was recalled, and Dr. Passmore was recalled on behalf of the Petitioners.

Moulton, Q.C., summed up the Petitioners' case. I will first deal with the law on this subject. The attack on the validity of the Patent is on the ground that the Specification does not contain sufficient directions to enable the public 15 to carry out the invention. It used to be a condition of the grant of a Patent that sufficient directions should be given, and the grant took place subject to conditions to be afterwards fulfilled; now the condition is the same, but it must be fulfilled in the Specification. The Courts have laid down that it is part of the consideration for which a Patent is granted that the public should 20 be put in possession of the invention; otherwise there would be unfairness to the public. The public must be able to carry out the invention by reason of the disclosure in the Specification (R. v. Arkwright, 1 Web. P.C. 64; Turner v. Winter, 1 Web. P.C. 77). It is not necessary that the failure to make discovery should be intentional. It is not sufficient to give a method which sometimes 25 succeeds and sometimes does not (Simpson v. Holliday, L.R. 1 H.L. 315; also Gandy v. Reddaway, 2 R.P.C. 49). It is the same thing for this purpose whether a direction is given which is actually wrong or a necessary direction is omitted. If a Patentee has described an invention in a way covering many alternatives and some of them will not work, that is fatal (Kurtz v. Spence, 30 5 R.P.C. at page 184). A Patent is not good unless the directions given, if fairly followed, produce the specified result (Muntz v. Foster, 2 Web. P.C. at page 109). If experiment be necessary for carrying out the invention, the Patent is bad. In this case the Patentee had at the date of the Patent been making on a manufacturing scale, and therefore he could have told the world exactly how to do 35 it. The test is whether a person to whom the Specification is addressed-that is, a competent person-can carry it out by the directions and without further experiment. The Patentee has not given the proportions of the alkaline agent nor the strength of the solution. In the case of hydrate of barium no directions are given as to proportions. If the test is whether there would be a doubt as 40 to what is meant, then there is no question that there is insufficiency. The Patentee made his process to include the use of all alkaline agents, and ought to have taught the public how to use them all. The Patentee was in possession of the details necessary for carrying out the invention on a manufacturing scale. If a Patentee is in possession of valuable information defining the 45 successful way of carrying out the process and does not put it in his Specification, he omits it at his own risk. If a competent chemist will not succeed without it, it is not open to the Patentee to say that he might have done so. As to the first part of the Specification, it is to get the definite body pseudo-ionone, which was then unknown, and it is not like having to get a known body having 50 known properties. The evidence shows that there are not sufficient directions as to the strength of the alkali, and it is to be noticed that one is told that pseudo-ionone is readily decomposable by alkalies. Repeated experiments are necessary, and even then those made by our witnesses were unsuccessful. Dr. Ziegler made more than 50 unsuccessful experiments. In his evidence he gave 55 in detail three later experiments. [The results of experiments were then referred to.] The evidence shows that there is at least one other condensation product, and that this product boils about 150° and is far more stable than

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