4921 4925.output

* GB785328 (A)

Description: GB785328 (A) ? 1957-10-23

Improvements in or relating to tumbling material and method of finishing,deburring and polishing metal pieces

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The EPO does not accept any responsibility for the accuracy of data and information originating from other authorities than the EPO; in particular, the EPO does not guarantee that they are complete, up-to-date or fit for specific purposes.

PATENT SPECIFICATION 7859328 Date of Application and filing Complete Specification April 7, 1955. g 1 g F lr I No 10339155. Application made in Germany on April 12, 1954. Complete Specification Published Oct 23, 1957. Index at acceptance: -Classes 60, E; and 91, D 2 (A: B: C: N). International Classification: -B 24 b C 11 d. COMPLETE SPECIFICATION Improvements in or relating to Tumbling Material and method of Finishing, Deburring and Polishing Metal Pieces We, ROTO-FINISH COMPANY, a corporation In carrying out the invention pumice fragorganized under the laws of the state of Michi ments may be employed However, any similar 50 gan, one of the United States of America, of porous relatively soft rock having a low specific 3700 Milham Road, City of Kalamazoo, State gravity will give improved results A porous of Michigan, United States of America, do material such as pumice is satisfactory because hereby declare the invention for which we pray the grains can become lodged in the pores and that a patent may be granted to us, and the thus retained on the fragments to give effective 55 method by which it is to be performed, to be

polishing action They could also be forced by particularly described in and by the follow the tumbling into the soft light weight ing statement: material. This invention relates to improvements in An artificial or synthetic material may be tumbling barrel finishing and particularly to made from cement which is prepared by mix 60 tumbling barrel smoothing, polishing ing with water and then aerated by blowing and deburring of light weight stampings of air or carbon dioxide into it to give it a porous small cross-section, such as small stamped structure when its sets By blowing the air into parts or thin sheet parts such as are required the cement mixture while it is wet a product for certain electrical appliances or for the smal can be made which has a specific gravity of 65 lest type of ball bearings about one The cement is relatively soft comIt has been found that tumbling barrel tech pared to other chips such as granite which are niques for polishing and deburring metallic sometimes: used pin tumbling material for parts do not give completely satisfactory results polishing and has substantially the structure of when applied to small light parts, if the chips pumice It also polishes off easily ito give 70 or granules of stone employed are of high rounded corners and to provide a powder specific gravity, since they tend to distort the which helps to retain the grains on the surface parts of the fragments. It has also been found that ordinary tumbl In the preferred form of the invention the ing barrel techniques used in smoothing, particles of pumice or the like may be from 75 polishing and deburring metallic parts do not 4 inch to i inch in their largest dimension so give satisfactory results when applied to small that they may be screened through 4 inch to 1 light parts and particularly to small flat parts inch screen However, they may be utilized in If these parts are given wet tumbling treatment sizes of 1/,2 of an inch in their largest dimenthey may stick together or to the walls of the sion It will be understood that in the following 80 tumbling equipment or to the material used for examples when reference is made to the use finishing They also have a tendency to separ of pumice that the artificial or synthetic ate out from the mass of finishing chips or the pumice or porous cement chips or granules like so that the finished product is not uni may be substituted. formly smooth, polished or deburred One example of a method of carrying out 85 According to the present invention there is the invention consists in charging a tumbling provided a tumbling material for polishing, barrel with a charge consisting of 15 parts by comprising dry fragments of light weight weight of pumice granules screened W inch to porous material, said fragments having a l inch with one part by weight of 100 mesh specific gravity of about one and

having their abrasive grains, such as aluminum oxide To 90 largest dimensions from one-quarter to one this mixture, the parts to be polished and thirty-second of an inch, and a film of dry deburred are added The processing is done abrasive grains on the surface of the fragments, dry at about 30 R P M for a total processing which are smaller than said fragments, which cycle of about 24 hours. grains are smaller than said fragments of The finished product of this treatment is 95 porous material uniformly polished, is not distorted and has the proper rounding off and deburring of rough edges and corners. A similar result is obtained by using dry 97 parts by weight of 4 to 8 inch pumice fragments with six parts by weight of 100 mesh abrasive grains The tumbling time can be run as long as 72 hours giving acceptable results in regards to edge, radius and finish without changing shape or form of the processed light, thin, sheet metal stampings. In carrying out the process described above it has been found that the initial tumbling tends to reduce about 6 to 7 % of the pumice to powder during the first 24 hours of operation The particles of pumice become thus rounded and coated with a fine residue of the dust or powdered pumice which picks up and holds the grains of abrasive in such a way as to effectively increase the abrasiveness thereof. The abrasive grains do not appear to be necessarily fixed in great number on the surface of the pumice fragments but the presence of the coat of the powder on the grain appears to give optimum results. It is also possible to pretreat the pumice grains by rolling them with the aluminum oxide grains In this way the pumice particles seem to pick up some of the aluminum oxide grains and when the pumice is quite porous and has large holes or pores in the surface thereof some of the aluminum oxide grains become lodged in these holes It is also possible to pretreat the pumice particles with the grains, using a moistener such as "Tylose" (Registered Trade Mark) solution or other varnish or adhesive The aluminum oxide grains are thus fixed on the surface of the pumice granules by a varnish-like coating. When the above materials and method are employed the small parts do not adhere to the walls of the tumbling barrel or to the material or to one another They remain quite uniformly distributed throughout the tumbling mass and are not distorted or bent and after the tumbling for the periods indicated they are uniformly polished and deburred They do not segregate out of the material and can, however, be easily separated at the termination of the treatment.

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* GB785329 (A)

Description: GB785329 (A) ? 1957-10-23

Process for inhibiting the attack of ozone on natural or synthetic rubber

Description of GB785329 (A)

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PATENT SPECIFICATION 78,5329 Date of Application and filing Complete Specification April 14, 1955. No 10828/55. Application made in United States of America on April 21, 1954. Complete Specification Published Oct 23, 1957. Index at Acceptance: -Classes 2 ( 6), P 2 D 1 A, P 2 K( 7: 8), P 2 T 2 A; and 70, E 14. International Classification: -CO 8 d. COMPLETE SPECIFICATION Process' for Inhibiting the Attack of Ozone on Natural or Synthetic

Rubber We, THE PENNSYLVANIA SALT MANTFACTURING COMPANY, a corporation organised and existing under the laws of the Commonwealth of Pennsylvania, United States of America, of 1000, Widener Building, Philadelphia, Commonweath of Pennsylvania, 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 is concerned with processes for inhibiting the attack of ozone upon vulcanized natural or synthetic rubber and with rubber materials incorporating an inhibitor. Among the constituents of the atmosphere which are capable of reacting with rubber, only oxygen and ozoneproduceany perceptible efect at the concentrations in which they are present, and it appears that two separate and distinct processes are responsible for the breakdown of soft vulcanised rubber when exposed to outdoor weathering, i e, light-energized oxidation and attack by atmospheric ozone. The quantity of ozone in the atmosphere varies with the atmospheric conditions and the locality A probable average ozone concentration in the atmosphere is 2 5 parts by weight per hundred million In some localities, the concentration will be less than this, but in others it may be two or more times as great. In the vicinity of electric motors or other electrical equipment the concentration of ozone in the atmosphere may be increased far beyond that usually found. Ozone has a strong destructive action upon vulcanized rubber, both natural and synthetic, this action being especially pronounced when the rubber is stretched A critical elongation exists, for maximum ozone attack, which varies in accordance with the rubber stock, but it is usually an elongation between 5 and 50 per cent. Ozone in concentrations as low as one part per hundred million will cause checking and crazing of vulcanised rubber in a short time. lPrice 3 s 6 d l Over longer periods of time, and at higher ozone concentrations, cracks develop which grow progressively deeper and longer. One method which has been used for the 50 protection of vulcanized rubber in the past is the application of a film of wax to the rubber after vulcanization, or the incorporation of wax during mixing, so that it blooms to the surface of the rubber article after vulcanization 55 The most prominent disadvantage of wax protection is that under dynamic flexing conditions, such as would be incurred when a tire is mounted on a car or lorry travelling along a highway, the wax film is broken, leaving por 60 tions of the tire unprotected. In accordance with the present invention there is provided a process for rendering a synthetic rubber resistant to ozone attack which

comprises mixing with the rubber prior 65 to vulcanization, an inhibitor having the formula: H S H l 11 1 R-N-C-N-R,, in which, either R and R 1 are identical and are alkyl radicals such as butyl, amyl, or hexyl, having not more than 6 carbon atoms, cyclohexyl or benzyl radicals; or R and R, taken together form a saturated hydrocarbon ring residue containing not more than 2 carbon atoms between the nitrogen atoms, or a phenylene radical. This invention also proivdes a process of rendering natural rubber resistant to ozone attack which comprises mixing a symmetrical dialkylthiourea with the rubber prior to vulcanization The invention also provides ozone-resistant elastomers comprising either a mixture of a synthetic rubber and an inhibitor of the formula above, or a mixture of a natural rubber and a symmetrical dialkyl thiourea. Exemplary of the thiourea which may be compounded with synthetic rubber are ethyene thiourea, o-phenylene thiourea, 4-methylethylene thiourea, symmetrical dibutylthiourea, 1,3-dihexylthiourea, 1,3-di-gec-butylPr IC 91,,7, -, r_ 1,,_ 1 1 1 4 1 4_ 785,329 thiourea, 1,3-di-sec-hexylthiourea, 1,3-dibenzylthiourea, and 1,3-dicyclohexylthiourea. Symmetrical dibutyl thiourea is particularly suitable for compounding with natural rubbers. Included within the term " synthetic rubber" are, for example homopolymers of butadiene or other monomers, copolymers of butadiene with other polymerizable cormpounds, such as styrene, divinyl benzene, acrylic and methacrylic acids and their esters, ethylenic hydrocarbons such as ethylene, butylene, isobutylene and propylene, or with acrylic nitriles or vinyl compounds Included within the term "natural rubber" are the various forms thereof, such as smoked and unsmoked sheet and crepe. In employing the inhibitors of the invention, they may be compounded with either synthetic or natural rubber stocks at any stage prior to vulcanization, in common mixing equipment such as Banbury mixers, mixing rolls, or the like Generally speaking, the inhibitor may be present in the rubber formulation, either synthetic or natural, in an amount from about 0 1 per cent by weight to about 5 0 per cent by weight. The invention will be further illustrated by reference to the following specific example. EXAMPLE The ozone inhibitors of the invention were 30 evaluated by subjecting vulcanized rubber strips, containing the various inhibitors to be tested, to an atmosphere of ozone under controlled conditions. The ozone concentration test employed was 35 essentially the same as that described in A.S T M D 1149-51 T The ozone-absorbing bottle

employed in the test was the same as that described in the aforementioned A.S T M test, and the ozone concentration 40 was determined by electrometric titration with 0.002 N sodium thiosulfate The test procedure employed differed from the aforementioned A S T M test in that a higher concentration of ozone was employed, i e the ozone concentratin was 4 0 O 1 parts per million, which is much higher than the amount pro 45 posed in the aforementioned A S T M test and is also much higher than the concentration of atmospheric ozone, which is about 2 5 parts per hundred million in most parts of the United States 50 The inhibitors evaluated were incorporated into both natural rubber and GR-S stocks, -having compositions as follows:Natural rubber GR-S black 1 Parts Parts Smoked sheet 100 GR-S black 1 150 Stearic acid 3 Acidic type, pine-gum softener 5 Zinc oxide 3 Zinc oxide 5 EPC black 50 Sulfur 2 Acidic type, pine-gum softener 3 Mercaptobenzothiazole 1 6 Sulfur 2 8 Diphenylguanidine 0 1 Mercaptobenzothiazole 1 O 163 7 162 8 The amount of ozone inhibitor added to these formulations in each case was 2 parts per 100 parts of rubber. Rubber specimens measuring 0 5 inch by 0.075 inch by 6 inches were stretched to 12 5 per cent elongation for an ozone exposure period of 4 hours At the end of the 4 hours the number of cracks visible in a 4 square inch area was counted with the aid of a Linen tester The number of cracks per 4 square inch area was taken as the ozone checking index A control stock was run with each series of inhibitor tests. A 30-minute cure at a temperature of 2800 F was employed for the ozone tests on natural rubber inhibitors and a 60 minute cure at a temperature of 307 F was employed for the ozone tests on GR-S inhibitors. The results of the tests are as follows:785,329 TABLE EFFECT OF OZONE ON RUBBER VULCANIZATION Stock Ozone-checking No Name of chemical Index GR-S formulation 1 None (control stock) 4-6 2 Ethylene thiourea 2 3 o-phenylene thiourea 0-0 4 4-methylethylene thiourea 2-1 Symmetrical dibutylthiourea 1-2 6 1,3-dihexylthiourea 0-0 7 1,3-di-sec-butylthiourea 1 8 1,3-di-sec-hexylthiourea 1 9 1,3-dibenzylthiourea 4 1,3-dicyclohexylthiourea O NATURAL RUBBER FORMULATIONS 1 None (control stock) 49 2 Symmetrical dibutylthiourea 0

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* GB785330 (A)

Description: GB785330 (A) ? 1957-10-23

Improved polishing or buffing mop


PATEN 7 %IT SPECIFICATION late tu SIDNEY JAMES HAWL Er" Y. 4,;i/ y l rl;, e ectjficati: A-Irsil CJ 26, 1956. -4;,1, f'r,, air A-4 pril 26 1955 N\ 123,j' 5t'sy ee >eciflcutiovb Pulb 1 isletti: Oct 2,', 19-f. Index at Acceptance:-Class 60, D 2 GT 3 C. International Classification: 324 d. COMPLETE SPECIFICATION. Improved Polishing or Buffing Mop. ERRATTUM SSPECIFICATION ';O 7 P 5,330 In -he heading on age 1, for n April 2 C, 1955 " read P April 29, 1955 ", T.h E PATENTT OFFICE, 12th 'P arch, 19058 DB 03933/2 ( 4)/3653 150 3/58 R ing or polishing of an article. The object of the invention is to provide an improved construction of polishing buff Or mop. According to the invention, we provide a 2 O polishing buff comprised of an annulus of fabric or other buffing material mounted on a rigid centre piece, said centre piece comprising two metal discs, which are adapted to be secured to one another by providing one disc with a plurality of holes and the other disc with a plurality of corresponding holes and axially directed projections adjacent and surrounding some or all of said holes such that when the two discs are assembled together the said axially directed projections of the one disc may enter into and project from the said holes or some of the appropriately positioned holes on the other disc so that the discs mav be rigidly :-3 secured together by turning the said projections on one disc outwardly over the edges of the holes in the other disc through which the projections have entered and from which they project, whereby the two discs are tightly gripped together. r Price 3 s 6 d rice 4 S 61 mounting the butts on a spincue, eacn o O the aforesaid metal discs is preferably provided with a central hole

through which a spindle can be passed, the central hole of at least one metal disc in each polishing buff being provided with an axially directed projection or flange which provides a bearing surface for supporting the buff on the spindle. Further, in order to obtain a tighter grip on the annulus of buffing material we preferably provide one or both of the aforesaid laterally extending flanges with an inturned, axially directed lip at its outer edge. such lip biting into the buffing material when said flange is bent towards and on to said buffing material. We may also provide, for the purpose of obtaining a tighter grip on the buffing material, a plurality of gripping teeth which are formed in the rim or rims of one or both metal discs, each of said teeth being conveniently formed by means of pressing out a tongue of metal which can be bent from the rim so as to be forced into the buffing material. .3 So -',1 4 t r We, JOHN HAWLEY & CO (WALSALL) LIMITED, a British Company, of Goodall Works, Bloxwich Road, Walsall, in the County of Stafford, 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 polishing buffs or mops in which a plurality of layers of fabric are mounted on a rigid support which is adapted to be rotated so that the rotating wheel so formed may be used for the finishing or polishing of an article. The object of the invention is to provide an improved construction of polishing buff or mop. According to the invention, we provide a polishing buff comprised of an annulus of fabric or other buffing material mounted on a rigid centre piece, said centre piece comprising two metal discs, which are adapted to be secured to one another by providing one disc with a plurality of holes and the other disc with a plurality of corresponding holes and axially directed projections adjacent and surrounding some or all of said holes such that when the two discs are assembled together the said axially directed projections of the one disc may enter into and project from the said holes or some of the appropriately positioned holes on the other disc so that the discs may be rigidly secured together by turning the said projections on one disc outwardly over the edges of the holes in the other disc through which the projections have entered and from which they project, whereby the two discs are tightly gripped together. lPrice 3 s 6 d Arice 4 S 6Conveniently one or both of said metal discs is or are provided with a laterally extending flange which is adapted

to form a trough shaped annular recess when the discs are disposed in an assembled operative relationship so that the inner edge of the annulus of buffing material may be inserted within said recess and afterwards gripped therein by bending the said flange or flanges in an axial direction towards the annulus of buffing material. A plurality of such polishing buffs are usually mounted on a spindle which is rotated so as to form a polishing wheel. In order to provide a simple method of mounting the buffs on a spindle, each of the aforesaid metal discs is preferably provided with a central hole through which a spindle can be passed, the central hole of at least one metal disc in each polishing buff being provided with an axially directed projection or flange which provides a bearing surface for supporting the buff on the spindle. Further, in order to obtain a tighter grip on the annulus of buffing material we preferably provide one or both of the aforesaid laterally extending flanges with an inturned, axially directed lip at its outer edge, such lip biting into the buffing material when said flange is bent towards and on to said buffing material. We may also provide, for the purpose of obtaining a tighter grip on the buffing material, a plurality of gripping teeth which are formed in the rim or rims of one or both metal discs, each of said teeth being conveniently formed by means of pressing out a tongue of metal which can be bent from the rim so as to be forced into the buffing material. 785,330 PATENT SPECFICATION Inventor: -SIDNEY JAMES HAWLEY. -l, of filingy (s Complete Specification: April 26, 1956. Application Date: April 26, 1955 No 12386/55. Co(wplete Specification Published: Oct 23, 1957. Index at Acceptance:-Class 60, D 2 G 3 C. International Classification:-B 24 d. COMPLETE SPECIFICATION. Improved Polishing or Buffing Mop. 785,330 The invention will now be more particularly described with reference to the accompanying drawing wherein:Figure 1 represents a plan view of a polishing buff constructed in accordance with the present invention. Figure 2 is a sectional side elevation of part of Figure 1, being taken on the line 2-2 of Figure 1. I J The centre piece of a polishing buff is comprised of two circular metal discs 10 and 11 each of which is conveniently formed in a pressing operation or series of pressing operations The metal disc 10 is formed from a flat, circular blank which is subjected to a drawing or bending operation which forms a laterally extending flange 12 on the blank The centre of the disc is provided with a hole 13 centred on

the axis 2 li of the disc through which the spindle of the polishing or buffing machine may be passed This central hole 13 is provided with an axially directed flange 14 which projects on the same side of the disc as the aforementioned laterally extending flange 12 This central hole 13 and axially directed flange 14 can be formed in any convenient manner For example, a circular depression ca,n ke pressed into the centre of the disc :3 o and then the bottom is pierced oplt of the said circular depression so that we are provided with a central, circular hole 13 which has an axially projecting flange 14 (which formed the walls of the aforesaid circular 3.5 depression) around its edge This axially projecting flange 14 provides a surface which supports the disc 10 when the latter is mounted on a rotatable spindle. Between the aforementioned central hole O with its axially directed flange 14 and the said laterally extending flange 12 on the outer part of the disc is a flat or substantially flat centre portion. In this flat centre portion there are pierced a plurality of holes 15 arranged so That they are equally spaced on a circle which is concentric to the axis of the disc Some or all of said holes 15 are provided with axially projecting flanges 16 in a manner similar to that used to provide the axially projecting flange 14 In the embodiment shown in Figure 1 half only of the holes 15 are provided with axially projecting flanges 16, this being done to aoid unnecessary expense. As 5 Said axially projecting flanges 16 are provided for the purpose of securing the two discs together as will be apparent in the following description. Between the said flat centre portion and ail the said laterally extending flange 12 there is provided at one stage of the pressing operation a small connecting flange 17 which projects in a substantially axial direction. This said small connecting flange 17 thus 3.5 joins the flat central portion to the laterally extending flange 12, the latter being thereby offset from the flat central portion Similarly, a flange 17 may be formed in the disc 11, and in this way, when two discs 10 and 11 are placed back to back, there is provided 7 o an annular trough shaped recess, the bottom of which has a width equal to twice the width of said small connecting flange 17. The other metal disc 11 is also provided with a plurality of holes corresponding in 7,5 position and number to the holes 15 provided in disc 10 but the holes on disc 11 do not have the axially projecting flanges 16 which are provided on some of the holes of disc 10 Furthermore, the centre portion of Aso disc 11 is cut away as may be seen from Figure 2, this being done to reduce weight.

Said disc 11 is also provided with a laterally extending flange 12 and the small connecting flange 17 as may also be seen from >. Figure 2; the flange 17 may, however, be omitted On assembly the two discs are placed together so that the holes 15 in the disc 10 register with the corresponding holes in the disc 11 and the projections 16 are lt then spun or pressed over the edges of the holes in disc 11 so that the two discs 10 and 11 are fastened together as indicated in Figure 2. In order to obtain a better grip of the ll;, annulus of buffing material 18 when it is placed in the said trough shaped recess said laterally extending flanges are provided with a small axially directed flange or lip 19 on their outer edges, said lips 19 projecting in a loo direction which will point towards the inside of the aforementioned trough shaped recess. The annulus of buffing material 18 can then be inserted into the trough shaped 105 annular recess formed by the two laterally extending flanges 12 and said flanges 12 are compressed or bent towards one another, gripping the buffing material between them, the said small outer lips 19 helping to pro ies vide a more firm grip. In order to provide a still firmer grip on the annulus of buffing material we also provide in the laterally extending flange 12 of each metal disc a plurality of tongues 20 115 which are conveniently formed by means of pressing out from the metal a number of "V" shaped indentations, the point of the -V"' being detached from the metal so that the tongues can then be pressed inwardly so 120 as to grip the buffing material as shown in Figure 2 Preferably the tongues in each metal disc 10 and 11 are sta Rgered in respect of each other when the polishing buff is assembled 125 The buff is completed by means of a row of stitching 21 which sews together the layers of the buffing material, said stitching 21 being carried out in a circular line surh 5,330 rounding the outer edge of the metal discs and 1. A complete polishing mop or wheel can be built up by mounting several of the above described polishing buffs on a common spindle, a bearing being provided between each buff and the spindle by means of the axially directed flange 14 and by reason of the holes 15 provided in each 1) polishing buff a substantial amount of air can flow through the wheel so as to provide a cooling effect which is of considerable advantage when the polishing wheel is used in conditions where a certain amount of heat is generated.

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* GB785331 (A)

Description: GB785331 (A) ? 1957-10-23

Improvements in condensers made of paper impregnated with poly-chloronaphthalenes



BE544729 (A) CH338527 (A) FR1109198 (A) SE158778 (C1) BE544729 (A) CH338527 (A) FR1109198 (A) SE158778 (C1) less Translate this text into Tooltip



PATENT SPECIFICATION 7859331 Date of Application and filing Complete Specification May 3, 1955. - % i No12846155. cl Application mode ii Complete Specificat Index at Acceptance:-Class 37, D 1 (G 4: 34 M). International Classification: -H Olg. i France on July 19, 1954. ion Published Oct 23, 1957. CO Mi PLLETE SPECIFICATION Improvemeits in Condensers made of Paper Impregnated with P Foy-Clhliororiaphtbaienes We, " PROGIL ", a Thrench Body Corporate, of

1, Quai de Serin Lyon (h Lone), France, too nereby 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: - It is a well-lnown fact that polychioronaphthalenes used as dielectrics tall into two categories whose behaviour in a paper impregnated therewith is very different (see Igor Belic, Arhiv za Kamijut XX 1948 p 61). T he compounds of the first category, generally constituted by polychloronaphthalenes the chlorine contents of which are approximateiy 50 % and less, and the melting points of which are comparatively low and below 100 l C, give the paper a high specific inductance capacitance corresponding to a specific inductive capacitance of the impregnating material which approximates 5, i e. which is not very different from the value measured on the chloronaphthalene formed in plates of substantial thickness. In contrast, the compounds of the second category generally constituted by polychloronaphthalenes the chlorine contents of which are higher than 50 % and the melting points of which are higher than 100 ' C, give the impregnated paper a lower specific inductive capacitance corresponding to a specific inductive capacitance of the impregnating material approximating to 2 5, although the specific inductive capacitance which may be measured on plates of chloronaphthalene is of a magnitude equal to 5 as in the case of the first category. Whereas the specific inductive capacitance of paper impregnated with polychloronaphthalenes of the first category is actually unvarying with time, this is not the case for paper impregnated with polychloronaphthalenes of the second category A very slow maturing takes place the speed of which increases through heating to a temperature lower than the point of softening, and has for its conselPrice 3 s 6 d l quence a slow rise in the specific inductive capacitance of the impregnated paper so that after a comparatively long time this capacity reaches a value similar to that of paper impregnated withl a substance of the first category. This phenomenon is ascribable to a difference in crystallizing structure The substances of the second category are in a crystalline state such that they lose their polarity when crystallizing as a thin layer in the paper while those of the first category retain their polarization in such a case, both categories of polychloronaphthalenes retaining their polarity when crystallizing in thick layers However, a slow transformation causes the dipoles of the second category of polychloronaphthalenes to be gradually given a degree of freedom such that the substance is again provided with the polarity it had almost

entirely lost during its crystallization inside the paper body. In the general case and as disclosed hereinabove, the substances of the first category have melting points and chlorine contents which are lower than for the substances of the second category, but this distinction is not an absolute one and it is possible to find chlioronaphthalenes having a comparatively low melting point and a comparatively small chlorine content, which fall however inside the second category through their crystalline structure and their behaviour, while conversely other substances having comparatively high melting points and comparatively large chlorine contents behave in the same manner as the substances of the first category. Substances of an intermediate category are also kmown By intermediate is meant that their behaviour lies between that of the first category and that of the second category, their crystallization inside the paper body leading only to a partial loss of their polarity These intermediate substances seem; to be constituted by mixtures of substances of both categories and appear to be capable of maturing in the same manner as those of the second category but obviously with a lesser modification of the 785, 331 s'pecific inductive capacitance of the impregnated paper. These conditions limit the use of chloronaphthalenes of the second category for the impregnation of condensers, although they show a melting point which is generally higher and consequently often of a mole practical interest than those of the substances of the first category Immediately after impregnation, the capacity of the condensers is almost as low as if the paper had been impregnated with paraffin wax, ozokerite or the like nonpolar wax, but through maturing their capacity rises gradually and slowly reaches a value which is generally higher by 22 to 25 % than the original value This modification in capacity is inconsistent with the close allowance within which the capacity of condensers is generally required to be held Furthermore, maturing through heat-treatment is too slow for it to be tehnically applicable. According to the invention, there is provided a method of preparing a condenser of a high stable capacity comprising a paper winding impregnated with polychioronaphthaiene of the second or intermediate category as hereinbefore defined, wherein the impregnated paper is subjected to an A C voltage gradient of at least 7 rms volts per micron or to a D C. voltage of at least 12 volts per microm while the impregnant is still in the molten state, the voltage gradient being maintained during the cooling and resulting crystallization of the impregnant whereby the polarity of the impregnant is retained. This capacity is no longer liable to change subsequently, except of

course if the condenser is brought to a temperature such that the impregnating material is submitted to a partial or complete melting and then allowed to cool without being subjected to a voltage gradient. The substances of the intermediate category are also improved by such a treatment so that the application of our method allows an unvarying high capacity to be obtained with any type of polychloronaphthalene adapted for use in the impregnation of paper. The minimum voltage gradient required for obtaining a practically complete and satisfactory result is equal to about 7 rms volts per micron in the cases of an A C voltage and it should reach 12 volts per micron in the case of a D C voltage When lower gradients are used, the result is incomplete and the condenser capacity is capable of further modifications. Such voltage gradients are readily withstood by condensers made of paper impregnated with a polychloronaphthalene of standard grade It is however possible to protect the supply of voltage through a fuse or a circuit breaker adapted to operate upon break-down of the dielectric of the condenser as a consequence of an internal defect and this procedure may be thus considered also as a substitute for a testing of the condenser dielectric. i-owever, this procedure is quite difterene from tne conventional testing o condenset. tlarough application or a voltage since in the AJ present case twe voitage is applier L to a conoenser which is brought to a temperature nigh enough for tie melting of tile impregnating material and is held under tais voltage during tue crystallization oi the impregnating sub 75 stance wh Wie on the contrary in the conventional testing the voltage is applied to tne condensei at a temperature which is lower than the meiung point of tie impregnating substance Experience shows that in this latter 8 o case the action of the voltage on the capacity is very small. The short duration of the subjection to the voltage owing to the natural cooling of the condenser may be still further reduced by 85 cocting tie condenser artificially. We: ish to give nereinafter by way of exempivication w-ithout any binding sense being attached thereto the caaracteristic data reiating to three condenser wincings obtained 90 in accordance with our invention. EXAMPLE I. Windings formed by three layers ot paper having a specific weight or approximately one with a constant thickness of 10 micions hau a 95 capacity of approximately O ito microfarads at 2 UW G after drying. These condensers impregnated in accordance withl me conventional

method witn a polycinoronaphthalene having a cnlorine con 100 tent of 55; O and a melting point of 117 C. Uad a capacitance in thle neignbourhooa of 0.20 microfarads, i e equal to that which it was possible to obtain by impregnating an identical winding with an impregnant having 105 a specinc inductive capacitance of 2 5 The capacitance oi identical coils from the same batch impregnated with the same polychioronaphthalene, but subjected to an alternating voltage gradient of 280 effective volts in ute 110 course or the crystallisation oi the impregnant was brought to a value in the neighbourhood of 0 25 microfarads, which value could be attained by impregnating identical coils either with chlorinated diphenyl having a specific 115 inductive capacitance of 5, or with a polychloronaphthalene of low melting point ( 95 C.) belonging to the first type The application of voltage to tue winding impregnated with polychloronaphthalene having a melting point 120 of 117 C during the crystallisation of the impregnant thus resulted in a capacitance 25 % higher than that of condensers impregnated with the same product, but cooled naturally. On prolonged heating in an oven at 800 C 125 the capacitance of the condensers impregnated with polychloronaphthalene having a melting point of 1170 C, but not subjected to a voltage gradient, which capacitance initially i 785,331 amounted to 0 20 microfarads, progressively increased fairly rapidly in the first few days, and then at a constantly reduced rate, reaching a value of about 0 25 microfarads at the end of several months The capacitance of identical condensers maintained at a temperature of 30 C had increased by 8 % at the end of one month and by 14 % at the end of one year, and this increase had not finished after this period of observation. On the other hand, the capacitance of condensers comprising the same impregnant, but which had been subjected to a voltage gradient, remained substantially unchanged, whether heated in an oven at 800 C or maintained at a temperature of 30 C side by side with the aforesaid condensers. Ex AMPLE II. Windings similar to those referred to in Example I were impregnated with a polychloronaphthalene similar to that of Example I, and were subjected to a D C voltage of 500 volts during the crystallization of the impregnating material They acquired thus a capacity approximating 0 25 microfarad at 20 C and this high capacity remained the same after a protracted heating to a temperature of 800 C. EXAMPLE III. Windings similar to those referred to in Example I were impregnated with chloronaphthalene having a chlorine content of 60 % and melting completely at 1350 C Mere natural cooling being applied, their

capacity reached a value of 0 19 microfarads, whereas when cooled while a voltage of 280 r m s. A.C volts or of 500 D C volts was applied during the crystallization of the impregnating substance a capacity of 0 25 microfarads at C was obtained Thus the capacitance of the windings was increased by 31 5 % by the application of an appropriate alternating or direct voltage This capacitance increase of 31.5 % remained unchanged despite prolonged heating at 800 C, while the capacity of reference condensers impregnated with polychloronaphthalene in the same manner but not subjected to the action of an electric voltage changed progressively, but at a still slower rate than that of the similar condensers mentioned in Example I.

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* GB785332 (A)

Description: GB785332 (A) ? 1957-10-23

Improvements in or relating to defoliants



BE538246 (A) CH344592 (A) FR1131562 (A) BE538246 (A) CH344592 (A) FR1131562 (A) less Translate this text into Tooltip


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and information originating from other authorities than the EPO; in particular, the EPO does not guarantee that they are complete, up-to-date or fit for specific purposes.

COMPLETE SPECIFICATION Improvements in or relating to Defoliants We, ETHYL CORPORATION, a corporation organised under the laws of the State of Delaware, United States of America, of 100, Park Avenue, New York 17, State of New York, United States of America, do hereby dedare the invention, for which we pray tfiat 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 the defoliation of plants. In particular, it relates to compositions suitable for causing leaf drop in cotton and other plants as an aid to harvest operations. It has been recognized for many years that successful defoliation of cotton- plants would produce large improvements in agricultural operation associated with harvest of the cotton boll. The greatest detriment to widespread use of mechanical cotton pickers has been the difficulty entailed in mechanically picking the boll without introducing into the harvest a significant quantity of the leaf of the cotton plant. The presence of the leaf in the harvest interferes with the mechanical operation, and even more serious is the staining effect which the leaves have upon the white cotton fiber. It is well known that during the normal life process of cotton plants the leafy portions drop as a result of changes in a group of specialized cells at the base of the petiole. The outward effect is the development of an abscission layer composed of meristematic cells developed across the base of the petiole. The mechanism of these changes is essentially little understood, but a number of external, naturally occuring factors are known to produce this inner growth effect. For example, a decrease in ambient temperature at the proper period in the life cycle of the plant causes the natural formation d the abscission layer. Likewise, an injury through disease or adverse growing conditions will be conducive to such abscission layer, resulting in the sloughing-off by the plant of the injured member. A number of additional causes d natural origin bring about defoliation. None of the above methods of defoliation is available as means for controlling defoliation at will. A few attempts have been recorded to bring about such defoliation at the desired period in the life cycle of the plant. Such prior methods have been inadequate in that injury

to the plant and a consequent decrease in crop yield results, defoliation is incomplete, secondary effects of an undesirable nature are produced, or the applied materials are nonadherent or removed by weathering, resulting in the necessity for repeared and costly applications, or must be applied during a limited and critical period during the growing season. Although cotton is presently the crop in which defoliation operation is most important, defoliation is also of significance with regard to many other crops, such as beans and the like. According to the present invention we pro vide defoliant compositions comprising as conditioning agent a dispersing agent or a surface active agent as herein defined and, as an active defoliation ingredient, a compound having the zroUTwinz - <img class="EMIRef" id="026598875-00010001" /> we nave round that compounds having this grouping possess outstanding defoliation proparties and when applied to crops or other materials cause defoliation without injury to the plant and to produce such defoliation at any time desired in the life cycle of the plant. By suitable substitution of radicals or ions on the basic structure given above1 the important properties of puissance, stability, oil and water solubility, state of aggregation, melting point, dispersability, phytotoxicity, and the like can be augmented by the user to suit the need of the particular defoliation problem. Compounds containing the above basic group can be represented by the following formula:- <img class="EMIRef" id="026598875-00010002" /> in which the four butyne carbon atoms are numbered 1 through 4 for the sake of clarity in the following discussion. In the above representation R and Rl can be the same or different and can be hydrogen or organic radicals. When they are organic, they can be aLphatic, ali- cyclic, aromatic, or heterocyclic, and are preferably hydrocarbonaceous; that is, are unsubstituted alkyl, alkenyl, aryl, or cycloalkyl. However, R and R1 can be substituted with various atoms and radicals, and in many cases this substitution leads to enhancement of desirable properties of our materials Such substitution can be in the form of halogen, hydroxy, substituted hydroxy, carboxy, substituted carboxy, nitro or amino. X and Y can be the same or different and can be hydrogen, any of the organic groups described for R and R1, preferably hydrocarbonaceous, and can also be salt-forming groups, either inorganic or organic. Thus, X and Y can be metallic ions, preferably alkali metal ions, ammonium ions, or substituted ammonium ions. The simplest as well as one of the most effective of our material is that obtained when

R, R1, X, and Y are all hydrogen-1,4-butynediol, a preferred active ingredient of this invention. Typical representatives of the active ingredients of the present invention include 1,4butynediol, 1,4dimethyl-1,4butynediol, 1ethyi-1,4butynediol, 1-butyl-1,4butynediol, i-hexyl-1,4'butynediol, l-dodecyl-l,Sbutyte- diol, 1-phenyl-1,4-butynediol, 1-p-tolyl-1,4- butynediol, l-methyl4-ethyl-1,4-butynediol, 1-methyl-4-amyl-1,4-butynediol, l-methyl-4- do decyl- lA-butynediol, 1-butyl-4o ctyl-1,4 butynediol, 1,4-diisopropyl-1,4-butynediol, 1,4 dimethoxy-butyne-2, 1,4 - diphenoxybutyne-2, 1-methoxy-4 < -chlorophenoxy- butyrie, l-butoxy-Sphenoxy-l-methyl- butyne-2, 1,4-diphenyl-1,4-diphenoxy-butyne- 2, 1-methoxyhdroxy-bityne-2, l-hexoxyw 4hydroxy4amyl-butyne-2, diso dium-1,4 butynediol, calcium-l,Sbutynediol, potassiuml,Sbutynediol, amyl-1,4-butynediol, pyridinium-1,4butynediol, trimethyl-amyl-lphenyl-1,4butynediol and 1-(y-pyridyl)-1,4 butynediol. The compounds of the present invention can be prepared by reaction of acetylene with aldehydes. For example, the reaction of acetylene with 2 moles of formaldehyde yields the simplest active ingredient of this invention, l,Sbutynediol. This can be connected to its various salts by reaction with the appropriate base; viz. reaction with sodium alkoxide yields disodium 1,4butynediol, and reaction with tetraethyl ammonium hydroxide forms the corresponding diammonium salt Reaction of 2 moles of acetaldehyde with acetylene yields 1,4dimethyl-1, Sbutynediol; reaction of 1 mole of acetylene with 1 mole of acetaldehyde and with 1 mole of benzaldehyde yields l-methylOphenyl-l, 4butynediol, and so on. The compounds wherein one or both of the hydroxyl hydrogens are replaced with an organic group can be prepared by reacting the corresponding diol with sodium alcoholate to form the sodium salt of the diol which can then be reactive with an organic halide to yield the ether derivative. For example, 1 mole of 1-buyl-1,4-butynediol is reacted with 2 moles of sodium ethylene to yield the disodium salt of the above named compound. This, on reaction with 2 moles of ethyl bromide, yields 1,4diethoxy-1-butyl- butyne-2. Similarly l,4butynediol (1 mole) is reacted with 1 mole of sodium methylate, and the monosodium salt thus formed is reacted with 1 mole of n-butyl bromide to yield l-butoxyffihydroxy-butyne-2. The above and the other butyne derivatives of the present invention have been found to possess outstanding defoliant properties, as will be shown below. It is not sufficient to apply the active ingredients as above without regard to the other ingredients of the defoliant composition. It is important that the plant remain actively growing after defoliation

occurs. It is a part of this invention to provide such active material formulations which, when applied, cause defoliaticn but at the same time permit other normal functions of the plant to continue. Thus, in general, we apply the active ingredient with an adjuvant as conditioning agent which has the function of providing a dispersing or surface-contacting action without phytotoxic effects. One purpose of such conditioning agents is to provide a medium whereby the active ingredient is placed in proper contact with the plant surface, and whereby it can be absorbed into the plant system and thereby cause defoliation. Another purpose of such surface-contacting adjuvants is to permit the application of such materials in a uniform manner on the plant surfaces and in the appropriate minute quantities required; that is, in those proportions required by the characteristics of the plant and the seasonal requirements. The formulations which are useful in conducting the present invention are generally those in which the active material is admixed either in concentrated or in dilute form with a conditioning agent which provides means of applying the active ingredient to the surface of a growing plant but which at the same time does not itself introduce phytotoxic properties to the formulation. In general, such non-phytotoxic conditioning agent can be either dry or wet, thus providing both liquid and solid formulations. Typical examples of such dry non-phytotoxic carriers which are useful as conditioning agents include relatively inert dusts or powders, both organic and inorganic. In such formulations it is preferred to employ a surfaceactive agent to improve the contact between the formulation and the plant. However, certain solid carriers in themselves are considered as being of the wetting type, and in such instances it is not essential that a surface-active agent be employed therewith, although improved results may be so obtained. Dry or dust formulations of the defoliant compositions can either be in such dilution of the active ingredient as to be directly applicable to the plant or can be in concentrated form. For further dilution with non-phytotoxic carriers of either the dry or wet type for ultimate application in the field it is frequently desirable in the concentratddry formulations to employ therewith a surface-active agent such that upon dilution with a liquid carrier an adequate dispersion is obtained. In liquid formulations of the defoliant composition of this invention it is likewise necessary to employ a liquid which in the ultimate concentration of application to the plant surface renders such formulation relatively nonphytotoxic. Typical examples of liquids suitable for this purpose include various hydrocarbon liquids or oils. Although the cotton plants to which our defoliants can be profitably applied usually exist in aqueous environment, one very effective

method of applying our defoliants is in the form of organic or oil solutions, suspensions, or emulsions, as the adjuvant. One particular advantage of this type of surface-contacting formulation is that even under extreme conditions of high humidity or rainfall the defoliant materials adhere tenaciously to the plant surface. Aqueous dispersions or solutions of our defoliants can also be applied to the crops with good effect. The salt forms are especially useful in this regard. Where the conditions under which application is being made permit the use of dust formulations, we have found that our defoliants can be employed in this form with effective results. We have found that certain solid carriers as conditioning agents perform the function of providing a surface-contacting agent in certain applications equally effectively as the above mentioned oily or aqueous formulations. A further advantage of employing our defoliants in dust formulations resides in the organic nature of the defoliant; that is, here again our materials are not dependent upon the fortuitous deposition of the proper amount of moisture in the form of dew as has been the experience in attempting defoliation with dry formulations of previously suggested defoliants. One method of applying our defoliants is in the form of an oil solution wherein the materials are dissolved in a hydrocarbon oil as typified by kerosene, oil, xylene, and nonherbicidal petroleum oils, in particular those of weight or viscosity, in concentrations between the limits of about 0.1 and 25 weight per cent. In such formulations we believe the oil itself to be the surface-contacting agent or adjuvant, an effect which is brought about by the peculiar nature of the upper leaf surface wherein a waxy cuticle exists permitting the initial contact between the defoliant and the actual plant surface in the presence of the oil to be achieved. The following example illustrates methods of preparing such defoliant compositions : - EXAMPLE I. To 100 parts of mineral oil is added 1,4butynediol in the amount of 5 parts. A composition suitable for application is made from this concentrate by further diluting with the oil to a final butynediol 'concentration of 0.5 weight per cent. When applied to cotton plants, the above formulation exhibits effective defoliation. Likewise, similar oil formulations of 1,4diphenylHl74-butynediol, 1,4-dibutyl-1,4- butynediol, l-methoxyWhydroxy-butyne-2, 1methyiA-butyl-1,4-butynediol, and the like can be prepared. Other oils, such as kerosene, toluene, cumene, and so on can be used with good results, and these oil formulations can have incorperated within them surface-active agents such as those illustrated below.

For certain applications the defoliant compositions of this invention are preferably employed suspended in the conditioning agent. Such suspensions can be made by one of the following methods: A concentrated oil solution of the active ingredient is prepared, and this is added to water containing a dispersing agent; a solution of one of the defoliants in a water-soluble solvent is prepared which is thereupon added to water containing a dispersing agent; or a water suspension of the defoliant is prepared and added to an oil in the presence of a dispersing agent Thus, either a water and oil emulsion or a solid dispersions of the active ingredient can be prepared. Examples of typical dispersing agents which can be employed in forming dispersions include salts of the alkyl and alkylaryl sulfonates, such as the sodium salt of sulfonated ethyloleate, the sodium salt of sulfonated oxidized petroleum oils, dioctylsodium sulfosuccinate, sodium decylbenzene sulfonate, potassium dodecylbenzene sulfonate, and the sodium salt of sulfonated ethyloleylamide; alkyl sulfates, such as sodium lauryl sulfate, sodium oleyl sulfate and ammonium ricinoleyl sulfate; alkylaryl polyether alcohols, such as alkyl, phenoxy, plolyethoxy-ethanol (alkyl can be methyl to C20), the condensate of ethylene oxide and alkylated cresol, and polyoxy ethylene thio-ether; fatty acid esters of polyhydric alcohols, such as mannitan monolaurate, and sorbitan monooleate; and the ethylene oxide addition products of such esters, such as the polyoxy ethylene derivative of sorbitan monooleate. The following examples typify methods of preparing the above formulations: EXAMPLE II. A formulation of 1,4butynediol is prepared by intimately admixing 10 parts of this material with; 90 parts of water containing 0.1 part of polyoxyethylene thio-ether. Ten parts of this aqueous suspension is thereupon added to 190 parts of T-942-B to form a final formulation consisting of 0.5 weight per cent of 1,4-butynediol in an oil-in-water emulsion containing a surface-active agent. This material in its final dilution is an effective cotton defoliant. Equally good oil and water emulsions are similarly prepared from the following materials; 1-methyl-1,4butyndiol, 1-butylX heptyl-1,4butynediol, 1-meta-tolyl-1,4-butynediol, 1,4-diethoxy-butyne-2 and I,tdi-lz-proi pyl-l-methoxyXhydroxy-butyne-2. EXAMPLE m. A 10 per cent solution of 1-methyl-1,4 butynediol is prepared in methyl alcohol, and the resulting solution is added to 100 parts of water containing 1 part of sodium lauryl sulfate to provide an aqueous suspension comprising 1 per cent of the active ingredient in an

alcohol-water mixture. In a similar manner we prepare such suspensions of butynediol, 1,4diphenyl-butynediol, l-decyl-l,Sbutynediol, and similar materials with equal effectiveness. Other organic solvents which may be used in such formulations include carbitol, cellosolve, methyl cellosolve, acetone, isophorone, methyl isobutyl ketone, methylethyl ketone, and isopropanol. A variety of surface-active agents of the type illustrated above may be used. EXAMPLE IV. A mixture of 50 parts of 1,4diethoxy- butyne-2, 100 parts of bentonite, and 0.5 part of calcium dodecylbenzene sulfonate is treated in a ball mill for a period of onehalf hour. At the end of this period the mixture is screened to pass a 100-mesh sieve. This 50 weight per cent wettable powder formulation is further treated to form a suspension suitable for application by adding with agitation 100 parts of the wettable powder to 1000 parts of water. The resulting aqueous suspension of the solid surface-contacting agent and defoliant is suitable for spraying directly upon crops. The butynediols of this invention can also be incorporated with Fuller's earth, talc, pyro phyllite, clays of various types, walnut shell flour, and the like, with or without surfaceactive agents to form good solid formulations. EXAMPLE V. An emulsifiable concentrate is prepared by treating 10 parts of 1,4diphenoxy-1-p-toWl- butyne-2 with 65 parts of cyclohexanone, 20 parts of xylene, and 5 parts of sodium alkylaryl sulfonate. This concentrate is further agitated with water so as to contain 1 per cent 1,4-diphenoxy-1-p-tolyl-butyne-2 to make an effective defoliant formulation. Typical of the butynediols which can be so formulated to provide efficient defoliating formulations include 1,4butynediol, 1,4-diethyl-1,4-butynediol, 1-methyl-4n-propyl- 1,Abutynediol, 1 butyl-1,4butynediol, 1,4Zipropoxy-butyne-2, and the like. For certain applications, particularly when defoliants are applied to plants during the active growing season and regrowth of new leaves might occur and be undesirable, it is possible to employ along with these defoliants any of several agents designed to stunt the growth of the plant. A typical example of such materials is maleic hydrazide. In addition to maleic hydrazide it is sometimes desirable ta employ a material such as sucrose to enhance the ability to prevent regrowth of the leafy structures of the plants. Furthermore, an adherent agent can be employed along with such defoliants, if this is desired, without interfering with the activity thereof. Likewise; it is possible to employ humectants along with the defoliants, particularly when dry

formulations are employed. A number of methods are available for applying the defoliants of this invention, including power driven spray, hand spray, aircraft spraying, and the like. The materials of this invention are particularly advantageous in the latter method of application in that the oil formulations illustrated above can be employed to advantage in that good adherence and little drifting is encountered. Thus, one of the major drawbacks to the commercial utilization of previously suggested defoliants has been overcome by this embodiment of the invention. The quantity of active ingredient present in the surface-contacung defoliant compositions is not critical. It is preferred to employ the defoliant ingredient in amount between about 0.1 and 25 per cent by weight. Concentrates as above may vary from about 20 to about 80 weight per cent. active ingredient. The amount of defoliant formulation applied to a crop depends, of course, on a number of variables. For example, the greater the number of leaves and leaf surfaces exposed per acre, the greater the amount of defoliant required. Similarly, the species of genus of plant defoliated will be a determining factor. Furthermore, the period in the growing season as well as the conditions under which the plants are grown is important. Thus, tough leaves grown in arid climates generally require more defoliant than lush new growths. The defoliant activity of the present compounds can be illustrated as follows. Young cotton plants averaging 6 to 7 leaves per plant were sprayed with a 1 per cent aqueous dispersion of 1,4-butynediol. After 14 days all the leaves had dropped from the plants with no harm to the remainder of the plant. Furthermore, when applied as a 1 per cent paste in lanolin to the leaves of soybean plants, good defoliation was obtained. Good defoliation results are also obtained using the other active ingredients as above defined. What we claim is: 1. A defoliation composition comprising as conditioning agent a dispersing agent or a surface active agent as herein defined and, as an active defoliation ingredient, a compound having the grouping -O-CH-C C-CH-O-. 2. A defoliation composition comprising as conditioning agent a dispersing agent or a surface active agent as hereon defined and, as an active defoliation ingredient, a compound of the formula <img class="EMIRef" id="026598875-00050001" /> wherein R and R1 can be the same or different and are selected from

the group consisting of hydrogen and organic radicals and X and Y can be the same or different and are selected from the group consisting of hydrogen, organic radicals, and salt-forming groups. 3. A defoliation composition comprising a conditioning agent as herein defined and 1,4 butynediol. 4. A defoliating composition substantially as herein defined.

Law

4921 4925.output