Classifications

• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D10/00—Compositions of detergents, not provided for by one single preceding group
  • C11D10/04—Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap
  • C11D10/045—Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap based on non-ionic surface-active compounds and soap
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
  • C11D1/66—Non-ionic compounds
  • C11D1/662—Carbohydrates or derivatives
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
  • C11D1/66—Non-ionic compounds
  • C11D1/667—Neutral esters, e.g. sorbitan esters
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D9/00—Compositions of detergents based essentially on soap
  • C11D9/04—Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
  • C11D9/22—Organic compounds, e.g. vitamins
  • C11D9/26—Organic compounds, e.g. vitamins containing oxygen
  • C11D9/262—Organic compounds, e.g. vitamins containing oxygen containing carbohydrates

Definitions

• the detergent composition comprises essentially a mixture of a soap component with a sucrose ester component which comprises at least one sucrose esster of fatty acid having 6 to 22 carbon atoms.
• the detergent composition may further include a saccharide component.
• the invention relates to new and improved detergent compositions, particularly to hazardless detergent compositions having improved detergency.
• ABS alkylbenzene sulfonate
• This detergent has a good detergency and is economical to manufacture and in this sense it may be said to be one of most desirable detergents.
• such detergent has caused various problems partly because it is used in increasing amounts. Thus, it causes a foam public hazard to sewage disposal facilities and rivers to which it is discharged. Further, the pollution of undergound water has recently become a problem, giving birth to various rum about adverse effects on the human body. This is due to the fact that ABS is hardly decomposable in sewage water and retains its initial activity for a long time.
• Soap which, stated historically, has been used from of old, has very little toxicity or harmfulness to organisms and is highly satisfactory in biodegradivity, but on the other hand it is disadvantageous in that when it is present in water containing heavy metal ions such as calcium and magnesium, it cooperates with these heavy metals to form a metal soap, which then becomes a water-insoluble scum detracting from the detergency and sticking to the material to be washed to degrade the feeling.
• Such drawbacks of soap result in soap being driven out by synthetic detergents and unable to take over again synthetic detergent, which have caused public hazard problems.
• the primarly object of the invention is to provide a detergent composition which has biodegradivity and causes no public hazard to the human body and which, moreover, is superior in detergency, foamability and foam stability.
• soap has been used as a kind of detergent from old, but because of its very low detergency at low temperatures, its value as a detergent for home use is low.
• oils and fats used as raw materials for soap tallow is used most, accounting for 75-80% of the raw material oils and fats for soap, but the soap made of tallow is also poor in detergency at low temperatures, and in order to develop sufficient detergency it is necessary to heat to 4050C, this being unsuitable to domestic washing conditions.
• Another Object of the invention is to provide a detergent composition superior in detergency at low temperaturcs.
• Detergents used in general homes to wash clothing consist mainly of ABS type surfactants discussed before with builder and other additives incorporated therein in accordance with various purposes. Also, in the case of preparing a detergent which imparts improved feeling and softening effect to the wash after washing, there may be thought of a method of providing the intended softening effect by adding a substance which is generally regarded as having a softening effect to a mixed product which has already been prepared as a detergent. Among these substances regarded as being capable of providing a softening effect there are the socalled textile softening agents. More particularly they are quaternary ammonium salts of higher alkyl amines, dialkyl trimethyl ammonium chloride, and polyamide type compounds of higher fatty acids.
• a further object of the invention is thus to provide an improved detergent composition imparting improved feeling and softness to materials washed with it.
• the detergent composition according to the invention comprises essentially a mixture of a soap component with a sucrose ester component which comprises at least one sucrose ester of fatty acid.
• the detergent composition may further include a saccharide component.
• the sucrose ester component comprises at least one sucrose ester of fatty acid having 6 to 22 carbon atoms.
• the detergent composition according to claim 1 in which said composition comprises a mixture of 75 to 95% by weight of a soap component with 25 to 5% by weight of sucrose ester component, said sucrose ester component comprising essentially at least one sucrose ester of fatty acid having 12 to 14 carbon atoms and by weight of said sucrose ester being monoand di-esters of fatty acid.
• This composition is particularly superior in detergency at relatively low temperatures.
• the detergent composition comprising a sucrose ester component, a soap component and a saccharide component according to another embodiment of the invention has biodegradivity and causes no public hazard to the human body and which, moreover, is superior in detergency, foamability and foam stability.
• the saccharide component may preferably be a monosaccharide or disaccharide or decomposed products of them and may be selected from the group consisting of sucrose, sorbilol and decomposed product of sucrose.
• the detergent composition which imparts softness to materials washed with it according to the invention may preferably comprise to 97% by weight of a soap component and 25 'to 3% by weight of a sucrose ester component, said sucrose ester component comprising essentially at least one sucrose ester of fatty acid having 16 or more carbon atoms and the degree of substitution of said sucrose ester given by the average value of the number of esterified fatty acid molecules per one sucrose molecule being within the range of 1.5 to 3.5.
• the sucrose ester component may further include glyceride.
• the soap component may be a member selected from the group consisting of K and Na salts of saturated or unsaturated fatty acids having 8 to 22 carbon atoms.
• the sucrose ester component may preferably comprise at least 70% by weight of monoand diesters and the remaining part of trior higher polyesters.
• the detergent composition according to the invention comprises essentially a mixture of a soap component with a sucrose ester component.
• the sucrose ester component comprises at least one sucrose ester of fatty acid having 6 to 22 carbon atoms.
• sucrose ester of fatty acid will be referred to merely as SE.
• the detergent composition comprising essentially soap, SE and saccharide has biodegradivity and causes no public hazard to the human body and which, moreover, is superior in detergency, foamability and foam stability.
• the merits obtained by the addition of a saccharide are superior to those ob tainable by the use of any of sodium citrate, tartaric acid, etc. known as hazardless builders. It should be noted that this unexpected result can only be obtained in the case of a combination of a saccharide with a mixture of soap and SE. The addition of a saccharide to soap alone.
• the SEs useful in the present invention are sucrose esters of saturated or unsaturated fatty acids with 622, preferably, l2-l 8 carbon atoms, for example, such saturated fatty acids as laulic acid, myristic acid, palmitic acid and stearic acid, and such unsaturated fatty acids as oleic acid and linolic acid.
• the SE may be either sucrose ester of a sole fatty acid or sucrose ester of a mixed fatty acid comprising a mixture of the above mentioned fatty acids.
• the sucrose ester component may further include a small amount of glyceride.
• the sucrose ester component may be a product produced from fats and fatty oils with sucrose, said product including unreacted or by-product glyceride.
• soaps it is desirable to use, either independently or in combination, Na or K salts of saturated or unsaturated fatty acids with 8-22 carbon atoms, produced from tallow, coconut oil, cotton seed oil, whale oil, palm oil, palm kernel oil, soy bean oil or the like.
• a soap obtained by the saponification of oils and fatts consisting mainly of tallow (in an amount at least 50% by weight) with which is mixed about 50% or less of any other oil such as coconut oil, soy bean oil, etc.
• saccharidesused in the present invention it is desirable to use those belonging to monosaccharides and disaccharides, particularly sucrose or sorbitol.
• De composed products of saccharides are also useful.
• sucrose which in parts has been thermally decomposed by being heated e.g. an unreacted sucrose contained in SE reaction crude product is useful. It is industrially advantageousand economical to suitably adjust and use such crude SE reaction product containing unreacted sucrose.
• the detergent composition of the present invention consisting of soap, SE and saccharide may be used not only as it is but also as a basic component for various types of soaps including toilet soap, light duty detergents and liquid detergents.
• it is also possible to finish it into heavy duty detergents by suitably incorporating therein sodium carbonate, sodium silicate, borax and other alkaline builders, sodium tripolyphosphate, NTA, EDTA, SODA (sodium diglycollate), sodium citrate, sodium polyacrylate and other additives which cooperate with metallic ions to form chelate compounds, fatty acid alkanol amide and other additives which have foam boosting effect, carboxymethyl cellulose, bleaching agents, fluoroescent dyes, etc.
• a detergent composition superior in detergency at relatively low temperatures is provided by utilizing as a base material a mixture of a soap and a particular SE with or without a saccharide incorporated therein.
• a detergent composition which has a good detergency at relatively low temperatures as well as at relatively high temperatures may comprise a mixture of 75 to 95% by weight of a soap component with 25 to 5% by weight of a sucrose ester component, said sucrose ester component comprising essentially at least one sucrose ester of fatty acid having 12 to 14 carbon atoms and 70% or more by weight of said sucrose ester being monoand di-esters of fatty acid.
• the above mentioned particular SE is incorporated in the above mentioned particular proportions to soap, whereby it has become possible to improve-the detergency at low temperatures such as 30C or less, particularly 20l0C which have been insufficient for domestic detergents.
• low temperatures such as 30C or less, particularly 20l0C which have been insufficient for domestic detergents.
• the resulting detergency is superior to that of synthetic detergents.
• the sucrose ester component may preferably comprise a sucrose ester of a mixed fatty acid.
• the mixed fatty acid may comprise at least 50%, preferably at least by weight of saturated fatty acid having l.2 to 14 carbon atoms and the remaining part of saturated fatty acid having 10 or less carbon atoms, saturated fatty acid having 16 or more carbon atoms and various unsaturated fatty acids.
• the total amount of monoand di-esters in the SE component according to the invention must be or more by weight. In other words, trior higher polyesters must be 30% or less by weight.
• the soap component used in this embodiment may be a member selected from the group consisting of K and Na salts of saturated or unsaturated fatty acids having 8 to 22 carbon atoms.
• the soap component is a member selected from the group consisting of K and Na salts of lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid and mixtures thereof.
• the soap may be a product obtained by saponifying a member selected from the group consisting tallow, coconut oil, cotton seed oil, whale oil,
• palm oil palm kernel oil, soy bean oil and mixtures there of.
• composition ratio of the detergent composition having a good detergency at relatively low temperatures as described in the above is critical.
• the composition should comprise a mixture of 75 to 95%, preferably 80 to 90%, by weight of a soap with 25 to 5%, preferably 10 to by weight of a sucrose ester component.
• the good detergency at relatively low temperatures is only secured within this composition range.
• the optimum composition ratio depends on the nature of the SE to be used. Generally, the amount of SE to be used, within the above mentioned range, is comparatively small when the SE has a high degree of hydrophilicity, while when it has a low degree of hydrophilicity, a comparatively large amount of SE would be required to obtain the desired effect.
• the detergent composition described having a good detergency at relatively low temperatures is ready to use as it is, either in the form of a solid or in the form of powder, but it may be finished into more effective and attractive detergent products by suitably incorporating thereto sodium carbonate, sodium silicate, borax and other alkaline builders, sodium tripolyphosphate, NTA, EDTA, SODA (sodium diglycollate), sodium citrate, sodium polyacrylate and other additives which cooperate with metallic ions to form chelate compounds, fatty acid alkanol amide and other additives which have foam boosting effect, carboxymethyl cellulose, bleaching agents, fluoroescent dyes, etc.
• Some conventional methods of producing SE may result in providing crude reaction product with soap present mixed therein. In these case, it is possible to adjust such product along with soap included therein to the composition of the present invention and then to make industrial use thereof to advantage.
• the sucrose ester component for the above detergent composition may also include a small amount of glyceride.
• the sucrose ester component is a product produced from fats and fatty oils with sucrose, said product including unreacted or by-product glyceride.
• the detergent composition having the above described good detergency at relatively low temperatures as well as at relatively high temperatures may further include a saccharide component. It has been found that the addition of saccharide further improves the detergency at relatively low temperatures and still maintains public hazardlessness. The effect of improving the detergency can only be achieved by adding a saccharide to the mixture of soap with SE. It has been found that the addition of a saccharide to any anionic surfactants (excluding soap) such as ABS or LAS, any non-ionic surfactants other than SE, any amphoionic surfactants, a mixture of any of those surfactants with either SE or soap can never result in improving the detergency at relatively low temperatures.
• saccharides there may be mentioned monosaccharides and disaccharides such as sucrose and solbitol. Decomposed products of those saccharides are also useful.
• the unreacted sucrose Component contained in the crude reaction mixture obtained in the production of SE is useful. This unreacted sucrose component includes decomposed products of sucrose.
• the saccharide component is added so that the resultant composition may comprises 5 to 50% by weight of a saccharide component and 95 to 50% by weight of a mixture of soap with SE.
• the crude reaction mixture may include an unreacted saccharide component including any decomposed product of sucrose.
• Such crude reaction mixture including SE and saccharide can be utilized for preparing the detergent composition according to the invention.
• the present invention further provides a detergent composition making concurrent use of soap and a particular SE to greatly improve the feeling of the wash after washing and finish it soft, while acting on the skin very mildly.
• Such the detergent composition like this may comprise to 97%, preferably, to by weight of a soap and 25 to 3%, preferably 20 to 5%, by weight of a sucrose ester component.
• the sucrose ester component may comprise essentially at least one sucrose ester of fatty acid having 16 or more carbon atoms and the degree of substitution of said sucrose ester given by the average value of the number of esterified fatty acid molecules per one sucrose molecule is within the range of 1.5 to 3.5, preferably, within the range of 1.6 to 2.0.
• the fatty acid for the production of the SE may be either saturated one or unsaturated one.
• the sucrose ester component may comprise a sucrose ester of a mixed fatty acid.
• the mixed fatty acid should comprise at least 50% by weight of fatty acid having 16 or more carbon atoms and the remaining part of other fatty acid.
• the sucrose ester component may further include a small amount of glyceride.
• the sucrose ester component is a product produced from fats and fatty oils with sucrose, said product including unreacted or by-product glyceride.
• the soap component may be a member selected from the group consisting of K and Na salts of saturated or unsaturated fatty acids having 8 to 22 carbon atoms.
• the soap may be a product obtained by saponifying a member selected from the group consisting tallow, coconut oil, cotton seed oil, whale oil, palm oil, palm kernel oil, soy bean oil and mixtures thereof.
• the soap can be prepared by saponifying a mixture of at least 50% by weight of tallow with the remaining part of palm oil, palm kernel oil'and soy bean oil.
• SE consisting of a long-chained fatty acid and having a high degree of substitution, but such SE is little water-soluble or water-insoluble, causing inconvenience in the inherent detergency. According to the invention, however, the impartation of softness and the good detergency can be obtained comparatibly with each other.
• the present inventive detergent composition is the best from the standpoint of the balance between softness impartation to the wash and detergency.
• the respective ranges for the degree of substitution and for the composition ratio are critical. Those values may, however, be varied, within the respective defined ranges, according to the circumstances under which 7 the materials to be washed are placed. For example, for applications where importance is placed on softening effects on the wash such as babies underwear and ladies high-grade garments it would be recommendable to select such SE as having a higher degree of substitution and a relatively large content of SE, whereas where importance is placed on the removal ofsoil, a low degree, of substitution and a lower content of SE would meet such requirement.
• Phosphates such as polyphosphates, inorganic builders such as sodium carbonate and sodium silicate, salts such as of citric acid, malic acid and tartric acid, organic builders such as salts of amino acid, CMC, EDTA, fluorescing agents, and bleaching agents may be incorporated in the present inventive composition.
• inorganic builders such as sodium carbonate and sodium silicate
• salts such as of citric acid, malic acid and tartric acid
• organic builders such as salts of amino acid, CMC, EDTA, fluorescing agents, and bleaching agents
• the incorporation of sodium tripolyphosphate as a builder provides a detergency which stands comparison with known ABS type detergents which have high detergency but have become a problem because of their foam pollution and adverse effects on the human body.
• the present inventive composition unlike the conventional ABS type and AB type detergents, causes no foam pollution and has no adverse effects on the human body. Rather, it is capable of imparting a mild and smooth touch to the skin. In this connection, it has been ascertained that the detergent composition described also prevents metallic soap from being deposited on the washed materials, thereby ensuring that the washed materials may feel very soft. Thus, the present inventive composition alone can also fully play the role of the conventional softening agent.
• the above detergent composition which can improve the feeling ofwash and finish it soft may further include a saccharide component. It has been found that the addition of a saccharide further improves the detergency 3 and still maintaining public hazardlessness.
• a saccharide further improves the detergency 3 and still maintaining public hazardlessness.
• monosaca saccharide component and 95 to 50% by weight of a mixture of soap with SE.
• the crude reaction mixture usually includes an unreacted saccharide component including any decomposed product 'of sucrose.
• Such crude reaction mixture ineluding SE and saccharide can be utilized for preparing the detergent composition according to the invention.
• EXAMPLE 1 Materials to be washed: Seven short sleeve shirts charged by wearing for three days. Bath Ratio: 1 3 Amount of detergent: 40g Amount of water: 30! Temperature of water: 30C Washing time: I minutes Washing machine: electric washing machine on the marked (by Toshiba Ltd. in the trade name Toshiba Ginga") Method of Measuring Detergency:
• the following standard soiled fabrics were sewn to the aforesaid materials to be washed one for each and were washed under the aforesaid washing conditions.
• the soiled fabrics were evaluated in terms of the following percentage detergency, using the average value of the seven fabrics:
• Tallow soap and a mixed SE (tallow SE: coconut SE 7 3; and 4% of monoester, 35% diester and 9% of 60 in various mixing ratios noted in Table 4. They were measured at a concentration of 0.2% and a temperature of 30C for their foaming effect and foam retention by the Rossmilcs method (SK-3362). The results were as shown in Table 4. Further, sucrose and other builders were added to said mixtures as shown in Table 4 and then the mixtures were similarly measured. The results were as shown in Table 4.
• sucrose to a mixed system of soap and SE greatly improves foaming and preserves the stability thereof. Further inorganic and organic builders were incorporated in plate of sucrose, but almost no change was observed Thus, it has been found that the present invention is by no means inferior to the conventional ABS type detergents on the market.
• EXAMPLE 5 Mixtures consisting of by weight of various SEs shown in Table 5 and 90% by weight of tallow soap were measured for their detergency under the following washing conditions and by the following method. The detergency was evaluated in terms of the following percentage detergency. The results were as shown in Table 5. In addition, such measurements were also taken of tallow soap alone and a mixture thereof with a conventional non-ionic surfactant and the results shown in Table 5 were obtained. Washing conditions:
• Washing time l0 minutes Washing machine: Electric washing machine on the market (National Ultra High Speed Uzushio produced by Matsushita Electric Co., Ltd.)
• Standard cotton fabrics for detergency test use were soiled with a mixture of sebum from the human body and natural dust by using the Menken Type fabric soil testing machine.
• the soiled fabrics were sewn to said shirts one for each and washed under said washing conditions.
• the soiled fabrics were evaluated in terms of the following percentage detergency, using the average value of the five fabrics.
• Tallow soap alone 3 Mixture of tallow soap and l0% polyoxyethylene lauryl ether 55 Composition of coconut fatty acid:
• Sucrose coconut fatty acid ester Hi8 Sucrose coconut fatty acid ester Hi8; geney lh obta ned when the mixing ratio between SE (mom. dig "Land higherpolyj and soap is within the range of :95-25:75. Further, it 32.6: 38.0: 29.4)-
• Palm oil map 3 gent temperature [0C 20C 30C sodium metacilicate 8.0% sodium carbonate 25.5% A 78 30 CMC 15% B 78 8] 83 moisture 6.0% C 72 77 79 D so x2 35 r. .15 42 o) ll.
• the Fuainteter values indicate that the higher the value. the more still. or that the lower the value. the softer.
• Constant fatty acid Hydrogenated tallow fatty acid 49.51 mnnoester. 33.7'1 diester and 16.8; tri' and lllgllLFPtllyesleI Degree of substitution: 1.50
• Detergents consisting of the following compositions A-D were used under the following conditions and their detergency and softness impartation properties were tested in the manner similar to that in Example 9.
• Example 10 With the sodium tripolyphosphate in Example 10 being replaced in the same amount by various builders shown in Table 1 1 and with the other conditions and the method of measurement being the same as in Example l0. measurement were taken and the results shown in Table 11 were obtained.
• Soiled fabric Three fabrics artificially soiled with natural dirt
• Method of washing Terg-to-meter sodium tripolyphosphate 78.5 50
• Wash ng concentration 0.2% sodium pyrophosphate 77.0
• Washmg temperature 25C sodium carbonate 67.7 l'lardness of washing sodium metasilicate 65.3 liquid: 30 ppm (as CaCO sodium citrate 52.5 Washing time: 10 min.
• a detergent composition consisting essentially of a mixture of 75 to 97% by weight of a soap with 25 to 3% by weight of a sucrose ester, said sucrose ester comprising at least one sucrose ester of a fatty acid having 12 to 14 carbonatoms and at least 70% by weight of said sucrose ester being mono-and di-esters, the degree of substitution of said sucrose ester given by the average value of the number of esterified fatty and molecules per one sucrose molecule being within the range of 1.5 to 3.5.
• sucrose ester comprises a sucrose ester of a mixed fatty acid, said mixed fatty acid comprising at least 50% by weight of saturated fatty acid having l2 to 14 carbon atoms and the remaining part of saturated fatty acid having or less carbon atoms, saturated fatty acid having 16 or more carbon atoms and various unsaturated fatty acids.
• a detergent composition according to claim 2 in which at least 65% by weight of said fatty acid consists of fatty acid having 12 to 14 carbon atoms.
• a detergent composition consisting essentially of to, 90% by weight of a mixture of a soap with a sucrose ester of fatty acid and 30 to 10% by weight of a saccharide, said mixture of a soap of sucrose ester of fatty acid consisting essentially of to 97% by weight of a soap with 25 to 3% by weight of a sucrose ester of fatty acid having 12 to 14 carbon atoms, at least 70% by weight of said sucrose ester being mono-and diesters, and the degree of substitution of said sucrose ester given by the average value of the number of esterfied fatty acid molecules per sucrose molecule being within the range of 1.5 to 3.5.
• sucrose ester consists essentially of a sucrose ester of a mixed fatty acid, said mixed fatty acid,
• saturated fatty acid having 12 to 14 carbon atoms comprising at least 50% by weight of saturated fatty acid having 12 to 14 carbon atoms and the remaining part of saturated fatty acid having 10 or less carbon atoms, saturated fatty acid having 16 or more carbon atoms and various unsaturated fatty acids.
• a detergent composition according to claim 8 in which said soap is a member selected from the group consisting of K and Na salts of saturated or unsaturated fatty acids having 8 to 22 carbon atoms.
• a detergent composition according to claim 8 in which said saccharide is a member selected from the group consisting of sucrose, sorbitol, decomposed product of sucrose and mixtures thereof.

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• Chemical & Material Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Engineering & Computer Science (AREA)
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• Oil, Petroleum & Natural Gas (AREA)
• Wood Science & Technology (AREA)
• Organic Chemistry (AREA)
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• Emergency Medicine (AREA)
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Cited By (15)

Citations (5)

• 1972
  • 1972-09-07 GB GB4163872A patent/GB1399927A/en not_active Expired
  • 1972-09-08 US US287550A patent/US3867301A/en not_active Expired - Lifetime
  • 1972-09-09 DE DE2244310A patent/DE2244310A1/de active Granted

Patent Citations (5)

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