US2081407A - Drier - Google Patents
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- US2081407A US2081407A US2081407DA US2081407A US 2081407 A US2081407 A US 2081407A US 2081407D A US2081407D A US 2081407DA US 2081407 A US2081407 A US 2081407A
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- drier
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- stabilizer
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- 239000003381 stabilizer Substances 0.000 description 66
- 239000000243 solution Substances 0.000 description 44
- 239000002253 acid Substances 0.000 description 42
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 30
- 239000003973 paint Substances 0.000 description 30
- 239000001069 triethyl citrate Substances 0.000 description 30
- 235000013769 triethyl citrate Nutrition 0.000 description 30
- ZFOZVQLOBQUTQQ-UHFFFAOYSA-N tributyl 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound CCCCOC(=O)CC(O)(C(=O)OCCCC)CC(=O)OCCCC ZFOZVQLOBQUTQQ-UHFFFAOYSA-N 0.000 description 26
- 229910052751 metal Inorganic materials 0.000 description 24
- 239000002184 metal Substances 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 20
- 210000003298 Dental Enamel Anatomy 0.000 description 18
- 150000007513 acids Chemical class 0.000 description 18
- 239000002966 varnish Substances 0.000 description 18
- 150000001298 alcohols Chemical class 0.000 description 16
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 16
- 229910052803 cobalt Inorganic materials 0.000 description 16
- 239000010941 cobalt Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000003981 vehicle Substances 0.000 description 14
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 12
- 238000001035 drying Methods 0.000 description 12
- 229910052500 inorganic mineral Inorganic materials 0.000 description 12
- 239000011707 mineral Substances 0.000 description 12
- 235000010755 mineral Nutrition 0.000 description 12
- 235000015096 spirit Nutrition 0.000 description 12
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 125000005609 naphthenate group Chemical group 0.000 description 10
- 239000000344 soap Substances 0.000 description 10
- IFSWBZCGMGEHLE-UHFFFAOYSA-L cobalt(2+);naphthalene-2-carboxylate Chemical compound [Co+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 IFSWBZCGMGEHLE-UHFFFAOYSA-L 0.000 description 8
- VUSWCWPCANWBFG-UHFFFAOYSA-N cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC=CC1 VUSWCWPCANWBFG-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
- 239000000049 pigment Substances 0.000 description 8
- 235000011121 sodium hydroxide Nutrition 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- BFWHHDQLPCRKOU-UHFFFAOYSA-M hydroxy(naphthalen-2-yl)methanolate;manganese(2+);naphthalene-2-carboxylate Chemical compound [Mn+2].C1=CC=CC2=CC(C([O-])O)=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 BFWHHDQLPCRKOU-UHFFFAOYSA-M 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- PWHULOQIROXLJO-UHFFFAOYSA-N manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 6
- 229910052748 manganese Inorganic materials 0.000 description 6
- 239000011572 manganese Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 230000001264 neutralization Effects 0.000 description 6
- 239000006228 supernatant Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-K 2qpq Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 4
- KTVIXTQDYHMGHF-UHFFFAOYSA-L Cobalt(II) sulfate Chemical compound [Co+2].[O-]S([O-])(=O)=O KTVIXTQDYHMGHF-UHFFFAOYSA-L 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229940120693 copper naphthenate Drugs 0.000 description 4
- 230000001627 detrimental Effects 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- PBDSMEGLJGEMDK-UHFFFAOYSA-L iron(2+);naphthalene-2-carboxylate Chemical compound [Fe+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 PBDSMEGLJGEMDK-UHFFFAOYSA-L 0.000 description 4
- 235000021388 linseed oil Nutrition 0.000 description 4
- 239000000944 linseed oil Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- -1 rosin Chemical class 0.000 description 4
- 239000008149 soap solution Substances 0.000 description 4
- 230000000087 stabilizing Effects 0.000 description 4
- YUTUUOJFXIMELV-UHFFFAOYSA-L 2-hydroxy-2-(2-methoxy-2-oxoethyl)butanedioate Chemical compound COC(=O)CC(O)(C([O-])=O)CC([O-])=O YUTUUOJFXIMELV-UHFFFAOYSA-L 0.000 description 2
- 230000036880 Cls Effects 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L Copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- 240000002989 Euphorbia neriifolia Species 0.000 description 2
- OYHQOLUKZRVURQ-UHFFFAOYSA-N Linoleic acid Chemical compound CCCCCC=CCC=CCCCCCCCC(O)=O OYHQOLUKZRVURQ-UHFFFAOYSA-N 0.000 description 2
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 230000003197 catalytic Effects 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 229940044175 cobalt sulfate Drugs 0.000 description 2
- 229910000361 cobalt sulfate Inorganic materials 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 229940049918 linoleate Drugs 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 229940099596 manganese sulfate Drugs 0.000 description 2
- 239000011702 manganese sulphate Substances 0.000 description 2
- 235000007079 manganese sulphate Nutrition 0.000 description 2
- ISPYRSDWRDQNSW-UHFFFAOYSA-L manganese(II) sulfate monohydrate Chemical compound O.[Mn+2].[O-]S([O-])(=O)=O ISPYRSDWRDQNSW-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000003340 mental Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; DRIERS (SICCATIVES); TURPENTINE
- C09F9/00—Compounds to be used as driers (siccatives)
Definitions
- This invention is a drier and more particularly one adapted to be used in connection with the.
- the metal contained in the driers should be of the highest degreeof availability of use.
- the drier should have a minimum eifect upon the viscosity, flow, color and stability of the clear or pigmented vehicle in which it is incorporated.
- the drier should exhibit no adverse action upon the durability of thecoating in which it is incorporated.
- - -Th'e drier should not detrimentally affect the color retention properties of the vehicle in which it is used.
- the drier shouldbe non-reactive with the pig- -ment portion of paints, varnishes and enamels.
- the drier should retain its clarity and homogeneity even when exposed toair.
- a cobalt drier should be as blue as possible in '5 order'to effect some bleaching action upon the vehicle in which it is used.
- a manganese drier should be as pale as possible-so as to cause minimum discoloration in paints, varnishes andenamels inwhich it is ino corporated. f-
- Driers containing free acids exert at times very appreciable amount of free acid will not dry as v pronounced effects upon the physical characteristics of paints, varnishes and enamels causing increase in the viscosity of the paint and impairing the flowing qualities thereof.
- metal driers of the character described may be very appreciably improved and in some casesmade practically'ideal through the employment of a stabilizing agent which is non-volatile, neutral, substantially water-insoluble and non-reactive-with the vehicle or pigments in which the drier is to be used and which has no noticeable effect upon the viscosity of the paint to which they may. be added.
- a stabilizing agent which is non-volatile, neutral, substantially water-insoluble and non-reactive-with the vehicle or pigments in which the drier is to be used and which has no noticeable effect upon the viscosity of the paint to which they may. be added.
- stabilizers having the properties of triethyl citrate, tributyl citrate, cyclo-hexyl-paratoluenesulfanamid particularly when employedin connection with naphthenate metal driers.
- These specified stabilizers materially increase the solubflity of the cobalt naphthenate in the mineral spirits and materially promote solubility in the combination and produce that permanent solubility so essential to an ideal drier. They are non-volatile and neutral and thus will notvolatilize off from the finished dried during storage,
- the supernatant liquid carrying a drier was decanted oil? and yielded 1,000 pounds of 6% cobalt naphthenate solutioncontaining approximately 1% of stabilizer.
- the above procedure may be carried out at room temperature, but can be speeded up at slightly elevated temperatures.
- Example No.3 A similar procedure may be carried out using approximately '27 poundsof the tributyl citrate in" place of the 9 pounds of cyclo-hexyl-para toluehe-sulfanamid- Example No. 4
- a 6% manganese naphthenate solution containing triethyl citrate as stabilizer was prepared by adding to 450 pounds of naphthenic acid 28 pounds of triethyl citrate with good agitation.
- a 6% iron naphthenate solution. containing tributyl citrate'as stabilizer was prepared by adding to 488 pounds of a suitable naphthenic acid 30 pounds of tributyl citrate. This was done under thorough agitation. To this was added under agitation 97 pounds of flake caustic soda dissolved in 400 pounds of water. To the resultant alkali ify and it was found that such stratification occurred promptly and was'sharply defined. The supernatant liquid was found to yield 1,000 pounds of a 6% iron naphthenate solution containing approximately 3% of stabilizer.
- Example No. 7 I A 6% solution of copper naphthenate containing triethyl citrate as stabilizer was prepared by adding 30 poundsof triethyl citrate to 421 pounds forth practical methods of producing metal naph- 'in 400 pounds of water.
- driers which have thus far been driers, carrying volatile. solvents, these solvents may be driven off in any appropriate way to yield driers in solid form, or, if desired, paste driers may be produced by leaving some of'the solvent in the drier or by adding any appropriate vehicle as will be well understood.
- Driers made in the manner hereinbefore described are superior to driers heretofore used in.
- methyl citrate and cyclo-hexyl-paratoluene sulfanamid stabilizers of this-invention are practically insoluble in petroleum hydrocarbons and more particularly mineral spirits which are, commonly used as a solvent or diluent for driers and for paints,
- varnishes and enamels in which they are incorof triethyl citrate, tributyl citrate and cyclohexyl-paratoluene-sulfanarnid.
- a drier comprising cobalt naphthenate and an organic alcohol derivative stabilizer selected from the group which consists of triethyl citrate, tributyl citrate and cyclo-hexyl-parato1uene-sulfanamid.
- a drier comprising a water-insoluble manganese soap and an organic alcohol derivative stabilizer selected from the group which consists of triethyl citrate, tributyl citrate and cyclohexyl-paratoluene-sulfanamid.
- a drie'r comprising a metal naphthenate dissolved in an organic thinner and which solution contains an organic alcohol derivative stabilizer selected from the group which "consists of triethyl citrate, tributyl "citrate and cyclo-hexylparatoluene-sulfanamid.
- a drier comprising cobalt naphthenate dissolved in an organicthinner and which solution contains an organic alcohol derivative stabilizer selected from the group which consists oi triethyl citrate, tributyl citrate and cyclo-hexylparato'luene-s'ulfanamid.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
Description
Patented May 1937 UNITED STATES. PATENT OFFICE Arthur Minich, Newark, N. J., assignor to Nuodex Products 00., Inc., a corporation of New York N6 Drawing. Application April so, 1936.
- Serial No. 77,141
11 Claims. (Cl. 134-57) This invention is a drier and more particularly one adapted to be used in connection with the.
drying of paints, varnishes and enamels and especially of the character which embodies one or more drying metals, such as cobalt, manganese,
iron, and the like, inthe form of naphthenates, linoleates and the like. 1
My experience and research have convinced me that the ideal drier should possess the following 1 prerequisites:
It should remain in perfect solution for an indefinite period of storage.
.The metal contained in the driers should be of the highest degreeof availability of use.
15 The drier should have a minimum eifect upon the viscosity, flow, color and stability of the clear or pigmented vehicle in which it is incorporated. The drier should exhibit no adverse action upon the durability of thecoating in which it is incorporated.- -Th'e drier should not detrimentally affect the color retention properties of the vehicle in which it is used. The driershouldbe non-reactive with the pig- -ment portion of paints, varnishes and enamels.
The drier should retain its clarity and homogeneity even when exposed toair.
It should be in such concentrated form as to render it economical from the manufacturers and shippers standpoint. For example, it is found practical in cobalt ormanganese drier to utilize metal concentrations in the neighborhood of from 4% to 6%. r
A cobalt drier should be as blue as possible in '5 order'to effect some bleaching action upon the vehicle in which it is used.
. A manganese drier should be as pale as possible-so as to cause minimum discoloration in paints, varnishes andenamels inwhich it is ino corporated. f-
One of the most important of the foregoing prerequisites of the ideal'drier is that of stability. for, unless the drier is stable, it is open to serious disadvantages. For example, it may precipig recognized that a drier to be commercially practical must, when incorporating most of the drying metals, embody also an appropriate stabilizer and this has been recognized for years and there has grown up in the trade the accepted usage of acids for this purpose, it having been found that excess free acid when incorporated in the drier has a stabilizing function. It may be noted in this connection that common practice has dictated, for this purpose, amounts of acid varying from 2% to as high as based on the total.
weight of the solution. While a relatively large number of acids have been used for this purpose, the more commonly employed are naphthenic i acids, linseed oil fatty acids, benzoic acid, rosin,
etc. Experience has shown; however, that the inclusion of any of these acids as a stabilizing agent in driers introduces a number of serious disadvantages and these disadvantages are fairly well understood in the paint, varnish and enamel business. Those which are outstanding may be briefly enumerated as follows:
- The presence of free acid does not'asa matter of fact always guarantee permanent stability of the drier solutions. This is particularly true of rosin which, even in higher percentages, will not -perm-anently prevent gellation of a cobalt drier.
The presence of free acids, such as rosin, in
a drier, and thus ultimately in paint, varnish and The addition of sufficient free acid to be em.
tive as a stabilizer in a cobalt drier tends to r change the color of the latter fromblue to red I which is undesirable from a technical as well as a sales standpoint.
The presence of free acids, such as benzoic acid,- tends to make the drying performance of the metal uncertain.
Free acid such-as benzoic acidsa'r'e oiften' highly reactive with some of the pigments contained in paint and enamel and such an interaction tends to set up a decided increase in the body of the paint or enamel and ten'cls to impair the tone of some pigments, such as delicate maroon colors.
Under some conditions a drier-containing an efficiently with with acid as it would without.
Driers containing free acids exert at times very appreciable amount of free acid will not dry as v pronounced effects upon the physical characteristics of paints, varnishes and enamels causing increase in the viscosity of the paint and impairing the flowing qualities thereof.
The presence of some free acids, such'as linseed oil fatty acids, in driers and in the paint vehicle aggravate any tendency of the coating material to after-yellow which is especially no ticeable and objectionable in the case of white coatings.
As hereinbefore stated, many of thedisadvan tages to which'referencehas'been made have been recognized in the industry and much research has been madein an attempt to solve these problems. For example, it has been suggested touse butyl alcohol as a stabilizing agent in place of an acid stabilizer and such butyl alcohol has been employed to some extent. How-' ever, while it solves certain of the problems inherent in the use of acid, it introduces certain other problems which are even more serious in some respects.
Y highly volatile and the drier must be used almost immediately to obtain any'satisfaetory results.
If left uncovered it evaporates very rapidly and the stabilizing action is correspondingly de-' creased. It may also be noted that butyl alcohol and other volatile-stabilizers have a decided effect upon the viscosity of the paint, varnishor enamel vehicles and this too isundesirable. Experience has definitely shown that it is a practical impossibility to obtain uniform stabilizers with butyl alcohol for obvious reasons.
With the foregoing considerations in mind, it will be clear that a very definite need existed in the industry for a concentrated drier which will embody the ideal conditions to which I have referred and without the detrimental, features ad-' verted to. The object of the present invention was to produce such a drier.
I have found that metal driers of the character described may be very appreciably improved and in some casesmade practically'ideal through the employment of a stabilizing agent which is non-volatile, neutral, substantially water-insoluble and non-reactive-with the vehicle or pigments in which the drier is to be used and which has no noticeable effect upon the viscosity of the paint to which they may. be added. 'For example, I have obtained very satisfactory results with stabilizers having the properties of triethyl citrate, tributyl citrate, cyclo-hexyl-paratoluenesulfanamid particularly when employedin connection with naphthenate metal driers. These specified stabilizers materially increase the solubflity of the cobalt naphthenate in the mineral spirits and materially promote solubility in the combination and produce that permanent solubility so essential to an ideal drier. They are non-volatile and neutral and thus will notvolatilize off from the finished dried during storage,
and that attendant reaction which is so detri-" mental in acid stabilizers is entirely absent-in the stabilizers to which I have referred.
l The amount of stabilizer'needed is so small as not to affect the physical properties of. the paints, varnishes or enamels and a drier carrying from 4% to 6% cobalt, for example,-has been found stable and eflicient over long periods of time.
Other features and advantages of-the invention will hereinafter appear in connection with the following illustrative examples showing how For example, butyl alcohol is drlers embodying this invention have been practically produced.
' Example No. 1 Y To 440 pounds, of a suitable naphthenic acid there was added 9 pounds of cyclo-hexyl-paratoluene-sulfanamid. This was done with accom-. panying agitation. To this was added, with accompanying agitation, a solution carrying 88 pounds of flake-"caustic soda dissolved inv 400 pounds of water. To the resulting alkali-soap solution was added464 pounds of mineral spirits under thorough agitation. While the agitation was continued, there was finally introduced a solution of 295 pounds cobalt sulfate crystals in 400 pounds of water. The mixture was thereupon allowed to stratify and it was found that such- I stratification occurred promptly and was sharply defined. The supernatant liquid carrying a drier was decanted oil? and yielded 1,000 pounds of 6% cobalt naphthenate solutioncontaining approximately 1% of stabilizer. The above procedure may be carried out at room temperature, but can be speeded up at slightly elevated temperatures.
In lieu of the stratification and subsequent decantation referred to, it has beenfound thor oughly practical to mechanically separate in any appropriate way as by centrifuging.
Example No. 2
A similar procedure may be carried outusing approximately 27 pounds of the triethyl citrate in place of the 9 pounds of cyclo-hexyl-paratoluene- 'sulfanamid. I
- Example No.3 y A similar procedure may be carried out using approximately '27 poundsof the tributyl citrate in" place of the 9 pounds of cyclo-hexyl-para toluehe-sulfanamid- Example No. 4
A 6% manganese naphthenate solution containing triethyl citrate as stabilizer was prepared by adding to 450 pounds of naphthenic acid 28 pounds of triethyl citrate with good agitation.
Then a solution of 90% pounds of caustic soda in 400 pounds of water was introduced under continuedagitation. To the thus obtained alkalisoap-solution was added 487 pounds of mineral spirits and finallyQwhile agitation was continued,
a solution of 217 pounds manganese sulfate in 400 pounds of water was introduced. The resulting solution was found to stratify rapidly and completely and .was mechanically separated and it was found that theyield was approximately l,000 pounds of 6% manganese naphthenate drier containing 2.8% of the stabilizer. The use of moderate heats will speed upthe operation. It is also possible to operate with more-than one stabilizen'as will be apparent from the following example.
I Example No. 5 y
' enumerated in the examples given areliqu id Example No. a s
A 6% iron naphthenate solution. containing tributyl citrate'as stabilizer was prepared by adding to 488 pounds of a suitable naphthenic acid 30 pounds of tributyl citrate. This was done under thorough agitation. To this was added under agitation 97 pounds of flake caustic soda dissolved in 400 pounds of water. To the resultant alkali ify and it was found that such stratification occurred promptly and was'sharply defined. The supernatant liquid was found to yield 1,000 pounds of a 6% iron naphthenate solution containing approximately 3% of stabilizer.
I Example No. 7 I A 6% solution of copper naphthenate containing triethyl citrate as stabilizer was prepared by adding 30 poundsof triethyl citrate to 421 pounds forth practical methods of producing metal naph- 'in 400 pounds of water.
of a suitable naphthenic acid .with good agitation. Then a solution of 84 pounds of flake caustic soda in 400 pounds of water was added with thorough stirring. To the thus obtained alkali soap solution was 'added 481 pounds of mineral spirits and finally, while agitation was continued, a solution of 245 pounds of copper sulphate I The resultant solution was found to stratify rapidly and was mechanically separated and it: was found that theyield was approximately 1,000 pounds of 6% copper naphthenate solution containing 3% of stabilizer.
In all of the foregoing examples, I have set thenateswith stabilizers of the character under consideration through theprocess of. double decomposition. This process gives highly satisfactory results, but is not the only procedure, which may be followed. 0n the contrary, it is entirely feasible to-use any well known procedureknown to the art for the making of naphthenate driers of the kind herein under consideration, but the stabilizer or stabilizers to be employed should be incorporated into the drier by incorporation into the acid or into the acid mineral spirits solution before proceeding with the necessary chemical reactions which are involved in the production of metallic driers. I 7
Furthermore the foregoing examples deal with the making of metal naphthenate driers, but the invention may be carried out in the production of metallic driers of other acids of which the following may be referred to by way of example.
Example No. 8.
' 198 pounds of cobalt sulphate dissolved in 300 poundsof water. 'Iheresultingreaction mixture was allowed to separate and it was found that.
such stratification occurred promptly and was sharply defined. The supernatant liquid carrying a drier was decanted off and yielded approxi mately 1,000 pounds of a 4% cobalt linoleate solution containing 2% of stabilizer. 2
While the driers which have thus far been driers, carrying volatile. solvents, these solvents may be driven off in any appropriate way to yield driers in solid form, or, if desired, paste driers may be produced by leaving some of'the solvent in the drier or by adding any appropriate vehicle as will be well understood.
Driers made in the manner hereinbefore described are superior to driers heretofore used in.
the art. They are efficient, economical and uniform in their operation. They are permanent in character. They act expressly and solely as catalytic drying agents upon paint, varnish and enamelvehicles in which they are incorporated and exert no detrimental influence thereon.
Reference is made to the fact that the methyl citrate and cyclo-hexyl-paratoluene sulfanamid stabilizers of this-invention are practically insoluble in petroleum hydrocarbons and more particularly mineral spirits which are, commonly used as a solvent or diluent for driers and for paints,
" varnishes and enamels in which they are incorof triethyl citrate, tributyl citrate and cyclohexyl-paratoluene-sulfanarnid.
2. A drier comprising cobalt naphthenate and an organic alcohol derivative stabilizer selected from the group which consists of triethyl citrate, tributyl citrate and cyclo-hexyl-parato1uene-sulfanamid.
' 3. A drier comprising a water-insoluble manganese soap and an organic alcohol derivative stabilizer selected from the group which consists of triethyl citrate, tributyl citrate and cyclohexyl-paratoluene-sulfanamid. I
4; A drier comprising a water-insoluble iron soap and an organic alcohol derivative stabilizer selected from the group which consists of triethyl citrate, tributyl citrate and cyclo-hexyl-paratoluene-sulfanamid.
5. A drier comprising a water-insoluble soap of a drying metal dissolved in an organic thinner which solution-contains an organic alcohol derivative stabilizer selected from the group which consists of triethyl citrate, tributyl citrate and cyclo-hexyl paratoluene-sulfanamid.
6. A drier comprising a neutral, water-insoluble soap of a drying metal dissolved in an organic thinner which solution contains an organic alcohol derivative stabilizer selected from the group which consists of triethyl citrate, tributyl citrate and cyclo-hexyl-paratdluene-sulfanamid.
7. A drie'r comprising a metal naphthenate dissolved in an organic thinner and which solution contains an organic alcohol derivative stabilizer selected from the group which "consists of triethyl citrate, tributyl "citrate and cyclo-hexylparatoluene-sulfanamid.
8. A drier comprising cobalt naphthenate dissolved in an organicthinner and which solution contains an organic alcohol derivative stabilizer selected from the group which consists oi triethyl citrate, tributyl citrate and cyclo-hexylparato'luene-s'ulfanamid.
'9. A drier comprising manganese naphthenate dissolved in an organic thinner and which soluethyl citrate, tributyl citrate and cyclo-hexyiparatoluene-sulfanamid.
11. A drier comprising a water-insoluble cobalt soap and an organic alcohol derivative stabilizer selected from the group which consists of triethyl citrate, tributyl citrate, and cycio-hexylparatoluene-suli'anamid.
' ARTHUR MINICH.
Publications (1)
Publication Number | Publication Date |
---|---|
US2081407A true US2081407A (en) | 1937-05-25 |
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ID=3428717
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US2081407D Expired - Lifetime US2081407A (en) | Drier |
Country Status (1)
Country | Link |
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US (1) | US2081407A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2531460A (en) * | 1950-11-28 | Stabilized metallic soaps | ||
US2747979A (en) * | 1952-11-14 | 1956-05-29 | Eastman Kodak Co | Mono-esters of citric acid as metal deactivators for motor fuels |
US2785989A (en) * | 1954-03-29 | 1957-03-19 | American Cyanamid Co | Metallic soaps of fatty acids and polyhydroxy monocarboxylic acids |
US2793132A (en) * | 1954-03-29 | 1957-05-21 | American Cyanamid Co | Metallic soaps of fatty acids and alphahydroxy alkanoic acids |
-
0
- US US2081407D patent/US2081407A/en not_active Expired - Lifetime
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2531460A (en) * | 1950-11-28 | Stabilized metallic soaps | ||
US2747979A (en) * | 1952-11-14 | 1956-05-29 | Eastman Kodak Co | Mono-esters of citric acid as metal deactivators for motor fuels |
US2785989A (en) * | 1954-03-29 | 1957-03-19 | American Cyanamid Co | Metallic soaps of fatty acids and polyhydroxy monocarboxylic acids |
US2793132A (en) * | 1954-03-29 | 1957-05-21 | American Cyanamid Co | Metallic soaps of fatty acids and alphahydroxy alkanoic acids |
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