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US2664408A - Urea and/or thiourea-aldehyde-sulfite waste liquor condensation product - Google Patents

Urea and/or thiourea-aldehyde-sulfite waste liquor condensation product Download PDF

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Publication number
US2664408A
US2664408A US143822A US14382250A US2664408A US 2664408 A US2664408 A US 2664408A US 143822 A US143822 A US 143822A US 14382250 A US14382250 A US 14382250A US 2664408 A US2664408 A US 2664408A
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Prior art keywords
urea
thiourea
waste liquor
aldehyde
sulfite pulp
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US143822A
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Ralph E Plump
James W Carroll
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Pennsylvania Salt Manufacturing Co
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Pennsylvania Salt Manufacturing Co
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Priority to US143822A priority Critical patent/US2664408A/en
Priority to US349952A priority patent/US2823184A/en
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    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
    • C23G1/00—Cleaning or pickling metallic material with solutions or molten salts
    • C23G1/02—Cleaning or pickling metallic material with solutions or molten salts with acid solutions
    • C23G1/04—Cleaning or pickling metallic material with solutions or molten salts with acid solutions using inhibitors
    • C23G1/06—Cleaning or pickling metallic material with solutions or molten salts with acid solutions using inhibitors organic inhibitors
    • C23G1/065—Cleaning or pickling metallic material with solutions or molten salts with acid solutions using inhibitors organic inhibitors sulfur-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
    • C08G12/10—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds with acyclic compounds having the moiety X=C(—N<)2 in which X is O, S or —N
    • C08G12/12—Ureas; Thioureas

Definitions

  • This invention relates to metal pickling and to new compositions particularly useful in this field, the present application being a continuation in part of application No. 645,235, filed February 2, 1946, and now abandoned.
  • the surprisingly superior inhibiting properties of the products obtained may be attributed in part to a reaction in addition to the expected condensation of urea or thiourea with aldehyde, namely a chemical reaction between at least some of the constituents of the sulfite pulp waste liquor and one or more of the other constituents.
  • I'he composition of sulfite pulp waste liquor varies somewhat with the source and treatment, but usually consists of some inorganic materials such as calcium sulfate, calcium oxide and water, thio acids, other acids, chiefly lignosulfonic acid and their calcium salts, lignin, dextrose, mannose, gums, albumins, resins, vanillin and fermentable sugars. Of these the more important constituents are believed to be lignosulfonic acid, lignin, dextrose, mannose and vanillin. Whatever the explanation, we have found the product of the above described reaction is markedly superior in metal pickling inhibiting properties to a mixture of the components, considered individually or in any combination thereof, e. g.
  • urea-formaldehyde-sulfite waste liquor product made according to our invention gave almost 50% increased metal protection as compared to equivalent quantities of a mixture of sulfite pulp waste and a urea-formaldehyde condensation product. Excellent results are achieved on metals such as various types of steels, iron, stainless steel, tinned steel, tinned copper, and tin.
  • our new condensation product in a pickling bath of thetype customarily employed for cleaning metal objects, usually an aqueous solution containing from 1 to 50% by weight of a relatively strong nonoxidizing inorganic acid such as sulfuric, phosphoric, hydrochloric or hydrofluoric acid, preferably in 5-20% by weight sulfuric acid or 5-30% hydrochloric acid.
  • a relatively strong nonoxidizing inorganic acid such as sulfuric, phosphoric, hydrochloric or hydrofluoric acid
  • beneficial results may be achieved by incorporating our condensation product in aqueous mixtures of these and other acids.
  • our new product may advantageously be admixed with other materials known to aid or exhibit inhibiting properties; for example, glue,
  • sodium chloride and diphenylthiourea may be admixed therewith.
  • urea, thiourea we mix urea, thiourea, or both, with sulfite pulp waste liquor and a watersoluble aldehyde in an acid reaction medium;
  • urea and/or thiourea may be dissolved in water and the other two reactants added thereto.
  • the resulting mixture may then be acidified and the precipitate which forms separated and dried.
  • the sulfite pulp waste liquor used should preferably not contain more than 30 grams llgnone (i. e. 15 grams of the total solids of the waste liquor) per 15 grams urea, thiourea or mixtures of urea and thiourea employed i.
  • ENUVI l H ER Variation of sulfite pulp waste liquor "(tigno'nm concentration HCl catalyst Thio- Forme- Lig- Weight Percent urea, lin, none, yield, protec-. grams grams grams grams percent 'tion "The product, prepared according to our invention, is incorporated in a typical acid pickling bath, either alone or'in conjunction with other materials which are known to exhibit inhibiting properties. A comparatively low concentration of 'our inhibitor is sufiicient to obtain good metal protection. The concentration required to achieve a certain amount of metal protection will vary with the pickling conditions, but the quantity required'is significantly lower than that of heretofore known inhibiting materials.
  • the product so obtained is superior in inhibiting properties to those of the prior art, and may be admixed with other materials'of inhibiting value,-such as diphenylthiourea, glue, etc.
  • TO-obtain a preferred "product we 'admix: 45%of our condensation product prepared as described above.
  • the condensation reaction product will have superior acid inhibiting properties as long as a water-soluble aldehyde, having less than two functional groups other than the aldehyde group is used, the aldehyde to urea and/or thiourea ratio of the reaction mixture is maintained to within 0.1 to 5 mols aldehyde per mol of urea and/or thiourea, and the concentration of the sulfite pulp waste liquor does not exceed 30 grams Lignone, or 15 grams solid waste liquor, per 15 grams of urea and/or thiourea employed.
  • Example 2 which gives some of the reaction ratios employed, helps further to illustrate the wide range of urea and/or thiourea reactants to aldehyde reactants that can be employed while practicing our invention.
  • the Lignone can be varied, as illustrated in Example 1, for-each ratio of urea and/or thiourea to aldehyde given in Example 2.
  • the amount of urea and thiourea reactants of Example -1 has been kept constant whereas the amount of Lumblee present in the reactants of Example 2 has been kept constant.
  • the resulting product of each of the reaction ratios given in Example 2 was found on testing to be an excellent acid inhibitor. The tests were carried out in the same manner as described ior Example 1.
  • a new composition of matter comprising the condensation product resulting from an acidified reaction mixture of sulfite pulp waste liquor, water-soluble aldehyde, urea and thiourea in which reaction mixture 0.1 to 5 mols of aldehyde are present per mol of combined urea and thiourea and said sulfite pulp waste liquor contains no more than 1 gram of sulfite pulp waste liquor solids per gram of combined urea and thiourea.
  • a new composition of matter comprising the condensation product resulting from an acidified reaction mixture of sulfite pulp waste liquor,-
  • a new composition of matter comprising the condensation product resulting from an acidified reaction mixture of sulfite pulp waste liquor, water-soluble aldehyde, and thiourea in which reaction mixture 0.1 to 5 mols of aldehyde are present per mol of thiourea and said sulfite pulp waste liquor contains no more than 1 gram of sulfite pulp waste liquor solids per gram or thiourea.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Paper (AREA)

Description

Patented Dec. 29, 1953 ac-S REFERENCE UREA AND/OR THIOUREA-ALDEHYDE-SUL- FITE WASTE LIQUOR CONDENSATION PRODUCT Ralph E. Plump, Pittsfield, Mass., and James W. Carroll, Lafayette Hill, Pa., assignors to The Pennsylvania Salt Manufacturing Company, Philadelphia, Pa., a corporation of Pennsylvania No Drawing. Application February 11, 1950,
- Serial No. 143,822
3 Claims. (Cl. 26017.5)
This invention relates to metal pickling and to new compositions particularly useful in this field, the present application being a continuation in part of application No. 645,235, filed February 2, 1946, and now abandoned.
In the pickling of metals, i. e. removal of scale or other metal oxidation products from metal surfaces, it is customary to treat the metal with a dilute aqueous solution of a relatively strong acid such as sulfuric or hydrochloric acid. In prior art practices, a compound or cgmpounds which exhibit inhibiting pro erties are usually incorpora mflmgiigfidin an effort to lessen the attack on the metal. For example, various w lla? PXpi DMLdQKQIlLEiEflLQQwna-lso: l 1 o1ic still residuesxarnmatiathionreaderblaiiyes, d. sifti nmmdrsiso c arywhiwmas and an aldehyde baxelqe a ediahareinbihie ingproperties. It has also been suggested heretofore that the addition of such materials as cellulose pulp waste liquor and gelatin may increase the efliciencies of some pickling baths.
We have now discovered that the solid condensation products obtained by reacting urea, thiourea, or a mixture of urea and thiourea with a mixture of acidified sulfite pulp waste liquor and a water-soluble aldehyde in the presence of an acid catalyst exhibit markedly improved in hibiting properties against metal attack by acid pickling baths ggntainingnon-oxidizing aci s as compared to prior art products.
Though we do not wish to be limited by any theoretical explanation, it is believed that the surprisingly superior inhibiting properties of the products obtained may be attributed in part to a reaction in addition to the expected condensation of urea or thiourea with aldehyde, namely a chemical reaction between at least some of the constituents of the sulfite pulp waste liquor and one or more of the other constituents. I'he composition of sulfite pulp waste liquor varies somewhat with the source and treatment, but usually consists of some inorganic materials such as calcium sulfate, calcium oxide and water, thio acids, other acids, chiefly lignosulfonic acid and their calcium salts, lignin, dextrose, mannose, gums, albumins, resins, vanillin and fermentable sugars. Of these the more important constituents are believed to be lignosulfonic acid, lignin, dextrose, mannose and vanillin. Whatever the explanation, we have found the product of the above described reaction is markedly superior in metal pickling inhibiting properties to a mixture of the components, considered individually or in any combination thereof, e. g. a mixture of ureaof thiourea-aldehyde condensation product and sulfite pulp waste liquor. Thus, in a typical instance, we found that a urea-formaldehyde-sulfite waste liquor product made according to our invention gave almost 50% increased metal protection as compared to equivalent quantities of a mixture of sulfite pulp waste and a urea-formaldehyde condensation product. Excellent results are achieved on metals such as various types of steels, iron, stainless steel, tinned steel, tinned copper, and tin.
In general, we incorporate our new condensation product in a pickling bath of thetype customarily employed for cleaning metal objects, usually an aqueous solution containing from 1 to 50% by weight of a relatively strong nonoxidizing inorganic acid such as sulfuric, phosphoric, hydrochloric or hydrofluoric acid, preferably in 5-20% by weight sulfuric acid or 5-30% hydrochloric acid. In some instances beneficial results may be achieved by incorporating our condensation product in aqueous mixtures of these and other acids. Furthermore, we have found that our new product may advantageously be admixed with other materials known to aid or exhibit inhibiting properties; for example, glue,
sodium chloride and diphenylthiourea may be admixed therewith.
As illustrative of a method of preparing our condensation product, we mix urea, thiourea, or both, with sulfite pulp waste liquor and a watersoluble aldehyde in an acid reaction medium; Thus, urea and/or thiourea may be dissolved in water and the other two reactants added thereto. The resulting mixture may then be acidified and the precipitate which forms separated and dried. In preparing the condensation products of our present invention the sulfite pulp waste liquor used should preferably not contain more than 30 grams llgnone (i. e. 15 grams of the total solids of the waste liquor) per 15 grams urea, thiourea or mixtures of urea and thiourea employed i. e., more than 1 gram total solids of sulfite pulp waste liquor per gram urea, thiourea or mixtures thereof. If higher concentrations are used, the acid inhibiting properties of the resulting product are found to be unsatisfactory. We have obtained the best results by using, in the condensation reaction, sulfite pulp waste liquor concentrations of about 2.5 grams lignone (1.25 grams solid waste liquor) per 15 grams of urea and/or thiourea. However, considerably lower concentrations of the sulfite pulp waste liquor can be employed, excellent acid inhibiting materials being obtained when concentrations as low as 0.5
ENUVI l H ER Variation of sulfite pulp waste liquor "(tigno'nm concentration HCl catalyst Thio- Forme- Lig- Weight Percent urea, lin, none, yield, protec-. grams grams grams grams percent 'tion "The product, prepared according to our invention, is incorporated in a typical acid pickling bath, either alone or'in conjunction with other materials which are known to exhibit inhibiting properties. A comparatively low concentration of 'our inhibitor is sufiicient to obtain good metal protection. The concentration required to achieve a certain amount of metal protection will vary with the pickling conditions, but the quantity required'is significantly lower than that of heretofore known inhibiting materials. Thus, we have found that a concentration, in acid baths of 5 to 10% acid, or as little as 0.001% by weight is effectiveunder usual pickling conditions while about 0.025% by weight is the usual preferred concentration, and 0.10% is the usual maximum "amount'nec'es'sary, though more may be used, 7 being about the maximum amount which will dissolve in the acid pickling'bath.
To illustrateour method of preparation by a "specific example, we may dissolve "60 parts of urea and 6 parts of thiourea in 89 parts of water. 89 parts of sulfite pulp waste liquor (containirig about 12% solids) and 89 parts of 37% formaldehydeare added and the solution stirred. Alternatively, a concentrated sulfite pulp waste liquor may be used with a corresponding addition of water. 15 parts of hydrochloric acid are added with stirring. A precipitate soon forms which may be separated and washed with water, followed by oven drying at 100 C. The product so obtained is superior in inhibiting properties to those of the prior art, and may be admixed with other materials'of inhibiting value,-such as diphenylthiourea, glue, etc. TO-obtain a preferred "product we 'admix: 45%of our condensation product prepared as described above.
9%. e 19% sodium chloride.
7 15 'diphenylthiourea.
found that the condensation reaction product will have superior acid inhibiting properties as long as a water-soluble aldehyde, having less than two functional groups other than the aldehyde group is used, the aldehyde to urea and/or thiourea ratio of the reaction mixture is maintained to within 0.1 to 5 mols aldehyde per mol of urea and/or thiourea, and the concentration of the sulfite pulp waste liquor does not exceed 30 grams Lignone, or 15 grams solid waste liquor, per 15 grams of urea and/or thiourea employed. The table of Example 2, which gives some of the reaction ratios employed, helps further to illustrate the wide range of urea and/or thiourea reactants to aldehyde reactants that can be employed while practicing our invention. In studying this table, it should be kept in mind that the Lignone can be varied, as illustrated in Example 1, for-each ratio of urea and/or thiourea to aldehyde given in Example 2. However, for ease of illustration, the amount of urea and thiourea reactants of Example -1 has been kept constant whereas the amount of Lignone present in the reactants of Example 2 has been kept constant. The resulting product of each of the reaction ratios given in Example 2 was found on testing to be an excellent acid inhibitor. The tests were carried out in the same manner as described ior Example 1.
EXAMPLE 2 T Li no e.
' grams Urea and'thiouremmols Aldehyde, mols 0. 5 formaldehyde 0.1 formaldehyde l benzaldehyde 5 butyraldehyde 0. 33 butyraldehyde. 1 formaldehyde 5 formaldehyde 0. 125 formaldehyde...
In the following examples, which illustrate but do not limit our invention, the composition of the specific example set forth on page 5 was used, and is designated therein simply as the 'inhibitor. The loss in weight of the metal after pickling with and without the presence of the inhibitor gives the percent protectionaccor'ding to the expression:
(Weight loss uniuhibited)(Wcight loss inhibited) mo (Weight loss uninhibited) x These data were obtained by pickling-at various temperatures strips of cold rolled 'steel in' baths of 6% hydrochloric acid containing-the indicated quantities of inhibitor:
Percentprbttion Inhibitor concentration"(welghtpercent) 76. 2 8120 A 79. s -s4.-2 s1, 5 i 87. 4 -84.-8 :96. 4 90. 0 --97. 4
' EXAMPLE 4 These data'were obtained by pickling at 80 C. strips of 'difierent-steels in; bathsof 10% sulfuric acid containing the indicated quantities of inhibitor:
Percent protection at the in- These data were obtained by pickling, at 25 or 50 C. strips of steel in hydrofluoric acid baths containing various quantities of inhibitor:
Percent protection Inhibitor concentration (weight percent) EXAMPLE 6 This example shows the excellent metal protection properties of our products when used in relatively high strength hydrofluoric acid pickling baths, and also demonstrates high stability and long lasting qualities. These data were obtained by pickling, at 24 0., steel strips in a bath of 60% hydrofluoric acid containing 0.50% by weight of our inhibitor for the period of time indicated:
Percent Time hours protection tied asses @0006 Similar pickling operations were carried out employing inhibitor compositions made from urea in the absence of thiourea, from thiourea without urea present, and from mixtures of urea and thiourea other than the above-described mixtures, and marked improvement in metal protection was noted in each case. Similarly, aldehydes other than formaldehyde. e. g. acetaldehyde, propionaldehidefbutyraldehyde, benzaldehyde or aldghmay be employed in the condensation reaction, and considerable modification is possible in the choice of materials to be admixed with our condensation products without departing from our invention.
Having thus described our invention, we claim:
1. A new composition of matter comprising the condensation product resulting from an acidified reaction mixture of sulfite pulp waste liquor, water-soluble aldehyde, urea and thiourea in which reaction mixture 0.1 to 5 mols of aldehyde are present per mol of combined urea and thiourea and said sulfite pulp waste liquor contains no more than 1 gram of sulfite pulp waste liquor solids per gram of combined urea and thiourea.
2. A new composition of matter comprising the condensation product resulting from an acidified reaction mixture of sulfite pulp waste liquor,-
water-soluble aldehyde, and urea in which reaction mixture 0.1 to 5 mols of aldehyde are present per mol of urea and said sulfite pulp waste liquor contains no more than 1 gram or sulfite pulp waste liquor solids per gram of urea. 3. A new composition of matter comprising the condensation product resulting from an acidified reaction mixture of sulfite pulp waste liquor, water-soluble aldehyde, and thiourea in which reaction mixture 0.1 to 5 mols of aldehyde are present per mol of thiourea and said sulfite pulp waste liquor contains no more than 1 gram of sulfite pulp waste liquor solids per gram or thiourea. RALPH E. PLUMP. JAMES W. CARROLL.
References Cited in the file of this patent UNITED STATES PATENTS Number Name Date 1,807,711 Schmidt June 2, 1931 2,266,265 Rieche et a1. Dec. 16, 1941 2,321,451 Bauer June 8, 1943 2,369,613 Schubert Feb. 13, 1945 2,387,619 Seidel Oct. 23, 1945 2,405,650 Hartwig Aug. 13, 1946 FOREIGN PATENTS Number Country Date 74,383 Norway Dec. 6, 1948

Claims (1)

1. A NEW COMPOSITION OF MATTER COMPRISING THE CONDENSATION PRODUCT RESULTING FROM AN ACIDIFIED REACTION MIXTURE OF SULFITE PULP WASTE LIQUOR, WATER-SOLUBLE ALDEHYDE, UREA AND THIOUREA IN WHICH REACTION MIXTURE 0.1 TO 5 MOLES OF ALDEHYDE ARE PRESENT PER MOL OF COMBINED UREA AND THIOUREA AND SAID SULFITE PULP WASTE LIQUOR CONTAINS NO MORE THAN 1 GRAM OF SULFITE PULP WASTE LIQUOR SOLIDS PER GRAM OF COMBINED UREA AND THIOUREA.
US143822A 1950-02-11 1950-02-11 Urea and/or thiourea-aldehyde-sulfite waste liquor condensation product Expired - Lifetime US2664408A (en)

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US349952A US2823184A (en) 1950-02-11 1953-03-23 Composition and process for metal pickling

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2845397A (en) * 1956-04-17 1958-07-29 Us Rubber Co Method of co-coagulating resin treated lignin and a rubber latex and product obtained thereby
US5075402A (en) * 1989-03-27 1991-12-24 Ligno Tech. U.S.A. Non-toxic, stable lignosulfonate-urea-formaldehyde composition and method of preparation thereof

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1807711A (en) * 1931-06-02 Sylvania
US2266265A (en) * 1938-02-19 1941-12-16 Ig Farbenindustrie Ag Manufacture of resinous condensation products from amide-like compounds and purified lignin-sulphonic acids
US2321451A (en) * 1938-07-25 1943-06-08 Gen Aniline & Film Corp Water-soluble condensation product
US2369613A (en) * 1941-01-10 1945-02-13 Schubert Ernst Dyeing and finishing of textiles
US2387619A (en) * 1939-03-25 1945-10-23 J Seidel Production of synthetic tanning material
US2405650A (en) * 1944-06-17 1946-08-13 Swan Finch Oil Corp Core for metallic casting and composition for same

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1807711A (en) * 1931-06-02 Sylvania
US2266265A (en) * 1938-02-19 1941-12-16 Ig Farbenindustrie Ag Manufacture of resinous condensation products from amide-like compounds and purified lignin-sulphonic acids
US2321451A (en) * 1938-07-25 1943-06-08 Gen Aniline & Film Corp Water-soluble condensation product
US2387619A (en) * 1939-03-25 1945-10-23 J Seidel Production of synthetic tanning material
US2369613A (en) * 1941-01-10 1945-02-13 Schubert Ernst Dyeing and finishing of textiles
US2405650A (en) * 1944-06-17 1946-08-13 Swan Finch Oil Corp Core for metallic casting and composition for same

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2845397A (en) * 1956-04-17 1958-07-29 Us Rubber Co Method of co-coagulating resin treated lignin and a rubber latex and product obtained thereby
US5075402A (en) * 1989-03-27 1991-12-24 Ligno Tech. U.S.A. Non-toxic, stable lignosulfonate-urea-formaldehyde composition and method of preparation thereof

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