US3487088A - Process for preparing 1,3-dimethylol-4,5-dihydroxy-2-imidazolidinone - Google Patents

Process for preparing 1,3-dimethylol-4,5-dihydroxy-2-imidazolidinone Download PDF

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Publication number
US3487088A
US3487088A US630847A US3487088DA US3487088A US 3487088 A US3487088 A US 3487088A US 630847 A US630847 A US 630847A US 3487088D A US3487088D A US 3487088DA US 3487088 A US3487088 A US 3487088A
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Prior art keywords
dimethylol
imidazolidinone
dihydroxy
preparing
formaldehyde
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Expired - Lifetime
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US630847A
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English (en)
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Kenneth Herald Remley
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Wyeth Holdings LLC
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American Cyanamid Co
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/30—Oxygen or sulfur atoms
    • C07D233/40—Two or more oxygen atoms

Definitions

  • This invention relates to a process for preparing stable, aqueous solutions of 1,3-dimethylol-4,5-dihydroxy-2-imidazolidinone, sometimes referred to as dimethylol monourein or dimethylol dihydroxyethyleneurea.
  • 1,3-dimethylol-4,5-dihydroxy-Z-imidazolidinone has the following structural formula:
  • iniidazolidinone has become a valuable textile finishing agent particularly for use as a creaseproofing agent on cellulosic textile materials including blends of such materials with other fibers such as polyamides and polyesters. Although it may be employed as a conventional creaseproofing finish in the manner described in U.S. Patent No. 2,731,364, its present commercial importance is as a post-cure creaseproofing finish of the type employable in the process described in U.S. Patent No. 2,974,432.
  • urea and glyoxal are reacted under alkaline conditions to produce 4,5-dihydroxy-2-imidazolidinone, which is then reacted with formaldehyde under neutral or alkaline conditions.
  • a process for preparing a stable aqueous solution of 1,3-dimethylol-4,5-dihydroxy 2 imidazolidinone which comprises reacting relative amounts of 1 mole of urea with from between .8 and 1.3 moles of glyoxal and from 1.6 to 2.5 moles of formaldehyde in an aqueous medium at a pH maintained above 7 and at a temperature maintained between 30 and C.
  • the present invention is concerned with a single step or one pot procedure for preparing what is substantially the equivalent in performance as a creaseproofing agent as similar products prepared by the more costly procedures of the prior art.
  • the mole ratios employed are relatively amounts of 1 mole of urea with between .9 and 1.1 moles of glyoxal and between 1.8 and 2.2 moles of formaldehyde. Applicant has found that uniformly good results have been achieved by adhering to mole ratios within the preferred limits.
  • the aqueous reaction medium must be maintained above 7 and preferably between 7.5 and 9.5.
  • the alkaline pH is obtained by adding sufiicient alkali to provide the initial alkaline pH and by the continuous addition of suitable alkaline materials during the course of the reaction.
  • suitable alkalies include sodium hydroxide, potassium hydroxide, sodium carbonate and their equivalents.
  • the reaction mixture is heated at a temperature of between 30 and 100 C. and preferably between 60 and 70 C. It has been found convenient to permit the temperature of the reaction mixture to gradually rise until the desired reaction temperature is reached. The reaction temperature is maintained until it is essentially complete as evidenced by an unreacted aldehyde content of not over 2%, preferably not over 1.2%.
  • the free formaldehyde content being determined by conventional analytical procedures.
  • the solution is normally cooled and suflicient acid added, preferably hydrochloric acid, to provide a pH of between 5.0 and 5.4.
  • sodium chloride or similar bleaching agents may be employed by addition to the aqueous solution to improve the color still further.
  • Textile finishes obtained by the procedure of this invention are stable, essentially colorless solutions. They are obtained economically and in excellent yield.
  • the products are applicable to cellulosic materials by known procedures and may be durably bound thereto by standard curing procedures.
  • Cellulosic textile materials illustratively cotton fabric, finished with the product of this invention have a high degree of wash-and-wear and other desirable properties, and are not discolored by the finish.
  • the product of this invention may be employed with other textile agents and auxiliaries such as softeners, brighteners, odorants and other creaseproofing agents.
  • Example 1 To a suitable reaction vessel there is added 2,840 parts (41.6 moles) of 44% formalin and 3,000 parts (20.7 moles) of 40% aqueous glyoxal. Suflicient sodium hydroxide, about 55 parts of 24% aqueous caustic soda, is added to provide a pH of 8.08.5, followed by 1,250 parts (20.8 moles) of urea. The temperature of the reaction is allowed to rise to about 50 C. and 45 parts of 24% aqueous caustic soda is added. The temperature is then allowed to rise to 65-70 C. and is maintained at this level for two hours. During the two-hour period, additional amounts of sodium hydroxide are added as 24% aqueous sodium hydroxide in order to maintain the pH at 8-8.5. Thus 50 parts of 24% sodium hydroxide is added after minutes, 25 parts after 30 minutes and 35 parts after one hour.
  • Suflicient sodium hydroxide about 55 parts of 24% aqueous caustic soda, is added to provide a pH of 8.08.5,
  • reaction mixture is cooled to about 30 C. and 7 parts of sodium chlorite is added, followed by sufficient concentrated hydrochloric acid to provide a pH of 5.0- 5.4. To the solution there is added 1,320 parts of water.
  • the product is an aqueous solution of 1,3-dimethylol- 4,5-dihydroxy-2-imidazolidinone containing 45% solids and less than 1.0% of unreacted aldehyde. It is stable on storage and is suitable for application on textile materials without further processing.
  • Example 2 An aqueous pad bath is prepared containing 6.67% solids of the product in Example 1, 0.64% zinc nitrate, 3.0% of a nonionic softener, that is a 25% polyethylene emulsion containing polyethylene glycol monostearate and coconut oil monoethanolamine and 0.25% of a nonionic surface active agent, that is the condensation product of nonylphenol with an average of 9.5 moles of ethylene oxide.
  • a nonionic softener that is a 25% polyethylene emulsion containing polyethylene glycol monostearate and coconut oil monoethanolamine and 0.25% of a nonionic surface active agent, that is the condensation product of nonylphenol with an average of 9.5 moles of ethylene oxide.
  • Cotton broadcloth is impregnated with the pad bath by a standard padding procedure obtaining a 75% wet pickup.
  • the fabric, containing 5.0% solids of the product of Example 1 is dried at 225 F. for one minute and then heated at 350 F. for 1.5 minutes.
  • the tensile strengths of the fabrics are measured by ASTM Standard Method D-39 using a Scott tensile strength tester.
  • the crease recovery angles and tensile strengths of the treated and untreated fabrics are determined as indicated in Example 2.
  • the appearance ratings are relative, 5.0 being maximum, and are a measure of the smoothness of the fabric when viewed under an overhead light, after being washed five times.
  • the washes were carried out in a home-style Washing machine using water at -145 F. and a detergent with a 12-minute wash cycle followed by tumble drying at F. for 30 minutes.
  • the crease retention was determined by inspection of the fabrics after five wash and drying cycles.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US630847A 1967-04-14 1967-04-14 Process for preparing 1,3-dimethylol-4,5-dihydroxy-2-imidazolidinone Expired - Lifetime US3487088A (en)

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US63084767A 1967-04-14 1967-04-14

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US3487088A true US3487088A (en) 1969-12-30

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US (1) US3487088A (enrdf_load_stackoverflow)
BE (1) BE713651A (enrdf_load_stackoverflow)
CH (1) CH497430A (enrdf_load_stackoverflow)
DE (1) DE1770176A1 (enrdf_load_stackoverflow)
FR (1) FR1558244A (enrdf_load_stackoverflow)
GB (1) GB1199687A (enrdf_load_stackoverflow)
NL (1) NL6805193A (enrdf_load_stackoverflow)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3903033A (en) * 1973-05-02 1975-09-02 American Cyanamid Co Urea-glyoxal-formaldehyde cellulose reactant
US4016335A (en) * 1973-05-02 1977-04-05 American Cyanamid Company Urea-glyoxal-formaldehyde cellulose reactant
US4173645A (en) * 1976-12-22 1979-11-06 Bayer Aktiengesellschaft Substituted 4,5-dihydroxy-imidazolidine-2-thiones and their use as ectoparasiticides

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2613361B1 (fr) * 1987-04-02 1989-07-21 Hoechst France Urees substituees, leur procede de preparation et leur application notamment dans l'ennoblissement des fibres cellulosiques

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2731472A (en) * 1956-01-17 Production of heterocyclic compounds
US2755198A (en) * 1953-02-27 1956-07-17 Monsanto Chemicals Novel compositions and treatment of textile materials
US2764573A (en) * 1951-08-17 1956-09-25 Basf Ag Condensation products of glyoxal monourein and aldehydes
US2777857A (en) * 1953-12-31 1957-01-15 Phrix Werke Ag Methylene-1-bis-4, 5-dihydroxytetrahydro-3-hydroxymethylimidazols
US2876062A (en) * 1953-09-03 1959-03-03 Phrix Werke Ag Process of crease-proofing cellulose fibers and fabrics by applying ureaformaldehyde-glyoxal reaction products
US3112156A (en) * 1960-10-07 1963-11-26 Sidney L Vail Treatment of cellulosic textile material with 1, 3-dimethyl-4, 5-dihydroxy-2-imidazolidinone
US3209010A (en) * 1961-11-13 1965-09-28 Gagliardi Res Corp Polyalkylated monoureins

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2731472A (en) * 1956-01-17 Production of heterocyclic compounds
US2764573A (en) * 1951-08-17 1956-09-25 Basf Ag Condensation products of glyoxal monourein and aldehydes
US2755198A (en) * 1953-02-27 1956-07-17 Monsanto Chemicals Novel compositions and treatment of textile materials
US2876062A (en) * 1953-09-03 1959-03-03 Phrix Werke Ag Process of crease-proofing cellulose fibers and fabrics by applying ureaformaldehyde-glyoxal reaction products
US2777857A (en) * 1953-12-31 1957-01-15 Phrix Werke Ag Methylene-1-bis-4, 5-dihydroxytetrahydro-3-hydroxymethylimidazols
US3112156A (en) * 1960-10-07 1963-11-26 Sidney L Vail Treatment of cellulosic textile material with 1, 3-dimethyl-4, 5-dihydroxy-2-imidazolidinone
US3209010A (en) * 1961-11-13 1965-09-28 Gagliardi Res Corp Polyalkylated monoureins

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3903033A (en) * 1973-05-02 1975-09-02 American Cyanamid Co Urea-glyoxal-formaldehyde cellulose reactant
US4016335A (en) * 1973-05-02 1977-04-05 American Cyanamid Company Urea-glyoxal-formaldehyde cellulose reactant
US4173645A (en) * 1976-12-22 1979-11-06 Bayer Aktiengesellschaft Substituted 4,5-dihydroxy-imidazolidine-2-thiones and their use as ectoparasiticides

Also Published As

Publication number Publication date
DE1770176A1 (de) 1971-09-23
FR1558244A (enrdf_load_stackoverflow) 1969-02-21
NL6805193A (enrdf_load_stackoverflow) 1968-10-15
GB1199687A (en) 1970-07-22
CH497430A (de) 1970-10-15
BE713651A (enrdf_load_stackoverflow) 1968-10-14

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