USRE32848E - Anti-microbial reaction product of #9 allantoin and formaldehyde - Google Patents

Anti-microbial reaction product of #9 allantoin and formaldehyde Download PDF

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Publication number
USRE32848E
USRE32848E US06/940,241 US94024186A USRE32848E US RE32848 E USRE32848 E US RE32848E US 94024186 A US94024186 A US 94024186A US RE32848 E USRE32848 E US RE32848E
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Prior art keywords
iaddend
iadd
allantoin
formaldehyde
reaction product
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US06/940,241
Inventor
Philip A. Berke
William E. Rosen
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Sutton Laboratory Inc
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Sutton Laboratory Inc
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Priority claimed from US06/070,502 external-priority patent/US4271176A/en
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Publication of USRE32848E publication Critical patent/USRE32848E/en
Assigned to CHASE MANHATTAN BANK (NATIONAL ASSOCIATION) THE reassignment CHASE MANHATTAN BANK (NATIONAL ASSOCIATION) THE SECURITY INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: SUTTON LABORATORIES, INC.
Assigned to SUTTON LABORATORIES, INC., GAF CHEMICALS CORPORATION, GAF BUILDING MATERIALS CORPORATION reassignment SUTTON LABORATORIES, INC. RELEASED BY SECURED PARTY (SEE DOCUMENT FOR DETAILS). Assignors: CHASE MANHATTAN BANK, THE (NATIONAL ASSOCIATION)
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
    • 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
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
    • C07D233/88—Nitrogen atoms, e.g. allantoin

Definitions

  • the present invention is directed to a .[.compound.]. .Iadd.reaction product .Iaddend.obtained by the reaction of allantoin with formaldehyde.
  • U.S. Pat. No. 3,248,285 describes a series of compounds prepared by condensing allantoin with formaldehyde which exhibits bacteriostatic and/or bactericidal activity. Because of this activity, the compounds are effective as preservatives in cosmetics and other products susceptible to bacterial contamination. However, since cosmetics and most other perishable products are subject to contamination by yeast and mold as well as bacteria, the compounds must be used in combination with other preservatives which are effective against yeast and mold. Such preservatives are typically referred to as antifungal agents.
  • the parabens i.e., esters of p-hydroxybenzoic acid
  • the additional preservative components which provide protection against yeast and mold.
  • the combination of parabens with the aforementioned bacteria-combating compounds works well and is widely used in the cosmetic industry, it presents certain heretofore unsolved problems.
  • the parabens, as well as a great many other antifungal agents are easily inactivated or deactivated.
  • Inactivation of parabens and like compounds may be attributed to several factors including the migration of the compounds from the aqueous phase of an emulsion to the oil phase, the binding of the compounds by commonly used nonionic emulsifiers, and/or the interfering effect of other components in the product sought to be protected. Inactivation is particularly acute in cosmetics since nonionic emulsifiers inactivate antifungal agents and are common ingredients in cosmetic emulsions such as creams and lotions. Thus, cosmetic formulators are often unable to adequately preserve such emulsions against yeast or mold contamination.
  • compounds prepared in accordance with the disclosure of U.S. Pat. No. 3,248,285 are not inactivated by nonionic emulsifiers, do not migrate from the aqueous to the oil phase, and are not deleteriously affected by other ingredients in the various preserved products.
  • the compounds heretofore prepared in accordance with the teachings of U.S. Pat. No. 3,248,285 exhibit only bacteriostatic and/or bactericidal activity. They do not exhibit adequate antimicrobial activity against yeast and mold. Parabens or similar compounds are, therefore, still required to adequately protect cosmetic and other perishable products even though they are susceptible to deactivation.
  • Another object of the invention is to provide a preservative composition containing a .[.single compound.]. .Iadd.reaction product .Iaddend.as the sole active ingredient against bacteria, yeast or mold.
  • Still another object of the invention is to provide a method for preserving products against contamination by bacteria, mold and yeast.
  • .Iadd.reaction product .Iaddend. is not only active against bacteria, but is also especially effective against yeast and mold.
  • this .[.compound.]. .Iadd.reaction product.Iaddend. it is possible to preserve formulations, especially emulsions, which have previously been vulnerable to contamination by yeast and mold even when protected by conventional antifungal agents.
  • the .[.compound.]. .Iadd.reaction product.Iaddend.of the invention can be used as the sole preservative component in perishable product formulations.
  • reaction product of the invention .Iaddend.is prepared by condensing allantoin and formaldehyde in precise quantities.
  • the reaction may be conducted in the presence of a basic catalyst, such as sodium hydroxide.
  • the reactants are mixed in a ratio of one mole of allantoin for every four moles of formaldehyde optionally with the basic catalyst, in an aqueous medium and heated to reflux. A clear, aqueous solution is obtained.
  • the .[.compound.]. .Iadd.reaction product .Iaddend.of the invention is water-soluble, it may be readily incorporated into aqueous solutions or the aqueous phase of emulsions. In solid formulations, .[.the compound.]. .Iadd.it .Iaddend.is incorporated in powder form. The amount of the .[.compound.]. .Iadd.reaction product .Iaddend.required to provide adequate protection against microbial contamination will, of course, vary, depending upon the particular product being preserved. Those of skill in the art can easily determine dose levels in particular applications without undue experimentation.
  • the .[.compound.]. .Iadd.reaction product .Iaddend.of the invention provides a significant improvement over similar preservative compounds heretofore available. Since it is effective against bacteria, mold and yeast, it can be used as the sole preservative component in many products. This eliminates the need to include antifungal preservatives such as parabens which are susceptible to deactivation in various, common environments.
  • the .[.compound.]. .Iadd.reaction product .Iaddend.of the invention is, therefore, a dependable, effective preservative which offers significant advantages over the individual preservatives, as well as preservative combinations, currently recognized and employed by those of skill in the art.
  • a 0.5 ml. aliquot of a 24 hour A.O.A.C. yeast broth culture was added to 4.5 ml. of the test solution and mixed well.
  • the test solution was then stored at 35° C. in an incubator for 3 days.
  • a 0.1 ml. aliquot was aseptically removed from the test solution and placed into a tube containing Sabourand Liquid Medium with Letheen. The inoculated subculture tube was incubated at 35° C. for 2 days and then examined for the presence of growth.
  • the growth of a 7-10 day mold slant was washed off with 10 ml. of sterile saline.
  • a 0.5 ml. aliquot of the wash suspension was added to 4.5 ml. of the test solution, mixed, incubated and a 0.1 ml. aliquot transferred to Sabourand Liquid Media with Letheen, as described above for yeast.
  • the inoculated subculture tube was incubated at 25° C. for 7 days and then examined for the presence of growth.
  • test solutions were compared at 0.4% concentration. Under these conditions, both C. albicans and A. niger were killed within 2 days in 0.4% .[.N-(hydroxymethyl)-N-(1,3-dihydroxymethyl-2,5-dioxo-4-imidazolidinyl)-N'-(hydroxymethyl)urea.]. .Iadd.of the reaction product of formaldehyde and allantoin in the proportion of four moles formaldehyde to one mole allantoin.Iaddend..

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

.[.N-hydroxymethyl)-N-(1,3-dihydroxymethyl-2,5-dioxo-4-imidazolidinyl)-N'-(hydroxymethyl)urea.]. .Iadd.A reaction product .Iaddend.prepared by the reaction of allantoin and formaldehyde is disclosed. The .[.compound.]. .Iadd.reaction product .Iaddend.exhibits activity against bacteria, mold and yeast and hence is useful as a preservative for products susceptable to microbial contamination.

Description

This is a division of application Ser. No. 70,502, filed Aug. 28, 1979, now U.S. Pat. No. 4,271,176, issued June 2, 1981.
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention is directed to a .[.compound.]. .Iadd.reaction product .Iaddend.obtained by the reaction of allantoin with formaldehyde. The .[.compound.]. .Iadd.reaction product .Iaddend.exhibits activity against bacteria, mold and yeast and hence is useful as a preservative for products susceptible to microbial contamination.
2. Description of the Prior Art
U.S. Pat. No. 3,248,285 describes a series of compounds prepared by condensing allantoin with formaldehyde which exhibits bacteriostatic and/or bactericidal activity. Because of this activity, the compounds are effective as preservatives in cosmetics and other products susceptible to bacterial contamination. However, since cosmetics and most other perishable products are subject to contamination by yeast and mold as well as bacteria, the compounds must be used in combination with other preservatives which are effective against yeast and mold. Such preservatives are typically referred to as antifungal agents.
Generally, the parabens, i.e., esters of p-hydroxybenzoic acid, are used as the additional preservative components which provide protection against yeast and mold. Although the combination of parabens with the aforementioned bacteria-combating compounds works well and is widely used in the cosmetic industry, it presents certain heretofore unsolved problems. In particular, the parabens, as well as a great many other antifungal agents, are easily inactivated or deactivated. Inactivation of parabens and like compounds may be attributed to several factors including the migration of the compounds from the aqueous phase of an emulsion to the oil phase, the binding of the compounds by commonly used nonionic emulsifiers, and/or the interfering effect of other components in the product sought to be protected. Inactivation is particularly acute in cosmetics since nonionic emulsifiers inactivate antifungal agents and are common ingredients in cosmetic emulsions such as creams and lotions. Thus, cosmetic formulators are often unable to adequately preserve such emulsions against yeast or mold contamination.
In contrast to the parabens and other antifungal agents, compounds prepared in accordance with the disclosure of U.S. Pat. No. 3,248,285 are not inactivated by nonionic emulsifiers, do not migrate from the aqueous to the oil phase, and are not deleteriously affected by other ingredients in the various preserved products. Unfortunately, the compounds heretofore prepared in accordance with the teachings of U.S. Pat. No. 3,248,285 exhibit only bacteriostatic and/or bactericidal activity. They do not exhibit adequate antimicrobial activity against yeast and mold. Parabens or similar compounds are, therefore, still required to adequately protect cosmetic and other perishable products even though they are susceptible to deactivation. Hence, there exists a need for a .[.single compound.]. .Iadd.product .Iaddend.which is effective against microbial contamination by yeast and mold as well as bacteria and which is easily incorporated into products, particularly cosmetic products, without suffering a significant reduction in activity.
SUMMARY OF THE INVENTION
Accordingly, it is an object of the invention to provide a .[.compound.]. .Iadd.reaction product .Iaddend.which exhibits activity against bacteria, yeast and mold and which is easily incorporated into a variety of products susceptible to microbial contamination without losing activity.
Another object of the invention is to provide a preservative composition containing a .[.single compound.]. .Iadd.reaction product .Iaddend.as the sole active ingredient against bacteria, yeast or mold.
Still another object of the invention is to provide a method for preserving products against contamination by bacteria, mold and yeast.
Other objects and advantages of the invention will be evident to those of ordinary skill in the art upon review of the detailed description of the invention contained herein.
DETAILED DESCRIPTION OF THE INVENTION
The foregoing objects and advantages are provided by a .[.compound represented by the structural formula: ##STR1## named N-(hydroxymethyl)-N-(1,3-dihydroxymethyl-2,5-dioxo-4-imidazolidinyl)-N'-(hydroxymethyl)urea.]. .Iadd.reaction product formed by condensing formaldehyde and allantoin in the proportion of four moles of formaldehyde to one mole of allantoin.Iaddend.. Unlike the numerous other compounds which fall within the generic structural formula disclosed in U.S. Pat. No. 3,248,285, this .[.compound.]. .Iadd.reaction product .Iaddend.is not only active against bacteria, but is also especially effective against yeast and mold. Hence, using this .[.compound.]. .Iadd.reaction product.Iaddend., it is possible to preserve formulations, especially emulsions, which have previously been vulnerable to contamination by yeast and mold even when protected by conventional antifungal agents. Moreover, because of its general effectiveness against a wide range of microbial contaminants, the .[.compound.]. .Iadd.reaction product.Iaddend.of the invention can be used as the sole preservative component in perishable product formulations.
.[.N-(hydroxymethyl)-N-(1,3-dihydroxymethyl-2,5-dioxo-4-imidazolidinyl)-N'-(hydroxymethyl)urea.]. .Iadd.The reaction product of the invention .Iaddend.is prepared by condensing allantoin and formaldehyde in precise quantities. The reaction may be conducted in the presence of a basic catalyst, such as sodium hydroxide. The reactants are mixed in a ratio of one mole of allantoin for every four moles of formaldehyde optionally with the basic catalyst, in an aqueous medium and heated to reflux. A clear, aqueous solution is obtained. Drying the solution produces the .[.N-(hydroxymethyl)-N-(1,3-dihydroxymethyl-2,5-dioxo-4-imidazolidinyl)-N'-(hydroxymethyl)urea.]. .Iadd.reaction product .Iaddend.as a water-soluble white powder residue.
Because the .[.compound.]. .Iadd.reaction product .Iaddend.of the invention is water-soluble, it may be readily incorporated into aqueous solutions or the aqueous phase of emulsions. In solid formulations, .[.the compound.]. .Iadd.it .Iaddend.is incorporated in powder form. The amount of the .[.compound.]. .Iadd.reaction product .Iaddend.required to provide adequate protection against microbial contamination will, of course, vary, depending upon the particular product being preserved. Those of skill in the art can easily determine dose levels in particular applications without undue experimentation.
The .[.compound.]. .Iadd.reaction product .Iaddend.of the invention, thus, provides a significant improvement over similar preservative compounds heretofore available. Since it is effective against bacteria, mold and yeast, it can be used as the sole preservative component in many products. This eliminates the need to include antifungal preservatives such as parabens which are susceptible to deactivation in various, common environments. The .[.compound.]. .Iadd.reaction product .Iaddend.of the invention is, therefore, a dependable, effective preservative which offers significant advantages over the individual preservatives, as well as preservative combinations, currently recognized and employed by those of skill in the art.
To further illustrate the various advantages provided by the present invention, the following examples are provided. However, it is understood that their purpose is entirely illustrative and in no way intended to limit the scope of the invention. In the examples, percentages are given by weight.
EXAMPLE 1 (A) Preparation of .[.N-(hydroxymethyl)-N-(1,3-dihydroxymethyl-2,5-dioxo-4-imidazolidinyl)-N'-(hydroxymethyl)urea.]. .Iadd.reaction product with basic catalysis .Iaddend.
A stirred suspension of 158.1 g. of allantoin in 324.2 g. of 37% formaldehyde was treated with 32.0 g. of 10% aqueous sodium hydroxide, and heated to reflux. After one hour of refluxing, the clear colorless solution was dried at reduced pressure to a white solid residue. Anal. Calc'd. for C8 H14 N4 O7 (278.23): N,20.14%. Found: N,19.85%. The power was completely soluble in water as a 30% solution.
(B) Preparation of .[.N-(hydroxymethyl)-N-(1,3-dihydroxymethyl-2,5-dioxo-4-imidazolidinyl)-N'-(hydroxymethyl)urea.]. .Iadd.reaction product without catalysis .Iaddend.
Addition of 1053 g. of allantoin to 2160 g. of 37% formaldehyde with stirring gave a white suspension. The suspension was stirred and heated to 85° C., and held at that temperature for 1 hour. Cooling to room temperature gave a clear colorless solution .[.of N-(hydroxymethyl)-N-(1,3-dihydroxymethyl-2,5-dioxo-4-imidazolidinyl)-N'-(hydroxymethyl)urea.].. Removal of water at reduced pressure left a white powder.
EXAMPLE 2
Activity against yeast and mold: 0.3% test solutions.
A 0.5 ml. aliquot of a 24 hour A.O.A.C. yeast broth culture was added to 4.5 ml. of the test solution and mixed well. The test solution was then stored at 35° C. in an incubator for 3 days. A 0.1 ml. aliquot was aseptically removed from the test solution and placed into a tube containing Sabourand Liquid Medium with Letheen. The inoculated subculture tube was incubated at 35° C. for 2 days and then examined for the presence of growth.
The growth of a 7-10 day mold slant was washed off with 10 ml. of sterile saline. A 0.5 ml. aliquot of the wash suspension was added to 4.5 ml. of the test solution, mixed, incubated and a 0.1 ml. aliquot transferred to Sabourand Liquid Media with Letheen, as described above for yeast. The inoculated subculture tube was incubated at 25° C. for 7 days and then examined for the presence of growth.
__________________________________________________________________________
                                 Subculture after 3 days*                 
                                 C. albicans                              
                                        A. niger                          
Test Solution                    ATCC 10231                               
                                        ATCC 9642                         
__________________________________________________________________________
0.3% Imidazolidinyl Urea**       +      +                                 
0.3% .[.N--(hydroxymethyl)-N--                                            
                 .Iadd.reaction product of formaldehyde.Iaddend.          
                                 -      -                                 
(1,3-dihydroxymethyl-2,5-                                                 
                 .Iadd.and allantoin in the proportion.Iaddend.           
dioxo-4-imidazolidinyl)-N'--                                              
                 .Iadd.of four moles formaldehyde to.Iaddend.             
(hydroxymethyl)urea.].                                                    
                 .Iadd.one mole allantoin.Iaddend.                        
__________________________________________________________________________
 *+ = Growth, - = No Growth                                               
 **Compound prepared in accordance with Example 4 of U.S. Pat. No.        
 3,243,285
EXAMPLE 3
Activity against yeast and mold: 0.4% test solutions.
Using the same critical killing time procedure as described in Example 2, test solutions were compared at 0.4% concentration. Under these conditions, both C. albicans and A. niger were killed within 2 days in 0.4% .[.N-(hydroxymethyl)-N-(1,3-dihydroxymethyl-2,5-dioxo-4-imidazolidinyl)-N'-(hydroxymethyl)urea.]. .Iadd.of the reaction product of formaldehyde and allantoin in the proportion of four moles formaldehyde to one mole allantoin.Iaddend..
__________________________________________________________________________
                                 Subculture after 2 days*                 
                                 C. albicans                              
                                        A. niger                          
Test Solution                    ATCC 10231                               
                                        ATCC 9642                         
__________________________________________________________________________
0.4% Imidazolidinyl Urea         -      +                                 
0.4% .[.N--(hydroxymethyl)-N--                                            
                 .Iadd.reaction product of formaldehyde.Iaddend.          
                                 -      -                                 
(1,3-dihydroxymethyl-2,5-                                                 
                 .Iadd.and allantoin in the proportion.Iaddend.           
dioxo-4-imidazolidinyl)-N'--                                              
                 .Iadd.of four moles formaldehyde to.Iaddend.             
(hydroxymethyl)urea.].                                                    
                 .Iadd.one mole allantoin.Iaddend.                        
__________________________________________________________________________
 *+ = Growth, - = No Growth
While the invention has been described in terms of various preferred embodiments, the skilled artisan will appreciate that various modifications, substitutions, omissions, and changes may be made without departing from the spirit thereof. Accordingly, it is intended that the scope of the present invention be limited solely by the scope of the following claims.

Claims (2)

    What is claimed is: .[.1. A condensation product of formaldehyde and allantoin in the proportion of four moles of formaldehyde to one mole of allantoin having the structural formula: ##STR2##
  1. .Iadd.2. A reaction product formed by condensing formaldehyde and allantoin in the proportion of four moles of formaldehyde to one mole of allantoin, said reaction product exhibiting anti-microbial activity
  2. against bacteria, yeast and mold. .Iaddend. .Iadd.3. The product as claimed in claim 2, wherein said condensation is conducted in the presence of a basic catalyst. .Iaddend. .Iadd.4. The product as claimed in claim 2, wherein said condensation is conducted at elevated temperature. .Iaddend. .Iadd.5. The product as claimed in claim 4, wherein said condensation is conducted at reflux temperature. .Iaddend. .Iadd.6. The product as claimed in claim 2, wherein said condensation is conducted in an aqueous medium. .Iaddend.
US06/940,241 1979-08-28 1986-12-10 Anti-microbial reaction product of #9 allantoin and formaldehyde Expired - Lifetime USRE32848E (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US06/940,241 USRE32848E (en) 1979-08-28 1986-12-10 Anti-microbial reaction product of #9 allantoin and formaldehyde

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US06/070,502 US4271176A (en) 1979-08-28 1979-08-28 N-(Hydroxymethyl)-N-(1,3-dihydroxymethyl-2,5-dioxo-4-imidazolidinyl)-N'-(hydroxymethyl)urea used as a preservative agent
US06/940,241 USRE32848E (en) 1979-08-28 1986-12-10 Anti-microbial reaction product of #9 allantoin and formaldehyde

Related Parent Applications (2)

Application Number Title Priority Date Filing Date
US06/070,502 Division US4271176A (en) 1979-08-28 1979-08-28 N-(Hydroxymethyl)-N-(1,3-dihydroxymethyl-2,5-dioxo-4-imidazolidinyl)-N'-(hydroxymethyl)urea used as a preservative agent
US06/214,993 Reissue US4487939A (en) 1979-08-28 1980-12-10 N-(hydroxymethyl)-N-(1,3-dihydroxymethyl-2,5-dioxo-4-imidazolidinyl)-N'-(hydroxymethyl)urea

Publications (1)

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USRE32848E true USRE32848E (en) 1989-01-31

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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3248285A (en) * 1962-08-16 1966-04-26 Sutton Lab Inc Allantoin-formaldehyde condensation products

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3248285A (en) * 1962-08-16 1966-04-26 Sutton Lab Inc Allantoin-formaldehyde condensation products

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