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Revision as of 04:49, 26 December 2010 editYobot (talk | contribs)Bots4,733,870 editsm WP:CHECKWIKI error fixes + general fixes, References after punctuation per WP:REFPUNC and WP:PAIC using AWB (7507)← Previous edit Latest revision as of 21:39, 24 March 2024 edit undoMazewaxie (talk | contribs)Extended confirmed users, Pending changes reviewers, Rollbackers113,590 editsm WP:GENFIXESTag: AWB 
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{{short description|Antimicrobial preservative used in cosmetics.}}
{{chembox {{chembox
| Watchedfields = changed
| verifiedrevid = 401985436 | verifiedrevid = 404250284
⚫ | <!--ImageFile = Diazolidinyl urea correct formula.png-->
| ImageFile = Diazolidinyl urea erroneous formula.png | ImageFile = Diazolidinyl urea correct formula.png
| ImageSize = | ImageSize = 220
| ImageAlt = Newly determined structure of diazolidinyl urea
⚫ | IUPACName = Correct new structure: 1,3-bis(hydroxymethyl)-1-(1,3,4-tris(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl)urea<br/>Erroneous old structure: 1-(1,3-bis(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl)-1,3-bis(hydroxymethyl)urea
| ImageCaption = newly determined structure
⚫ | OtherNames=Diazolidinylurea<br/>Germall II
⚫ | ImageFile1 = Diazolidinyl urea erroneous formula.png
⚫ | Section1 = {{Chembox Identifiers
| ImageSize1 = 220
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ImageAlt1 = Newly determined structure of diazolidinyl urea
| ImageCaption1 = "traditional" structure
<!--
| ImageFile2 = Diazolidinyl urea 3D ball.png
| ImageSize2 = 220
| ImageAlt2 = Ball-and-stick model of the diazolidinyl urea molecule
-->
⚫ | IUPACName = 1--1,3-bis(hydroxymethyl)urea ''(new)''<br/>1--1,3-bis(hydroxymethyl)urea ''(old)''
⚫ | OtherNames=Diazolidinylurea<br/>Germall II
⚫ |Section1={{Chembox Identifiers
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 56078 | ChemSpiderID = 56078
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
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| StdInChIKey = SOROIESOUPGGFO-UHFFFAOYSA-N | StdInChIKey = SOROIESOUPGGFO-UHFFFAOYSA-N
| CASNo = 78491-02-8 | CASNo = 78491-02-8
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| EINECS = 278-928-2 | EINECS = 278-928-2
| PubChem = 62277 | PubChem = 62277
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>8</sub>H<sub>14</sub>N<sub>4</sub>O<sub>7</sub> | Formula = C<sub>8</sub>H<sub>14</sub>N<sub>4</sub>O<sub>7</sub>
| MolarMass = 278.22 g/mol | MolarMass = 278.22 g/mol
| Appearance = | Appearance =
| Density = | Density =
| MeltingPt = | MeltingPt =
| Solubility = | Solubility =
}} }}
| Section7 = {{Chembox Hazards |Section7={{Chembox Hazards
| NFPA-H = 1
⚫ | Reference = <ref>{{GHS class NZ|id=4706|accessdate=2009-09-06}}.</ref>
| EUIndex = not listed | NFPA-F = 1
| NFPA-R = 0
| GHSPictograms = {{GHS exclamation mark|Skin Sens. 1}}
⚫ | Hazards_ref = {{GHS exclamation mark|Skin Sens. 1}}<ref>{{GHS class NZ|id=4706|access-date=2009-09-06}}</ref>
| GHSSignalWord = WARNING | GHSSignalWord = WARNING
| HPhrases = {{H-phrases|317}}
| PPhrases = {{P-phrases|261|272|280|302+352|333+313|321|363|501}} | HPhrases = {{H-phrases|317}}
| PPhrases = {{P-phrases|261|272|280|302+352|333+313|321|363|501}}
}} }}
| Section8 = {{Chembox Related |Section8={{Chembox Related
| OtherCpds = ] | OtherCompounds = ]
}} }}
}} }}
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It is used in many ], ] products, ]s and conditioners, as well as a wide range of products including bubble baths, baby wipes and household detergents. Diazolidinyl urea is found in the commercially available preservative ]. It is used in many ], ] products, ]s and conditioners, as well as a wide range of products including bubble baths, baby wipes and household detergents. Diazolidinyl urea is found in the commercially available preservative ].


Commercial diazolidinyl urea is a mixture of different formaldehyde addition products including polymers.<ref name="structure">{{Cite journal | first1 = Søren Vig | last1 = Lehmann | first2 = Ulla | last2 = Hoeck | first3 = Jens | last3 = Breinholdt | first4 = Carl Erik | last4 = Olsen | first5 = Bo | last5 = Kreilgaard | year = 2006 | title = Characterization and chemistry of imidazolidinyl urea and diazolidinyl urea | journal = Cont. Dermat. | volume = 54 | issue = 1 | pages = 50–58 | doi = 10.1111/j.0105-1873.2006.00735.x | pmid = 16426294 | postscript = <!--None-->}}.</ref> Commercial diazolidinyl urea is a mixture of different formaldehyde addition products including polymers.<ref name="structure">{{Cite journal | first1 = Søren Vig | last1 = Lehmann | first2 = Ulla | last2 = Hoeck | first3 = Jens | last3 = Breinholdt | first4 = Carl Erik | last4 = Olsen | first5 = Bo | last5 = Kreilgaard | year = 2006 | title = Characterization and chemistry of imidazolidinyl urea and diazolidinyl urea | journal = Contact Dermatitis | volume = 54 | issue = 1 | pages = 50–58 | doi = 10.1111/j.0105-1873.2006.00735.x | pmid = 16426294}}</ref>


== Chemistry == == Chemistry ==
=== Synthesis === === Synthesis ===
Diazolidinyl urea is produced by the ] of ] and ] in the presence of ] solution and heat. The reaction mixture is then ] with ] and ]: Diazolidinyl urea is produced by the ] of ] and ] in the presence of ] solution and heat. The reaction mixture is then ] with ] and ]:


] + 4 H<sub>2</sub>C=O → ] :] + 4 H<sub>2</sub>C=O → ]


=== Structure === === Structure ===
Diazolidinyl urea was poorly characterized until recently and still has a wrong ] structure assigned to it. New data show that the ] ] of the ] ring is attached to the ], not the ] atom:<ref name="structure" /> Diazolidinyl urea was poorly characterized until recently and the single ] structure assigned to it is probably not the major one in the commercial material. Instead, new data indicate that one of the ] ]s of the ] ring is attached to the ], rather than on the urea ] atom:<ref name="structure" />
{| :{|
|- align="center" valign="middle" |- align="center" valign="middle"
| ] | ]
| ] | ]
|- align="center" |- align="center"
| Hoeck structure | Originally reported structure
| previous structure | Hoeck's revised structure
|} |}


== Safety == == Safety ==
Some people have a contact ] to ] causing ].<ref name="NIEHS"> (NTP NIEHS)</ref> Such people are often also allergic to diazolidinyl urea. Some people have a contact ] to ] causing ].<ref name="NIEHS"> (NTP NIEHS)</ref> Such people are often also allergic to diazolidinyl urea.

In addition to being an allergen, it is a ] releaser, since it generates formaldehyde slowly as it degrades. Although the formaldehyde acts as a bactericidal preservative, it is a known carcinogen.

In 2005–06, it was the 14th-most-prevalent ] in ]s (3.7%).<ref>{{cite journal|last1=Zug |first1=K. A. |last2=Warshaw |first2=E. M. |last3=Fowler |first3=J. F. Jr |last4=Maibach |first4=H. I. |last5=Belsito |first5=D. L. |last6=Pratt |first6=M. D. |last7=Sasseville |first7=D. |last8=Storrs |first8=F. J. |last9=Taylor |first9=J. S. |last10=Mathias |first10=C. G. |last11=Deleo |first11=V. A. |last12=Rietschel |first12=R. L. |last13=Marks |first13=J. |title=Patch-test results of the North American Contact Dermatitis Group 2005–2006 |journal=Dermatitis |date=May–June 2009 |volume=20 |issue=3 |pages=149–160}}</ref>


== References == == References ==
{{reflist}} {{reflist}}

==External links==
* {{cite web|url=http://www.orion-health.co.nz/Info%20Cards/Diazolidinyl%20Urea.htm|title=Diazolidinyl urea|work=MEKOS Laboratories AS|accessdate=2007-03-11}}


{{DEFAULTSORT:Diazolidinyl Urea}} {{DEFAULTSORT:Diazolidinyl Urea}}