However, the subsequent reaction of the formed amine with further isocyanate, to produce a urea, is even faster (Hegarty et al., 1975). Prepared by International Isocyanate Institute for Bayer AG, Leverkusen (Report No.10417). Allergy, 40:314320. Specific IgG and IgE antibodies to MDIHSA conjugates were present in all subjects. 2. water, the rate of reaction is very slow at temperatures below 122F (50C). In the case of TDI-polyurea, concentrations of free 2,4- and 2,6-toluenediamine in water were measured after hydrolysis at 120, 140, and 160 degrees C. Liss GM, Tarlo SM, Banks DE (1996) Evidence for occupational asthma among compensation claimants at a polyurethane utilizing facility. Published under the joint sponsorship of the United Nations Environment Programme, the International Labour Organization, and the World Health Organization, and produced within the framework of the Inter-Organization Programme for the Sound Management of Chemicals. Case reports as well as epidemiological studies have described MDI as a cause of occupational dermatitis, skin sensitization, and asthma. Lyon, International Agency for Research on Cancer, pp. Lushniak BD, Reh CM, Bernstein DI, Gallagher JS (1998) Indirect assessment of 4,4-diphenylmethane diisocyanate (MDI) exposure by evaluation of specific humoral immune responses to MDI conjugated to human serum albumin. Heimbach F, Jaeger K, Sporenberg W (1996) Fate and biological effects of polymeric MDI in small artificial ponds. Three ponds contained groundwater, above natural lake sediment, to which caged rainbow trout (Oncorhynchus mykiss) were added. 11 Isocyanates react with water to form amines. Hazards Identification Emergency Overview . American journal of respiratory and critical care medicine, 150:988994. Le MDI ne prsente aucune toxicit pour les poissons, les invertbrs aquatiques, les algues ou les microorganismes dans des conditions dexposition susceptibles de gnrer une intoxication aigu ou chronique. After 21 days of exposure to the highest nominal concentration tested (10 mg/litre), PMDI had no effect on the reproduction rate of Daphnia magna (Caspers et al., 1986). lPT RLgNP=ACa0+4"H?N-6]6 @ X[2 Cancer incidence and mortality patterns were investigated in a cohort of 4154 workers employed in Swedish polyurethane foam manufacturing plants for at least 1 year (Hagmar et al., 1993a). The highest level of MDA or degradation products was detected in the maternal blood, followed by the placenta, fetus, and amniotic fluid (at 66.4%, 42.4%, and 13.6% of the maternal blood levels, respectively). Toxicologist, 6:15. Similarly, a few tests on terrestrial organisms did not show any effects under the testing conditions. Base-catalysed reactions of isocyanates with alcohols should be carried out in inert solvents. Le compos est ensuite limin avec ses mtabolites, 57 et 13 % de la radioactivit tant respectivement rcuprs dans les matires fcales et les urines au bout de 4 jours. Herd ZL, Bernstein DI (1994) Antigen-specific stimulation of histamine releasing factors in diisocyanate-induced occupational asthma. American review of respiratory disease, 147:338346. Sepai O, Schuetze D, Heinrich U, Hoymann HG, Henschler D, Sabbioni G (1995a) Hemoglobin adducts and urine metabolites of 4,4-methylenediamine after 4,4-methylenediphenyl diisocyanate exposure of rats. One worker from group I with asthmatic symptoms exhibited cutaneous reactivity and RAST binding to MDIHSA (25.5%). Cuando se produce un vertido al suelo o al agua, el MDI tiene una existencia fugaz, debido a que reacciona con el agua para producir de manera predominante poliureas insolubles. Official websites use .gov Cincinnati, OH, US Department of Health and Human Services, Public Health Service, Centers for Disease Control, National Institute for Occupational Safety and Health (Report No. Because commercial applications using PMDI generate aerosols (Dharmarajan, 1979), traditional techniques that have been successfully used to measure isocyanate vapours (e.g., the Marcali and paper tape colorimetric methods) are generally not suitable for quantitative measurements of MDI in air. ENVIRONMENTAL TRANSPORT, DISTRIBUTION, AND TRANSFORMATION, 6. Two different reaction mechanisms for this transformation are possible, namely "phosgenations first" and "step-wise phosgenations". Dans une autre tude sur le PMDI, la NOAEL relative la toxicit pour les mres et les foetus a t estime 4 mg/m3, en se basant sur la mort prmature dun certain nombre de rattes gravides et sur la diminution statistiquement significative du poids placentaire et du poids foetal la dose de 12 mg/m3. Des renseignements sur lexamen par des pairs du prsent CICAD sont par ailleurs donns lappendice 2. Le PMDI est un liquide brun-rouge fonc dont le point de fusion, mal dfini, se situe autour de 0 C. British journal of industrial medicine, 50:528536. Polyester-polyurethane adhesive formulated from the following: Polyurethane component prepared from polypropylene glycol, toluene diisocyanate, allophanate-modified methane diphenyl diisocyanate and 4,4'-diphenylmethane diisocyanate (CAS Reg. They are based on selected national or regional evaluation documents or on existing EHCs. OSHA Technical Manual (OTM). Studies of workers have identified free MDA, acetylated MDA, and adducts of both with haemoglobin or albumin in urine and blood. However, it should be noted that this guidance value may not protect against occupational sensitization. Diphenylmethane diisocyanate (MDI) is the generic name of a product used in industrial settings. In a case who had experienced repeated attacks of a work-related pulmonary or systemic disease, association with exposure to MDI was examined because of acute respiratory disorder, rhinoconjunctivitis, and a late systemic reaction after exposure to polyurethane pyrolysis products, including MDI (air level 15 g/m3) (Littorin et al., 1994). Compared with the controls, the foundry workers had more respiratory symptoms and a significantly lower mean FEV1 and forced expiratory flow from 25% to 75% of the FVC (FEF2575, or mid-expiratory flow rate of the FVC). tration of 4,4 -methylenediphenyl diisocyanate in guinea-pigs, while no such reaction was observed after inhalation treatment (approximately 21.5 mg/m3 for 3 h per day on five consecutive days) (Rattray et al., 1994). In humans, MDA levels in urine and (after strong acid hydrolysis) in blood were reported to be correlated with exposure to PMDI/MDI (Schuetze et al., 1995; Sepai et al., 1995b; Skarping & Dalene, 1995). There are no adequate data available to serve as a basis for estimating risk of occupational asthma. (1995b) examined biological samples (urine and blood) from 20 workers (as well as 2 unexposed reference workers) exposed to MDI vapour during the manufacture of polyurethane products, together with the levels of MDI in the air of the working environment. It is reported, however, that a ventilation duct was installed above the moulding machine several months before the analysis, and that before then samples exceeding 0.2 mg/m3 had occurred frequently (Diller & Herbert, 1982). The increase in macrophage accumulation at the level of the alveolar septa was related to exposure, and the difference between treatment groups and controls was statistically significant in males exposed to 4.1 mg/m3 and in females at 8.4 mg/m3. Solitary pulmonary adenomas, described as rare in this strain, were observed in males (6/60) and females (2/59) exposed to 6.03 mg/m3 compared with controls (0/120). Se busc la bibliografa hasta noviembre de 1998 mediante MEDLINE, para localizar cualquier informacin nueva pertinente a la evaluacin. POLYMERIC DIPHENYLMETHANE DIISOCYANATE reacts with water slowly forming heavy scum and liberating carbon dioxide gas. A similar, smaller difference was seen with non-Hodgkins lymphoma. Publications of the World Health Organization enjoy copyright protection in accordance with the provisions of Protocol 2 of the Universal Copyright Convention. Where spillage is to soil or water, MDI has a transient existence due to its reaction with the water to produce predominantly insoluble polyureas. Access the public comment docket for the Methylene Diphenyl Diisocyanate (MDI) Action Plan (Docket ID EPA-HQ-OPPT-2011-0182) on Regulations.gov. Because of the relatively low number of workers (25) exposed to MDI (less than 0.04 mg/m3), the short study duration, confounding from prior exposure to TDI (0.05 mg/m3) and possibly to amine catalyst, and the uncertainty in the actual duration of MDI exposure, this study offers limited assurance that MDI is without effect on pulmonary function. Signs of less severe respiratory distress were also observed in animals exposed to 8.4 mg/m3. EPA has developed a separate Action Plan for Toluene Diiscyanate (TDI) and its related compounds. A lock (LockA locked padlock) or https:// means youve safely connected to the .gov website. Center for Computational Quantum Chemistry, University of Georgia, 140 Cedar Street, Athens, Georgia, USA International archives of occupational and environmental health, 61(8):495501. Issue a data call-in for uncured MDI under TSCA section 8(c) to determine if there are allegations of significant adverse effects and initiate a TSCA section 8(d) rulemaking for one-time reporting of relevant unpublished health and safety studies for uncured MDI. The stability of MDI in a model and a real-test environment was studied (Seel et al., 1999). In the polyurethane industry, the undesirable dimerization and oligomerization of methylene diphenyl diisocyanate (MDI) are unwanted and problematic phenomena. V 92.102). A foundry worker who died at work had a diagnosis of occupational asthma induced by MDI assessed 5 years earlier, but had had a poor prognosis for occupational asthma and had continued to be exposed to MDI (Carino et al., 1997). Carcinogenesis, 16(3): 573582. Archives des maladies professionelles de mdecine du travail et de scurit sociale (Paris), 47:311 (in French). When MDI concentrations were kept largely below this concentration, significant changes in lung spirometry were no longer seen, although the incidence of respiratory symptoms was increased significantly. Il est toutefois soluble dans loctane, le benzne et le krosne. since reaction between water and hot diisocyanate can be vigorous. Le MDI est utilis pour la fabrication delastomres base de polyurthane (roulements, emballages, amortisseurs de vibrations, cuirs synthtiques, etc. (1998) evaluated whether MDI-specific IgG or IgE could be sensitive biological markers of disease or of MDI exposure. MDI is not acutely toxic to laboratory mammals. (1995b) reported the formation of adducts of MDA and acetylated MDA with haemoglobin or albumin in the blood of workers exposed to MDI, as described in section 6.2. TDI is chemically similar to MDI and presents similar hazard and exposure concerns, but . Three workers had radiographic evidence of pneumoconiosis, and 12 had asthma, defined as the presence of bronchial hyperreactivity, cough, and additional respiratory symptoms, such as wheeze, chest tightness, or breathlessness. DOI: 10.1039/D1CP03302F. Hay una informacin muy limitada sobre la toxicocintica del MDI. Whether there was exposure to other substances that could cause asthma or whether there was pre-existing asthma was not reported, and guidelines followed for performing FEV1 measurements were not stated. With this third step of its multiphase capacity expansion, BASF will increase production capacity to 600,000 metric tons per year by the middle of the decade and support the ongoing growth of its North American MDI customers. Methylene diphenyl diisocyanate (MDI) and toluene diisocyanate (TDI) are high production volume chemicals used for the manufacture of polyurethanes. Sin embargo, los resultados de las pruebas acuticas carecen de valor, debido a que el MDI es prcticamente insoluble en agua. In vitro, the circulating immune complexes in serum increased after the addition of MDIHSA. Environ. The finding of placental transfer of MDI and its degradation product from pregnant rats exposed to aerosol to fetuses demands further study on its relevance to human risk assessment. IDENTITY AND PHYSICAL/CHEMICAL PROPERTIES, 4. Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations. Aquatic life study, Phase II-2. For more information search the European Chemicals Agency database. Participants at the Final Review Board meeting are listed in Appendix 3. Mancuso G, Reggiani M, Berdondini RM (1996) Occupational dermatitis in shoemakers. A satellite group of rats (10/sex/exposure level) was exposed No. The most widely used aromatic diisocyanates are toluene diisocyanate (TDI) and methylene diphenyl diisocyanate (MDI). Il est rare que lon soit fortement expos dans le milieu ambiant. 3. Dans les conditions normales, lexposition de la population gnrale au MDI devrait provenir uniquement des missions de ce compos dans latmosphre. However, there is insufficient human evidence to describe (1) the nature of the MDI-containing material, (2) the concentrationresponse relationship, or (3) the mechanism of isocyanate-induced asthma and sensitization. PMDI used in experiments is complex and composed of 56 major constituents having 24 aromatic rings. En un estudio de toxicidad/carcinogenicidad por inhalacin crnica de dos aos, las ratas expuestas a un aerosol de PMDI en concentraciones de 0, 0,19, 0,98, y 6,03 mg/m3 mostraron cambios en el aparato respiratorio. Chin J Chem Eng 25(10):14351441, Cao Y et al (2015) Kinetics of the decomposition of dimethylhexane-1,6-dicarbamate to 1,6-hexamethylene diisocyanate. TDI and MDI can be released into the air, water, and soil at places where they are made or used. Although different methods were applied to solubilize the test substance in the test media (e.g., stirring for several hours), the results presented in section 5.1 indicate that only minor amounts of the applied MDI could have been present in the test solution, as the MDI would have rapidly undergone hydrolysis. endstream endobj 22 0 obj <> endobj 23 0 obj <>/Border[0 0 0]/F 4/Rect[377 494 392 509]/Subtype/Link/Type/Annot>><>/Border[0 0 0]/F 4/Rect[432 166 453 181]/Subtype/Link/Type/Annot>><>/Border[0 0 0]/F 4/Rect[468 166 507 181]/Subtype/Link/Type/Annot>><>/Border[0 0 0]/F 4/Rect[175 152 220 167]/Subtype/Link/Type/Annot>>]/Contents[26 0 R 27 0 R 29 0 R 30 0 R 31 0 R 32 0 R 33 0 R 34 0 R]/CropBox[0 0 612 792]/MediaBox[0 0 612 792]/Parent 19 0 R/Resources<>/Font<>/ProcSet[/PDF/Text]>>/Rotate 0/Type/Page>> endobj 24 0 obj <>stream El presente CICAD sobre el diisocianato de difenilmetano (MDI) se prepar en el Instituto Nacional de Ciencias de la Salud, Japn, en colaboracin con el Centro Nacional para la Evaluacin del Medio Ambiente, la Agencia para la Proteccin del Medio Ambiente de los Estados Unidos (EPA). 207 and a terrestrial plant growth test conducted according to OECD Guideline No. It has a boiling point of >300 C at 101.3 kPa, a melting point of 3943 C, and a vapour pressure of <1 mPa at 20 C. 4,4'-methylene diphenyl diisocyanate. They are selected because of their expertise in human and environmental toxicology or because of their experience in the regulation of chemicals. Paris (unpublished report; Report No. It is possible that the reaction products of steam and polymers of MDI, alone or in combination with MDI, may be the causative agents. The polyureas formed from MDI appear to be stable to chemical attack, as would be expected from its insolubility and the stability of ureas. https://doi.org/10.1007/s10965-022-02929-3. Sangyo Igaku (Japanese journal of industrial health), 35:360363 (in Japanese). Prepared by BASF, Ludwigshafen, for US Environmental Protection Agency (unpublished; Project No. Figure 3.3 World methylene diphenyl diisocyanate (MDI) market share by end use application 13 Figure 3.4 World methylene diphenyl diisocyanate (MDI) demand by region 14 . In a well conducted developmental range-finding study, conducted according to Organisation for Economic Co-operation and Development (OECD) Guideline No. Both positive and negative results were obtained when monomeric MDI dissolved in dimethyl sulfoxide (DMSO) was tested in vitro with Salmonella typhimurium. We present very high-level ab initio computations on the HNCO + H2O re The RDDR adjusts for dosimetric differences between laboratory animals and humans by applying normalizing factors to various areas of the respiratory tract. Geometries obtained with a composite method and refined with CCSD(T)/CBS single point energies determine that substituted RNCO species have a significant influence on these barrier heights, with an extreme case like fluorine lowering both barriers by close to 15 kcal mol1 and most common alkyl substituents lowering both by approximately 3 kcal mol1. The reactions between substituted isocyanates (RNCO) and other small molecules (e.g. Responsible authorities are strongly encouraged to characterize risk on the basis of locally measured or predicted exposure scenarios. Because of these observations, 0.05 mg/m3 was established as the MAK (the maximum concentration in the German workplace) value for MDI, to be reasonably practicable under workplace conditions, and there is a continuing remit to reduce exposure levels as far as reasonably practicable with technology that is currently available. 2,2'-Methylenediphenyl diisocy. 04CK23 a`@'a\5IL) 1g("i In: AIP Conference Proceedings - 2nd International Conference on Materials Engineering and Science, IConMEAS 2019. An oligourea was synthesized from 4,4-MDI and 4,4-MDA and shown to be mainly diurea. The question of whether MDI vapour or aerosol can hydrolyse in humid air to yield MDA was assessed in a long-term study (Appelman et al., 1986) and a study of chipboard production (Giersig, 1989). May cause an allergic skin reaction. EFFECTS ON LABORATORY MAMMALS AND IN VITRO TEST SYSTEMS, 8.4.2 Chronic exposure and carcinogenicity, 8.6 Reproductive and developmental toxicity, 9.2.2 Long-term exposure and carcinogenicity, 10. 207. Wazeter FX (1964a) Acute inhalation toxicity (LC50) in male albino rats 12.3.64. International Research and Development Corporation (unpublished report) [cited in EU, 1999]. Typical polyols used are polyethylene adipate (a polyester) and poly(tetramethylene ether) glycol (a polyether). In the German study evaluating lung decrement, significant reversible adverse effects on lung function were observed in persons exposed to MDI concentrations above 0.2 mg/m3. In: IOP Conference Series: Materials Science and Engineering - 2nd International Conference on Sustainable Engineering Techniques, ICSET 2019. Gas concentrations are in percent by volume. J Phys Chem 65(9):16381639, Kolodziej P, Macosko CW, Ranz WE (1982) The influence of impingement mixing on striation thickness distribution and properties in fast polyurethane polymerization. The haemoglobin adduct of acetylated MDI was considered to be formed by in vivo hydrolysis. Once absorbed, it appears to be predominantly conjugated to protein. Diisocyanates are well known dermal and inhalation sensitizers in the workplace and have been documented to cause asthma, lung damage, and in severe cases, fatal reactions. Lecture, University of Bielefeld, Bielefeld, June (unpublished report). Archives des maladies professionelles de mdecine du travail et de scurit sociale (Paris), 43:481 (in French). Following equilibration, PMDI was added to part of the sediment of two ponds at dosages of 1 and 10 g/litre. Boards are chosen according to the range of expertise required for a meeting and the need for balanced geographic representation. La liste des participants au Comit dvaluation finale figure lappendice 3. Despite these data, the small sample size, possible selection bias for workers involved in litigation, possible confounding factors, lack of pertinent matched control, lack of objective exposure data, and lack of knowledge on mechanism preclude the credibility of the findings. Analysis of HRF production by subpopulations of peripheral blood mononuclear cells showed that lymphocytes and adherent cells were major sources of both spontaneous and antigen-stimulated HRF (cellular immune response) (Herd & Bernstein, 1994). Mutation research, 412:167175. As of 2019, the largest producer was Wanhua Chemical Group. E-mail: Littorin M, Truedsson L, Welinder H, Skarping G, Martensson U, Sjoeholm AG (1994) Acute respiratory disorder, rhinoconjunctivitis and fever associated with the pyrolysis of polyurethane derived from diphenylmethane diisocyanate. Seel K, Walber U, Herbold B, Kopp R (1999) Chemical behaviour of seven aromatic diisocyanates (toluenediisocyanates and diphenylmethanediisocyanates) under in vitro conditions in relationship to their results in the Salmonella/microsome test. The range of variation reflects variations from various sources of information, i.e., from a German review (DFG, 1997), US Toxicological Review (US EPA, 1998), and the EU draft document (EU, 1999). The first step of the production of MDI is the reaction of aniline and formaldehyde, using hydrochloric acid as a catalyst to produce a mixture of diamine precursors, as well as their corresponding polyamines: Then, these diamines are treated with phosgene to form a mixture of isocyanates, the isomer ratio being determined by the isomeric composition of the diamine. %%EOF Compound-associated yellowish particulate material was found in alveolar luminar macrophages in both sexes at 0.98 and 6.03 mg/m3. The first draft undergoes primary review by IPCS to ensure that it meets the specified criteria for CICADs. An inhalation exposure study using radiolabelled MDI indicates that some form or portion of MDI is distributed throughout the body, predominantly in the lungs, muscle, kidneys, and digestive tract. However, monomeric MDI is soluble in octane, benzene, and kerosene. All the subjects had worked in a plant where a resin based on MDI was used in the manufacture of wood chipboards. Only one pulmonary adenocarcinoma (10 mm in size) was observed in one male exposed to this concentration. hbbd``b`Z$s1:qX @w'AFl"H7 Y 0 ' There are no data available for oral exposure, but it is unlikely that humans are exposed to MDI by the oral route. British journal of industrial medicine, 50:10031007. Fetal body weights were comparable in all groups, and no external treatment-related abnormalities were observed in the fetuses. Sa tension de vapeur est infrieure 1 mPa 20 C. It has a transient existence in water; thus, its water solubility is only notional. Un estudio de exposicin por inhalacin con MDI radiomarcado indica que alguna forma o parte del MDI se distribuye por todo el organismo, sobre todo en los pulmones, los msculos, los riones y el aparato digestivo. Fundamental and applied toxicology, 22:186194. The incidence of olfactory atrophy was statistically significant in high-dose males (5/10) and high-dose females (6/10). The designations employed and the presentation of the material in this publication do not imply the expression of any opinion whatsoever on the part of the Secretariat of the World Health Organization concerning the legal status of any country, territory, city, or area or of its authorities, or concerning the delimitation of its frontiers or boundaries. J Am Chem Soc 81(18):48384842, Barblat A, Caraculacu AA, Iurea V (1978) The influence of the structure of aromatic diisocyanates on the preparation and the properties of polyurethanes. Out of 5541 new cases reported between 1989 and 1991, 28% were occupational asthma. The treated soil was then used for the studies. . In an epidemiological study of occupational dermatitis in five different shoe factories, 246 workers were interviewed, examined, and patch-tested using standard and occupational patch-test procedures of the International Contact Dermatitis Research Group (Mancuso et al., 1996). Hay que sealar que el documento de la UE es todava un borrador pendiente de aprobacin y que la informacin que presenta en las secciones relativas al medio ambiente se basa fundamentalmente en estudios no publicados. Since the number of the effects observed in the 9 mg/m3 group was within the limits of biological variability, a NOAEL for developmental effects of 9 mg/m3 was determined in this study. In human and environmental toxicology or because of their expertise in human and environmental toxicology or because of experience... Lake sediment, to which caged rainbow trout ( Oncorhynchus mykiss ) were.! Berdondini RM ( 1996 methylene diphenyl diisocyanate reaction with water occupational dermatitis, skin sensitization, and adducts of both haemoglobin... ( in French ) alcohols should be noted that this guidance value may not protect against occupational sensitization weights. 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For balanced geographic representation were also observed in the fetuses for CICADs le MDI est utilis pour la fabrication base! International Isocyanate Institute for Bayer AG, Leverkusen ( Report No.10417 ) resin based selected!