• Title/Summary/Keyword: isocyanate group

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Reaction of Diisobutylaluminum Hydride-Dimethyl Sulfide Complex with Selected Organic Compounds Containing Representative Functional Groups. Comparison of the Reducing Characteristics of Diisobutylaluminum Hydride and Its Dimethyl Sulfide Complex

  • Cha, Jin-Soon;Jeong, Min-Kyu;Kwon, Oh-Oun;Lee, Keung-Dong;Lee, Hyung-Soo
    • Bulletin of the Korean Chemical Society
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    • v.15 no.10
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    • pp.873-881
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    • 1994
  • The approximate rate and stoichiometry of the reaction of excess diisobutylaluminum hydride-dimethyl sulfide complex($DIBAH-SMe_2$) with organic compounds containing representative functional group under standardized conditions (toluene, $0{\circ}C$) were examined in order to define the reducing characterstics of the reagent and to compare the reducing power with DIBAH itself. In general, the reducing action of the complex is similar to that of DIBAH. However, the reducing power of the complex is weaker than that of DIBAH. All of the active hydrogen compounds including alcohols, amines, and thiols evolve hydrogen slowly. Aldehydes and ketones are reduced readily and quantitatively to give the corresponding alcohols. However, $DIBAH-SMe_2$ reduces carboxylic acids at a faster rate than DIBAH alone to the corresponding alcohols with a partial evolution of hydrogen. Similarly, acid chlorides, esters, and epoxides are readily reduced to the corresponding alcohols, but the reduction rate is much slower than that of DIBAH alone. Both primary aliphatic and aromatic amides examined evolve 1 equiv of hydrogen rapidly and are reduced slowly to the amines. Tertiary amides readily utilize 2 equiv of hydride for reduction. Nitriles consume 1 equiv of hydride rapidly but further hydride uptake is quite slow. Nitro compounds, azobenzene, and azoxybenzene are reduced moderately. Cyclohexanone oxime liberates ca. 0.8 equiv of hydrogen rapidly and is reduced to the N-hydroxylamine stage. Phenyl isocyanate is rapidly reduced to the imine stage, but further hydride uptake is quite sluggish. Pyridine reacts at a moderate rate with an uptake of one hydride in 48 h, while pyridine N-oxide reacts rapidly with consumption of 2 equiv of hydride for reduction in 6h. Similarly, disulfides and sulfoxide are readily reduced, whereas sulfide, sulfone, and sulfonic acid are inert to this reagent under these reaction conditions.

Physical Properties of High-Solid Coatings with Acrylic Resins Containing Acetoacetoxy Group and Allophanate-Trimer (Acetoacetoxy기 함유 아크릴수지와 Allophanate-Trimer에 의한 하이솔리드 도료의 도막물성)

  • Jo Hye-Jin;Shim Il-Woo;Park Hong-Soo;Kim Seung-Jin;Kim Seong-Kil
    • Polymer(Korea)
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    • v.30 no.3
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    • pp.230-237
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    • 2006
  • Copolymers(HSA-98-20, HSA-98-0, HSA-98+20) which we acrylic resin containing 80% solid content were synthesized by the reaction of monomers, including methyl methacrylate, n-butyl acrylate, and 2-hydroxyethyl acrylate with a functional monomer, acetoacetoxyethyl methacrylate (AAEM), which nay give improvements in cross-linking density and physical properties of films. The physical properties of prepared acrylic resins, containing AAEM, are as follows viscosities, $1420\sim5760cps$ ; number average molecular weight, $2080\sim2300g/mol$; polydispersity index, $2.07\sim2.19$ ; and conversions, $88\sim93%$. In the next step, high-solid coatings (HSA-98-20C, HSA-98-0C, HSA-98+20C) were prepared by the curing reaction between acrylic resins containing 80% solid content and isocyanate at room temperature. Various properties were examined on the film coated with the prepared high-solid coatings. The introduction of AAEM to the coatings enhanced the abrasion resistance and solvent resistance, which indicated the possible use of high- solid coatings for top-coating materials of automobile. Since the curing by viscoelastic measurement occurred in sequence of HSA-98+20C > HSA-98-0C > HSA-98-20C, it was concluded that the curing rates became faster with incresing $T_g$ values.

Toughness of Polyurethane-Modified Unsaturated Polyester Resin (폴리우레탄으로 개질한 불포화 폴리에스테르 수지의 강인성)

  • Hwang, Yeong-Geun;Min, Kyung-Eun;Choi, Gwan-Young;Kim, Woo-Sik;Lee, Dong-Ho;Park, Lee-Soon;Seo, Kwan-Ho;Kang, Inn-Kyu;Jun, Il-Ryun
    • Polymer(Korea)
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    • v.25 no.1
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    • pp.71-77
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    • 2001
  • Unsaturated polyester(UP) resin is one of the major thermosetting resins. It is very useful as the matrix resin of the composite material because of its low viscosity. The polymer resin, however, has several drawbacks; The volume shrinkage occurs during the crosslinking reaction of the UP resin with styrene monomer and the resulting polymer is weak to the alkali and also brittle. The mechanical properties of UP resin can be improved by blending various materials. In this study, polyurethane(PU) was used as a modifier in order to enhance the toughness of the UP resin. The goal of the research is to study the effect of the polyol molecular weight as a PU soft segment and the PU contents on the toughness of PU-modified UP resins. UP/PU polymer network may occur through the reaction between isocyanate group in the methyldiisocyanate(MDI) and hydroxyl group in the UP molecules. The maximum toughness value was shown at 2 wt% of the PU content. This effect results from the incorporation of the PU segment into the UP resin.

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Synthesis of Eco-Friendly High Solid Acrylic Resins and Curing Properties of Acrylic Urethane Resin Coatings (환경 친화형 하이솔리드 아크릴수지의 합성과 아크릴 우레탄 도료의 경화 특성)

  • Kim, Jin-Wook;Lee, Dong-Chan;Choi, Joong-So
    • Korean Chemical Engineering Research
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    • v.55 no.5
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    • pp.586-592
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    • 2017
  • In this study, acrylic resins with solids content of 75% were prepared by addition polymerization of n-butyl acrylate (BA), methyl methacrylate (MMA), 2-hydroxypropyl methacrylate (HPMA) and acetoacetoxyethyl methacrylate (AAEM) monomers. At this time, the glass transition temperature ($T_g$) of the acrylic resin was changed to 20, 30 and $40^{\circ}C$, and the hydroxyl value (OH value) was changed to 60, 90 and 120. As a result, the viscosity of acrylic resin increased with increasing $T_g$ and hydroxyl (OH) value. The synthesized acrylic resin was designed to have a high cross-link density to maintain high elasticity and high durability. The crosslinked acrylic resin was used to prepare an acrylic urethane clear coating by curing reaction with a block isocyanate (Desmodur BL-3175). The physical properties of the clear paints were analyzed by measuring viscosity, adhesion, pencil hardness and $60^{\circ}$ specular gloss. Acrylic urethane clear coatings were prepared as specimens and evaluated for various properties to be applied as top coatings for coil coating. The prepared coatings were excellent in adhesion, excellent in $60^{\circ}$ specular gloss and pencil hardness, and eco-friendly.

Synthesis and Properties of Poly(ester-imide) Resin for High Temperature Resistant Electrical Insulation (고내열성 전기 절연용 Poly(ester-imide) 수지의 합성 및 물성)

  • Huh, Wansoo;Lee, SangWon;Kim, Jeongyeol;Park, Leesoon;Kim, Soonhak;Haw, JungRim
    • Applied Chemistry for Engineering
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    • v.10 no.5
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    • pp.767-771
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    • 1999
  • Poly(ester-imide)(PEI) for the electrical insulation coating was synthesized and evaluated with one-step method as well as two-step method. For the synthesis of poly(ester-imide), imide repeat unit of N,N'-(4,4'-diphenylmethane) bistrimellitimide(DID) was initially made from trimellitic anhydride(TMA) and methylene dianiline(MDA), followed by the second stage reaction of esterification. One-step reaction was performed by reaction of TMA, MDA, dimethyl terephthalate(DMT), ethylene glycol(EG), and 1,3,5-tris-(2-hydroxy ethyl) isocyanurate(THEIC) in m-cresol solvent at a time. The synthesized poly(ester-imide) was cured with xylene, P-5030K(phenol-formaldehyde resin), TK-8(TDI type blocked polyisocyanate) and tetrapropyltitanate(TPT). It was found that the content of hydroxyl group, amount of DMT, and imide repeat unit played important role for the properties of electrical insulation coating film.

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A Study of Adverse Health Symptoms of Spray Painters Using Isocyanates(HDI) (분사페인트에 의한 이소시안화물의 노출이 건강에 미치는 영향에 관한 연구)

  • Lee, So-Gil;Pisaniello, Dino;Lee, Nae-Woo
    • Journal of the Korean Society of Safety
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    • v.23 no.3
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    • pp.79-86
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    • 2008
  • In the manufacturing industries using HDI(hexamethylene diisocyanate) product hardeners, exposure to HDI is common to spray painters in terms of inhalation and dermal or ocular contact. Due to a lack of information for spray painters in automobile and furniture industries, a questionnaire survey was conducted for the prevalence of adverse health symptoms(33 spray painters and an unexposed group n = 91) to assess the importance of personal controls. Despite the small sample size, common health symptoms were reported, such as skin symptoms(dry cracked skin-61% and dermatitis/skin irritation-33%) and respiratory symptoms(phlegm-49%, asthma-21%). In addition, other adverse health symptoms were reported, such as skin rash(12%), cough(39%), shortness of breath with wheezing(30%), chest tightness and difficulty in breathing(30%). No significant eye symptoms were reported. It was founded that the adverse health symptoms reported in this study were related to poor personal work practices and inappropriate PPE use. Therefore, appropriate personal controls like PPE use, work practices, regular training and education are suggested to minimize the risk of health symptoms. In addition, medical examination will also be suggested for individual health effects.

Synthesis and pesticidal activity of ricinine derivatives (Ricinine 유도체(誘導體)의 합성(合成) 및 농약활성(農藥活性))

  • Kwon, Oh-Kyung;Lim, Soo-Kil;Hong, Su-Myeong;Lee, Sung-Eun;Kyung, Suk-Hun
    • The Korean Journal of Pesticide Science
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    • v.2 no.1
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    • pp.24-31
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    • 1998
  • Chemical derivative synthesis of ricinine, an active compound of Ricinus communis which showed high mortality against brown planthopper (Nilaparvata lugens), was performed to improve its pesticidal activity and the toxicity of 12 synthetic derivatives against major insect pests and phytopathogenic fungi were examined. Carbamate derivatives of ricinine could be synthesized from the precursor of ricinine, chloronorricinine and norricinine, whereas the derivatives were not synthesized from chlororicinic acid and ricinic acid having ketone group of pyridine ring. In organophosphates, reaction with oxon type of phosphate gave better yield than thiono type. Among the organophosphate derivatives of ricinine, thiono type of derivative structure gave $96.3%{\sim}100%$ mortality of the brown planthopper and the two-spotted spider mite (Tetranychus urticae) at 500 ${\mu}g/ml$ level. On the other hand, carbamate derivatives did not show insecticidal activity. In the fungicidal activity of ricinine derivatives, the derivative having amino radical at the 2 position of ricinine gave 85 to 100% of mycelium growth inhibition effect against ten major plant pathogens at the 200 ${\mu}g/ml$ level. In particular, the control value of the derivative on the rice blast (Pyricularia grisea) and barley powdery mildew (Erysiphe graminis) at the 250 ${\mu}g/ml$ level in vivo under greenhouse conditions was 92% and 96%, respectively.

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Polyurea Cross-linked Silica Aerogel with Improved Mechanical Strength by Applying a Precursor Having a Plurality of Amino Groups (복수의 아민기를 가지는 전구체를 적용하여 기계적 강도를 향상시킨 폴리우레아 가교 실리카 에어로겔)

  • Lee, Wonjun;Kim, Taehee;Choi, Haryeong;Kim, Jiseung;Lee, Hong-Sub
    • Journal of the Microelectronics and Packaging Society
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    • v.29 no.4
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    • pp.15-20
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    • 2022
  • Aerogel is a material having a nanopore structure based on a high porosity. Due to this high porosity, it has excellent properties not found in conventional materials, but its application has been limited due to low mechanical strength. Therefore, to improve the mechanical strength of the aerogel, polyurea crosslinking was introduced and a precursor having an amine group essential for polyurea polymer formation was selected to synthesize a polyurea crosslinked aerogel composite. In addition, the crosslinking of polyurea was adjusted according to the number of amine groups present in aminosilane. It was confirmed through various analyses that the nanopore structure of the aerogel was maintained to have mesopores. The aerogel thus formed was able to improve the mechanical strength by about two times, and it was confirmed through field emission scanning electron microscope analysis that a one-dimensional polymer was formed on the silica aerogel surface through the introduction of ethylene diamine. The one-dimensional polymer thus formed has improved mechanical properties, resulting in securing an elastic modulus of about 2.66 MPa.